*This story is a work of fiction - it’s a bit long, but I hope you enjoy*

*While this hasn’t happened to me, I love the fantasy and the concepts in it – drop me a line if any of this interests you, I’d love to hear your thoughts!*

I used to be such a good kid, now I’ve been forced to become some nasty guy’s little fuck bitch. What happened?!

I was 20 when this all happened, I was enrolled at my city’s university where I was studying business. I come from a really strict, religious family that put a lot of pressure on me to do well. I was pretty small for my age, kind of had girlish features. I had black hair that I normally tied back in a small ponytail, I thought it made me look a bit edgier, but it really just helped to make me even girlier now that I think about it. I used to be on the swim team, so I had a nice toned, if slight body, it had also got me into the habit of shaving myself (normally head to toe).

Anyways, enough about me, here’s my dirty little secret (well it was my dirtiest secret until now): I LOVE cross-dressing. I’d first heard about it on the internet, probably when I was about 19. I had been way too afraid to try it though, as I was terrified my parents might catch me (I was still living at home at this time). But it turned me on so much. I’d spend hours at night playing with my 6 inch cock, pretending I was all dressed up like a slut. I’d never told anyone about this side of my life as I knew my parents would disown me (literally) and I thought my friends would think I was a freak and ditch me.

This went on for the best part of a year until I finally decided that it was now or never. I secretly got myself a credit card and ordered some sexy lingerie. I had always loved the 1950’s type look and I got myself a 8 strap satin underbust corset, a pair of fully fashioned black nylon stockings with deep welts, black satin opera gloves, a black satin thong, a sexy black choker and finally a pair of 6 inch black patent pumps to set it all off. I had butterflies in my stomach when I got the notice from the post office that my package had finally arrived!

I lived uptown and had to take the subway to get to the downtown post office depot to pick up my stuff. I grabbed a few joints I had rolled, thinking that I might need these to calm my nerves, I was so excited! I went to the post office, with my face bright red (I had no idea why I was so embarrassed, they didn’t know what was in the package) I got my box of naughty treats! I stuffed the box into my backpack and pretty much ran out.

I stopped in the parking lot next to a coffee shop that my friends and I used to hang out at to try to think things through. I was trying to figure out a way I could try my stuff on without getting caught, my mom and dad were at home, so that was out. What could I do? I sat down in the parking lot and smoked two of the joints. Seriously high and a bit bummed out, I thought I’d grab a coffee and see if inspiration struck me.

In my weed induced haze, I ordered my coffee, as I turned to find a table I let out a soft groan. He was there, ugh! ‘He’ was JP, I didn’t know what his name was but he hung out at this coffee shop a lot and always tried to talk to my friends and I. We made fun of him a bit but mainly tried to avoid him, he was a pretty creepy guy.

He must have been about 50 years old; he was kind of balding, had a big gut and always seemed to have 5 o’clock shadow, thinking about it he kind of looked a bit like Ron Jeremy. He looked kind of mean and reeked of desperation, if you get what I mean. Anyways he was there and was motioning me to join him at his table. If I hadn’t been so high I probably would have taken off. I wish I had now.

I wandered over to his table, I kind of stumbled as I sat down, almost falling. He let out a laugh, I’m pretty sure he could tell by my actions and eyes that I was pretty high.

“How’s it going Sal?” he said to me.

“Uh yeah, pretty good” I responded kind of lamely.

“Wow, you actually decided to sit down with your old pal Carl, how nice.” He said, an edge to his voice as if he was kind of mad at me.

“Uh yeah, I guess” was all I managed to mumble. I really wanted to get out of there to try on my stuff, this conversation was killing me.

Anyways we got to chatting a bit, small talk mostly, but he did ask a lot of questions about me, my situation, my friends and family, the whole time staring at me. He had these crazy eyes, which kind of freaked me out a bit. I answered his questions, for some reason I really didn’t want to piss him off.

Then he just flat out asked me “Hey, you high Sal?” I just kind of nodded dumbly, still in a little bit of a stupor. He then said “Cool, let’s go out and smoke another one”, I just nodded again and followed him outside into the alley out back of the coffee shop.

As we sat there smoking away, my inhibition (and good sense was starting to fall away – I was really wasted now) as a light bulb went off in my drug-addled brain. “Hey Carl, you live alone right?” he looked at me, suspiciously, “Yeah, so what?” he responded sharply.

“Uh…well…I’ve got this thing…and you seem like a cool guy and all…” I started to stammer. He just looked at me coldly and said “What the fuck are you talking about?”. I turned a deep shaped of red, but I was so high (and weed makes me so horny) I gave him my backpack and said “Open it, but please…please…please…don’t tell anyone. I’m begging you!” I whined a little bit.

He cracked an evil grin as he opened and looked inside my backpack, seeing all my pretty things in there. He let out a little whistle before he said “Well, what do we have here? You like dressing up like a girl?” his grin positively devilish now.

I just nodded and said again, definitely begging now, “Look, it’s not a big deal, you know a lot of people do it. It’s just that if my folks or friends found out they’d kill me. I mean literally kill me. And I thought that you have your own place and maybe you might…” I trailed off as he interrupted me.

He spat back at me with some venom “Oh you thought that fucking loser Carl would let you dress up in his apartment, so you could get your rocks off. Your friends would never find out because they never talk to me.” His face was really made now. Then all of a sudden he softened, his voice mellowed and he thought for a second before replying.

“Well… hmm… maybe it would be okay after all little buddy. Why don’t we head over to my place now? You can do whatever you like dude.” His voice and manner were so pleasant (and I was so messed up from the weed) that I felt so relieved and thankful.

“You’re the best man! I so appreciate this! You’re awesome man!” I gushed enthusiastically as I followed him to his car, kind of kissing his ass the whole way back to his place.

He opened the door to his apartment. It was pretty gross, in a seedy part of town. Definitely not the kind of place you’d want to be caught out at night in alone. His place was a rundown, dirty, one bedroom apartment. There was a TV in front of a shabby 3 seater couch, the kitchen was in the next room, the bathroom down the hall and the door to the bedroom was closed. I was so happy to be there, in my little dress up place.

He pointed at his bedroom and said “You can do anything you want while you’re here, I don’t mind. My only condition is that you have to show me your little outfit once you’ve got it on. Deal?”. I thought for a second, my drugged and horny brain trying to work.

“You won’t take pictures or anything will you Carl? Like I said, if anyone found out about this, I’d be dead. My life would be over!” I said, my voice obviously panicky. He just smiled reassuringly and said “No way man, it’ll be our little secret. I promise.” I was so horny and fucked up that I think I actually believed him. He said, in a firm voice, “Get in the bedroom and change, come out when you’re dressed.” I nodded and went in, closing the door behind me. My stomach was full of butterflies, I was so excited!!

I quickly took my boy clothes off. I then slowly rolled the stockings up my legs, the feeling making my cock twitch in excitement. I then put on the corset, I struggled to get it tight, but I eventually managed (it gave me a great hourglass figure) then I attached the garters to the stockings. I then slipped on my little black thong and tied the choker around my neck. I then stepped into my sexy ‘fuck me’ heels and did up the little strap around my ankle. Finally, I slid on my satin opera gloves.

There was a mirror in the room, I took a good look at myself and I thought “fuck, that’s hot!”. I actually looked pretty damn sexy, the girly lingerie really setting off my already girly frame. My muscular legs looked gorgeous in their nylon stockings, damn I just looked sexy. My panties were being stretched by my hardening cock. I was so turned on I could have stayed looking at myself in the mirror for hours. But I remembered my deal with Carl.

I thought  to myself ‘Alright, I’ll just go out, let the dirty bastard have a look, then I’ll head back in here and jerk off’. I called out to Carl to say I was coming out, I opened the door and then ‘flash!’. My eyes were blinded by a succession of bright lights, I stood there dumbly for a minute, the drugs making my brain move very slowly, then I saw the source of the light. It was a camera. Carl was taking pictures of me dressed up like a dirty slut. My mouth went dry, I’m sure a look of pure panic covered my face as I just gawked at him taking photo after photo of me. He was laughing the whole time. It was a sadistic laugh.

I finally managed to squeak, “Carl….wha…..what are you doing?”. He just looked at me laughing, still snapping pictures “That’s it, work it baby!” he chuckled.

I snapped out of my fog, I got angry, I yelled at him “Fucking stop this shit you bastard! This wasn’t part of the deal! I’m going to fucking KILL YOU!” I screamed.

He stopped taking photos for a second, put the camera down on a table next to the couch and calmly shook his finger at me. “Oh no you won’t Sal” he said, his mouth spreading into a cruel grin “Or, do you want me to show all your friends these pictures?”.

I stood there, teetering in my heels, my legs wrapped in shimmering nylons. I knew I was done for. I just shook my head.

Carl continued “Or, you know what I think? I think you’d do anything to not have your parents find out about this, wouldn’t you Sal?” he laughed sadistically again “or should I say Sally?”. He thought that was really funny. “You know what else I think? I think you’re going to do whatever I say, so that I don’t share these with everyone you know. Isn’t that right Sally?” he stood there obviously waiting for an answer.

I didn’t say anything, I was looking at the door, thinking that I’d just bolt, get out of there as fast as I could. Then I looked down at myself, dressed in this outfit, my legs tightly encased in nylon, my feet hobbled by these stiletto heels. Where was I going to go like this?

He walked over to me, grabbed me by the throat. He was so strong, I had no idea. He held me tight for a minute and then hissed at me “You’re going to do everything I say, or I’m going to post these pictures all over the net. You’re mine now bitch. You do EVERYTHING I tell you. Got it?”

I just nodded my head. I just wanted to get out of there. I wanted to be anywhere but there. It seemed to satisfy him, or so I thought, as he walked out of the living room into the bedroom. I heard him rummage around in there for a few minutes before he came back out, holding a video camera, it was pointed straight at me. My mind screamed. Fuck! He’s taping me now!

He turned the camera on himself for a minute and said “Hello viewers! You’ve just been introduced to Sal! He’s new, but just so you know, here are his details!” He then went on to say my full name, address and phone number. He then held my drivers license up to the camera as proof of what he’d just said (he must have dug those out of my pants when he went into the bedroom to get the video camera). He put the camera on a tripod and then turned it back on me and asked “Is this all true Sally?” he said with a laugh.

I stood there, still and silent for a second. He gestured aggressively from behind the camera to say something. He pointed at his camera on the table. I got his drift. Either I did what he said, or my life was over. He then held up my phone, he was cycling through all my contacts, phone numbers, email addresses of everyone I knew. He grinned like a devil. I gulped. I was terrified.

I smiled weakly at the video camera and said “Yes…uh…it’s all true”. He then made motions, like he wanted me to say more. I continued “I’m…just a little….crossdressing slut….I’ll…do anything…. anything you want!”. He smiled at me and turned the camera off as he walked over to me.

“There you see, that wasn’t so hard was it?” he said with a sickly sweet smile. He got real close, his face just a few inches from mine, I could feel his breath on my neck as he leaned into me. I felt his hand drop behind me and brush against my ass cheeks, my satin thong doing nothing to protect me. “You’re not making fun of me now are you, BITCH?” he hissed the last word at me. “I’m going to make you pay for treating me like shit. I’m going to do things to you….” He trailed off there for a second, letting my imagination run. “And if you don’t do what I say…. Well I’ve got pictures and video of you Sally, you being a naughty little girl, and everyone’s going to know.” I stood mute for a second and then let out a little sob of terror and desperation. He just laughed.

He went back to the camera and turned it on, before slowly walking over to me, the camera filming the whole scene.

I felt his big hands start to kneed my ass cheeks roughly, he was really digging into my firm globes. He started to kiss my neck, his rough five o’clock scratching into me a little bit. He then started to stroke my hair with one hand as he leaned in and kissed me on my lips. I felt his nasty tongue digging around in my mouth. He held me like that for a while as he groped my ass with one hand and forced his tongue down my throat.

He then turned to the camera and said “See, little girls love to be kissed, don’t they Sally?” I felt so humiliated with him calling me Sally and girl but there wasn’t anything I could do. I just nodded at the camera and said weakly “Yeah, it’s so hot”. He then started to grind himself into me. I felt ‘it’ against my leg. I was terrified.

I could feel this massive snake in his pants rubbing against my body, sensing this he grabbed one of my gloved hands and placed it on his crotch, rubbing it against his pants covered cock. It felt huge, at least twice the size of my cock. “Rub it bitch” he ordered, as he let go my hand. I kept rubbing it, feeling it get slowly larger and larger.

He moved his hand around and started to grope at the front of my black satin thongs, rubbing at my very flaccid cock. “Awww what’s the matter little girl? Is your little bitch-cock not working?” he said with an evil laugh “Let me help you with that” and he went to his bedroom and quickly returned with a blue pill in his hand. He then ordered me “Open your mouth slut” which I did he then stuck the pill in and I swallowed it (I now realise that he’d just fed me a Viagra). He pushed two fingers into my mouth, I gagged a little bit. “Don’t worry, you’ll get used to this…. And more” he whispered as he started to pump his two fingers in and out of my mouth, forcing me to suck them for what seemed to be a very long time. He then quickly pulled them out of my mouth and announced “It’s time for the main event bitch. Get your ass over here and unzip my pants”

I nervously walked over to him “Do it bitch” he hissed at me. My shaking gloved hands undid his pants and slowly worked his zipper open, his pants dropped to the ground. I let out a very loud gasp of shock. His cock was huge. I mean huge. It was about twice the size of my cock. If you’ve seen any porno movies with Mandingo, then you know what kind of size I’m talking about. I stood there just staring at it, my mind racing. He jammed a bottle under my nose and said “take a deep breath. I did and my head swum (it was my first time using poppers) he then ordered me to “Stroke that big cock bitch”.

I took the monster in my hand, wow it felt so hot! And slowly started to stroke it. He let out a happy moan and closed his eyes, obviously enjoying the moment. It was getting harder and harder. I don’t know what was coming over me, if it was the weed still, the poppers or the Viagra but I found my cock was starting to get hard in my little satin thong.

I felt his hands on my shoulders, trying to push me down on my knees. I resisted at first, but damn was he ever strong. I finally got down on my knees in front of him, his huge cock staring me right in the face. I didn’t want to do this. He started to jerk his cock just about an inch away from me, then suddenly he started to smack me in the face with his big snake, laughing while he did it. I felt so humiliated.

He then rubbed his cockhead along my lips, I felt his pre-cum dribbling out, kind of leaving with cum lipstick. He rubbed his cock all over my face then he said “Open wide bitch, this party’s just about to get started”. I let out a little whimper but knew there wasn’t anything I could do to stop this, so I opened my mouth and knelt there waiting for this to happen.

He slowly fed his massive cock into my mouth, it was huge, my mouth was stretched to its limit. He then started to pump in and out of me, pretty much using my face like a pussy. I started to gag and wretch as he pushed too far into my throat. Saliva and drool covered his cock and was dribbling off my chin splattering the floor and my legs. I looked out of the corner of my eye and I saw the video camera. It was recording all of this, I felt so ashamed and broken. He looked down at me and said “How’d you like that, cocksucker?” my eyes flashed up at him, angry at him calling me that “You’ve got my cock in your mouth now bitch, you’re a cocksucker. My cocksucker.” With that he shoved his cock deep into my mouth, making me gag loudly. He laughed as he continued to fuck my face.

He finally pulled out of my mouth, with me gasping and spluttering for air. My face a mess of spit and drool. He dragged me to my shaky high heeled feet and pushed me back onto the couch, he kind of dragged me across the couch so my head was hanging off the arm, he shoved his cock back into my mouth and started to really facefuck me. Drool and spit covered my face as I gasped to breathe while choking. He then reached over me and did something unexpected, he started stroking my cock through my satin thong. I don’t know why, given the circumstances, but this really turned me on. With the Viagra in my system my cock quickly grew crazy hard. The poor satin fabric was straining to hold my cock in place as he roughly rubbed my cock.

He pulled his big cock out of my mouth finally and said “Oh you like that bitch?” he laughed, making fun of my soft moans of pleasure. He turned to the camera and said “Look at this little slut, her little bitch-cock is so hard, she loves this!”. I was just moaning like a bitch in heat, squirming in ecstasy as he continued to massage my cock through the satin thong.

I was in heaven. Until he roughly grabbed my balls through the fabric of my panties and hissed “We’re not here for your enjoyment, we’re here for mine bitch!”. With that he pulled me off the couch and shoved me onto my hands and knees, with my face to the video camera. He stood over me, behind me, as he started to talk to the camera “Now, for your folks at home, you’re going to see me and my snake here” he gripped his cock as he said this “fuck this little virgin bitch. You’re going to see her moan like a little girl as I fuck her tight little bitch pussy. What do you have to say about this?” he said to me. I looked up and back at him, tears in my eyes as I said “Please….please Carl, don’t do this to me, I’ll do anything please…” I whimpered pleadingly. He just laughed and said again to the camera “Well, I’d believe her, if it wasn’t for the fact that she’s enjoying herself too much.” With that he pulled me up a bit so the camera could get a shot of my super hard cock, still straining to get out of my panties.

Carl then ordered me “Play with yourself Sally, show the people watching how much you love this, how much you love being a little cock teasing whore”. I let out a small sob as I pulled my thong down to my thighs, letting my 6 inch, crazy hard cock out. He laughed at me when he saw it and again turned to the camera and said “No wonder she makes such a good little girl, she’s got such a small little clit there!” turning to me again he said “Stroke it bitch and tell the camera how much you love this”. He put the vial of poppers under my nose again and I took a deep breath. My brain swam.

I started to stroke my hard cock right in front of the camera as I started to say all these nasty things about how much I loved sucking cock, what a whore I was, that I couldn’t wait for Carl to fuck my virgin hole. I was really getting into it. Anyone watching that movie would think that I was totally into this, that I was a real cock slut.

I then felt Carl’s big hand push me down so that I was on all fours, my ass to him. This broke me out of my fantasy and I was scared and ashamed again. I looked at him over my shoulder as he took his shirt off, exposing his pretty ample, hairy belly. He ordered me “Look at the camera bitch! I want everyone to see your face as I break your cherry.”. I whimpered a little as I turned to the camera, thinking that if anyone I knew ever saw this movie, my life would be over.

I felt him spray lube onto my ass, covering my firm butt in the liquid as he then started to work the lube into my crack. I felt something against my hole and I let out a little grunt as I felt his finger slide into me, pushing more and more lube into me. I gritted my teeth as he pushed a second and then a third finger into me as he lubed me up. He leaned over me, I could feel his fair gut against my back, and whispered “You’re going to love this Sally, I’m going to fuck you so hard. You came in here a boy and you’re going to leave a bitch” then he said to me more loudly, so that the camera could hear “Do you feel my fingers inside you Sally?” I just nodded at the camera and smiled weakly. Carl then said “And what are you, little Sally?” I was so humiliated as I responded quietly “I’m a bitch”. “What was that?” He said (I’m sure he had that evil grin on his face) “What was that?” I replied loudly, looking into the camera “I’m a little bitch!”. He laughed and said “And who’s bitch are you Sally?” I looked at the camera again, as I said, trying to muster as much dignity as I could “I’m your bitch Carl!”. “Good girl!” he cooed mockingly “Now get ready you little whore”

With that I felt him start to press his big mushroom cockhead against my tight hole. The pressure was immense. I gritted my teeth as he pushed it against me, trying to squeeze it into my ass. I let out a loud yelp of pure pain as he finally popped the head into my poor ass. It hurt so bad, I’m sure the camera caught the tears in my eyes. He stayed there for a sec and then started to push the rest of that massive snake inside me. It felt like he was re-arranging all my insides with his massive pole. I was making whimpering noises as the pain got worse and worse as he pressed deeper inside me. At one point I thought I was going to pass out.

After what felt like an eternity I felt his hairy belly press up against my ass cheeks. He announced “There bitch, I’m finally all the way in. That wasn’t so bad was it?” he laughed as all I could manage was a defeated, pathetic whimper. He then started to pump his cock in and out of me, slowly growing in speed and force. I don’t know what it was but the pain started to go away, and my cock (crazy!) started to get hard again (was I actually starting to enjoy this abuse?). He was really fucking me now, pumping his huge rod in and out of my abused asshole.

He pulled out of me suddenly and I whimpered at the feeling of emptiness, but he quickly flipped me onto my back, putting my stocking-clad legs over his shoulders as pushed his cock straight back into me. I moaned loudly as he re-entered me.

He sneered at me and said “Jerk yourself off bitch, let the camera watch you become a dirty whore”. I didn’t need any more encouragement, I grabbed my hard cock and started jerking myself off as he continued his assault on my poor hole.

I think he knew I was getting close to cumming and he did something I didn’t expect. He pulled me up, so I was almost folded over. He was above me, still pumping my little hole, but now my cock was pointed straight at my face! I couldn’t stop myself, I made a little girly noise as the biggest orgasm of my life swept over me. My cock started to spew rope after rope of my own sticky cum onto my face, into my mouth, my hair, everywhere. I had never cum so much before and my face was covered in it.

My head rolled and I noticed that the camera had caught all of that. Now that I had cum all the horniness was going away. Carl was still fucking me hard, but everything that had turned me on was now just so nasty. I was so ashamed. I looked up at Carl with tears in my eyes, I felt broken. He looked back at me with triumph on his face. He laughed at me and then spit onto my cum covered face. “You might be done bitch, but I’m not done with you yet” with that he pulled his cock out of me and rammed it back into me, as if to prove a point.

He kept fucking my limp, emotionally broken, body like that for what seemed to be ages. Sweat was pouring off of him as he mercilessly fucked my poor stretched asshole. Finally I heard a primal noise start deep inside him, it reached intensity and became a bellow as he pulled his cock out of my gaping hole. My body fell back to the floor and he straddled me, so my arms were pinned by his strong hairy legs and his cock was pointed straight at my face about an inch away. He was furiously jerking his cock. His face was a mask of rage and lust as he finally exploded, his cock was pumping out rope after rope of his nasty cum. I covered my face, went in my mouth, ran down my chin and pooled on my neck. My orgasm was nothing compared to his. I was a cum covered bitch when he was done with me.

When his orgasm was over, he kind of relaxed, while still on top of me, his huge cock lying on my face. He moved it around, mixing the cum around on my face. He let out a sign of complete satisfaction as he looked down at me “Wow, you are one serious cock slut, you know that Sally?” he laughed as he then pushed his cock head back into my mouth, to let the last drops (it was still a shitload!) of his cum flow into my mouth (which I was forced to swallow).

He looked up at the camera and said “That’s all for now folks. Thanks for watching! Sally would love to say goodbye, but a good bitch never speaks with her mouth open!”

With that he got up and turned off the camera. I was still lying on the floor, a mess. He turned to look at me and said “You and I are going to have a lot of fun bitch. Well mainly me really!”.

I kind of blacked out then, the sound of his evil laugh filled my ears as I slipped into a horrible sleep.