A short story by 'The Scallywags.' Please feel free to use, and abuse, this story in any way you care. Though should you want to reproduce it, do please give us suitable credit. Thank you.
I have no idea how it started. I suppose, with hindsight, I should have been more careful, but I frequently used the alley behind Thrifty as a shortcut, fully knowing I lived in a decidedly rougher part of town. Still, I did nothing to provoke the events that were to so drastically change my life.
It was late Friday night as I entered the darkened alley. I immediately saw the two hookers, but failed to notice their pimp loitering in the shadows of the car park bright lights, had I seen him, I may well have considered taking the longer, better lit, route to my apartment. As I passed the hookers, surreptitiously giving them the once over from the corner of my eye, the prettier of the two, a black girl about the same height and build as my slight frame, called "Well lookey here! What a pretty lil' thang we got traipsing down the alley at this ungodly hour. A pretty thing like you could give working girls like us a run for our money!"
Unsure about what she was talking about I pressed on towards them and ignored her, looking the other way.
"Oh, you too good for trash like us? I don't think so. I could whoop your sissy ass any day, any time!"
Surely she wasn't talking to me? I continued to walk on and ignore her: a big mistake. She interpreted my silence as some type of provocation and stepped out to block my path.
"Look at you white boy, you ain't no man. You look like a proper little sissy with your pretty face and long hair, you ain't no big deal."
As I tried to maneuver around her, she shot out her hand and pushed me against the alley wall with surprising force. I staggered back against the cold brick, as much in shock as as a result of the unexpected blow.
"Yeah, you see that white boy, I'm gonna whoop your ass, then I'm gonna make you my little sissy bitch. You beat me, you get to walk free, but if I whoop your sissy ass, then you get to become Sharlene's personal little sissy slave. Tyrone here will be the referee."
This was the first time I noticed the enormous Negro lounging in the shadows. As he stepped out I began to realize the trouble I was in.
Sharlene took advantage of the distraction and swung her right fist at my head. I was totally unprepared, and still leaned against the alley wall, all I could do was try and through up an arm to deflect some of the force of the blow. It still caught me squarely on the ear and served to make me see a few stars.
Tyrone was now behind me, the other hooker in front, both serving to block off any escape path. Tyrone silently smiled his encouragement to Sharlene, the other hooker was far more vociferous, shouting for Sharlene to "Kick the ever lovin' white shit outta him". Sensing I was dazed and unprepared to fight, she moved in. Another roundhouse punch was aimed at my head; I instinctively bought my arms up to guard my face, realizing too late that she had tricked me. With my arms up at head level, my lower body was unprotected. With impressive speed, Sharlene swung her thigh booted foot straight up between my legs and into forceful contact with my groin.
I dropped to my knees like I'd been shot, pain flashed through my every nerve as I clutched my bruised testicles.
Sharlene moved in for the kill.
I was now powerless to stop her as she moved in close, grabbed a painful handful of my hair and proceeded to violently slap my face.
"You had enough whitey? You ready to become my little sissy faggot slave?" Her blows continued to rain down on both my cheeks, the stars were returning to circle soundlessly around my head. I could take no more of her abuse. I had to stop her, and yet was unable to move to block her assault, let alone fight back. If I didn't want to receive some long-term damage, I had no choice but play along in the hope of buying some time.
Unable to raise more than a whisper I managed to croak "Alright. You win..."
Sharlene was delighted. She immediately released her grip on my hair, resulting in my sliding to the dirty ground in a pathetic heap, as she danced around screaming her victory and proclaiming me to be her sissy faggot slave.
As I lay still moaning upon the alley floor, Sharlene, Tyrone and the other hooker, who I later learnt was named Vixen, held a quick conference to which I was not privy. At least the time they spent talking allowed me to recuperate a little until I had recovered enough to try and silently crawl away down the alley. Alas, I was soon spotted and dragged back by Tyrone who then proceeded to empty my pockets, confiscating my wallet, the cash contents of which he passed to Vixen, who disappeared towards the front of the store, before he pocketed the remaining contents including my drivers license and credit cards.
Sharlene moved to stand menacingly over me. "Well then sissy, you ready to begin your new life as my pretty little sissy slave?"
I could only look at the ground in combined shame and fear.
"Listen you little faggot, I whooped your ass fair and square, you belong to me now. And from now on when I talk to you, you answer me as Mistress Sharlene and always refer to yourself as sissy, you understand me bitch?"
The force of her shouting served to further cower me, I meekly answered here" Yes Mistress Sharlene, sissy understands."
"Good, then you can start your new life by thanking me for introducing you to your new role by giving me a good eating out." With that, she pushed me onto my back, quickly hiked up her short skirt and then dropped her red panty clad pussy directly onto my unprotected face.
I was totally blacked out; a powerful, rather unpleasant aroma assailed my nose as she squirmed down upon my sore face. Her voice barely audible as her stockinged thighs clamped my face in place. "Now I had a fairly quiet night tonight, so things shouldn't be to... to messy down there. Use your little sissy tongue to bring me to big ol' orgasm."
Left with no alternative, and no wish to explore the consequences of disobedience, I proceeded to push my tongue as far up her smelly slit as her tightly stretched panties would permit.
Tyrone took the opportunity to strip me of my shoes, socks and jeans so that I lay naked below the waist upon the dirty floor of the darkened alley with a hooker grinding her foul pussy into my defenseless face. Sharlene transmitted her disapproval of my efforts by reaching behind her and twisting viciously upon my nipples.
"Come on sissy, you gotta do better than that" she called as she pulled and twisted my nipples through my thin cotton T- shirt. I redoubled my efforts to reach her clitoris through the damp nylon of her panties until she was satisfied and began to rock back and forth upon my very sore face.
"Oh yes baby," she cooed, switching from abusing my nipples to gently squeezing and caressing them "that's it, give Mistress Sharlene a real good tonguing. We're gonna have us a whole load of fun, just wait until Doctor J gets you on the hormones, won't be long until you get yourself some real titties and a big ol' girly ass. We gonna make you such a pretty lil' thang, you gonna be able to help me warm up my John's, there's a real market out there for a good sissy cock sucker, just you wait and see."
Despite my revulsion at her words, I continued to stick my tongue up her cunny as far as I could, desperately tying to ignore the juices that flowed down upon my face. I hated to think how many other men's semen was mixed in with her own sticky fluids.
Tyron had by now cut my T-shirt from my body and removed my watch so that I now lay totally naked upon the grimy floor. I could hear muffled voices so assumed Vixen had returned.
I was unprepared for the next event, and totally unable to prevent it as I felt the unmistakable sensations of my toenails being painted. My initial reaction to move my feet was stopped by Sharlene recommencing her abuse of my raw nipples.
"You just lie still like a good sissy or we'll make things a whole lot worse for you." I had absolutely no reason to doubt her threat and so stayed perfectly still as unseen hands painted my toes.
As Sharlene approached her second orgasm, my tongue now red raw, Tyrone or Vixen switched their attentions to my hands. I felt unfamiliar sensations as they glued enormous inch and half talons onto each of my fingernails before painting them also.
My next 'delight' was to be covered in some type of cool cream from neck to toe. I had no idea what they were up to until the cream started to burn my skin, then I realized they had smothered me with a depilatory cream. For twenty minutes I lay there, every inch of my skin aflame as I submissively continued eating out Sharlene's repulsive pussy.
At last somebody used a bottle of water to wash the foul cream from my body and so ease the stinging. I could hear their laughter as they looked upon my denuded body.
Finally, after her forth orgasm Sharlene was satiated and climbed off my face which was by now drenched in the combination of hers and unknown men's love juices. Before I had a chance to recover, much lass survey their dreadful handy work, Sharlene dropped onto my chest, pinning my arms beneath her, and after carefully donning a pair of protective gloves, proceeded to work some foul smelling lotion into my hair and scalp. Satisfied that every last hair on my head was covered with the evil goo, she picked up a pair of tweezers and indelicately proceeded to pluck my eyelashes, an unexpectedly painful process that she obviously relished. Satisfied with the high line my eyebrows now had, she then proceeded to work a foundation cream into my facial pores until my face was totally covered beneath the tick cream.
Upon a signal from a grinning Tyrone, who used my watch now resident upon his wrist to time affairs, Sharlene ordered me to shut my eyes tightly before she drenched my hair in more bottled water, washing out what ever she had so thoroughly worked into my scalp earlier. The results delighted her as a huge grin lit up her pretty face.
After much pulling and pushing of my hair, rapidly drying in the warm night's breeze, she returned her attention to my face. For the next forty minutes I was subjected to a very painful ear piercing, with several loud and dangling earrings being forced through the three still bloody holes that adorned each ear, then a barrage of cheap and garish cosmetics.
First my eyes were outlined with a dark pencil, and then enormous false eyelashes were glued onto both upper and lower lashes before being repeatedly covered with coat after coat of thick and heavy mascara. An incredible number of brightly colored cremes were applied to each of my eyelids, before my cheeks were blushed.
After meticulously lining my lips with a red pencil, Sharlene filled in the area between with a vivid pink lipstick. A thick coat of glutinous gloss completed my "lovely cocksucking lips' as Sharlene so indelicately put it. My final ordeal was to be absolutely drenched in a cloying cloud of cheap perfume before I was permitted to stand.
Sharlene returned to fussing over my hair as I caught my first glimpse of my horrendous new fingernails. They were hideous, projecting a full inch beyond the end of my fingers, how I would ever perform even simple operations such as picking anything up, let alone wiping my ass, was totally beyond me. I tested their fitting by pressing one against the palm of my hand, not surprisingly they hadn't been parsimonious with the superglue, the nail appeared permanently bonded to my fingernail.
Vixen produced a pathetic excuse for a dress, the almost transparent pink garment looking way to small for a child to wear, let alone me.
Still I dutifully pulled it over my head and attempted to pull it down to at least mid-thigh. Sharlene then used Tyrone as a prop as she skillfully stepped out of her soiled panties before handing them to me and ordering me "Here you go sissy, your first pair of panties. I think in future it will be your privilege to always were my dirty panties and other clothes, that way we will cut down on the amount of washing and ironing you will have to perform at my apartment. You can wear Vixens old shoes, one heel's loose, but they should hold. Now why don't we see if there's any late night john's out there for us to service while Ty goes and checks out your old apartment for anything valuable? You won't be returning to your old place, you can come and live with me, after all what's the point of having a slave unless they're there to serve you night and day"
I quietly forced the ill fitting sandals on to my feet, trying not to cry as I caught sight of my garishly red painted toenails.
The shoes were tight, and as I put my weight upon their four-inch heels I felt the heel of the left one wobble.
Not caring for my unfamiliarity with the teetering heels, Sharlene grabbed my wrist and began dragging me towards the front of the store. I had never felt so vulnerable in my life as I teetered along behind my new Mistress atop the high heels, unknowingly adopting a sexy little wriggle walk, my pantied butt swaying from side to side with each step.
The biggest shock came when we reached the front of the still fairly busy Thrifty store and I caught sight of my reflection.
A mass of brilliant platinum blond tresses adorned my head, my every move sending them cascading, brightly reflecting the light in every direction. The three painful earrings danced and jangled noisily, but my face was the biggest shock.
While there was no mistaking the masculine shape of my body, my face was drop dead gorgeous. Way too much makeup served to frame startlingly blue eyes, with enormous lashes blinking slow and seductively below a rainbow of this creamy eyeshadow. My cheeks blushed as if I had overheard some ribald remark and my lips looked to invite a kiss, or worse to slide around some hard cock. My body was tightly sheathed in the little pink dress with the red panties clearly visible beneath.
The high heels served to make me push my ass out in a thoroughly wanton manner; in short I was a total sissy tart.
Sharlene was delighted with my shocked reaction and decided to celebrate by having me go into the store to purchase a long list of items including: A carton of menthol cigarettes (which she considered to be suitable for a little sissy cocksucker like me), Two dozen assorted condoms.
A pretty ribbon for my hair, A purse to carry my condoms and make up in, And a pack of tampons ('make sure you ask that they are the largest size') Worse, I was not allowed any cash but would have to use one of my credit cards, temporarily returned to me, along with my ID, and was ordered t speak in my normal voice, i.e., do not try and pretend to be a woman!
I was pretty well known in this store, having lived just around the corner for the past three years and did not like the idea of having to sashay my way in there dressed as I was. Tyrone grabbed my wrist and growled, "There's just one thing missing for a little slut like you."
With that he dragged me back into the alley. I was totally unprepared for what happened next. When we were well out of sight of the storefront, Tyrone forced me to my knees and then proceed to unzip his fly right before my eyes! Before I could struggle back onto my high-heeled feet, he grabbed a large handful of my platinum curls, twisting painfully to ensure he had a good purchase and dragged my head to within mere inches of the largest cock I had ever seen.
"Now you suck my dick real tender like sissy and maybe, just maybe, I'll let you live. But if I don't like the way you're sucking it, or I feel them pretty teeth of yours, then you are going to feel a whole world of pain. You hear me bitch?"
I could only nod my head, my earrings tinkling loudly, in abject terror of this enormous man.
"Good, now give my head a nice kiss and then get to giving me the best BJ I ever had."
Fighting back both the fear and abject revulsion, I did as I was bade. I slowly lowered my face and placed a big pink kiss upon the top of his large purple glans. Then swallowing hard, I opened my lipsticked mouth real wide and slowly lowered my head until he filled my mouth completely. His warm penis tasted slightly salty as I began bobbing my head up and down upon his enormous spear.
A bright flash from my right indicated that Sharlene was back, having used more of my money to purchase a disposable camera with which she now carefully captured every degrading nuance of my first blowjob.
Retaining his tight grip upon my hair. Tyrone slowly forced more and more of his meat into my mouth until my throat was stretched to seeming breaking point around his mammoth tool. Sharlene moved in close to make sure she captured the spectacle of my throat stretched sound Tyrone's giant cock as I fought back the gag reflex. Finally he forced his entire nine inches down my throat, my lips were pressed into his curly black pubic hair as flash followed flash and Sharlene and Vixen laughed at the spectacle I was being forced to provide them. In and out he rammed, I quickly learned to time my breathing with his thrusting and so avoided asphyxiating, all the time being very careful to not let my teeth in any way scratch his magnificent black cock.
Finally, after close to ten minutes of serious face fucking, Tyrone reached orgasm. He slid his dick all the way down as the first jet of cum splashed deep inside my throat, with each splash he withdrew a little until he was filling my mouth with spurt after spurt of hot white semen. My mouth was so tightly stretched around his massive girth that I had no choice but to try and swallow every last drop he shot. Not satisfied with the humiliation I was being forced to endure, Sharlene cried out, "Give him a face-full Ty."
Ty was only too happy to comply and so pulled his cock from between my bright pink lips and let the last few powerful spurts fly into my unprotected face. Huge globs of thick spunk rained down upon my face and hair as I valiantly tried to capture as much as possible with my still open mouth.
"See, I told you he was a natural cocksucker," cried Sharlene as she continued to capture each degrading step on film, "See how he's trying to drink every last drop!"
Tyrone used his glans to ensure not an inch of my face was left uncovered in his cum. My face was a ruin, makeup was smudged under thick white cum, my mouth was a mass of badly smeared lipstick.
"Good, now she's ready to go shopping!" laughter rained upon me as I lay in a cum covered heap upon the dirty floor.
The End
Copyright: The Scallywags@aol.com July 2000