Slave Sara

Chapter One

 

            I guess there are a few things I should say before I get started.  First, I am a (mostly) heterosexual male in my early twenties who has never really been a part of the hardcore S&M scene, and so what will be written here isn’t as exciting as the some of the transvestite stories I’ve read online.  Second, the reason my adventures aren’t quite as fantastic is because they are true.  Not based on truth or inspired by truth, but absolutely true.

            I’ve been aroused by the idea of wearing panties for over a decade.  I used to steal thongs out of the laundry at my apartment complex when I was a kid.  In high school, I snuck into the gym late one night and accidentally found the cheerleaders’ outfit storage and tried on one of their pleated skirts.  I was hooked (little did I know that eventually I would I would be the one doing the hooking!).  Later that week I drove to the south end of the city to buy porn – I was seventeen and it took all my nerve to go into the store, wondering what I would do if they carded me – and on my way back up home I stopped by Wal-Mart and bought clothespins, some dog-collar choke-chains, and a heavy combination lock.  I parked in the deserted lot of a grocery store between two major city streets, leafing through the dirty magazines I’d bought, drooling over the box of the Jenna Jameson VHS – my very first porno – and stroking my rock-hard cock.  I didn’t know the word exhibitionism, but looking back I knew I was a hopeless, desperate exhibitionist even then.  In my car that night, I slipped out of all my clothes, pulled on the thick green and black cheerleader skirt – so tight! especially over my erection – and pulled out the choke chains.  A thin rope of pre-cum stained the inside of the skirt as I placed the ends of one choke chain in the mouth of two clothespins, then pinched those clothespins over my throbbing, erect nipples.  The chain bounced against my chest, tugging on my nipples with a delicious burn.  The other choke chain I looped around the base of my balls, and then I locked the combination lock through the dangling ends of the chain – my very own homemade ball-stretcher.  Pumping my cock, breathless, I opened the driver’s door of my car and stepped barefoot onto the cool asphalt, naked save the nipple clamps, tight cheer skirt, and CBT lock dangling painfully below the pleated hem.  The weight on my sack was the most wonderful sensation, a cruel tug that sent shivers of pleasure up my spine.  Under the sodium lights of the parking lot, open for anyone passing by to see, in view of a major highway even – there I was, a teenage sissy-bitch reaching under my skirt to jerk off in public, the jingle of my ball-and-nipple-chains echoing clearly off of the darkened storefronts all around.

            It wasn’t long before I became brave enough to buy panties from Wal-Mart late at night.  I remember my first pair – a tight size 5 thong, white with black diamonds, cheap nylon.  I wore it with the chains, clamps, and cheer skirt one night to school, jumping over the baseball fence after midnight to run the bases in my trampy little slut outfit.  My imaginary Mistress, that sadistic voice in my head that always reminds me that the things that mortify me most the morning after are the ones that made me come the hardest the night before, commanded me to crawl to the pitcher’s mound, stand up, and unbutton the skirt.  Then I slowly pulled it down, shimmying my hips seductively as I revealed the cheap thong – a cheap thong for a cheap slut.  I then dropped to my hands and knees again, the chains jingling around my aching balls and my sore nipples as I crawled to home base.  There I spread, legs wide and on my knees, and I begged out loud for my Mistress to grant me release.

            Ball chains jingling, with the tight sensation of nylon flossing my cheeks, I sprayed come all over home plate.

            I always liked to fantasize that the stud from the soccer team, out for a late run, catches me in the act.  I try to bolt, terrified, and he grabs me and says, it’s okay, I won’t tell anyone.  Of course in such dreams, the condition for his secrecy is total humiliation.  He tells me that I had better clean up the evidence of my crime, and he holds my head down as I lick up my own fresh load of come.  Then he walks out to the pitcher’s mound and orders me to crawl back to him, to pull down his shorts with my teeth and suck his cock.  Before he comes he orders me to put the skirt back on, and jump in the back of his pickup.  He drives around to the front school parking lot – the one that faced the suburb’s main road, is always well lit, and has 24-hour cameras trained on it.  He stops the truck, leaves the headlights on, and pulls me around to the hood.  He tosses me a pair of strappy, high-heeled sandals, the kind club girls wear when they want dick, and says, “My last girlfriend left these on the floorboard, they suit you fine, slut.”  I struggle to pull them on, cheeks burning as the occasional pair of headlights passes at an agonizingly slow 35 mph, and then he grabs me and pushes me down, bent at the waist, over the hood of his idling truck.

            “Pull those panties off, now!” he commands, and where else would they go in such a fantasy but in my trembling mouth.  Balled up and sweaty, the thin nylon stuffed between my lips – he flips my skirt up and spanks me briskly twice. He commands me to beg him not to fuck me, to plead with him, to cry, to say I’m just an overeager sophomore whore who had too much to drink.

            “Please don’t fuck my ass, Master, I’m far too drunk to resist you,” I purr, wagging my ass scandalously.  He spanks me again and again; my legs and buttocks are slightly tensed, made shapely because of the steep angle of the trashy high-heels.  He snaps photos with his camera phone and then tosses the phone to me.  He tells me that when he starts fucking me he wants me to dial 911 and narrate to the operator how I’m being date-raped in the ass and loving it.

            “And you are going to love it, aren’t you bitch?” He demands, tugging on my hair to yank my head back.  I nod frantically and squeal an affirmative, feeling like a trussed pig on a platter, only the silver tray beneath my naked flesh is the painted hood of his truck, and the apple in my mouth is a damp ball of fabric, tasting faintly of my own salty pre-come.  Tears of joy are trickling down my cheeks.

            If I could thank him in a way more effective than letting him use me as his sissy anal fuckslut, I would.

            Then I feel him inside me.  I moan helplessly through the panty-gag as he pumps me from behind, and before too long, he pulls the thong out of my mouth and says “Call now, slut!”

            I dial, and the operator records the whole thing.  My shameless moaning, my mind racing as I think Oh my God am I actually telling a total stranger about how this stud is fucking me right now? (Of course I’m not....it’s just a fantasy!)  Not only can this woman on the end of the line tell that I’m a guy, she is recording every second of it, and I’m asking her to send a police car to come take my come-filled ass away, before I push it onto another cock.  She thinks it’s a joke, but I keep panting and moaning and insisting.

            Then, just as the stud sees the headlights of a squad car coming down the road, he pulls out, roughly yanks me around onto my knees, and grabs the back of my head.  As the cop car approaches – it’s still a good ways off, but how could it miss us? – he face-fucks me through his orgasm, the hot load hitting the back of my mouth and coating my eager tongue.  He jumps back into his truck, yelling that I had better meet him at his house before dawn if I didn’t want the phone pictures pasted on the wall in school.

            “On second thought, I know what you want, you naughty sissy-slave.  If you don’t meet me at my house before dawn, I won’t post these pictures in public!”  He then speeds off, and the cop car, now coming into the parking lot, starts down the road after him, but the officer must have realized he couldn’t catch the truck, or just radioed for someone else to pursue, because then the car turns back toward me!

            I can’t let myself get arrested, what kind of hooker would I be?  Besides, as much humiliation as the arrest would bring, seeing those pictures of me whorified and and ass-fucked all over school, having classmates ridicule me and point and whisper – that would be by far the most horrible (remember, horribly humiliating equals amazingly arousing) thing ever.....I have to make it to his place and “persuade” him to take more pictures, maybe make a video to send his friends.  So I run from the car, my slut-sandals clicking on the tarmac, my nipple chains jangling wildly, my cheerleader skirt flipping to reveal my shapely ass......

            Naturally, things like that never happened.  Unfortunately.  But that skirt was real, and so was the stud....I remember seeing him, naked and glistening, his thick cock dangling in the locker room.  How many times did I come with the image of that cock stiffening against the roof of my mouth?

            Okay, perhaps “mostly heterosexual” was misleading.  But let me explain.  I am usually into girls, especially in real life.  But this is how my transvestite / hooker / exhibitionist / submissive / BDSM fetish-complex works:  when I’m “in heat” and playacting, I think of myself as a girl.  Now, I’m not into sex changes – that is definitely off of my Weird-Shit-Ometer.  But starting with panties and, as you’ll see, all the way up to shaving, water-balloon breasts, and wigs, I fantasize that I’m a hot, trashy girl.  The idea is that, like all exhibitionists,  I get OFF on turning people on.  So if I’m in drag and bent over the hood of a car being slam-fucked by a drunk lumberjack and a carful of frat boys drives by, I want them to honk and holler and be aroused just as they would at the sight of an bona fide hot girl being slam-fucked by a drunk lumberjack.  The beauty of it is, if it’s nighttime and I’m dressed up properly, they never tell the difference, and I come in my panties thinking of how I just got the kind of attention usually reserved for porn stars or Mardi Gras.  For me, it is the ultimate high, knowing that I can turn men on that way.  And the fact that I’m a dirty, perverted, pseudo-queer, cross-dresser only adds to the humiliation / naughtiness factor.  The only way to fulfill these fantasies without a man and a cock in my ass or mouth (or both! mmm) is with A) a transsexual, and that is also off of my Weird-Shit-Ometer, or B) a woman with a strapon, and while I am definitely into strapons, the illusion wouldn’t be as complete or legitimate.  Think about it: I want horny, half-drunk college boys (and high school boys and dirty middle aged men etc.) to see a man fucking a gorgeous, shamefully-attired female right out in public and I want that shamefully-attired female to be me.  I want to be the focus of perversity, humiliation, arousal, and lewdness.  I want the men driving or walking by to think Holy shit, look at that hooker get banged!  She must really want it! and I want them to U-turn and come back for more.

            I would go jogging at night around my neighborhood, into the sections under construction, and I would find a secluded (but not really secluded) cul-de-sac, strip naked save for clothespins, and stand spreadlegged against a lightpole while I masturbated to climax, eyes on the streets behind me, heart jumping with fear – with hope – every time a car whooshed by, wondering if they glanced my way.

            My underwear collection slowly increased, and I actually did run naked from the cops once.  Then I moved up to where I am now, about three hundred miles across the state line, from one capital to another, and I really blossomed.  Living with a friend from high school – a fairly hot, female friend from high school – I was able to branch out and expand.  I started wearing her shoes – only the high-heeled, slightly sexy varieties, of course – when she wasn’t home.  She had so many pairs it was easy to nab an old set of strappy black closed-toed 3” heels.  I would put on my favorite matching silver-leopard print thong and bra and strut around, loving the way my calves and hamstrings toned and tensed in the heels.  I would pull on a jacket and a loose pair of running pants and walk around the apartment complex at night, slowing inching the waistband of the pants down to reveal the panyline and letting the jacket hang open to show the front clasp of the bra.

I wore my cheap, tarty panties to work at – should I tell you? oh fuck it why not – Panera Bread, knowing that the back of my bikini line or g-string was evident when I bent down to clean.

            I slowly grew bolder, and one night I wrapped a scarf around my head and closed the jacket to conceal my lack of breasts.  I pulled on black fishnet pantyhose beneath my favorite thong and zipped up my roommate’s under-the-knee, skintight black leather boots, the kind that are equally at home beneath a schoolteacher’s prudent knee-length dress and a hooker’s miniskirt.  The apartment complex bordered a fairly major street that ran just west of campus (which campus? it’s a major one, and if you want, maybe I’ll tell you), and I walked out to that road, waiting in the tall bushes back from the sidewalk.  Because of it’s proximity to campus, the road was very well-lit with antique-looking “gas” lamps, and the sidewalk was just against the curb.  I stood there, shivering in the early spring predawn, and waited until a pair of headlights pulled out of the gas station down the street.  I was giddy with alarm and arousal, keeping my cock tucked securely back in my thong as I yanked my pants off (they are the kind with snaps all down the sides, terrible for actually playing sports in, but great for a slut in drag).  I pulled the ends of the pant legs over the heels of the boots and, more excited than ever before, I stepped out onto the sidewalk ahead of the glow of the headlights.  Of course the car could see me easily even from a good distance, and I kept my hips cocked back, my feet one in front of the other, wagging my exposed ass with my hands in the pockets of the leather jacket – I kept it wrapped tightly around me, allowing me to pull the hem up above my waist.  Let me just add here that I have a very shapely ass for a guy – this comes from experience of men catcalling and... well, other things.  Anyway, I strutted for all I was worth, and the car passed not five feet from me.  I don’t remember the details of each car, but I pulled those pants on and off for at least half an hour, and the first time someone honked and catcalled, let me tell you, I was breathless.  It was all I could do not to yank the thong down right there and spew my load.  Eventually a large van passed by me slowly – I saw the driver crane his neck and I obliged him by turning saucily on my heel and keeping my best side presented to him.  I even put one hand against a street sign and dipped low, keeping my feet far back and wide apart and wagging my ass like a poledancer.  The van u-turned and came back by, almost coming to a stop.  Knowing my hasty hooker disguise wouldn’t hold up under close inspection, I kept trying to maintain a medium distance, close enough to tantalize.  The van honked three times and then sped away, and I was filled with disappointment.  I learned that night that, even though I had just experienced a higher state of arousal than ever before in my life, I wanted more.  I wanted the driver to hop out and fuck me just like I imagined the soccer stud doing.  I wanted him to toss me in his van and take me to his basement and duct-tape a funnel to my mouth and whip me while ten of his construction-worker buddies circle jerked into it.  I wanted him to trick me out in a wildly unrated hooker costume, shove me in his van, take me downtown on Saturday night and...

            .... The van pulls into the alley and parks behind the crowded campus nightclub.  A large, rough looking man steps out and opens the rear doors, emerging a few seconds later leading a tall girl by a leash and collar.  The girl is obviously a whore. She has a hot pink fishnet shirt stretched tightly over a black spaghetti-strap top.  The fishnet is a long-sleeved affair with holes for her thumbs, and both shirts stop well above her navel.  Her large, shapely breasts bob enticingly as she steps down from the back of the van, landing on the four-inch heels of black leather boots that hug her athletic legs to just below her knees.  Above those, her pantyhose (hot pink fishnet) hug her toned, smooth thighs all the way up, disappearing under the hem of a black miniskirt so short it almost isn’t there.  The skirt is tight – but just loose enough so that the light Midwestern breeze, carrying the strong scent of her cheap perfume, can lift the thin material and provide teasing glimpses of the sculpted curve of her ass.  Her nail polish, her heavy eyeshadow, rouge, and frosted lips, and her long wig all that same screaming shade of whore-pink.

            The man reaches back into the van and brings out a large posterboard sign with a chain attached to the top corners.  The pink-haired harlot obediently dips her head and allows him to slip the chain around her shoulders, and the posterboard cutout comes to rest against her ample chest.  The few college students who have passed by the alley’s entrance on their way to the front of the block and the clubs have stopped to stare and whisper, and they see the man remove the leash from her thick black leather collar and give her a brisk swat on the ass to send her on her way.  Hips swinging like a dancer on the runway, breasts bobbing with every loud click of her heels, the slut makes her way toward the small (but growing) group of onlookers.  They see her sign in the dim light of the sodium streetlamps, and the catcalls begin before she passes them and turns left, toward Main Street and the front entrances of the half-dozen busiest bars and clubs in town.  Her energetic pace and wagging hips only cause her miniskirt to ride and bounce higher, and once out of the confines of the alley, the wind picks up.  Calls of “Oh my God look at that ass!” and “Hey, baby, slow down!” echo against the brick walls.  Her lacey hipster panties leave the bottom half of her luscious rear end totally exposed save for the taut crissccross of pink fishnet.  She turns left again, onto Main, and the motion sends the hem of her skirt twirling out around her hips.  The boys behind her follow closely, chatting and whistling, so that even those clubgoers who might not have seen her coming turn well in advance and stare, many of them open-mouthed, as she approaches.  Several girls laugh or comment, more than one of them yelling compliments as dirty as the boys’.  One of her followers becomes brave enough to reach under her flapping skirt and squeeze her ass, and she stops in her tracks, flips her pink locks over one shoulder, and drops him the sauciest, most suggestive wink she can muster, opening her mouth just enough to bite her lower lip lightly and then slowly roll it out from under her sparkling white teeth.  Her tongue darts out to lightly caress her upper lip, she winks one more time, and then she’s on her way again, strutting down the sidewalk before the stunned boys even know that their cocks are pushing against their jeans.

            Honks, catcalls, and a fair crowd of partiers (girls as well as boys) follow her back into the alley, where the van and her large attendant are waiting.  She struts up to him, turns, and drops to her hands and knees on the pavement without being told.  The sign hangs forward between her arms until the rough man plucks it deftly and raises it before the crowd.  In the red neon light of a nearby bar, the black lettering is plain against the white posterboard.

 

            CUM-LOVING SLUT

            IF YOU FOLLOW ME,

            I WILL SWALLOW YOURS

 

            The college guys are tentative initially, not knowing if it’s some kind of joke and not wanting to be the first to step forward, but it isn’t long before a stiffening cock pushes past her frosted pink lips and finds the pad of her tongue.  Her panties rub enticingly against her own cock – because of course this sextoy bimbo isn’t a girl at all, she’s a dragged-out sissy boy.  She’s face-fucked repeatedly, slurping noisily and letting thick ropes of spit and pre-cum dangle from her lips between mouthfuls of dick, pulling back every so often to gasp breathlessly and look into the eyes of the man she’s sucking off, batting her thickly-lined lashes.  Much of the come is dripping down her chin, splashed across her bulging tits and the front of her skirt, or puddled on the asphalt between her knees.  More of it is on her cheeks and down her throat.  She takes a boy’s cock all the way in, opening the back of her throat and sliding her lips down the shaft until she can feel the warm velvet of his balls against her chin.  Her hands are clenched on his ass as she chokes, and tears start to squeeze from her eyes.

She abuses herself and lets them abuse her, gagging on their semen and loving it.  Between cocks she bends down to lick hungrily at the growing pools of spent love-butter on the ground.  As she does so for the sixth time, she feels strong hands grab her hips and tug the skirt up over her ass.  Both the pantyhose and the panties beneath are crotchless, and her rough-looking escort wastes no time providing lubricant.  Soon she is bucking wildly as she sucks, taking it hard from both ends, feeling like a bitch, a mindless animal, a dog in heat.  She pants and moans like a dog, and when they’re done, her handler pushes her up against the side of the van and yanks her own cock out from behind her miniskirt.  By now the crowd has dispersed, and he fucks her mercilessly, slamming her against the vehicle and pumping her cock as well.  She begs him for release and he gives it, filling her ass with a final load of come as she shoots hers against the van.  She slumps against the cold metal, her legs weak as she tucks her member back into hiding beneath her skirt.  She straightens her come-drenched wig, licks the fresh lines of sperm and fluid off of the van, and then obediently hops inside, knowing that a shower, a change of clothes, and a short ride to the next town is all that stands between her and another cock buffet.

 

Chapter Two will be under way soon....there have been so many dress-up sessions and field trips to the city streets, I have to gather my thoughts and remember them all.  If you liked what you read, then please e-mail me at sissy_slave_Sara@hotmail.com , and don’t forget those are underscores, not spaces, between each word.  It’s important to me that other voyeurs and exhibitionists are turned on by the shameless display of my innermost, dirtiest fantasies and confessions.  If it turns out that anyone out there happens to live near a certain state capital, then who knows, maybe they’ll get to see slave Sara in action....