Black Man's Sissy Boy free porn video

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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 k**. 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 a****ls. 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, k**?" 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 a****l.

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?"

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Bruce gets used like a true sissy boy

This time I have decided to go ahead and domme one of you !!! Bruce is the lucky sissy boy today . He wants to know that he is only good to clean up my used cunt after being fucked by my real lovers. So, I arrange to be gang banged and have Bruce there to fluff then clean me. First off is Cameron .. he knows how to fuck me well and he wants to show you how to fuck a woman right. Cameron starts out with many hot kisses and his hands go everywhere touching and feeling me. He pulls my top and bra...

4 years ago
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2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

3 years ago
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Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

1 year ago
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Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

2 years ago
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Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

2 years ago
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The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

3 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

4 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

2 years ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

2 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

3 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

3 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

2 years ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

1 year ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

1 year ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

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