As I got off the school bus, it occurred to me that it was a wonderfully sunny day this morning, and I was bursting with optimism for the new year. I was starting all over here in this town and I sincerely hoped to be able to put my shameful past behind me. I was tired of being called a sissy by my schoolmates and it had gotten to the point where even some of the younger kids were starting to push me around.
I guess I shouldn’t have been surprised by it—all my life I was always shorter and weaker than the other kids and I was never much into sports. The girls called my skinny but even my mom referred to me as ‘frail’, when describing me. To make matters worse, I had a chronic problem with wetting my pants that I was only now achieving some kind of success with. My mom, in her usual practical way, had chosen to make me wear diapers and plastic pants throughout my early childhood, and I had only stopped wearing them to bed last year. During that era of my life, I especially hated it when she made me wear them in plain view, with only a t-shirt and sneakers, like when my aunt came over. It was mortifying to be seen like that, with my plastic pants noisily announcing my presence, although neither seemed too sympathetic to my plight.
I shuddered with revulsion as I remembered these thoughts but I could breathe easy now. I was staying at my aunt’s house while my parents worked out their rocky, mismatched marriage. That meant a different school and more importantly, people who knew nothing of my past.
With the sun out and shining, I was so care free that I almost skipped the short distance to the school building but I stopped myself short. It wouldn’t do to have my new peers seeing me skip like a girl-- not at all. I was determined to carry myself like the young man of 14 that I was—a teenager that was ready to start impressing any girls I could.
Walking inside as manly and tough as I could, I went to my locker to get the stuff I needed for class. The door next to mine was open and I acknowledged the guy with a brief nod. But then as I turned my head away from him, I saw….Her.
Even though the woman who had caught my eye made no attempt to stand out—she did anyway like a cat amongst a group of small mice. She was tall and slim and she walked with the sexiest sashay I’d ever witnessed in my life. It was as if she were literally dripping with sex appeal. I was quite simply agog as I stared openly at her curvy, voluptuous profile. She was wearing a sleek, hugging skirt of thin material that revealed every delectable feature of her sensuous hips and tiny waist. Her long, silky smooth legs seemed to go forever until they ended at her tall, high-heeled sandals. Even amid the gathering of people surrounding her, I could hear the distinctive sound of her shoes as they clicked confidently across the tile floor.
She wore a loose fitting blouse that fluttered in the breeze but beneath that was a tight, low-cut top with a scoop neck that revealed two, jaw-dropping breasts of the most exquisite size and shape. They were truly massive!
As I watched them gently jiggling within her top, my heart skipped a beat and I felt myself starting to drool foolishly. Wiping my sleeve across my face, I saw that not only did she have the body of a goddess, she was a stunning beauty as well! Playful curly locks of flaxen colored hair flowed over her shoulders and down almost to her waist. They framed a face that was pretty and breathtaking all at once—full, luscious lips, a cute button of a nose, and the most gorgeous green eyes on any woman I had ever seen.
I felt my little wiener beginning to stir and my breath was starting to come in short gasps. I was completely overwhelmed!
“Who-who’s that?” I stammered to the guy next to me.
He followed my gaze and nodded appreciatively.
“She’s not someone you want to know,” he said with a strange tone of warning in his voice.
I had difficulty reconciling his caution with the ravishing female image retreating down the hall.
“What do you mean?” I inquired, puzzled.
“That’s Ms. Taylor,” he said, the fear plain in his voice, “she works in the punishment hall.”
“Punishment hall? What’s that?” I asked.
“I gotta go,” he suddenly said in a hurry.
Slamming the thin steel door of his locker, he disappeared into the moving crowd of kids heading to their classes as I pondered his thought provoking, yet enigmatic words. It was hard for me to imagine that beautiful creature being some sort of disciplinarian but I had little time to think more about it, I was going to be late myself if I didn’t get moving.
Bolting down the hall, I headed in what I thought was the right direction of my class but soon found that I had made a mistake. For some strange reason, they had put all the even numbered classrooms down one hall and all the odd numbered ones down the opposite hall. By the time I finally found my classroom, the bell had already rung and I was several minutes late.
Going inside, I closed the door behind me as quietly as I could but all eyes were upon me as I entered the room.
A sharp female voice cut across the expanse of the classroom, clearly directed at me.
“What is your name, Young Man?”
I cleared my throat nervously and looked up to see everyone, including the stern looking teacher staring at me.
“Um…Ethan…Ethan Ostroff.”
“Well, Ethan Ostroff, here at the Francis Merrimont Boys School, we don’t tolerate slackers or sloppy attendance. Please come up here to my desk,” she said in a voice that could cut through hardened steel.
My heart sank as I trudged slowly across the room, dragging my feet as the unfamiliar group of faces stared openly at me. Keeping my eyes lowered, I didn’t truly look at my new teacher until I was standing before her.
“Put your books down on the desk,” she ordered me, pointing her long nailed finger at her desk. She was a picture of authority, severe, uncompromising, and forceful, yet even with her hair pulled back behind her in a utilitarian style, I had to admit she was very attractive. Her dark, demanding eyes drilled into me, filling me with fear and foreboding.
“Place your hands, palm down on the desk,” she told me evenly as she walked over to the blackboard. She reached over and picked up a thin stalk of bamboo that was about three feet in length. I hadn’t realized it at first, but by placing my hands on her desk, I was forced to bend over, leaving my bottom facing outward toward the class.
Without a moment’s hesitation, she came around and brought the bamboo cane down across my cheeks with a whistle that filled the room.
“OWWW!!” I yelped and bucked forward as my hands shot back to protect my stinging rump.
“Get back in position!” she barked, and filled with terror, I hastened to follow her command.
“The next time you move without being told to, will earn you ten more.”
I gulped hard as I placed my hands back down on the desk.
Whoosh!
The cane felt like it went right through the thin fabric of my pants and underwear and I howled in pain, stomping my feet against the ground.
Whoosh!
“OWW-WOW!!” I wailed, as the tears began forming in my eyes.
To my utter relief, the teacher calmly walked over and set the cane back down in corner.
“There, let that be a lesson to you. Now you may sit down,” she instructed me, “The next time I have to discipline you, will result in a spanking—do I make myself clear?”
“Ye-yes Ma’am,” I replied shakily.
Man, this place was strict!
Rubbing my throbbing buns, I sniffled and fought back the tears that threatened to spill down my cheeks as I made my way to the last remaining empty seat in the room. Several of the kids snickered at me as I walked past, apparently amused at the humiliating punishment I’d just received.
“Class. My name is Ms. Franklin and I will be your teacher for the school year,” she announced in a voice that filled the room and left no doubt that there would be no funny business in this class.
“You will find that I am intolerant of sloppy and insubordinate behavior. Anyone wishing to test me on that will soon find himself with a very sore bottom.”
The class was silent as a grave as they considered this stern mistress that would be their teacher for the next nine months. She continued to lecture us with a rather lengthy list of rules but I was consumed with shame and self-pity at my poor start and I hardly heard a word she said.
To my relief, the rest of the morning dragged on but was otherwise uneventful.
During the lunch break, I was mostly by myself until a few younger kids came walking by my table. The one in front, a tough looking individual reached down and helped himself to my cake, smirking at the cleverness of his theft.
“Hey! Stop that!” I cried out, in my high pitched voice.
As everyone around me turned to see who was squealing like a girl, I instantly regretted my outburst.
“Stop that!” the boy said in mocking tone of voice as he bit into my cake just out of reach.
I debated the wisdom of standing up to make an issue of it—by the looks of him, he appeared pretty able to withstand any attempt I might make to retrieve my dessert, but on the other hand, if I just sat and did nothing, everyone around me would know they could pick on me with impunity. Looking up to the three toughs before me, I decided losing my cake wasn’t worth getting beaten up for. With all eyes upon me, I went back to eating my lunch, hoping my tormentors would just walk away and forget me. Unfortunately, it would seem they had other plans.
Coming around to my side of the table, the kid who’d stolen my cake walked up to me and pushed me rudely, goading me to fight him. I looked back at him angrily but did nothing to defend myself. All around me, everyone was watching to see what I’d do and I knew my reputation was plummeting like a box of rocks.
“What a woos!” the boy exclaimed with a guffaw.
“Leave me alone,” I whined, but in response he reached over and slapped me on the face.
“Ow!” I cried as everyone around me burst into laughter.
I stood up to face him but just as I did, he took my drink and splashed it across the front of my jeans, making it look like I peed myself.
Fully enraged, I threw myself at him but he easily dodged me and we began our scuffle in earnest. He connected me with a couple of haphazard blows before a strong hand lifted me bodily to my feet. Looking around, I found myself staring into the hard features of a middle aged woman wearing a kitchen skirt, obviously one of the servers from the cafeteria. She was built quite sturdily and our efforts to free ourselves met without success.
“So, you like to fight do you?” she snarled at us accusingly as she held us apart.
At the same time, we both began launching into our spirited defenses but she was having none of it.
“Come along you two, you can explain it to the principal, Mrs. Sterne,” she said as she hauled us out of the room. I heard several kids murmuring something about a spanking under their breath as we passed them and I began to grow fearful again.
Although the last thing I wanted was to get a spanking on my first day of school, there was certainly no way I was going to escape the clutches of this brute of a woman next to me. She kept up a brisk pace as she dragged us by our collars down the hall toward the dreaded principal’s office. When we arrived another boy was just leaving. Tears were streaming down his face and he was rubbing his bottom through his jeans. I gave him a look of sympathy but my heartbeat had already doubled from its pace of a minute ago.
Stepping into the office, I gazed for the first time at Mrs. Sterne, the woman in charge of Francis Merrimont Boy’s School. Wearing a look of strictness on her face, she was formidable to behold and I nearly wet my pants in fright as I stood before her intimidating demeanor.
By my estimates, she was over six feet tall with her high heels and she wore trim black slacks that hugged her curvy hips. Big, round breasts strained mightily at her white semi-see thru blouse and I could easily make out the white demi-cut bra she had underneath. In any other circumstances, I would have been awestruck by this dominating beauty but today as I stood quaking before her, I was petrified. She had long, silky black hair and it was pulled back on either side which only seemed to accentuate her pretty features. I was entranced with her strong, dark eyes, and her full, wine-colored lips which were drawn tightly in disapproval as she stared down at me.
“Another pair of unruly boys, Mrs. Snagworth?” she asked with obvious displeasure.
“I’m afraid so,” the old battleaxe replied, although she didn’t sound at all sorry to me, “I caught them fighting in the lunch room.”
Before I could utter a word in defense, the bully who’d started the fight suddenly burst into tears and began sobbing loudly, proclaiming for anyone who would listen, that I had terrorized him and began attacking him physically. I made numerous attempts to refute him, but Mrs. Sterne appeared skeptical and it seemed that his initiative was rendering my own arguments futile.
“Thank you, Mrs. Snagworth, you may go now,” the gorgeous principal told her.
The cafeteria woman nodded and left the room, obviously pleased with herself at having brought another pair of ruffians to justice.
Meanwhile, Mrs. Sterne sat down in a straight backed chair that had been placed next to her desk and she began unbuttoning the boy’s pants that had fought with me. He begged and pleaded with her to spare him but she only ignored his whining and took him over her lap. With his pants down around his ankles, she picked up a long rectangular paddle from her desk and began spanking the boy over his snug white underwear.
I watched with undisguised fascination as she slapped his round, youthful cheeks soundly with the wooden instrument, making him buck and kick as he sobbed real tears. I bit my lip in angst as I she swatted his helpless bottom forcefully and harshly, with practiced effort, making sure he got his full measure of punishment. I watched as his cheeks went from pale white, to hot pink, to a glowing, cherry red.
Before long, the spanking was over and she helped him up to his feet, pulling his pants back up for him. Tearfully, he wiped his sleeve across his face as she dismissed him to go back to class.
“And now, its time for your spanking, Little Boy,” she told me in a voice that made my hair stand on end.
She was so pretty that I was astounded she could be so severe. I began babbling excuses again but she cut me off in mid-sentence.
“--Have you wet your pants, too?” she said suddenly as she stared hard at my wet crotch.
In all the excitement of the bully’s punishment, I had entirely forgotten about my own appearance.
“N-no Ma’am,” I stammered uncertainly, “That-that boy—he-he made me—I mean—he spilled the water on me.”
That didn’t come out the way I wanted and I knew it didn’t sound very convincing, a fact that was made obvious as she stared down at me in disbelief.
“Don’t lie to me, Young Man,” she said with an edge on her voice that made me gulp with fear, “I don’t like liars and I especially don’t like liars that make trouble in my school. That boy is obviously younger than you so I know he didn’t pick the fight with you.”
“B-but I—“
“And don’t stand there and tell me you didn’t wet your pants either, because I can see very well that you have.”
I couldn’t believe how badly this was going for me! My mind was racing double time as I tried to think what course of action was best for me. Did I admit to what she suspected, or stick to my story that I knew was true? Either way, I knew I was going to get paddled by this strict, albeit hot looking woman, and there was nothing I could do about it.
“I didn’t mean to wet myself!” I suddenly blurted out, hoping for some measure of sympathy from her.
“Well, we’ll take care of that in a minute,” she assured me, “But first, its time to take you over my lap.”
I whimpered and fought back the tears as she unzipped my pants and let them drop around my skinny ankles. With long, finely manicured fingernails she reached inside the waistband of my wet underwear and snaked them down my thighs, causing me to gasp with surprise. I tried to reach down and hold them in place but she slapped my hands away and lowered them past my knees. Why was it necessary to take my underwear down? She hadn’t done that with the other boy. Staring at my tiny pecker with a look that seemed to confirm her suspicions, she shook her pretty head in disapproval. I’ve always had a small wiener and ever since I can remember, it’s been a source of acute embarrassment for me. I blushed hot red with shame as numerous emotions flooded through my body. Before I could contemplate the humiliation of being exposed before her, she took me over her firm lap and positioned me in such a way as to cause my feet to be off the ground. Choking back a sob, I struggled to gain my balance as I stared down at her tall, glossy black high-heeled pumps. I felt her rubbing my soft, tender buns with the smooth wooden paddle as she lectured me on my misdeeds.
“Sometimes, we get boys in here who think they’ve grown up and are already men.”
She finished her sentence by smacking my bare rump harshly and soundly with the paddle.
“OWWWW—OOWW!” I wailed, surprised at the intense sting of that fearsome instrument.
“They think they can come in here and do as they please…”
SMACKKK!!
I kicked my feet wildly as I cried out loudly, instantly bursting into tears.
“But you are obviously not grown up.”
SMACKKK!!
I howled out in pain again and then felt her rub my inflamed cheeks with the paddle as she continued to scold me.
“Wetting your pants like a little baby—you should be ashamed of yourself!”
She emphasized her point by smacking each stinging cheek individually.
SMACK!! SMACKKK!!
“I can see that you’re just an immature little boy.”
SMACKKK!!
“And believe me, I know just what to do with little boys that can’t control themselves.”
SMACK!! SMACKKK!!
I sobbed and shook my balled fists in childish helplessness.
“So, you thought you could come into my school and start some trouble did you?”
SMACKKK!!
“You wanted some attention, didn’t you—and now you’re getting it.”
SMACKKK!! SMACKKK!!
“Oh yes, Little Boy, I’ll make sure you get all the attention you deserve.”
She continued with a fierce rain of biting, stinging slaps to my helpless, tender bottom while I bawled like a baby. At last, she finally stopped and stood me up on my shaky legs. Crying unashamedly, I reached down to pull my pants and underwear back up.
“No, those can stay where they are for now,” she firmly informed me.
What did she have in mind for me, my mind was shouting as she pulled my shirt up and off of me. Reaching into her drawer, she pulled out a folded garment, made of soft fuzzy pink material. My gaze alternated from her big, round breasts that were pushing against her tight, sheer white blouse, and the girlish top that she was getting ready to put over me. I could see that it was a pull over, with a short row of buttons that secured it in back. White scalloped lace adorned its neckline and its short frilly cuffs, but I stared dumbfounded at the Care Bears figures which were playing on the front of it. Surely, she couldn’t mean for me to wear this, I wondered in disbelief.
As if to answer my unspoken question, she held it open and lowered it over my head as I stared helplessly into her hard, steely eyes. Unable to hold her superior gaze, I looked down, my eyes falling upon her unbelievable bust line as she adjusted the top on me. Seeing the object of my attention, she slapped my cheek soundly, causing a fresh torrent of tears to come flooding forth.
“Don’t stare at my chest!” she warned me harshly.
Jerking me around, she began buttoning up the top in back just as the buzzer on her desk went off.
“Mrs. Sterne?” the female voice said.
“Yes, what is it, Brittany?” she said as she finished buttoning me up.
“There is a Mrs. Turner here to see you,” Brittany replied.
“I’m on the way out now,” she told her,” Can you call Ms. Taylor in?”
Before Brittany could answer, the door opened and Ms. Taylor, the bombshell I had first seen this morning in the hall, walked in.
“Hi Jennifer, can you take over for me here, it seems this little boy is having a problem keeping his pants dry,” Mrs. Sterne said to her, as if I weren’t even in the room.
More embarrassing than her statement, was the fact that my idol was now staring down at my tiny peanut in awestruck amusement. She brought her slim, finely manicured hand to cover her mouth which was open in surprise as she gazed with undisguised fascination at my little member, hardly hidden by the sparse patch of light, tawny pubic hair. I couldn’t tell if she was hiding her surprise or her laughing, because she seemed delighted with my state of dress, or rather, undress.
My face, still wet with tears, burned red hot with shame as she bent over to look closer at me. I was absolutely mortified to be caught like this, naked from the waist down and wearing a soft, pink Care Bears shirt that screamed out sissy.
“He’s just the cutest little thing!” she exclaimed as she placed her hands on her knees to look down at me like I were a doll. Despite the smoldering humiliation I was feeling, I couldn’t help but notice the yawning cleavage between her two huge, soft breasts that were threatening to spill out of her snug top.
“Don’t you worry, Little Boy,” she assured me, “I’ll get you all fixed up.”
“Thanks Jennifer,” Mrs. Sterne said, obviously finished with me, as she strode out the door, leaving it open behind her.
I watched her leave with mixed feelings but as she walked out of view, I could see her secretary, a smile on her face as she gazed at me from beyond in the other room. I blushed again as I turned away, desperate to get my diminutive wiener covered and frustrated with how many women had already seen it today.
“Can I put my pants back on now, please?” I pleaded fervently with the beautiful woman before me. I felt so completely naked before her, with my little penis twitching nervously, I felt acutely aware every time she looked down at me.
Ms. Taylor only giggled as she bent over and began removing my shoes and pants, along with my underwear.
“Don’t you worry,” she winked, a ravishing smile on her face, “I’ve got something just perfect for you.”
I had no idea what she was talking about but she took my hand and led me into an adjoining room, that looked more like a nursery than something I would expect at a high school. Two large cribs were along one wall while a netted playpen dominated the room and I suddenly became aware of the stale smell of wet diapers. The not so subtle aroma instantly brought back strong feelings of inadequacy as I relived my troubled childhood, growing up in diapers. Obviously people who were kept in here must have no control at all if they were still wetting their pants and I felt utterly ashamed to be in such company.
My eyes took in a changing table, several dressers and other baby furniture, all done in pink or girlish pastel colors. The walls were covered with nursery print characters and stuffed bears filled the corners. I couldn’t understand why there would be a need for such a room, in this school of young adults but here it was, nonetheless.
I gazed with dread as I noticed two large stacks of cloth diapers, and an open drawer next to them filled with plastic pants of all colors and styles. Baby powder, diaper rash ointment, oversized diaper pins—I recognized all of it instantly and my heart began beating feverishly.
I quickly saw a young fellow, who was about the same age as myself, put his teddy bear down and look at Ms. Taylor, his eyes imploring her to come over. His mouth was filled with fat baby’s pacifier preventing him from speaking and as I looked down, I could see the thick diapers he was wearing were quite wet which was evident due to the clear plastic pants covering them.
Covering my crotch with my hands, I tried to marshal my best defense at what I suspected she had in mind for me.
“M-Ms. Taylor, really—I didn’t wet my pants—it-it was the other kid--”
Without answering me, she scooped up another large pink pacifier lying on the dresser top and plopped it in my mouth, holding it there until I submissively accepted it.
“Hush, little sissy,” she said with a devastating smile that made me shudder.
As I sucked uncertainly upon the fat rubber nipple in my mouth, I felt like I was being hopelessly led down a path against my will, and without any means to prevent it.
Still leading me by the hand, she took me over and set me down on the large, vinyl covered changing table whose edges were lined with plastic lilac colored lace.
“I have just the thing for little boys who are still wetting their pants,” she said cheerily, “What you need, is a nice, fluffy soft diaper and some plastic panties.”
I shook my head no vigorously, but she reached down and easily picked me up by my ankles, sliding a thick stack of white cotton diapers under my still blazing rump. I watched her closely as she squeezed a large glob of diaper rash ointment into her slim hand and begin rubbing it, slowly and softly across my punished cheeks.
“Most little sissies take to their diapers right away,” she assured me with her pleasant smile.
I had to admit, between her fantastic bosom, and the sensuous feel of her slippery hands across my bottom, I was starting to get very excited. Alas, too soon she finished her task, and she wiped the excess ointment onto the cloth beneath me. Taking a large container of baby powder, she began humming as she sprinkled a generous quantity over my slowly stiffening member.
“Mm-hm,” she said with a knowing smile, “Looks like this little sissy likes getting put into diapers, doesn’t he?”
I blushed hotly, ashamed of my confused feelings and my budding erection but her warm smile washed over me like a welcome bath. Her soft hand smoothed the fragrant powder across my tiny pee-pee as the familiar babyish scent filled my nostrils. Visions of my diapering at home rushed into my mind and I blushed again at the thought that I had already been regressed so quickly.
My wiener was stiff and throbbing, rising to its full glorious height of two and a half inches but she stopped and began pulling the cloth up and over it. I whimpered with frustration as she took a pair of pink, bunny-headed diaper pins and pinned either side snugly into place.
Patting the thick, bulky front of my crotch with satisfaction, she reached over and retrieved a pair of pink, nursery print plastic pants. As she did so, her fantastic breasts stretched the fabric of her top tightly which hugged them wonderfully, and I sighed with admiration.
“Feet up,” she said merrily, and I dutifully poised my feet so she could slide the waterproof pants down my legs. I was ashamed to have her dressing me like an infant but I was so taken with this stunning hottie that I couldn’t gather the will to stop her.
“These will keep the wetness right where it belongs,” she said with that pretty smile but I blushed as I saw the babyish panties being fitted over my fat diapers. I kicked my feet and squirmed in weak protest but my movements only seemed to serve to assist her in positioning the crackly vinyl pants in place. Lastly, she dusted the inside of my thighs where the thick bulk of my diapers would rub against them.
“There. Now its time for us to have a little talk,” she said as she began putting the diapering supplies away.
Stopping by to squeeze the diapered seat of the other boy in the room, she shook her head and led him into the large playpen that was in the center of the room.
“Yes, your diapers are wet but I think they can take a little more,” she said sweetly, “Why don’t you play with your dollies while I take care of this new sissy.”
He didn’t seem too happy about that option and he made a babyish sounding squeal from behind his pacifier as she put him into the playpen. Still, once he was inside, he sat down peacefully enough, landing with a wet squish on his thickly padded rump.
Picking up a stuffed bunny rabbit, she brought it over to me and then beckoned me towards a large love seat against the wall. Easing herself down, I watched as the short hem of her skirt rose up her silky legs, exposing more and more of her delicious thighs and I was entranced by her tall, high-heeled sandals, with their tiny straps going across her delicate ankles. Everything about her was so incredibly sexy—even her toenails were meticulously manicured and painted and she captivated my entire focus.
“Come here Sissy,” she said in an inviting half-whisper that gave me butterflies.
I had never been this close to an adult woman of such absolute beauty and my heart was beating a million miles an hour. To be seen like this was terribly embarrassing and I was ashamed to be called a sissy, even if I was dressed like one. Nervously, I waddled over, acutely aware that I looked like a three year-old toddler in my fuzzy Care Bears top and fat, plastic panty-covered diapers.
“Come here sissy,” she repeated, again flashing that devastating smile at me as she patted the top of her firm lap. Stepping over to within reach of her, she picked me up and plopped me down next to her thigh, bringing me back down so that I was now looking up into her pretty face, with her mouthwatering bosom inches away from my face. I could see her soft, luminescent skin as her plump, silky chest rose and fell from her breathing and my little wiener strained against the soft cloth of my diapers.
I was horny as hell and I wanted badly to reach down and give myself some relief!
“My name is Ms. Taylor, Little Boy, what is your name?” She asked as she gently pulled the pacifier out of my mouth.
“E-Ethan Os-Ostroff,” I stuttered nervously. I was so overwhelmed with her female essence I couldn’t even think straight!
“Hello Ethan,” she said softly, with a voice full of warmth and tenderness.
“You know, I can tell a lot about people, the first time I meet them,” she told me, making me feel completely naked before her. She spoke with such confidence and authority, I had no doubt she could read minds.
“And I’ll bet, underneath that exterior you’re trying to present as a tough young man, you’re really just a big sissy who likes nothing better than the soft touch of panties and dresses—am I right?” she asked with her ravishing smile. As she spoke, she ran her long finger slowly across my face, from my ear down to my chin giving me electric chills of pleasure.
I blushed beet red and shook my head, determined to make her believe I was as manly as the rest of my class but she merely chuckled to herself and smiled back at me, showing her total lack of belief.
“And you look like the kind of boy whose mommy had a hard time potty training because you just refused to grow out of your diapers, hmm?”
Despite my best efforts, I couldn’t stop blushing and it was as if she were seeing into my mind! How could she know these things? I shook my head again but I knew she didn’t believe me.
“Looks like someone is blushing,” she said with a big, beautiful smile.
I tried to look away but she gently grasped my chin in her slim hand and brought it back, forcing me to look deep into her pretty, captivating eyes.
“I’ll bet you’re a prissy momma’s boy who misses nursing on his mommy’s breasts…am I right?”
I swallowed hard as I stared down the deep line of her tremendous cleavage. Her massive melons were an inch from my face and I was beside myself with pent up arousal.
“Is this what baby wants?” she said in a syrupy voice used for addressing infants. With the most insanely erotic movements, she slowly and gently stroked the exposed skin of the top of her right breast, tracing the exciting curve of the swollen flesh.
I gulped hard and nodded my head frantically now—I wanted to taste her breasts in the worst possible way!
With slow, teasing moves, she ever so gently put her long fingernail underneath the spaghetti strap holding up the left side of her top and let it fall down her lithe arm. I licked my dry lips in anxious anticipation of what was—unbelievably—about to happen.
“Tsk, tsk,” she said as she shook her pretty head, “Not just yet… First I want you to tell me about yourself.”
My mouth was hanging open in frustration as I stared back up at my hot tormentress. Her snow white bra was now mostly exposed and I gazed hungrily at the delicate, very feminine lace that graced the edges of the smooth cup.
“You are a big sissy, aren’t you?” she said with her pretty smile.
Wearing a thick, cushiony soft diaper and plastic panties, I was helpless to prevent her from learning the truth. I nodded my head silently in response, even as I blushed a deeper shade of red.
“Mm-hm. And you probably like wearing little girl’s panties too, don’t you?”
I blushed and slowly nodded my head again, seemingly unable to deny her. How was she able to read my mind??
“Mm-hm…I’ll bet you like soft, delicate little panties, ones that hug your little bottom and make you feel all femmy.”
I tried looking away to deny what she was saying but I couldn’t with her holding my chin and I found myself nodding my head in shameful agreement. My ears felt like they were on fire as I blushed from my chest up.
“You’re just mommy’s little baby, aren’t you?” she said as she slowly slid the rest of her top off from her right boob.
I bobbed my head yes, and she smiled down at me as she lifted her heavy breast out of its cup and positioned it before my quivering lips.
“Come on little sissy-boy, nurse from my breast like you did with your mommy.”
Her humiliating words washed over me, filling me with childish shame, but I was so worked up, I couldn’t do anything about it. I had never seen a woman’s bare breast, except for my mom’s, and I’d never been in such an intimate situation with such a knockout as this. On top of that, this babe’s boobs were almost as large as my head and she had me completely flabbergasted. Like a man dying of thirst, I smooched her hardened, erect nipple, taking it in my mouth and sucking hungrily. My tongue traveled over the smooth, warm skin with unrestrained pleasure, exploring and savoring her taste.
“Not so fast,” she whispered, “Suck gently, my little baby…that’s it…there you go….that’s mommy’s little sissy.”
She bent down slightly and kissed my forehead softly.
All of a sudden, as I began sucking harder on her nipple--to my utter surprise--my efforts were rewarded with a thin stream of odd, albeit not unpleasant tasting milk. My eyes widened in shock as I stared at the massive melon in front of me, while Ms. Taylor looked down on me with a knowing smile.
“That’s right, my little prissy one. I’m lactating just like when you were a toddler. Only thing is—this big baby hasn’t outgrown his need for mommy’s milk.”
She emphasized her point by bracing the back of my head with her arm, preventing me from escaping. Not that I was inclined too. However, finding myself nursing from a big breast again brought back more shameful memories of my youth, that I had tried so hard to forget. My mom had breastfed me well into my fifth year, despite my father’s adamant protests to the contrary. I could still hear his angry words ringing in my ears… “If you don’t stop that--he’ll turn into a sissy!”
It looked like my dad had been right all along.
“There, there,” Ms. Taylor cooed, “Take your time, little Ethan, there’s plenty of milk for my hungry little sissy…there…that’s it…that’s my little baby…mommy’s got more than enough to fill you up…I’ve been saving this up for someone special like you….mm-hm…”
I blushed anew as she smiled down at me, her pretty face just inches from my own. Being this close to such a hottie should have made me feel very macho but in fact, I felt just the opposite. Her manner and my outfit made me feel like nothing more than a helpless little baby.
“I know just what my baby sissy wants,” she said sweetly.
While I dutifully nursed from her massive, milk-laden breast, she reached down with her free hand and began softly stroking the shiny front of my vinyl covered diapers, making me mew with ecstasy. My eyelids grew heavy as my little penis throbbed within the soft, comforting folds, caressed directly by the bunny soft cotton and indirectly by Ms. Taylor’s wonderful touch. My heart was beating wildly now, flushed with sexual excitement such as I had never experienced in my whole life!
She continued her attentions, with just enough pressure that I was kept teetering on the edge, yet not enough to bring about the powerful, explosive orgasm that I knew was just beyond reach. I lay there, sucking her big, beautiful breast as she gently and lovingly masturbated me until my breathing was starting to become difficult. Finally, unable to take the sensual torture for another minute, I reached down to provide the necessary physical stimulation myself. I was so close to cumming in the biggest orgasm of my life, I wasn’t about to let it go!
But Ms. Taylor saw what I was doing and she gently but firmly pulled my hand away, preventing me from bringing about the earth-shaking climax that I knew was only seconds away. I whimpered in protest but she only smiled down on me, holding my arm underneath me and keeping me from using it.
I looked up at her with pleading eyes but she only smiled and gently removed her breast from my mouth.
“Shhhh, little baby,” she whispered.
I whimpered like an infant as she tucked it back into the sexy lace cup of her bra although I was relieved to see her take the other one out to replace it.
“Time for the other one, Sissykins,” she said in her sultry voice.
Gratefully, I began nursing on her other beautiful mammary as she reached down and began softly stroking me again.
I had never experience such pleasure in my whole life! I wanted this moment to last forever!
It wasn’t long before I was once again, worked into a frenzy of unrequited sexual energy as she teasingly stroked the pillowy front of my comfy, silky soft diapers. My little peanut was rock hard, slick with pre-cum, and it strained against Ms. Taylor’s loving caress, hoping to blast away in a mind-numbing orgasm. Sensing how close I was, she stopped and laid her slim hand against my crotch with a feather touch.
Gasping for breath, I stopped sucking her wonderful nipple and looked up at her pleadingly.
“Please, please, Ms. Taylor,” I whined pathetically, “please let me cum.”
Ms. Taylor smiled broadly down at me and pushed her breast back against my face, practically smothering me, and preventing me from begging any further.
“Sorry little baby, that isn’t appropriate for sissies,” she told me as she beeped my nose flirtatiously with her long nailed finger.
It was so cruel! This luscious babe was preventing me from achieving the most wonderful orgasm in my youthful history and I was helpless to do anything about it!! I was beside myself with sexual excitement and frustration!
Finally, after another maddening ten minutes of nursing from her succulent boob, she pulled it away and put it back in her bra.
“That enough for now, Sissy,” she said to my utter disappointment, “I have another baby I have to attend to.”
I heard what she said but my mind couldn’t believe my ears!
It just couldn’t be possible that she was stopping, and all of a sudden, I felt like I was on the verge of tears. Sensing how upset I was, she reached down and eased my pink pacifier back between my lips.
“Aww, don’t cry, little sissy,” she said in a voice that was sweet, yet not fully sincere.
It surprised even me that my eyes were moist with the bitter tears of frustration. My heart was still racing and I refused to believe what she was doing to me.
Was this how adults really were? How could she be so cruel as to get me worked up into a lather—just to deny me satisfaction? My mind couldn’t grapple with the immensity of it.
“Come on over here and climb in the playpen so you can play with your Barbies. Don’t worry—no one will ever know—you just sit down and play as if you were by yourself—okay?” she said to me like nothing at all were the matter.
Whimpering and pouting, I waddled over to the playpen and climbed in as Ms. Taylor took the other sissified boy’s hand and helped him to climb out. For some reason, I found myself staring at his bulging, plastic covered bottom, focusing on the large, dark wet patch between his legs.
Kneeling down on the soft vinyl covered surface, I watched idly as the babyish looking boy was led over to the changing table to have his soaking wet diapers replaced. My own erection was reluctantly starting to soften and as it did, I suddenly became aware of my own very urgent need to pee. I hadn’t used the bathroom since very early this morning and since then, I had drank quite a bit of fluids. With great difficulty, I fought back against a strong urge to go that came upon me quite unexpectedly.
At the same time, the boy who had been in the playpen before me was having his clinging plastic pants pulled down by lovely Ms. Taylor. From the looks of his diapers, I could see that he’d really soaked them and they were saturated with his incontinence. Ms. Taylor hummed pleasantly as she unpinned the heavy wet cloth and dropped it into a nearby tub with a lid on it.
Gripping the soft cushioned side of the playpen rail, I strained as another flow hit me hard which I only barely prevented from escaping. I had to go pee and I had to go bad! I wasn’t sure how much longer I could hold out. I shifted on my knees, chewing the thick rubber pacifier in my mouth as I debated what to do. Ms. Taylor was busy applying diaper rash crème to the sissy on the changing table and I gazed in fascination at his slick, round little bottom cheeks, coated with a shiny white layer of the slippery stuff. I watched her place three thick diapers under his coated rump and then sprinkle a large amount of baby powder over his crotch, smoothing it up and over his chest as well.
“That’s so little sissy smells like a baby everywhere,” she commented cheerily.
I crossed my legs and barely fought back another urge as Ms. Taylor snaked a pair of yellow, lace lined plastic panties up the submissive sissy’s hairless legs.
I was just about to voice my need for the bathroom when a wall mounted telephone rang abruptly. Ms. Taylor stood up and slowly sashayed over to the opposite wall, in no particular hurry. I quickly took out my pacifier but just as I opened my mouth to say something, she picked up the phone and answered it.
“Hello?” she said in her sexy voice.
I couldn’t hear what the other person was saying but then I couldn’t think straight anyway. I was swaying back and forth now, desperately trying to keep from doing the unthinkable until my guardian got off the phone. The sissy who just had his diapers changed was now eyeing me carefully and he seemed to know exactly what was going on. He smiled back at me with a simple, childish expression and it was obvious to me that he was the sort that didn’t think twice about peeing his diapers.
“Well let’s see…” Ms. Taylor was saying carefully, “I think they are usually kept in the third drawer…”
It sounded like her conversation was nowhere near being done and I badly had to go. Whimpering to try and get her attention, I was practically dancing in the playpen but she was completely oblivious to me.
“Try the next one over…” she continued to her unnamed caller.
Suddenly, I couldn’t hold it any longer. Gripping the playpen rails until my knuckles were white, I flooded my diapers in a humiliating display of babyish helplessness. Another strong flow followed the first and I felt the warm pee saturating the front of my diapers. I choked back a sob as another, even stronger surge flowed out and soaked into the thick, thirsty cloth, surrounding me with that all too familiar, humiliating sensation. I felt like I was six years old all over again!
Holding the soft, padded railing, I felt the hot pee puddling between my legs, seeping its way back into the absorbent seat of my diapers as more continued to be released from my bladder. I half hearted tried to stop it, but by now, I knew there was no point. I relaxed as I just let it flow, feeling my diapers sag heavily from their wet weight.
Finally, at last, Ms. Taylor finished her conversation and put down the phone. She turned to go back to the sissy still on the changing table when he suddenly pointed at me accusingly.
“He just peed his diapers!” he exclaimed, in a high-pitched, weak sounding voice.
I was speechless as Ms. Taylor’s gaze turned to fix on me and then down at my heavy, sagging diapers. I was whimpering with embarrassment, not knowing what to do, as she slowly strode over and reached down, placing her delicate hand against the warm front of my diaper.
“Well, you certainly didn’t stay dry long,” she remarked pointedly, “Looks like you’re going to need to stay in diapers until we can get your mommy to pick you up.”
I could feel my face glowing red again and I swallowed hard with a sob of shame. Desperately I shook my head, devastated at the thought of my aunt learning what had transpired today. She would be so angry! First the fight, then the spanking, and now this! It was too much to bear!
Looking me in the eye with a gaze that made me wilt, Ms. Taylor put her slim hands on her curvy hips and looked down at me like I were a helpless child.
“Now…Why don’t you give me your mommy’s number…we’ll call her and have her come down and pick you up,” she said patiently.
I felt like a three year old toddler, unable to control himself and without realizing it, my eyes filled with tears.
“P-please don’t, M-Ms. Taylor,” I quaked as I took out my pacifier to speak, “P-please, I-I’ll do anything, but don’t call her.”
Without replying, Ms. Taylor turned on her heel and walked over to pick up the cordless phone from the wall. It gave me a brief opportunity to glance at her perfectly trim derriere that was wrapped in her tight skirt but I knew I was in trouble and had to concentrate. She returned with the phone and with her other hand, patted me gently on the head.
“Don’t worry Sissy, I’ll change your diapers before you go,” she assured me.
That was the farthest thing from my mind as I stared back at her, fighting back tears of humiliation.
“I know it seems unfair, but it really is for the best,” she said with her characteristic confidence, “Some little boys just aren’t ready for big boy underwear.”
I chewed my lip nervously, trying to think of a way to stall this beautiful woman but she was determined to make me submit.
“Come on now, Ethan, tell me your mommy’s phone number,” she said, her voice becoming more insistent.
Looking up into her strong, yet pretty eyes, I felt completely unable to resist her.
“I-I-I’m staying with my aunt now,” I suddenly babbled without thinking. It seemed like my words were tumbling out of my mouth like apples from a barrel, coerced by Ms. Taylor’s vastly superior will. As this hot, very adult woman stared down at me in my sopping wet diapers and Care Bears top, I felt powerless before her authority.
“Okay, what’s your auntie’s number?” she continued.
I noticed she had a tendency to couch everything in the most humiliating terms.
“B-b-but…couldn’t you…you know…couldn’t we just…I mean…” I felt like I was slipping down a slope, helpless to prevent my fall.
“Come on Sissy, give me the number,” she pressed me, “unless you’d like to take a trip over my lap for a spanking. We can do it either way.”
I gulped hard and found myself easily imagining lying face down over her sexy thighs, my wet diapers pulled back as she blistered my still sore cheeks with her paddle.
I sobbed like a baby and began blubbering the information helplessly.
“5-555-7601,” I stuttered between sobs.
Ms. Taylor dialed the number and smiled back at me, but I felt completely betrayed by this beautiful vixen. I was naively thinking that we had had some sort of special relationship and here she was, calling my aunt to tell her every shameful detail of this tumultuous day.
I prayed fervently and silently that my aunt was away from the phone but my heart sank when I heard it click as she picked it up. Holding my breath, I couldn’t make out her words but I could just discern her voice.
“Hello there. My name is Ms. Taylor from the Francis Merrimont Boy’s School. Is this Ethan Ostroff’s aunt?” I noticed her voice sounded almost imperceptibly more businesslike as she stood towering over me in her heels.
“Well it seems that your little boy picked a fight with one of the other boys and--”
I could see she was abruptly interrupted by an outburst from my aunt and my heart sank even lower.
“Yes, I’m afraid so. Well, he was taken to the principal who had to discipline him for his actions….Yes, I’m afraid so. Little Ethan got his bottom spanked for that.”
I watched as Ms. Taylor began nodding her head to something my aunt was saying.
“Mm-hm. Well, to make matters worse, he also seems to be having trouble keeping his pants dry. He wet them at lunch and I’m afraid we had to take certain….measures….”
My face was getting progressively redder as I imagined the expression on my aunt’s face.
“Mm-hm…that’s what we thought too. Yes, that’s why he’s been put back into diapers and plastic panties but I’m afraid he’s wet those too.”
I hung my head in shame as I listened to her explain my childish behavior with no means of defending myself.
“Yes, I’ll be happy to,” Ms. Taylor replied to a request I couldn’t hear, “Yes, I’m going to change his diapers right now and put him into a fresh pair.”
How mortifying that I was going to be delivered to my aunt, wearing the shameful diapers I thought I had finally put behind me.
“What’s that?” she asked, apparently surprised by some request of my aunt’s.
I watched as she looked at me and then nodded her head in agreement as some detail was explained to her.
“Oh yes, we can do that. Uh-huh…no that’s no trouble at all…mm-hm—yes we have everything here to take care of that.”
I wondered what she was talking about and my mind juggled the possibilities.
“Yes, I agree, it does help quite a bit to make sure he doesn’t mess his diapers…”
“Thank you very much Mrs. Darvin, okay, I’ll see you in about an hour then?...okay…bye-bye.”
She clicked the talk button and calmly set the phone down as if she had just been discussing gardening with a friend. Moreover, it was apparent to me that she was completely unconcerned about any consequences that might be awaiting me when my aunt took me home.
“Okay Little baby,” she said as if she had made the mistake of overestimated my maturity level, “Time to get your diapers changed.”
She reached in and helped me out of the playpen cage I had been kneeling in and took me over to the changing table where she set me down.
“You stay put and try to behave yourself—I’ll be right back,” she informed me as she strutted over to a sink by the far wall. I had no idea what she had in mind but I saw her running hot water from the tap and reaching into the cupboard for something that was blocked from view. She arranged a few items on the counter while I idly admired her sexy, voluptuous profile from my viewpoint at the changing table. My diapers were still wet and with the spongy cloth clinging to my skin, I felt extremely childish awaiting her ministrations. I watched her pour hot water and liquid soap into a large red rubber container that looked vaguely familiar to me. When the sides had fully expanded to capacity, she twisted a cap onto it and worked a long, slender white hose over the tip. Lastly, I watched as she opened a drawer and dug through it until she picked up what looked like a long rubber dildo with a large blunt head. This, she attached to the rubber tube and brought it over to me.
A glance at the other diapered sissy showed that he was looking forward to whatever Ms. Taylor had in mind for me, which only made me doubly fearful.
“Okay, Sissykins,” she said as she bent down, giving me another fabulous view of her deep cleavage, “Let’s get those wet diapers off.”
“Wh-what is that for?” I stammered as I pointed at the red rubber container.
“Hush Sissy,” she said as she began snaking down my clinging pink plastic panties.
She stopped only long enough to work my pacifier back between my lips before unpinning my wet diapers and removing them. I whimpered in shame and fear as she took a baby wipe and began cleaning the wetness from my crotch and between my legs.
“Okay Sissy, we’ve got a little extra precaution we need to take care of now,” she said as she stood up and hung the heavy rubber bag from a hook on the ceiling. Reaching down, she grasped me by the wrist and pulled me to my feet just as the side door opened. I gasped in shock as the young, attractive secretary from the other room stepped in, apparently needing something from Ms. Taylor. Once again, she stared openly at my bare crotch, fixing her gaze upon my tiny penis and giving me a look that spoke volumes about how childish she thought I was. I blushed hot red again as she finally turned to speak.
“Jennifer, are you going to be done by two?” she asked, turning back to stare at me while she waited for her answer.
My fuzzy Care Bears top hardly went past my belly button and I dropped my hands to cover my embarrassing peanut from her view.
“Yes, I’ll be done here in about an hour,” she replied as she held both my hands to turn me towards her lap. Unfortunately, this had the effect of re-exposing my diminutive genitals to the secretary’s withering gaze.
“Okay, thanks,” the she said as she looked at me one last time and wordlessly walked back out, thankfully closing the door behind her.
Ms. Taylor gently took me over her lap and once again, I found myself climbing into a face down position as I stared at her sexy high heels. I felt her cool hands grip my hips as she moved me farther forward still, until my feet were dangling off the floor behind me, leaving me helpless and unable to get down without her help.
“Wha-what are you going to do?” I whimpered uncertainly.
“This will keep you from messing your diapers,” she replied, as she applied a thick dollop of nursery jelly to my exposed rosebud, “We’re going to get you all squeaky clean for your auntie.”
I didn’t like the way this was heading but I knew better than to try and get up. My buns were still sore and burning and Ms. Taylor was definitely strong enough to hold me in place while she retrieved the paddle. I focused on the view I had of her lovely legs and heels as she spread my thighs and began rubbing something blunt and slippery against my hole.
“No…no…” I whimpered weakly as she began applying firmer pressure against it.
“Just relax, Sissy,” she said in her kindly, soothing voice, “just relax and spread your legs…it’ll go in much easier.”
I whimpered and squirmed on her lap, trying to escape the thick rubber invader but she followed my movements with the object in her hand as she gripped my hip and I felt it prying into my sphincter.
“No…Ooh!..wait—please…n-no…M-Ms. T-Taylor…” I whined pathetically as I waved my hands in helpless frustration.
Suddenly, I felt the large, semi-pliable instrument push past my hole and burrow its way deep inside as Ms. Taylor gently but firmly eased it in. I let out a cry of surprise and confusion as I tried to adjust to the strange feeling of fullness. Patting my sore bottom, she twirled the slippery invader inside me before pulling it halfway out. I moaned involuntarily and she pushed it slowly back in until it bottomed out once more. I felt so emasculated and sissyish, as she alternately slid it in and out, gently pumping my rectum in a sensuous rhythm. The warm rubber dildo began sliding past a certain nerve and I started to feel waves of erotic pleasure that I associated with forbidden sensations.
“Yes…that feels pretty good, doesn’t it Sissy,” she cooed as if she were reading my mind again.
My little penis began to harden against her bare, silky thigh and I felt my arousal returning once again.
“This is what all sissies need,” she explained as she stroked my buns while pumping me slowly with the dildo.
I was getting very excited and as she felt my stiffening wiener rubbing the soft skin of her leg, she reached down and grasped it, clamping it between her silken thighs to secure it and prevent me from moving. Now I was once again trapped, unable to accommodate my need while she was free to sexually torment me.
In my desire to maximize the pleasurable feeling coming from the dildo, I spread my legs like a cheap tart, squirming over Ms. Taylor’s lap unashamedly.
Suddenly, I heard something unclick and a surge of hot water forcefully and abruptly entered my bowels. I gasped with surprise, and I moaned again, this time in angst.
“There, there,” Ms. Taylor said soothingly, as she stroked and softly kneaded my warm buns, “That’s a good boy.”
I felt the water surging into me and very quickly, cramps began to make themselves felt.
“No…no…please…I-I can’t…take it…” I moaned in anguish.
“Shhhh,” she shushed me, “that’s a good baby.”
At last I heard her close the clip and wait as the warm soapy water settled deeper into my bowels. I was completely at her mercy, afraid to try and escape, yet desperate to get up and remove the fat rubber dildo from my rear. Occasionally, Ms. Taylor would slide it around, as if re-positioning it, but she never pulled it out more than a third of the way.
With an audible click, I heard her undo the release again and another surge flooded unrestricted into my back passage.
“Ohhhhhh…” I moaned, sounding more like a little girl than a teenager.
“Yes…” Ms. Taylor cooed, “A nice, hot soapy enema will do you a world of good…And when you’ve released the quart of water I’m giving you, we’ll put you right back into your diapers and get you dressed for your auntie.”
Tears of defeat and humiliation trickled down my cheek as I fought the forceful liquid invasion of my rump. I frantically squeezed my cheeks together but it didn’t seem to make any difference, and anyway, I could only do it for a few seconds. The fat rubber dildo did a good job of keeping my passage wide open to receive the enema. Once again, strong cramps seized my abdomen as more of the fluid gurgled into me. I gasped and moaned, flexing and unflexing my fists but I was helpless to stop Ms. Taylor’s ministrations.
Clipping it shut again, she softly stroked and squeezed my red, still burning cheeks.
“Mrs. Sterne certainly knows how to use a paddle, doesn’t she?” Ms. Taylor mused lightheartedly.
I nodded my head as my breathing deepened in response to the water that was coursing deep into my bowels. My buns were hurting but the more immediate issue was the huge volume of soapy water I was forced to retain.
“Ohhhh!...I can’t take any more, Ms. Taylor!” I complained.
“There, there Sissy,” she said softly, “We need to make sure we get you all cleaned out inside…I know it’s icky but it’s for your own good.”
I wasn’t sure how good this was but there was nothing I could do about it.
She spent the better part of twenty minutes, feeding more water into me until at long last, I heard the sound of soapy bubbles disappearing down the tube and into me. Ms. Taylor kept the fat dildo nozzle buried inside me for another minute, just to make sure, although my poor hole was starting to get rather sore from being stretched for so long.
“Okay Sissy, I’m going out pull this out and then you can go to the bathroom and release it, okay?” she asked me carefully.
“Yes—yes!” I gasped. Beads of sweat were trickling down my temple and I felt bloated and full. I needed relief in any way I could get it!
Slowly, Ms. Taylor extracted the slippery warm dildo and I felt it ease out past my sphincter. I sighed with relief and she helped me to get up onto my unsteady feet. I was pinching my cheeks together, desperate to keep the water inside until I could release it in the bathroom.
“Now don’t spill any, or Mrs. Sterne will have to re-warm that bottom of yours,” she chuckled to herself.
I nodded and limped away to the restroom which was outside and around the corner. When I finally sat down on the toilet, I practically cried with relief.
Twenty minutes later, after several flushes, I washed my hands and came out of the restroom to see Ms. Taylor waiting for me by the changing table.
“Over here, Ethan,” she called out to me.
Sheepishly, I ambled over and sat down on the table, hoping I might still convince Ms. Taylor to spare me from any further humiliation.
“Um, Ms. Taylor, I was thinking…” I began tentatively, “Do you think we could…um, maybe just…um, I mean--I was thinking, could I just wear my—you know-- regular underwear?”
Acting as if she hadn’t even heard me, Ms. Taylor retrieved a large baby bottle full of milk she had next to her and put it before my lips, trying to get me to accept it. I put up my hand to block her but she held my hand down and pushed the nipple against my lips again, even more insistently.
“No—I—please--” I stammered as I unsuccessfully tried to push it away. Ms. Taylor only smiled down on me with that look of total confidence, knowing I’d submit because of her inherent superiority.
“Oh—p-please—don’t--” just as my lips parted for a second, she pushed the big rubber nipple into my mouth, holding the bottle in place while I whimpered in defeat. Smiling with satisfaction, she waited until I was nursing a steady flow before she lifted my hand to hold it on my own.
“That’s a good baby,” she said warmly, “Some nice, warm milk while I put you back into your diapers.”
I blushed in embarrassment as I submissively did as I was told. Why didn’t I try to fight her more? I seemed completely unable to oppose her wishes as she continued to baby me.
She raised my ankles and began her tortuously sensual application of diaper rash crème to my buns. Predictably, my wiener stiffened to attention again and Ms. Taylor beamed down at me like a proud parent.
“It’s good that you like being changed,” she said as she slid a thick stack of bunny soft cloth beneath my raised rump, “Because I think you can count on wearing diapers all the time, from now on.”
Her words hit me like a splash of cold water and I realized the gravity of what she was saying. I shook my head and squealed through the nipple in my mouth although I wasn’t foolish enough to take it out.
“Mm-hm, I’ll make sure your auntie has a good supply before she leaves—that way, she’ll be able to keep you diapered and pantied outside of school too.”
Ms. Taylor seemed delighted that I would be made to look like a toddler but the thought of it made my heart beat with nervous anticipation.
After thoroughly powdering me, she pinned the thick cloth on either side and then began perusing the panty drawer for a pair she thought would be suitable.
“Here we are!” she said brightly as she held up a pair of peach colored polka dot panties, “These should be right up your alley. Aren’t they adorable?”
I cringed as she worked the noisy pair of babyish panties up my ankles and thighs, regretting the fact that the legs and waistbands were lined with soft, fuzzy ruffles. She was leaning forward, pushing her magnificent breasts in my face as she used her long nailed fingers to fit the panties into place over the fat diaper. I was about halfway finished with the bottle of warm milk when all of a sudden, I saw the door open and my aunt Alexis walked into the room unannounced.
I blushed three shades of red and jerked the bottle out of my mouth but too late for me to hope that she hadn’t seen it. She eyed me angrily, taking in my infantile Care Bears shirt, and my bowed out legs, spread wide due to the bulky diaper between them. Everything about me screamed out what a sissy I was.
“Oh—hi, Mrs. Darvin, I wasn’t expecting you for another ten minutes,” Ms. Taylor said, although she seemed secretly pleased that my aunt had caught me willingly nursing from a baby bottle.
“Ethan Ostroff! Stand up Young Man!” she ordered me sternly.
I jumped to my feet before my formidable aunt--she stood 5’ 11”-even without her usual heels, and she kept in shape by playing racquetball and water polo. I was never any match for her, physically or mentally, and truth be told—she always frightened me. Ever since I was a child, my mom had given her free reign to discipline me as she felt was necessary and I lost count of how many times I had been yanked over her knee, to get my bottom blistered with her favorite oak paddle. She thought I was weak, effeminate--pretty much a total sissy, and she had never stopped bossing me around since the day I met her.
Of course, she had been there when my mom had kept me dressed in nothing more than diapers and a t-shirt and she’d never gained an ounce of respect for me since. Ever since I could remember, aunt Alexis had always treated me like a child and I chafed from her bossy, ‘my-way-or-the-highway’ attitude. I think she believed that all of my shortcomings could be solved with a good, hard spanking—administered as often as needed.
My aunt Alexis was also quite striking for a woman of thirty-five. Maybe that was another reason that she intimidated me; with her large, thrusting breasts and proud chin, she made me feel completely inadequate in her presence. It was almost as if her beauty and femininity made me feel even less masculine and mature. I knew she had a lot of male admirers and it was obvious to see why; with a body and face like hers, she turned heads everywhere she went.
Personally, I resented her disparaging and demeaning treatment of me, although deep down, in my heart of hearts, I had to admit she was totally hot. She was hot, and believe me, she knew it. She carried that superior air of absolute confidence that no man dared cross, especially me. It hurt that she thought of me as nothing more than an immature sissy, especially when I couldn’t help myself from stealing glances at her trim, buxom figure whenever I thought she wasn’t looking.
I had been sent to her by my mom in the hopes she might be able to make me into a man and now as I stood quivering before her icy glare, it was obvious that I had failed her in every way.
I could tell by the taut expression darkening her pretty features that she was extremely angry and as she shook her head in disgust, it was apparent to her that all of her suspicions about me had been right all along.
Much as I wanted to appear as grown up and manly as possible before her, I found myself fighting back tears which I knew would only serve to make me appear more childish as I saw my plans for a fresh start going up in smoke.
Aunt Alexis brusquely crossed her arms over her very ample chest in annoyance and stared down at me, her dark, beautiful eyes flashing with anger.
“Your mother is going to be livid when she finds out about this,” she said evenly.
My mouth was suddenly dry and as I gulped hard, I found myself at a loss for words. So intimidated was I by my hot aunt, that once again, I felt weak and powerless before her. I never did have the will to stand up to her powerful persona.
I saw her staring at the half finished baby bottle still in my hands and I knew with a sinking feeling it was too late to hide it.
“If I had known you liked to drink milk from a baby’s bottle, I would have made sure your mommy dug out your baby things,” she observed dryly.
Ms. Taylor, who had thus far, remained silent, flashed her perfect smile at my aunt.
“Don’t be too hard on him;” she offered light heartedly, “Little Ethan wanted something to drink while I was changing his diapers.”
Even though I knew her statement to be untrue, I thought it best to let it go unchallenged. At this particular moment, I welcomed any support, regardless of her motivations.
“Ethan’s been a sissy all his life,” my aunt explained to her resentfully, “It took him years to get out of diapers and I always knew he’d never amount to a real man.”
“Mm-hm. I surmised as much,” Ms. Taylor agreed with a knowing smile.
My aunt turned back to face me.
“And that toddler top you’re wearing looks like it was practically made for you,” my aunt snapped at me.
I blushed hotly as I hung my head in shame.
An uncomfortable silence hung in the air until Ms. Taylor gently spoke.
“I’m sorry--I’ve completely forgotten my manners,” she confessed airily, “My name is Jennifer Taylor—I’m the principal’s assistant.”
She extended her slim, meticulously manicured hand to my aunt with a distinctly feminine bend of her wrist.
“It’s nice to meet you,” my aunt said, half smiling for the first time, “I’m Alexis Darvin—Ethan’s aunt,” she replied as she took Ms. Taylor’s hand and squeezed it in greeting.
“I’m so glad to make your acquaintance,” Ms. Taylor replied politely.
“You know—I’d be happy to let you borrow a supply of diapers and plastic panties to take with you, if you like,” she offered kindly.
“B-but I don’t need diapers—honest!” I protested adamantly.
My aunt’s hand swooped down and swatted me hard on my padded rump, making me stumble forward unexpectedly.
“I’ll be the judge of that!” she barked, “And you’d better mind your manners—you’ve already earned yourself one trip over my lap.”
Ms. Taylor stifled a giggle but I swallowed hard and without thinking, rubbed my bottom reflexively. Standing a good head taller than I, aunt Alexis was no one to be trifled with.
“I accept your gracious offer,” my aunt said, once more turning to face Ms. Taylor, “Tell me—is it difficult to find them in his size?”
“No—not if you know where to find them. We get most of our supplies off the internet from a company called Prissy’s Fashions.”
My aunt nodded appreciatively.
“I’d like the address if you can, so I can place an order of my own tonight.”
“No problem at all,” Ms. Taylor replied cheerily and she stepped over to jot down the information on a post-it note.
“And you can kiss your allowance good-bye, Ethan—I’ll be using it to pay for your new diapers,” she informed me curtly.
I withered before her as she scolded me like a five year-old child. It seemed like things were getting worse and worse with each passing moment.
Ms. Taylor handed my aunt the note and began gathering together a sizable collection of cloth diapers and plastic pants.
“Do you have any preference in the plastic panties I give you?” Ms. Taylor asked sweetly.
“The ones you’ve got on him now, look well suited for such a big sissy—have you got any more like that?”
“Oh sure,” Ms. Taylor said brightly, “I’ll pick you out some of my favorites.”
I cringed to imagine what they would be, but I remained obediently silent: I was already thinking ahead to when I would inevitably be going over aunt Alexis’s lap for my spanking tonight. I certainly didn’t want to aggravate my circumstances.
Ms. Taylor sifted through the large stuffed drawer, picking out a pair here and there, and examining each one carefully as if imagining me wearing them. I bit my lip anxiously as I watched her select pink and peach colored nursery prints, humiliatingly decorated with playful bunnies and rattles on their shiny surface. Half of the waterproof panties she picked out were lined with delicate lace or ruffles across the seat and I could only imagine how embarrassing it would be to wear them in front of my aunt.
“Thank you so much,” aunt Alexis effused.
“I’m only too happy to help little Ethan get his layette started,” Ms. Taylor beamed warmly at me.
“Well, we’d better be going, I’m sure you have other things to be doing,” my aunt offered, “Ethan, get your things together.”
“Here,” Ms. Taylor said as she came up behind me, “I’ll help you with this.”
I felt her undoing the upper buttons of my Care Bears top and to my great relief, she lifted it up and over my head. I hastened to put on my original shirt, which was draped across the bars of one of the cribs but Ms. Taylor remained holding onto my jeans.
“Oh dear—I’m afraid his pants will never fit over his diapers,” Ms. Taylor exclaimed, although her sympathy wasn’t very convincing. I think she was secretly delighted with the prospect of sending me home with my diapers fully on display for every one of my peers to see.
“I can’t go out like this!” I cried in distress.
Looking down, my diapers seemed huge, bulging out with the shiny polka dot vinyl announcing to everyone with eyes that I was nothing but a big sissy.
“You should have thought about that before you started acting like a baby!” Aunt Alexis snapped.
Observing that the issue was decided, Ms. Taylor handed my folded jeans over to my aunt.
“B-but--Aunt Alexis!” I protested.
“Would you like to go home with a pacifier in your mouth too? Because I’m this close to making it happen,” she told me firmly, “Hmm?”
Her stern, demanding eyes were too much for me to hold and I was forced to look away.
I shuffled my feet and stared at the floor.
“No, Aunt Alexis,” I mumbled under my breath.
“Good. Now go and put your shoes on—we’re going home,” she ordered me in her bossy tone.
I dragged my feet sullenly as I went over to do as I was told. Once again, my aunt had gotten her way with me and I was helpless to do anything about it. It frustrated me to no end but that’s the way it had always been, all the time I had been growing up. It was futile to argue with her and I knew better than to try.
Sitting down on the edge of the vinyl covered crib mattress, I pouted as I fussily put my shoes on. Both women were looking down on me smugly, knowing they’d won against a teenage guy and that I was definitely the inferior to either of them. I burned with resentment about my predicament.
On top of that, I couldn’t even sit normally because of the thick bulk of the diapers between my legs. I grumbled under my breath and tied my sneakers, realizing the moment I stepped outside this room, I’d make a complete fool out of myself.
Standing up, Ms. Taylor handed me the huge stack of diapers and panties to carry out to the car. I accepted them reluctantly, with my lips pursed in an expression of silent defiance.
“See you tomorrow, Ethan,” Ms. Taylor said in her syrupy sweet voice.
I mumbled something under my breath but my aunt wasn’t having it. She swatted my bottom again harshly and spun me around to face her.
“What kind of manners are those?” she demanded of me, “Now I want you to thank Ms. Taylor for graciously providing you with all those nice diapers and panties, Young Man.”
I blushed at her humiliating demand and shifted my feet, thinking this embarrassing situation would never end.
“Th-thank you, Ms. Taylor,” I mumbled in a whisper.
I saw my aunt shaking her head in dissatisfaction out of the corner of my eye.
“Boy, you really want that spanking, don’t you?” she said menacingly.
“No Aunt Alexis—please!” I pleaded.
“Then do as you’re told!”
My face burned brightly as I looked up into Ms. Taylor’s gorgeous smiling face.
“Thank you for letting me have these diapers and plastic panties, Ms. Taylor,” I said politely, my voice filled with contrition and sincerity.
Ms. Taylor bent down, putting her hands on her knees so she could be at my level which at the same time, caused her big, luscious breasts to fall forward in a breathtaking display of goddess-like femininity. I gaped at the deep line of cleavage that ran down between her soft melons where they pressed heavily against each other.
“You’re most welcome, Little Ethan,” she said as she beeped my nose, “Try to keep your diapers dry until you get home.”
I could feel my ears burning with shame as my aunt said her goodbyes and we finally left the nursery.
Stepping outside into the hallway, I suddenly felt completely exposed. My bare, skinny legs felt especially skinny, particularly compared to the fat, bulky diaper I was wearing. I also became acutely aware of just how noisy my plastic pants were. The rustle and crackle of the waterproof vinyl seemed deafening in the quiet of the hallway as I walked briskly, albeit with a pronounced waddle, out to the car. Fortunately for me, only a couple guys were anywhere to be seen but their mocking laughter rang in my ears and I couldn’t get myself hidden fast enough.
When we got outside, I felt a breeze on my nearly hairless legs and it gave me goose bumps. For two years now, ever since I went through puberty, I had been hoping that I would start to grow more hair on my body but it never seemed to have amounted to much. Rather than hair in the usual sense, most of what grew on my body was little more than peach fuzz, or in the case of my genitals, a small insubstantial shrub of light, tawny hairs. It gave me the look of perpetual childhood which only seemed to accentuate how small my penis was.
It felt very strange to have my legs so exposed when I was used to wearing pants and my faced buzzed with embarrassment from my attire. I jumped in the car as quickly as I could and tried to ignore the stares I had received from some of the faculty members in the parking lot. No doubt they found my polka dot plastic pants very amusing. I could only hope that I wouldn’t be the laughing stock of the school by tomorrow morning, but I wasn’t optimistic.
Aunt Alexis continued to scold me on the way home, berating me for starting trouble, letting my mom down, and acting like such a sissy. As was usually the case, she gave me very little opportunity to defend myself and I was forced to be the brunt for her scorn.
When at last we arrived home, aunt Alexis ordered me to take the diapers and plastic pants to my room while she went elsewhere to get something. I soon learned what it was when she showed up at the door of my bedroom with her oval wooden paddle in her hand. It was a device I had become well acquainted with as I was growing up and it never failed to fill me with terror. Having the thickness of a pancake, its oaken face had six large holes cut into it which only added to its terrific stinging power. Aunt Alexis had vast experience in using it and she unerringly brought me to tears every time I felt its wrath.
Crossing her arms again over her tremendous bosom, she towered over me as she supervised what I was doing.
“Put those on the bed,” she instructed me, referring to the big stack of diapers in my arms, “and I want you to throw out all your old underwear.”
“A-all of it?’ I asked, my voice trembling.
“Yes, all of it,” she answered curtly, “Those diapers and plastic panties will be all the underwear you need from now on.”
My shoulders sagged in defeat and I opened up the dresser drawer to begin throwing my shorts away. Suddenly, I was seized with panic as I remembered that I had hidden a pair of panties I had swiped months earlier in this same drawer. I did my best to block my aunt’s view so she wouldn’t see it but she caught me trying to slip it under a pair of my regular undies.
“--Hold it, Mister,” she said halting me, “What is that you’re trying to hide?”
She used her paddle to point at the sliver of pink material mostly hidden under the stacks of white underwear. Without pulling it out, I tried to throw the whole thing in the trash, hoping she’d forget about it in her haste to see me finish, but I had no such luck.
“Ethan Ostroff--,” she said in that cutting tone of hers that left little doubt I was in deep trouble, “Pick that out of the trash this instant.”
Her icy tone made it clear that my game was up. Filled with trepidation, I slowly bent over and retrieved the pink girl’s panties out of the trash. Why hadn’t I hidden those better? Of course, it was far too late now for recriminations or better made plans.
Holding the delicate lace panties up before aunt Alexis’s withering glare, I bowed my head low in shameful silence.
“What were those doing in your underwear drawer?” she demanded.
“Um…ah…I-I don’t know,” I stuttered.
“Young Man, you’re going to start telling the truth right now or your spanking will be twice as hard.”
I gulped hard and tried to explain their presence but nothing I could think of sounded any good.
“Um…well…I kind of, um…I sort of…I guess I got them from, um, Valerie,” I admitted haltingly, referring to my younger cousin.
Aunt Alexis faced me with her eyes blazing angrily and her arms crossing her chest as she gripped the paddle in her hands tightly.
“Well, I’m sure she’ll be delighted to find out just who stole those, don’t you think?” she said caustically, “And believe me, you are going to do just that, as soon as I’m finished paddling your sissy bottom,” she announced like a death sentence.
I was crushed and my breathing grew short as my aunt crossed over to the bed to take a seat.
“Come on,” she snapped, “I don’t think this can wait another minute.”
I whimpered helplessly as I moved over to stand next to her lap.
With sharp, angry jerks, she tugged my peach colored plastic panties down off of my bulging diapers and left them around my ankles in a tangle. I felt so childish as I stood before her, mute with shame and fear as she gripped me by the wrist and easily flung me over her lap. For the third time, I found myself face down over a woman’s knees, about to receive another punishment I hadn’t expected.
My heartbeat quickened as I felt her quickly unpin each of the bunny head safety pins holding the sides of my diapers up before she pushed the thick, bulky cloth back between my legs.
“You’ve lost a little color from your earlier spanking, Ethan, but don’t worry, I’ll make sure we get it right back,” she promised.
I sobbed with remorse and she brought her wood paddle down harshly, slapping both cheeks squarely and filling the room like a thunderclap.
My soft, tender bottom received the full impact of the paddle and I kicked my feet and burst into real tears, howling in pain as she smacked my rump again and again. Fueled by her anger and years of pent up resentment, she paddled my fanny without mercy, turning it bright red in less than a minute. She soon moved her attentions to the rosy sides of my round buns, slapping and smacking them until their color matched those of the center. I sobbed and kicked, banging my bunched up fists on the floor as she swatted my bottom in her vengeful mission of fury.
When she had finished punishing my bottom, I lay over her firm lap in a wreck, bawling my eyes out. Wordlessly, she brought the back of my diapers up and pinned them snugly into place, sealing the inferno that was blazing across my tortured cheeks. I sobbed like a baby as she lifted me up gently now, standing me on my wobbly legs as I looked into her stern, unforgiving eyes.
Still holding the paddle in her hand, she raised my polka dot plastic panties up, past my smooth thighs and began working them over the thick, bulky cotton cloth of my diapers. It seemed as if the already hot temperature on my cheeks was steadily rising as she tugged and pulled at the snug panties, using her long fingernails as she circled the elastic waistband and pulled them higher. At last, the panties were back in place and since I was still wearing my shirt and sneakers, I felt babyishly dressed and ready to resume my earlier task.
Aunt Alexis stood up and put her hands on her hips to look down on me once more.
“Finish putting these diapers and panties away and then come into my bedroom—you’ve got a phone call to make,” she told me flatly.
I sobbed and wiped the tears from my wet face as I placed the stacks of diapers into the drawer alongside the plastic pants. I was certainly not looking forward to my task, calling up my cousin and admitting I’d stolen her pink lace panties. I grumbled to myself that that was yet another piece of information that would be finding its way to my mother before long.
When I was done in the bedroom, I waddled out to find my aunt, only to discover she was in her bedroom apparently getting ready to leave. Not wishing to initiate the dreaded phone call any sooner than I had to, I stood silently, waiting for my aunt to beckon me. Purely out of habit, I gazed idly at her busty profile as she brushed her long, luxurious black hair. It was no wonder she never had a shortage of dates, I thought to myself. How many women would kill to have a body like hers…
She was wearing a snug, low cut top that displayed her deep cleavage to great effect and despite my bitterness over just being soundly paddled by her, I found myself admiring her sexy body once more against my will. I hated the fact that she turned me on, especially since she thought I was nothing but a big sissy, but I couldn’t stop myself.
“You can use the phone by the bed,” she said with an absent wave of her hairbrush without turning to look at me.
Sniffling to myself, I went over and slowly picked up the phone but I couldn’t will myself to dial it. I just didn’t have the courage to be able to tell my cousin what I’d done, but once again, aunt Alexis interceded.
Walking over, she snatched the phone out of my hands and punched in the numbers with her long nailed index finger. I chewed my lip nervously as I heard it dialing and then I recognized my cousin’s voice on the other end, indistinct, but with that characteristically youthful tone.
“Valerie? Hi honey, this is your aunt Alexis,” my aunt said cheerfully.
“Me? I’m fine how are you?” she continued.
I stood by the bed, wishing badly I could just leave and be miserable by myself but Alexis wasn’t finished with me yet.
“Say Valerie, I’m here with your cousin Ethan…you know Ethan…”
There was a pause and I sensed she didn’t have a very high opinion of me. I could only imagine what would happen when she found out what I’d done.
“Yes, well…anyway, he’s here and he has something he wants to tell you,” she said before thrusting the phone at me, “Ethan.”
I looked at the phone like it was a cobra, poised to strike me, but she pushed it into my hands impatiently.
“Tell her what you did, Ethan,” she insisted.
Taking the phone from her, I swallowed hard and put it up to my face.
“V-Valerie?” I asked tentatively into the phone piece.
Aunt Alexis stood directly before me as she waited for me to say what I’d done. A detached part of my mind noted that her big breasts were stretching her snug top so tightly that the fabric was wrinkle free as it hugged her bosom.
“Yeah, what do you want?” Valerie replied, sounding irritated with having to talk to me.
I had never been close to my eleven year-old cousin and this was certainly not going to improve our relationship.
“Um, I um…I kind of, um...well I…um….” I stammered witlessly into the phone but I just couldn’t spit out the words.
Finally, aunt Alexis, who had been watching me impatiently, stalked out of the room, only to return a moment later with the fearsome paddle in her hands again. Seeing the determined look on her face, I knew with horrible certainty that I had to tell the truth and tell it now.
“I stole your pink panties!” I blurted out.
“You what??!!” she exclaimed in her little girl voice.
“I didn’t mean it!” I cried desperately, “I was gonna give them back…honest!”
“You stole my underwear?” she cried incredulously, “How come?”
I didn’t know what to say to that…I certainly didn’t want to admit that I’d put them on and masturbated to a dizzying climax.
“Um…I don’t know…” I lied.
Perhaps Aunt Alexis realized that, at least in this instance, the truth was best avoided, because she snatched the phone out of my hands and finished the conversation with several comments about how I was “a weirdo” who wouldn’t be visiting for a long time.
After hanging up the phone, my aunt gave me a lengthy list of chores to finish before I went to bed—she was going out on a date and couldn’t be bothered with them. She also warned me of dire consequences if I failed to complete them to her satisfaction and I was forced to make numerous promises before she left.
When the door finally closed behind her, I was at last able to breath a sigh of relief. Her car drove down the street and I began doing the jobs she had set out for me but my mind gradually drifted back to the incredible events at school. In particular, I couldn’t stop thinking about Ms. Taylor.
What an unbelievable babe she was, I reflected. I had never met anyone like her in my whole life and just visualizing her again, made my wiener begin to stiffen. She was so incredibly sexy but it wasn’t just that…it was her manner that had me captivated and entranced. I had heard of love at first sight but I never really believed it until now.
I was certain that I had fallen in love with her, despite her strange tendency to treat me like a sissy. It had been the most embarrassing, humiliating experience of my life, but still…somehow I managed to overlook that aspect of her.
As I began thinking about her big, beautiful, perfect boobs, my wiener craved the attention that it had been denied for so long. Reaching down, I placed my hand on the front of my diaper, feeling the smooth vinyl plastic of my baby pants. Between them and my penis, were several layers of soft, cushiony cloth that now felt wonderful to my touch. Just as Ms. Taylor had done to me earlier, I began stroking myself in the same pleasant, teasing manner.
It felt wonderful to be able to finally masturbate without restriction and I fondled myself eagerly as my excitement level began to rise.
Truth be told, I was a chronic masturbator. Ever since I could remember, I had delighted in playing with myself and there was little that could deter me. Since I’d never been able to attract girls, naturally, I relieved my sexual needs through frequent and enthusiastic self-gratification, done whenever and however the opportunity presented itself.
I hadn’t worn a diaper for years, but now that I was, I was surprised to discover how wonderful they could be for a guy just out of puberty and discovering his own sexuality. The warm, pillowy cotton felt wonderful against my skin and I decided to take a moment and sit down on the couch to relax for a moment. However, just as my rump made contact with the sofa, I was painfully reminded of my most recent experience over my aunt’s lap and I winced in pain as I tried to block out the throbbing pain in my backside.
Nothing, however, could take away the erotic, intoxicating memories of that fantastic creature that was Ms. Taylor. What a hottie!! There just weren’t enough superlatives in the English language to truly begin to describe her adequately.
For a moment, I luxuriated in the memory of nursing at her big, succulent breasts. I couldn’t believe it had happened to me! What an amazing woman she was! She made younger girls look awkward and clumsy by comparison.
I blushed all over again as I remembered drinking the milk from her wonderful plump breasts.
I even began to wonder whether I had imagined it all, so fantastic did it seem.
As I re-lived my experience from this morning, I slowly and lavishly stroked myself through my diapers to an earth-shattering orgasm that filled them with my gooey load.
What wonderful and satisfying bliss!!
Suddenly, these diapers didn’t seem so bad after all!
I had disturbing dreams that night.
I dreamed that I was struggling to keep from wetting my pants, and I was stuck in one of those dreaded locking cribs I’d seen in the nursery at school. I shook the bars and shouted for Ms. Taylor but she only smiled at me with that look of hers as if too say, ‘too bad, sissy’…
In the end, I managed to soak my diapers and that’s when I woke up, only to realize it was just a dream. I was vastly relieved but it must have been a dream within a dream, because I woke the next morning, feeling aunt Alexis’s hand squeezing my well padded bottom. The vinyl crinkled under her hand and much to my chagrin, I felt the clammy wet cloth clinging to my buns.
“Wet again, I see,” she said in her disparaging voice. “Come on,” she said as she slapped my fanny with a dull thud, “time to change your diapers, baby boy.”
I winced with embarrassment as I rolled over and sat up. My aunt had laid out a vinyl waterproof changing mat and I eased off the bed to sit down on it.
“I guess some little boys just never outgrow their diapers, do they Ethan?” she remarked as she peeled my plastic panties down off the wet cloth. After unpinning them and putting them in a new plastic wastebasket, she began cleaning my bottom and genitals with a warm washcloth.
“Your job, when you get home from school, will be to wash your diapers and panties, understood?”
“Yes Ma’am,” I murmured.
“You may act like a baby but you’re big enough to do your own laundry,” she quipped.
I said nothing as she powdered me thoroughly with a generous dusting of baby powder.
“Oh!” I exclaimed as I tried to stop her, “Do you have to use so much?”
She stopped briefly to look me in the eye.
“What—are you worried people will smell the baby powder on you and suspect you’re back in diapers again?”
I nodded but she didn’t seem the least sympathetic towards me.
“Well that’s just too bad,” she retorted as she continued sprinkling more on me, “Maybe a little humiliation is just what you need.”
Just to make her point, she sprinkled some more on my chest and smoothed it around, ensuring I’d smell like a baby’s nursery when I got to school. Continuing with her task, she pulled the thick layers of cloth between my legs and pinned them up on either side. I could feel their soft bulk and I knew they would be next to impossible to hide.
“Can’t I go with a thinner diaper?” I complained bitterly.
“Big babies need big diapers,” she said simply as she selected a pair of plastic pants for me to wear. Gathering the legs holes in her hands, she pulled them over my feet and snaked them down my bare legs, working them over the cushiony cloth until they completely covered the fat diaper. Lastly, she powdered between my legs before she slapped me on my thick, vinyl covered fanny.
“There, you’re all set. Why don’t you finish getting ready for school,” she told me.
I looked down depressingly at the white nursery print pattern on the shiny plastic pants that enveloped my diaper, realizing I had very little chance of hiding the bulk no matter what clothes I chose. As my aunt walked out of the room, I got up and stepped over to the closet to see what I could find. As I scanned my available wardrobe, my hand naturally went down to touch my penis, except that now it was covered in layers of bunny soft cotton.
I stopped for a moment to reflect back on yesterday’s incredible events and my mind once again drifted back to Ms. Taylor. Had all that really happened, I wondered. She was so fantastic…I wondered if I would be seeing her again today. I was so infatuated with her and as I remembered the pleasant memories of nursing from her tremendous breasts, my wiener began rising up within my soft diapers. I stroked the smooth outside with my hand and reveled in the wonderful sensation it provided.
This was something I had to take care of right now!
Sitting on the bed, I spread my legs and began masturbating in earnest. My wonderfully soft, thick diapers felt like heaven as I fondled and rubbed myself into another eye-crossing climax that left me breathless.
Ahhhh… what delicious pleasure that was!
As my erection faded, I became acutely aware again of wearing something designed for an infant and I blushed to myself. How many other boys had worn these plastic pants and wet in them, I wondered ashamed. Finally, I picked out a t-shirt and overalls that I hoped were baggy enough, praying that no one would notice what I had on underneath.
Arriving at school, I went with the assumption that no one was aware of my change of clothing and I went to find my class. I had to be careful how I walked because the bulk of my diapers were so thick, it forced me to walk with a very babyish waddle.
I wasn’t late, but I ended up being one of the last to take my seat at the back. I was consciously aware of the distinct smell of baby powder that surrounded me and I tried to hide my blushing, praying that no one else could detect it. I got several strange looks from people but I did my best to look the other way and hope they wouldn’t ask me about my peculiar scent.
My teacher had her face down, working on some papers and she didn’t actually look up until the bell rang. At that point, as she scanned the room, her gaze fell upon me and she pointed her pen in my direction.
“Mr. Ostroff—what are you doing here?” she demanded, using that cutting voice that rent the air like a dentist’s drill.
I swallowed hard, completely unprepared for that kind of question.
“Um…I thought…I guess ‘cause…this is my class,” my voice trailed off uncertainly.
“Not anymore,” she snapped, “You were supposed to report to the Nursery today.”
My face burned hotly as everyone turned around to look at me, squirming in my seat.
“Umm, well couldn’t I just—you know—stay here?” I asked innocently.
“No you certainly may not,” she replied curtly, “Come up to my desk.”
My heart sank as I anticipated yet another caning or worse, at this strict, unforgiving woman’s hands. Slowly, I rose from my seat and trudged between the desks to the front of the class. I could swear I heard the word ‘diapers’ being whispered under people’s breath as I went past them and I feared my overalls hadn’t hidden what I was wearing very well after all.
Ms. Franklin stood up and looked down at me sternly as I slouched before her.
“This is the second time you’ve disrupted my class in two days,” she scolded me, “And I don’t think you’ll be needing those where you’re going.”
To my horror, she reached forward and unbuttoned the two large buttons holding up the front of my overalls, threatening to let them drop. My hands quickly went up to prevent her from doing it but she bent down and whispered into my ear. “How would you like me to tell the class here that you had to be breastfed like a baby from Ms. Taylor?”
I stared into her challenging eyes and I knew she could see the fear that was in my own.
“No!” I whispered back urgently, “Please! Please, Ms. Franklin, don’t say that!”
I was frantically desperate to keep that a secret and I was mortified to see that someone else already knew about it. What must she think of me?
“Very well,” she said evenly, “but your overalls will be staying here.”
I choked back a sob as she pulled the bib from my hands and let it drop. Because of the bulging thickness around my hips, the overalls were held up at that point, but Ms. Franklin bent down to push the denim jean material past it. As my shiny white nursery print plastic pants and fat diapers came into view, the classroom let out a collective gasp, followed by numerous giggles and barely restrained amusement. She worked my feet out of the legs of the overalls and after folding them up, placed them on her desk. While I remained facing forward crushed in shame, Ms. Franklin reached down and depressed a button on her desk mounted intercom to signal a different part of the school.
“Mrs. Sterne?”
“Mrs. Sterne here,” came the crisp, businesslike reply.
“I have one of your babies here, Ethan Ostroff.”
My face was crimson red and I felt my ears burning like they were on fire.
“I’ll send Sarah down immediately,” she informed her and ended the connection.
“You may sit by the door,” Ms. Franklin told me, pointing to a chair that seemed terribly exposed before everyone. Tears of shame filled my eyes as I waddled over and slumped into the chair, feeling the eyes of everyone on me while I stared at the floor. It was all so unfair!
It seemed like an eternity but it was probably only ten minutes before the door opened and the female secretary I had seen from yesterday came in.
I hadn’t really looked at her before but now that she was standing before me, I realized she was quite a looker. She had long, silky blonde hair that framed her young, pretty face. Very full lips and perfect skin made her look like a model. She wore a simple, pink colored blouse but I was astounded by how stretched it was from her big curvy breasts. There must be something in the water of this town, I reflected in amazement.
She wore a thin, clinging skirt that hugged her sexy hips and fanny and I couldn’t help but notice her tall high heels that accentuated her long legs.
“Hi Sarah,” Ms. Franklin greeted her politely, “Mr. Ostroff here thought he’d try and get out of his nursery time.”
“I see,” Sarah said as she looked me over for the first time today, “Mrs. Sterne will want to have a word with you, I’m afraid.”
My mouth dropped open in fear as I looked up this sexy young woman addressing me directly. I could only imagine what kind of “word” Mrs. Sterne would want to have with me.
“Come along now, you’re late as it is,” she chided me.
I stood up and waddled out of the room as she took my hand in hers like I were a child.
As we walked down the hall toward the principal’s office, Sarah could tell I was visibly upset and barely able to hold back my tears.
“Don’t you worry about a thing, Sissykins,” she said sweetly, “Everything’s going to be just fine.”
“S-so, she-she’s not going to spank me then?” I quaked.
“Oh yes, Sissy,” she said brightly, “She’ll be pulling those cute baby panties of yours down to give you a blistering spanking. But its okay, a good cry always does a sissy good.”
The way she said it, made it sound like it was the most wonderful thing in the world but I could attest to the fact that it was anything but!
My plastic pants crinkled noisily in the hall and felt hot tears trickling down my cheeks.
“I don’t want a spanking,” I sobbed sadly.
“Aww, come here,” she said as she turned to face me. Pulling me into her arms, she hugged my wet face to her soft chest as she whispered comforting sounds into my ears. Her efforts failed to alleviate my fears however and all of a sudden, I felt a strong surge of pee flow into my waiting diapers. I sobbed again as she mashed my face against her big breasts, just as another stream flowed unchecked to soak the cloth around my crotch. I felt like such a baby, helplessly wetting myself, as Sarah patted me on my head and told me to come inside.
We were standing outside the principal’s office and I waddled in, in a state of misery. Mrs. Sterne was at her desk in the room beyond, apparently busy talking on the phone and she motioned Sarah to keep me outside until she was done. Closing the door between the rooms, Sarah took me over to sit on a couch that was against the far wall. After making herself comfortable, she patted the cushion next to her bidding me to take a seat.
“You poor thing,” she said sweetly as she took me in her arms and brought me next to cuddle with her, “I know just the thing to help soothe you.”
With that, much to my surprise, she began unbuttoning her straining blouse very slowly. I stopped crying for a moment as I gaped at the two huge breasts she was revealing as she progressively opened her blouse further and further. However, now that my mind was distracted, one last strong surge of pee flooded into my diapers, thoroughly soaking them. I knew Sarah could hear it because she looked down at my shiny white nursery print panties and gave me a knowing smile.
“Its okay, Baby,” she assured me, “Everyone knows you can’t help it.” She patted the warm front of my diapers in a comforting manner but I blushed furiously at my childish lack of control.
“Here you go, Sissy,” she said as she gently lifted one of her huge boobs out of the sheer cup of her bra.
Instantly, my wiener began to stiffen and I eyed her massive melon hungrily. Pulling my head to her breast, she placed her warm, pink nipple in my mouth and began shushing my babyish whimpering.
I sucked eagerly but she stopped me with a warning.
“No, no, Sissykins,” she chided me, “You can lick it and have the nipple in your mouth but no sucking—understood?”
I squealed in protest and looked up into her pretty smiling face but she was wagging her finger at my nose. Obediently I stopped sucking and instead rolled my tongue around the warm, succulent skin of her breast, savoring the sensation. My penis was so hard it hurt and I longed desperately to stroke it as I had earlier but I knew Sarah would never sanction it.
“That’s it, Baby…that’s my little baby boy,” she cooed soothingly.
It felt strange to have my mouth filled with a huge tit and yet not be able to suck it and I chafed at being so completely controlled.
She pulled her breast out of my mouth causing me to let out a cry of despair but then, much to my relief, she placed it back in.
“There you are, Sissy,” she said with a teasing smile.
I could tell that she only intended to play with me, teasing me with her big, beautiful mammary but I was too enthralled to mind. Her pink nipple had become erect and I kissed it several times as she continued to taunt me with it, placing her breast against my lips before removing it again with a mischievous grin.
“Kiss it softly, baby Ethan,” she instructed me.
I did as I was told and I wanted to reach up and squeeze her swollen round boob but she stopped me before I could touch it.
“No, no, Sissy, you can only touch it with your mouth, no hands allowed.”
I frowned but gladly accepted her nipple back in my mouth with an unspoken agreement to behave myself. I felt like a helpless baby, unable to satisfy even my most basic desires, the way she was manipulating me.
My little member was also straining against the warm, wet cloth of my diapers and wishing there were some way it could get enough friction that would allow me to cum. My tiny balls had more than enough built up and I knew it wouldn’t take much to ejaculate one more time this morning.
However, just then, Mrs. Sterne’s door opened abruptly and she strode out of her office to witness what I was doing.
“My, my, my,” she said, her obvious disapproval written all over her pretty face, “Looks like our little sissy is still breastfeeding like a baby.”
Sarah pulled her breast out of my mouth which remained open in shock like a garage door.
“You’re even more childish than I gave you credit for,” she said dismissively as she shook her head.
My face reddened again and I clamped my mouth shut as I stared down at the ground in shame.
“Time for your spanking, Ethan!” Sarah said merrily as she tucked her heavy breast carefully back into her bra.
I let out a cry of anguish as she quickly buttoned her blouse and made herself presentable. Her beautiful melons were once again hidden from view although I could easily make out the outline of her sheer white bra as it pressed against the thin fabric of her straining top.
I was flustered and sexually confused and with my head still spinning, she led me by the hand into Mrs. Sterne’s office. Our principal led the way and as I walked in, I saw lying atop her desk, ready for use, her terrifying wooden paddle from before. I gulped as I glanced feverishly, first from it and then up into her formidable expression. Her name certainly matched her manner and I quaked with fear now that I was standing before her again. She was wearing a very business like navy colored dress jacket over a silky cream colored top that did little to hide her fantastic bosom. Her legs were slightly apart, towering over me in her heels, as she stood in a challenging stance, glaring down at me with barely concealed wrath.
Sarah stepped out silently behind me, although she left the door slightly ajar and it occurred to me that she had some devious purpose for listening in, perhaps to enable her to better hear me being punished.
Still disoriented with my whirlwind experience with her secretary, I stared open mouthed at the enticingly long line of cleavage disappearing down the front of Mrs. Sterne’s V neck top. Seeing the object of my attentions, she slapped my face soundly, practically hard enough to make me see stars.
“OWWWW!!” I cried out.
“I didn’t bring you in here to stare at my chest,” she snapped angrily, “You’re here to get a well-deserved paddling.”
Tears filled my eyes as she took a seat in her special spanking chair and drew me closer. I noticed her short skirt climbing up her long, sexy thighs, revealing her flawlessly smooth skin but I was so frightened of what was about to happen that I wet myself one more time.
Reaching over to grasp the waistband of my plastic pants, she stopped for a moment and looked into my eyes.
“Have you wet your diapers?” she said accusingly.
By now, a large, dark wet spot could easily be seen across the front of my plastic pants, announcing my incontinence to anyone with eyes.
I nodded my head in guilt and sobbed audibly.
She sighed impatiently and then reached behind her for a vinyl pad that she placed over her lap, obviously to protect her skirt from getting wet. When that was in position, she tugged my plastic panties down past my knees before hauling me over her thighs. I was already crying openly as she unpinned my wet diapers and pulled them back to expose my tender bottom for her discipline. Taking the paddle off the desk, she gripped it firmly and without hesitation, began spanking me in earnest, re-awakening the fire that had only recently been extinguished. I bucked and kicked but my wet plastic panties were tangled around my calves, hindering my efforts. Unconcerned about my difficulties, Mrs. Sterne applied the hard wooden paddle enthusiastically, slapping my defenseless cheeks with sharp, stinging smacks. I cried loudly, unconcerned anymore about who might hear me and I slapped the floor with my hands in bitter frustration.
Suddenly, she stopped and I sense that the door had opened behind me.
“Yes, what is it Lauren?” Mrs. Sterne said to someone I couldn’t see.
Looking under her trim thighs though eyes blurred with tears, I could see another female’s legs framed in the doorway. They were slim and toned, obviously the result of frequent exercise and working out but I couldn’t see any more above her knees.
“Hi, Mrs. Sterne, I have those papers you asked for,” came the reply from a young woman.
“Very well, you can leave them on the desk,” Mrs. Sterne told her with a wave of her long paddle.
“Looks like another sissy for Ms. Taylor,” the woman said indifferently as she came around to look down at me.
I looked up to see an attractive, very trim female about 17 or 18, dressed in a sexy cheerleader’s outfit of shimmery white with pink accents. I was mortified to be seen in this position, like a naughty little toddler being punished by his babysitter. And from the expression on her face, she appeared to have little or no sympathy for a schoolboy having his bottom blistered by Mrs. Sterne.
“Quite right, and that’s exactly where he’s headed once I’m finished here,” my principal explained.
“Well—don’t let me keep you from your work,” she smirked, although to my annoyance, she made no attempt to leave the room. Obviously, she wanted to remain where she could watch me cry like a baby while my bottom was soundly spanked.
Turning her attention back to me, Mrs. Sterne lowered her head slightly to address me.
“Where were we, Sissy-boy?” she asked sarcastically.
Before I could answer, she brought her wooden paddle swooping down with a scalding slap, making me howl out as I resumed bawling. As Mrs. Sterne continued spanking me, Lauren watched me with obvious approval written all over her attractive face. At last, Mrs. Sterne finished and I lay over her lap, sobbing uncontrollably as she pulled the heavy wet cloth of my diapers up to re-pin them. I was too ashamed to do anything other than stare at the ground as my tears dripped off my face and onto the floor. Mrs. Sterne raised me up and tugged my plastic panties up around the sagging cloth while I stood there, sobbing like a baby.
“Come along now,” she said as she took my hand firmly and led me into the adjoining room of the nursery. Lauren watched me go silently and I quickly forgot about her as I saw Ms. Taylor stand up from where she was bending over the playpen that Bobby was in. Today, she was dressed in a short, snug skirt, her usual high heels, and a clinging white short sleeved top with a plunging scoop neck.
“This sissy seems to have gotten lost this morning,” Mrs. Sterne said skeptically, her paddle still in her hand.
“Aww, poor little baby,” Ms. Taylor said sympathetically as she scooped me up in her arms. As I buried my face between her two tremendous breasts, she hugged me warmly and patted my back soothingly.
“There, there, baby,” she said soothingly, “Everything’s okay now.”
My tears trickled down the deep crevasse of her cleavage as I breathed in the heavenly scent of her feminine skin and perfume.
Her hand reached down and squeezed my diapered bottom, immediately sensing my wet condition.
“Looks like mommy’s little baby needs his diaper changed,” she said to no one in particular.
“Talk to you later,” Mrs. Sterne said as she returned to her office.
Ms. Taylor led me over to the changing table where she took a baby bottle full of warm milk and eased it between my lips.
“Here you are, Sweety,” she said softly, “nurse on that while I change your pampers.”
I sobbed shamefully as I sat down gingerly on the vinyl covered table, trying to minimize the pain throbbing from my blazing bottom.
Sniffling as I sucked the rubber nipple in my mouth, I watched Ms. Taylor as she carefully took my plastic panties and diapers off, setting them in the large rubber tub used for storing them.
“My, my,” she commented as she began cleaning my stinging cheeks, “Your naughty little bottom has certainly received a lot of attention since I last saw you.”
She giggled at her own comment and proceeded to apply cool diaper rash ointment to my rear, using her soft hands to coat my punished buns. I stopped sniveling as she began working her slippery middle finger up and down my crack, teasing my rosebud each time she passed it. I sucked in my breath at this familiar pleasure and she smiled warmly down at me with that ravishing grin of hers.
“Mommy’s little baby likes that, hmm?”
I nodded my head enthusiastically and I could feel my little penis beginning to harden.
Carefully placing three thick diapers beneath me, Ms. Taylor began humming to herself as she shook baby powder over my loins, rubbing the sweet scented powder all the way up my chest. As she came down to my genitals, she shook some more in her palm and began softly stroking my tiny peanut, smiling seductively down at me as she did it. My bottom was still a raging inferno but my immediate attention shifted to the wonderful feeling that Ms. Taylor was encouraging with her sensuous efforts. Her hands were as soft as butter and with each tantalizing stroke, she sent electric shivers up my spine. My breathing shortened and my chest reddened as my excitement quickened. Gazing up at this stunning goddess, her big round boobs were practically spilling out of her low cut top and my heart began beating wildly. I could just make out the delicate lace edging of her demi-cut bra as it struggled to contain her heavy, milk-laden breasts. Suddenly, I realized I was horny beyond belief and I wanted desperately to cum.
“How does my little baby like his new diapers, hmm?” she cooed down at me as she continued to gently stroke my wiener.
I nodded up and down in agreement but Ms. Taylor shook her head.
“What do you say?” she said as she stopped momentarily.
“I like my diapers,” I croaked weakly, feeling my cheeks buzz with humiliation.
“Mm-hm,” she said as she shook another handful of powder in her palm and resumed stroking my penis, “And why do you need to wear them?”
My breathing was coming in short gasps as I stared at her big, luscious melons and then into her pretty green eyes.
“B-b-because I-I’m a sissy,” I said, my face blushing red.
“That’s right, little baby,” she said with a smile, “You definitely are. And you’re not ready for big boy underwear--are you?”
“Uh-uh,” I said, my face a bright shade of red.
“Would you like me to put you in some nice, pretty plastic panties too?”
“Y-yes, Ms. Taylor,” I replied shakily. I was so worked up, I couldn’t even talk straight!
She giggled again, obviously amused at the control she could exert over me.
“I’m sure I can find something for a prissy little boy like you,” she assured me.
“And don’t you worry, Sweety,” she told me, “Because I’m going to make sure you stay in diapers and plastic panties from now on.”
I gulped at her remark but I was so taken with her sexuality that I couldn’t concentrate.
And then, without notice, she pulled the front of my diaper up and pinned either side snugly closed. My throbbing erection disappeared into the baby soft folds of my diapers, leaving me high and dry once again!
Pulling out a pair of lilac colored plastic panties, she snaked them up my skinny legs as she beamed down at my frustrated face. This woman was so unbelievably hot!
I was desperate to reach down and give myself the few strokes I needed to reach the orgasm that I was on the brink of having but Ms. Taylor seemed to sense that and she placed a rattle in my free hand. Without intending to, the rattle shook noisily in my unsteady hand, making me look even more infantile than I would have liked.
Ms. Taylor giggled musically as she ran her long nails around my elastic waistband, adjusting the waterproof panties around the bulky thickness of my diaper. My boner was still raging unrequited inside my diapers but Ms. Taylor took no more notice of it. Once again, she had brought me to the brink of a powerful orgasm, only to pull the rug out from under me at the last minute.
Removing my t-shirt, she put it aside and produced a yellow and white onesie that she pulled over my head. It was made of soft, fuzzy material that stretched over my bulging diapers as she pulled it down past my waist. I noticed a band of thick ruffles that went around my middle, hugging my waistline and serving to accentuate my diapered condition as Ms. Taylor snapped the four secure snaps at my crotch. More ruffles lined the short leg openings leaving little doubt about what I was wearing underneath. On the chest of the onesie, was a smiling pink giraffe and a lace lined bib that covered the bodice in a half circle.
I felt absolutely babyish as she pulled my shoes and socks off to replace them with white knee-high socks that looked like they belonged on a little girl. To finish me off, she buckled on shiny black leather shoes of a type I hadn’t worn since I was five years old going to Sunday school.
My outfit was both babyish and extremely sissyish and I blushed as I looked down at my bell-shaped profile.
“What a prefect ensemble for you, Ethan,” Ms. Taylor remarked brightly, as she bent down to adjust the frilly elastic around my bare thighs.
“And if I didn’t know better, I’d say you must shave your legs, they’re so soft and smooth,” she observed with an approving smile.
I blushed hotly and looked down at the light colored peach fuzz that did indeed give me the hairless look of a girl. I had always been sensitive about that aspect and it was humiliating to have her make a point of it.
“Okay, why don’t you take a seat at your desk and we’ll get things started,” she said.
Her stiletto heels clicked across the hardwood floor as she walked over to the playpen to assist Bobby who had a large pink pacifier filling his mouth. Helping him out, she sat him down at the plastic desk and seat next to me.
“Don’t worry Ethan, those chairs are made of sturdy plastic and they’re designed for heavy wetters like you that are still in diapers,” she explained as I looked at the juvenile looking desk and bowl shaped seat.
I eased myself down slowly, wincing as my stinging bottom came into contact with the hard, unforgiving surface of the seat. I noticed a number of crayons and some paper arranged neatly on the desk but I was captivated by our teacher as she took a seat directly in front of us. She had the most erotic manner about her that I couldn’t quite put my finger on but I was attuned to it nonetheless. Every movement she made seemed fluid and graceful, like a ballet dancer but it seemed as if she did it without any conscious thought. As she took her seat, she crossed her long sexy legs, putting one over the other and I sighed as her already short skirt was pulled back past the middle of her smooth, supple thighs. My gaze fell upon her heels which she dangled before her and I noticed a delicate golden chain around her ankle. I just loved her open toed sandals with the tiny straps that crossed her feet and around her curvy ankles. It was a combination both feminine and extremely sexy and I watched them as she lightly bounced her foot up and down while she spoke.
“As you both know, I am Ms. Taylor,” she began in her soft voice that was soothing yet engaging at the same time.
“This nursery is reserved for sissies like you two, and little boys who are still wetting their pants.”
As she looked directly at me, I blushed beet red and glanced away in embarrassment.
“I like to start off the day by giving those of you who are still in diapers, a nice hot, soapy enema,” she told us, “That way, we only have to worry about wet diapers, and your messes are kept to a minimum.”
I raised my hand, even as I felt my face flushed with guilt.
“Um...Ms. Taylor? What if—you know, we can go to the bathroom without doing that?” I asked hopefully.
“I don’t think so, Ethan,” she said, immediately dismissing my suggestion, “An enema does a much better job of getting you all cleaned out and then we won’t have to worry about it for the rest of the day. And I don’t want to take the chance that you might mess your diapers during your afternoon nap.”
Her confident smile made me blush anew, showing how little faith she had in my ability to control myself.
“Now, after your enemas, we’ll start with a coloring exercise in which you can show me what wonderful artists you are with your crayons.
“After that it’ll be lunchtime, followed by your afternoon nap. I’ll be checking your diapers from time to time and you’ll probably be ready for a change before I put you down in your cribs.”
I shifted nervously in my seat as I contemplated my infantile future. Looking back on it now, maybe I should have put my foot down here, while I still had the chance, but I was under the spell of this voluptuous babe that I couldn’t resist, even if I tried. And truth be told, I’m not sure I wanted to. My boner was still raging as she gently took Bobby’s hand and led him the short distance to where she had a bulging enema bag hanging from a hook in the ceiling. I watched with a mixture of dread and excitement as the little sissy had his diapers taken down and put over Ms. Taylor’s firm lap. Totally entranced, I witnessed her place a large dollop of nursery jelly at his rosebud and began sliding the big dildo nozzle back and forth, seeking out his reluctant hole. He squealed and squirmed but Ms. Taylor showed her usual persistence and soon found what she was looking for.
Pulling his round little buns apart, she pushed the soft dildo into his quivering anus and I watched as his eyes went wide. Even though by now, he had to be used to this daily procedure, it was apparent that it was still quite an ordeal for the hapless sissy. He let out a frantic moan that sounded like it came from a seven year-old girl and she soon released the clip holding back the torrent of water. Bobby gasped as he struggled to keep up with the flow but he was losing the battle. Panting from his exertions, I watched as beads of sweat appeared at his brow and tears of helplessness filled his eyes.
For some reason, I was finding this incredibly stimulating. Not only that, but Ms. Taylor was momentarily distracted and I could gaze at her incredible body while she was administering Bobby’s enema.
My hand snuck down between my legs and I began fondling my crotch over my fuzzy onesie. It felt wonderful to feel the soft, cushiony diaper caressing my wiener and my face flushed from excitement.
Bobby was struggling over Ms. Taylor’s lap, whimpering and moaning, and my gaze alternated between her two ripe melons, pushing mightily against her snug top and the sissy’s distraught face. Looking up, he caught my eye, and as he caught me masturbating, it made me blush from embarrassment. But I just couldn’t stop myself. I was transfixed watching him take his enema and my diapers felt like heaven. I was getting very close to cumming when Ms. Taylor looked up and fixed me with her stare.
“You’re up next, Ethan,” she promised with a playful wink.
I was just barely able to stop the movement of my hands before she caught me in the act. A wave of fear washed over me as I considered what was planned for me but my boner still craved attention. If only I could cum before she finished with Bobby!
I waited for her to look down at the other sissy but for the next five minutes, she alternated from checking on him to looking at me. I was prevented from bringing myself to the shattering orgasm I was so close to achieving.
All too soon, the last bubbles flowed down the tube and into Bobby’s pouting rectum and Ms. Taylor let him up to go to the bathroom. Wasting no time, she quickly refilled the red rubber bag with more soapy water and bid me to come over. Despite my apprehension of what was coming, my penis was still rock hard, although that fact was impossible to discern as it was hidden by the fat bulkiness of my diapers. This had to be one of those rare times that I was grateful I had such a tiny wiener.
I whimpered fearfully as Ms. Taylor took my hand and positioned me next to her lap. Reaching down, she undid the snaps between my legs and my onesie popped up like a spring, exposing my shiny plastic panties and diapers. I felt like a helpless baby standing before her in my sissyish outfit and I shifted nervously from foot to foot. I was nearly distracted by her warm smile and her breathtaking cleavage but I knew all too well what was about to happen next. Using her long nailed thumbs, she snaked my panties down off my diaper and took me over her sexy lap, unpinning my diapers once I was in position. I continued making weak protests as she began the tortuous act of sliding the lubricated dildo nozzle up and down my crack. I was squirming against my diaper, hoping the friction would make me cum, but also because I was trying to avoid the invasion of that fat rubber intruder.
“This is what all sissies need,” Ms. Taylor assured me as she pried my sore cheeks apart.
“N-no,” I pleaded with her but the warm, blunt end of the nozzle soon slipped inside and I moaned loudly.
“There you are, Sissy,” she cooed as she squeezed my red, stinging bun, “time for a nice, hot, soapy enema.”
“No--” I whimpered, but I was cut off as the first forceful surge gurgled into me.
I pinched my cheeks together but I couldn’t hold it for more than a few seconds and the warm soapy water flowed deep into my back passage uninterrupted.
I felt completely emasculated as Ms. Taylor held the fat, slippery dildo firmly in place, making me take the quart of water bit by inexorable bit. As the pressure built up inside me, my erection deflated and I was forced to concentrate on the cramps taking over my abdomen. I moaned and whimpered, trying to get Ms. Taylor to stop but she kept up the pace until she’d emptied the entire bag into me.
By that time, Bobby had returned from the bathroom and he watched me struggling over Ms. Taylor’s lap with a big smile in his face. I tried desperately to get up but my sexy tormentress easily held me in place. Now it was Bobby’s turn to watch a helpless, squirming boy taking his enema and he gave me a smile, not of sympathy, but of satisfaction that I was getting what I deserved.
Ms. Taylor reached down and eased a large rubber pacifier between my lips, muting my cries and whimpering and adding to my feelings of babyishness. I sucked dutifully and at last, the remainder of the enema gurgled its way inside me. I was amazed I was able to take it all and my insides felt ready to burst. Ms. Taylor gave my buns a final squeeze and after extracting the warm slippery dildo, she helped me get up on my unsteady feet.
“Run along, Sissy, you can go to the bathroom now.”
I didn’t need any encouragement and I limped off to do my business as my face buzzed with embarrassment. I had to shuffle along, mincing with difficulty as Ms. Taylor had left my plastic panties tangled around my ankles and I was too encumbered to bend over and remove them. My limp one inch peanut bounced up and down freely but I didn’t give it a thought—that is—until Sarah suddenly opened the door unexpectedly into the Nursery and stood before me, partly blocking my way.
Looking down at my bare, powdered crotch and my miniscule pee-pee, she burst into laughter, only just managing to cover her mouth as she watched me limp painfully towards the bathroom, my face burning with shame.
“Better hurry, Sissy-boy, you don’t want to leak on the floor,” she giggled.
Her mocking laughter was still ringing in my ears as I closed the door behind me, practically throwing myself onto the toilet.
Twenty minutes later, wearing a fresh diaper and seated once again at my desk, Ms. Taylor handed out sheets from a Care Bears coloring book and told us to amuse ourselves with our crayons. This activity proceeded uneventfully until an hour later when our teacher announced it was lunchtime.
Taking Bobby by the hand, she led him to a large, over-sized highchair where she sat him in place, although not before she checked his diapers.
“Looks like someone’s wearing a very wet diaper,” she commented cheerfully, but to my surprise, she made no attempt to change him. He whimpered in weak protest but Ms. Taylor merely ignored him as she began tying a plastic baby bib around his neck and securing his wrists to the sides of the tray with Velcro bands.
“Don’t worry, Baby Bobby, your diapers can still hold some more and I’ll change you before your nap, okay?” she said as she opened a couple jars of baby food and spooned it into one wide bowl.
Bobby wasn’t too happy about that and he pouted miserably as he was forced to eat the nasty slop Ms. Taylor was spoon feeding him. A fair portion of it dribbled down his chin as he struggled to keep up with her fast pace but his cries for her to slow down fell on deaf ears. Several times, he tried to move his head away, only to have Ms. Taylor come at him with another heaping spoonful and press it against his lips. He whimpered but was unable to get away or raise his hands to stop her, so long as his wrists were restrained with the straps.
I watched as my beautiful teacher upended the spoon, spilling more slop over Bobby’s chin and making an even bigger mess of his face. Bits of goop plopped down onto his bib where Ms. Taylor would scoop it up and push it back to his lips. He looked as if he were going to burst into tears but the submissive sissy could do nothing but try his best to keep up with her hurried pace.
At last, she freed one of his arms and gave him a jumbo-sized baby bottle full of milk to finish on his own.
Standing up, she took his bowl and spoon over to the sink to wash it out and I watched her pert buns through the clinging fabric of her short skirt as she sauntered away from us. She had such fantastic legs that it was sheer pleasure just ogle her sexy figure, even from a distance. After a moment, she came over to my desk and she bent down to take my hand, giving me a fabulous view down the low cut of her top.
“Come along, Ethan, its lunch time for you now,” she said sweetly.
Even though I wasn’t looking forward to a meal of disgusting baby food, I nonetheless looked forward to having Ms. Taylor pay more attention to me personally. Every time she graced me with a look, my heart palpitated and my head swam. She took my hand and led me, not to another high chair, but out to an adjoining room that I’d never been to before. My heart skipped a beat as she closed the door softly behind us and took a seat on a very comfortable couch that was one of the only pieces of furniture in the room.
The room was appointed with a very feminine feel to it, from the frilly curtains to the lace edged mirror that hung opposite the couch and I realized it allowed her to see me as I lay on her lap. The lighting was softer and less direct than in the Nursery and overall, I felt a warm sense of calm surrounding me.
“You want to know a secret?” she asked conspiratorially as she got me situated over her comforting thighs, “My breasts are literally bursting with milk, Sissykins,” she admitted, her voice taking on a seductive timbre that sent shivers down my spine.
Gently guiding me to lay down across her smooth lap, she positioned me so my face was once again poised before her bountiful bosom. My little penis began to twitch anxiously within my diapers.
“You’re such a true sissy,” she remarked as she gently stroked the side of my face with her silky hand, “that I don’t mind exposing my breasts to you.”
I was too flustered to consider the significance of her statement which seemed to imply that I was “safe” compared to other, more “macho” guys. All I could think about was getting my lips around one of her large, brown nipples. Already, I could clearly see them straining against the thin fabric of her top and bra as they poked forward insistently and noticeably. I also noticed a slight wet spot where her milk was beginning to leak through, no doubt due to the quantity she was retaining.
Taking a long nailed finger, she slowly put it under the portion of her top that went over her shoulder and eased it down, exposing the pink lacey bra strap underneath. I salivated at what I was about to experience and my little wiener eagerly sprang to attention. Not surprisingly, my heart began to beat wildly again as I gaped at her huge, delicious boobs, just inches in front of me. What a fantastic body this woman had!
Doing the same maneuver with the other side of her top, she lowered it down until her breasts were displayed before me, supported by a sexy, pink, shimmery bra. The cups embraced and held her tremendous boobs in a dazzling view of cleavage that had me literally panting with desire. Inside my diapers, my tiny wienie was straining at the soft cotton surrounding it.
“Is this what my little baby wants?” she asked in her sultry voice as she gently hefted one of them in her small hand.
“Oh, yes Ma’am!” I replied enthusiastically as I bobbed my head up and down like a woodpecker.
“Mm-hm, I thought as much,” she smiled down at me, “And I’ve got lots of milk for my little sissy-boy today.
“Know what this is?” she asked as she pointed her long immaculately manicured nail at the joining between her two cups.
I saw her pointing at a tiny clasp that enabled her to open her bra without reaching behind her. The idea excited me even more and I nodded my head in awe at her unbelievable sexuality.
“This is designed just for sissy babies like you,” she said, as if to answer her own question, “It’s for little babies who are still nursing from their mommy’s breasts.”
Her voice had taken on a subtle condescending tone, like she were addressing a three year-old instead of a teenager, but I was too captivated to care.
Pursing her lips together in a mock pout, she began speaking in a voice reserved for babies.
“Does mommy’s wittle baby want to nurse from mommy’s breast—hm?”
I gulped hard and nodded breathlessly. It was obvious that she wanted me to humiliate myself but I could smell her warm, inviting skin and her faint perfume filled my head with its delightful scent.
Using both her hands, she slowly unclipped the clasp in between her cups and partially freed her breasts from their sexy satin prison. Peeling back the pink silky material, she offered the heavy breast before my lips, daring me to take it in my mouth. It seemed like her nipple was staring me in the face, challenging me to suckle from it.
“Not yet sissy,” she chided me with her devastating smile, “First, tell me how much you like being able to dress like a sissy again.”
Her question implied that I used to dress like a sissy before but I ignored it. I wanted her boob and I wanted it bad!
“I-I like d-d-dressing like a sissy…‘cause-‘cause I get to wear soft diapers again,” I admitted shamefully. No sooner did the words come out than I blushed hotly from my ears to my chest. To speak such humiliating words while looking into the eyes of such a knockout was utterly devastating!
“Looks like someone’s blushing,” Ms. Taylor giggled as she smiled down at my reddened face, “Is it because you’re afraid of what your friends would think—if they saw you breastfeeding again in your baby diapers and sissy onesie?”
The way she put things only served to humiliate me more and my cheeks were buzzing with shame but I nodded my head anyway.
“Don’t worry, baby Ethan, because everyone knows you’re just a big sissy anyway. Your picture’s out in the hallway now, next to Bobby’s, showing everyone who’s being tutored in the Nursery. So rest assured, everyone knows all about your diapers by now.”
Her words hit me like a bucket of cold water and I felt my eyes filling with tears of frustration and shame. After everything I had done to avoid this! The last thing I wanted was for everyone to find out about my “situation”, and now, my reputation was ruined! Ruined again!!
Ms. Taylor could sense I was about to cry and she pushed her big mammary into my face, the erect nipple slipping between my quivering lips.
“There, there, baby,” she cooed down at me, “Don’t cry…don’t cry little baby.”
I sniffled in despair even as my lips embraced the warm, hard nipple filling my mouth.
“There…nurse from mommy’s boobs, that’ll make you feel better,” she assured me, “That’s mommy’s little baby.”
I felt like I had been maneuvered and trapped but I was helpless to stop her. Submissively, I sucked on her nipple and soon, a steady flow of warm milk filled my mouth. I sobbed in frustration and swallowed it, sucking desperately for more. I was so ashamed at what I had let happen to me, I felt just like the baby she was treating me like. I needed to nurse on something and her big breast gave me comfort and pacified my needs.
“There…that’s it…that’s mommy’s little baby…you drink all you need…that’s a good boy….what a good little sissy you are…”
Reaching down, she carefully undid the snaps below my crotch, exposing the smooth, shiny material of my plastic panties. Slowly, with tender, sensuous movements, she began stroking the front of my soft diapers, encouraging my nursing as she did so.
“You know, you really do belong in diapers,” she told me as she fondled them gently, “they look so appropriate on you.”
My face was still the color of an apple but I suckled away like an infant.
“From the very first moment I saw you, I knew you were really just a big baby who needed his mommy.
“And you know what I think?” she asked, even though it was impossible for me to reply, “I think you’re going to wet your diapers during your nap today….Mm-hm…I’ll bet when I come in to wake you, those pampers of yours will be soaking wet.”
I whimpered weakly as I looked up into her pretty green eyes, glittering at me like a proud mother. The light was shining on the glossy pink coating of her lipstick and despite myself and the humiliating things she was saying to me, I knew I was falling in love with her. I just couldn’t help myself. And even though I was crushed with shame, my boner had returned again and I found myself pushing my crotch against her soft, gentle movements in an attempt to make myself cum.
“There-there,” she said a little sternly as she took hold of my jaw, “Not too hard--suck gently, little baby.”
My sexual tension must have made me suck on her nipple harder and harder because I realized my jaw was getting sore. As I returned to my original pressure, her hand went back down to stroke the front of my diapers and I mewed with delight. I also found that I was starting to get full by the time she switched me over to her other breast but she insisted I finish it too.
“You’ve still got a ways to go, Sissykins,” she said with her cute wink, “This breast is bursting with milk too.”
I did my best but I couldn’t believe how full they were! I guess it stood to reason that such big, plump breasts as she had must be holding huge amounts of milk. My tummy was full and there seemed to be no end in sight!
Finally, I couldn’t take anymore and I pulled my lips away, hoping for a reprieve.
“Sorry, Sissy” she said as she placed her hand behind my head, “There’s still more to drink.”
I whimpered in protest but she forced my head forward and placed her wet, dripping, erect nipple back in my mouth. Lacking any willpower whatsoever, I submitted to her command and began nursing again, feeling very babyish. She kept her hand behind my head to prevent me from stopping but as my tummy grew fuller, I moaned in anguish. I wanted to pull away but Ms. Taylor was both bigger and stronger than I and I knew I couldn’t win against her.
“There, there, Baby,” she shushed me, “I know there’s a lot of milk there but baby has to drink it.
“And you know why? It’s because I have very, very special hormones inside me that are now going into your little tummy. They’re full of estrogen and some other big words you don’t know. And guess what…after a little while they’re going to start making you feel even more feminine than you do already.”
I looked up into her smiling face wondering what exactly her diabolical plans might be for me.
“Oh yes, and eventually, you’ll find yourself mincing around quite naturally. You’ll forget all about trying to act like a boy. So swallow it all down, Sissy-boy. Mommy’s going to turn you into her very own little sissy girl.”
I knew I shouldn’t be doing it but I swallowed more and more of her milk while she used her free hand to masturbate me through my diapers. I was completely confused and at a loss to know what to do. If what she was saying was true, I was making irrevocable changes to my own hormone balance that would eventually turn me into a swishy, effeminate sissy. But at the same time, I wanted so badly to cum that I couldn’t bear the thought of stopping my breastfeeding session.
Maybe my budding love for Ms. Taylor was also coloring my judgment. In my mind, I simply couldn’t imagine her doing anything harmful to me.
As I settled down to a troubled, confused nursing pattern with her wondrous boobs, Ms. Taylor kept up her soft, teasing stroke upon my crinkly diapers, forever keeping me on the brink but never applying hard enough pressure to actually allow me to have my orgasm.
At last, I sensed that no more milk was available and at the same time, Ms. Taylor abruptly stopped fondling my crotch.
As her big breast plopped out of my mouth, I cried out in distress.
“Oh! No…please! Please Ms. Taylor! Please let me cum!” I begged her desperately.
She smiled down at me and shook her pretty head slowly.
“Sorry Sissykins,” she said as she gently placed her big boob back into her satiny bra cup, “Its naptime for my little baby.”
From behind her back, she produced a small roll of duct tape which she used to wrap around my trembling fist that she closed with her other hand. I knew I should fight back but I couldn’t muster the courage to stand up to her. She hummed merrily as she wrapped each fist and then placed a soft pink fingerless mitten over each of them, turning them into fuzzy, useless blobs. I whimpered helplessly as I watched her efforts to prevent me from playing with myself while my little boner throbbed impotently.
“There…” she said with satisfaction and a smug smile, “That should keep my little sissy out of trouble.”
Why had I let her do this to me?? It wasn’t fair!
Tears of frustration trickled down my cheek as my stiffy began inexorably to wither away.
Reaching down between my legs, she re-snapped each of the snaps to close my onesie back in place.
“Come along, Ethan. Its naptime for you,” she said as she leaned down to face me.
I sobbed sadly as she pushed the rubber nipple of my pacifier back between my lips and led me out of the room. Bobby was still where she had left him, at his highchair, although by now, his bottle was quite empty. Ms. Taylor took me over to my crib and pulled the side rail down, sitting me upon the smooth vinyl covered surface of the mattress. She unbuckled my shiny black shoes and put them aside, pulling the soft baby blankets down as she tucked me in. She handed me a pink teddy bear and then kissed my forehead before closing the side of the crib again. Staring at her two massive breasts, now tightly wrapped in her halter top, I could scarcely believe I had just nursed from them only moments ago. But as I rolled over, I could feel all that milk sloshing around in my stomach and I wondered how I was going to hold it inside without wetting myself as Ms. Taylor had predicted.
Watching Bobby get his diapers changed, I noticed for the first time, that he had some sort of device that was covering his diminutive penis. Fascinated, I tried to get a better look but Ms. Taylor’s big boobs managed to block my view. All I could see was that he appeared to have some sort of clear plastic tube covering his wiener and I wondered what it might be.
Eventually, Ms. Taylor finished with him and put him into his crib after which she dimmed the lights in the room. I was desperately horny but with my hands restrained, I couldn’t play with myself like I did usually. I sighed loudly in frustration, defeated by the thickness of my diapers and the restraints placed upon my hands.
It was plain that until I got home, I was going to have to go without any kind of masturbation and I pouted miserably.
Restlessly, I looked through the bars of my crib to see Bobby smiling at me as he suckled upon the pink pacifier filling his mouth. He truly did look like a big baby with his girlish, curly hair and pink frilly baby dress.
My curiosity got the better of me and I began to wonder what kind of strange device it was that he had around his little package, hidden away inside his bulky diapers.
“Psst—Bobby,” I whispered, trying to keep my voice from being heard.
He removed his pacifier—somewhat reluctantly it seemed to me—and looked around furtively.
“We’re not supposed to talk during naptime,” he whispered back as if he were reciting a rule that had been drilled into him.
“What’s that thing around your wee-wee?” I asked, ignoring his warning.
“It’s a CB-3000,” he said simply, as if that explained everything.
“What’s that?” I asked again.
“It’s a chastity device…it keeps me from playing with myself.”
He seemed sad to confess it to me and I assumed he had gotten it put upon him for some past transgression. Still, I had never heard of such a thing and I was bursting with curiosity.
“How does it work?”
“It has a plastic tube, shaped like the end of my penis but smaller and that part is secured to my balls…it makes it so I can’t get hard,” he explained in a wooden tone.
“Really?” I exclaimed in astonishment, “Can’t you just take it off?”
“Uh-uh,” he shook his head, “it’s locked on and only my mom has the key.
I stared at him dumbfounded, not able to believe my ears.
“B-but…when does she unlock it?”
He hung his head sadly, “She never does.”
“Y-you mean, you’re never able to get hard?”
He shook his head again sadly.
“How do you…you know…how do you cum, then?” I asked awkwardly.
Bobby looked up at me and I was afraid he was going to start crying.
“I don’t…I haven’t had an orgasm for two years.”
My mouth hung open and I couldn’t believe what I was hearing.
“T-two years?” I gaped, “It’s not possible.”
“Uh-huh…I can’t cum cause I can’t get hard…”
I tried to imagine what it would be like to go without masturbating everyday and I couldn’t. Not for two days, certainly not for two years.
“I can’t believe it,” I said in wonderment.
He said nothing but looked down at the vinyl mattress covering of his crib. It had playful bears and giraffes on its white shiny waterproof surface, much like my own.
“Aren’t you horny?” I asked finally.
“’Course—but I can’t do anything about it…not as long as I’m locked up with this thing on.”
He seemed like such a weak sissy that part of me thought he just hadn’t given any serious thought to trying to remove it. I was certain that if I were faced with the same situation, I’d have that thing off in ten minutes. However, I didn’t say that to him.
“Did you ever…I mean…did you ever--you know--before…play with your willie?” I asked him tentatively, “-before your mom put that on you?”
“Uh-huh…I used to like to look at her Victoria’s Secret catalog and masturbate…”
I nodded my head, easily imagining my own masturbatory adventures at my aunt’s house. She always had plenty of those catalogs lying around the house since she ordering all her pretty lingerie from them. I had masturbated furiously on innumerable occasions to the glossy pictures of busty models in their exciting underthings. The mere thought of it made my penis stiff and I was suddenly glad I wasn’t under the same restriction as my room mate.
“It must be terrible not to be able to masturbate,” I acknowledged sagely.
“It is…” he agreed, “never able to satisfy any of my urges…and I think it made me even more submissive after she did it to me.”
“Really?” I asked, although it was hard for me to imagine this soft sissy in his baby dress ever being anything more than what I saw before me now.
“Uh-huh… I can’t explain it…but even my mom said it made me more…‘docile’.”
He certainly was that, I thought to myself. Although I’d seen Bobby pout, I’d never once seen him do anything even remotely defiant. It appeared that his Mom and Ms. Taylor had him absolutely controlled and the thought sent shivers down my spine. I tried to imagine the latter, her big, succulent breasts bursting out of her top, as she snapped one of those fearsome devices around my own little package. What a terrifying image!
I vowed to die before I let anyone do that to me!
Two Months later…
I was standing before Ms. Taylor as she slowly unbuttoned my shirt and removed the clothing I had worn from home. Folding them neatly, she arranged them on the table behind her while I patiently stood waiting. Gazing at her fabulous figure, I was still feeling a pleasant euphoria that came from having had another explosive orgasm in my diapers, earlier that morning.
It had become part of my morning routine. Aunt Alexis would come into my bedroom to change the diapers I’d wet during the night. While she powdered and diapered me, I’d enjoy the view of her wonderful bosom down her top, burning the image into my mind. Her big breasts jigged within her low cut tops and despite her indifference to me, they excited me constantly, never failing to get me worked up into a frenzy of sexual torment.
The second she walked out of the door, I’d sit on the edge of my bed and masturbate furiously to the view I’d just been granted, splashing my little load into the bunny soft cloth of my fresh diapers. Prior to puberty, I’d never had any idea just how wonderful diapers could be to wear until I discovered the mind-blowing orgasms possible through forbidden masturbation. I’d stroke myself, fondling the layers of soft cotton through my crinkly plastic panties until I shuddered in an eye-crossing climax that left me gasping for air. They were stupendous in their intensity! I often found myself wondering what life was like before diapers. Certainly not like this!
And now that I was wearing diapers all the time, I found myself virtually unable to stop myself from masturbating unless I were actually being prevented to do so by one of the adults. Sometimes, I would secretly rub myself in the car, or I might do it when Alexis had her back to me. Other times, I’d do it the moment my lovely teacher, Ms. Taylor stepped out of the room. It was just too tempting and the sensations too wonderful to not do it!
Yes, there were many times during the course of the day when I suffered intense humiliation, either at the hands of Ms. Taylor, or my sexy aunt, but that was just the price I was willing to pay to continue having these wonderful sexual experiences.
Twice, just last week, I had almost been caught by my aunt, after she’d changed me and left, only to return for something soon afterward. It left me in a sweat and terrified of being spanked but after the moment had passed, I soon returned to my earlier misdeeds.
I discovered that masturbation followed its own curious pattern as well. After my orgasm had subsided, I often found that minutes later, I would have to go pee very badly. Since I was still wearing my ever present diapers, this really didn’t present much of a problem and I merely let it flow while I was getting ready in the morning. Almost without fail, I’d show up at class in the nursery, wearing a soaking wet diaper which Ms. Taylor happily changed for me. This provided me with a double advantage. Any chance to get intimate attention from Ms. Taylor was not to be missed and if I didn’t wet myself from the automatic calls of nature that masturbation provided, I’d make sure I did before I got to school. So not only did wetting myself cover up any evidence of my masturbatory misadventures, it also gave me an opportunity to be closer to my idol, Ms. Taylor.
While my aunt was unrelentingly stern and condescending toward me, Ms. Taylor, by contrast, was just the opposite. Always smiling and friendly, by now I was hopelessly head over heels in love with her. She was so unbelievably sexy and pretty, there was no way it could have been otherwise. So naturally, I looked forward to every diaper change performed by her with keen excitement and anticipation. It didn’t matter that she teased me sexually and denied me any orgasms, I knew I’d get another one once I got home and could escape to the (relative) privacy of my bedroom.
I was considering that right now, as she turned back to face me wearing only my diapers before her.
“Wet already, again, Ethan?” she inquired sweetly, although I’m sure she knew the answer without asking.
“Uh-huh,” I replied with a grin, looking forward to having her big luscious melons swinging closely in front of me.
She giggled and shook her head, taking me by the hand and leading me over to the changing table. Sitting me down, she peeled off my clinging plastic panties, unpinned my heavy wet diapers and placed both items in the diaper basket, a large container with a Tupperware type of lid on it to keep the pungent smell inside.
“I’ve got a little surprise for you this weekend,” she said in a friendly manner as she began the familiar routine of rubbing diaper rash crème across my bottom.
“What’s that, Ms. Taylor?” I asked excitedly. Anything that made my teacher smile had to be good!
“How would you like to go out with me on Saturday?” she asked with a mischievous twinkle in her pretty eyes.
I gulped in incomprehension. Was I hearing correctly? Was I dreaming? I blinked hard and my mouth opened but for some reason, I found myself utterly speechless. That this knockout would consider me, a complete and total sissy, to take out on a date! How was it possible?
“Oh yes, Ms. Taylor! Yes!!” I exclaimed.
I wanted to reach up and hug her but she seemed to sense that and she plopped my pacifier into my mouth at that moment, winking playfully at me as she did. She didn’t say any more about it but I was just happy that she didn’t take back her offer.
I was filled with joy at my unbelievable luck!
The fact of the matter was, I had come to secretly enjoy my sissy life in the nursery. Wearing warm, cuddly diapers, soft, babyish clothing, and being pampered by this stunning woman was a whole new experience for me. True, I had pretty much given up the idea of ever being with a girl but now, it looked like even that had changed. Somehow, Ms. Taylor saw me for who and what I was—and she still liked me! I couldn’t believe it. Being a sissy came naturally to me but I had always denied it and tried to convince both myself and others that I was simply misunderstood. Deep down, I guess I knew I was living a lie but it took Ms. Taylor to really bring it out in the open for me to face.
And now that I was breastfeeding from her everyday, and consuming the hormones from her luscious boobs, I had started to notice a gradual but subtle change in my own body. What little hair I had on my arms, legs and crotch had all but disappeared, giving me a childish, pre-pubescent appearance. In addition, whatever tone I had once had in my muscles seemed all but gone, and my features seemed to have become softer as a result. My face was starting to look rounder and more feminine and one day when Ms. Taylor gave me a light application of make up and pink lipstick, I was astounded to see the soft, demure little girl looking back at me in the mirror.
I was glowing as Ms. Taylor slowly pulled my pink nursery print plastic panties up my smooth legs as she finished changing me. To think I would be going out on a date with her soon! I could hardly wait!
“I have a special outfit for you today, Ethan,” Ms. Taylor said as she brought over my clothing for the day. I could plainly see the white frilly lace that was used extensively on the ensemble but I blushed when she held up what looked like a prissy sailor suit top before me. Written playfully in a childish font across the bodice of it were the words: Sissy Sailor Ethan.
“Isn’t it cute?” she asked as she beamed down on me.
Instead of being dark navy in color, it was pale baby blue with white lacy accents throughout including the shamefully short hem. Short, ruffled sleeves left most of my soft, weak arms uncovered and I blushed again as she pulled it over my head. She removed my old socks and replaced them with knee length, white hose with matching baby blue silk bows across the tops. Before putting me in my shiny black shoes, she held out a pair of baby blue satiny panties, holding the elastic waistband open so I could step into them.
“Here you are, Sissykins, matching panties for my little baby,” she added gaily.
Even though I had become accustomed to wearing sissy clothes by now, my face still burned with shame as she slowly drew them up my hairless legs and spoke to me in that manner. The panties were full cut, with a wide crotch to accommodate the thick, thirsty diapers I was now used to wearing. They stretched easily as she pulled them up and over my bulging “underwear”.
“Aren’t those ruffles across the seat just precious?” she asked me.
I nodded numbly as my cheeks buzzed with embarrassment. Sometimes, the way she addressed me, it was like I was being humiliated for the first time, all over again.
Bobby and I endured our morning enemas and then spent the next hour or so practicing various feminine hairstyles on each other. I was eager for lunch to come around since I knew I’d soon be sucking from my idol’s fantastic bosom.
After Bobby got his usual feeding of baby food and warm milk, Ms. Taylor led me into her special room for breast feeders. I still blushed when I thought about the fact that most, if not all of the school faculty knew about my treatment here but I simply couldn’t resist the intimacy and intense sexuality of the act itself. It was mortifying to be known as a breastfeeding sissy but I had no willpower to stop myself as she led me—swaying her sexy hips-- into her special nursing room.
Today, Ms. Taylor was wearing a light pink sweater which did absolutely nothing to hide the fabulous shape of her big, bouncing breasts. My mouth watered as I stared at their perfect round shape, pressing urgently against the fuzzy fabric clinging to her chest.
She took her usual seat on the loveseat and sat me down next to her, unbuttoning the front of her sweater with a warm, heart stopping smile. I gaped in fascination as her two gigantic breasts slowly came into view. She was wearing a snow white bra with pink lace accents and a clasp between the two cups.
“How’s my little sissy boy, today?” she asked sweetly as she undid the clasp and pulled back a cup to reveal her heavy breast to me.
“V-very good,” I croaked anxiously. I wanted badly to get my lips around that big nipple and I felt like it had been forever since I had last suckled it, even though it was only yesterday. A small part of me realized I was getting addicted to breastfeeding, an act only babies performed, but I was helpless to my needs. My penis instantly sprang to life and I felt it straining within the soft cloth of my diapers.
“Here you are Baby,” she said as she pushed her warm nipple into my waiting mouth. I sucked eagerly and began nursing like I always did, sucking and swallowing, working at her plump breast like a real baby would. She stroked my head softly and her other hand went down to fondle the front of my cushiony diapers, making me sigh with contentment.
“Does mommy’s little baby like it when I do this?” she asked coyly.
My mouth was full of warm, wet nipple but I moaned affirmatively as I looked up into her pretty green eyes.
“Mm-hm…I thought so,” she said as she continued to softly rub the crinkly surface of my diaper, “And I’ll bet you like to do it yourself, when no one’s around, don’t you.”
I blushed hotly because it was again as if she could read my mind. What was it about her that she could know my secrets so easily?
“Come on Sissy, tell mommy the truth,” she said a little more insistently, “I’ll bet you like to play with yourself at home, don’t you?”
I shook my head but my reddening face showed the lie of it.
Suddenly, Ms. Taylor pulled her hard nipple out of my mouth, holding it temptingly before my face by no more than an inch but denying me access.
“Tell the truth, Babykins,” she said as she prevented me from nursing, “tell me all about your naughty behavior.”
I shook my head as my face burned with shame. I didn’t want to admit to her what I did every morning and night!
“Well…” she said with a note of finality, “maybe we’re done for today then...”
I felt like she’d just pulled the rug out from under me! I watched with rising panic as she gently placed her milk laden breast back in its lacy cup and closed the clasp shut.
“Noo!” I pleaded desperately, “Please don’t stop!”
She looked down at me, her big boobs still staring me in the face and taunting me with their lusciousness, as my erection gasped for relief. I could smell the delicate scent of her skin and I was frantic to resume nursing from her. I needed that nipple badly! For her to deny me would break my heart!
“I don’t know Sissy…” she said unconvinced, “I better start hearing you tell the truth.”
I gulped nervously and looked, first at the swollen flesh of her bountiful breasts, and then up into her unrelenting eyes.
“O-okay,” I stammered uncertainly, “I-I guess I…I sometimes…I guess I--um…you know…sort of, um…play a little.”
My face was burning and I couldn’t look her in the eyes anymore.
She unhooked her bra and peeled back the cup to offer me her boob again. The nipple was hard and staring me in the face and I was ready to resume suckling but she held up her finger to stop me.
“Just a lick,” she warned me.
It was torture just to take a tentative lick and be satisfied with that.
“You’re going to tell me all about what you do when no one’s around,” she said softly but firmly.
I gulped hard and tried to look away but she took her long nailed finger and brought my chin back around to face her, forcing me to look deep into her eyes. Despite her soft and warm demeanor, Ms. Taylor had a fierce determination and will when she wanted something. And I was utterly powerless to oppose her wishes.
“Go on…” she prodded me, “tell me all about it.”
I swallowed hard and my eyes dropped to her perfectly round breasts, two mouthwatering inches before my face and tempting me to drink her milk.
“I-um…I kinda play, you know…in my diapers.” I confessed shamefully.
“No, I don’t know Baby. Why don’t you tell me all about it,” She pressed me.
“Well…I get so horny…being near you…” I said trying to rationalize my deeds, “that when I get home, I have to get some kind of…you know…relief.”
“Aww, how sweet,” she said warmly, but I sensed she wasn’t entirely flattered. Was it because it was a diaper-dependant sissy who was lusting after her, rather than a real man?
“Go on…do you rub the front of your diaper, or do you put your hand down the front and stroke your wienie?” she asked directly.
I blushed anew at her pointed question.
“I rub the front of my diaper,” I admitted and I felt my ears burning hotly.
“Kiss my breast, Sissy,” she said as she brought it up to my lips.
I did so eagerly but then she pulled it away again.
“And so you masturbate through your diapers and give yourself an orgasm, is that it?”
“Uh-huh,” I said and I tried to look away but she wouldn’t let me. My face felt like it was on fire! She was so pretty and I was utterly ashamed to admit to my misdeeds while looking up at her like this.
“And how often do you do this?”
I paused, trying to gauge how much I could stretch the truth.
“Maybe…maybe once a week,” I lied.
“Ethan,” she said firmly. I could tell she was unconvinced and she made moves to re-close her bra.
“Okay, maybe several times a week,” I added quickly.
“You’d better start telling the truth or it’ll be some time before you see these again,” she warned me as she hefted each of her massive breasts in her small hands. Her actions caused her melons to be pressed together in a heart-stopping cleavage and I licked my lips with nervous anticipation as I marveled at their perfect plumpness.
“Okay, okay, I do it everyday,” I blurted out.
“Everyday?”
“Once in the morning and once when I get home, and then usually once more, before I go to bed.” I confessed in a rush.
Ms. Taylor’s mouth dropped open and I could tell even she was shocked. I suddenly realized I had made an error in telling her the whole truth.
“Three times a day?” she said incredulously, “My, my, you are a busy little boy.”
I didn’t know what to say to that so I just stared back up at her, hoping she’d drop the subject. Instead, she closed up her bra and sat me up, leaving her sweater still unbuttoned.
“Well don’t you worry, Sweety, I’ve got just the thing for you,” she said as she got up and went over to a cabinet on the wall.
I sat nervously, not sure what she meant by that but part of me was thinking maybe she’d finally do something to accommodate my considerable sexual needs. After all, wouldn’t that take care of it? If she would be willing to bring me to an orgasm everyday, I just might be able to stop masturbating, I reasoned. That had to be the answer!
Opening the cabinet, she removed something small in a pouch and brought it over to me. I couldn’t tell what was inside it but I could see it was labeled XX-SMALL on its pink velvet surface.
“I just hope this will fit you,” she said to herself and then she stopped for a moment, apparently remembering something. Standing back up, she went to a small cooler that was kept against the wall and removed some ice cubes that were in the freezer section. These, she placed in a washcloth and wrapped them up so they wouldn’t fall out. Coming back over to me, she laid both items on the sofa and turned to face me.
“Wha-what’s that?” I asked suddenly nervous, my voice breaking with tension.
“Something all sissies need,” she answered vaguely but firmly.
She reached over and grasped the elastic waistband of my silky rhumba panties, pulling them down past my knees and exposing the shiny vinyl of my diapers.
“B-but, what is it?” I asked again.
“Don’t worry Sweety, it won’t hurt a bit—I promise.”
She looked so sexy and her manner was so warm that I was tempted to relax but something inside me was sending up red flags of warning.
She peeled down my plastic panties and then unpinned my diaper, pulling the thick, soft cloth down in front of me which exposed my tiny, but erect penis.
“Hmm, just as I thought,” she said as she stared at my pencil like erection, “Okay Honey, I need you to do something for me—can you do me a little favor?”
“Uh huh,” I agreed nervously.
“I want you to place your hands underneath your little bottom and sit on them for a minute--can you do that for me? And spread you legs nice and wide.”
I didn’t like the looks of this and my lip trembled fearfully.
“B-but why?” I quaked.
“Trust me, Sissy,” she said with a wink, “And I’ll give you a big kiss.”
That eased my worrying and I placed my hands under my seat, leaving my bald crotch terribly exposed.
Taking the washcloth with the ice cubes, she brought it up against my boner, holding it an inch away.
“This may be a little uncomfortable,” she warned me in a friendly manner.
I swallowed hard and she pressed it up against my little soldier, holding it in place as she looked into my face to watch my reaction. I gasped in shock and cried out, whimpering from the coldness and pain as she continued to watch me closely. My blush wouldn’t leave me but my wee-wee was quickly defeated and it shrank down until my genitals looked like a trio of grapes on my crotch.
“There,” she smiled with satisfaction, “That’s much better.”
I didn’t know why she felt that way but after putting the washcloth aside, she spilled the contents of the pouch onto the sofa cushion next to me. I saw a number of small parts, made of some sort of strong plastic, and as she took a small ring from it, she brought it over and secured it solidly around the base of my wiener, behind my sack and against my body. It fit me snugly and I recognized immediately that there was no way I would be able to slide it past my sack with disassembling it. It had three prongs that faced forward and after placing a couple of spacers on each of them, she brought the last piece over to mate with it. This piece was made of clear plastic that closely resembled the end of a cock except it faced downward at about a 45 degree angle and it was only a little larger in size than my limp penis. Obviously, it would not be large enough to accommodate my member when it was hard, nor would it allow it to rise upward in the normal manner for an erection. I whimpered helplessly as she carefully fitted the end over my little wee-wee and positioned it against the ring, lining up its holes with the three prongs. There was just enough room for my sack to hang out from the bottom between the ring and the end piece but not anywhere near enough of a gap to allow me to pull my wiener free, even when it was limp.
“There you are, Sissy,” she said happily, “and now for the most important part.”
With that, she picked up a small titanium lock and ran it through the tiny hole that kept the diabolical device closed. With a crisp snap, she locked it closed and sat back to look at her handiwork.
“There!” she exclaimed proudly, “How does that feel?”
I flexed my wiener and I had to admit there was no pinching or discomfort.
“Uh…okay, I guess,” I mumbled worriedly.
Ms. Taylor pulled the thick cloth up of the front of my diaper and re-pinned either side, all the time beaming back at me cheerfully. As she drew my nursery plastic panties up, I stood up and let her position them over my bulky diaper. I put my hands on her shoulders for support but as I stared at her deep cleavage, my penis began to swell in the chastity device.
“Oh!” I whimpered in surprise as it quickly found the limitations of the small plastic tube.
Ms. Taylor ignored my discomfort as she slowly and teasingly pulled my satiny baby blue rhumba panties up my legs, stretching it over and around my fat diapers. When she stood up to her full height, her big breasts were once again staring me in the face, plump and glorious within her sexy bra, yet so unattainable. My wiener strained mightily against its plastic prison and I groaned in pain.
“Ms. Taylor—it hurts!” I cried out as I crossed my legs and pawed at the front of my diaper in futility.
“Aww, poor little baby,” she said and she hugged me close to her bosom. I drank in the sensation of closeness as my face was pressed against her warm, soft flesh. I closed my eyes for a moment but the pain wouldn’t go away. My penis was desperately trying to get hard but it was prevented from doing so by that devilish device! It throbbed and strained but the plastic was far too sturdy to give in. My wee-wee remained held in check, a prisoner of Ms. Taylor’s instrument of discipline and subject to her will. I felt so emasculated that she had locked up my penis and assumed control of it.
“Please…please take it off, Ms. Taylor,” I begged her piteously.
She smiled warmly down upon me and took my face in her delicate hands. My eyes were filling with tears and she bent down slowly and kissed me softly on my trembling lips.
“Hush Sissy,” she whispered in her sultry voice.
A tear trickled down my cheek but she kissed it away.
“This is what all sissies need,” she explained, “I know it will be hard at first, but eventually, you’ll come to accept it.”
Another tear tumbled down my face and she kissed me once more on my trembling lips. Her soft lips pressed against mine and I was overwhelmed by my love for her. I had to admit, being kissed so intimately by my stunning idol was almost more than I could take but I was still reeling from the concept of having my orgasms taken away.
I was practically panting when she broke her kiss with me.
“B-but, for how long?” I asked tearfully.
She answered me by giving me another kiss and then as she stood back up, she pushed my pacifier between my lips.
I was seething with frustration as she led me back in to the nursery, my mouth filled by my babyish pacifier, to place me in my crib. I was frantically horny and my penis was being held prisoner by my sexy teacher but she made no effort to allay my fears. Bobby looked at me curiously as I wiped away the tears on my face—he must have been wondering why I was crying when there hadn’t been any spanking heard.
For some reason, I was ashamed at being controlled like this and suddenly, I was desperate to keep it a secret.
“And don’t worry, Ethan,” she whispered into my ear, “you can still wet freely because there’s a slit at the end of the tube.”
With a giggle, she put me in my crib and tucked me in, raising the crib rail and latching it closed. I felt so completely helpless—more so than I’d ever felt in my life. Here I was forced to wear baby’s diapers and sissy clothes and now even my ability to relieve my sexual frustrations had been taken away. It was so unfair!
She cleaned up Bobby and after changing his diapers, put him in the crib next to me. Finally, after the lights were turned down, Ms. Taylor left us alone for our afternoon naps.
While Bobby watched me silently through the bars of his crib, I reached down the front of my diaper tentatively to try and defeat the chastity device. My first efforts weren’t encouraging and the more I tugged in it, the more I only managed to hurt myself. Obviously, it couldn’t be removed by sheer brute force. Finally, after watching me struggle in frustration, Bobby sat up and looked over the edge of his crib bars at me.
“Did Ms. Taylor put a CB-3000 on you?” he asked, having correctly guessed my predicament.
I was so upset, I couldn’t speak and I merely nodded my head as I desperately fought back the tears.
“You won’t be able to get it off,” he informed me, obviously quite sure of himself.
“I’ll get it off,” I replied shakily, although I had no idea how and my voice betrayed my uncertainty.
“I tried to too…when my mommy first put it on,” he said, feeling some sympathy towards me, “but there isn’t any way possible without the key.”
Ignoring Bobby, I tried to reach in and pull my limp penis out through the gap between the ring and the tube but there wasn’t enough room. Finally, I gave up and banged my balled fists on the crib railing in frustrated anger.
“It’s not fair!” I pouted miserably.
Bobby nodded in understanding, “The first six months are the hardest, after that, you’ll get used to not being able to cum.”
“I’ll call my mom!” I threatened, but I knew she’d only applaud Ms. Taylor’s actions.
“Sissies aren’t supposed to have orgasms,” he replied as if reading a rule from somewhere.
His submissive acceptance of the situation infuriated me and I lashed back at him angrily.
“I’m not a sissy!” I snapped, but as I looked down on the bulging diaper around my hips and the pretty lace at the waist and leg bands, I knew I was lying. Wearing a frilly sailor suit and addicted to nursing from the breast, I had to admit I was a sissy by any standards.
Bobby sighed and gave up, lying back down in his crib and pulling up his baby blankets.
Tears returned and I sobbed unashamedly. Deep down, I knew that I was sissy—a sissy who couldn’t keep his pants dry for more than two hours—but it just wasn’t fair that my ability to play with myself was being taken away! How could I get through a day without masturbation?
I sat down in a huff and angrily wiped the tears from my face. Somehow--any way I could—I had to get this thing off me. If I couldn’t break it or find a way out of it by myself, I’d beg Ms. Taylor to unlock me. After all, she obviously liked me. And she’d kissed me like a lover not ten minutes prior. There just had to be a way to convince her. There had to be!
While I drifted off to a troubled sleep, my mind began scheming of ways that I could convince Ms. Taylor to unlock me.
I woke up, feeling the thick, wet seat of my diapers being squeezed by someone.
“Looks like my little sissy wet himself again,” Ms. Taylor observed cheerfully.
For the moment, I forgot about my chastity device, that is, until my eyes took in my teacher’s big, curvy bosom that was straining at her sweater as she bent down over me. I moaned painfully as my wiener struggled again inside its implacable plastic prison.
Taking me in her arms, she hugged me closely like a baby and I savored the feeling of her immense, soft breasts mashing against my own flat chest. Lifting me out of the crib, she set my legs down on the floor and it wasn’t until I looked up that I realized another person was in the room.
“Ethan, this is Bobby’s mommy, Ms. Baker,” she said introducing me.
I blushed hotly as I became aware that my diapers were sagging heavily from all the accumulated pee. In addition, the subtle scent of stale urine surrounded me and I was ashamed to meet her hard, steely gaze.
“Nice to meet you, Ms. Baker,” I mumbled in embarrassment as I stared at the floor.
What must she think of me in my little frilly sailor suit and rhumba panties; my diaper bulging and obviously wet, I wondered.
“Looks like another sissy bedwetter, Jennifer,” she sneered dismissively.
My face burned with shame and I shifted my feet nervously.
“Well, it’s time for Ethan’s diaper change,” Ms. Taylor pointed out brightly, as she led me over to the changing table, “Would you care to assist?”
“No, I’ve got my own little baby to attend to here,” she said as she busied herself lowering Bobby’s silky panties.
“Of course,” Ms. Taylor replied and she sat me down to do the same to me.
I bit my lip nervously as she peeled my panties down, followed by my plastic baby pants. The heaviness of the wet diaper caused it to sag down my legs of its own accord, gathering around my ankles as I stood before them, nude from the waist down.
“Well,” Ms. Baker observed dryly as she stared at my hairless crotch, the CB-3000 sticking out blatantly, “looks like another sissy’s been made chaste—very good.”
Ms. Taylor giggled as she sat me down on the changing table.
“Yes, I learned that Ethan is quite a little masturbator, but we’ve taken care of that little problem, haven’t we Sweety?’ she asked me with a twinkle in her eye.
I said nothing as he began cleaning my diaper area with a damp washcloth. With all the humiliation I was suffering, my penis remained limp, that is, until Ms. Taylor began applying the diaper rash ointment to my buns. Despite the presence of a complete stranger in the room, she slid her slippery hands across my cheeks and then up and down my crack, deliberately teasing me with her efforts. I whimpered in frustration as my poor imprisoned wiener struggled to rise to the occasion, only to be denied the satisfaction.
“Little Ethan here has really come to love wearing diapers again,” Ms. Taylor explained as she slid a thick stack underneath me, “Although that may change now that he can’t play with himself any longer.”
She giggled at her own remark and Ms. Baker stared down at me coldly.
“If he were my boy, he’d find himself over my lap at least once a day,” she stated sternly, “a good paddling would do him a world of good.”
“Tell me,” Ms. Taylor asked sweetly as she pinned up my diapers, “have you ever tried breastfeeding your little boy?”
“Oh yes, he gets a regular diet of breast milk when he’s at home, don’t you Sugarplum?” she asked the abashed sissy standing next to her.
Bobby looked silly with his panties still gathered around his ankles as he stood waiting for his mommy to change him into his clothes to go home in.
“As a matter of fact, I think now is as good a time as any for a demonstration. As you may or may not know, Bobby has had a problem in the past with controlling himself. I’ve been teaching him for the last two years but I’m afraid he still hasn’t shown much improvement.”
Bobby’s face showed that he was terrified of whatever was about to happen and he pleaded with his mommy to postpone her monthly ritual.
“Please, Mommy—not here—please?” he begged her.
“Nonsense,” she snapped, “We’ll do this right now or you can go home the way you’re dressed—what’s it going to be, Mister?”
Bobby shifted nervously but he was clearly trapped.
“Not that, Mommy,” he whimpered weakly.
Ignoring his protests, Ms. Baker sat down on a chair and pulled the frail Bobby onto her lap. He began softly crying and his face was a bright red as she purposely unbuttoned her straining blouse. Ms. Baker wasn’t stunningly beautiful but she was neat and well groomed and her big breasts made for quite an impression.
“Jennifer, would you be so kind as to hand me my purse?” she asked politely.
As Ms. Taylor was doing that, Ms. Baker undid the side snaps of Bobby’s plastic panties and pulled them down. I was fascinated by what was taking place and I watched in wonder as she unpinned his diapers and pulled them back to reveal his own little cock cage. Ms. Baker reached into her purse to get a small key on a loop and a ruler. I could easily guess what the purpose of the key was but the ruler had me stumped.
Bobby was sniffling and making weak little moans of anguish but he never did anything to actually inhibit his mom’s actions. With deft movements, she unlocked his chastity device and set it aside, after which she pulled one of her massive breasts out from her bra.
“You see, Bobby was also a nasty little masturbator and he had no self discipline whatsoever,” Ms. Baker explained, “I have a little technique that I’ve developed to help him learn to behave himself.
“Are you ready, Bobby?’ she asked sternly.
“No Mommy—please!” he whined.
With a snap of her wrist, Ms. Baker brought the ruler down on Bobby’s bare thigh, making him cry out in pain.
“OWW!!” he wailed.
“What do you say, Bobby?’ she prodded him.
“M-m-may I-I please nurse, M-Mommy?” he sobbed in a quivering voice.
“Yes, you may, Sugarplum,” she said and she mashed her big, plump breast against his face.
He began eagerly nursing and I watched his red face as he shut his eyes against the humiliation of it all. Nonetheless, his body reacted predictably and I saw his tiny little wiener slowly starting to rise. Ms. Baker saw it as well and when it had reached its full extension, she slapped it soundly with a flick of her ruler.
“Naughty boy!” she barked angrily.
Bobby squealed loudly but he knew better than to take his lips off the engorged nipple in his mouth. Displaying the red welt of her ruler, his penis soon shriveled back down in ignominious retreat.
“Bobby’s learning a valuable lesson here, one that all sissies could benefit from,” she said as he regarded me severely. I shrank back in fear but remained silent. This was one matron I didn’t want to make angry with me!
“This teaches the sissy discipline,” she explained, “I’m going to teach him that I don’t allow any unauthorized erections in my household—period. We’ll do this until he’s in college if I have to.”
Tears of pain and humiliation were streaming down Bobby’s face but as he continued to nurse from the big breast in front of him, his penis was making a tentative effort to rise again. Ms. Baker stared at it, her lips set in determination, patiently waiting until it was nearly hard again. Taking careful aim, she slapped it again smartly with her ruler and this time, Bobby cried out loudly enough that he stopped nursing from his mom’s breast.
“OW-HOW-WOW!!” he howled.
“Keep nursing!” she ordered him.
Sobbing noisily, he attacked her nipple and began timidly nursing once more. In his sissy pink party dress, he looked so babyish as he nursed like an infant. I blushed as I realized that I must look very similarly when I was performing the same act with Ms. Taylor and I tried unsuccessfully to erase the image from my mind.
Bobby’s minuscule penis was deep red now, sporting the marks from two sharp attacks of his mommy’s ruler. Tears were running down his cheeks but he kept nursing dutifully at her bosom. Slowly, reluctantly, his wiener began creeping up again, as if hoping the coast was clear. However, Ms. Baker was as vigilant as a cat at mouse hole. She waited and watched until it was erect and throbbing, a crayon sized boner seeking attention.
She gave it that attention by swatting it viciously with her ruler. This time it went down and stayed down. Bobby bawled loudly and made only a superficial effort to go on nursing. He tried to assuage the pain with his hands but his mom pushed them away as she re-installed his cock lock. In moments, it was safely locked away where it couldn’t get into any more mischief on its own.
Bobby’s mom re-diapered his son and led the still sniveling sissy out of the nursery. After they left, Ms. Taylor returned her attention to me.
“Ethan, you’re aunt said she was going to be busy this afternoon and she asked if I could give you a ride home. You don’t mind do you?” she asked sweetly.
How could I deny this stunning hottie anything?
“Of course not!” I replied quickly and I waited for her to retrieve my “normal” clothes that were stacked in a neat pile on her desk.
“Good, we just need something a little more appropriate over your diapers,” she told me.
I was relieved that she was going to put my overalls back on and I moved toward them in anticipation.
“Here you are Honey,” Ms. Taylor said unexpectantly from behind me.
As I turned to face her, I saw she was holding forth a pair of frilly white rumba panties, with lilac lace around the legs and seat and a satiny bow centered on the front of the waistband.
Confused by her actions, I hesitated before her.
“B-but, why those, Ms. Taylor?” I asked.
“Your other ones were a little wet around the leg holes so I thought you might like a fresh pair,” she replied nonchalantly.
“B-but, aren’t you going to put my overalls on?” I asked as I pointed at my clothes behind me.
“These are much prettier, Ethan,” she replied, and she stepped over to stand before me.
Assuming that was the end of the discussion, Ms. Taylor bent down to hold them open for me to step into. Whimpering weakly, I obediently stepped gingerly into the panties, trying to imagine how I was going to handle going out in public dressed like a sissy baby. I steadied myself on her soft shoulders as she drew up the stretchy panties to cover my bulging diapers.
“B-but, I c-can’t go out like this,” I said with a shaky voice.
She ran her long nails around the back of my diaper as she made the last adjustments to my rumba panties.
“Its okay, Sissykins, everyone in school knows you’re in diapers again, so it won’t come as any surprise when they see you.”
I blushed hotly at the thought of that. I guess I had been in denial about my public image for months now. Still, it would be mortifying to have to walk out in my current ensemble—my diapers weren’t disguised in the least by the thin, shimmery panties I was wearing over them.
I stamped my feet in frustration as Ms. Taylor went to get some shoes for me. I was still wearing the sissyish knee socks with the blue bows on top but when she returned with her choice for me, I was in for another shock. She had in her hands, a pair of pink Keds sneakers, clearly designed for a girl.
“I can’t wear those!” I cried, although Ms. Taylor didn’t even pause as she bent down to put them on me.
“Why not, Ethan?” she asked innocently, “they’re right in your size.”
“They’re-they’re so sissyish,” I whined in a pouting voice.
“Yes they are,” she admitted, “But a sissy who wets his diapers as much as you do, can’t complain about something as silly as that.”
I whimpered in defeat as she tied the girlish shoes on my feet and then she stood up to evaluate her efforts. Standing over me, she looked down with her slim hands on her curvy hips, a broad smile on her pretty face.
“Perfect!” she exclaimed cheerfully, “You’re all ready for the Toddler Navy.”
Giggling at her remark, she grabbed her car keys and led me by the hand out of the nursery. My face burned hotly as we walked down the hallway and out to the parking lot. Several people made snickering comments about the “baby girl” or the “sissy sailor” waddling out next to the hottest teacher in school.
Somehow, I survived the interminable walk (which for me, was more of a waddle) to the parking lot and Ms. Taylor buckled me into the back seat of her BMW sedan. She looked me up and down and shook her head as she looked at her new upholstery.
“Thank god for plastic panties,” she said as she beeped me nose.
She handed me a baby bottle of milk and told me to drink up as she took her seat in front. I felt foolish, nursing from the bottle as we passed traffic on the way home. Several times, people in the cars next to us rolled down their windows to make comments on the big baby in back. All I could do was blush and stare straight ahead.
Finally, we arrived at my aunt’s house and Ms. Taylor came around to take me inside. I assumed the house would be empty but as she led me around back, I heard the voices of several adult women in the back yard. As we came around the corner, I saw that aunt Alexis had four of her friends over for a hot tub party, which explained why she hadn’t been available to pick me up.
As they turned to look at me in my baby blue sissy sailor suit and bulky diapers, I nearly wet myself in panic! I was still carrying the half empty bottle of milk and as soon as they focused on me, they all broke out in simultaneous laughter. I blushed hotly as I stood there, trying my best not to cry under the trying circumstances. Ms. Taylor reached down and patted the ruffled seat of my diapers, trying to comfort me but I was utterly mortified to be seen like this.
Alexis’s friends were much like her; hot women with trim, athletic bodies and pretty faces. They ranged in ages from about twenty to mid-thirties but every one of them was a hottie in their own right. That made it doubly humiliating to stand before them in my diapers as they made endless comments about my embarrassing attire.
They were sitting or standing around the hot tub, wearing bikinis which showed off their sexy, firm bodies to great effect. One of them, a stunning brunette named Victoria, saw me on the verge of tears and she reached over to grab me by the wrist. I stumbled over and practically fell in her lap as she began talking baby talk to me.
“Aww…who’s the big boy wearing diapers?” she asked in a childish voice as she cradled me in her arms.
“Ladies…this is Ethan, my sissy nephew that has been staying with me,” my aunt said by way of introduction.
I was afraid to meet their inquiring stares and instead I found myself gaping at Victoria’s incredible bust line, bursting out of her white string bikini top. Her breasts were rising and falling as they strained at the nearly sheer material of her swimsuit and my wiener began reacting predictably. It started swelling downward within my cock tube but within a moment, it had filled the restrictive container and could go no further. I couldn’t get erect and my wiener couldn’t become fully hard. It stayed in a frustrating state of limbo, constantly fighting against the cock cage and unable to defeat it.
I moaned weakly and it came out sounding very girlish.
“Ohh!”
“Aw, what’s the matter little sissy-boy?” she asked in mock concern.
I was hardly going to explain the reason for my outcry and instead, I maintained an embarrassed silence.
“I think I have some idea,” Ms. Taylor offered with a knowing smile, “Ethan, why don’t you tell them what you’re wearing under your diapers.”
My face went scarlet and the humiliation caused my pending erection to subside but I was ashamed to admit to what I had been forced to wear.
“What is it, Jennifer?” Victoria asked curiously.
The others looked to her in obvious interest.
“Well…” she began as she saw she had everyone’s undivided attention, “I learned today that Ethan’s quite an avid little masturbator.”
Aunt Alexis’ face darkened visibly but everyone else burst into laughter. I, on the other hand, was fighting back tears of shame as I squirmed in Victoria’s lap. I wanted nothing better than to run inside and hide from these sexy vixens but Victoria sensed it and she held me firmly in place.
“He had come to enjoy his diapers so much that he was using them to masturbate in—apparently three times a day.”
“Ewww!” one of the women, a hot blonde, cried in revulsion.
Alexis’ mouth opened in shock but she quickly recovered and she wagged her long nailed finger at me.
“You’re getting a paddling as soon as we’re done here, Young Man,” Alexis warned me.
“You’re a filthy little boy!” another exclaimed disgustedly, and I could see their mutual distaste as they stared at me, imagining my deviant activities.
“So…” Ms. Taylor continued, “Naturally, I felt it was necessary to take measures so he’d be prevented from doing it anymore—he’s wearing a CB-3000 now. You can rest assured, his masturbating days are over.”
“That’s good,” Victoria said, apparently satisfied.
The other women unanimously nodded their heads in approval.
“Yes, his cage prevents him from being able to get an erection anymore, although, for him, that may take some getting used to,” she said as she patted me on the head affectionately.
“How do you keep him from taking it off when you’re not around?” one of the bikini babes asked.
“Oh, that’s not a problem,” Ms. Taylor assured them confidently, “It’s locked securely and there’s only one key so its quite escape proof. I think Alexis should keep it for safe keeping,” she said as she turned to face my aunt.
My hopes of convincing Ms. Taylor to release me were dashed as I saw her hand the small key to aunt Alexis. I knew I’d never get her to agree to unlock me and my spirits sank like a rock.
“If I were you—I’d throw it away,” the cute blonde said as she adjusted her top to better support her big, perky breasts. She was looking at me with an obvious look of superiority on her pretty face and it was plain to see that she thought I should be kept permanently chaste.
“Yes, I think it’s disgusting that he was able to get away with masturbating in his sissy diapers for so long,” a black-haired beauty chimed in, “God only knows what he was fantasizing about.”
“Probably wearing women’s panties,” Alexis offered, “I had to blister his bottom for stealing his cousin’s only recently. As it turns out—he was stealing them so he could masturbate in them.”
The women around me were obviously shocked by that revelation.
“That is sooo nasty,” Victoria stated emphatically.
The women shook their heads in mutual disgust as they looked at the perverted panty thief before them.
My shame knew no bounds and my eyes filled with tears as I endured their disparaging taunts and then suddenly, without thinking, I began wetting myself. I no longer felt any warning when the need to pee arose and I was constantly being surprised as I felt my diapers suddenly growing wet and warm.
“Well, he can fantasize all he wants now,” Alexis pointed out, “but at least now, he won’t be able to act upon the urges anymore.”
“That’s the way it should be,” Victoria agreed sagely, “If he’s still in diapers, he can’t be ready for sexual activities.”
The women all nodded their heads in mutual agreement.
Alexis had moved to where she was standing over me, her hands upon her hips, and her big breasts thrusting out proudly within her tautly stretched bikini top. Looking up at her, I had to look between the valley created by her two massive melons to see her stern, yet gorgeous face.
“You were put in diapers because you were wetting your pants—not to give you a tool to masturbate with,” she snapped angrily.
I bit my lip nervously as I contemplated whatever punishment she had in store for me. I was also painfully aware that I was surrounded by adults who saw me as nothing more than a five year-old boy, badly in need of discipline.
“I’m tempted to file this key down,” she commented thoughtfully, “but I think maybe I’ll send it to your mother instead.”
Was I destined never to have another orgasm again? It was too terrible a fate to consider! A tear tumbled down my cheek and I sniffled miserably.
Ms. Taylor sensed my discomfort and she came over, kneeling down to look me in the eye like she would have with a child.
“Ethan? Are your diapers wet? Do you need me to change you before I go?” she asked sweetly.
I appreciated her diverting the subject and I welcomed the opportunity to leave the shameful situation I was in with these sexy, albeit condescending women.
I nodded my head, not trusting my voice since I was so close to crying. Although it was embarrassing to admit I had wet myself like a baby, I reasoned that it was the only way I’d be able to extricate myself from this humiliating scene.
“Don’t worry, Sissy,” she said as she patted me on the head lovingly, “I’ll go get your diapering supplies.”
Before I could protest, she pushed my fat rubber pacifier into my mouth and turned on her heel, strutting into the house with her characteristic sashay.
Feeling another panic induced flow of pee escaping, I tried once more to get up, but Victoria easily held me in place. She was either very strong or I had become very weak, and my efforts only made me look more childish. Finally, she slapped my bare thigh to make me stop squirming and I cried out in pain.
The women all laughed as they saw me stop struggling, defeated roundly by this buxom babe.
“Don’t you worry Baby,” she said in a thickly condescending voice, “Mommy’s gonna change those wet pampers for you.”
My face was burning hotly and I felt the wetness seeping between my legs and embracing my loins. Everyone was staring at me, amazed that a grown guy would actually wet his diapers in front of a crowd of women.
Finally, after what seemed an eternity, Ms. Taylor returned from my bedroom, where all my diapering supplies were kept. In her arms she had my nursery print changing pad, a thick stack of fresh diapers, diaper rash ointment, and baby powder. She came over to me with her usual pretty smile but she saw I was struggling to fight back the tears.
“Don’t worry, Sissy,” she said as she began carefully pulling my lacey rumba panties down, “I know it can be difficult to adjust to being a full time sissy, but you’ll get used to it soon.”
I was crying softly as she pulled down my clinging plastic baby pants and unpinned my wet diaper.
Everyone gathered around me closely to better see this young adult getting his diapers changed like an infant. As my cock cage came into view, the women all stared down at my tiny package, effectively locked away from my meddling hands.
“I probably should have put you in chastity months ago but I guess--better late than never,” Ms. Taylor reflected as she pulled the wet cotton cloth from under my seat.
“I just can’t believe it,” Victoria said as she shook her head, “He’s still wetting himself, even at this age?”
I tried to look away but everywhere I turned, a beautiful bikini-clad female was looking down at me in amazement.
Briefly, Ms. Taylor checked my CB-3000 just to make sure everything was secure before she slid the fresh, soft diapers under my upturned rump. It was devastating to be seen in this position, with my bare bottom exposed as Ms. Taylor held my ankles in the air and I braced myself awkwardly as I sniffled in shame.
“Those are some cheeks that are going to be feeling the sting of my paddle tonight,” Alexis warned me as the others giggled.
I bit my lip nervously as I imagined myself over her lap again, kicking and crying desperately as she blistered my tender fanny.
Ms. Taylor pulled up the same nursery print waterproof panties I had been wearing and I winced as I felt the wet elastic leg openings sliding back up my thighs.
“C-can’t I get some new plastic panties?” I whispered to her, although despite my efforts, everyone heard me.
“These will be fine for now, Ethan,” she said firmly, indicated the issue was decided, “You’ll just be wetting yourself in another hour.”
I pouted as I felt the cool, clammy material hugging my thighs as Ms. Taylor ran her long fingernails around the waistband to make sure the thick diaper was completely covered. Lastly, she snaked my silky rumba panties back up as I whimpered in embarrassment.
“Have a good night, Ethan, I’ll see you tomorrow, Sweety,” she said as she reached down and gave me a peck on the cheek.
I pouted in silence as she picked up her car keys and made her goodbyes to everyone present. I felt abandoned as I watched her saunter out of my pool area, leaving me alone with these hot babes who had zero respect or sympathy for me.
“Aunt Alexis, can I go now?” I asked my aunt frantically.
“Yes, run along, Ethan, I’ll deal with you later,” she told me grimly.
I quickly left and ran inside, but not without the giggles of everyone ringing in my ears. Once more, my sissyish behavior had been exposed to strangers and I re-lived the humiliation over and over in agonizing detail in my mind.
Waddling into my bedroom to try and be alone, I sat down on my bed and stared woodenly at the paddle hanging up on the wall above my dresser. I knew all too soon I’d be feeling its fearsome bite and my buns tingled at the thought of it. She’d be holding me firmly in place as she swatted my defenseless fanny again and again, making me cry harder with each harsh slap of her paddle. Why did she have to be so mean to me, I wondered for the thousandth time.
I hated myself for finding her attractive and fantasizing about her. I was bitterly ashamed to admit it, but our feelings for each other couldn’t have been more different. She thought of me as an immature, sissyish little boy, more suited to diapers and babywear than to adult clothes, whereas I thought she was like a goddess; strong, smart, successful, and extremely sexy. As I began thinking about her standing over me in her tight white bikini, my little peanut began growing hard in my cock cage again.
Determined now more than ever to remove my CB-3000, I pulled my rumba and waterproof panties down to my ankles and unpinned my diapers. I had to be quick because if aunt Alexis or one of the other women were to come in unexpectantly and catch me, I’d be sure to get spanked.
Looking closely at the device, I examined it carefully, trying to find some point of weakness but I could find none. I yanked at it harshly but the ring behind my sack made it quite impossible to get it off that way since it was far smaller in circumference than my genitals. In addition, I noticed that the three prongs were made of some kind of steel so I knew I couldn’t just break one of them off. Not to mention that even if I could, it would be noticed right away, the next time my diapers were changed. No, that wouldn’t do.
If only I could pull my penis out through the gap between the first ring and the cock tube, but there was no way. It was foolproof! Or least sissy proof, I reflected sadly. Ms. Taylor had decided to prevent me from masturbating and I could see her method was flawless. I cursed under my breath as I stared at my captive, impotent penis.
I heard the sound of giggling coming from the girls in the hot tub and I re-lived the scene that had taken place out there once again in my mind. They were so sexy in their tiny bikinis and I was awestruck at their fabulous curves. They had such perfect breasts and they were all so hot looking! Thinking about Victoria and the busty blonde made my tiny penis instantly begin to swell. I watched in mute frustration as it was forced to expand downward into the short cock tube where it quickly reached its limit.
I was so horny I could scream! What could I possibly do to get some relief??
With most of my wee-wee buried inside the cock tube, I couldn’t touch it or stroke it, and even if I could, I’d never be able to achieve an orgasm without getting fully erect. There was just no way around it! My balls were producing semen and I had no way to relieve the building pressure. What was I going to do?
I had never realized what a precious freedom I’d had to be able to masturbate every day. And now that freedom was gone forever! It was too much to bear!
Re-pinning my diapers, I stifled back a sob in my throat as I contemplated a life without orgasms, perpetually teased by the hot women that seemed to surround me constantly.
Being a creature of habit, I sneaked out to peep at the bevy of beauties talking in the hot tub and I found myself doubly frustrated. Any other time, I would have sat down unnoticed and stroked myself to a heart-pounding orgasm as I watched not only my hot aunt, but also her lovely bikini-clad girlfriends talking and unaware of my spying on them. Yet now, while I was free to drink in their curves to my heart’s delight, my crotch was in constant pain and I was denied any satisfaction whatsoever. Without thinking, and just by habit, I reached down to rub the front of my diapers but of course, now I was no longer able to feel a thing. After several fruitless minutes, I finally gave up in frustration and walked away.
Two nights later, I sat at the desk in my bedroom, working carefully on a note I intended to give to Ms. Taylor before our date. I wanted to finally tell her how I really felt about her, about my love and longing for her, and how we were destined to be together. She was everything a man could want in a woman and I thought she was perfect in every respect. Perhaps if I could just tell her that, she’d look at me in a different light.
Part of me also secretly hoped that if I told her how much I loved her, maybe she’d re-consider her decision to keep me in chastity. I was going crazy not being able to masturbate and I thought about it constantly. Every chance I got, I found myself trying to be around Aunt Alexis, even if that meant being degraded by her. My sexual desire for her hot body never went away—if anything, I felt the urge all the more acutely. And of course while I was at school, I was surrounded by the smoldering sexiness of Ms. Taylor, who was always kind to me. She hadn’t kissed me since the day she put me into the CB-3000 but she was still being flirtatious and friendly. However, breastfeeding had now become a painful proposition since I was forced to endure a budding erection that was constantly struggling to get hard but unable to do so. Of course, I begged and pleaded with her to unlock me but she only giggled and beeped my nose.
I should have been angry and resentful towards Ms. Taylor for subjecting me to such torture but for some reason, I just couldn’t. She was so pretty and nice to me and I was hopelessly in love with her. Any chance to be near her was satisfaction enough for me and one day, I hoped there could be something more between us.
I asked Aunt Alexis to provide me with some materials to write my note but all she had was some stationary and crayons. Unfortunately, it would just have to do.
I did my best to explain in the note, how much I felt about Ms. Taylor, telling her how I thought about her all the time, and how my heart ached to be with her. I even made a veiled implication that maybe she’d reconsider removing my chastity device on occasion, just in case.
At one point, Aunt Alexis came in and peered over my shoulder to see what I was writing. At first, I thought she’d only mock my efforts but I was surprised when she gave me encouragement. That raised my hopes all the more and I looked forward to Saturday with keen anticipation.
Upon looking over the final result, had to admit that it looked completely sloppy and childish but I hoped the feelings I’d expressed would make up for the crayon-scrawled script. Folding it up neatly, I tucked it into an envelope to give Ms. Taylor on Saturday.
Somehow, someway, I made it to Saturday without dying of horniness.
I was edgy and agitated and I was waking up several times during the night by my body’s attempts to achieve an erection, only to be stopped by my infernal CB-3000. It seemed I could think of nothing else anymore, and the mere sight of Ms. Taylor or Aunt Alexis drove my pulse through the roof.
Whereas before, when I had stroked myself to orgasm, I was able to think clearly afterwards, now, I had no such peace. I was constantly horny, my mind forever dreaming about big breasts, soft diapers, and cute panties to wear. My heightened state of libido seemed to rob me of the last vestiges of my former male ego and I submissively submitted to further sissyish treatment. For some reason, I felt naturally prissier and effeminate than before and I didn’t know if it was due to Ms. Taylor’s hormones that were having an effect on me or my extended chastity.
As a result, I remained passive as I suffered further degrading treatment at my aunt’s and Ms. Taylor’s hands. Nor did I complain when Aunt Alexis slapped my diapered bottom after putting me in a babyish outfit, telling me I was sufficiently dressed for going to meet Ms. Taylor for my date. I could only hope the latter would change me before we went out.
Today I was wearing a short prissy diaper shirt, decorated with pink bunnies and blocks on soft white cotton and short frilly sleeves that showed off my toneless arms. It left a short gap between the hem that barely covered my navel and the elastic waistband of my plastic panties. The ones Alexis had put on me today were lilac colored with polka dots and plastic lace around the legs and seat. From somewhere, she found lacey anklets to put on my feet which seemed well suited for my pink Ked’s sneakers. I looked like an overgrown diapered toddler on his way to pre-school, not a guy on a date with a buxom, pretty woman.
I did my best to wet as much as possible during the morning, hoping I’d be better able to keep myself dry during the day while I was with Ms. Taylor but Aunt Alexis frustrated my plans when she gave me a jumbo baby bottle of warm milk to finish on our way to the school. I tried not to drink it but my aunt warned me of dire consequences if I didn’t, so I was stuck once again. By the time we pulled into the parking lot of the school, I could feel the milk sloshing around in my stomach, waiting for the opportunity to come out into my diapers at the worst possible minute.
Ms. Taylor was in her car when we arrived and as we pulled alongside, the two began a brief exchange.
“Hello Jennifer, it’s always lovely to see you,” my aunt greeted her kindly.
“And the both of you!” Ms. Taylor gushed, “We’re going to have a wonderful time today!”
She completed her thought by bending forward and twinkling her fingers in a feminine manner of greeting at me.
“Hi Ethan!” she said warmly.
My heart skipped a beat and a swallowed hard nervously. She looked so hot today, dressed in a low, scoop-necked tank top that showed her magnificent breasts to great advantage. Her long blonde hair was tousled around her soft shoulders in a way that was sexily disheveled but not messy. To think that I would soon be alone with this hot babe!
I waved back weakly, feeling completely inadequate.
“And here’s his key,” Aunt Alexis said as she handed over the sacred object to Ms. Taylor.
“Thanks,” she said as she winked back at my aunt.
I gulped hard at this new, exciting development.
Between Ms. Taylor’s sexy appearance and the fact that she now had my chastity key back in her possession, my libido shot into overdrive. My little pecker instantly grew into the clear plastic tube until it bottomed out, making me squirm uncomfortably in my seat. I was so excited!! My mouth was dry and I licked my lips anxiously.
The two said their goodbyes and Aunt Alexis soon let me out and drove away. I stood awkwardly, feeling like a complete fool in my sissy diapers as I held my envelope with the love letter in it with shaking hands. I waited impatiently as Ms. Taylor slowly got out to open the back door of her sedan for me while people who were nearby, stopped to stare at me. My face burned with shame and a slight breeze made me overly aware of my bare, hairless legs that were exposed beneath my shameful diapers.
I would have preferred to sit in front with her but Ms. Taylor apparently had other plans. In any event, I was anxious to get inside to escape the attention of the onlookers who were now pointing at me in the parking lot but I hesitated when I saw the oversize child seat she’d arranged in back.
“I thought this would be easier, Ethan,” she said as she guided me into the large pink plastic accessory. As she buckled me in, I gaped in awe at her tremendously deep cleavage yawning before me. Her tight white top with the plunging neckline hugged her big breasts and I could easily make out her sexy white bra underneath. My breathing increased rapidly and I could feel the blood surging through my veins as I stared speechlessly at her. Her sexy plump bosom jiggled enticingly as she adjusted the seatbelts and I could barely think straight. Her soft skin was so close, I could smell her alluring scent and my penis raged frantically inside my CB-3000. Memories of nursing from her succulent melons flooded into my head and I swooned with dizziness. I felt completely helpless until I remembered my love letter.
“Ms. Taylor!” I suddenly gasped, “I wrote this for you!”
She finished getting me buckled in and, in no particular hurry, accepted the envelope from me, opening it up to look at the note inside. I blushed anew as I watched her pretty eyebrows furrowing as she tried to read the sloppy crayon writing but I could tell she was only skimming over it, not really paying any attention to the content.
“That’s nice, Ethan,” she said blithely as she handed it over to me before standing back to close the door. I was crushed by her easy dismissal of my innermost feelings and I saw my chance quickly slipping away.
“B-but—that’s for you,” I blurted out in a rush as I tried to hand it back.
“Thank you, Ethan, that’s very sweet but we have places to go today,” she said as she tossed the note next to me on the seat and produced another baby bottle of milk for me.
“Noooo!” I exclaimed and I raised my hands to stop her.
She smiled at me confidently and pushed my hands down into my lap with one arm as she moved the bottle up to my lips with her free hand.
“Noo!” I repeated again, quickly becoming very upset as the wet nipple brushed against my lips, “I don’t wanna drink that!”
A couple had stopped and was looking at me with amusement as I feebly tried to prevent Ms. Taylor from making me nurse from the baby bottle.
Obviously, my love letter hadn’t made any impression whatsoever on her and she was continuing with business as usual. My eyes filled with tears as I struggled weakly to stop her from babying me further.
“I don’t wanna!” I cried piteously.
“Open up, Sissy,” she sang sweetly as she ignored my resistance, “Baby needs his ba-ba.”
I wanted to be defiant but I found myself submissively accepting the warm rubber nipple despite myself. A tear trickled down my cheek as she moved my hand up to hold the baby bottle in place that I was suckling from. She smiled warmly at me as she saw she’d defeated me once again, accepting my fate meekly and obediently. Why was I powerless to oppose her?
“That’s mommy’s baby,” she said with satisfaction as she beeped my nose gaily, stood back up and closed the door.
I couldn’t believe it! I watched her move around the car to the front seat and get in without a further thought to me as we pulled out of the parking lot. All my efforts had been dashed without the slightest consideration and I was at a loss to understand it.
I continued to nurse from my bottle while we drove across town, Ms. Taylor occasionally looking in her rear view mirror to check on my progress with the bottle.
“Better finish that up, Sissy,” she said, “we’re almost there.”
I hated my lack of willpower but I drained the bottle anyway, just as we pulled into the parking lot for a store of some kind.
“Where are we going, Ms. Taylor?” I asked between gulps of milk.
“To get you some different kinds of outfits,” she said with a playful wink in the mirror.
I was vastly relieved that she was going to finally get me some regular guy clothes to wear. Maybe after that, our date would go a little more conventionally, I hoped.
But my fears were renewed when I read the sign above the door; it read Prissy’s Fashions in bold pink cursive script. Inside the windows, I could see what looked like little girl’s dresses and I became nervous all of a sudden.
Ms. Taylor came around to open the door and I was once again treated to a fabulous view down her top as she bent over to unbuckle my seatbelts.
“Come along, Ethan, we’re going to get you all fixed up today,” she said cheerfully.
“B-but, all I see in there are-are dresses and stuff,” I complained bitterly.
“Now don’t you worry, Little Sissy. I’m your mommy today and mommy’s going to get her sweet little baby all dressed up, extra special!”
Before I could say anything further, she dragged me into the store by my hand, with me waddling to keep up with her long, sexy legs. As we entered the brightly lit store, I saw all kinds of prissy, girlish fashions and accessories and I became increasingly agitated. I was looking at a frilly pink baby dress we were passing when Ms. Taylor suddenly stopped and I almost ran into her.
“Ethan—I want you to meet a very good friend of mine, Heather Milani,” Ms. Taylor said as she stretched out her slim hand before her.
I stared up at the auburn haired beauty before me in dumbstruck silence. She was about twenty-five, tall, with very full lips and emerald green eyes. She was wearing a very tight, stretchy pink top that buttoned down the front and looking like it was in danger of bursting open at any minute. I don’t think I had ever seen such big boobs in my life and I simply stared like a fool at them.
“You must be the little sissy who’s still breastfeeding!” she said enthusiastically as she bent down to look at me. Several women that were shopping heard her remark and stopped to openly stare at me. I blushed furiously and dropped my gaze to the floor but she was beaming at me with unexpected affection.
“I can always tell a sissy who’s still being wet-nursed by the way they stare at my chest,” she explained gleefully. I was deeply ashamed that she had seen through me so quickly and my ears burned with my face and chest.
“Say hi to Miss Heather,” Ms. Taylor prompted me as she patted my thickly diapered bottom.
“H-h-hello,” I croaked, my face a bright crimson.
Bending forward, her massive breasts swung heavily before me.
“Have you had lunch yet, Sweety?” she asked as she cupped her big round boobs temptingly, “I’ll bet you’re hungry, hmm?”
My face felt like it was on fire and I could feel the eyes of the shoppers on me.
“No Ma’am,” I mumbled under my breath. This was mortifying!
“Ethan’s been a special little sissy lately and I thought I’d bring him over here for a little reward,” Ms. Taylor told her, “Do you still have that line of panties in stock you told me about? The line from Missy Marie?”
Heather clapped her hands together playfully.
“I sure do! And your little priss here will simply love them!”
With that, she spun on her heel and strode back into another part of the store to retrieve them.
Ms. Taylor led me over to a section that was mirrored on three sides by angled walls and sat me down on a bench.
“I’ve got your chastity key here,” she said enticingly, “Your little plaything is going to get to come out for a while today.”
Quickly forgetting all about my earlier embarrassment, my mood brightened immensely as I watched Ms. Taylor snaking my clinging plastic panties down and off of my feet. My heart was beating a million miles an hour as she unpinned my thick diapers and pulled them out as well from under me. Using the miniscule titanium key, she inserted it into the lock and I heard that most welcome sound in the world of the lock coming undone. Just as she pulled the plastic tube away from my penis, it instantly sprung alive with pent up arousal, quickly reaching its full height of two inches.
“My…someone looks eager to be free!” she said appreciatively.
Looking down at my little erection, it struck me as looking particularly childlike with its absence of any pubic hair.
Just then, Heather walked around the corner, a selection of girly panties in her hands. She immediately spied my pathetic hard-on and burst into uncontrollable laughter.
Normally, such an honest but disparaging reaction to my little wiener would have sent it retreating into limpness but her unrestrained laughter also caused her massive breasts to jiggle merrily within her snug, taut top. My face was red as an apple again but I couldn’t help being entranced by her luscious melons. It was a strange experience, being both tremendously turned on and humiliated at the same time. Waves of shame and excitement washed over me in successive patterns.
“I’m sorry, Sweety,” she said after she was able to contain herself, “But I haven’t seen a penis that small since I was babysitting my four year-old cousin.”
I dropped my hands over my crotch to hide my shamefully tiny genitals as she bent over to hold out a pair of feminine panties for me.
“Jennifer tells me you just love to wear lacey panties,” she said as she held a pink pair open for me to step into, “And these are some of the prissiest ones we have.”
I couldn’t stop blushing but the sight of the frilly undies being held open for me by this buxom redhead kept my little member stiff as a pencil. My lack of orgasms also conspired to keep my flagpole at attention and as she slid them up my hairless thighs, I felt myself getting giddy with eager anticipation.
The panties were sheer pink, made of a glittery material that gave them a fancy look while still revealing everything inside. They hugged my hard-on and round, youthful buns in a most exciting embrace. Both Ms. Taylor and Heather were looking down at me expectantly as if I were trying on my wedding clothes.
“Stand up, Honey, so I can see how they look on you,” Ms. Taylor said sweetly.
I stood up and twirled around when instructed but as I came back around to face them, I saw a mother and her daughter staring at my crotch from just outside the room.
“Mommy?” her eight year-old asked, “Why is that boy wearing girl’s panties?”
My face reddened brightly again as I saw the look of dark disgust masking her mother’s face.
“I don’t know, Janey, but we have to go,” she said curtly and she escorted her young staring daughter away from our section.
Ms. Taylor and Heather giggled amongst each other while I stood uncertainly, shifting in my pink Keds.
“Here’s another pretty pair, white ruffles on a pink satin—perfect to compliment a sissy’s fancy party dress.”
“I don’t wear dresses, Miss Heather,” I blurted out boastfully, without thinking of the absurdity of my situation.
Heather giggled mischievously as she snaked my panties down my legs.
“Not for long, Sissy-boy,” she said with a smirk as she replaced the sheer panties with the pink satin ones.
“Oh-no-I’m-not,” I said defiantly, even as she snugged the silky panties around my hips, “I’m not--”
Just as I was about to finish my sentence, a teenage girl of about eighteen walked around the corner. She was a stunning brunette wearing a crop top and a clinging mini-skirt and by her name badge, it was apparent that she worked here. She took one look at me in my sissy top and panties and burst into mocking laughter, not unlike Heather’s but with an obvious tone of ridicule and contempt. I was getting used to being laughed at by other women but for some reason, this girl who was near to being a peer of mine affected me more profoundly. In another setting, I would have been doing anything possible to impress her but she obviously found everything about me quite ridiculous. I hung my head in shame as she came over to take a closer look at me.
“What is this?” she said asked, her voice dripping with disdain.
“Laura, meet little Ethan,” Heather said brightly, oblivious of her employee’s disgust, “He’s a sissy breast feeder who has come to get some new outfits.”
As she drew closer, I could see that Laura was even more pretty than I realized and her long dark hair gave her the look of a model. She eyed me critically and I felt myself wilting under her hardened gaze.
“Breast feeding? At his age?” she asked incredulously.
“Some sissies still need their mommy’s milk,” Ms. Taylor explained as she came over and hugged me to her warm, soft bosom, “Don’t you Sweety?”
I was at a loss for words and my lip quivered as I shifted in my shoes.
“What a little twerp,” Laura said emphatically as she crossed her lithe arms over her ample chest.
I squirmed uncomfortably and cast an urgent look up at my teacher.
“Ms. Taylor, can we go home now?” I pleaded, hoping to somehow extract myself from this humiliating situation.
“But we haven’t even found you your outfits yet, Honey.”
I looked back at her with a pained expression as Laura continued to stare at me in disgust.
“Heather, would you mind bringing the Gingham dress out for my little pumpkin?”
“Sure thing,” she said with a playful wink.
I felt like I had to make some sort of stand in front of this babe of a sales clerk, to re-assert my manliness.
“But I don’t want to wear any dresses,” I repeated plaintively.
“Just wait ‘til you see the one I’ve picked out for you, Sweety,” Ms. Taylor assured me, ignoring my reluctance, “I know you’ll just love it.”
By now my boner had wilted under the withering glare of Laura and a small wet spot from pre-cum could be seen on the front of the panties.
“Eww! Look at what you’ve done!” she said accusingly, “You’ve stained those panties—what a disgusting pervert!”
I tried to cover up my crotch just as Heather reappeared around the corner.
“Here you are Honey!” she beamed proudly, “Your new outfit!”
I gaped in shock as she held the short dress up before me on the hanger. It was obviously designed to look like it was for a baby girl although I could tell it was large enough to fit me. It had a pink and white checkerboard pattern with a white bib decorated with colorful flowers. Short puffy sleeves would hide my male shoulders and white lace with soft elastic gathered at the ends. The hem, which was no more than ten inches from the bib was also trimmed with fancy eyelet lace.
Ms. Taylor saw my look of abject shock and she held out a matching pair of panties.
“And look Ethan, aren’t these pretty rumba panties to go over your diapers?”
I stared at the frilly confection in her hands and then back up at Heather was smiling expectantly at me.
“No…no way,” I started, backing up several paces, “there’s no way you’re going to get me to wear dresses too.”
“Now Ethan, everyone knows you’re a sissy, this is just part of your new look,” Ms. Taylor began.
Laura was eyeing me with yet more disgust, practically goading me to defy Ms. Taylor.
“No! I won’t do it!” I shouted petulantly.
Another pair of women stopped to see who was making the big scene in the store.
“Ethan, you will wear what I tell you or you’ll wear it with a sore bottom,” Ms. Taylor said, her voice taking on an uncharacteristically menacing tone.
“No!” I said defiantly as I crossed my skinny arms across my chest, “I won’t do it! I’m not a sissy!”
“You are a sissy and you will wear this dress,” Ms. Taylor insisted, “Do I need to put you over my lap?”
My lip trembled in stubborn refusal but already I was feeling trapped. Although Ms. Taylor had never spanked me before I knew she was fully capable of it. However, in my mind, I still harbored the illusion that she had special feelings towards me. There was no way she’d really follow through with her threat.
“I won’t do it,” I repeated stubbornly, although I had already lost my earlier bluster and conviction.
“Very well,” she said evenly, “Then you’ve just earned yourself a nice, hard spanking. This is something you’ve had coming for some time, Ethan.”
I watched in disbelief as she reached into her purse and pulled out an oval wooden paddle, with six prominent holes drilled into its face. Gulping nervously, I stepped back but Ms. Taylor covered the distance between us with surprising speed. I gasped as she snatched my wrist and held me like a vice while she took a seat on the display fixture.
“No…no!” I squealed desperately as I struggled in vain against her superior grip.
“Ethan,” she said as she looked me squarely in the eye, her pretty face set with determination, “You are a prissy, breastfeeding little sissy who belongs in diapers and plastic panties. And from now on, you will wear baby dresses and girly outfits befitting your status.”
Before I could respond, she yanked me over her smooth, sexy thighs and I tumbled across her lap off balance.
“No, please, Ms. Taylor!” I squealed and several shoppers came over to watch what was happening.
I glanced up to see Laura smirking at my predicament just as the paddle slapped my soft, pantied bottom.
“YEOWW!!” I wailed at the top of my lungs.
Even through the thin, satiny fabric of the ruffled panties I was wearing, the wooden paddle seared itself painfully across both my cheeks.
SMACKKK!!
Once again it swooped down and took my breath away with its fierce, biting sting. Just as I regained my voice, she slapped each cheek individually, giving me no time to adequately respond.
SMACKKK!! SMACKKK!!
Once more, the paddle rained down on each cheek, as if Ms. Taylor had a personal vendetta against each one personally. I howled in pain and kicked my feet, scissoring them in the air behind me.
For a moment, Ms. Taylor paused long enough to tug my flimsy panties off my scalded bottom and down my kicking legs.
“You won’t be needing these any longer,” she said firmly.
Now, my buns lay bared before her and everyone else, each cheek already bearing the bright red oval marks of her paddle. I whimpered in fear and pain, realizing full well that everyone’s eyes were on me as I humiliated myself before them.
SMACKKK!! SMACKKK!! CRACKKK!! SMACKKK!!
I sobbed like a baby as she tattooed my tender bottom with her unforgiving paddle. I would never have suspected her of being able to deliver such a vicious spanking! I made a half-hearted attempt to rise up but her free hand held me securely in place as she took careful aim with her paddle. It swooped down and swatted me harshly at the underside of my cheek, right where the curve of my buns meets my thighs. With tears streaming down my face, I slapped the floor bitterly, unable to escape the blistering spanking I was getting.
Though my eyes were blurred with tears, I could plainly see Laura looking down at me, her arms crossed over her lovely chest as she witnessed my punishment with great satisfaction.
Each excruciating swat upon my tender bottom drove home the point that Ms. Taylor had never seen me as anything more than a diaper dependant sissy. All of my notions about how she felt about me had been no more than wishful thinking, fantasies that I had deluded myself into accepting. As I lay there, taking her punishment, those fantasies evaporated like a puff of smoke. Not only would I never enjoy the affections of my teacher, I would also be submitting to her iron will, which meant among other things, dressing like a toddler girl.
At last, the devastating spanking was over.
She helped me to my feet where I swayed unsteadily, bawling my eyes out before her like an infant. With my panties down around my ankles, everyone was now staring at my miniscule penis which was sticking out like a peanut but I was beyond caring. Ms. Taylor had shattered my will and I simply stood there, my shoulders wracked with sobs. I was powerless to oppose her superior will and I knew I’d accept whatever she should impose on me.
Without a word, Ms. Taylor put her paddle back into her purse and retrieved the CB-3000 which had been put aside. I cried like a baby as she fitted the cuff ring around the base of my genitals and then slide the clear plastic cock tube in place over my tiny, still unsatisfied penis. I watched with immeasurable sorrow as it disappeared back into its prison, to remain trapped until doomsday for all I knew. Putting the lock through the end piece, Ms. Taylor snapped it shut with a crisp click that could clearly be heard throughout the room.
“There,” she said satisfied, “That should keep you out of trouble.”
I looked at her sorrowfully, the tears streaming down my face as my bottom blazed like a five alarm fire.
With her slim, feminine hand, she gently squeezed my swollen balls that were still full of unreleased cum.
“I think we’ll start with six months of chastity, Ethan. That should get you used to going without masturbation.”
Laura was staring at me, no doubt imagining me playing with myself, and shaking her head in disgust.
“Maybe after six months, I’ll allow you to have an orgasm, but then again, maybe not. You’re such a prissy, feminine little sissy that I think permanent chastity is more appropriate for you.”
I sobbed heavily as I looked up at her pretty face.
“And now its diaper time for you, Sissy,” she said authoritatively.
I let her lead me over to where my diapers were still laying and sat down submissively, all the spirit spanked out of me. With her businesslike manner, she quickly powdered and diapered me, showing me none of her usual tenderness which only made me cry harder. As she pulled up my plastic panties, she again fixed me with her stern gaze.
“Are you ready to wear your new baby dress now, Ethan?” she asked although her tone revealed her absolute certainty of the situation.
“Yes, Ma’am,” I sobbed as I nodded my head.
“From now on, I want you to ask me sweetly, to dress you up like a sissy baby—do you understand me?” she said firmly.
“Y-yes Ma’am,” I stammered.
She held the pink and white baby dress before me and then glanced around her to make sure everyone was still watching.
“What do you say then?” she prompted me.
“M-Ms. Taylor, w-will you p-please dress me up like a si-sissy baby?” I sniveled.
“I’d be delighted,” she said, her voice taking on a perceptibly happier tone, “hold your arms up, Ethan.”
My face was crimson as she pulled my top off and then lowered the humiliating gingham dress down upon me. As she turned me around to tie it in back, I looked down at the short, puffy sleeves gathered around my toneless arms, the white eyelet lace contrasting prettily with the pink pattern of the dress. It also occurred to me that with the arrangement in back, I was literally a prisoner of the outfit until someone decided to let me out.
With everyone watching my reactions, I self consciously tried to pull the frilly hem down to cover my embarrassing diapers but to my horror, the lace barely went lower than the elastic waistband of my plastic panties. Heather watched me as I struggled with the dress and she giggled with amusement.
“Ethan, all of your dresses will be cut very short to show off your diapers and plastic panties,” Ms. Taylor explained, “I think it’s important that people realize that you’re not just a boy wearing dresses but a sissy baby that still needs his diapers.”
Looking down at my fat, bulging shiny diapers, I tried again to pull down the dress but it was pointless.
“Don’t you worry about a thing, Sugarplum,” Heather said as she bent down before me, “because this dress comes with its own set of matching rumba panties, aren’t these precious?”
She was holding out the pink ruffled panties that were different from the previous pair I was wearing in one distinct aspect—they were cut full, with a wide crotch and high sides to accommodate a thick, bulky diaper. I sobbed with shame but I meekly submitted as she held them open for me to step into. With agonizing slowness, she eased them up my skinny bare legs, taunting me with views of her big round breasts.
Laura shook her head in disbelief at my submissiveness before she turned to walk off.
Now I was dressed like a true baby girl, my diapers showing plainly beneath my dress except that now they were covered with a frilly pair of rumba panties. White eyelet lace ran around the leg openings, waist and in three bouncy rows across my bulging seat.
It was all too much for me to handle, with the discovery of Ms. Taylor’s true feelings about me, my inescapable chastity, and now my change of wardrobe to that of a baby girl. My shoulders shook as I bawled unashamedly before them.
Heather looked down on me with sincere sympathy, her massive breast just inches from my face.
“Aww, I think its time for your little baby’s nursing session—don’t you, Jennifer?” she asked sweetly.
“Absolutely, I’m sure Ethan is simply starved from his traumatic experience today. And breast milk is the only food he gets in the daytime anymore—I’m quite sure he’d welcome a different flavor for a change,” Ms. Taylor giggled.
“Come along, Sweety,” Heather said as she put her arm around me to lead me out of the room, “I’ve got all the milk you can handle and then some.”
I didn’t doubt her for a moment as I glanced at her unbelievable, voluptuous profile—her breasts were truly massive, straining eagerly against her tight pink top. I felt so helpless and babyish, being led away to be breastfed by this sexy hottie like she were my nursemaid. And it was so embarrassing to have others be told that the only thing I consumed during the day was breast milk. Just like a baby! And she hadn’t even blinked at the information! It was like she looked at me and assumed as much.
Shameful tears were still streaming down my face as she led me into a backroom, with Ms. Taylor right behind us. The room was warmly lit and comfortable, with a plush couch occupying the far wall. Heather took a seat and guided me down next to her, smiling kindly at me as she arranged me across her lap to face her huge breasts.
Unbuttoning the straining upper button of her top, she seemed to be reading my mind as I gazed helplessly at her gigantic, overflowing boobs.
“Have you ever seen breasts this big, Ethan?” she asked teasingly.
I shook my head as I wiped my hand across my face to dry my tears.
“I’ve always had big breasts, Honey, ever since puberty,” she explained as she unbuttoned her top ever so slowly. My mouth was watering as I gaped in astonishment at the deep cleavage between her monster melons. Her skin was soft and smooth and despite my angst from the day’s events, my wiener began growing within its plastic prison. In moments however, it was bearing uncomfortably against the tube, unable to get fully hard or erect. I whimpered and a fresh set of tears tumbled down my wet face at my inability to respond physically and it only added to my feelings of babyishness.
“I know you’re very embarrassed by your new dress, Ethan,” she said sympathetically as she pulled her top away from her exciting, bountiful bosom, “but it really is for the best. Shy sissies like you belong in baby dresses and soft, cuddly diapers.”
I shook my head in weak protest but she had already removed one of her big, plump breasts from the lace cup of her bra and was holding it before my face.
“I knew you were a shy sissy when I first laid eyes on you and I could also tell right off that you were a chronic masturbator too—that’s why its so important that you be kept locked up in a chastity device.”
I sobbed and shook my head pitifully, refusing to accept the truth.
“No…no--”
Just as I opened my mouth to disagree, Heather stuffed her huge warm breast into it, muffling me as my words became inarticulate squeals.
“That’s it sissy, nurse from Mommy’s nipple like the big baby you are.” She said, stroking the back of my head kindly and maternally.
I was utterly unable to resist her and as I squirmed in her lap, I moaned babyishly, my mouth filled with her hard, erect nipple.
“Mommy knows you need your milk,” she told me, ignoring my muted protests, “and I’ve got plenty for you to drink up.”
Out of the corner of my eye, I saw Ms. Taylor bent over to look at me, nursing helplessly like an infant. She smiled and for some reason, I blushed all over again at being watched like that. It was always bad having to submit to the stronger will of a superior woman but it was twice as bad to have another watching me humiliate myself.
“Sometimes, Ethan tries to use his teeth,” she informed Heather who was smiling down on me as I struggled to take in the larger than usual flow of warm milk streaming into my mouth, “if he does, just give his bare thigh a firm slap and that usually calms him right down.”
“You mean like this?” she asked as she unexpectedly slapped my exposed thigh below my diapers. I yelped but submissively resumed suckling from her titanic breast as they both giggled merrily.
For a moment, Heather removed her hard, dripping nipple from my mouth just to hold it before my face and tease me with it. A line of drool strung out between my mouth and the tip of her nipple and I pursed my lips trying to reach the object of my desire. I whimpered weakly and she pushed it back in with a cruel smile.
“Drink it all up, baby,” she said, once more her sweet self, “you’ve still got plenty to go.”
My penis was feeling stuffed within its cage as it fought mightily but in futility against the implacable plastic tube that surrounded it. And to think I had been so close to finally being able to cum! I could still recall the wet feeling of pre-cum that had oozed out of my freed boner as I stood there in the girly panties they had made me wear. And now I might never cum again!! I started to cry all over as I pondered a long life ahead of me, teased mercilessly by Ms. Taylor and unable to even become erect.
Heather saw the fresh tears and she carefully wiped them away with her long, manicured finger.
“There, there, Baby,” she cooed, “I didn’t mean to tease you—don’t cry, little sissy.”
Looking up at her pretty face, I was prevented from explaining what was really troubling me and my attempts at speech were effectively gagged by her massive breast filling my mouth.
“Hush, sissy boy,” she said as she stroked the side of my damp face, “Mommy’s got plenty of milk for her baby—don’t you worry.”
I nursed obediently and settled down, swallowing mouthful after mouthful of warm breast milk.
“Heather, do you have a crib around here I can make use of?” Ms. Taylor asked with her usual soft voice, “Ethan’s coming up on his nap time and it would be great if he could stay here while I meet with my boyfriend.”
Her mention of her boyfriend sent sharp waves of jealousy and sadness through my entire being and I sniffled miserably. My heartthrob and idol would soon be leaving me, to enjoy the company of a real man, while I lay in a baby’s crib, in my dress and diapers, taking my afternoon nap while being kept securely chaste. I could only imagine the sort of things they’d be doing and it was torture to think about it. She’d be kissing and hugging and who knows what else? Maybe she’d even let the guy fondle her breasts. I burned with jealousy and envy at the very thought of it!
“No problem, Hon,” she replied, “I’ve got one in the next room he can use for the afternoon. Just as soon as he’s finished here, although that may be awhile,” she giggled as she looked down at me.
I couldn’t believe how much milk her breast contained and I was completely full by the time she carefully eased her firm pink nipple out of my mouth. I was tired from nursing and my stomach felt like it was bursting when she pulled the other equally massive breast out of her bra cup and placed it before me.
“Open up baby, time for the other breast,” she told me.
“Uh-uh…” I whimpered weakly, shaking my head in protest, “I-I’m full, Miss Heather.”
“Open up Sissy,” she repeated, ignoring my distress, “prissy babies need their milk.”
“No—no--” I cried and I raised my hand to block her but Ms. Taylor held it back for her, rendering me totally helpless.
“I know it’s a lot but its good for you, Baby,” she explained patiently, “open up for Aunt Heather…”
I squirmed and whined but just as I said no again, she stuffed her big breast into my open mouth. I squealed but after a moment, I settled down and began submissively nursing again. Once again, I had been defeated by the stronger will of a beautiful woman. However, it was not long before the inevitable happened. The dam finally broke on my bladder and hot streams of pee began flooding my diaper.
“Sounds like your baby’s wetting himself,” Heather observed with a cute smile as she held my head in place and rocked me gently.
“Mm-hm,” Ms. Taylor concurred, “Go ahead Sweety—wet your pampers like you always do—I’ll change you before putting you down for your nap.”
I blushed hotly as I lay there, completely unable to prevent the soaking of my diapers before these two babes. I squirmed some more as the warm pee began soaking between my legs and saturating the seat while my flow continued unabated. It was probably fortunate that I was wearing the thick, cumbersome diapers that I was because there seemed to be no end of the pee. It just kept flowing unrestrained into the front of my sopping wet diaper, soaking through the soft cotton and working the wetness around the sides and back.
“My, you’re a heavy wetter, aren’t you?” Heather commented ruefully.
I was too ashamed to face her and I screwed my eyes shut as I nursed from her big nipple. The sound of me peeing could easily be heard in the room and I felt my cheeks burning with embarrassment. Finally, the flow came to an end and I lay there surrounded by the warm wetness. My diapers were so wet, I feared any kind of movement on my part that might cause a leak from my panties. I could sense what felt like a puddle of warm pee collected around one of my buns, unable any longer to be absorbed by the thick cloth of my diapers.
My stomach was also becoming uncomfortable with the quantity of milk still in it and I whimpered pitifully as I looked up into Heather’s pretty eyes.
“I think our little baby is about full,” she said to Ms. Taylor, a trace of mocking in her voice.
“Well, he certainly did take in a lot—didn’t you Sissy?” she said as she looked down at me.
I nodded weakly, scared to get up for more than one reason.
At last, Heather eased her nipple out of my sore mouth and carefully placed her huge breast back into her lacey bra cup.
“And now its baby’s naptime,” she said gaily, “after we get those wet diapers changed.”
I struggled to get up slowly, partly afraid some of the milk might come back up. Just as I got more or less in a standing position, I felt a small trickle of pee running down my leg and I choked back a sob of shame.
The women both looked at me as I brought further shame to myself although Ms. Taylor merely smiled down at me with understanding.
“Its okay Ethan, you’ve had a long day and a lot of milk. Maybe I should start dressing you in thicker diapers,” she said as he led me over to the changing pad she’d laid out. I couldn’t imagine wearing thicker diapers than I already was wearing but if I did, I wasn’t sure I’d be able to walk. My diapers already forced me to waddle as it was.
As Ms. Taylor went about her usual business of changing me, Heather looked down on me as she began re-buttoning her sexy top.
“You know, if you’d like, I have a sister that’s coming by this evening. When Ethan’s done with his nap, she could breastfeed him again, that way, you wouldn’t have to worry about dinner for him,” she suggested helpfully.
“That’s a wonderful idea!” Ms. Taylor readily agreed, And I’ll bring another change of diapers for the ride home when I come to pick him up, since I’m sure he’ll have wet himself again.”
Sensing I was going to say something in disagreement, Ms. Taylor popped my rubber pacifier into my mouth to preempt any such thoughts. I whimpered and lay back as she re-pinned the layers of soft, thick cotton around my hips.
Simply marvelous. An epic comprised of all your greatest diapered sissy tropes. And the early breastfeeding/diaper massaging scenes with Mrs. Taylor were...um....very stimulating! Bravo, Bobby! Bravo!
ReplyDeleteOh dear Ethan ... we all KNEW it was gonna end with you in a dress, diaper, and warm bottom!! :: Giggle ::
ReplyDeleteAmazing! Wish we could read more about hos adventures. Even if it was just a flash forward kind of epilog, mentioning briefly if he ever get to cum, or is made to service a man once he's of age, ext.
ReplyDelete