Chrissy's Summer in Diapers

Chrissey's Summer in Diapers



As my mom rang the doorbell of the upper middle-class home, she held my hand firmly. I fidgeted nervously as another stream of warm pee escaped into my already wet diapers. The thick cloth was already soaked between my legs and my snug plastic panties kept it in uncomfortably close contact with my skin.

I trembled with nervous anticipation at the fate that was in store for me behind this door. We were once again at the home of Ms. Julie Johnson, a stern and strict disciplinarian my mom had hired to watch me for the summer while she was away in Europe on business. Ms. Johnson was well known for her 'spank first, and ask questions later’ policy, and I had been the unlucky recipient of one of her severe paddlings which had left my bottom hot, stinging, and red. She seemed to relish the opportunity to apply her hard oak paddle to little boy's buns and I feared another trip over her lap was not far off.

I was nervous for another reason as well, due to my present attire. My mom had dressed me in a little girl's party dress, a fluffy, satin ensemble in soft pink with delicate white lace accents. It had short, puffy sleeves and a big ruffled bib making it look particularly babyish. Underneath, I wore a soft, yet stiff petticoat that flared the hem out to reveal my thick, embarrassing diapers.

Today, I was wearing glittery, lilac colored tights over my legs and a pair of ruffled pink rumba panties, stretched tightly over my big, bulky diapers. On my feet, my usual sneakers had been replaced with a pair of glossy black Mary Janes.

My mom had gone all out to replace my normal clothing with baby dresses, onesies and diaper shirts, steadily adding to my growing wardrobe of toddler items. They were now stuffed into the giant suitcase next to me that she'd packed for my extended stay.

I glanced around me nervously, desperately hoping that no one was watching the overgrown sissy baby standing at the door.

After what seemed an eternity, but in fact was probably only a minute, I heard the sound of high heels clicking on the hardwood surface inside followed by the door opening. I recognized the maid from my previous visit, a pretty brunette in a French maid's uniform that was incredibly sexy. Her low cut white blouse clung deliciously to her perky, well rounded breasts and her long, sexy legs looked fabulous in her sheer, dark hose.

She smiled down on me and invited us in but I was crushed with shame as I waddled in the door, my thick wet diaper clinging humiliatingly to me,

"Ms. Johnson is looking forward to seeing you again,'' she said sweetly to my mom as she ushered us into the foyer.

"Well, unfortunately, I can't stay long,'' my mom replied, ''I'm on my way to the airport to catch my flight.''

"Yes, of course,'' she said, "I'll just get Ms. Johnson."

I watched in captivated silence as she sashayed out of the room like a model, her pert buns moving in an alluring rhythm.

My mom sat me down and I landed with a wet squish in a simple wooden chair.

"Now I want you to behave yourself while I'm gone, do you understand me?'' she said facing me, ''you are to do exactly as Ms. Johnson tells you--got it?''

"Yes, Mommy,'' I replied as I shifted uncomfortably in my seat.

Just then, Ms. Johnson strode into the room looking very smart and businesslike, as well as extremely sexy. She wore a trim, smooth, dark skirt that hugged her every move and dark hose with high heeled black pumps. Her purposeful stride and the authoritative click of her heels sent a shiver of anticipation down my spine.

She came over and shook my mom's hand, a polite smile on her lovely face.

"I'm pleased to see you again, Mrs. Brooks,'' she greeted her.

"Yes, it was so good of you to accommodate my little Chrissey,'' my mom replied.

For the first time, Ms. Johnson appeared to notice me and as she turned to face me, she placed her manicured hands on her curvy hips, looking down at me with obvious disdain.

"Well Chrissey, it doesn't look like you've managed to graduate out of your sissy diapers and dresses, have you?''

''No, Ma'am,'' I replied obediently. I knew how strict she was and I didn't want to take the chance of angering her.

"Are you wet?'' she asked pointedly.

I quailed in front of her dominating presence as I looked up into her dark, demanding eyes. She had a thin white blouse that was literally bursting at the buttons because of her tremendous breasts and it stretched tightly over her round, voluptuous form.

I cleared my throat nervously before replying.

"Yes, Ma'am,'' I answered reluctantly.

She shook her head with disappointment,

''It looks like I've got work to do,'' she said resignedly, turning back to face my mom.

''Well, I know you'll be in good hands, Chrissey,'' my mom said as she gathered her car keys.

I couldn't say I shared her enthusiasm but I really had no choice in the matter.

After a few more pleasantries, the sexy French maid ushered my mom out and Ms. Johnson reached down to take my hand.

"Come along, Chrissey,'' she said, the annoyance plain in her voice, ''let's change those wet diapers.''

I waddled after her, my thick diapers rubbing against my inner thighs noticeably.

She led me back into the spacious interior of her house, back to a softly lit room I remembered from my earlier visit. It was the nursery and it looked to all appearances to be like any other baby's room although it would have certainly belonged to a girl because of its pink decor. I immediately noticed the prominent smells of vinyl, baby powder, and the faint smell of stale pee, the latter a pungent reminder of my own immaturity.

Ms. Johnson led me in and sat me down on a low changing table, its surface covered with smooth, shiny waterproof plastic with a white nursery print pattern. As she began snaking my satiny rumba panties down my hose covered legs, I looked over to see stacks of white disposable diapers on a shelf nearby.

"Those aren't for you, Sissy,'' she remarked, as if reading my mind, ''a heavy wetter like you needs thick, absorbent cloth diapers.''

I blushed at that while she tugged at the snug, wide elastic waistband of my tights and panties, wrestling them over my fat diaper and down my skinny legs, leaving them gathered in a bunch around my ankles.

"Your mother is to be commended,'' she said curtly as my pink side-snap plastic panties came into view, ''this makes changing big babies like you much easier.''

With that, she undid the row of snaps on either side of the panties and pulled it out from underneath me, exposing my saturated cloth diaper as she tossed the damp panties into a nearby pail. The smell of urine surrounded me and I blushed anew, biting my lip with shame.

She shook her head in disapproval and unpinned the two large bunny pins that secured my diaper, pulling it out from under me as well.

As she began busying herself wiping my still hairless genitals and rump, I couldn't help but stare at her magnificent chest that was tantalizingly close to my face. Her big breasts swayed slightly as she moved and I could easily make out the pattern of lace on the cups of her bra. My diminutive wiener stirred at the sight and my heartbeat quickened from pubescent sexual excitement.

Ms. Johnson also noticed it as she shook baby powder over my crotch and as she lifted my ankles with one hand, she delivered a sharp, stinging slap to my exposed bottom.

"OOUCHH!'' I cried as I tried to kick my feet from the shock. Her grip was much too strong however, and she easily held me in place as she applied a thick, sticky layer of diaper rash crème to my cheeks.

"Some little boys, once I've fastened them into their diapers, are tempted to play with themselves,'' she warned me as she lifted my rear end off the changing table and slid a stack of three fresh diapers underneath.

"If I so much as THINK that you've been doing that, I'll put you over my lap and paddle your bottom, do you understand me?'' she demanded as she shook even more baby powder over my wee-wee.

"Y-yes, Ma'am,'' I gulped fearfully.

My little penis twitched nervously as I gazed helplessly at the smooth, supple skin of her voluptuous chest.

Drawing each of the corners of the thick cloth together, she locked them securely together with a pink set of clown faced diaper pins, sealing my frustrated wiener back into its bunny soft prison.

Ms. Johnson paused from her ministrations long enough to open a nearby drawer to find some plastic panties for me. I watched and fidgeted as she sifted through various types and colors; pinks, lilacs and nursery prints, until she pulled out a pair of yellow side snap panties. Undoing the rows of snaps, she placed the open panties dull side up between my legs and slid them underneath me, positioning them under my well padded rump. With my ankles still bound by my tights and rumba panties, she drew the front of the plastic panties up between my legs and began snapping the side snaps together, enclosing the fat diapers I was swaddled in.

I looked down at the shiny vinyl surface and watched as she shook more powder on my inner thighs where they rubbed against the diapers. Putting the powder aside, she grasped my tights and began tugging them up my legs, followed by my silky rumba panties.

"Stand up,'' she ordered me tersely.

I did as I was told and she wrestled the restrictive tights over my bulky diapers, pulling the elastic waistband over the top. The rumba panties, with their light, stretchy material, went on much easier, and she slapped my thickly padded bottom with a start.

"I expect you to tell me when you wet yourself,'' she warned me severely.

"Yes Ma'am,'' I quivered nervously.

This is where I keep the paddle,'' she said ominously, holding in her hand the polished oval instrument of punishment that I greatly feared. My bottom twitched as I gazed at the six large holes drilled into its smooth face and I looked back up into Ms. Johnson's dark, intimidating eyes.

"Yes, Ma'am,'' I said, swallowing hard.

"My nieces have arrived and are in the other room,'' she informed me, ''why don't you go play with them.''

The last thing I wanted was to be seen by a pair of girls but I didn't dare argue with the strict disciplinarian towering before me.

"Yes Ma'am,'' I bleated out weakly.

I waddled out of the room reluctantly, my crinoline petticoat swishing noisily as I made my way to the sound of little girls giggling. I bit my lip nervously outside the door of their room, not wishing to humiliate myself all over again. However, before long, I heard the distinctive sound of Ms. Johnson's high heels clicking in the hallway behind me and I knew I couldn't wait any longer. I stumbled into the room, my mouth dry with anticipation.

I discovered two young girls, probably about seven years old each, sitting before a low table with a tea set arranged on its surface. Their conversation ended abruptly at my entrance, and they burst into uncontrollable laughter. I felt myself blushing a hot red and I fought back tears of humiliation.

"Who are you?'' one of them asked when she was finally able to stop laughing.

"My-my name is Chris,'' I said at barely a whisper.

They burst out laughing again as if even my name was funny and I looked around the room nervously.

"Why are you dressed up like a baby girl?'' the other one asked.

I shifted my Mary Jane covered feet and coughed nervously.

"I-I um, have a sort-of um, problem with um, wetting,'' I stammered uncertainly.

The two girls giggled at that as they looked me up and down.

"You must be a real sissy to wear that girly dress,'' one of them commented.

I was about to say something in defense when Ms. Johnson suddenly appeared at the doorway.

"I see you've met my nieces, Samantha and Susie,'' she said as a statement, ''be sure you get along with them or you'll be going over my knee for a lesson in manners.''

"Yes, Ma'am,'' I acknowledged.

She gave me a stern look before she turned and walked off.

The girls giggled and patted the chair occupied by a doll.

"C'mon Chrissey, since you're still in diapers, you can be our baby,'' Susie said.

I blushed hotly and bunched my fists in rage.

"I'm not a baby!'' I said indignantly.

"Better watch that temper, Baby,'' Samantha chided me with a wag of her small finger, ''or else my aunt will have to spank you.''

I cringed as I reconsidered my outburst. I still remembered all too well the last time Ms. Johnson had paddled me and I'd never cried so hard in my life.

"C'mon Sissy-boy,'' she coaxed me, patting the seat once more.

Hesitantly, I took a seat in the low chair, my knees spreading out awkwardly. The two girls stared openly at the silky front of my panties, stretched out tightly over the fat diapers within them. I tried in vain to cover them with the frilly hem of my petticoat and dress but they were hopelessly too short.

"Too bad we don't have a highchair,'' Susie commented.

"That's okay, I know where aunt Julie has a baby bottle,'' Samantha said brightly as she got up in a flash.

She came back about a minute later with a bottle decorated with nursery characters filled with milk which she brought over and held up to my face. I tried to take it from her but she pushed my hand down and placed the rubber nipple up to my lips. Although both of these girls were shorter than I, Samantha was still slightly taller than I was while I was sitting down. I pulled my head away, refusing to let her bottle feed me but she followed my head stubbornly.

"No!'' I said petulantly.

"Better suck your ba-ba, or I'll tell Aunt Julie,'' she warned me darkly.

I gritted my teeth and stopped fighting her, letting her coax the warm nipple in between my lips.

"That's it...that's a good baby,'' she said with a mischievous smile.

I sucked the warmed milk in humiliation as Samantha held the bottle in place. Each time I tried to hold it myself, she'd push my hands away and chide me for interfering. At the same time, the two girls chatted away with each other, treating me as if I really were nothing but a big baby.

When at last, I had finished the bottle, Samantha rushed out of the room to refill it. While Susie was waiting for her sister, she came over to check my diapers, pulling my dress and petticoat up to expose the waistband of my panties. Her little hands pulled my tights and plastic pants out while I was forced to endure the humiliation of having my diapers checked by a little girl half my age.

“My brother stopped peeing his pants when he was ten...how come you can't?'' she asked pointedly.

"I-um...well I…'' I mumbled.

"Maybe you're just not ready for big-boy underwear,'' she offered.

Just then, Samantha returned with the baby bottle refilled. I could still feel the milk sloshing in my stomach and the last thing I wanted was more of the hated stuff.

"No...no more,'' I protested, putting my hands up to block her.

"C'mon Baby, take your milk like a good sissy or I'll call Aunt Julie,'' she warned me.

"No way,'' I said firmly, keeping my hands in place.

Without hesitation, Samantha called out her aunt's name, making me freeze with fear.

Grabbing the bottle in a panic, I jammed it in my mouth and began sucking earnestly.

"There. there, Baby,'' she said as she took hold of the bottle again and put my hands down, ''I'll help you.''

My face reddened again but I kept glancing behind me to see if Ms. Johnson was coming. Fortunately, she didn't appear to have heard Samantha's summons and I was forced to finish off the second bottle. My young tormentor ensured that I drank every drop of milk before she took it from my lips. I felt miserable with so much liquid in my belly and I wondered desperately what further humiliations these two had in store for me.

Just then, Ms. Johnson appeared behind me, standing imperiously with her manicured hands on her curvy hips.

"Its naptime, Chrissey,'' she announced simply.

I rose to my feet while the girls giggled once more and followed Ms. Johnson down the hall. She led me back into the nursery and folded down the side of the crib, sitting me on its shiny, vinyl covered mattress. The waterproof liner was a pale pink, with a pattern of rattles and toys on its surface and I noted that it smelled vaguely of stale pee. It annoyed me that I was being made to sleep on a mattress for bed wetters although I was hardly in a position to judge, given my recent history.

Ms. Johnson busied herself removing my short dress and petticoat, hanging them up in the closet and leaving me naked from the waist up. She sifted through the dresser until she found a peach colored onesie with a Care Bears logo on the front. This, she laid out next to me as she undid the buckles on my Mary Janes. Putting them aside, she put her long nailed fingers inside the light, stretchy waistband of my rumba panties and began snaking them down my hose covered legs.

"Sorry to take away your fancy panties, Chrissey,'' she said sarcastically.

I remained silent while she drew the soft cotton onesie over my head, feeding my arms through and pulling it down over my fat, bulging diapers. I gazed longingly at the deep cleft between her big, round breasts, visible from the three buttons that were undone in her blouse. My little wee-wee ached with desire as I caught sight of the lace from the cups of her bra, visible when she bent over due to the tremendous weight of her breasts.

Ms. Johnson stood me up and pulled the front and back of the onesie over my diapers, joining the two ends together between my legs and fastening the three small snaps together firmly. With that, she sat me back down on the crib mattress and looped a large pink pacifier around my neck, inserting the thick rubber nipple into my mouth. I sucked on it obediently as she tucked me under the covers, bringing the baby blankets up to my chest and placing a stuffed teddy bear under my arm.

Just then, Samantha and Susie walked into the room and giggled when they saw me in the crib, clad in a frilly Care Bears onesie and sucking on my pacifier.

I blushed anew and Ms. Johnson turned her attention to them.

"Are you girls ready to make some cookies?'' she asked pleasantly.

They let out a chorus of enthusiastic yeses and ran out of the nursery as Ms. Johnson turned on the mobile hanging over the crib and shut out the lights. I was left alone with the low nightlight and a nursery rhyme playing above me.

My frustration over my treatment finally gave way to sleep and I nodded off to a restless slumber.

　

I awoke in the semidarkness with the familiar feeling of a soggy, wet diaper enveloping my hips. The combination of the onesie, tights and plastic panties ensured that the saturated cloth hugged me closely all over. Squirming around or shifting the outer surface of my diapers proved pointless as the wet cloth quickly returned to its close contact with my skin. Feeling around to the sides soon revealed that I had soaked all the way to the back of the waistband and sides.

Strangely, the pacifier was still in my mouth. I was just about to spit it out when I heard an angry, low voice from the next room over. This was followed by a different voice, whining in protest. He sounded as if he were about ready to cry and within moments, I heard the rhythmic slapping sound I recognized instantly as a spanking.

Sucking my pacifier feverishly, I cringed in my crib as I listened to the hapless youth getting his bottom paddled. Within seconds, I could hear him bawling like a baby, howling in protest as Ms. Johnson smacked his defenseless rump with that fearsome paddle of hers.

I twitched and chewed nervously on the big rubber pacifier in my mouth as I listened closely to the spanking, even while a secret part of me was strangely enthralled. I can't explain my feelings but I felt a curious excitement as I visualized busty Ms. Johnson slapping the tender bottom cheeks of this unknown and defenseless youth even while the prospect of being in his shoes terrified me.

At last, the spanking was over and all I could hear were the plaintive sounds of the boy's urgent sobbing. I pulled the baby blanket up higher around my neck for comfort and strained my ears for further clues as to what was happening. After several moments, I heard the other door open and shuffling feet, accompanied by the high pitched clicking of Ms. Johnson's high heels approaching.

I shivered with fear as she strode into the room, holding the hand of a still sobbing boy who was using his free hand to rub his stinging bottom.

She turned on the lights and we both got our first good look at each other.

He looked a couple years younger than me, maybe ten or eleven I guessed, with short hair and a frail looking body. He wore a short hemmed top with frilly short sleeves that barely covered his belly button and a bulging, pink plastic panty covered diaper that was impossible to hide. On his feet he was wearing lacy pink and white anklets and Keds sneakers, also in pink.

As soon as he caught sight of me, he blushed furiously and he tried in vain to stop his crying. I too found my face reddening, particularly since I was about to be exposed before one of my peers.

Leaving the other boy standing in the middle of the room, Ms. Johnson came over and unlatched the side of the crib. I was so worked up that I felt a hot stream of pee flooding the front of my already soaking wet diapers.

Ms. Johnson proceeded to pull back the covers, unfastening the three snaps holding the crotch of my onesie together. I turned beet red as she snaked my tights off of my diaper and down my legs, removing them from off of my feet. Now my wet diaper was exposed before both of them and I felt tears of shame moistening my eyes.

"Well Chrissey,'' she said as she looked down on me disdainfully, ''looks like you've managed to soak your diapers, again.''

I might have said something in response but I realized the pacifier was still stuffed in my mouth.

"C'mon,'' she said as she pulled me to my feet and sat me down on the changing table with a soggy squish, ''time for a diaper change.''

By now, the boy in front of me was sniffling and wiping the tears from his wet face as he stared down with a mixture of surprise and interest. Obviously, he was just as shocked to see another boy dressed like a baby as I was.

"Chrissey, meet Timmy, a boy that is badly in need of discipline, much like yourself,'' Ms. Johnson said by way of introduction.

I could barely hold my head up as he eagerly watched my diapers being taken down. Ms. Johnson dropped the wet and heavy cloth in the diaper pail with a dull thud. Just as she was cleaning my tiny pecker with a washcloth, Susie burst into the room, a baby bottle of warm milk in her hands.

"Here's the bottle you wanted Aunt Julie,'' she said as she stared down at my hairless crotch. Ms. Johnson made no attempt whatsoever to cover my nakedness and I choked back a sob of shame.

"Wow,'' Susie marveled, ''he's really got a little thing!''

"Susie? Can you give Timmy his bottle and then pick out a pair of plastic panties for Chrissey here?'' Ms. Johnson asked sweetly.

"Sure thing!'' she replied, obviously proud to be included in this adult activity.

While Timmy reluctantly nursed from his bottle, Ms. Johnson slathered my bottom with a generous handful of diaper rash crème. Under such intense humiliation, my little wiener had shriveled up to the size of a small grape. When I looked up at Ms. Johnson, it was obvious that she thought of me as being no more mature, physically or psychologically, than a toddler.

I was crushed with shame as she powdered me profusely with baby powder, filling the air around me with its infantile scent.

Taking a thick stack of diapers from the shelf next to the table, she slid them under me and pinned them securely in place.

"How's this, Aunt Julie?'' Susie asked as she held a pair of plastic panties right above my head. They were light pink, with a nursery print and fluffy ruffles running across the back of the seat in three rows.

"Perfect,'' Ms. Johnson replied, ''They're perfect for a big sissy who still needs to wear diapers.''

My face grew even redder and she snaked the panties up my legs, wrestling them over the thick, bulky diapers.

"Now how about a top for our little Miss Priss,'' she said as she pulled the onesie I was wearing off my torso.

Susie went to work while Ms. Johnson tucked Timmy into the crib and arranged his teddy bear. She came back holding a pink and white gingham dress with a built in petticoat that flared the short lacy hem out in a wide triangle.

"That will match his pretty panties quite nicely,'' Ms. Johnson said approvingly.

I raised my arms obediently as she lowered the girlish dress over my head and began securing the buttons in back.

"This is so you don't get any ideas about taking this off yourself,'' she told me as she fastened up the buttons that were well out of my reach.

The dress had a large lace bib on the bodice and short puffy sleeves lined with white satiny lace. After tying the wide silk sash in back into a big bow, Ms. Johnson sat me back down on the changing table to put some stockings on me. They were white and went just above my knees with a pretty satin bow adorning the tops. These were followed by my obligatory Mary Janes.

"There,'' she said satisfied, ''our little pantywaist is all ready for company.''

I whimpered in shame as I sucked on the big rubber nipple filling my mouth. Where would my humiliation end?

She led me out of the nursery room, turning the lights out and taking Timmy's empty bottle as she went. Holding my hand, Ms. Johnson took me to her opulent living room where a young woman was sitting on her plush sofa.

She looked to be about 27 or 28 and very pretty, with long, silky blonde hair that spilled over her bare, soft shoulders. She wore very tight white shorts and an equally snug top that hugged her curvy round bosom in the most revealing fashion. I could clearly make out the lines of her push-up bra underneath and my little wiener stirred within the baby soft cotton of my diaper. Her legs looked flawless to me, firm and silky smooth and when she crossed them, my heart missed a beat.

Under different circumstances, I would have done anything to impress a woman like this but wearing my sissy dress, diapers and Mary Janes, I was crushed with shame.

She stood up when she saw me and beamed a gorgeous smile that was devastating to behold.

"And who is this little cutie?'' she exclaimed as she bent down to look at me.

"This is Chrissey, one of my client's children,'' Ms. Johnson introduced me, ''he still wets his pants so he has to wear diapers for protection.''

My face was a deep shade of red and I looked away in utter humiliation.

"Do you like to wear dresses too, Chrissey?'' the woman asked as she smiled down at me.

"No!'' I protested vehemently, ''my mom makes me wear them.''

"I'm afraid our little sissy isn't quite telling the truth, there,'' Ms. Johnson explained patiently but firmly, ''he has a history of sneaking panties and dressing up, only to be caught later.''

''Aww, I think he's cute as a button,'' the woman commented enthusiastically as she adjusted the puffy sleeve of my top.

"Chrissey, this is Heather, say hello like a good little boy," Ms. Johnson prompted me.

Her perfect, round breasts were right at my eye level and my heart fluttered as she moved about me.

"He-hello Miss Heather," I said uncertainly, using the more respectful title in addressing this beautiful stranger. I was meek by nature but Ms. Johnson's formidable presence made me even more so.

"Well, it looks like Julie has got you very well protected,'' she added as she reached down and lifted up the hem of my dress, exposing my nursery print plastic panties and diapers. She patted my well padded bottom playfully. My face only grew redder and I wanted to run away from this humiliating examination but I didn't want to take the chance of angering Ms. Johnson. She only needed the slightest excuse to put me over her knee for a blistering spanking.

"Run along now, Chrissey, and play with your dolls," she told me.

I did as I was told without protesting, and I wandered into the den to try and find some way to amuse myself. I tried to think about normal things but my mind was in a turmoil and my thoughts kept returning to Heather who had such a spectacular, sexy body. I fantasized about stroking those perfect breasts, while kissing her full, sensuous lips and my heartbeat quickened feverishly.

Ms. Johnson was sexy but in a rather different way. Her big, bountiful breasts looked large enough to smother me with and her dark eyes were beautiful and riveting. But whenever I saw her voluptuous profile, I was filled with fear from the harsh discipline she meted out to weak young males like me. A very secret part of me felt just like the girlish sissy she believed that I was and when I looked down at the bubble bottom created by my fat diapers, my hand went down to touch the lacy ruffles. Did she know things about me that I was afraid to admit to myself?

Ms. Johnson seemed all knowing and powerful to me. Beautiful, smart, and sexy, she carried herself with such confidence and poise that I was quite simply in awe of her.

Sitting down, I pondered these two women as I gazed down at the shiny front of my diapers. The pretty pink vinyl seemed to mock my attempts to be a young man and the cartoon characters only emphasized how babyish I looked.

Visions of Heather and Ms. Johnson danced in my head, making my heart pound in my chest and I ached with sexual need.

At the same time, my little wee-wee felt restrained in my bunny soft diapers, embraced in its warm, welcome folds.

Idly, I lowered my hand to stroke the smooth surface of my panties, indirectly caressing my penis which was held prisoner inside. My head swam with excitement as my little member started to grow in response to my eager ministrations. I recalled the soft delicate skin of Heather's chest and I rubbed myself harder. I imagined her bending down to kiss me and the thought made me want to explode. I was rubbing my diapers furiously now, oblivious to my surroundings with my cheeks flushed and my breathing heavy and labored.

"Well, well, well," I suddenly heard from behind me.

I gasped in shock as I turned around to see the two of them avidly watching me in rapt silence. Ms. Johnson walked over swiftly and she jerked me to my feet, her hard hand swooping up, only to come down and swat me hard on my diapered bottom. Her friend giggled as I yelped in fear.

"What did I tell you about masturbating in this house!?" Ms. Johnson demanded.

"I-I-I...I just..." I stammered incoherently. My excited passion vanished abruptly, to be replaced with abject terror.

"Looks like our little sissy has just earned himself a spanking," she finished for me.

"Oh No!" I begged her, "Please don't spank me, Ms. Johnson, please?" Tears began filling my eyes and my wee-wee shriveled back into insignificance from fear.

"Come along, Chrissey," she said tersely as she took my hand and led me back out into the living room. Taking me over to a prominent corner of the room, she pushed me into it and swatted my bottom again.

"I want you to put your nose in the corner and think about what you've done," she ordered me, "and in a half hour, I'm going to put you over my knee for a much deserved paddling."

I began crying softly to myself as I did as I was told, my mind now filled with visions of the spanking I knew was unavoidable. Ms. Johnson left for a moment, leaving me alone in the room with her sexy friend.

"Poor little thing," she said sounding sympathetic, "here you are."

She picked up the pacifier that was looped around my neck and gently eased it in between my pouting lips, making me blush with shame.

Ms. Johnson came back shortly and she laid the oak paddle down next to me, where I could look at it while still keeping my nose in the corner. The sight of it redoubled my fear and I felt a stream of pee leak helplessly into my diaper.

"Oh!" I squealed as I tried to cross my legs. It wasn't really possible because of the thickness of my diapers and another, stronger stream soon followed the first.

For the next half hour, I sniffled pathetically, alternately looking at the corner directly in front of me and the smooth oak paddle at my side. At one point, I glanced over my shoulder at the large grandfather clock on the wall but Ms. Johnson took notice immediately.

"You'll be over my lap soon enough, Chrissey. There's no need to check the time," she scolded me.

Her friend giggled again, and it was plain that she was looking forward to seeing me cry like a baby.

The big wet spot in the front of my diapers made it harder for me to maintain any restraint on my bladder and before long, more pee was hissing into the soggy cloth surrounding my loins. I was mortified at my own lack of self control, which would soon be evident to Ms. Johnson's lovely friend.

"Alright Chrissey," she said at last, "it's time for you to pay the piper."

I turned around slowly, as tears tumbled down my face.

"Please, Ms. Johnson, I'm so sorry for what I did," I sobbed pathetically, "Couldn't you just let me go this time?"

"Come here, Sissy," she said beckoning toward her lap, "time for a good, hard spanking."

I shuffled forward numbly, as the full realization hit me I was about to have my bottom paddled soundly. When I was within reach of her, Ms. Johnson jerked me over to her side roughly, making me gasp with the suddenness.

"Oh!" I cried, even as Heather stifled another giggle.

"You are the biggest sissy I've ever seen in my life," Ms. Johnson said disgustedly, "and that's saying a lot!"

I stared at the ground, feeling her hard eyes drilling into my face demanding a response. I was too meek to offer any argument and I stood there, my face hot with humiliation.

"Just look at you! A big boy of fifteen still wetting his diapers like a two year old! You should be ashamed of yourself!" she continued to scold me. The wet spot in the front of my diapers was now quite obvious and tears of shame ran down my face.

"And then, I catch you playing with yourself after I specifically told you not to...what do you have to say for yourself?"

I was quaking with fear and my mind was racing trying to think of a way to alleviate my punishment.

"I guess...um...I just...er...I was," I stumbled.

"You can think about that while I warm your little sissy bottom," she said as she yanked my pink plastic panties down off my wet diaper. I shuddered with apprehension as she pulled them down below my shaking knees, the smell of pee surrounding us, and I glanced up to see Heather staring at the dark stain covering the front of my diaper. She was shaking her pretty head and my face burned hotly.

"Chrissey, I'm going to cure you of your masturbating habit once and for all," she told me as she hiked up her dark skirt, "you're a naughty little boy and naughty little boys get spanked in this house."

She had defeated me without even touching me and I didn't resist her as she took me over her firm lap. She unpinned my diapers and pulled them back out of the way, exposing my bare bottom for her paddle. I felt the wet cloth of my diaper between my crotch and her toned thighs and I was even more humiliated knowing that she was also feeling the effects of my incontinence. Sniffling and whimpering, I looked up to see Heather looking down on me from where she was sitting on the couch. She smiled pleasantly as she crossed her silky legs as if this were the most light-hearted affair in the world.

The last thing I felt was Ms. Johnson's paddle resting on my cheeks and it sent a shiver of terror down my spine.

"Chrissey, this will teach you a lesson as to what happens to little boys who break the rules in this house," she said with icy calm.

The paddle swung up in a high arc, descending back down to land with a furious thunderclap.

SMACKKK!!!

I shrieked with pain and kicked my legs even as she brought it down again and again. I quickly lost my ability to breath and I tried to gasp between swats from her ferocious paddle.

SMACKK!! CRACKK!! SWATT!!

I howled in response and beat my fists on the ground and she continued determinedly on her avenging mission. My face was wet with tears as I cried like a baby, jerking over her lap and thrashing around, desperate to escape the blows of that blistering oaken instrument of punishment. She held me firmly, making sure each stinging swat with her paddle landed precisely where she wanted it. Each cheek received its due and she turned them both into flaming globes of fire.

SMACKK!!! SMACKKK!! SMACKK!!

Through the blur of my tears, I could just barely make out Heather as she nodded her head in obvious agreement. I knew I looked like a baby, sobbing and crying but I was helpless to stop it. At last, I stopped struggling and just lay there submissively while Ms. Johnson spanked me with impunity. My cheeks were a bright reddish-purple when she stopped at last.

I was too weak to rise on my own and my chest heaved with heavy sobs that came from deep within me. Never again would I be tempted to stroke my diapers for my own pleasure--the price was simply too high to pay. Ms. Johnson lifted me gently to my feet and she set the paddle down next to her. I swayed uncertainly as I continued crying loudly and profusely.

"Chrissey, I want you to hold your diapers up with your hands and go back to your corner," she told me, "if I catch you touching your bottom, I'll put you back over my lap and we'll start all over again--do you understand me?"

I stared at the rising and falling of her big breasts, straining at her white blouse and nodded my head abjectly.

"Ye-yes, Ma'am," I sobbed noisily.

Heather giggled as I waddled back over to the corner and put my nose back into its recess, sobbing like a toddler.

Later that evening, I was wandering around the vast interior of Ms. Johnson's house, exploring to find what there was. It was apparent to me that she was very well off, although the source of her wealth remained a mystery to me.

At one point, I was making my way down a large hallway upstairs when I thought I heard voices coming from one of the rooms. Upon more careful investigation, I soon found that the voices seemed to be coming from a door that had not been fully closed near the end of the hall. Creeping up on tip toes, I listened carefully and tried to see inside.

"There, there, baby," I heard Ms. Johnson's familiar voice saying, "Take mommy's nipple...there you are...that's a good baby…"

Vastly intrigued, I strained to look inside the room which from what I could see, appeared to be Ms. Johnson's bedroom. On the far wall was a huge dresser, ornately carved from fine woods and above it was a long mirror that covered much of the wall behind it. I couldn't get inside the door any further without widening it but I had a good view of Ms. Johnson sitting on her bed with what looked like Timmy on her lap. My eyes widened in amazement as I saw her stroking the back of his head gently, while she held him close to her tremendous bosom. Even from where I stood, I could plainly see that one side of her blouse was open and Timmy was nursing on her exposed breast, although he seemed to be squirming uncomfortably, no doubt from embarrassment. I had never seen a woman's breast up close without clothes on, not even while it was still in a bra so this was truly a lifetime experience for me. Gaping in awestruck silence, I stared dumbfounded at the situation taking place, not ten feet away. I could clearly see Ms. Johnson's big, smooth breast, which seemed to dwarf little Timmy's head by comparison. He had his eyes clenched shut, as if he could will the humiliating experience away simply by closing his eyelids. Nonetheless, I could see him submissively suckling away at her engorged nipple while she stroked his head and patted his diaper gently.

"That's it baby...nurse from mommy's bosom...don't worry little sissy, there's plenty of milk for you...you still have the whole other breast to nurse after this one…" she told him soothingly as she smiled down on the bashful boy.

I had never seen anything like this in my whole life and I felt a strange buzz of excitement in my stomach although I couldn't explain my feelings. With her big, beautiful breast exposed, I could see much of its exciting shape and my eyes wandered over the entire curvy expanse. How could poor Timmy ever expect to finish off a breast of that size I wondered in amazement. It was only then that I realized I had been holding my breath, and I slowly exhaled as silently as I dared, determined as I was to continue as a witness to this strangely wonderful experience. I could feel Timmy's embarrassment as if it was myself lying on her lap and I could even feel my cheeks growing red from blushing. He must have felt completely overwhelmed, being surrounded by such incredible and intense femininity. The shy little sissy couldn't even bear to open his eyes to look up into the bold, beautiful face of Ms. Johnson while he sucked from her swollen bosom like a baby.

Wiping the drool that had dribbled down my chin, I realized my little wiener was rock hard and twitching from excitement. My breathing was coming in short gasps and I trembled with nervous excitement. I wanted badly to go off somewhere and rub the front of my diaper but I was riveted to where I stood, unable to take my eyes off the two of them.

I watched as Ms. Johnson gently pulled her breast out of Timmy's mouth and then placed it back into the lacey cup of her bra, pulling out the other one and positioning it in front of his lips. He opened his eyes briefly but jammed them shut again in terror as she rubbed her firm nipple across his pursed lips.

"Come on baby, time for more milk," she coaxed him, "come on little sissy...this'll make you grow up to be a big, strong boy."

Timmy was whimpering with embarrassment and he tried desperately to turn his head away from the proffered nipple.

"Uh-uh," he squealed weakly in protest.

Taking his face in her hand, Ms. Johnson guided his lips back to her nipple and she pressed her bosom against his face. Timmy whimpered and with a barely stifled sob, opened his mouth once more and began submissively nursing.

"That's mommy's baby..." she cooed, "that's a good boy..."

Reaching down, she gently stroked the shiny vinyl surface of Timmy’s plastic panties which made me gulp with envy and lust.

I swallowed hard and reached down to feel the front of my own diapers, which separated my hand from my raging boner. The plastic panties and cloth underneath felt cushiony and soft in my palm and I rubbed it furiously, my head swimming with passion and desire. Ms. Johnson was the sexiest thing I had ever seen in my entire existence and in my unbridled excitement, I quite forgot about the punishing spanking I'd received not three hours ago for just this reason.

Panting like crazy, I rubbed my plastic panties and spread my legs slightly to facilitate my need. Ms. Johnson was once again stroking Timmy's head and verbally coaxing his efforts, despite the intensity of his shame. With rapt attention, I stared hard at her fabulous chest, one breast barely contained by the cup of her push-up bra while the other was mashed against Timmy's blushing face. It was all too much for the premature ejaculator that I was and I shot my tiny deposit into the warm, soft folds of my diaper. At the moment of my release, a small cry of ecstasy escaped from my lips before I could close my mouth and I fell backwards in a panic.

Terror filled me to the core as I heard approaching footsteps from the other side of the door, which abruptly swung open to reveal Ms. Johnson staring down at me, her hard eyes boring into me like an icy drill.

"What is going on here?!" she demanded angrily.

My face was flushed red and I was still panting heavily, trying to recover from the incredible orgasm I'd just achieved.

"N-n-nothing," I stammered but Ms. Johnson quickly surmised what I'd been up to. She'd already tucked her breasts back into her blouse although it was still unbuttoned for most of its length, revealing a sensuous view of her lacey bra and her incredible cleavage. She reached down and abruptly yanked me to my feet, causing me to squeal like a girl. Jerking me into the bedroom, she went so fast that I was pulled along on my tip toes, stumbling to try and keep up with the tall, buxom woman. At the edge of the bed, she stopped and yanked my plastic panties down and then unpinned one side of my diapers. Realizing my game was up and I was about to be caught red handed, I burst into tears and tried half-heartedly to stop Ms. Johnson from finding out the truth. Whimpering and sobbing, I flailed my hands in the way but Ms. Johnson merely slapped them and continued what she was doing.

In a moment, she had pulled down the front of my diaper, revealing the small gooey deposit I'd just made so impetuously.

"Oh, oh!" I cried like a little girl in a panic.

Ms. Johnson glared down at me before walking over to her dresser to pick up a large, oval shaped paddle.

"Well...it looks like you didn't learn your lesson the first time," she said as she held me firmly by the wrist, "maybe you need a little reminder, hm?"

Now it was Timmy’s chance to watch as the tables were turned for my punishment. I burst into tears as Ms. Johnson took a seat on the edge of her bed and jerked my plastic panties down around my calves. Watching closely, Timmy made no effort to leave and instead, he popped his thumb in his mouth to watch me get a good, hard, bare-bottomed spanking. Since his own cheeks had felt the sting of Ms. Johnson’s paddle earlier that day, he was only too interested in seeing it happen first hand to someone else. And perhaps my new nanny felt it served her purposes to let him watch for she made no attempt to shoo him away.

With sharp, angry movements, she yanked me over her broad, firm lap and proceeded to finish unpinning my diapers.

“I guess some little sissies just never learn,” she snapped as she shoved the thick cloth of my diapers back between my quivering thighs. I felt the frilly hem of my dress being pulled up to expose the soft, tender cheeks of my bottom for Ms. Johnson’s paddle. I pleaded miserably and strenuously with her for mercy but to no avail.

My buns were still pink and sore from her earlier paddling and when the hard, unyielding oak instrument slapped them again, it was like an explosion of wasps had descended on my poor fanny.

SMA-ACKKK!!!

I wailed miserably and scissored my feet, even though they were tangled within my plastic panties. With a stinging wallop, she delivered another and another blistering swat to my defenseless bottom, re-igniting the inferno that had only been dormant for a matter of a few hours.

Timmy had moved to a better position to watch my punishment and he watched with fascination as the paddle landed with ferocious impact, causing my bright red cheeks to jiggle helplessly before bouncing back to an even brighter and deeper shade of hot, angry red. He watched each stinging slap with interest followed by the reaction on my face as I cried unashamedly, the tears streaming down my face and making my cheeks wet. I hated the added humiliation of having someone else witness my punishment but at the moment, that was several notches down on my list of priorities.

I was kicking frantically as Ms. Johnson slapped my glowing globes harshly with her paddle, not missing any square inch. She worked in a rough circle, swatting the pale, tender sides that had thus far, escaped her wrath. I cringed and squirmed over her lap as she delivered each fearsome swat with frustrating precision. Soon, the entire surface was once again, a bright purplish-red, shiny and blotchy with the heat of a stove top.

I was wailing at the top of my lungs when Ms. Johnson finally stopped her assault on my rear and let me up. I could barely stand on my shaking legs and she scooped me up and placed me on the edge of her bed, sending another wave of searing pain all over my rump as it came into contact with her bed sheet.

“You sit right there, Sissy-boy,” she snapped, “I have something for you that will serve our needs perfectly.”

I was too upset to think what she had in mind and out of the corner of my eye, I could still see Timmy watching me in silence as he sucked his thumb like a baby.

Ms. Johnson came back over to me with something in her hand although because I was still crying profusely, I couldn’t see what it was. Spreading my thighs apart to expose my genitals, she grasped my tiny, limp penis and began working it through a series of loops that appeared to be interconnected in a confounding design. Ms. Johnson’s top was still mostly open and I could easily see her big breasts swaying within the shiny cups of her push-up bra as she manipulated the contraption in her hands.

“This will put an end to your masturbating, once and for all,” she assured me as she wrapped the last loop around my diminutive scrotum. I felt her cinch it up snugly and then I heard the distinctive sound of a high tensile lock being closed which sent a shiver of dread through my being.

Wiping the tears from my face, I looked down and saw my little package trussed up within three loops of some sort of material that felt soft to my skin. Ms. Johnson pulled it one way and then another to test the security of the device until she was satisfied it couldn’t be removed.

“There,” she said with a smug smile on her pretty face, “The next time you try to play with yourself, you’ll be in for a bit of a surprise.”

“Wha-what is it?” I sobbed pathetically.

“It’s a chastity restrainer that I use on especially troublesome masturbators like yourself,” she explained, “You’ve proven time and again that you can’t be trusted so you’ve forced me to take greater measures to control you.

“Sissies that are allowed to play with themselves freely, undermine the discipline that I provide here—and I won’t tolerate it. Like it or not, your masturbating days are over.”

The finality in which she said that made me shudder but I was too frightened to try and prove her wrong.

“It’s diaper time for you, Sissy, and then into your crib for an early bedtime.”

I pouted in mute helplessness, stymied by her absolute power to do what she pleased with me. I chewed my lip in frustration as she pinned me into my thick diapers and pulled my plastic panties back into place. The whole time, Timmy watched in silence although from time to time, I thought I saw him smiling as Ms. Johnson dressed me for bed.

That night, as I sucked from the big bottle of warm milk Ms. Johnson had given me, I tried to tell myself that it wouldn’t be so bad, not being able to play with myself. After all, there were other things to life than masturbation. With my bottom still hot and stinging, I did my best to sleep on my stomach and minimize the fire blazing from within my warm diapers.

　

　

　

At the age of fifteen, I was used to waking up with a boner. Not only that, at my age, it took very little to get my diminutive wiener excited and this morning was no exception.

I was half dreaming of watching Timmy being breastfed by Ms. Johnson and the memory got me extremely excited. She had such big, plump boobs and it fascinated me to no end what it must have been like to kiss them and suckle from her warm flesh. That Timmy had been granted that privilege made me green with envy and not just a little jealous. I was dying to talk to him to find out firsthand what it was like.

My natural inclinations being what they were, I slipped my hands under the baby blankets to stroke the fat, soft surface of my diapers, to give way to my needs. The slippery plastic panties felt wonderful to my touch and the cushiony cloth inside was like a personal pillow, caressing my pee-pee in its welcome embrace.

Somewhere, in the course of the night, I had wet myself although only enough as to be a mild annoyance in the cold light of day. My baby pants did a good job of trapping my body heat which meant the wet cloth was relatively warm to my skin. Spreading my legs, I reached down and began fondling the thick front but instead of the usual immediate gratification that I was used to, I felt a sudden jab of pain. Normally, my wee-wee would immediately rise to the occasion but to my shock and surprise, it was impeded by the restraining loops of the strange chastity device Ms. Johnson had put on me last night. I had forgotten all about it until now and I winced as the loops now pinched my little member viciously. Instinctively, I reached down the front of my diapers to tear the thing off of my genitals but I soon learned that it was secured with an uncanny design and I was completely unable to budge it.

It’s just a matter of easing my wiener carefully out of it, I told myself, but no amount of prying or fiddling with it could extract even the slightest part of my penis from its implacable grasp.

Looking through the bars of my crib, I spied Timmy watching me struggling. He was sucking his thumb again and I stopped what I was doing to sit up straight and face him.

“Hi,” I said, somewhat embarrassed.

He sat up as well and he grasped the bars of his crib as he returned my gaze.

“Hi,” he replied.

His hair looked tousled from his sleep and he was looking around like he needed something. I recognized the look of someone who badly needed to go pee and I knew he was in a dilemma. I watched him fidget in place and saw that his nightey was pulled back in such a way as to leave his thick diapers and pink plastic panties exposed.

“I hafta go potty,” he whispered frantically as he squirmed within his crib.

Suddenly, as if he had said some sort of subliminal key word, I also felt a strong need to go myself. Together, we looked at each other—two helpless sissies that were about to wet their diapers. I tried hard to stop it, but I soon lost the battle and I proceeded to flood my diapers. The pee saturated the front of my diapers and then began seeping inexorably into the seat. As Timmy watched me humiliate myself, I blushed in shame but once it was started, there was no way for me to stop it.

He was squirming in place, obviously debating what to do when I heard him let out a small cry of despair. As he clutched his crib bars with desperation, I could distinctly hear a subtle hissing sound as he began wetting his own diapers before me. Now it was Timmy’s turn to blush and his face turned a bright, scarlet red with embarrassment.

Finally, we both sat back, having little choice but to allow our soaking wet diapers to squish against our backsides.

Just as I always do, I felt very babyish at that moment, my sissyish lack of control verified once again before someone.

I sighed heavily and looked across at Timmy who was crying softly to himself.

“Don’t cry Timmy,” I said as I gazed over at him through my crib bars.

“Have you always worn diapers?” I asked.

He nodded slowly and I could tell he was greatly ashamed of the fact.

“My mommy used to diaper me before bed because I would always wet myself at night…” he began.

“But then I started having…’accidents’, during the day too…”

He looked away and then gazed down at the shiny vinyl outer surface of his wet diapers.

“My mommy would tell me I was just a sissy and then one day, when I had wet my pants at school, she found out I was wearing a pair of panties underneath that I had stolen from my cousin…”

I listened with silent fascination as he told his tale.

She spanked me harder than usual and then told me I was going to wear diapers all the time…last week, she dropped me off here ‘cause she said I needed what she called, ‘sissy discipline’.

“I’ve already been spanked by Ms. Johnson four times,” he said with quiet desperation.

Even though I knew I should continue to try and console him, I was very eager to find out more about his breastfeeding session with her.

“What was it like last night…in her bedroom,” I began tentatively, “you know…sucking from her boobies?”

He turned away and I could see he was blushing again.

“I don’t wanna talk about it,” he replied, his embarrassment obvious.

“I know she’s strict…” I ventured, “But she’s so beautiful too...”

I knew I was in awe of her and my admiration for her was plain to be heard in my voice.

“She has such big boobs,” I said in wonder, “I would give anything to kiss those things.”

“She smothers me with them,” he said, his tears returning to his face, “I can’t breathe…and she makes me suckle like a baby, drinking her milk.”

“Really?” I said in amazement, “What does that taste like?”

“I don’t like it,” he answered petulantly, “but she makes me drink from both boobs even if I’m full.”

My wiener was once again struggling against its bonds as he described the scene which I could still see so easily in my head. She was just so awesome and even though I had seen little of her except for her stern, disciplinary side, I was still infatuated with her.

“Tell me—“

Just then, the door to the nursery opened and Ms. Johnson strode in, interrupting me in mid-sentence. I saw she was wearing a much more casual outfit today, a pair of short, snug fitting white shorts that showed off her long, smooth, creamy thighs. Her tight halter top was a light pink color and it hugged her voluptuous chest in the most mouth-watering way imaginable. I stared at her big, jiggling bosom with rapt fascination, unable to take my eyes off it.

“And how are my two little diapered sissies?” she asked with mock sincerity.

Looking across at Timmy, I could see him sniffling about his wet diapers and he blushed as Ms. Johnson reached down and squeezed his thick, padded bottom.

“Wet as usual,” she commented as she unlatched his crib, “Well, it’ll just have to wait until after breakfast. I’m sure you’re quite used to going around with wet diapers, aren’t you Timmy?”

He sniffed and then shook his head no, keeping his eyes downcast in shame.

Suddenly, Ms. Johnson reached down and pulled his nightey up in back, bringing her hard hand down to swat his exposed diapered bottom. It landed with a loud thud, bucking poor Timmy forward as he gasped in shock.

“Answer me when I speak to you!” she snapped.

The tears tumbled down Timmy’s face as he looked up in fear at his busty tormentor, an expression of abject remorse now showing.

“Ye-yes Ma’am!” he quaked in terror, “I’m v-very familiar with wet diapers.”

“Just like a little baby aren’t you?” she asked, “Except that you’re a big sissy now that still wets his diapers.”

“Yes Ma’am,” he replied sorrowfully.

My eyes were glued to her firm, round buns that were tightly wrapped in her shorts while she stood towering over the cowering sissy Timmy. She had such long, trim legs that she was much taller than either of us which caused us to fear her, all the more.

Abruptly she turned around to face me and I think she caught me staring at her sexy bum.

“And what about you, Little Miss Priss?”

As she took the few steps to cross over to my own crib, her fabulous breasts jiggled within her snug halter top.

I grew suddenly afraid, as if no matter how I responded would earn me a trip over her lap.

“I wet my diapers, Ms. Johnson!” I suddenly burst out in a sissyish confession of guilt.

She crossed her slim arms over her ample chest and shook her pretty head in understanding.

“Just as I expected,” she nodded.

“Well don’t you sissies worry; both my highchairs are covered with practical waterproof vinyl, for just that reason,” she said with a cruel smile, “Maybe if you have to sit in your wet pampers for a while, it’ll teach you a little lesson and you’ll make more of an effort to control yourselves.”

She unhooked my crib bars and swung it open, grasping me by the wrist and pulling me out. I was both amazed and delighted at the extremely low scoop cut in her halter top, which served to reveal her deep cleavage and give me a glimpse at her delicious breasts. I could feel myself getting hotter just stealing sidelong glances at her unbelievable profile. What a body she had!! And to think that lucky sissy Timmy had nursed from those twin melons of pleasure…it was almost too much to believe!

We went out into the kitchen with her holding our hands like we were two toddlers who needed their mommies. Her maid in the French uniform was waiting there for us and I saw her testing the temperature of a big baby bottle filled with warm milk.

“Well there you are!” she said sweetly as she saw me sheepishly entering the room, my diapers sagging from all the pee.

She helped me into the tall highchair which I soon found had nothing to support my feet on. This left me helpless while she secured my wrists on either side of the sturdy plastic tray with a pair of Velcro straps.

“This will keep mommy’s little baby from getting into any trouble,” she assured me.

I felt very babyish as my wet diaper squished against my damp seat and between my thighs, reminding me of how childish I really was. In addition, my feet swung uselessly in the air preventing me from using them to resist with.

As soon as my wrists were taken care of, her sexy maid pushed the warm rubber nipple of the bottle in between my lips, whereupon I was soon rewarded with a steady supply of warm milk. I whimpered in helpless frustration as I was forced to swallow mouthful after mouthful of the hated liquid. The hole at the tip of the nipple was just large enough so that as long as the bottle was tipped upward, milk would flow freely out of it without requiring any sucking on the part of the recipient. This meant that as long as she held it in place, I would be forced to drink and swallow the entire contents, going at her pace, not mine.

Out of the corner of my eye, I could see Timmy being spoon fed some sort of baby mush by Ms. Johnson. While her sexy maid was generously well endowed, Ms. Johnson certainly had the bigger breasts between the two of them and I gazed longingly at her big, round globes.

Strangely, I observed that Timmy wasn’t drinking from a bottle like I was and I wondered why. Could it be that he was going to be visiting Ms. Johnson’s bedroom for another delightful session nursing from her heavy, milk-laden boobs? I felt certain of it and it made me so frustrated I wanted to scream! My little penis was being strangled by my chastity device as I gazed at these two sexy babes before us and here the other sissy was getting all kinds of wonderful attention.

“After breakfast, I’ll take you both in to get your wet diapers changed,” Ms. Johnson promised us, “And then, little Timmy has a big surprise waiting for him.”

She winked at the blushing sissy whose face was covered with baby food.

Why did he get to be so lucky?!
I shouted inside. It wasn’t fair!!

It made me want to go out and do something obnoxious, just to get back at her, but then, I realized I’d probably just get my bottom paddled soundly for my efforts.

At last, I finished my bottle and Ms. Johnson’s maid began feeding me the same mush as Timmy had had. The latter was let out of his highchair and led into the other room while I was force-fed baby food. Her maid paid little attention to me as she shoveled the big, heaping spoonfuls of mush into my mouth and I struggled to keep up with her breathtaking pace. Often she would miss my mouth, either through carelessness, or by accident, and she’d smear the runny food all over my face. She’d chide me for my sloppiness and continue the feeding without making any effort to clean me up.

When I was finished, she undid the straps, rubbing my face with a warm washcloth and then she led me down to the nursery. When I walked in, Timmy was face down over Ms. Johnson’s lap, his diapers unpinned and pulled back, exposing his soft, round little bottom. A long slender tube ran from a hanging red rubber bag that looked as if it were now mostly empty, down to a thick rubber nozzle that was buried in Timmy’s quivering bottom. He was squirming uncomfortably and whimpering helplessly as Ms. Johnson kept the fat nozzle firmly in place. Once again, I found myself strangely aroused by the scene, that is, until Ms. Johnson turned to face us.

“I’m just about done here, Michelle,” she told her maid, “Would you mind filling up another enema bag for Chrissey here?”

My heart skipped a beat as I imagined myself, soon to be in Timmy’s position, getting my own hot soapy enema forced into me.

“No problem!” her maid responded enthusiastically.

Timmy was moaning weakly now, his soft little buns flexing and unflexing helplessly around the thick shaft of the rubber dildo nozzle buried deep inside his rectum. I watched with rapt fascination as Ms. Johnson used her immaculately manicured hands to squeeze and pat Timmy’s round cheeks.

“…That’s mommy’s little baby…” she told him soothingly, “…Take it all in…that’s it…all that nice, soapy water…what a good little sissy...”

I could hear Timmy whimpering and crying softly but still, my little package was struggling to grow harder within my own wet diapers as I watched him.

Somehow, between the visual of her big breasts and her steady administration of the soapy enema into helpless Timmy’s bottom, I was getting horny as hell. On the other hand, the idea that I would soon be in his position, filled me with a strange and terrifying excitement.

Just then, Michelle returned with another rubber bag filled to bursting with hot, soapy water.

We heard the last bubbles disappear into Timmy’s rump and then Ms. Johnson slid the slippery dildo slowly out of his anus. He moaned loudly and sobbed pitifully as she helped him to his shaking feet. His face was a bright red and his stomach full as he glanced fleetingly up at me and then back at the floor. Even though part of me felt a measure of pity for the poor sissy, part of me was guiltily pleased to have been able to witness his purging at the hands of our sexy Mistress.

“Go release that Timmy,” she instructed the fidgeting sissy, “And then come back here where I’ll dress you in your diapers for the day.”

“Yes Ma’am,” he squeaked, and he wasted no time in retreating toward the bathroom, struggling to hold his water as he limped away.

“And now, it’s time for our other sissy’s enema,” she said brightly to me.

Suddenly, I was very nervous as she reached over and began snaking my clinging plastic panties down my skinny legs.

“Please,” I begged her, “Please don’t make me take that.”

Now that the reality hit me full force, tears began to fill my eyes as she took me gently over her lap.

“This is just what all sissies need,” she told me as she unpinned my wet diaper.

“No, no, no,” I sobbed, “Please don’t make me, please?”

“Hush, little baby,” she cooed as she pulled the wet cloth back and stuffed it between my thighs, “You’ll feel much better when you’re done and you’ll be all squeaky clean inside.”

She sounded so enthusiastic about it I found it very frustrating.

Before long, I felt the familiar blunt tip of her enema nozzle prodding eagerly at my hole, searching for access. With a sigh of defeat, I spread my legs and let her push the fat rubber dildo deep into my protesting rectum. I moaned involuntarily as she slid it in and around, teasing my hole with the thick, slippery phallus.

“I just know you’ll come to love this Chrissie,” she promised me, “All sissies come to crave the feeling of a nice big piece of meat filling them up in back…it makes them feel satisfied and complete.”

I squirmed over her lap and whimpered fearfully, too afraid to contradict what she was saying. My back hole felt stretched to the limit but I had to admit, the dildo felt warm and pleasing to me—but it also made me feel even more sissyish, if that was even possible.

Ms. Johnson continued to pump me slowly with the dildo, waiting patiently for me to relax and quit fidgeting. When she was satisfied that I had calmed down, she released the clip and let the hot soapy water surge into my bowels.

I moaned again more urgently, as I felt the liquid gurgling its way deep inside me. I made a perfunctory attempt to rise but Ms. Johnson easily held me in place, ensuring that I remained helpless for her ministrations.

From time to time, she’d snap the clip shut, allowing the water to work its way deep into my insides, while she rubbed my bottom cheeks tenderly, giving me words of encouragement. Several times I was sure I would be unable to take even the slightest drop more when she’d prove me wrong by undoing the clip and sending another flow of soapy water surging into me. I moaned and squirmed, hating the fact that I was so weak and helpless with this buxom disciplinarian.

Somewhere toward the end, Timmy came back into the room, sucking his thumb and holding his other hand over his tiny privates in a childish display of modesty.

Beads of sweat were on my forehead and I was gasping for breath trying to accommodate all the soapy water being forced into my rectum.

“Ohh!...ohh!...m-mommy!” I whimpered, “Ohh!...oh mommy!...I want my mommy!”

“There, there, Sissy,” Ms. Johnson said as she patted my buns, “This is just what mommy’s little baby needs.”

Timmy walked over and was gazing with interest at my predicament.

“Timmy, you can take a seat on the changing table, I’ll be right with you,” she told the curious sissy. Now it was my turn to blush as he witnessed my own session with the enema and I whimpered unashamedly before his wandering eyes.

At long last, the final gurgle of bubbles disappeared down the tube and into my backside, signaling the end of the enema. I immediately tried to get up but Ms. Johnson stubbornly refused to allow it.

“Not just yet, Chrissie,” she said, placing her free hand on my back to hold me in place.

I wanted desperately to get up and run to the bathroom but for some reason, Ms. Johnson was holding me down. She began pumping me once more with the dildo, teasing my hole with the fat rubber invader. I moaned helplessly as she pulled it out slightly, only to plunge it in deeply and make me squeal like a girl. A glance up at Timmy revealed that he was smiling as he watched me being punished and I was angry at his lack of compassion. How quickly I had forgotten about my own feelings upon seeing him take his enema!

Finally, Ms. Johnson pulled the slippery dildo out of my aching rump and she slapped my bottom to send me to the bathroom. I needed little encouragement and I practically ran down the hall to the restroom, my sides feeling like they were ready to burst.

　

Some time later, when I finally emerged from the bathroom, I made my way tentatively back to the nursery, since that was the only place I had any clothes. Michelle the maid was waiting there and she was humming to herself as she arranged a thick stack of diapers on the changing table.

“Ah, there you are,” she said when she saw me in the doorway, “Come in and sit down so I can put you in your diapers, Sissy.”

I went inside and sat down on the now familiar changing table that was lined with pink plastic lace around its edges. Michelle was apparently unaware of my chastity device because she eyed it closely as she helped me get ready.

“Looks like someone’s gotten in trouble for masturbating,” she observed, looking me in the eye.

I blushed hotly as I looked back at her pretty face in embarrassment but said nothing.

“Around here, playing with yourself is a no-no,” she chided me, making my face get even redder.

She raised my ankles and began applying a sticky coating of diaper rash crème to my rump while she continued to discuss my ‘problem’.

“Did you receive a spanking for playing with yourself?” she inquired, apparently wanting to make sure I had been properly punished.

“Yes Ma’am,” I mumbled, too embarrassed to look her in the eye.

“Good, you deserved it,” she told me, “I know Ms. Johnson spanks hard, but sissies like you need to be paddled hard to teach you a lesson.”

“Yes Ma’am,” I responded submissively.

Effortlessly, she raised my ankles again and slid the tall stack of diapers underneath my coated bottom. As she let me down, I was treated to magnificent view down the top of her frilly maid’s uniform, revealing her substantial cleavage and the clasp of her bra underneath. Her big, soft breasts mocked me with their closeness and I ached to be able to kiss them.

“Before long, you’ll come to accept your situation and understand that sissies don’t deserve orgasms like men do,” she explained, “I know it’s hard for you right now, but the sooner you realize that, the better.”

She was powdering my little package and between my thighs before she drew the tortuously soft cotton up and over my crotch. She was so frustratingly sexy with her big, plump breasts displayed before me, while she continued to lecture me on the evils of masturbation.

“It’s best if you just forget about girls and trying to be a man…I’m pretty sure you’ll be in diapers the rest of your life,” she said with absolute confidence.

I whimpered and shook my head but she plopped a big pacifier into my mouth.

“There you go Baby, a soft wittw pacifier to sooth your sissy needs.” She spoke to me in a syrupy, condescending voice and a tear trickled out of my eye to tumble down my cheek. Michelle pulled the ends of the diaper together and snicked them closed with the bunny-headed diaper pins she had nearby. I felt very babyish again and unsure of what lay in store for my future. Was I destined to wear diapers forever? And when would I ever get to cum again? I was going crazy after only 24 hours…what would it be like in a week’s time?

“Now…let’s see here…” she said as she thought aloud, “what kind of plastic panties can we find for a big sissy like you? They need to tell the whole world that you’re no different from any other bed-wetting toddler, and yet…they should also affirm your feminine side too…

“These look like they were made for you,” she exclaimed.

In her delicate hands, she held forth a pair of pink, nursery print side-snap panties with a row of soft, fuzzy ruffles around the leg holes and waist.

“These are just darling,” she added, “We’ll need to find an outfit that shows them off too.”

She threaded my feet through the babyish panties and then up my hairless legs, working them over the bulky diapers pinned around me. As she pulled and jerked on the plastic pants, her big breasts came close to my face and I could smell the scent of her perfume surrounding me. I wanted badly to nuzzle her soft bosom but I had to be content to stare at it instead.

When she finished, she went over to the closet and picked out two outfits that she then brought over.

“Today, you get to choose between two scrumptious outfits…which one do you like more?” she taunted me.

One was a frilly pink confection with a super short hem that I knew would barely reach the waistband of my diapers. The other one was a diaper shirt of sorts that had a pattern of pink lambs and blocks on the front, its short sleeves decorated with more lace.

“I’ll take the shirt,” I mumbled, unhappy with either choice.

“The dress it is,” Michelle said happily, putting the shirt away.

“No, I said the shirt—I want to wear the shirt!” I exclaimed, seeing her misunderstand me.

“I always make a point of dressing a sissy in clothes that he doesn’t like—that way, it gets you used to not having any choices. Because those days are long gone. From now on, everything will be decided for you—you’re much too immature to handle things yourself,” she told me in no uncertain terms.

Removing my nightey, she tossed it aside and lowered the soft, frilly dress over my head. Just as I expected, it was so short that it didn’t even come past my waistband. It also had a wide lace-bordered bib that covered much of the front and appliqués of diaper pins and baby bottles all over. Quite simply, it was the most babyish outfit I had ever seen in my life and I blushed at the thought of being seen in it. It was bad enough that this stunning babe was putting it on me--before long, everyone else in the house would see me as well and I cringed at the thought of it.

Michelle put some lace topped anklets on me and buckled a glossy black pair of Mary Janes on my feet.

“There you are Sissykins,” she said as she stood up and looked down on me, “You’re all ready to go.”

She slapped my thickly padded rump for emphasis and then strode out of the room, leaving me to stare at my humiliating reflection in the full size wall mirror. For a moment, I twirled around and gazed at my big, bubble shaped bottom, bulging out from below my dress. The light shone off the shimmery pink plastic, serving to remind me that I was well protected for a long day of wetting.

I decided to go find Timmy and as I walked out of the room, I was forced to waddle slowly because of the thick bulk of my diapers that slid between my thighs.

After a short while, I found myself upstairs, moving down the hallway in the general direction of Ms. Johnson’s bedroom. I felt full of nervous, sexual tension and my little wiener constantly twitched within the encircling bonds of my chastity device. Up ahead, I could faintly hear the sounds of Ms. Johnson’s voice, filtering out through an open crack in her doorway. Inching forward as silently as possible in my Mary Janes, I snuck up to investigate the situation better.

As I peeked around the edge of the door, I saw Ms. Johnson sitting on her bed with Timmy laid across her lap. Once again, I was mesmerized by the erotic scene before me.

Ms. Johnson had unbuttoned her halter top and it hung loosely from her slim arms, leaving her fantastic chest nearly fully exposed. Her two massive breasts were supported by a white lacey bra that held her two curvy melons in an alluring double cleavage, due to the fact that they pushed up and against each other in the most exciting way imaginable.

I gasped in utter awe at her beautiful boobs and watched with burning jealousy as my rival Timmy, suckled from her right one like a baby. She was cradling his head in the crook of her arm while her other hand was reaching over and softly stroking the front of his fat diapers. Apparently, she had dressed him in some sort of thin, stretchy panties because they were tangled around his ankles, just above his pink Keds sneakers. His smooth, feminine looking legs gave him a particularly childish appearance and his shiny plastic covered diapers completed the scene.

Nonetheless, the humiliated sissy looked distinctly uncomfortable in his position. He was whimpering with embarrassment as he suckled from the gigantic nipple filling his mouth. Her big breast dwarfed his little head and he had his mouth full, sucking and nursing while he fidgeted nervously.

Ms. Johnson was gently encouraging him, as she had when she was administering our enemas.

“…Sh-shhh…there you go…that’s a good little boy…drink all you can…that’s it…that’s a good baby…”

I bit my lip and felt my penis growing stiff within its little prison and I stifled a gasp of pain as it fought madly to break free of its bonds. Unconsciously, I reached down to try and move it as one might do when your wiener is trapped by some part of your underwear. The only problem was, now my underwear was a big, thick pair of diapers, covered by plastic panties, and there was no amount of re-arranging that I could do to relieve the pressure on my throbbing wee-wee.

I cursed silently to myself but I couldn’t force myself to move away from the enrapturing scene taking place before me.

Ms. Johnson was alternating between stroking Timmy’s head, then the front of his thick diapers, helping to stimulate the emasculated sissy further. From time to time, she’d hold her big breast up to his mouth when he tried to back off, to make sure he couldn’t escape this most babyish of feedings. The poor sissy whimpered and mewled, squirming in her lap and desperate to escape his predicament but she was determined to make sure he got his full share.

“Come on Sissy, suckle from that nipple…I know it’s a lot but you’ll just have to try…there you go…that’s mommy’s baby…such a good little sissy.”

Timmy squirmed some more in her lap, trying weakly to rise up but Ms. Johnson held him in place.

“What’s the matter Timmy?” she asked innocently, “Is mommy’s little baby going to wet his diapers? Is that the problem?”

With his face mashed against her massive breast, Timmy was entirely unable to articulate any kind of response. All he could do was to fidget and whimper in weak protest.

“Ahh, I know,” she exclaimed suddenly, “You’re finished with the right side and you want the other one…”

Timmy shook his head no but she easily pushed his head between her breasts and then towards her left one. With deft movements, she tucked her big right boob back into its lacey cup and then pulled the other one out to position it before Timmy’s trembling mouth. He moaned babyishly but kept his eyes shut, apparently because he found the situation so utterly overwhelming to his senses. Ms. Johnson smiled down on him and forced her swollen nipple in between his lips, making him suckle from it as he had the other one.

“There you are…that’s my baby,” she said soothingly, “You’re getting quite a feeding today, aren’t you?”

I bit my lip hard and pushed against the cushiony surface of my crotch, desperate to relieve the strain being imposed on my balls and wiener. My little member was straining furiously in its prison and the pain was almost unbearable.

Suddenly, I heard footsteps down the hall and I tore myself away from my voyeuristic ambitions to run and hide.

　

Late that night, as I lay in my crib listening to the sound of Timmy sleeping, my mind was consumed with trying to find a way to defeat Ms. Johnson’s chastity device that she had secured me in. Every time I thought back to the scene in her bedroom where she was pushing her beautiful, massive breasts into Timmy’s squirming face, my heartbeat doubled and my little penis fought against its bonds determinedly. It was just so frustrating! I wanted to kiss her sexy boobs in the worst way but even more than that, I wanted to be able to stroke my little member without restriction. Whereas before, the soft cushiony cloth of my diapers had served to assist my masturbatory misadventures, now, they mocked me with their caressing, tempting embrace. And pretty Ms. Johnson only added to my frustration with her clinging blouses and tops that showcased her fabulous bosom. She was so beautiful, but yet so strict!

With absolutely no way to relieve myself, all I could think about was sex. Would she ever release me from my bonds? Would I ever get to cum in my diapers again? I could think of little else as I drifted off to a troubled sleep.

　

The next day, after having our diapers changed and fed breakfast, Timmy and I were left in the nursery to amuse ourselves. With little else to do, we soon found ourselves playing with Barbies and after a while, I totally forgot that I was dressed in diapers and a short dress, and I gradually started acting more like a little girl of six, rather than the fifteen year old guy that I actually was. Timmy too, was soon giggling like a sissy and we seemed to lose all our inhibitions with each other.

As a young sophomore back in school, I was used to maintaining a certain false masculinity to keep the bullies from constantly picking on me. But here, I felt like I could just be myself and relax, letting my true self come out. Timmy certainly wasn’t judgmental and if anything, he seemed to be the epitome of a sissy, with his childish giggling and feminine mannerisms.

We were playing and laughing, having forgotten the outside world, when all of a sudden, a pair of gorgeous young women walked through the door unexpectantly. I dropped my Barbie in stunned silence as I gaped up at the two hot babes dressed in skimpy cheerleader’s outfits. One was a brunette and the other was blonde but both were dressed identically in pink shimmery, form-fitting halters and bouncy short skirts. The latter barely managed to cover their panties and I imagined that if they were to turn around and bend over, their perky bottoms and panties would be revealed to us in all their glory. Their halter tops were very low cut and the scoop style in front showed off their wonderful round breasts to my roaming eyes. These girls were both very pretty and the brunette had her long, silky hair pulled back showing her high, model-like cheekbones while the blonde had curls and curls spilling over her soft, bare shoulders. They looked down at us with a mixture of surprise and amusement but I felt I sensed a trace of cruelty in the brunette’s eyes.

“I found them, Julie,” she called out over her shoulder in the direction down the hall, “they were in their nursery, playing with dolls.”

I blushed three shades of red as I looked up at the statuesque girls in their sexy high heels, staring down at us and laughing at our appearances. Here I was, dressed in a very short party dress and diapers, caught in the act of playing with Barbie dolls when any other guy my age would have been out raising hell and getting into trouble. In my extremely agitated state, I suddenly felt the front of my diapers growing wet and warm, as I uncontrollably wet myself. Instinctively, I squealed with panic and my hands went down to as if I could staunch the flow by pressing against my crotch. This only served to bring everyone’s attention to me and they laughed all over again as they realized I was wetting my diapers like an incontinent toddler.

Just then, Ms. Johnson strode into the room and taking in my infantile display, she frowned and shook her head.

“I see you’ve met my two sissies,” she said disdainfully as she crossed her arms over her very impressive chest.

“Yes,” the brunette giggled uncontrollably, “And I think he just peed his diapers.”

Ms. Johnson regarded me sternly and she reached down to put her hand against the warm surface of my plastic panties. As she did so, I stared down the cavernous gap of her cleavage, seeing the delicate lace cups of her bra hidden beneath her blouse. With her bending down so close to me, I inhaled deeply from the subtle feminine scent of her skin and I felt her undeniable superiority overwhelm my senses. Feeling the wetness in front through my vinyl panties, she reached around and felt my bottom while I squirmed in uncomfortable silence, my face glowing a bright red.

“Well, his diapers can still take some more if you’d like to wait to change him,” Ms. Johnson pronounced authoritatively, “Chrissie is used to wearing wet diapers so he can go around like that for a while and it’ll be fine.”

My humiliation knew no bounds as she discussed me in the same terms and tone of a helpless two year-old.

“He often wets himself like a baby whenever he’s startled,” she explained to the pretty cheerleaders who were shaking their heads in amazement, “but I keep him in very thick diapers which can really hold a lot. Just keep an eye on him and check him from time to time and when his seat becomes saturated, that’s usually when I change him.

“I’m going to meet Crystal for lunch,” she continued as she checked her watch, “but I’ll be back in time to tuck the sissies in for their afternoon nap.”

I bit my lip nervously and kept my eyes downcast but I couldn’t stop blushing from the circumstances. I was so ashamed to be spoken of like an infant, especially since I was sitting in front of these hotties in my now very wet diapers, looking and acting like a helpless baby girl.

“You go ahead and take off Julie,” the brunette assured her, “Barbie and I can take care of these two sissies.”

“Oh, I almost forgot,” Ms. Johnson said as an afterthought, “their paddle is hanging up there on the wall. Make sure to use it if they give you any trouble—any at all.”

The two girls smirked at each other and suppressed their giggles.

“Oh believe me—we will!” Barbie exclaimed.

“I like to paddle their bottoms until I see real tears—and then I really lay into them,” Ms. Johnson added with determination.

The girls were nodding their heads in complete agreement.

“Don’t you worry, I’ll make sure they cry if they even think of misbehaving,” the brunette replied.

I shrank in fear as I contemplated the steely will of these pretty vixens that held total power over us in Ms. Johnson’s absence.

“Good. Thank you Alyssa,” Ms. Johnson said as she walked out, “I’ll see you two later.”

The cheerleaders said their goodbyes and then turned their attention back to us.

“I just can’t believe it,” Alyssa said, her tone of voice suddenly becoming very disparaging, “I remember when you were still going to our school…I knew you were a pussy then but I had no idea!”

I felt my face and neck growing hot from my blushing and I could hardly look her in the eye. Casting my eyes down at the shiny surface of my pink plastic panties, bulging out from the thickness of my cloth diapers, I realized just how infantile I looked. It was absolutely mortifying to be seen in this situation by my former schoolmate.

“I should put you over my knee right now,” she said menacingly, “but I have a better idea.”

With that, both she and Barbie pulled a pair of big rubber dildos out of their purses and my heart skipped a beat as I saw that they were mounted on a harness of some sort.

“If you two don’t do exactly as we say…we’re going to bend you over and fuck you in the ass with our strap-ons,” she threatened us as she waved the monster sized dildos at us.

Timmy was quivering like a leaf and I saw his lip trembling with fright as Barbie looked down on him with an intimidating glare. I could hear the faint hiss of pee as he began helplessly wetting himself, breathing in short gasps as he looked around, hoping desperately for some kind of escape.

“I think we’ll have you two little fairies pose for us,” Alyssa announced, “I brought my digital camera and I want to take lots of pictures of you two to show everyone what sissies you are.

“But first, why don’t you paint your sissy boyfriend’s nails, Chrissie,” she ordered me as she walked over to the vanity and snatched up a bottle of bubble gum pink nail polish.

Both Timmy and I were too terrified of the girls, to try standing up to them. I took one look at the fat, ten inch strap-on dildo she had in her hand and I quailed at the thought of refusing her. With perhaps a little more eagerness than I would have preferred, I took the nail polish from her and sat next to Timmy who looked like he was about ready to cry. Barbie got into it as well, dividing the effeminate sissy’s fingers with wads of Kleenex while I applied several coats of glossy pink lacquer to his nails. He sniffled and whimpered but sat there submissively while I added coat after coat to each of his fingertips.

I knew Timmy had little more control of his bladder than I, and sure enough, while he was getting his nails done, I heard him wet himself once again. He began shifting in his seat as the soggy cloth began to surround his crotch and buns and he fidgeted as the minutes ticked by, while his diapers became more and more soaked. Finally, he couldn’t stand it anymore, the warm, wet cloth clinging to his sensitive little bottom.

“Barbie--” he started to whine.

“—That’s Miss Barbie, to you, Sissykins,” she snapped.

“Miss Barbie,” he began again meekly, “Do you think I could please get um, changed…I kinda um…wet myself,” he said lamely, still keeping his eyes downcast on the floor.

“Too bad, Panty-waist,” she retorted, “you’ll just have to get used to it.”

Timmy obviously didn’t like that response and he sniffled in silence, fighting back the tears that threatened to overwhelm the chastised sissy.

Finally, I finished his nails and a part of me took a measure of pride in how well they came out. Timmy looked even prissier than he did before, if that was even possible, and he looked down on his feminized hands with a sob of resignation.

“Now it’s your turn,” Alyssa said as she pushed me roughly.

My pride and subtle sense of superiority evaporated as Timmy gleefully took the nail polish from me and began doing my nails. I could only imagine what these two knockouts must think of us, submitting submissively to their orders like docile sheep when any other guy would never have stood for it.

As I sat down while Timmy painted my nails, I saw Barbie snapping pictures of me, taking humiliating shots that made me look totally sissyish and compliant. After my nails had partially dried, the two girls made us apply glossy lipstick to each other and then pose in the most humiliating ways, holding hands, kissing each other’s cheeks and leaving pink lipstick impressions all over each other, then hugging like pansy lovers, all while the digital shutter clicked away repeatedly to capture our shame on film.

“I was just going to show this to our friends but now I’ve decided that I’m going to post these all over the internet so everyone can see what a pansy-ass sissy you’ve become, Chrissie,” Alyssa promised me.

“Please don’t!” I begged her pathetically but she just crossed her lithe arms over her perky breasts and smirked back at me, nodded in confirmation of my fears and daring me with her eyes to oppose her.

“Okay. Now for the crowning shot,” she said wickedly, “I want you two sissies to kiss each other, right on the lips.”

Barbie giggled at the cleverness of her friend’s wicked plans, slapping Timmy on his diapered bottom for good measure.

“Go ahead, Panty-waist,” she sneered, “Kiss your little boyfriend.”

“Please, please don’t make us!” we begged her again but she picked up her strap-on in her small hands and thrust it in our faces.

“Do I need to use this on you?” she said threateningly.

We shook our heads violently in fear and then looked at each other with apprehension.

“Then plant your pink lips all over your boyfriend’s there,” she said as she rudely pushed me again, “do it now or I’ll make you French kiss him too.”

I gasped in shock at her suggestion and choked back a sob as I turned to see Timmy wiping a tear from his face. Holding him in my arms, I drew him closer but at first, he was afraid to face me. He looked fearfully at our two sexy tormentors and then back to me, realizing we had no choice but to do their bidding. As Barbie kept snapping the shutter on the camera, I pulled Timmy slowly towards me and kissed him tenderly on his lipstick covered lips. He gasped and blushed as no doubt I was as well but Alyssa wasn’t satisfied.

“Make it a longer kiss—reach around and squeeze his butt while you do it. I’m going to time you and if you stop kissing before I tell you to, I’m going to hump your little ass with the strap-on ‘til you can’t walk straight.”

I gulped hard and threw my arms around Timmy, kissing him hard as my hands went down to fondle the thick, pliable seat of his plastic baby panties. Even though I had never kissed a guy before, nor had I ever wanted to, I felt a strange mixture of emotions swirling around inside of me. Timmy’s lips felt soft and warm against my own and his bottom felt cushiony and erotic. I could feel the wetness that had seeped up into his seat and I pulled his panties up by the waistband, so that his diapers wouldn’t sag so much. A tear trickled down Timmy’s cheek but I kept kissing him passionately, afraid to let go. At the same time, my own little wiener was fighting against its bonds within my diaper as it struggled to become hard. For some reason, I was getting tremendously turned on by forcibly kissing Timmy and I couldn’t have been more surprised.

Meanwhile, Barbie was getting countless shots of our lusty embrace, my hands squeezing Timmy’s thickly padded rump while he did the same with mine. Oddly enough, I began to feel Timmy’s tiny little penis beginning to grow within his diapers and as I opened my eyes, I could see that his were half closed, surrendering to my advances. His lips began to part, as if he wanted my tongue and without thinking, I accommodated him. His mouth was hot and he moaned like a girl as I tentatively explored with my tongue, shocking myself with my own lack of inhibition.

At last, Alyssa gave us the signal and we were allowed to stop. Standing there breathlessly, we both blushed profusely at each other, deeply ashamed at having committed the ultimate act of sissihood. What have I done, I demanded of myself. I had just French-kissed the biggest sissy I had ever met and now everyone who had ever known me would see the pictures of it!

I saw the two girls wink at each other and they stepped aside, taking their miniskirts down in unison. I stared openly at their smooth, sexy legs and upper thighs that were now completely revealed to us and for a fleeting moment, I thought we were about to be rewarded for cooperating with their cruel demands.

But my hopes were quickly dashed as I saw them stepping into the strap-on harnesses, a look of evil glee on their pretty faces.

“Bu-bu-but I thought…I thought you said if we did what you wanted…that-that you wouldn’t use those on us,” I stammered nervously.

“I lied,” Alyssa said simply, as she snugged down the wide straps that held the monstrous dildo in place. I gulped with fear as I looked down at the intimidating device, jutting out menacingly from each of the slim, fit, cheerleader’s pelvises. My anus twitched nervously as I contemplated what was about to happen. Judging by the look on Timmy’s horrified face, I don’t think he even knew what a strap-on was but I could tell he didn’t like it. My mind raced as I tried to think of a way to escape our horrible fates but I couldn’t imagine any way out of it. Unlike myself, these girls were in excellent physical shape and neither one of us was any kind of match for them.

Alyssa was facing away from me as she cinched her strap-on up snug against her crotch. I gazed in admiration at the sheer panties she was wearing that stretched across her firm, shapely buns but when she turned around, I was greeted by the incongruous sight of a huge rubber cock jutting out from in front.

“We’re going to help out you two sissies by preparing you for your future boyfriends,” she said as she pushed me down onto my knees into a kneeling position, “And the first thing you need to learn, is how to properly suck a cock.”

Staring at the massive head of her dildo, inches in front of my face, I gulped hard and shook my head frantically, hoping to dissuade her from her humiliating plans. Reaching forward, she placed her hand on my head, to guide it towards her dildo and I was afraid to struggle against her.

“Oh yes Chrissie, this is just the first of many cocks you’ll be sucking. Better get used to it because no woman is ever gonna have anything to do with you.”

Her biting words stung me, making me want to cry and I looked up at her with a sad, pleading expression. By contrast, she looked down at me with an evil smile of smug confidence and power, a woman fully in control and used to having her way.

She pulled my head closer until my pink lipstick covered lips were pressing against the big, bulbous head of her dildo. Refusing to submit any further to this degradation, I kept my lips tightly closed to deny her the satisfaction.

“You want to suck a nice big cock, don’t you Chrissie,” she taunted me cruelly.

“No—“ I responded, but the second I opened my mouth she shoved the dildo past my pink lips, cramming it all the way in until it bottomed out against the back of my throat. I squealed in shock, gagging desperately but both girls laughed at my plight with great amusement.

“That trick works every time,” Alyssa chuckled as she began slowly pumping the dildo in and out.

Kneeling before her, I was forced to suck on the fat rubber cock as she held my head in place and moved back and forth with her sexy hips. I heard another squeal of surprise and out of the corner of my eye, I could see Timmy getting a similar treatment.

“That’s right, suck the big cock Chrissie,” Alyssa said from above me, “This should come very natural to you.”

I blushed deeply as she kept up a steady stream of humiliating comments about my performance.

“Use your tongue Sissy…that’s right, suck it like it was your wittw ba-ba…your future boyfriend will really appreciate all the practice you’ve made….there you go…that’s it, take it all the way in…wrap those pink lips around my cock…that’s it…”

I could see a pink ring around the base of her dildo representing the farthest extent that I had been able to take it in. Her dildo filled my mouth completely, stretching my cheeks wide as it plunged in and out.

“If only your little friends could see you now,” she said as she placed one hand on her curvy hip and left the other one on the back of my head to guide my rhythm, “but then…they will see you—just as soon as I make prints of these photos.”

Looking up, I saw Barbie snapping a shot of me with my mouth full of fat rubber cock and my faced blushed bright red again.

“Smile for the camera, Chrissie,” Alyssa laughed, “but then, it must be a little hard when you’ve got a big cock stuffed in your mouth.”

The girls laughed again and I wondered when they would ever stop tormenting us.

“You see…this is what you’ll be doing to get your boyfriend all nice and hard. That way he can bend you over and ram it in your ass so you can cum like the big sissy you are,” she said caustically.

My jaws were getting sore from having been stretched for so long and at last, Alyssa pulled it out of my mouth.

“Okay, that’s enough fun for you Chrissie,” she remarked as she picked up the jar of vaseline from the top of the dresser.

Barbie had brought two straight backed chairs into the nursery and they bent us down over them, pushing our heads through an opening in the backs that I could just barely squeeze my shoulders through. This left me on my hands and knees, my stomach supported by the seat and my bottom exposed while my torso was trapped through the back of the chair. They had cleverly arranged the chairs so that both of us would be forced to look at each other’s face, now only inches apart. I thought I would try and be tough about the situation but when I saw Alyssa take the oak paddle off the wall, I began crying crocodile tears of fear. Barbie was pulling our plastic panties down and unpinning our wet diapers, exposing our damp bottoms to these merciless vixens while we both whimpered in terror.

Alyssa had positioned herself behind me and because of my restricted position, I couldn’t see her. Nonetheless, I could feel Barbie tugging my wet diapers down, leaving my bottom both helpless and defenseless to their cruel intentions. No sooner had my damp buns felt the chill of the air when I felt the searing impact of the paddle across my tender cheeks. I howled out loudly and tried to move but the chair held me in my awkward position, preventing me from getting up.

SMACKKK!!! SMACKKK!!! WHACKKK!!!

I wailed out in pain and grabbed the chair legs as Alyssa delivered several stinging wallops to my soft, round bottom, quickly bringing me to real tears. I sobbed and cried helplessly as she delivered a series of harsh, angry swats with that dreaded instrument of discipline, aiming careful and applying as much force to each slap of the paddle as she could. Those holes in the paddle really added to the sting and that, combined with the dampness of my bottom, made each swat feel like I was being spanked with a red hot frying pan.

As I lay there sobbing, she handed the paddle to Barbie who took up a similar position behind Timmy. The poor sissy didn’t even wait for her to start spanking him, he burst into tears immediately and began crying like a baby.

“Keep that pretty little bottom right where it is,” she said wickedly as she raised the paddle up and behind her, “’cause I’m about to give you something that’s really gonna make you cry.”

Through the tears in my eyes, I saw her bring down the paddle in a blistering swat at poor Timmy’s defenseless bottom. His eyes widened like saucers and he howled out at the top of his lungs. I watched with perverse fascination as my sissy companion had his fanny paddled without pause or mercy. He beat his little fists on the floor and kicked his legs as the paddle slapped his helpless cheeks in blistering, angry succession. His youthful buns jiggled miserably with each punishing swat and I looked into his face to see the hot tears streaming down his distraught face.

Before long however, Barbie finished and she set the paddle down with casual disregard, taking the time to coat her dildo with a thick, sticky layer of vaseline. As I contemplated what was about to happen to him, I felt Alyssa’s own strap-on, pushing firmly against my back hole, probing for entry. I moaned weakly but the fight had already been spanked out of me. Submissively, I lay there while she pried my stinging cheeks apart with her long, manicured fingers, attempting to gain entry to my virgin back hole. I looked to Timmy for support and saw that he was whimpering with fear, crying softly while Barbie slowly and tauntingly rubbed the thick head of her dildo up and down the crack of his red, hot and stinging bottom. His moans were coming in shorts squeals now, more out of fear than any real pain. Barbie had an evil gleam on her face as she positioned the fat dildo against Timmy’s hole, making him squirm with terrified apprehension. Pushing firmly, she forced the rubber phallus past his pouting sphincter and deep into his anus, making him savor the fullness of a giant cock.

Timmy squealed loudly, his face a picture of shock and distress while Barbie drove the big dildo deep inside him, holding it in place to make him feel every humiliating inch of it. She smiled with smug satisfaction as Timmy squirmed helplessly, his body trapped within the chair. Just then, I felt Alyssa’s own strap-on push past my rim and it slid deep inside me, making me cry out with a loud squeal. I felt like I was being split in two as she pushed it farther and farther, forcing me to spread my legs in abject submission.

I had never felt so emasculated in my life as these two sexy babes began to slowly and methodically hump us. At my young and tender age, I hadn’t given too much thought as to what it would feel like to have a big, thick cock pumping me in and out but I was surprised by the sensation. It had initially hurt quite a bit as I struggled to accommodate the massive invader in my little hole but as she slowly slid it in and out, I felt another sensation starting to take hold—that of sexual pleasure.

Looking back up at Barbie, I saw her reach down and switch something on, followed by a low buzz. Alyssa must’ve had the same thing because I could feel a slight vibration around the dildo sliding inside me. It appeared that the vibrating device was connected to a part of her strap-on that was intended to provide stimulation to the female wearer and I could see the effect of this when I looked up to see Barbie, her eyes half closed as she savored the waves of passion flowing through her curvy, sensual body. She looked utterly ravishing, her long blonde curls swaying back and forth as she drove the strap-on deep into poor Timmy’s bottom while he squealed like a schoolgirl. Her round breasts, which were the size of two ripe cantaloupes, jiggled in her snug, form-fitting top with each thrust she made into my helpless, hapless companion. From time to time, she’d bite her lip as she held the dildo as far in as it would go, which also had the effect of pressing the vibrator hard up against her sex. Both she and Alyssa were now moaning with pleasure as they ground their dildos into our sissy holes. I looked at Timmy’s face which was still covered with my lipstick kisses and even he was starting to get tremendously turned on. He was moaning freely with each thrust of Barbie’s strap-on, and breathing deeply from the pounding he was getting.

Both girls picked up their pace and the dildos slid in and out, faster and faster, as they gripped us tightly by our hips. Timmy’s moans were coming closer and closer together and all of a sudden, I heard him cry out as he came uncontrollably in his wet diapers. I too, would have liked to cum, but my chastity restrainer prevented my efforts to get hard. Despite the intense stimulation my hole was receiving, by tiny little wiener was still held with implacable bonds that refused to allow me to enjoy any sort of sexual activity. I could only cry tears of frustration as Alyssa pounded my back passage thoroughly, digging her long nails into the soft skin of my hips as she sought to get the best grip she could. I wailed and squealed while Alyssa enjoyed every tantalizing vibration of her device, sending her to the brink of orgasm.

At last, both girls seemed to peak at the same time and with one last hard push, they jammed their dildos in as far as they could go. My hole was stretched to the limit and I could feel the fat rubber head pushing furiously against me. Alyssa used all her body weight (all 120 pounds of it) to keep the dildo crammed up inside me, while I moaned like a helpless little girl. With a room deafening cry, both the girls came with great exuberance, spending themselves as wave after wave of orgasm roiled through their slim, youthful bodies. I watched with fascination, Barbie’s face reddening as she gasped from the strength of her climax. Her curly hair was spilled over her pretty features in a picture of wild dishevelment as she ground her dildo against Timmy’s backside. He whimpered and squirmed, trying to get away from the monster cock buried inside him but there was nowhere for him to go. I too, struggled to escape my tormentor’s determined assault, but I could do nothing to alleviate my suffering. My poor back passage was tired and sore from the intense reaming it had taken and I waited impatiently for Alyssa to free me.

When the girls had finally spent themselves, they reached down and clicked the vibrators off, slowly easing the fat dildos out of our bottoms. I breathed a deep sigh of relief and when I looked into Timmy’s eyes, I saw that he was smiling sheepishly back at me.

“There,” Alyssa said breathlessly, as she began undoing the straps to her strap-on, “Let that be a lesson to you sissies. Now you know your place in this world. Only next time, I’ll have my boyfriend come over and cum in your mouth. I’ll bet you’d like that, wouldn’t you Chrissie.”

She emphasized her question with a harsh slap to my still red bottom.

“OWWCHH!!” I cried out, still immobilized by my position within the chair.

After cleaning up their dildos, the girls re-pinned our wet diapers and pulled our plastic panties back into place, leaving us to endure the cool, clammy embrace of the wet cloth. Frankly, at this point, I was afraid to ask them to change us and I shuddered to think what else they might have in mind for us. After putting their strap-ons back into their purses, the girls stepped back into their miniskirts and zipped them up, an act that was extremely arousing all in itself.

Just then, Ms. Johnson came back home and it appeared we would saved from further torment at the hands of these totally hot, yet cruel cheerleaders.

“Hi girls, how did it go with the sissies?” she asked as she set her car keys down. I saw that another woman had come in behind her and much to my relief, she smiled warmly at us.

“Well, after they started playing with their make-up, they kinda got carried away with each other,” Alyssa remarked with a smirk directed at Barbie.

Ms. Johnson came up and stood over me, her pretty features creasing as she looked down at the lipstick kisses all over mine and Timmy’s face.

“What on earth have you two been up to?” she said with exasperation.

My mouth dropped open and I wanted to relate the entire humiliating hour that had just transpired but a stern look of warning from Alyssa who was standing behind Ms. Johnson told me that there would be hell to pay if I did. For a moment, I struggled to find the words as I looked around, first at Timmy, who was now biting his lip guiltily, and then at Alyssa who was regarding me coldly.

“Um…I guess um, we were just—you know, kinda havin’ fun, Ms. Johnson,” I mumbled meekly.

She shook her head in obvious disapproval but said no more of it, apparently thinking that it was only natural that two sissies left alone would sooner or later begin kissing each other.

Reaching down, she squeezed the seat of my diapers and felt the soggy cloth within my vinyl panties, confirming her suspicions of my condition.

“Looks like these two sissies are due for a diaper change,” she told her friend that had come in with her, “Would you like to help me, Crystal?”

“Sure,” Crystal replied brightly, “I’ll take this little cutie here.”

I blushed as she began tugging my clinging plastic panties down without any prompting, as if she were my own mother. Nonetheless, I couldn’t help but notice that she was totally sexy with a thin, clinging sweater she was wearing that hugged her immense breasts closely. She appeared to be in her late twenties, tall, and she had her dark hair swept back in a sassy pony tail. Her manner was warm, yet firm, and I could tell she was quite used to dealing with helpless babies who wet themselves. She treated me as if I were just another one that couldn’t do anything for himself and she made me hold the hem of my party dress up while she worked my panties off my diapers and down my legs. After putting my soiled baby pants in the diaper pail, she sat me down on the changing table and proceeded to unpin my soaking wet diapers.

“My, my…” she tsked me, “This one’s quite a little wetter.”

My face reddened and I bit my lip with embarrassment.

“Yes, he has no more control of his functions than any baby,” Ms. Johnson told her as she stood towering over me, “Personally, I’m doubtful that he can even be potty-trained.”

Crystal shook her head but she smiled down at me nonetheless.

“That’s okay Chrissie,” she said as if she were addressing a two year-old, “We’ll get you all fixed up in some nice thick diapers before your nap.”

My face reddened some more and as I glanced over, I saw Timmy smiling down at me and I suspected some part of him enjoyed seeing me humiliated.

Crystal pulled the wet diapers out from under me and she noticed the distinctive, red oval marks that had been left by the paddle.

“Well, it looks like someone’s been a very naughty boy,” she said, half smiling at me, “Did you get a wittw spanky-wanky?”

I couldn’t stop blushing from her babyish treatment of me and I nodded in acknowledgement.

“Awww…does baby’s little bottom hurt, hm?” she asked with mock concern, “Aunt Crystal’s gonna make it feel all better, just you wait.”

Grabbing a big handful of diaper rash crème, she smeared it across my entire backside, coating it liberally with the sticky stuff while her other hand gripped my ankles and held them up over my head. I held onto the sides of the changing table desperately, blushing furiously as this stranger ran her soft slippery hands across my punished buns, working the greasy emollient thoroughly into my skin.

Barbie and Alyssa watched us in silence, shaking their pretty heads at my babyish routine. After setting me back down, Crystal took a stack of three thick diapers and slid them under my rump, positioning them evenly on both sides.

“Here you are Sissykins, a nice big diaper for our big baby,” she said brightly. Taking the baby powder, she began shaking it all over my crotch and stomach, humming a nursery rhyme as she did.

I bit my lip with embarrassment as everyone stared down at me, a young man being pinned into his diapers like a helpless child.

After snicking them closed, she patted me on the thick front and said, “Now just you wait Chrissie, while I find you a nice pair of plastic panties for you to wear.”

I sat waiting in silence, my face and ears burning with shame while she sifted through the drawer looking at various baby pants, holding some up and commenting on them.

“Now these are cute,” she said admiringly, “such soft ruffles around the leg and waist—they’re perfect for a sissy like you who’s still in diapers!”

I wilted under her humiliating treatment as she gathered the leg openings in her delicate hands and began pulling them up my legs.

“Hopefully, these will fit over your thick diapers, Chrissie,” she said as she slowly drew them upwards.

“They should be fine,” Ms. Johnson offered helpfully, “those are all full-cut to accommodate thick, thirsty diapers like these sissies wear.”

Sure enough, as Crystal began snaking her long fingernails around the waistband, she worked the shiny pink plastic panties up and over the bulky circumference of my diapers, sealing them up fully and completely.

“There,” she said satisfied as she patted the smooth, vinyl covered front of my bulging diapers, “you’re all set for your afternoon nap.”

The cheerleaders shook their heads once more and then said goodbye to Ms. Johnson and Crystal. While Timmy got his diapers changed, I sat in uncomfortable silence, still trying to come to terms with the intense humiliation I’d suffered today. I’d never felt like such an emasculated sissy in all my life.

At the same time, Ms. Johnson went and filled a jumbo sized baby bottle with milk and warmed it up, bringing it in right as Crystal was finishing up.

“Well Julie, here you are; two sissies, diapered, changed, and ready for beddie-bye,” Crystal said as she slapped my thickly padded bottom.

“And now it’s time for the babies to get their milk before their naps,” Ms. Johnson said with an evil gleam in her eye.

Taking our hands, the two sexy women led us out into Ms. Johnson’s spacious living room and sat us on the expansive couch next to them. I meekly submitted as Crystal sat down and pulled me up onto her lap, cradling my head against her big, soft breasts. I was filled with sexual excitement as my cheek touched the fuzzy, comforting material of her thin sweater that was wrapped tightly across her swollen bosom. I was positive that my moment had finally arrived—at last, I was going to get to nurse from a bare breast! I had hoped for Ms. Johnson, of course, but this woman was exciting in her own different way. Her big, round boobs had captured my attention from the moment she had walked in the room and now I was about to get the chance to suckle from them. My tiny little penis began to immediately harden, only to be painfully restrained by my chastity harness.

I was facing the other end of the couch where Ms. Johnson had positioned Timmy, evidently to give him the same treatment. I smiled across at him, even as he became apprehensive of another humiliating session at our guardian’s big breasts.

“I’m so glad you were able to help me out with my…you know, situation,” Crystal said to her.

“Oh, don’t mention it,” Ms. Johnson replied with a waving dismissal of her finely manicured hand, “Its good experience for a sissy to nurse from the breast again.”

“Its just that with my baby being unable to take mother’s milk, I was forced to use a breast pump to get rid of all of it…it just seemed like such a waste.”

“Oh yes, I totally agree,” Ms. Johnson said as she began unbuttoning her straining blouse, “And this little sissy needs all the milk he can get to be a big, strong boy.”

She said the latter part in her mocking voice which left no doubt about how she felt about Timmy.

“Looks to me like you’ve got quite a bit to feed him, just by yourself,” Crystal remarked as she admired the mammoth size of Ms. Johnson’s right breast, now visible that her blouse was fully open. I felt my temperature rising as I stared past the twin mountains of Crystal’s, at the soft, plump skin of Ms. Johnson’s mammary now revealed. I licked my lips in excited anticipation of what was about to happen.

The latter chuckled at Crystal’s observation.

“Yes, well, I’m sure we can count on little Timmy waking up from his nap this afternoon with a very wet diaper.”

The two of them laughed as Ms. Johnson carefully lifted her heavy breast out of the lace cup of her push-up bra, positioning it before Timmy’s brightly blushing face.

“Here you are Sissy,” she said soothingly, “Time for baby’s milk.”

Timmy squirmed uncomfortably and made a half hearted attempt to move away but Ms. Johnson easily held him in place and she ran her erect nipple across Timmy’s quivering lips.

“Open up Timmy, time for num-nums!”

Timmy closed his eyes and shook his head no but before long, he acquiesced, taking the erect nipple in his mouth and submissively suckling on the tremendous breast being pushed against his face.

“Thaaaat’s it,” Ms. Johnson said in a whisper, “Suck like a good little baby.”

I was whimpering now with jealous impatience, fidgeting while I waited my own turn to nurse from Crystal’s fantastic chest. She smiled down on me warmly and looked me directly in the eye.

“Don’t worry Babykins, I haven’t forgotten about you.”

With that, she brought the warm bottle of milk up to my mouth and pushed the rubber nipple against my lips. I whimpered in protest but she slid it across my lips until I surrendered to her efforts. Looking deep into her pretty eyes, I was forced to suck from the bottle, taking in mouthfuls of warm milk and swallowing it while she kept the bottle firmly in place. I moaned in protest but the big rubber nipple filling my mouth prevented anything intelligible from coming out. Meanwhile, Crystal’s hand wandered down to softly stroke the smooth surface of the front of my diaper, sending electric shivers through my body.

“That’s mommy’s little baby,” she cooed as she smiled down at me, “Drink your ba-ba like a good little baby.”

I blushed deeply as I submitted meekly to her ministrations, yet I felt intensely frustrated that I wasn’t being allowed to nurse from her breast directly. They were so close, yet I couldn’t see underneath her thin sweater that was stretched tightly across her ample bosom. Looking across at Timmy, I saw that his face was dwarfed by Ms. Johnson’s titanic boob, and I watched with fascination as he sucked obediently from her. She was cooing down at him, softly encouraging him while still treating him very babyishly. I had to admit, he looked rather cute with the pink lipstick kisses still covering his blushing face. His legs were slightly apart, due to the thick bulk of his naptime diapers, which Ms. Johnson was also slowly stroking. Even her hands were sexy, with her creamy skin and long manicured nails. I watched as she softly rubbed the front of Timmy’s diaper, making him mewl like a kitten. His legs were bare except for his usual pink Keds and anklets he was wearing and I noted the smooth, hairless skin of his thighs. His feet were fidgeting slightly as he tried to cope with the raw sexuality of Ms. Johnson and my heart beat faster just watching him. He looked so completely babyish that I couldn’t ever imagine him growing up.

After finishing off one breast, Ms. Johnson, tucked it back into its lace cup and pulled the other out, forcing it into Timmy’s pouting mouth, much as she’d done before. I squirmed in frustration as I sucked helplessly from the warm rubber nipple in my mouth. Looking up at Crystal’s pretty smiling face, I whimpered in protest but she merely smiled back at me, holding the bottle firmly in place to prevent me from refusing it.

When Ms. Johnson finally finished with Timmy, after ten maddeningly long minutes, I thought my chance had finally come. But rather than producing one of her delicious breasts for me, she instead buttoned up her blouse and we traded positions over the two women. Now Timmy was being cradled by Crystal and Ms. Johnson was holding me. I began whimpering louder, desperate to get my lips around one of her gorged nipples I saw poking rigidly through her blouse but she looked at me determinedly and firmly placed the bottle back in place for me to drink from. I didn’t want any part of it, especially as I watched Crystal begin to slowly unbutton her sweater from the front, revealing two massive melons, restrained only by her lacy white bra.

“No…” I whimpered weakly to Ms. Johnson, “No, please…I want… I want…”

She cut off my protests by pushing the wet rubber nipple between my quivering lips, forcing me to suck again from the large bottle. I choked back a sob but I sucked submissively on the baby bottle, taking more and more of the hated warm milk.

Timmy tried to shake his head no as Crystal delicately offered her big, bare breast to him but she reached behind him and pulled his head forward, forcing him kiss her dark nipple. Her breasts were so bursting with milk; I could see it already starting to dribble down from the tip of her nipple where she slowly, tantalizingly rubbed it across Timmy’s lips. Whimpering like a girl, he finally submitted and took her breast into his mouth where he began suckling in defeat.

During this time, I was kept prisoner in Ms. Johnson’s arm, my head resting against her big, soft bosom while she made me drink the remainder of the bottle. With each frustrating moment that passed, I became angrier and angrier that Timmy was getting sexually pleased and I wasn’t. I wanted to fight back but when I looked up into Ms. Johnson’s beautiful but stern features, I got butterflies at the mere idea of rebellion. Finally, I finished the bottle of milk and she slowly withdrew it from my mouth, a line of drool connecting the nipple to my lips as she pulled it away. I thought she’d let me up but with a cruel smile, she produced another baby bottle, also full of milk!

“No—no…” I whimpered again but with a confident smile, she brought it down and coaxed it between my lips and held it there, forcing me to submit once again. I felt the warm liquid trickling into my mouth and I sobbed with defeat. My tormentor knew how weak willed I’d become and her gorgeous smile was filled with victory for dominating me so fully.

“That’s it…” she coaxed me, “…That’s mommy’s baby…Drink your milk Chrissie, and then it’s naptime for my little panty princess.”

I sucked miserably, even though my stomach was completely full of the babyish drink. Meanwhile, Timmy was looking back at me with half closed eyes, his mouth sucking greedily now at the massive breast pressed against his face. He was breathing hard through his nose and Crystal’s sexy hand was stroking the front of his diapers which had the obvious effect of making the sissy giddy with excitement. His face and chest were bright red and although I knew he was tremendously embarrassed by the whole situation, I also knew he was deeply turned on by it all too. Crystal’s deep cleavage was only an inch in front of his nose and I knew he had a perfect view of her other bountiful melon, held delicately by the half cup of her bra. I heard him mewling with unbridled passion and Crystal was saying sweet things as he sucked her big breast for all he was worth. Suddenly, he moaned out loud and his head rolled back as he came forcefully in his diapers. Gasping for breath, Timmy gazed back at me placidly, overcome by the intensity of his climax. Crystal smiled and brought his head between her two huge mammaries, allowing him to snuggle in her deep cleavage while he slowly recovered.

And that was when something inside me snapped. My tiny little wiener was sore and painful from trying to become hard within my own diapers and with all the sexual stimulation I was being forced to endure, I just couldn’t take it any more. I jumped off of Ms. Johnson’s lap and grabbed Timmy by the shoulder, jerking him away from Crystal’s comforting bosom. With a sudden impulse of anger I didn’t realize I had within me, I slapped Timmy on his groggy face, as punishment for an orgasm that had been denied me.

He immediately burst into tears and began crying like a baby, holding his cheek in his hands while the two women looked at me in utter shock. Ms. Johnson however, quickly recovered, and she jerked me around with a jolting grip of my wrist.

“You’ve just earned yourself a nice, hard spanking,” she said tersely, and she stood up abruptly, towering over me fearfully with her high heels.

“It’s not fair!” I cried vehemently in frustration, “it’s not fair!!”

Reaching down, she swatted me harshly on my diapered bottom, landing her hard hand with a loud thud and causing me to buck forward.

“That’s right Chrissie. And now everyone’s going to watch you cry like a baby when I put you over my knee and paddle that sissy bottom of yours.”

She jerked me along as she strode down the hall and into the nursery, the other two not far behind us. Ms. Johnson has very long legs, and I struggled to keep up with her as she pulled me along behind her. Looking down, I saw how shapely her calves were and the confidence with which she walked in her five inch sandals. I began crying softly, knowing the terrible punishment that was awaiting me, just moments away.

As we entered into the warmly lit room, Ms. Johnson reached over and picked up the wooden paddle before sitting down in the straight backed chair next to us. Hitching up her skirt, she pulled me over to her, ordering me to hold up my dress so she could reach underneath and pull my plastic panties down. By now, Timmy was in the room and he was watching me with grim satisfaction, still rubbing his sore cheek. With several sharp, angry tugs, Ms. Johnson yanked my pretty panties down my legs and around my ankles.

“Chrissie. Before I pull you over my lap for your spanking, I want you to apologize to Timmy for your behavior,” she told me, her eyes blazing with fury.

I was blubbering with fear as I looked from her strong, dominating features, to Timmy’s.

“I-I-I’m s-sorry, Timmy,” I sobbed pitifully.

“Timmy, if you’d like, you may slap Chrissie the way he slapped you,” Ms. Johnson told the effeminate boy.

Without hesitation, he stepped forward and slapped me as hard as he could, although that wasn’t very much given what a weak sissy he was.

“OOUCHH!” I cried nonetheless and I held my hand to my own stinging cheek.

“And now it’s time for you to pay the piper,” she said as she pulled me over her firm lap. I struggled weakly as I fell forward, squirming over her smooth, bare thighs while she reached for the pins holding my thick diapers in place.

“No—no—I don’t want a spanking!” I wailed as she drew back the soft cloth covering my rump.

“You should have thought about that before you started misbehaving,” Ms. Johnson snapped as she pulled my diapers back, pushing them between my flailing legs.

I squirmed in terror as I looked up to see Crystal, her thin arms crossed over her massive bosom with a look that said I was getting exactly what I deserved.

The first slap of the paddle landed squarely across both cheeks, right in the middle of my still pink buns and I howled with pain, kicking wildly.

SMACKK!! WHACKK!!

Ms. Johnson swatted each cheek individually with great force, using her strong, toned arms to deliver a harsh, resounding impact. I wailed helplessly, the tears streaming down my face as she kept up a steady, punishing rhythm, slapping each round, tender cheek, once, twice, then both at the same time. The sting was incredible and I slapped the floor in anguish, wishing I could somehow alleviate the intense pain.

SMACKK!! WHACKK!! SMACKK!! TH-WHACKK!!


She wielded the hard oak paddle mercilessly, bringing it down again and again on my soft, pliable bottom. It jiggled and yielded miserably to each punishing slap as I bawled my eyes out, kicking and thrashing each time the paddle blistered my youthful fanny. Finally, I surrendered and lay there in abject defeat, passively taking my spanking while Ms. Johnson turned my scalding bottom into two cherry-red globes of fire.

SMACKK!! WHACKK!! CRACKK!! SMACKK!! WHACKK!!

I could barely make out Crystal through the tears filling my eyes but she looked immensely pleased, seeing a babyish sissy like me crying and getting a good, hard paddling.

Finally, the painful ordeal at last ended. I lay over her lap, my breath coming in ragged sobs, as she slowly brought my diapers back up and pinned them back into place. I was too ashamed to look at anyone as she helped me to my unsteady feet while I bawled like a baby in front of everyone.

Ms. Johnson looked over at me severely, the paddle still clutched tightly in her hand.

“Have you learned your lesson, Chrissie?” she challenged me.

I couldn’t speak coherently but I blubbered an acknowledgement and nodded my head, tears streaming down my face in profusion.

“Good. Because I won’t have any fighting in my house—is that understood?”

I was afraid to look into her stern eyes but I nodded my head again, trying to answer her through my crying.

“You’re a little sissy who wets his diapers like a little baby,” she scolded me severely, And I’ll decide when, and if, you ever deserve to have an orgasm—is that understood?”

I sobbed again in agreement as she began roughly tugging my plastic panties back up my legs.

“You’re going to be in diapers for a very long time, so you might as well get used to being treated like a baby.”

I cried openly, feeling full of self pity and I think even Timmy felt sorry for me because he came over and hugged me, kissing me tenderly on the cheek.

“Its okay, Chrissie,” he whispered to me.

I threw my arms around him and hugged him, crying hard on his shoulder as the stinging in my diapers continued to make itself painfully felt.

Crystal smiled and came over to put her arms around both of us.

“That’s much better. Now why don’t you two sissies kiss and make up.”

Wiping the tears from my face, I leaned forward and kissed Timmy softly on his warm mouth, even as I sobbed in defeat.

“Alright babies,” Ms. Johnson said as she stood up, “let’s get you two into your cribs--you’ve had quite a day already.”

Tearfully, I stood there while Ms. Johnson unbuttoned my dress and removed it, hanging it up in the closet while she brought out a pink and peach colored onesie, decorated with Birdseye lace. She put the soft garment over my head and brought it down over my outstretched arms, lowering it over my torso and down to my waist. I winced as she pulled the front and back of it tightly across the fat thickness of my diapers, since it rubbed my blazing bottom closely, and snapping the row of three snaps between my inner thighs. The onesie had an elastic waistband that hugged my middle section and gave me a distinct bell shape as it hugged my embarrassing diapers. Looking down at the big bulge around my hips, I could see the Birdseye lace that surrounded my legs and waist, giving me a very babyish look.

Ms. Johnson removed my mary janes and lowered the rails on my crib, guiding me onto the vinyl covered mattress with soft words of encouragement. She tucked me in and then pulled up the soft pink baby blankets around my chin, after she handed me my teddy bear.

Looking across to Timmy, I saw that busty Crystal was doing the same to him and Ms. Johnson finished by pushing a big pink rubber pacifier between my lips.

“Nightey-nite, babies,” she said as she turned out the light but left the door open.

I sucked desperately on my pacifier as I shifted onto my stomach, still crying softly to myself. My bottom felt like a five alarm fire and I knew for sure that I’d never act up in Ms. Johnson’s house again.

　

　

　

…..three months later…

　

I sat at my vanity, carefully applying my make-up as I waited for Ms. Johnson’s summons. Today was the day when my mom was coming back from Europe and she would be finally taking me back home. Ms. Johnson wanted me to look very proper for her arrival and I was very careful in the way I did myself up. After a light layer of foundation, I had put on a soft blush and just a hint of pink eye shadow. Lastly, I put several glossy coats of bubble gum pink lipstick across my full lips which added considerably to the illusion that I was a girl.

Smacking my lips together, I sat back and looked at myself in the mirror, evaluating my efforts.

My longish hair was tied up in two sassy pigtails, the base of each being secured with a big pink floppy bow of its own. Ms. Johnson had picked out an Alice in Wonderland dress for me to wear and the short puffy sleeves accented my skinny arms, while the short ruffled hem would keep me busy ensuring it didn’t creep up in back to expose my pretty rumba panties. After changing my diapers in the morning, Ms. Johnson had dressed me in some glittery white tights and Mary Janes, after which she made me step into a lacey pair of pink rumba panties, silky and delicate, yet large enough to stretch over the fat bulkiness of my diapers. The three rows of bouncy ruffles across the seat added to the babyish feeling that was never far away anymore.

Just then, Ms. Johnson appeared in the doorway, looking beautiful, yet stern and imperious at the same time.

“Your mother has arrived, Chrissie. Stand up and let me take a look at you,” she ordered me.

“Yes Ma’am,” I replied submissively, as I stood up and held the edges of my dress delicately.

“Turn around, Sissy,” she told me, and I bashfully rotated to show her all sides of me.

“Have you wet yourself?” she asked bluntly, without offering any compliments on how I had prepared myself.

“No Ma’am,” I said quietly.

“Come along then,” she said as she reached down to take my hand.

She pulled me along down the hallway, her high heels announcing our presence as we made our way out to the living room. With her superior height, and quick, confident gait, I felt like a little girl being led out to be shown off to her mommy. As soon as we turned the corner, I spied my mom standing in the middle of the room, with an attractive, well endowed woman beside her. Despite my best efforts, I found myself blushing hotly as I bent down to give them my best curtsy.

“Hi Mommy,” I said respectfully, keeping my eyes respectfully downcast and demure.

My mom smiled at me and came forward, holding me closely and hugging me warmly.

“Well!” she exclaimed, “You certainly have changed—and much for the better!”

“Thank you, Mommy,” I replied.

I felt her hand reach down and squeeze my thickly diapered bottom, confirming her suspicions about me.

“Chrissie, go fetch us some tea while your mother and I discuss things,” Ms. Johnson said dismissing me.

“Yes Ma’am,” I answered as I bowed to her and quietly left the room. I made a surreptitious sidelong glance at the other stranger in the room as I went to the kitchen to look at the pretty female that I hadn’t been introduced to yet. She looked to be in her late twenties, with a fantastic body and long, luxuriant, auburn hair. I found her to be stunning in every way and although it was extremely ashamed to be exposed to her in this way, I looked forward to finally meeting her.

While I was preparing the tea set for the three of them, I did my best to listen in on their conversation out in the living room. Ms. Johnson was telling my mom about my progress under her tutelage, making no attempt to leave out any humiliating details.

“When Chrissie first came here, he had a big problem with masturbation,” she was explaining, “But I’ve got that all taken care of now. He wears a chastity restrainer underneath his diapers that prevents any sort of mischief from the little sissy. Of course, young boys being what they are, I knew it was necessary for the sake of his health that he should get some kind of relief from time to time. So I’ve taken the step of milking him once every week—that eliminates the nasty semen he’s built up while still depriving him of any kind of orgasm.”

“Frankly I’m amazed that you were able to achieve so much,” my mom said in obvious admiration, “He was such a stubborn little boy before I left.”

Ms. Johnson chuckled with amusement.

“Oh believe me—that kind of bluster doesn’t last long around here. You’ll find that he’s a changed boy—docile, obedient, polite, and respectful. I think you’ll be very pleased with the results.”

“I saw that he’s still wearing diapers,” my mom pointed out, “does he still need them during the daytime too?”

“Yes, unfortunately so,” Ms. Johnson sighed wearily, “We made a try at potty training him but he just couldn’t manage to stay dry, even during the day. I’m afraid some little boys just can’t be without their diapers and plastic panties and Chrissie is one of them.”

“Well, I guess I really didn’t expect any different from him, he’s always been such a sissy,” my mom admitted.

“Yes, he certainly is,” Ms. Johnson agreed, “I could tell that right off, from the first time you brought him in—he seemed like such a prissy, delicate, immature little boy, still wearing diapers like a little toddler. I’m afraid his prospects for landing a girl some day are remote, at best. What he needs is someone who can give him the discipline he so badly needs—a firm, maternal hand that’s not afraid to blister his bottom with the paddle when he misbehaves.”

As I stood in the kitchen, my face, ears and neck were blushing a bright red as the two of them discussed me in such belittling terms. It was as if they were talking about a three year-old, rather than a young man nearly sixteen. However, the tea was ready to serve and I didn’t dare dawdle—I knew all too well the consequences for making Ms. Johnson angry. Placing the cups and saucers on a tray, I minced back into the living room, the bulky thickness of my diapers preventing me from walking with any kind of grace.

“Have you had to use the paddle frequently?” my mom asked, ignoring me as she took one of the cups I silently offered her.

“No, not as much anymore,” Ms. Johnson said as she studied my service to them with a critical eye, “He gets spanked once a week now, on Sundays, whether he’s been good or bad. We review his behavior for the past seven days and then I take him over my lap to correct his errors.”

“Does he always warrant a hard spanking?” my mom asked curiously.

“No, not usually. But I feel a good paddling helps clear the air and helps him to know his place. I also think a good cry is good for him, as it is for all sissies. He doesn’t like his spankings--believe me, but he’s a much better little boy for them—aren’t you Chrissie?” she said as she faced me.

“Yes Ma’am,” I immediately replied. I knew better than to contradict her, especially since I feared she might feel tempted to give my mom a demonstration of the power of her paddle.

“I’m sure you’re right,” my mom said in agreement, “which is why I’ve hired Jordan here as Chrissie’s tutor and nanny.

“Nice to meet you,” Ms. Johnson said warmly as she reached over and took her hand.

“I’m honored to meet you,” Jordan replied sweetly, “I’ve heard so much about how you’ve turned problem boys around. I only hope I can do as well when Chrissie comes home.”

“Oh, you’ll do fine,” Ms. Johnson assured her, “Just keep his paddle close at hand and you won’t have any troubles at all. Chrissie may seem like a grown up sissy, but he’s really just a big baby inside. He usually starts crying the moment I put him over my lap.”

The women giggled at that revelation while my ears burned in shame. I was required to sit in my chair, with my hands placed in my lap and submissively await Ms. Johnson’s summons for whatever she might require.

“Sounds like he’ll be a cinch to control,” Jordan said with a chuckle, “I have quite a bit of experience with disciplining children, so a big sissy in diapers shouldn’t present any problems.”

“In my opinion,” Ms. Johnson offered sagely, “You would do well to give him a spanking right now—just to establish your authority with him.”

My heart skipped a beat and I gulped hard as I saw Jordan looking intrigued with the idea.

“What do you think Mrs. Brooks?” she asked, turning to face my mom.

“I think it’s a wonderful idea,” she said brightly, as if she were discussing a picnic, “I think it’s an excellent way for you to get to know each other.”

I was biting my lip nervously as Ms. Johnson turned to face me.

“Chrissie?” she said, “Go and fetch your paddle.”

I began whimpering fretfully and I faced my mom, my eyes pleading with her to intervene but she only smiled back at me wordlessly, while I squirmed in discomfort.

“Run along Sissy, and do as you’re told,” Ms. Johnson warned me, “Or you’ll be taking a trip over my lap as well.”

I choked back a sob and stood up quickly, bowing in deference to the boss of the house.

“Yes Ma’am,” I responded.

I trudged back to the nursery, dreading every step I was taking. Today had started out so good and now I was about to be spanked! And for doing nothing! Nothing at all! It was so unfair!

Once in the nursery, I waddled over to my pink dresser, with its Barbie dolls arranged neatly across the top. Hanging from a peg on the wall above it was my paddle, an oval shaped piece of polished wood, 3/8” thick with six large holes in the face of it. I cringed as I held the fearsome instrument in my hand, tears brimming in my eyes. How many tears had this paddle caused me, I wondered to myself, as my bottom twitched nervously. It was large enough to cover both of my buns, yet small enough so as not to be unwieldy. And I knew all too well the skill with which Ms. Johnson could apply it to a particular area, giving it extra attention if she felt the need.

I walked out in a daze, my head hung low as I made my way back to the living room. I wanted to meet this pretty and sexy woman but certainly not in this manner! Would she spank me hard? Would she make me cry? She looked too nice to do that, I thought. Maybe she’d just give me a few practice swats and that’d be it. Maybe she’d even let me keep my diapers on. I hoped and prayed that that would be the case.

Walking slowly into the living room, I went over to Jordan who was now sitting in a straight backed chair and I presented her with the paddle. She looked very sexy with her short skirt and high heels, and the tight, snug-fitting halter top she had on, barely concealing her big, plump bosom. Looking at her brought out strong feelings of inferiority in me and her high heels made me fearful.

“Thank you, Chrissie,” she said, beaming a warm smile up at me, “You and I are going to be spending a lot of time together so I think its only appropriate that we should start things off right, with a nice, hard spanking.”

With her pretty smile and the way she said it, she made it sound like she were talking about giving me a bath, instead of a painful and humiliating punishment.

“From now on, I want you to address me as ‘Aunt Jordan’ or ‘Miss Jordan’. Okay Honey?” she said sweetly.

“Yes Miss Jordan,” I quivered nervously before her.

Suddenly, I felt the front of my diapers growing warm and wet and I realized belatedly that I was uncontrollably flooding them at the worst possible time. Once a full stream had started, it was quite impossible to stop it and my face turned bright red.

“Oh!” I squealed and my hands went down in a futile attempt to hide my shameful act. Somewhere over the course of the last three months I had lost whatever marginal control I had once had over my bladder and once I started, it was impossible to stop peeing until my bladder was completely emptied. As I stood shifting from one foot to another, my diapers grew heavy with the accumulated pee until it began to seep between my legs and up into my seat. My tights, rumba panties and baby pants all ensured that my bottom cheeks felt the full effects of my wetting as the cloth absorbed it and spread it all around. As the women watched me humiliate myself, I stood there, my face the color of crimson, as I waited for the last bit of pee to finally come. Oh, how I hated my childish incontinence!

Ms. Johnson shook her head in dismay.

“I’m afraid our little sissy has just demonstrated why he needs his diapers so badly,” she said scornfully, “Do you need me to take over, Jordan?”

My stunning tutor didn’t pause for even a moment to reconsider.

“Not at all, this is all part of getting to know my little baby,” she said as she smiled warmly at me. Placing the paddle on her skirted lap, she waited silently for me to stop peeing with the patience of someone who’s used to dealing with toddlers.

“All done?” she finally asked in her sweet voice.

“Uh-hm,” I mumbled as my face burned scarlet.

Pulling her own skirt slowly and teasingly back to reveal her sexy, creamy thighs, she looked deep into my eyes and I could feel her superior personality overwhelming me, making me feel every bit the naughty little boy.

“Chrissie, this is only the first of many spankings you will receive over my lap. I know this going to hurt you but it’s for your own good, okay Honey?”

“Yes, Miss Jordan,” I sniffled.

“You can cry as much as you want to and feel free to kick your legs—I know you are a big sissy and you can’t help it. And after we’re done, we’ll go and change your wet diapers, okay?”

“Yes, Miss Jordan,” I sobbed.

I felt defeated by this pretty nanny before she’d even pulled my diapers down but I knew that was what was coming next would be even worse.

“Chrissie? I want you to hold your dress up and out of the way—can you do that for me, Honey?” she asked in her pleasant, kindly voice.

“Yes, Miss Jordan,” I replied meekly.

Grasping the ruffled hem of my dress delicately, I pulled it up to reveal the thick, embarrassing diapers I was wearing underneath, now soaking wet with pee. Jordan reached over and put her long nails underneath the waistband of my satiny rumba panties, snaking them off the bulk of my diapers with ease as she lowered them to my ankles.

“You’re wearing such pretty panties, Chrissie,” she remarked sweetly, “But don’t you worry, I’ll make sure we put them back on after you’ve been paddled.”

My heart skipped a beat at her warm manner, which contrasted so dramatically with what she was doing.

Next, she did the same with my glittery tights, working them over and down, despite the tight elastic waistband that held them up. She encircled my calves with her slim hands as she lowered them down to my ankles, just above my gathered panties. Looking up at my fear filled face, she smiled again reassuringly as she reached over and put her long nails inside the waistband of my pink baby panties, working them around and gradually peeling them off of the sopping wet cloth of my diapers, until they were free of the bulk. Then she pushed the dewy panties down until they were also encircling my ankles.

“Okay Chrissie,” she told me, “It’s time for you to get spanked.”

A tear trickled down my face as she gently pulled me over her bare lap. I landed with a wet and humiliating squish and I was deeply ashamed that this beautiful woman had to feel my incontinence so intimately on our first meeting. I whimpered in fear as she began patiently removing the diaper pins holding the wet cloth together. She even began humming a tune while she pulled my diapers back, exposing my bare, wet bottom to everyone present.

“P-please—please don’t spank me hard,” I sobbed fearfully.

“There, there,” she said in almost a whisper, “A good cry is just what mommy’s little baby needs.”

Quivering with anticipation, I felt her stroking my damp cheeks with the paddle, in an almost soothing manner.

“You have a very nice bottom, Chrissie,” she remarked softly, “And I’m going to enjoy spanking it, nice and hard.”

With that, she raised the paddle up high and brought it down again with a biting wallop, searing my dewy buns with a shockingly harsh impact. I wailed loudly in pain and kicked my feet frantically as she brought it down again, slapping my right cheek forcefully and leaving an angry red oval tattoo. I gasped helplessly at the severity of her assault, just as the paddle came down to blister the other cheek, in a vengeful, punishing delivery.

Kicking my feet wildly, I burst into tears as she kept up a carefully measured spanking, designed to make me savor every stinging, blistering slap of the paddle. My cheeks were on fire and I howled miserably as she took her time, swatting every square inch of my blazing buns with a strength I didn’t think possible. My soft, tender buns danced each time the hard oak paddle landed, jiggling merrily before it landed again to instill this painful, humiliating lesson.

I cried like a baby, slapping the floor with my hands as she continued the paddling without pause. How was it that women could so easily take advantage of me and punish me? I didn’t know but as I lay across her lap, feeling the fury of the paddle on my scorched bottom, I knew that I would be taking orders from her in the future.

At long last, the terrible spanking ended, and I lay in place, bawling uncontrollably in front of everyone. With gentle kindness, Jordan carefully helped me to my feet where my wet diaper fell heavily to my ankles, exposing my miniscule genitals to her smiling face. She looked down at them and suppressed a giggle, flicking my tiny penis with the long nail of her finger while I cried in shame, covering my tear stained face with my hands.

“Are you ready for your diaper change now, Chrissie?” she asked me.

I sobbed loudly and nodded my head, completely defeated by this knockout. I knew I would never question her authority and I would always do what she said.

“Okay, can you carry your wet diapers, Honey?” she asked tenderly, “We’ll put them in your diaper pail when we get back to the nursery.”

I nodded again and reached down to pick up the heavy, pee-soaked cloth as I shuffled after Jordan, taking baby steps since my panties and tights were still gathered around my ankles.

“Come on little baby, let’s go change your diapers,” she said gaily as she held my hand to pull me along.

As I continued crying pathetically, I couldn’t believe how hard she’d just spanked me! Looking over my shoulder and pulling up the back of my frilly dress, I could see my round bottom was a bright, fiery red, with purple blotches and raised skin. Her manner was soft and comforting but she wielded the paddle like Ms. Johnson! I sobbed woefully as I pondered my future with this woman, bent over her knee getting my bottom spanked on a regular basis.

When I reached the nursery, Jordan was already waiting for me with a fresh set of bunny soft diapers and the diaper rash crème. She took my hand tenderly and sat me down on the changing table where I erupted in a fresh set of tears.

“There, there Baby,” she said as she brought a pacifier up to my quivering lips, “Why don’t you nurse on this for awhile, maybe it’ll make you feel better.”

I accepted the big rubber nipple of the pink pacifier as she passed the plastic loop over my head.

Using baby wipes, she cleaned my diaper area gently, before taking a generous handful of crème and smearing it across my stinging, candy-apple cheeks.

“Now you’ve learned what’ll happen if you disobey me, haven’t you Chrissie?” she said with her warm smile.

I nodded my head, still crying as I sucked the fat nipple filling my mouth.

“You see, I like to spank sissies, especially ones like you that are still wearing diapers like a little baby,” she said as she coated my blazing bottom with the crème, “And I’m going to make sure you get at least one good, hard spanking every week.”

I swallowed hard and sobbed, realizing she had every intention of continuing Ms. Johnson’s practice of weekly spankings.

Jordan reached over and picked up a big rubber butt plug, dipping it deeply in a jar of nursery jelly before positioning it below me.

“Hold your legs up, Sissy,” she instructed me as she held the vaseline covered plug at the ready.

Since I was on my back, I raised my legs again which spread them wide for her intentions.

“That’s a good little boy,” she said sweetly as she began working the greasy plug into my back hole. I pouted and squirmed as she twirled it around, pushing it in and out to get me used to the fat tip.

“Spread your legs wider, Sissy….that’s it….that’s mommy’s baby…there you are…” she coaxed me as she put more and more pressure on it to push it in. I moaned and shook my head no but she placed her other hand on my thigh and pushed harder against with the plug, unwilling to let me escape. Finally, as I let out a cry of pain, it eased past my defeated sphincter and slipped inside as my hole closed around the shaft of it, locking it in place until she decided to remove it.

I was whimpering like a little girl as she smiled down at me in satisfaction.

“That’s a good little boy,” she said cheerfully, “And that should take care of your messes until we can get you home.”

Taking the thick stack of diapers, she raised me up and slid them beneath my sticky rump, setting me down gently upon them. As I wiped away my tears, I gazed at her big, swaying breasts that were literally bursting from her halter top.

“You like big breasts, don’t you Chrissie,” she said with a smile as she caught me staring at her chest.

I nodded my head yes meekly and she beamed down at me warmly.

“I thought so,” she said as she pulled the thick cloth of my diapers up and between my legs, pinning either side securely with pink clown pins, “but if I catch you staring at them again, you’ll be going over my lap for another lesson in manners—do you understand me?”

“Yeth, Mith Jowdan,” I lisped as I sucked on my pacifier. I was frustrated to discover that this pretty woman, despite her kind, loving manner, was every bit as strict as Ms. Johnson.

Pulling up my plastic panties, she briefly wiped the still wet insides of them with baby wipes before pulling them up my legs. I hated having to wear panties that had been wet in previously because the elastic legs bands would always remain cool and damp around my thighs. I shook my head in protest and whimpered stubbornly but she ignored me as she continued to pull them up, wrestling them over the bulky soft cloth of my diapers with her finely manicured hands.

“I know these are a little wet, Sissy, but that’s too bad. You’ll just have to get used to it,” she told me.

I pouted in silence as she powdered between my legs and pulled my tights back up and into place, effectively ending the issue.

I was somewhat surprised when she began pulling my Alice in Wonderland dress off of me and I whimpered in angst, sounding like a little girl whose doll was being taken away.

“One thing Ms. Johnson and I may disagree on, are the clothes you’re entitled to wear. You see, I think that anyone who’s fifteen years old and still wetting his diapers like a baby--should be dressed like a baby.

“I’m going to make sure everyone knows that you wear diapers Chrissie—starting right now,” she said emphatically, “You’re going to come home in the most babyish outfit I can find for you—one that clearly shows off your diapers and plastic panties to anyone who might be nearby.”

I cringed and choked back another sob as I pondered how my future was shaping up with this busty disciplinarian eager to humiliate me.

Standing up, Jordan went over to the closet until she found a very short baby dress with frills and frills all over it. It was pink with white satin lace and a hemline that I knew would leave my fat diapered bottom fully exposed. I pouted as she worked my arms through it and buttoned it in back, checking the fit to make sure my diapers were clearly visible. Once she was satisfied, she pulled me to my feet and pulled my lacey rumba panties back into place while I sucked my pacifier in frustrated silence.

“You might as well get used to that as well,” she said as she looked down on me and crossed her arms across her big breasts, “Because I’m going to be taking you out in public all the time, so people can see what a fifteen year old boy who wears diapers and baby clothes looks like.”

I blushed hotly at the thought of what that would be like and I stamped my feet in frustration as I realized how powerless I was to prevent her from doing what she wanted with me. And I could feel the fat rubber butt plug stuffed inside me, serving to remind me exactly who was in charge here. She looked down on me with complete superiority and confidence, knowing full well there wasn’t a thing I could do to stop her.

“Come on Chrissie,” she said taking me hand, “Let’s go show your mommy what a big sissy you really are.”

Dominated and defeated, I waddled out behind Jordan where my mom was waiting in the living room for us with her car keys in hand. When she saw me, she began nodding her head in obvious approval, clearly agreeing with Jordan’s methods.

“Well,” she said as she looked me up and down, “Looks like you’re in good hands. Come along Chrissie, it’s time to go home.”

With an uneasy feeling, I said goodbye to Ms. Johnson, whose strict rules I had had to live under for the last three months. I had hoped I might get to live the life of a little girl at least, but now even that was being taken away from me. It looked like diapers and the life of a baby were what I could look forward to when I got back home.

I guess I had always been afraid to admit that I was a sissy, but now, there was no point in denying the truth. I needed my diapers and I needed the strict hand of a superior woman to ensure I toed the line. I wasn’t a man and I knew I never would be one. Rather than try and be something I knew I could never be, the only thing that made sense was to embrace my sissyhood. It was time for me to start all over, as the big baby everyone knew that I was but which I had always been afraid to admit to.

Looking over at the busty, dominating profile of Jordan, I knew I would be feeling the sting of her paddle on a regular basis but I realized deep down…she was just what this sissy needed.

　

　

　

The End