A Sissy Gets More than he bargains For

A Sissy Gets More Than He Bargains For

　

I was watching tv in the living room when I heard the doorbell ring.

"That's probably Alyssa,'' my mom said as she got up to answer it.

Alyssa was a senior at my high school that was totally hot. Besides the fact that she was drop dead gorgeous, she also had a body to die for. She had been a friend of my mom's for several years and I had watched her grow from a cute sophomore, to a knockout in her senior year. She had developed early and it seemed to me that she was always having a problem keeping her big bust within the confines of her one size-too-small tops. I couldn't help staring at her whenever I passed her in the hall at school, savoring glaces at her bountiful profile.

Unfortunately, she couldn't care less about me, a geeky boy in the 10th grade that wasn't anywhere near her league.

Opening the door, my mom stood aside to let Alyssa in.

As usual, she looked amazing, wearing snug jeans and high heels but what caught my eye was the striped t-shirt that looked like it had been spray painted over her fabulous boobs. My eyes just about popped out as I drank in the sight. Man, they were big! I figured 38DD at the very least, possibly bigger. Boy, what I would give to look at one of her bras, I thought. And she carried herself with such confidence, that she always stood tall, thrusting her bosom out proudly which only made them more prominent and harder to ignore.

"Hello Alyssa!'' my mom exclaimed.

"Hello Jean,'' she replied, revealing her beautiful smile as she did.

Alyssa was the only young person that my mom let call her by her first name and I think it was because even she was proud to have this babe as her friend.

I sat up from the floor, my heart stopping as I feasted my eyes on her fantastic curves.

"Hi Alyssa!'' I said with a racing pulse.

"Hey,'' she with the absolute minimum amount of courtesy required. I doubted she even knew my name.

"Ready to go?'' she asked my mom.

"Sure, let me just grab my keys,'' she answered as she took a set off one of the hooks along the wall.

"Tommy, we're going to the movies, I'll be home late tonight,'' she told me, ''don't forget your homework.''

"Uh-huh,'' I said, still staring at Allysa who was totally oblivious of me.

As they headed out the door, my mom said goodbye to me.

"Bye Alyssa!'' I called out, but she ignored me and strode out, her high heels clicking on the tile floor.

As soon as the door closed, I walked over to the window to sneek one last look at the object of my fantasies. As she bent over to get into my mom's car, I noticed the line of cleavage from the plunging scoop neck of her top as her heavy breasts shifted.

As they drove off, I sighed from sexual frustration. Going down the hall, I went into my bedroom and opened up the closet. Next to my shirts and pants hanging up, were numerous cardboard boxes. I selected the one on the bottom and pulled it out. Opening it up, I pulled out my secret stash of dirty magazines. I flipped through the pages of one that had a picture of a model that reminded me of Allysa and I slowly stroked myself as I fantasized about her.

After making myself even more aroused, I put the magazine aside and got out my most secret of items, a thick cloth diaper and baby pants. In an excited frenzy, I tore off my clothes and sat down on the white rectangle of bunny soft cotton, shaking baby powder over my little erect penis before pulling up the ends. I closed my eyes as I felt the soft, warm cloth envelope me, caressing my loins tenderly. Taking a pair of diaper pins, I poked them through the corners and snicked them closed. Remembering that Alyssa had been here in our house only minutes ago, I imagined her bending over, putting me into my diapers and I blushed at the thought of it.

With careful consideration, I chose a pair of soft pink plastic pants to go over the diaper and I shoved my feet through the leg openings, yanking it up my skinny thighs to cover the fat, bulging diaper.

My stiff pee-wee strained against its babyish prison and I stroked it deliriously over the plastic panties.

Looking into the box, I took out a short baby dress and pulled it over my head. I loved it because of the shiny pink material and the hem that went just past the waistband of my plastic pants, leaving my diapers fully exposed.

Hastily, I put on the other elements of my ensemble. White knee socks, black mary jane type shoes, and a couple of pink lacey bows to put my medium length hair into pigtails. Looking down at my babyish appearance, I rubbed the front of my diaper madly, my head swimming from arousal. Holding myself back from the brink of a shuddering orgasm, I stood up and headed for my mom's room. Once there, I stood before her full length mirror and revelled in my reflection. I looked convincingly like a baby girl and I pranced around, enjoying the look of my shiny round bottom, encased in my thick diapers and plastic panties.

My mom had a feminine room, and it made me want to be more feminine. On impulse, I sat down at her vanity and picked out some pink blusher. Taking the little brush in its case, I applied some to my cheeks, giving myself a girlish appearance. Next, I took some pink lipstick and applied several coats to my full lips. When I finished, I smacked them the way I had seen girls do it in my school.

Looking back in the mirror, I couldn't believe the transformation. I was staring at what had to be the biggest sissy in the world. The thought compelled me to stroke the front of my diapers feverishly, drunk with sexual excitement.

I stood up and walked out, going into the living room, confident in the knowledge that my mom wouldn't be back for hours.

I loved the feel of the plastic panties against my skin as the bulk of my diapers caused them to slide sensuously between my thighs. I skipped over to the back door and opened it wide, knowing that no one would be able to see me because of the high wooden fence that surrounded our yard. Filled with excitement and sexual energy, I skipped outside and giggled at the risk I was taking. It felt wonderfully free, that I could be outside, dressed as a sissy baby in diapers and a dress and be able to get away with it.

After several minutes of unfettered abandon, I went back inside, going by the front door and I noticed the keys for my mom's BMW were still sitting on its hook. That's odd, I thought. Why would she have taken the older Toyota tonight?

For a second, I forgot what I was wearing and considered the possibilities. I had always had a passion for my mom's BMW but she'd never let me drive it--she always said I was too immature for it which I resented bitterly. I was strongly tempted to grab the keys and take the little hotrod out for a spin. After all, she wouldn't be back for hours and I'd be back long before then.

Feeling naughty in my sissyish outfit, a plan began to form. What if I went out and drove the car as I was dressed? Since it was night out, it didn't seem likely that anyone would be able to get that good a look at me, but the idea of being in public dressed lke a baby thrilled me to the core.

Impulsively, I snatched the keys and grabbed my wallet which had my driver's license that was only a month old.

The distance from the front door to the side door of the garage was only three feet but I looked around carefully before dashing outside and into where the Beemer was kept.

I still couldn't undestand why she hadn't taken this car, I thought, as I gazed in admiration at the immaculate silver paint. Oh well, no matter. Now, it would be my opportunity for some real excitement.

As I sat down behind the wheel, I had to get used to the feel of my bulky diapers which took up so much room. As I pulled out of the garage I reflected how odd it felt, driving in diapers and a dress. With my left hand on the wheel, my right went down to stroke the front of my diaper.

As I drove out of my neighborhood, my heart was going a thousand miles an hour. It was so exhilarating to be outside dressed like a sissy baby! This was a rush like I'd never experienced before.

For the next half hour, I drove around town, savoring the experience. A couple times, a car would drive by and honk at me and at one stoplight, a car full of girls made several humiliating comments to me. I just smiled and waved back like a well behaved sissy should. It was when I got on the freeway that disaster struck.

I was driving along for about fifteen minutes when suddenly my rear view mirror was filled with the flashing lights of a police car. My jaw dropped and I gasped in terror. How was I going to explain myself out of this one?

Shaking with fear, I slowed the car down and brought it over to the side of the highway. If it hadn't been for the thick bulk of my diapers between my legs, my knees would've been knocking from fright. With the cop's lights flashing angrily behind me, my mouth went dry and I quaked nervously. Without realizing it, a trickle of pee escaped into my diaper.

As I waited for the patrolman to come up to the side of the car, I bit my lip nervously trying to think of what I was going to say. With a super bright spotlight, the policeman illuminated my car which made me feel as if I were on stage. I cringed as he got out of his car and walked toward mine, his hand on his gun. In my panic, I let go with another stream of pee into my already damp diaper.

I rolled down the window as he came alongside and shined his flashlight in my face.

"What the hell is this?'' he said waving his hand at my sissy dress and diapers.

"Uhmm...'' I stammered uncertainly.

He looked at me with disgust and I wanted to melt into the seat and disappear.

"You know your tags are expired?'' he said gruffly.

No wonder my mom had taken the other car! Now I understood all too well!

"They are?'' I asked dumbly.

"Yeah they are. Let's see your driver's license and insurance,'' he told me bluntly.

With shaking hands, I fished around for my license but I couldn't find the proof of insurance. I was so embarrassed to be sitting here in my diapers and pink dress getting grilled by this tough cop. I think my face was redder than the blush I was wearing.

"I can't let you drive this vehicle without current tags and insurance,'' he told me curtly.

My lipstick coated lips parted as my jaw dropped open in surprise and anxiety.

"Y-you c-can't?'' I stuttered nervously.

"Nope. I'll have to get a tow truck and you'll have to come down to the station,'' he said flatly.

"Oh no! Please! Isn't there something else I can do?'' I pleaded desperately.

The big cop looked me over strangely and after a brief hesitation, told me to get out of the car. More fearful than ever, I stepped out into the glaring spotlight, painfully conscious that my bare legs and diapers were on display for every car passing by. I tried in vain to tug the hem of my dress down but it was entirely futile. Everyone could clearly see I was a young man wearing thick diapers and a baby's dress. Much of the traffic going by slowed down to get a look at me and they honked their horns and yelled things as they drove by.

The policeman went back to his patrol car and for some reason, turned off the spotlight before returning to the BMW. Instructing me to go to the other side of the car where we were relatively sheltered from view, he pushed me down on my knees and unzipped his pants, revealing a massive hard-on straining within his underwear.

''I might be persuaded to forget this whole situation, Girly-boy,'' he intimated as he thrust his pelvis toward my face.

Instinctively, I understood exactly what he wanted but I still hesitated. I wasn't gay and I had no desire to suck this guy's cock.

Whimpering pathetically, I stalled as I pulled the waistband of his shorts down, exposing the biggest cock I had ever laid eyes on. I looked from the massive head now staring me in the face, up to see him grinning wickedly down at me. With a sob of shame, I licked my lipstick covered lips and opened them wide to take the gargantuan cock into my mouth. It tasted warm and somewhat salty but it filled my mouth completely, stretching my cheeks wide to accomodate him. The cop must have sensed my hesitation because he pushed my head down further, forcing his cock deeper into the back of my throat and choking me. I waved my hands in protest but he held my head firmly as he established a rhythm of his own choosing.

Sliding his hard dick in and out of my mouth, I slobbered helplessly, leaving a pink ring around the base of his cock from my lipstick while he guided my head up and down. Unconciously, my tongue caressed the underside of his shaft and he moaned with pleasure. I felt like I was deep throating a cuccumber, his cock was so large. Everytime it hit the back of my throat, I nearly gagged.

After five minutes of him humping my mouth, my jaw was getting very sore and tired. I assumed that when he was ready to cum, he'd pull it out but I guess I was pretty naivé. I felt his cock tense up in my mouth and he thrust it hard down my throat. Taking a firm hold of my pigtails, he suddenly let out a bellow like a bull and he exploded in orgasm. My eyes shot wide open and I squealed in anguish as he pumped his warm, creamy load into my mouth. I was repelled by the flavor but I was forced to swallow it because after withdrawing his cock somewhat, he thrust it back in, rewarding me with a second load of his sperm. I gagged as my mouth was filled to overflowing.

I squealed again and struggled to free myself, flailing my arms around but the big cop easily held me in place. It seemed that no sooner had I swallowed his cum, then more would shoot into my mouth. With his massive cock filling my mouth, I was forced to swallow again and again, of his nasty cum.

At last, he slid his cock out of my mouth where it glistened with my saliva. I gasped for breath as he held his giant member in front of my face.

"Lick it clean, Sissy-boy,'' he ordered me huskily.

Meekly, I did as I was told, lowering my mouth back over his cock, slurping amd sucking as I cleaned it with my tongue. When he was satisfied and it had finally started to soften, he looked me over as if he had a new idea.

"Turn around,'' he said curtly.

What could he want now? I asked myself frantically.

"Pull the back of your dress up,'' he ordered.

Was he going to do me in the ass now? How could he, after he just came? I wondered.

I assumed he just wanted to get a better look at my diapers but I quickly learned I was wrong again. I felt rough hands pulling the top of my diapers back, exposing my crack to the cool night air.

Suddenly, I felt a stream of hot pee against my bottom as the cop proceeded to use my diaper as a urinal. I gasped in shock and whimpered from the humiliation of it. The steady stream of pee quickly became a pool as my diaper struggled to soak up the volume and I felt his piss splattering against my backside and crack. I sobbed tears of frustration and humiliation as I was forced to hold up the lacey hem of my sissy dress and provide him with a receptacle.

The thick cloth between my legs that normally gave me a babyish waddle now was becoming saturated with warm wetness. I cringed but remained in place out of submissiveness. I had always been lacking in bravery and tonight was no exception.

After the first strong surge, which must've lasted for a minute, his flow paused but then he continued with yet more pee. I stomped my feet and pouted, whimpering plaintively with impatience. My diaper was growing heavy from the accumulated pee and it began to sag noticeably. Between my legs I could feel the growing warmth as the wetness seeped forward and surrounded my crotch. I felt so violated to have HIS pee soaking into my diaper that l sobbed with shame.

At last, his stream tapered off to a trickle. He released his hold on the waistband of my plastic panties and they snapped against my back. As a last humiliating gesture, he slapped the thick seat of my diapers which gave off a dull thud. By now, they were soaking wet and I cringed as his pee embraced me all around.

With tears of shame in my eyes, I waddled back to the driver's seat, trying to keep the wet cloth from touching my skin. My efforts were pointless, however, since as soon as I sat down in the car, the sopping wet diaper was mashed against my skin. In fact, it was so wet, I feared that l'd leak onto the fabric of the driver's seat. Oh well, l'd worry about that when I got home.

The cop drove off from behind me and I pulled out from the shoulder of the highway to get back into traffic. I couldn't wait to get home and take my wet diapers off but l certainly didn't need another run-in with the Law. I made sure l didn't break any speed limits and l made full stops at every stop sign.

The whole way home, I couldn't get the taste of the cop's cum out of my mouth and l blushed everytime I re-lived the experience in my mind. I had never been so humiliated in all my life!

Ten minutes later, I was waddling out of the car and into the front door when I got the second shock of my life. Standing there in the entranceway were my mom and Allysa!

My jaw dropped open and my face turned a bright shade of red. At the same time, in my state of panic, I involuntarily let loose with another stream of pee into my already saturated diaper.

"What in hell is going on here!?'' my mom demanded angrily.

Behind her, Allysa was giggling and shaking her head as she took in my sissy dress, diapers and Mary-Janes.

"I-ah-I...,'' I couldn't think of a single thing to say to explain my appearance.

"What are you doing wearing a dress and diapers like a little baby!?'' she stormed.

I shifted my feet and looked down at the floor hoping it'd swallow me up but alas, it didn't.

"Umm-I-umm...,'' I mumbled.

"And what are you doing driving the BMW?!'' she continued.

"Well, uh, I...''

My mom didn't wait for me to answer. Instead, she snatched the keys out of my hand and then grabbed my wrist roughly, yanking me along behind her like I was still four years old.

"Young man, you are in SO much trouble!'' she snapped at me as she led me into the living room. She paused only long enough to retrieve the wooden paddle hanging on the wall before seating herself on an armless chair in the center of the room.

My mouth went dry and I peed a bit more into my diapers. By now, l had to hold them up by the waistband with my only free hand due to the weight of the pee saturated cloth.

When my mom sat down, she looked closely at my diaper for the first time and discovered just how wet I was.

Glaring alternately from my diapers to my face, she shook her head in anger.

"lt's not bad enough you have to dress like a baby girl--you had to wet your diapers too?''

I bit my lip in silence and shame as I turned from her to the heavenly Allysa who just shook her head in disgust.

My mom said the next sentence very slowly and deliberately.

"Tommy, I am going to blister your bottom and then you've got a lot of explaining to do,'' she said angrily.

I whimpered in fear as she began peeling my clinging plastic panties off--I had been spanked numerous times with this paddle and everytime, I had cried like a baby. Now, tears of shame trickled down my face as I watched Allysa cross her arms across her bountiful chest and make herself comfortable. I could only imagine what she must be thinking of me now and my face burned with humiliation.

My mom jerked me over her lap and I looked up to see Allysa smiling down at me, a look of smug satisfaction on her face. I felt a chill breeze on my rump as my mom peeled the pee soaked cloth back, exposing my damp cheeks to the air. First one pin, then the other, as she unpinned my diaper and pushed it down between my legs.

"Allysa, you're about to see how sissy boys get punished in this house,'' my mom informed her as she held the paddle poised over my defenseless bottom, ''and this one's just a big crybaby.''

"I always figured as much,'' she replied as she sat down and casually crossed her legs, dangling her high heels a few feet in front of my face.

The paddle swooped down and landed in the center of my cheeks with ferocity, producing a loud crisp 'SMACKKKK!!' that filled the air. I cried out and kicked wildly, immediately bursting into tears. Again and again, my mom swatted my fanny, quickly turning my pale white bottom, a bright shade of cherry red. Tears coursed down my face as I bawled pitifully. I kicked my feet helplessly but they were tangled in my damp plastic panties. The dampness of my bottom only intensified the impact of the paddle as each searing swat made me gasp for breath.

My mom made quite sure that every square inch of my bottom was turned a deep shade of red before returning her attention to the tender center. Then she'd change tactics and swat first one cheek, then the other. I sobbed and beat my fists on the floor, helpless before her avenging assault.

"This-is-for-being-such-a-sissy!" she said, punctuating each word with a stinging slap of the paddle.

At last, she finally stopped spanking me but I was completely defeated. I lay over her lap crying like a baby as she pulled my wet diaper back up and pinned it tightly in place. It was repelling to have the now cool and clammy cloth snug against my skin but it did help to somewhat alleviate the stinging fire that was blazing on my fanny.

I struggled weakly to get up as l rubbed the wet tears off my flushed face. I couldn't bear to look at Allysa but I could feel her eyes burning into me.

Adding to my humiliation, my mom snaked my dripping plastic panties up my legs and then up and over my pee stained diapers.

"So, you like dressing like baby do you?'' my mom asked, still angry with me.

"No!'' I cried between sobs as I shook my head.

My mom grasped my chin firmly in her hand and raised it to look directly into her eyes.

"I suppose someone came in here and forced you into a little girl's dress and diapers, hm?" she said dubiously.

I shook my head sorrowfully but I couldn't return my mom's stern gaze.

"Well then. Why don't we just see what else you've got stashed away in your room?'' she replied curtly.

Oh no! ln my haste and excitement earlier, I had neglected to hide my baby stuff, so confident was I that I would be back before my mom returned.

Standing up, my mom pulled me along behind her like a child as she marched me down the hall to my room. The elastic leg holes of my plastic panties rubbed against the backs of my thighs painfully where the paddle had left its stinging impression.

When we reached my bedroom, I discovered, much to my dismay, my other diaper supplies were still laying out in plain view, a couple pairs of plastic panties, baby powder, and my other diaper, not to mention the box that was lying open on the floor.

"Well, well, well,'' my mom said appraisingly, ''looks we have another change of diapers for mommy's little baby.''

I blushed anew and kept my eyes downcast.

"What else have you been hiding in here?'' she asked as she began rifling through the box. She quickly disovered a pair of frilly rhumba panties and my other dress but she hit the roof when she found my stash of dirty magazines.

''Jimmy! What kind of perversions have you been up to in here!?" she demanded in a rage.

"No-nothing. H-honest,'' I stammered, still sniffling from my painful spanking.

"That does it!'' she snapped as she held up my Score magazine, ''you've just earned yourself another trip over my knee!''

My knees grew weak as she took a seat on the side of my bed and reached over for the paddle. This time, she didn't even bother to pull my panties down--instead, she yanked my diapers down to my knees with the panties still covering them. This exposed my bare crotch to Allysa's gaze who promptly broke out in a fit of giggles when she saw how truly tiny my penis was. My face reddened and I immediately covered my privates with my hands. Wasting no time, my mom easily pulled me over her lap and with my hands in front of my crotch, l toppled over, my bright red bottom facing up and ready to be spanked again.

"Here's your porno magazine Tommy,'' my mom said as she tossed my issue of Score down on the floor in front of my face, ''enjoy yourself all you want.''

No sooner had my eyes focused on the busty blonde on the cover of the magazine when the paddle slapped my bottom with a fiery impact. I burst into fresh tears and bucked wildly, trying to escape my mom's implacable arm but she gripped me firmly by the back of my dress and smacked away.

My bottom, already suffering from the previous spanking, felt as if red hot coals were being held against it. The paddle felt like a heated skillet everytime it made its searing impression on my fanny. Looking up at Allysa, I couldn't see her clearly through my tears but I could tell she was nodding her head in agreement. Obviously, she felt this was an appropriate punishment for a young man who liked to wear diapers and dress like a little girl.

As my mom continued to slap my blazing bottom with the paddle, I cried like like the baby I was dressed up as. I kicked my Mary Jane-clad feet and pounded my hands on the floor but my mom never missed a beat.

After what seemed an eternity, she stopped and dumped me on the floor. I howled in pain and made sure my bottom didn't touch anything.

"Take that wet diaper off,'' she ordered me.

Sobbing out of control, I hastened to comply. By now, my bottom was so much on fire that I no longer cared whether Allysa saw my tiny pee-wee or not. It was not much bigger than my pinky finger and it kind of jiggled pathetically as I struggled out of my wet diapers. Out of the corner of my eye, I could tell Allysa was staring at it and I'm sure she was amazed and disgusted at the same time. I knew she'd never again think of me as anything but a big, diaper wetting sissy.

Gathering my remaining diaper from the bed, my mom laid it out and told me to lie down on it. Gingerly, I did as I was told but when my punished bottom touched the cloth, I sobbed loudly. My mom ignored my outburst and began sprinkling my pee-pee with baby powder.

"Since you like to wear diapers so much, looks like we'll have to go out and buy you some more, Tommy,'' she said as she pulled the thick cloth between my legs, ''of course, the money will be coming out of your allowance.''

With a set of pink bunny pins, she pulled the ends of the diaper together tightly and snicked them closed.

"Allysa, would you mind picking out a pair of panties for our pamper princess here?'' she asked nicely.

"Anything to be of help,'' she replied. Digging in the box she pulled out my frilly rhumba panties that were lined inside with a vinyl layer.

"These should keep your bed dry,'' she offered as she gathered the leg openings in her hands and looked me in the eye. Passing them over my feet, she began working them up my skinny legs. I was treated to a fabulous view of her unbelievable cleavage and her big breasts swayed slightly as she snaked the soft panties up to my diaper.

"Lift up Baby,'' she said as she worked them up and over the thick cloth wrapped around me. l blushed in shame as she looked me deeply in the eyes and my true self was revealed to her.

"There you go Baby," she said brightly, "now you're all diapered again and ready for beddie-bye."

Reaching down, she picked up a pacifier from inside the box and popped it into my mouth.

"Don't you look cute!" she said condescendingly.

Nursing meekly on it, I knew my life would never be the same.