Pretty Blonde Sissy free porn video

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Naked and young - in bed with a big black MAN! Both of our naked bodies entangled together. I learned to give blowjobs early.

I started masturbating when I was very young. Once I started doing it, it was all I thought about, 27/7 it seemed like. At that time I was living with my mom and her boyfriend Micheal. I never knew my real dad, Mom never talked about him; 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. She met Micheal when I was ten, and he moved in soon after.

Micheal was Mom’s first black man. She met him in a bar. He had recently been released from state prison, and 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 ok when Mom was around, but when we were alone he mostly ignored me. I think it was because I wasn’t a very masculine 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 young old son could kick my ass.

By the time I was young I was jerking off several times a day. I used to go in Micheal's and Mom’s bedroom and sneak Micheal's’ fuck mags to masturbate to, while looking at the sexy nude women. Sometimes I’d pop in one of the porno videos that Micheal had, and jerk off while watching the beautiful white women making love to - servicing - their gorgeous black men. Around this time I got into going into mom’s bedroom and going through her lingerie drawers. One afternoon I found some lipsticks in the drawer and on impulse applied some to my mouth. I looked in the mirror and was shocked; I saw a sexy woman staring back at me! I stepped into a pair of mom’s high heels and almost came right then and there. With my shoulder length blond hair I literally looked like a woman. From then on I jerked off in heels and lipstick.

One afternoon when Mom was at work and Micheal was out I put on some black spike high heels and applied some sexy red lipstick on my pouty lips. I was admiring my image in the full-length mirror when I gasped: Micheal was standing behind me with his arms folded, watching me. I grabbed for Mom’s Frederick’s of Hollywood silk shorty robe, but his hand lashed out and grabbed the robe from my hand. He gave a long low whistle. "Like mother, like son”, he said.

“Micheal, I was just – “

“Naw, it’s cool, Keven,” he said. “You lookin’ fine as fuck, girl. Turn around, honey.”

I did like he said and he whistled again. “Girl you got some pretty laigs on you – just like yo momma – prettier even.” He reached over and ran his hand up and down my bare legs. “Fuck! Soft as silk an’ sweet as sugah! Ain't hair ONE on that fine young ass!”

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

OHMIGOD! I was SO hungry for love and affection! I never had a Daddy before! 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 t-shirt and kicked off his jeans. I almost shit when I saw the size of the bulge in his jockey shorts. He came close. “Feel of it, Keven,” he said. “Go haid, 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 Micheal'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. Micheal was a good teacher. He told me how to suck cock and balls. I sucked his cock until he said, “I’ma 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 nut tasted SO sweet!

After that I became Micheal’s woman, having sex with 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 banged me until I was maddened with sex desire and I begged for his cock in my ass. He kept telling me no, and I kept begging him to fuck me.

He laid me back and had me raise my 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 Micheal’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 into 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 Micheal 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, Keven!” Micheal 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. Micheal 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, Micheal?” I whimpered, my bare white skinny legs up over his big black forearms as he fucked me.

“You ARE a woman, Keven”, Micheal whispered 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 Micheal's big chest and he wrapped his arms my head full of stars, smelling his flesh, and soon I slept, too.

Eight months later Micheal violated parole and was sent back to prison. After he was gone, Mom was cleaning out his stuff and she found a videotape of Micheal and I 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, I was young and 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 – 200 bucks that Micheal 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 there were very few 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,” he asked me?

“I’m 18,” I lied, which, looking back on it must have seemed very funny to him because I looked much younger

“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 bare 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 smelt 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. I was crazy horny! I couldn't get sex out of my mind. It was like some, I don't know, some -DEVIL - was in my head! Nowadays when I jerked off, in addition to the fuck magazines, I thought of when Micheal 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 confused. “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 k** 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,” he said, licking his lips 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, bitch, 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 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 opened it but there was a heavy metal screen bolted to the outside. The street seemed a very long way down, even if I could get the window open it was too high to jump. I saw some people on the street and I yelled to them for help. A few of them looked up, but kept on walking. I realized that no one cared. 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-WEEE! 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. The clerk opened the door and looked at me, cowering on the bed, naked and scared. He shook his head. “Good luck, girl,” 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 tank top. 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 at the big, calloused 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 topknot. His other hand was feeling his groin. He took my topknot 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 blowjob – at worst a fuck – I had done it all before, with Micheal. 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 Micheal’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 outchyo haid.”

He stripped off his tank top 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 Micheal. As I blew him I ran my small hands all over his big muscley legs – men like that – I had learned that from pleasing Micheal. 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. “You definitely gots some skills” 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 hoe. You gone pay my money back an then some.”

Then he reached into his back pocket 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. I was a black man's whore.

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 Lord Satan 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 double. 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 ass whippin' just like this. Are we clear?"

I nodded, blubbering - "I-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 sniveled meekly, cowering on the bed, small and naked under this big brutal black 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 blowjob 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. He was wearing sweat shorts and a sweatshirt 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 bad, 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 anus.

It hurt as the head ripped in past the tight ring of sphincter muscles, and I tensed and cried out - "Aiiii, Papi!" - this made him crazy horny and he began fucking me hard - like an a****l. 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 a****ls 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. I was positively glowing!

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

"And a 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 handcuffed nude white punk - who'd obviously had a beating - 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 ice cold and 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' that 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. "Keven", I answered in a low voice. I felt Odell's grip on my arm tighten.

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

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' Finesse'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 short shorts so brief the cheeks of my buttocks were exposed, 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 so young, but in drag I looked easily like a 20-year-old woman. We got into a beat up old Cadillac 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 I’ma go?" I asked him.

"You gone get you ass out on the stroll and hustle you ass, that's what you gone 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 or in alleys behind dumpsters, giving everything I made to my man!

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The Farm School Sissy

INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much...

2 years ago
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Becoming a Sissy

Previously published, but in separate parts, this one is the whole story start to finish.This is the story about how I went from being an inadequate husband to being a porn addicted goon and finally in the past year fulfilling my sissy ambition to worship a big cock and balls. They belong to my best friend Tom who I have known for 20 years. It was a journey that took a few years but if I had been brave enough when I was younger would have taken no time at all and spared me lots of humiliation...

3 years ago
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What is a Sissy

I am often asked what makes a sissy. In my experience you cannot make a sissy. A sissy is born that way, it is like saying how do you make a homosexual or a lesbian, I truly believe that sissy is a form of sexuality. Over the past 20 years I have met many "sissys", they have run the full gauntlet from those who think wearing pink frilly panties makes them a sissy to those whose whole existence is consumed by thoughts and actions of sissyfiaction. In the latter group many are middle aged men...

2 years ago
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I would be the Young Sissy

My 21st birthday...my first day as a man, as a true lord of the Manor...myfirst day as a Master. I was so nervous I threw up my lunch. Not verymanly, I know, but just the thought of having my very own sissy to playwith had me teetering between the giddy excitement of a k** right about toopen the biggest present under the tree, and the stark terror of officiallybeing a man in my step-father's eyes...how could I measure up to him? Ifelt destined to disappoint him...and I didn't even know why I...

3 years ago
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I Want To Be A Sissy

He Wanted To Be A Sissy The Lincoln town car drove slowly up the long driveway and halted at the entrance to the two-story building. It was late morning on a warm sunny day. The chauffeur jumped out and opened the rear passenger door. A lady dressed elegantly in a mauve skirt, white blouse and matching jacket swung her feet out and stood up. She looked at the other person in the car. "Well we're here now. Seems like a beautiful place. So step out carefully." The other person...

2 years ago
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My sisters their friends and me their sissy

Part One My oldest sister Vickie, was 18 when my mom died. My middle sister Michelle, was 14 and my youngest sister Joy, was 11. I, Mark was the baby of the family at 7 and had been the only male in the house since father had passed away when I was 2. He left us well off and with his money well invested we lived very nicely indeed. We had a private tutor/governess, Ms Wells, a young lady of some thirty or so I suppose. A live-in housekeeper Ms Dee Dee, a French exchange student...

4 years ago
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Young Sissy

Young Sissybysmittysimon©Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series.I don't know how long I was under days, weeks who knows, maybe even months. Reality blurred with nightmares as I felt my flesh being cut into by cold scalpels and stuck...

4 years ago
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Rules for sissy

General Behavior Sissy is expected to always obey these rules. * Sissy will never masturbate or in anyway contribute to her having an orgasm without Mistress' permission. * Sissy will report immediately any orgasm that occurs without permission. * Sissy will accept whatever punishment Mistress decides appropriate. (Punishment for orgasms out of chastity will be more severe than for those within the cage). * Sissy will not put any part of her Mistress' sissy in jeopardy of ...

3 years ago
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Raised a Sissy

Raised a Sissy Alessandra Durante I've been a sissy my whole life. I didn't know that when I was child, but that what I was raised and reared to be. I never had a choice in the matter. I was born into a wealthy family, but I never knew the privileges of wealth. My mother was a strong willed woman who ran our countryside home like a queen. My sissy father was her faithful and humble servant. My father doted on her and obeyed her every command as if he had no choice. My...

2 years ago
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Curiosity Spanked the Sissy

You had driven all night to get to where you were and as you look at the house you wonder why? You just cannot understand why you are outside the house of Mistress Penny. Is it curiosity you wonder, certainly she is a completely different Mistress from your own goddess, Mistress Michele. She is the Mistress to your good friend on Fetlife, Sissy Davina but the only thing you know about her is how she has been described by Davina. You know she is curvy Mistress unlike Mistress Michele, is...

2 years ago
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Tweak Chapter Three Birth of a Sissy

Melissa's mentoring of Simonne continues at an ever-increasing pace. He quickly learns that submitting to Melissa's demands may be the only way of convincing his girlfriend to submit to his. Operation Linda begins in earnest. 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 Three - Birth of a...

3 years ago
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Beth and Sissy

Beth and Sissy Copyright CassandraToday 2016 Beth stood up and walked from the bed to the far side of the room, over to the ... what is it? thought Sissy; it looks like a St Andrew's Cross lying on its back, with supports underneath to hold it at tabletop height. Beth turned, smiled at Sissy, and crooked her finger in an unmistakeable "come here" gesture. So enthusiastic at first, Sissy was now hesitant, as it sank in that this would be reality, not fantasy. She rose and started...

2 years ago
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The Making of a Sissy

She had known from a very early age that she was not like the other boys; her mother had passed her on to her strict aunt Jane at a very early age, and she had never known her father.  Jane’s strict regime of making the boy dress in girls clothes at all times when at home only furthered the yearning to be a girl which was already firmly within the soon to be a sissy’s mind.  Jane’s girls took special delight in dressing their sissy brother and loved to take him out to the mall and such places,...

2 years ago
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Andrew the Unsuspecting Sissy

ANDREW'S INTRODUCTION Audrey was alone in her study. Up on the 60 inch, big screen was a security camera that flashed from locations all across the manor. Audrey locked in location six and location eleven. She then pressed a button and stood up and removed her blood red silk blouse and unclasped her long black tweed skirt and lowered the zipper and watched as the skirt puddled at her feet. Carelessly she stepped away and adjusted her hose and garter belt. She was braless and wore no...

4 years ago
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Sunday Night Football Sissy

Sunday Night Football Sissy It's no surprise that we love football here in Texas. We all head out to watch high school ball on Friday nights, and of course we love to cheer on our college boys on Saturdays. And the grown men dominate our Sundays. Especially if you're a sissy slut like me. I am a sissy cock slut who happily serves a small group of men here in town, and things took an interesting turn a few years back when I learned that Master David was an avid Cowboys fan, while...

2 years ago
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Teaching the Sissy Maid Workshop at the MVP Chapter Three Daisy Begins Her New Life as a Sissy

Teaching the Sissy Maid Workshop at the MVP, Chapter Three Daisy Begins Her New Life as a Sissy Maid She took and held three enema bags before I allowed her to get out of the tub and she was emotionally, sexually, mentally, and physically broken. Not permanently, that takes years to accomplish, but she had given up and began the process of accepting that she was powerless and too weak to resist me. To keep her in the right frame of mind, I grabbed her by her hair and walked her...

2 years ago
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A Happy Sissy

A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results....

2 years ago
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The Blushing Sissy

The Blushing Sissy by StateRowdy [email protected] ? She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties down...

3 years ago
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Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

2 years ago
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How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

4 years ago
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Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

4 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

4 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

2 years ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

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