The Babysitter's Surprise

The Babysitter's Surprise

　

I sat in my mom's car with feelings of both excitement and anticipation as we made our way to our friend, Jordan's house. My mom had errands to run and she didn't want me pestering her so that meant I would be spending the afternoon at my babysitter's house. It was humiliating having to be babysat by an adult, especially at my advanced age of thirteen, but my mom insisted on it. She didn't trust me to be left on my own, partly because she thought I was too delicate to fend for myself and partly because she still thought of me as a child. I suppose in my more honest moments, I realized that she thought of me as a bit of a sissy, just as a lot of people seemed to. And I knew the fact that I was still wetting the bed didn't help things but from my adolescent perspective, I chafed at her smothering maternal control.

Still, I felt a sense of eagerness as my mom's car pulled into my babysitter's neighborhood.

Jordan, my babysitter of three years, had become the focus of all my boyish fantasies. She was tall, slim, and drop dead gorgeous with long, luscious brown hair. I wasn't sure how old she was exactly but I was guessing in her late twenties. At my tender age, I could never hope to be considered her peer but that didn't stop me from lusting after her constantly. My budding sexual awareness was fueled in no small part by Jordan's habit of dressing not only casually but with a minimum of clothing. To be sure, the warm summer weather helped the situation but as I grew into puberty, I had become increasingly aware of her low cut tops that revealed a jaw dropping amount of cleavage between her big, beautiful, round breasts. I had lost count of how many times I had stroked myself to a shattering orgasm while treasuring images of her sexy body in my mind's eye. I sometimes wondered if she had any idea of the depth of my feelings for her although I suspect she might have taken exception to some of my fantasies in which she was the prime focus of my attentions.

As we pulled into her driveway, I was looking forward to some quality time alone later as I took my usual opportunity to satisfy my ever present sexual needs.

We walked to the door and knocked but when Jordan greeted us in her entryway, she took my breath away.

Wearing thin pink shorts that looked like they were spray painted on to her trim physique, I marveled at her fabulous legs, so smooth and silky. But her clinging white top was what riveted my attention and caused me to openly stare in awestruck admiration. Already low cut as it was, Jordan had unbuttoned the top of it and the wonderful fullness of her breasts were pushing mightily against the stretchy fabric, eliminating any wrinkles except for the ones down the center that only emphasized the strain between her twin melons.

She greeted me warmly but I could only stammer incoherently as I stared helplessly at her unbelievable feminine curves. Her delicately manicured hand reached down to my chin to redirect my attention to her stunning face and pretty eyes.

"Up here, Sweety," she chided me with an amused giggle.

I blushed at being caught so blatantly and tried to will away the embarrassing redness of my cheeks as she made small talk with my mom.

Throughout my neighborhood at home, I had bragged endlessly about my relationship with Jordan although I'd never once used the term 'babysitter' in such discussions. I knew my friends probably thought I exaggerated both her beauty and the depth of my relationship with her but to see her was to believe a goddess lived on earth.

At last they finished and as my mom made her departure, I was happy to once again have Jordan all to myself.

"Come along, Ethan," she said as she reached down to take my hand, "I have something for you in my room."

My heart missed a beat and then another. Did I hear correctly? What could she possibly have gotten for me? Was it some kind of present? Or something of a more amorous nature? I practically skipped beside her as we made our way the short distance down the hall and into her feminine bedroom. My imagination was cooking up wild, fantastic ideas of what she would do to me, each one growing more ambitious than the next. At the same time, my little penis was already starting to throb and as I glanced sideways at her sexy profile, I wondered--not for the first time--what it would feel like to stroke the soft curves of her mesmerizing breasts.

When we entered the room, I saw a few odd items arranged on her bedside stand; a number of clear plastic pieces, who's purpose I couldn't fathom, a bottle of baby oil, a wash rag, and strangely, a small lock. I couldn't for the life of me think of what it was all meant for.

Bending down before me, I gaped in awe and rapture, staring down the front of Jordan's snug fitting top as she reached for the waistband of my jeans. Distracted as I was, I was barely aware of the fact that she was unbuttoning my pants and unzipping the fly. I was so caught up in ogling her soft, plump breasts, inches before my eyes, that it wasn't until I felt my jeans slipping down that I stuttered out a cry of surprise.

"Wha-what are you d-doing?" I quaked.

"Something I should have done a long time ago," she said vaguely but firmly as I felt her cool fingers slip inside the waistband of my Superman underwear.

"Wa-wait!" I cried helplessly but as usual, she ignored my protestations and I felt her pull my undies down, exposing my bashful, quivering genitals. Blushing with embarrassment, my hands dropped down to cover my hairless privates although this was certainly not the only time Jordan had seen me naked. Insistent as she was on maintaining her bedding, I was used to Jordan putting me in diapers before my naptimes. It was extremely humiliating but fortunately, no one besides my mom knew of the practice and I was determined to make sure it stayed that way.

Still, there was something about her purposeful nature that caused red flags of warning to go off in my head. For one thing, it was too early for my nap and the other thing was that one of the plastic objects on the nightstand was oddly shaped like a short penis. What that boded for me, I couldn't guess but it couldn't be good.

Taking a ring shaped piece with an opening at the top, Jordan pulled my genitals forward slightly and slipped the ring in behind them.

"What are you d-doing?" I repeated.

Being passive and submissive by nature, it simply didn't occur to me to try to physically resist her.

"Ethan, I've known all about your masturbating habit for quite a while now and it's time I put a stop to it," she told me matter-of-factly.

Taking a couple of other pieces, she mated them with the ring to complete the circle and then pushed a center pin behind the top of the ring.

Even as I tried to grasp the implications of what she was doing, my mind was still reeling from her sudden, shocking revelation. My face burned with shame at the knowledge that she knew about my most private of activities and I was quick to hotly deny it.

"I-I-I don't do that," I stammered, unable to say the actual word.

I knew I didn't sound convincing but I wasn't about to admit she was right.

"We both know you do, Ethan, the moment I turn my back on you," she said with certainty, "I've seen the naughty mess you leave in your underwear and diapers and now this little device will prevent any further mischief."

Waves of shame washed over me as her naked words sank into my brain.

Pouring a small amount of baby oil in her slim hand, she wrapped it around my wilted penis and pulled down the short length of it, coating it in oil. At any other time, I would have been thrilled beyond words to have her touch me in that way but at the moment, my heart was beating wildly in panic and humiliation.

Without delay, Jordan quickly grasped the clear tube and positioned it before my slippery wiener.

"Say hello to your new friend, Ethan," she said merrily as she slid the short tube over the end of my penis.

"No--don't...please," I whimpered but I watched helplessly as my little noodle slipped down into the tube, fitting perfectly inside and filling it to capacity. I could easily see that it would limit any growth to no more than an inch and a quarter, considerably shorter than my normal erection.

Ignoring my plaintive whimpering, Jordan mated the tube with the ring and slipped the lock through the end of the pin, clicking it closed with an air of finality.

"There you are," she said with a satisfied smile, "All safe and secure--that will put an end to your masturbating once and for all!"

My cheeks blushed red hot in shame but I stood there too embarrassed for words.

"And since we already have your pants off, we might as well get you diapered and ready for your nap," she said nonchalantly.

"B-but---it's not even close to that time!" I cried bitterly, finding my voice again.

"I know, but it'll save having to do it later," she explained simply as she led me over to the vinyl pad she'd already laid over the bed.

I pouted angrily but helplessly as she sat me down on a stack of soft, fluffy diapers, feeling the resentment boiling inside me like a cauldron. What was going on today??

Jordan took the baby powder and began sprinkling it liberally around my crotch, between my legs, and onto the cheeks of my youthful bottom. Despite my smoldering anger, I couldn't help the intense sexual excitement I felt as I gazed down the plunging front of her top. Being diapered by Jordan had always been a tremendously arousing experience for me for as long as I could remember. My very first orgasm had occurred one afternoon when she'd diapered me prior to my nap. The combination of her attention, the intense intimacy of the moment, and having her succulent, mouthwatering breasts hanging before me drove me wild. Even as humiliating as it was being put into diapers at my age, I still looked forward to it knowing that immediately afterwards, once I was alone, I'd be stroking myself to an eye-crossing orgasm.

Now, as Jordan began her familiar routine with me, her big breasts swung heavily before me and my penis twitched with nervous excitement. In no time at all, I felt the confining restriction of the chastity tube she'd placed on me as my wiener struggled in vain to become erect.

Squirming in place, I whimpered with sexual frustration.

Ignoring my angst, Jordan quickly brought the front of the diaper up and positioned it with the back corner, slipping a pink bunny-headed diaper pin through the two ends. With my feet fishing through the air, she pinned the other side snugly and I watched as she removed my shoes and pants.

Realizing I'd have my diapers fully exposed instead of hidden like usual, I whimpered with helplessness.

"I still don't see why I have to wear these right now," I whined miserably.

"Hush," she shushed me and she produced a pink pair of nursery print plastic panties, gathering them together and aligning the leg holes with my feet.

"Wha--what happened to my usual ones?" I wailed.

"They got torn, Ethan, so you'll just have to make do with these. Fortunately, they just happen to be in your exact size," she explained patiently.

I was crushed with shame. Normally, she dressed me in plastic pants like the ones my mom put me in, plain white, with no designs. But these were so little girl babyish, it put a whole different perspective on my experience.

"But I don't wanna wear those!" I cried bitterly as she began tugging them up my legs.

"Ethan? Do I need to get you a pacifier?" she asked me with a new tone edged with authority.

"No," I replied tersely, pouting in angry silence.

I couldn't believe what was happening! I had never been put in diapers this early in the day and certainly not with pink baby panties! On top of that, my penis was throbbing insistently, completely rebellious toward the feelings of anger and resentment I felt towards Jordan for her treatment of me. I hated myself for wanting her so badly but I was a slave to my desires.

And I cursed myself for being so careless with my masturbating. What was I going to do now?

As she allowed me to sit up, I reached over for my jeans but to my chagrin, she had already started re-tying my shoes.

"Wait--what about my pants?" I said, trying to keep the quiver out of my voice.

"Sorry, Ethan--they'll never fit over your diapers but don't worry--you can just go around like this," she said, gently patting the thick cushiony front of my pink plastic panties, "Besides, no one's going to see you anyway."

Gazing in frustration at my thick, bulging diapers, I had to admit she was right but I hated the idea of walking around with no pants on. It was mortifying!

"I don't like this," I said by way of weak protest but Jordan only ignored me. It was clear she had no intention of changing her mind and in a battle of wills, we both knew who would win. After sprinkling some more baby powder between my legs, she began putting away the diapering supplies and I was free to get up.

It felt strange to stand up. Not only was I not used to wearing diapers anywhere but bed, I could still feel my penis straining in futility against the hard, unforgiving plastic prison surrounding it. Instinctively, I reached down to adjust it but the diapers and the chastity device prevented interference of any kind.

"You can go and play with your toys now, Ethan," Jordan told me as she gave my seat a playful slap and finished putting things away.

I waddled out of the room, my cheeks blazing as the slippery vinyl of my plastic pants rubbed softly against my inner thighs. I felt so humiliated every time I looked down; the playful cartoon characters seem to shout out that I had no control over my bladder and I needed to be diapered like a little baby. I had never really seriously given too much thought about my bedwetting but now I was wondering if perhaps I had become overly comfortable with it.

Walking out into the den, I began to amuse myself as best I could, reading some fashion magazines that Jordan had lying out. I was frustrated and angry, not the least of which was due to the fact that I felt betrayed by the idol of my life. But at the same time, I couldn't get her sexy, busty image out of my mind. Her top today was so exciting and enticing, every minute that passed by made me feel hornier and hornier. I recalled her soft skin, her wonderful scent and her hair, her pretty brown eyes and her full, luscious lips.

Instinctively, I spread my legs and began to gently rub the pillowy soft front of my diapers, desperately seeking some sort of relief. I could feel the usual rhythm of my ministrations, albeit indirectly, but not enough to bring any kind of satisfaction. On the contrary, the more I rubbed myself, the more horny and frustrated I became. My penis was aching and it felt crushed inside the cruel chastity device, unable to be free. After a while, I was forced to give up in utter despair.

I was laying on the floor on my stomach, watching some boring TV show when I heard Jordan coming into the room from behind me. Craning my head around, I saw to my shock, her sister Danielle standing right behind her and I bolted upright immediately.

"Well--who do we have here?" she asked brightly.

Danielle was a few years younger than Jordan and nearly as hot looking as her sister. I had met her before but obviously it had been when I was fully dressed. Sitting here now in my bulging diapers, with the shiny pink plastic panties, I blushed furiously as she beamed down upon me. There was no hiding what I was wearing and somehow, the fact that my shoes were on made it look even more "natural", like this were my usual attire.

As my cheeks burned hot with raw shame, Danielle bent down and smiled at me cheerfully.

"What a cute baby!" she exclaimed cheerfully.

Even though I was flattered in an odd way to get some positive attention from such a pretty woman, her calling me a baby only made me angry and caused me to blush redder.

"I'm not a baby!" I snapped hotly.

Danielle giggled as she looked me over, taking in my thick diapers and bare, hairless legs.

"My friend's baby girl wears plastic panties just like those," she exclaimed as she pointed at my diapers, oblivious to my discomfort.

I felt my eyes filling with tears of embarrassment and my ears and chest burned like they were on fire--I'd never been so humiliated in all my life!

"Ethan--it's naptime for you now," Jordan suddenly announced, "Come on Sweety, let's get you tucked in."

Even though I was desperate to be anywhere else than in this room, my instinct was to resist being sent to bed, especially so early. It was bad enough that at thirteen I was still being made to take naps like a child but now Jordan's hot sister knew about it too!

"But--I don't wanna!" I whined desperately.

"Come along Ethan," Jordan said as she reached down and took my hand, "It's beddie-bye time."

My cheeks blazed crimson at her childish treatment of me but I nevertheless stood up awkwardly. Suddenly, I felt the thick seat of my diapers being squeezed by Danielle and I let out a loud squeal of surprise.

"Oh--I'm so sorry!" she giggled, "I was just checking to see if you'd wet yourself."

I was furious with anger but I knew better than to speak harshly to her. Jordan had a limit to her patience and I could remember one time she had pulled me over her lap to administer a blistering spanking because I had been misbehaving. I didn't want to add that humiliation on top of what I was undergoing now.

The three of us walked down the hall, although I was doing more waddling than walking. Jordan entered the bedroom and drew back the blankets on her bed but before I could climb into it, Danielle had to pat the thickly padded seat of my diapers one last time.

"Sweet dreams, Ethan," she teased me.

Jordan bent down and gave me a kiss on the forehead before turning to go.

Once the door was closed behind her, I was left to sulk in my shame as I stared up at the ceiling in despair. I relived the humiliating scene over and over in my mind, agonizing each time I remembered the look of smug superiority on her sister's cute face.

Yet, despite my anger, once again, my hands found their way down to stroke the soft, vinyl surface of my diapers. How many times had I rubbed myself to a dizzying orgasm in this exact place, splashing my small deposit of cum in the wonderful embrace of these comfy diapers? But now, even that simple pleasure had been denied me and I lay there steeped in frustration and resentment.

At long last, after an hour of tossing and turning, I finally fell into a fitful sleep.

　

　

　

I woke up to the sensation of someone's hand gently squeezing the warm seat of my diapers.

"Oh!" I said startled.

"I'm sorry Honey--I didn't mean to scare you," Jordan told me, "Looks like mommy's little boy wet his diapers again during his nap."

Ignoring my embarrassment and her discovery for the moment, I looked around the room frantically.

"Is Danielle gone?" I asked her urgently.

"Yes Ethan--she left an hour ago."

What a relief that was, I reflected. At least now I could get my shameful diapers removed along with the chastity device she'd put on me. In the back of my mind, I consoled myself with the knowledge that I'd still be able to masturbate freely once I got home.

Taking me over to the other side of the bed, I saw that she had already set up my changing pad but I was confused and concerned by the sight of a fresh trio of diapers that were stacked in place.

Without an explanation, Jordan began peeling my clinging plastic pants off my sodden diaper and unpinning the wet cloth. I bit my lip nervously and fidgeted while avoiding her gaze. Even though I'd been wetting the bed for five years now, it was still embarrassing to have this gorgeous adult removing my pee soaked diapers like I were a toddler. The smell surrounded me and caused me additional pangs of humiliation.

After a quick cleaning of my bottom and privates, Jordan began sprinkling fresh baby powder over me.

"Wha-what are you d-doing?" I squeaked anxiously.

"I'm changing your diapers for the ride home, Baby," she informed me in her sweet voice.

A shiver of panic raced through me as I suddenly realized what she had in mind.

"B-but...I-I don't wear diapers during the d-day," I bleated.

"Ethan--your mommy and I have been talking and we've decided that you need a little more incentive to stop your bedwetting. Maybe the additional embarrassment of wearing diapers during the day will motivate you to stop your childish behavior."

I was mortified beyond words. I'd always thought Jordan was my friend but now she seemed like she wanted to deliberately punish and humiliate me.

Grasping both of my ankles in her hand, she deftly raised my rump and slid the new stack of diapers beneath me. I kicked and whined but with little effort, she quickly pinned each of the sides around my hips and reached over for a fresh set of plastic pants. It was then that I realized my chastity device hadn't been taken off and was at risk of being forgotten about.

"Hey! Y-you forgot to take that thing off down there," I said, pointedly referring to my diapered crotch.

Acting as if she didn't even hear me, Jordan began feeding my thrashing legs into another pair of pink plastic panties.

"Nope. That's staying on permanently Ethan," she told me firmly.

"Wha-what you mean?" I cried, "You can't do that!"

Tugging the plastic panties up my skinny thighs and working them over the thick, bulky cloth around my hips, Jordan fixed me with a firm look on her pretty face.

"Ethan--I've also spoken to your mother about your chronic masturbating habit. As I expected, she was disgusted to learn about it and fully agreed with the chastity device I've decided to put on you. You'll be wearing that from now on to prevent you from playing with yourself anymore."

I couldn't believe my ears! She told my mom??

Blushing bright red with shame, I stood up hastily, my blood boiling.

"I hate you! I hate you!" I blurted out angrily.

No woman was going to get the best of me! I was thirteen years old--practically a man! It was time I finally stood up to this person who I used to idolize with such vigor.

Jordan stood back and placed her slim hands upon her curvy hips, staring down at me as if expecting my reaction. Even without her heels, she stood quite a bit taller than I and her big breasts thrust out proudly before me, mocking me with their adult, feminine superiority.

Stamping my feet in angry protest, I shook my fists to emphasize my defiance.

"You take this thing off me--right now!" I demanded in my shrill, high pitched voice.

"Alright Ethan, you've just earned yourself a trip over my lap," she said matter-of-factly while completely ignoring my demand.

Taking my wrist firmly in her hand, Jordan sat down and pulled me over to her side.

"Stop it!" I cried, trying to wrench my wrist free of her grip but she was far too strong.

With her free hand, Jordan jerked my pink plastic panties down with several sharp, angry tugs, making me wail in distress.

"Stop it! Stop it!" I demanded even as I saw the determined look in her eyes that said there was no going back.

In an instant, she flung me across her lap and I landed with a humiliating flailing of my arms. Part of me still couldn't believe she'd actually spank me but I gasped in shock as I suddenly felt cool air against my bottom. Removing one diaper pin, she made quick work of the other, pulling my diapers back and setting the pins aside.

"Wait!--Wait!" I cried urgently. This was all happening too fast!

Out of the corner of my eye, I saw her reach over and grasp an oval wooden paddle before it quickly disappeared from my view.

"Nooo!!!!--"

--SMACKKK!!

I howled and kicked my feet as her paddle seared itself across my helpless bare bottom.

SMACKKK!!

Just as I found my breath, her paddle landed squarely in the same place, swatting both cheeks with the angry fury of a swarm of hornets. I immediately burst into tears and shook my fists as she swatted me in quick succession with impunity.

SMACKKK!! SMACKKK!! WHACKKK!!


Kicking my legs, I bawled like a baby as her paddle slapped my soft, tender buns again and again. I thought a brief display of tears might dissuade her from spanking me further but obviously, that wasn't the case. I was sobbing like a toddler and her spanking wasn't letting up for an instant.

SMACKKK!! SMACKKK!! WHACKKK!!


Having set the center of my bottom ablaze, she focused her attentions on the still pink sides, slapping and swatting them with equal fury as I cried and kicked in bitter futility. Tears flowed down my face in an endless stream as I beat the floor with my bunched fists.

I belatedly realized how foolish my tantrum had been and how seriously I had misjudged Jordan's strength and willpower. Clearly, she was still the boss and the one who made the rules in this house. I realized that all too well as I sobbed and cried unashamedly.

Having finished blistering the sensitive sides of my buns, Jordan returned to the center of each cheek, swatting each of my buttocks singly and in turn, first one, then the next, although sometimes she'd repeat the same one just to throw me off.

At long last, the terrible spanking was over. I lay over her lap, completely defeated and crying my eyes out.

"Are you ready to wear your diapers home, Ethan?" she asked tersely.

"Yes! Yes!" I wailed incoherently between bitter sobs.

"Do you admit you're a little masturbator?" she continued.

"Yes! Yes!" I surrendered. I was willing to say anything at that point even though we both knew it was the truth.

"Do you agree that you need a chastity device to keep you from playing with yourself?"

"Yes, Ms. Jordan! I do!" I sobbed.

"Good...I'm glad. Because that's exactly what you're going to tell your mommy when she shows up to take you home," she explained.

A fresh sob of defeat escaped from me as I tried to grasp the scope of the life that lay ahead for me. How would I do without masturbating? And how would I cope with wearing my humiliating diapers during the day?

I struggled to come to terms with those thoughts as Jordan re-pinned my diapers and pulled my plastic panties back into place.

"Your mommy will be here soon," Jordan explained to me, "I want you to put your nose in the corner and think about what you need to tell her when she gets here.

"And if I don't like what I hear, you better believe you'll be going right back over my lap for and I'll re-warm that bottom of yours."

With the thick diapers hindering my movement, I waddled over to the corner and dutifully put my nose into it. It was only moments later, that I heard my mom's car pull into the driveway.

It was going to be an awfully long drive home.

　

THE END