#496 - Sissy Story 5 - Black Man's White Sissy

After the good exptirience on August
I would like to continue the Sissy Story sunday collection! why not?!?
for our weekly appointment an interesting tail about first time and abusing!
enjoy the Sissy story number 5!

Anna Malice

PS if english is not your own language try to translate the page by google language tools
inserting the address of this page!


Black Man's White Sissy

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince myself that I was normal, of course, in retrospect it is obvious that I was identifying with the women.

One day when my mom was at work, I was laying in her bed, masturbating. I got up and rummaged through her underwear drawer. The drawer smelled like perfume and the odor made my dick stiffen. Some of her panties had stains - I think they were cum stains - on the crotch. Anyway, I don't know why, but something prompted me to try on a pair of her silky nylon hose. The material felt so good on my legs! Next I stepped into a pair of her red french cut panties. Then I caught a glimpse of myself in the full-length mirror - and was electrified.

I was about 5', 2" then, and the only body hair I had was on my 18 year old pubes. I just couldn't believe how much like a girl I looked! I quickly applied som of my mom's hot red lipstick and checked myself out; I almost came in Mom's panties right there.I looked every bit as sexy as those bitches in the fuck mags. I jerked off until my 18 year old dick was sore.

I never knew my real dad; Mom never talked about him, and once, when she was drunk, she told me she wasn't even sure who he was.Mom always had boyfriends as far back as I can remember. Three or four of them lived with us at different times, but they never stayed for long. Then She met Butch, and he moved in soon after.

Butch was Mom's first black man. He had recently been released from state prison, but Mom was crazy about him. I used to listen to them fucking every night. She was always hanging on him, treating him like he was a king, massaging him, kissing on him. He didn't like me much. He treated me nice when Mom was around, but when we were alone he mostly ignored me. I think it was because I wasn't the most masculine 18 year old kid. In fact, looking back on it, I was a downright sissy. I loathed athletic sports, and was frail and a weakling. Once he told me that his 7 year old son could kick my ass! And me, an 18 year old!

Anyway, as I said earlier, my favorite pasttime was jerking off several times a day. I used to go in Mom's room and sneak Butch's fuck mags and masturbate while looking at the sexy nude women. Sometimes I'd pop in one of the porno videos that Butch had, and jerk off while watching the beautiful white women making love to their black men.



One rainy afternoon when Mom was at work and Butch was out I put on some black spike high heels and applied some sexy red lipstick on my pouty lips. I was standing in front of the mirror, admiring my feminine beauty and stroking my cock when I was startled by a wolf whistle. I gasped; there was Butch standing behind me with his arms folded, watching me. I grabbed for Mom's Frederick's of Hollywood silk shorty robe, but Butch's hand lashed out and grabbed the robe from my hand. He whistled. "Like mother, like son", he said.

"Butch, I was just – " I noticed his hand was squeezing his groin; that's when I felt fear. He had me in his grip, his big hand squeezing my upper arm tightly. I was completely nude, except for the 4 inch high heels. He was wearing a pair of atheletic shorts and a sweatshirt with the sleeves cut off. Butch was really buff, and he loved showing off his muscles.

He relaxed the grip on my arm and I went for the robe again.

"Uh, uh, uh", he said. "You just stand right there.

His eyes darted to the tv. The porno tape was playing. On the screen a blonde girl was on her knees in front of a black guy and she was giving him a blow job. Butch stripped off his sweat shirt. He was about 5', 10"; 190 lbs, and all muscles. He had tattoos all over. He went over and flopped on the bed, still rubbing his groin. "Oooh, FUCK!" he said. "Man, she could suck the chrome off a bumper hitch! She is fuckin HOT!" He looked at me. "Hey, Stevie," he said. "You lookin pretty sexy, too...pretty as you mama - prettier, even. What are you now 18 - 19? Turn around, girl, lemme look at you."

I did like he said and he whistled again. "Girl you got some pretty laigs on you – just like yo momma. He reached over and ran his hand up and down my bare legs. "Fuck! Soft as silk an' sweet as sugah!"

He pulled me close and bent his head to mine – and we kissed, his hungry mouth clamping over mine, his tongue snaking into my 18 year old mouth and down my throat.

OHMIGOD! I was SO hungry for love and affection! After all, I was 18!I responded to his kiss and my tongue was wrapped around his as his big arms encircled me and I felt SO safe, and SO secure. Suddenly he picked me up and carried me to the bed, lowering me gently onto the sheets.

I watched as he stripped off his sweatshirt and kicked off his shorts. I almost shit when I saw the size of the bulge in his jockey shorts. He came close. "Feel of it, Stevie," he said. "Go haid, girl, squeeze on it."

I reached up and felt the hard boner under the material of his shorts. He groaned in pleasure. "Take my shots down, sissy," he said.

I hooked my fingers and thumbs under the waistband and pulled his shorts down – and gasped as his huge black cock sprang free. OmiGOD! What a big cock!

"You like that cock, baby?" he asked me. "Go haid, girl, feel of it."

I squeezed down around his thick black cock and I saw a big pearly bead of semen form on the purple head. I knew about sucking cock because I had watched a lot of Butch's porn tapes. I got off the bed and knelt at his feet. I knew he wanted a blowjob, and I was flattered that he wanted me to give him one. I flickered my tongue out lapping up the bead of cum. Mmmm! My first taste of semen! And it was SO good!

So, soon after getting my first kiss, I was giving my first blowjob. And here I was, over 18! Butch was a good teacher. He told me how to suck cock and balls. I sucked his cock until he said, "I'm gonna cum – open yo fuckin' mouth!"

I opened my mouth wide, just like the ladies in the porno tapes and waited as he masturbated over my mouth. Sudden he groaned in pleasure and ejaculated into my mouth. Fuck! His cum tasted SO sweet!

After that I became Butch's woman, fucking him behind my mom's back. Actually our first fuck came 2 days after the first blowjob. We were in the bed nude and we were making out and I begged him to fuck me in the ass. As we kissed he greased his finger in Vaseline and inserted it into my rectum. When I was comfortable with that he inserted a second finger. We kissed and he finger fucked me until I was maddened with sex desire and I begged for his cock in my ass. He kept telling me no, that he was too big for me, and I kept begging him to fuck me.

He laid me back and had me raise my 18 year old legs. He placed my heels over his broad shoulders. This position automatically had the effect of spreading my buttocks and immobilizing me, because my back was on the pillows up against the headboard.

I could feel the head of Butch's cock near my anus as he bent to kiss my mouth and neck and tits. I was squirming, wanting – needing – his dick inside of me. Then he began to push his cock to the mouth of my hungry anus. OH! FUCK! IT FUCKIN' HURTS!

I tried to squirm away but there was nowhere to move. I was lucky if I weighed 70 pounds, and Butch had his 250 pounds of big black muscles on top of me. I was completely helpless as his cock tore into my clenched sphincter muscles. I screamed in pain and naked fear. "Shut up, Stevie!" Butch barked. Then more gently, "Relax, relax you ass, baby."

I tried to do as he said and sure enough, the greasy cock suddenly eased deep into my fuck hole, and the pain subsided. Butch began fucking me with long slow strokes – all the way in – all the way out. He was kissing my neck and sucking on my tits and I felt SO feminine and sexy! Here I was, completely nude, lipstick on my mouth, high heels on my feet, being fucked by a handsome black muscleman! Not just fucked, but made LOVE to!

"Am I like a woman, Butch?" I whimpered, my bare skinny legs up over his big arms as he fucked me.

"You ARE a woman, Stevie", Butch said in my ear. "You MY woman – ALL woman, baby."

We were mating like sex mad animals. Suddenly I felt his body tense and he began shaking. His deep bass voice was groaning and he plunged in balls deep – and I felt his hard on jumping inside of me as he released his semen flooding my bowels. He relaxed and lowered my legs from his arms and fell on top of me, breathing heavily. We kissed and I could feel his cock softening inside of me. He eased it out and it felt like I was taking a big greasy constipated shit. I cuddled up against Butch's big chest and he wrapped his arms around me and he went right to sleep. I lay there, naked in his arms, my head full of stars, smelling his flesh, and soon I slept, too.

Eight months later Butch violated parole and was sent back to prison. After Butch was gone, Mom was cleaning out his stuff and she found a videotape of me and him having sex. I have never seen her so pissed off. She bought me a bus ticket to my grandparents and dropped me off at the station. Well, being over 18 and rebellious, I had no desire to go live with them because they were religious nuts and very strict.

I traded my ticket in at the counter for a ticket to Dallas. I don't know why I chose Dallas, God knows I didn't know anyone there, I just wanted to get as far away as I could from Mom and my grandparents. In my bag I had stashed away a couple of pairs of high heels and some lipstick. I also had – in addition to the hundred bucks Mom had given me – 800 bucks that Butch had hidden from Mom.

The bus pulled into Dallas in the late afternoon. It was June and really hot. I wandered around the city for hours with no idea where I was going. Eventually I found myself in what I was later to learn was a ghetto. Being from a small town I knew next to nothing about the world. I went into a store and bought a couple of fuck magazines. Everyone I saw around me was black or latino – which was strange to me because, other than Butch, there were no black people in the town I had spent my life in.

After leaving the store I walked a couple of blocks. I spotted a decrepit looking building with a flashing neon sign in front that said "Hotel Dallas". It was getting dark. I went into the lobby. I passed some worn out looking furniture where some bums were sleeping and went to the desk. The clerk was an older latino guy who seemed surprised to see me. I guess I didn't realize how out of place my youthfulness and skin color made me. I asked him how much for a room.

"How old are you, kid?" he asked me.

"I'm 25," I answered him, which, looking back on it must have seemed very funny to him because I was lucky if I looked 18 - which I was.

"Forty bucks," he said, pushing the register toward me. "Sign there," he said.

I signed a made up name and gave him the money. He handed me a key. "Room 402 – take the elevator," he said.

The elevator was really old and it had a folding cage like door that you had to close first, then the big door closed when you pushed the floor number button. It took a long time for the elevator to get to the fourth floor. I stepped out into the hallway. The lighting was really dim. I found my room and went in.

The room was surprisingly large. I flicked the light switch. A single naked light bulb filled the room with a sickly pale light. In the middle of the room against the wall was an old iron bed. The mattress was lumpy and had stains all over it. It smelled like piss. There were sheets folded on the mattress. Against another wall was a sink. There was no bathroom. That, the clerk had told me, was located down the hallway and was communal, meaning all the guests on that floor had to share it.

I threw the sheets on the bed and took off all my clothes; I couldn't wait to masturbate. Nowadays when I jerked off, in addition to the fuck magazines, I thought of when Butch and I made love. I jerked off 3 times in a row before falling to sleep, cum drying on my belly.

I don't know how long I slept but when I awoke it was still dark. What woke me was a noise. I opened my eyes and was shocked: the latino clerk was standing over my bed! I pulled the sheet over my bare body. "What do you want?" I said.

He stood there looking at me. Finally he said, "I want the money for your friend's room. They checked out and said you were paying."

I was befuddled. "What friends?" I asked. "I don't have any friends. I just got off the bus – I don't know anyone here."

A crafty smile played over his lips for a second. Little did I know it, but I had just confirmed his suspicions – a runaway 18 year old punk on his own. He reached out and began pulling the sheet off of me. I tried to pull it back but he yanked it to the floor. "You got smooth legs," he said. Then his look got hard. "One way or the other you gonna pay that bill."

I was really frightened now. "Ok," I said. "I'll pay. How much is it?"

"Six hundred bucks," he answered. My heart sunk. I knew that it was all I had, and the thought of having to give it up like that was depressing. But I realized that I had no choice.

"Can I have the sheet – to cover myself while I get you the money?"

He handed me the sheet and I wrapped it around my body. "I don't know why you want to cover up a pretty body like that, puto," he said as I went to my bag. I dug around and suddenly I felt sick. The money I had was gone. I dumped the bag out – nothing. I picked up my pants and went through the pockets. I had been robbed while I slept. "It's gone – all my money is gone – someone stole it!"

The clerk reached out and grabbed my arm in a vice like grip. "Look, bitch, don't fuck with me or I'll beat your ass so bad you'll have trouble walkin'. I want the fuckin' money you owe me – NOW!"

I started to cry. "Please," I said, "please don't hurt me! I'm telling the truth – my money is gone!"

He relaxed his grip. "Ok,if that's the way you want it." He bent down and scooped up my clothes and stripped the sheets from the bed, including the one I had wrapped around me. He headed for the door.

"Where are you going?" I asked, crying. "Can I please have my clothes back? I'll call my mom and get you the money."

He paused at the door and laughed harshly. "Your mom? Fuck that, puto, you're over 18, You gonna earn that money." He left and closed the door behind him. I heard a clicking noise. I ran to the door and tried to open it. It was locked. I began to panic. I ran to the window. It was so filthy I could barely see through the glass. I tried to open it but it only went up about 8 inches. The street seemed a very long way down, even if I could get the window open it was too high to jump. I was trapped – a prisoner.

An hour must have passed when I heard the lock and the door opened. It was the clerk. There was a big black guy with him. They entered the room, locking the door behind them. "Ooooo-EEE! You wasn't shittin', Jose!" the black guy said, staring at me. "This some sweet lookin' pussy!"

I tol' you, man," Jose said. "So, we gots a deal?"

"We gots a deal", the black man said. He took a wad of bills out of his pocket and handed it to the clerk, who took it and stuffed it into his pocket. He opened the door and looked at me, cowering on the bed, naked and scared. He shook his head. "Good luck," he said. He left, closing the door behind him.

The black guy was looking at me with a hard look. He was about 30, six foot two, at least 200 pounds and ripped. He was wearing a tanktop. He had a shave head and a goatee. His arms were bigger than my legs, and covered in tattoos. "You know how to suck cock?" He asked me. "And don' lie – I seen the lipstick an' high heels in yo bag."

I nodded. He stood there staring at me. "Stan' up," he ordered. "I wan' check you ass out - see what I done paid fo"

I got off the bed and stood in front of him naked. "Turn yo ass aroun' " he ordered. I obeyed him numbly. I tensed when I felt a big hand feeling up my bare legs. It moved to my buttocks, up my bare back, up the back of my neck and through my long blonde hair. Then he ran his fingers up through my hair, twisting it into a top knot. His other hand was feeling his groin. He took my top knot and forced me to my knees. "Unzip my pants," he said.

I was on my knees, my head kind of twisted to an angle because of the grip in my hair. I did as he told me. Oh well, what the fuck, it was only a blow job – at worst a fuck – I had done it all before, with Davis. I unbuckled and unzipped his pants. They fell to the floor. I didn't have to be told – like all black men he wanted to be served. I eased his undershirts down. He had a big cock, about 8 inches, no worse than Butch's, I thought. His dick was erect and veiny. He pushed my face to it. "I want a nice blowjob, sissy," he said. "Lots of tongue and saliva – no teeth – I feel teeth Ima knock 'em out 'yo haid."

He stripped off his tanktop and kicked his pants aside, standing there like a naked black bull. I felt my dick getting hard, too, as I ran my tongue and lips over his cock. I began sucking his dick, using all the tricks I had learned from Davis. As I blew him I ran my small hands all over his big muscley legs – men like that – I had learned that from pleasing Butch. Then I kissed his balls, sucking them into my mouth. He groaned in pleasure as I sucked his cock and balls. Suddenly he tensed and I felt my mouth flooding with sweet tasting cum. There was so much cum I had to gulp it down to prevent it from spilling out of the corners of my mouth. I swallowed it all and cleaned his penis off with my lips, nibbling and sucking the last drop out of his cock. "Didja like it, honey?" I asked him.

He grunted. He quickly dressed. "I ain't gone lie, that was one pro blowjob," he said. "Stan' up, I wanna see that pussy."

I stood up and he took me by the arm and turned me around. "Bend over and spread yo ass." He said. I obeyed and he whistled. "Yeah, nice and pink and tight," he said.

I felt better now; I had sucked him off and he had gotten his money's worth. "Can I have my clothes back now?" I asked him.

He glared at me. "You don' get it – do you? I paid 300 bucks fo you ass. You belong to me now. You my ho. You gone pay my money back an then some."

Then he reached into a back and took out a pair of handcuffs. He took my left wrist and clamped one of the cuffs on it, the other cuff onto the iron bed board. The cuffs had a length of chain connecting them that were longer than the usual length - about double. At least it gave me more movement. But there was no getting around the fact that I was chained naked to the bed; I was no better than an animal.

Beginning that night the black man - his name was Odell - brought men in to fuck me. I began to dread the click of the locks in the door because i knew it was another trick for me to service. At first i was sullen and uncooperative, but a severe ass whipping from Odell put the fear of god into me. It happened after the second trick; the guy complained that I was a dead fuck, according to Odell. He came in the room, cuffed both my hands to the sink, and started giving me a beating like I had never had before. He used his fists and a big leather belt. When he was done my right eye was completely swollen shut and my upper lip was swelled up like a duck bill. I had big purple bruises all over my body, and I ached something terrible. He cuffed me back on the bed and pinched my jaws between his big hand, his face inches from mine. "Every time I get a complaint from a trick", he said. "An' you gonna get a asswhippin' just like this. Are we clear?"

I nodded, blubbering - "i'll do anything you say" - whap! He belted me across the face with his open hand.

"Anything I say what?" He roared. "Anything I say DADDY!"

"Anything you say, daddy", I replied meekly, cowering on the bed, small and naked under this brutal man, a man to whom I now belonged.

Imagine how I felt, both physically and emotionally, when less than a half hour later, the door lock clicked and Odell let in another trick. Odell had led me to understand in no uncertain terms that I was to act feminine and seductive, and to make every blow job and fuck so that the trick left feeling like a king. So when this guy came into the room and approached the bed I smiled and said, "Hi, handsome!"

The guy was a mexican who looked like he'd done plenty of time in the joint. H was wearing sweat shorts and a sweat shirt with the arms cut off. He was about 5', 10", and built like a weight lifter. His big arms were covered with tattoos, as was his back and chest I saw when he stripped off his clothes. He was built like a bull. He had a very cruel looking face with a thin slash for a mouth - which cracked into a humorless smile - when he saw me up close. "Looks like you been misbehavin', puto", he said.

I smiled. "Yeah, I been a bad girl, so my daddy hadda beat my ass". I reached out and ran my hand over his big muscles. "Ooooh! So BIG!"

He was completely naked now and he got over me on the bed, the springs creaking loudly as he did. He kissed on my neck and tits. "Squeeze my dick, puto," he said.

I obeyed him, encircling the base of his rigid penis with my thumb and forefinger and squeezing. At the same time I felt my own dick getting hard from the feel of his hot kisses on my bare body. His mouth searched out mine and our lips clamped together and I felt his tongue snaking into my throat.

Now I was so horny! His big body moved over me and he was ravishing my neck and tits, kissing my ears and mouth. "Am I like a woman, Papi?" I asked him.

"Just like a woman, beautiful", he answered me huskily. "You are a woman - you are my woman!"

"Oh si, Papi - I am your woman!" I whimpered, reveling in the feel of his sandpaper face as it nuzzled my soft, bare flesh. I felt his fingers working into my ass and I wiggled my hips in pleasure and anticipation. "You gonna fuck me, Papi?" I whispered in his ear.

"Gonna put a baby in you", he whispered back, kissing my belly.

I almost went crazy when I heard those words; they inflamed me. "Oh, honey, yes! Put a baby in me, darling - make me pregnant - pleeeze!" I sobbed.

His big strong hands cupped my buttocks, lifting them as my legs went up over his shoulders, and he mounted me, his hard cock seeking the mouth of my hungry anus. With my free hand I reached down and grabbed his cock, guiding the head to my 18 year old anus.

It hurt as the head ripped in past the tight ring of sphinctre muscles, and I tensed and cried out. This made him crazy horny and he began fucking me hard - like an animal. He had very muscular thighs and he used these to pump his groin into my ass.

I've been fucked a lot since then, but I remember this fuck as one of the best I've ever had. His cock inside of me, his muscley arms around me, his mouth nipping and biting - I felt the way two animals must feel in some cave - mating, savage mating.

When he came inside of me he quickly dressed and knocked on the door for Odell to let him out. A few minutes later Odell entered the room, smiling.

"Now, see, that's more like it", he told me. I smiled back at him. I had just had the best fuck of my young life and it showed.

"You need to take a piss?" he asked me.

"I gotta shit, Daddy", I said.

I thought Odell was gonna give me my clothes for the trip out to the hallway bathroom, but he just cuffed my hands behind my back and took me in a vice like grip by my upper arm and walked me - completely naked - down the long hallway to the toilet. Halfway down the hall a guy came out of a room. He looked at Odell and me briefly before lowering his eyes and walking in the other direction. I wonder what he was thinking: A big black guy, pimp walking a nude white 18 year old punk - a punk who'd obviously been beaten up - down to the toilet. Well, if it bothered him he must have put it out of his mind, because no cops ever came to rescue me.

I took a shit - it was shit and cum both - and Odell stood outside with the door wide open as I defecated. When I was finished I started to come out of the bathroom, but Odell stopped me. "Get in there an' wash that pussy", he pointed at the bathtub.

Obediently I got in the tub and ran the water. It came out rusty, but I took the bar of soap and soap up my ass and ran water over it with a can someone had left there.

When I was finished Odell handcuffed me, took me by my upper arm and walked me back naked to the room. We passed a couple, a man and a woman, both intoxicated. The woman, obviously a prostitute, stopped, and looked at me from head to foot. Then she looked at Odell. "Wassup, Kendra?" Odell said.

"Same ol' shit, 'Dell", she said, staring at me. "I see you gots some new stuff". She took her hand and put it under my chin, raising my head. I felt totally humiliated. "Mmm, MMM!" She said. "She cute! You been seasonin' her, I see".

Odell chuckled. "Yeah, we had to come to a unnastandin', feel me?"

The whore laughed. "Fo' sho', I feel you fo' sho'", she laughed. What's you name, girlfriend?" she said to me.

My eyes turned to Odell. "Steven", I answered in a low voice. I felt Odell's grip on my arm tighten.

"Stevie", he corrected. "This here be Stevie. Right, Stevie?"

I hung my head. "Yes, Daddy", I said. The whore shrieked with coarse laughter.

"Daddy! Ha, ha, ha! Odell you Daddy, sweetie?" she asked. Then to Odell: "Where you keepin' her?" she asked.

"402", he said. "You know anyone lookin' fo' Stevie's type, you let me know, coo'?"

"Oh, fo' sho', she answered, grabbing her trick by the arm and leading him to a nearby room.

Odell kept me locked up for over a month. During that time I had sex with the men he brought to the room , often as many as 20 or more a day. I never knew when, he'd just show up with the trick - could be any time day or night. Most of them were black or latino street types, but occasionally they would be well dressed white men, usually in their 50's or 60's. One told me that he was a judge. But after he fucked me he never offered to help me. I gradually got used to the idea that I belonged to Odell. Sometimes he was very kind and even loving to me. Some nights we would lie in bed together after making love - just like a husband and wife - and the fact is, I fell deeply in love with him and would do anything for him.

That's when he put me out in the street. One day he came to the room and handed me some tight minidresses and high heels. He had lipstick, eye shadow, mascara, and hairspray. When I was all dolled up he took me out of the hotel for the first time in almost 2 months. I was male but in drag I looked easily like a 20 year old woman. We got into a beat up old Caddilac and he drove across town to an area with a lot of bars and clubs. He pulled over near a liquor store. "Get out," he said.

I looked at him. "Where am I gonna go?" I asked him.

"You gonna get you ass out on the stroll and hustle you 18 year old ass, that's what you gonna do!" he said.

So there it was - I was a street ho now - hustling to give blow jobs in the back seats of men's cars, in alley ways, behind dumpsters.