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Lori had James who had been her sissy boy for a long time. She loved to dress him like a girl and get him a date or a hook up with another gay guy. Tonight she stripped him naked and bent him over and used her thick strap on in his ass. Even though he was a sissy he had a great body. He had a nine inch thick cock and a great ass that he loved fucked. Lori fucked his ass hard as she jerked his cock and waited for him to cum in her hand so she could feed it to him. Then she pulled the cock from his ass and let him suck and lick it. Then she pulled her panties down and pushed his face in her cunt and told him to lick her. He was a good pussy licker and then when he had her cumming fast she told him to stick his tongue in her cunt and fuck her and clean her cunt real good. He had a nice long tongue that Lori loved. She could feel his tongue deep in her hole as he sucked and licked her tender cunt.

After he did a good job on her cunt she stood him up and got him ready for the night. She sat him naked and covered his face with cheap slut make-up. She put heavy black eye liner on him and bright rosy cheeks and bright red lipstick that she smeared around his lips. Then she stood him and put a huge padded bra on him. She grabbed his cock and taped it to his stomach and then put silk panties on him. Next she put a tight knit dress on him that clung to his huge tits. He now looked like a freaky slut cross dresser. She kept his body shaved with no hair on it any where and slipped his feet in six inch heels. She knew just where she was taking him to find him a gay male. Sixth Avenue had a lot of them hanging out and she wanted to fix him up with a couple of them tonight.

She took him in the back of the limo and the driver knew where to go. As he drove down Sixth Lori looked the guys over till she found the right one. The limo stopped and she rolled down the window and asked him if he needed some free ass. He sure did and she opened the door and let him in next to James. She then told James to get on his hands and knees and as he did she pulled down his panties and bared his ass. She pointed to the man and told him to strip and that James was his to do as he pleased but he needed to start by licking James in his ass before he fucked that tight hole. The man got naked fast and got behind James and spread his ass cheeks and ran a finger all around his hole. He then began to lick James's asshole and suck on his pucker. He had his tongue in James fucking him as James moaned. Lori watched the other man as his cock got hard as he worked James's ass over with his tongue and fingers. She liked that he had a nice thick cock as James loved a big rod in his ass.

The guy was licking and sucking James in the ass and then he grabbed his balls and squeezed them. Lori then reached over and took the tape from James's big cock and let it hand loose for the guy. As the guy tongue fucked James in the ass he stroked his cock and balls. The man now had a big hard cock and he then got behind James and aimed his cock for James tight ass that was wet as the guy had licked it real good. He began to push his cock in James and Lori watched as the ass got stretched wide and the guy pushed harder and entered James all the way and began to fuck him hard. As the guy fucked James Lori lifted her dress and pulled James face to her pussy and James began to eat her as he got his ass fucked hard. James sucked Lori's clit and then pushed that long tongue into her cunt and really tongue fucked her. The man cock fucked James in his ass for a long time with the long thick cock before he filled his ass with cum. Lori then moved and pulled her dress down and told James to lick the cock that had been in his ass and clean it. As James licked the guy's cock the guy began to fuck his mouth and ram the cock deep in his throat. Lori loved to watch James suck cock. She loved when the other guy had a big thick cock as it would go down the throat of James.

James's cock was now hard and throbbing and he needed to fuck to release the pressure. Lori told the naked man to get on his hands and knees and she shoved James behind him and James slid his nine inches into the bowels of the street man and fucked him like a maniac. The man was moaning and his ass was stretched wide as James fucked him hard. James showed the man no mercy and fucked him ripping into his ass as he screamed. Sometimes Lori and the limo driver had to hold the street men down as James rammed his huge cock deep in their ass but this guy stood the pain and let James fuck him hard. James then filled him with cum and pulled his cock out. Then James began to lick and suck his ass cleaning the cum from him. His ass was gaping and welcomed the long tongue from James.

Then Lori pulled down her panties again and got on her hands and knees as James shoved the street man's face into her ass and told him to lick and tongue fuck her. As the man licked and tongued Lori in the ass James took two fingers and fucked Lori in her pussy. Lori was covering James's fingers with her white cream as he fucked her hard. She loved the strange tongue in her ass as James finger fucked her cunt. She made the two guys play with her ass and cunt for over an hour then she told the street man to dress and as he got out of the limo she gave him fifty dollars. He told them any time they wanted more he was always around this corner. Lori thought he may get more as she liked that he had a big thick cock for James.

They rode around more in the limo and picked up two more men for James then they went home when James had been well fucked and sucked. When they got home Lori had James walk for her showing his big fake tits in the tight knit fabric. She then took him in front of the computer and put him live on the website for men that liked sissy boys. She had him show off his big tits and the guys began writing what a slut he was. She then pulled up his skirt and pulled down his panties and showed his huge cock. This made the men go even wilder. Not many sissies were hung like James. His big thick cock also had a huge head on it. When he shoved it in an ass they could feel the size and got a hard fuck. He also had nice big balls that the men also loved. Lori then had James play with himself as the gay men watched. He stroked his cock and grabbed his balls and even put a finger in his ass for the camera. He stroked his cock a long time before he was ready to cum then as he got close he really began to jerk off and soon had the cum squirting in the air. Lori then bent him over and spread his ass and shoved a plug in it. She showed the huge plug to the men watching and then took her time shoving it all the way in to James's ass. She pulled it out a couple times and shoved it back in till it was all the way inside his bowels. Then she got her paddle and began to spank James for the camera. She had his legs spread so his cock and balls hung down as she spanked his white ass. She gave him twenty whacks then milked on his cock and balls then got out her belt.

She gave James twenty more whacks as his white ass began to turn red. Then she reached down and milked on his cock and balls more. By now his cock was rock hard and no longer hung down but his balls dangled. She stood him and had him face the camera as she grabbed a piece of pink ribbon and tied it around his cock with a big bow. She did the same to his balls. Then she began to rub the slit on his cock so the men watching could see her finger go over the slit as she rubbed. She grabbed a metal cock plug and pushed it in the slit of his cock. She pushed it in and out several times as cum leaked out on the cock plug getting it coated. She next traded the cock plug for a longer one and then shoved it down his piss slit. She had it all the way in his cock and then she began stroking the cock with the cock plug in it. She put a finger over the tip of the cock plug to hold in in his piss slit as she now began to stroke him tighter and harder and faster. James was breathing hard and his cock was getting harder as she jerked him pushing the cock plug into his piss hole. Then just as she felt him begin to cum she took her finger off the tip of the piss hole and watched the plug shoot out of him with the big load of cum.

She knew the men loved to see the piss hole get reamed and she rubbed the slit now that the plug was out. She then got the other cock plug which was shorter but had a cap on it and when she shoved it in his hole she could fasten the cap to keep it there. Now that she had the plug in his pisser she then slipped on her strap on. She pulled James to it and had him suck the big rubber cock. As he sucked it she would grab his head and pull the cock all they way in his mouth and hold it there as he almost gagged. Then she would let him go and fuck his mouth before she pushed it in deep again and held him. She wanted the camera to see what a good cock sucker James was. He could take a nine inch cock easy. One night she got him a big black guy that was hung and had the biggest thick cock and he sucked it real good before he got his ass fucked with it. She let James suck the rubber cock for a while then she turned him and bent him over and pulled out his butt plug and shoved it in his mouth and rammed the rubber cock all the way in his ass and fucked him hard. She was pounding his ass with the big rubber cock as he sucked on the butt plug. She fucked his ass for over forty minutes before she pulled it out and rammed the butt plug back in. Then she showed James with the plug in his ass and the cock plug in his piss hole before she turned off the camera and removed the clothes from James.

She then took his naked body to her bed. He slept with her every night in case she needed him to fuck her or lick her cunt. She laid him on his back and then she got naked and sat on his face and rubbed her pussy all over him. She grabbed is head and held it tight to her pussy as he sucked and licked and then pushed his tongue in her cunt and fucked her. She took one of his hands and placed it on her ass and he knew to finger fuck her as he ate her cunt. She rode his face for the next hour as she covered him with her cream. She loved her sissy as he was the best entertainment she had. Tomorrow night she had plans to take him to the gay bar and let the men there fuck him all they wanted. She loved to see the cocks fuck his ass and fill him with cum. He always looked like a freak with those huge tits in a tight sweater but his big thick cock got the guys attention. She loved to see one guys sucking the cock as the other guy was fucking his ass. He was the perfect little sissy slut.

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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

1 year ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

1 year ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - 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 Jamie, ...

1 year ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
1 year ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

3 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

3 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

2 years ago
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Sissy Fantasy

I waited for what seemed like hours and was probably minutes when I heard Masters voice. "Silly me I forgot to open it, better hurry sissy I don't think Jenny would be too pleased if the neighbors saw you dressed that way," he smirked. The car lights flashed and the boot unlocked. I grabbed the cases and hurried inside. As I was passing Master he handed me a package. "A present from Jenny....put it on when you change... and put my case somewhere safe but don't open it," he...

2 years ago
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Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine 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 Gets A Black Master

Sissy Gets A Black Master I got up wearily from my long and exhausting night being fucked and punished by my new Black Master. As I awoke, I could scarcely believe that all those depraved things had happened to me. One minute I had been merely exchanging emails with a man, who could have been anywhere and the next minute, that very man was at my door, in my home, and then inside my body. Black Master, a man whose name I didn't even know, a man who looked to be about ten years my junior, had...

1 year ago
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Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

3 years ago
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Sissy Stepson Part 6 Carolines Sissification

Part 6 - Caroline's Sissification Mrs. Monet was now going to really put the spurs to her sissy stepson and force him to live a life of sissified faggot. With Carl still lying on the floor with sissy cream stains all over his pantyhose and panties she began taking pictures of sissy stepson. "What are you doing, I want to change," said Carl. "Oh, no just because you popped your cookies doesn't mean its over, you pathetic faggot. I now have evidence what a pervert you are and I...

2 years ago
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Sissy Therapy

Sissy Therapy by Kate "Great practice, guys! If we keep working hard, we have a real shot at the conference title," Coach Jones addressed the thirty or so high school boys gathered around him. The boys were sweaty and tired, but the coach's praise momentarily raised their spirits. "Smith nice passing out there. Keep up the good work." Fifteen year old Billy Smith grinned cockily. "Sure, Coach. After all, I am the greatest!" The other boys moaned at Billy's arrogance. Coach...

3 years ago
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Sissy Stepson 8 Carolines Milking

Part 8 - Milking Caroline "Our sissy is going to get ready for milking, I have enough knee highs for everyone to participate" said Mrs. Monet excitedly. She gave everyone three knee high's, sissy Caroline was going to get the milking of her life! Caroline came back to the group with here outfit on and was instructed to sit next to Regina for milking. Regina encased the Caroline's sissy stick with the nylon and instead of using her hand. She took off her high heel and stuck the toe...

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