Category: Transsexuals & Crossdressers Stories

Bitch

by Dennis_St_John©

'I am ready, Sir.' I texted on my cell phone. 'Room 28.' A few moments later, the cell phone pinged and a return message appeared.

'You know what to do -- I'll be there very soon.'

I took a shuddering breath and looked at myself in the bathroom mirror. An angry frown marred the soft made up sissy face looking back at me, framed as it was by dark straight hair that framed my face. I checked the power blue eye shadow and black eye liners for flaws. They were as perfect as I could make them after long hours of practice, as were the bright pink, pouty lips outlined in a thin, dark pencil line around them.

I let out the breath in a long sigh as I looked down, seeing the soft, black lace bra that stretched firmly over my small girly titties. I sucked my breath back in as I ran my fingers over the hard sensitive nipples, feeling and seeing a slight blush color my face thinking how I'd taken the hormones to get them. Stupid really. Boys don't have titties like a young girl. I tried to think what had possessed me to take them in the first place. The thought of what it would feel like to have little breast for guys to play with while they abused me as I stoking my little sissy cock one night I think. Whatever the reason I now had them. What I hadn't expected was the problem hiding them as they grew, or the feeling of shame as they developed.

I ran my finger down my flat tummy, fingering the waistband of the black lace crotchless panties and the black lace garter belt hugging me around the waist. I knew I looked like a total slut with them and the smoke black, lace topped stocking tugging at the garter straps. I knew I was a little taller than my 5' - 8" now in my 4" strappy black high heel shoes. I shivered again, knowing I look like a complete slut dressed like this, but that is what the man wanted.

The steel snap hooks locking the wrist cuffs rattles softly as I reached up to smooth an arched eyebrow one more time, seeing the bright pink finger nail polish as well. I looked at the wrist cuff for a moment, then down to the ankle cuffs around each ankle. Soon I'd be kneeling in the center of the room with them hooked together and for a moment, I wanted to run. Where I didn't know dressed like this, but I didn't. This was what I wanted... no craved and the man was about to make it happened... again.

I supposed all this started in high school where I was the wimpy looking kid with long hair in a tangled mass on my head. All the bigger, older kids picked on me and the jocks beat me up every so often and called me a dirty little faggot for letting my hair grow that long.

One guy in particular, Derrick, loved to go out of his way to bully me, making my last year of high school a living hell. He'd grab his dick in the shower and wave it at me just to see me blush, saying ...hey faggot you want some of this meat in your mouth?... He and the other guy would laugh when I turned away and hid my tears in the shower water. The towel snaps left my butt stinging and red, my face as red with humiliation, but that wasn't the worse part.

Sometimes Derrick would half chase me home as he lived on the same block as me in the housing estate, shouting, run little faggot. Run fast before I catch you... Then one day he did catch me, in the park. This was a short cut home for me and mostly I didn't have any trouble. I knew that guys used the trees and dense shrubbery that dominated the center of the park as a place to go and make out, but only after dark.

That was the trouble. I had to stay late at school one afternoon and by the time I got out it was getting dark. I didn't think much about it was a walked home until I passed near the tree line.

"Hey little faggot. Get the fuck over here." I froze in place, recognizing the voice.

"W... what..." Seeing Derrick leaning against a tree.

"If I have to come over there and get you, I'll beat the shit out of you."

"What... no, please."

"Then get your faggot ass over here."

I hesitated, desperately wanted to run, but knew if I did he'd catch me and he'd probably beat me up even worse. Dragging my feet, I slowly walked towards him, almost crying. When I got closer, he reached out, grabbed my arm, and dragged me deeper into the trees and bushes. Once we were well out of sight from any one walking passed he pushed me against a large tree, pinning me there and slapped my across the face.

"I told you I'd get you little faggot."

"W... what do you mean?" I sobbed, the left side of my face stinging from the slap.

"Unless you want me to beat the crap out of you every day from now on, you are going to get down on your knees and suck my cock."

"WHAT! No... you wouldn't." I blubbered. He slapped my across the face again.

"Are you deaf sissy bitch? I said that unless you want me to beat the living crap out of you every day from now on you'll get down on your knees and service my cock." I couldn't believe he'd say something like that to me. I was stunned... he couldn't be serious... could he? Then he unzipped his pants, took out his semi hard cock, and showed me.

"On your knee faggot. I'm going to fuck your sissy fag mouth with my nice big cock."

"Oh god! No... please... I'm not a fag..." I blubbered.

"I don't give a shit. You're going to suck my cock anyway."

"Noooo... Pease!" I begged.

"Then I'm going to beat the crap out of your everyday until you do."

"God no... please... don't beat me up any more." I pleaded.

"You going to get down on your knees and suck my cock?" I looked up at him, pleading him with my eyes.

"Promise not to beat me up any more..." I couldn't believe I was saying it.

"Deal. Suck me off till I cum in your mouth and I promise not to beat you up any more, sissy fag." He laughed as he said it.

"Don't tell anyone I did it... please." I begged. He laughed again.

Fuck no. I want you all to myself. Lets the other guys get their own cock sucking sissy faggot. With tears of shame running down my face I dropped to my knees and he immediately grabbed me by the hair and shoved his cock head against my lips. I shuddered in discussed, smelling his manhood and pee.

"Open your fucking mouth bitch and lick the head of my cock." There was something slick and musky smelling on the tip of his cock, and he ran the head back and forth over my lips.

"Fuck yeah, sissy lip gloss. Just what you need. Now lick."

With tears running down my face, I put my tongue out and started licking the head of his cock. It was horrible, vile and shamefully dirty and even as I licked, he pulled my hair and head forward and shoved the head of his cock into my mouth.

"That's it bitch, wrap your lips around the shaft of my cock and start sucking." I sobbed in shame and did what he ordered as spikes of pure humiliation shot through me.

I couldn't believe this was happening to me, or why I was letting it happen. Derrick was now grunting in pleasure as he fucked my mouth, slowly pushing his cock deeper inside with each thrust. My jaw hurt from being stretched open so far to accommodate his fat cock, and my hair hurt from him holding and pulling on it.

"Oh yes... what a good little cock sucking faggot bitch you are... keep sucking me you filthy faggot... yeah! Fucking A! Suck me bitch." The head of his cock hit the back of my throat and I gagged, but he didn't stop. It only seemed to egg him on more.

"That's it faggot, choke on my cock... Ohhh fuck!!!" With one last thrust, he shoved his cock in as far as he could and erupted into my mouth. "Oh fuck yes... suck all that nasty cum out of my cock, you pathetic faggot bitch... swallow it... swallow it all."

Not that I had much choice as most of his cum shot straight down my throat, almost making me choke. The rest filled my mouth and I couldn't believe someone could shoot the much cum; I never had in my life.

"That's it, swallow it bitch."

I shook my head and tried to say no, but he jerked my head back before I could say anything and pinched my nose. It only took a second for me to open my mouth to gasp for breath, and when I did, Derrick's cum slid down my throat. It was so horrible I started crying again. He finally let go of my hair and pushed me to the ground, laughing as he tucked his cock back into his pants and zipped them up.

"Not bad your first time, bitch. You'll do better next time, won't you?" He patted me on the top of my head. I felt ashamed even to look up at him. He meant to use me again.

"You take care of my cock and I promise not to beat you up any more, or tell anyone. I'll also make sure the other guys don't bully you either." He must be feeling a little guilty about what he'd done to say that, but I simply nodded, unable to say anything.

"Go home sissy fag and clean yourself up. You're a fuck mess, and wipe that cum off your chin or someone will know you've been sucking cock."

With that, he pushed off between the bushes and quickly vanished in the tress whistling some odd tune. I just knelt there for a while, angrily wiping his cum off my chin. Wrapping my arms around my dirty knees, I sat there and cried.

Derrick used me a lot after that first time, but as he promised, neither he nor the other guys beat me up. A far as I could tell he'd never told anyone else what he was doing to me. One time he told me to get a pair of panties and a skirt from somewhere and be wearing them when he came to this place in the woods. The first time I didn't and he pushed me over a downed tree, ripped my pants and underpants down and whipped my butt with a thin, whippy branch. That hurt a lot and I cried as my hot shame filled tears dripping on his fat cock as I sucked him off.

The worse day was when he ordered me to be here, fully dressed in panties, bra, skirt, blouse and pink lipstick and to wait there with the front of my skirt pulled up to show my panties off. That was when he bend my over the fallen tree and raped me. Thankfully, he used some sort of lube so the pain was minimal. It was the feeling of shame and humiliation that made me cry, knowing it was my fault for doing what he ordered and letting it happen. I was now his bitch. So, here I was, almost ten years later, dressed up like a sissy bitch waiting for another man to come and use me. This time I knew it was going to be worse, and yet I couldn't stop myself from doing it.

Swishing out into the hotel bedroom, I walked to the door and unlocked it so he could just walk in. I then went and knelt down at the end of the bed and placed the ball gag in my mouth and tightening the head strap around my head tightly so I couldn't spit it out. The blindfold came next, sobbing softly as I plunged into darkness. By feel, I hooked the wrist and ankle cuffs together with snap rings, effectively trapped myself like this so I wouldn't have any opportunity to resist, no matter what he did to me. I could, with a little difficulty, get the snap ring off, but it usually took me all of ten minutes not being able to see behind my back.

This was Derrick's fault, he'd turned me into a crossdressing faggot sissy bitch, and no matter how hard I tried after my family moved away that summer, I couldn't stop thinking about what he'd done to me. I found myself jacking off thinking about it first, thinking about the horrible, dirty feeling of shame and humiliation I'd felt. It shouldn't have turned me on, but it did. I ended up crossdressing in secret, spanking myself, using a dildo to fuck myself in front of a mirror so I could watch. In the end I found I couldn't stop, and the only relief was then I moved out on my own. Now I could dress and tie myself up for hours on end with a soft dildo in my mouth and another buried deep in to sissy cunt. I even tried finding a spanking machine so I could get spanked while tied up as well, but I never found one. In the end, I knew I needed a man to do all the things I craved, just like Derrick had, and at last finding one on line. Now I was here, dressed like a sissy faggot bitch, Blindfolded, gagged, and tied up ready to be humiliated and abused by a strange man the way I wanted.

I heard the door open, then close and lock, his footsteps on the carpet. The flash of a cell cam penetrated around the edge of the blindfold, sobbing softly as he took photos of me. Now I really started to feel pathetic. So far, he hadn't uttered a word, but then again he didn't need to. He'd told me what he was going to do to me on line, and I'd agreed. Maybe he thought it was a trap, or that I was not for real. Now he knew different.

Without a word, he simply picked me up, threw me onto the bed, and forced me back into the kneeling position. I felt him touching my wrist and ankle cuffs, as if examining them, until I heard the clicks. I shivered as my exploring finger felt the padlocks he'd locked through each of the rings; know that I was really trapped now. A shiver run up my body, fear, anticipation, I wasn't sure what but it was something I hadn't expected. A finger touched my chin, pushing up, and I lifted my head as a soft sob escaped around the ball gag.

The touch of something cold and rough being placed around my neck send another shiver running up my body as he buckled and then locked a collar around my throat thereby making me his bitch. He them forced my head down onto a pillow and I suspected what he was going to do next. I was right when he became spanking me with what felt like a wide leather strap. It hurt and I squealed around the gag into the pillow, knowing that no one outside of the room would hear my muffled screams as he beat me even harder. By the time he'd finished I was a sobbing, whimpering wreck, unable to resist when he lifted my head and pulled the ball gag out.

I only just managed to get my breath before he roughly forced him thick cock into my mouth. I breathed as deeply as I could as he fucked his way deep into my mouth and down my throat. Gasping for breath each time he pulled out. I no longer gagged, as I'd practice a lot with the dildo in my mouth while tied up. I heard him moan as he continues to fuck my mouth hard and fast, keeping my bright pink pouty lips wrapped tightly around the shaft of his cock like a good little dirty little cock sucking sissy fag slut should. It was exhilarating, shameful and humiliating all at the same time, and I was strangely happy.

All those horrible, wonderful dirty feeling I'd felt when Derrick fucked my mouth all those years ago came rushing back to me again, and like an obedient little bitch he'd made me I sucked as hard as I could. I heard him groan louder, feeling his cock head slipping in and out of my throat, hoping, praying he shot his load. He didn't, he simply pulling his cock out with a loud pop as I continued to suck. I wanted his thick cock in my mouth, and almost started pleading with him to continue, but he didn't.

He must have placed my sideway, as I felt him move around behind me and pulled my legs open wide. I knew what I was going to feel next. The head of his big cock at the entrance of my boy cunt. I gasped as three fingers went in first, knowing he'd find it slippery from lube, ready and waiting for his cock. Then I felt it, hard, probing and with a quick hard thrust he had the head of his cock inside me. I moaned like a cheap ally slut then, tears of pain and pleasure running down my face. His hands gripped my hips, tight, commanding as he rammed his cock all the way inside me.

"Ohhhhh fuck... yesssss." I moaned.

He took me then, fucked me hard, almost brutally, demanding my total submission to his cock. I lowering my head to the bed and lifting my ass for him to fuck harder and deeper. He did, hearing him grunt and groan in pleasure as he fucked me like a dirty bitch. I started bucking back on his thrusts, giving myself to him and his wonderful cock. In all he must have fucked me for ten minutes before he drove his cock all the way inside me and held it there, feeling it pulse as he shot his cum deep inside me. All I could do was thrust back, moaning and squealing in pleasure. I was a slut, a dirty little crossdressing sissy homo faggot slut and I craved his wonderful thick 8 inch cock fucking my boy cunt over and over again.

"Ummm good fuck." He muttered as he gasped for breath, hearing the soft rasp of a zipper as he put his cock away.

"What a great little obedient cock sucking bitch you turned out to be. I like that." There was something odd in the tone of his voice that started to make me nervous. His finger stroked the side of my face for a moment, and without warning, he pulled the blindfold off. I blinking, trying to get my eye in focus as I looked up at his face.

"Nice to see you again, Kevin. Been a while." He laughed. It was a laugh I recognized rather than the face. It felt as if my heart stopped. "Oh god!" D... Derrick!" I spluttered, shaking as a cold shiver ran over me. It was Derrick, an older and heavier Derrick

"Hello bitch. I see you still remember me." His smile wasn't nice. I futilely jerked at the cuffs, sobbing as I remembered he'd lock them on me, understand now why.

"Took me a while to find you, but now I have, we can carry on where we left off."

"W...what do you mean?" I had a sinking feeling as if a large ice-cold rock was sitting in my chest and slowly sinking into the pit of my stomach.

He laughed as he emptied my wallet I'd hidden under the mattress. Everything went into his pocket, my money, credit cards, driving license. The rest he tore up and dumped into the garbage can along with the now empty wallet.

"You cost me a lot of many back then you know. I almost had you ready to start pimping you out. All dressing up like a high school bitch and waiting for me in the woods with your skirt pulled up to show off your faggy panties."

"W... what," I swallowed hard, "what do you mean... about the money?"

"Oh that. Well pimping you out as a sissy fag high school bitchboy was easy. I had lots of nasty old men all lined up to fuck your tight sissy fag ass and mouth for money, but your family up and moved and I had to pay the money back with interest."

"Y... you mean..." I shuddered at the thought, "you mean you were going to turn me into a whore?"

"Oh no Kevin, you were already my sissy bitch whore, I was just going to start making some serious money of your mouth and ass."

"But... but you couldn't," I protested, "I would have told!"

"No you wouldn't, not unless you wanted your parents and friend to see the photo I took of you, all dressed up and sucking cock." I dropped my head, unable to answer for a moment. He was right. I would have done anything for him rather than my family and friends seeing photos of me like that.

"Please Derrick..." I said. My last sobbing plea for him to stop.

"Oh no bitch, you've got a debt to settle and I mean to collect."

"Please no!"

"Yeah. I arranged for someone to clean out that shitty apartment of yours and dump all that crap you call furniture. Your clothes go to Goodwill and probably some of the other junk." All I could do was sob and shake my head. "That piece of crap car you drive is already on its way to the junk yard for scrap and I phone your Boss and told him you'd quite and that he could take his shitty job and shove it up his ass."

"Oh god!" He was stripping me of everything. "But... but what about me?"

"You? Why you are going to stay here a while and earn me some money. The owner of this place is a friend of mine and owes me big time."

"Earn you money?" My mind refused to think what he was talking about.

"Yeah, you're going to be turned trick like a proper little whore from now on, and your first 'john' is already on his way up. I figure you will earn me about a grand or better a week fucking and sucking cock the way you do."

"Oh god no!" Picking up the ball gag, Derrick walk towards me.

"Open your mouth bitch." Not that I had much choice no matter how much I struggled he forced my mouth open and stuffed the gag between my teeth. All I could do was look up at him with pleading eyes, futilely begging him to release me. There was a knock at the door then, and when Derrick opened it two big black guys walked in. I moaned around the gag. Just looking at them made me shudder.

Category: Transsexuals & Crossdressers Stories