Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Arabian Nights Pt. 01

by MicheleNylons on Sep 26, 2017
Transsexuals & Crossdressers

Michele felt the huge member buried in her anus begin to pulsate; hot, creamy semen flooded her back passage. She was lying face down on the huge bed; pressed down into the satin sheets and soft mattress, her own penis trapped in her satin panties was also hard and leaking pre-seminal fluid. She lay still as Ahmed, the man lying on top of her, emptied himsel...

Guildmates Ch. 02

by TGDIB on Jun 15, 2020
Transgender & Crossdressers

(What is this, a crossover episode? Sorry for the delay and any lacking quality, been super busy. Thanks everyone for reading After the compelling argument Damon had made the night prior, Asa decided to indulge him and give things a shot. At the very least, the sizeable sum he had been provided was enough to keep him going for a while. He called into work,...

The Chronicles of Miss-chief

by vanillathunder on Feb 21, 2020
Transsexual

These are just some prompts to get started, feel free to add threads for new ones! Salon-the-Job Training: When a young man gets a job sweeping up at a salon, his co-workers decide to teach him about the various treatments they do there. Spell-ing Error: Two friends get more than they bargained for when they try to conjure up a woman with a stolen spell book...

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Healslut Adventures

by agenteightysix on Jun 22, 2020
Fantasy

"And don't come back!" That's the last you hear before you're kicked out into the street and a door is slammed behind you. This isn't the first time you've been kicked out of an inn, but it is the first time you have been thrown out into the street in the middle of the day stark naked, your belongings kept by the proprietor to pay your debt. You bl...

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A solution

by Seahawker on Apr 3, 2020
BDSM

Hello my name is Mark. I'm a 35 year old marketing accountant with my father's advertising agency. My wonderful wife, Stacy also works as an accountant at my fathers company. We have been happily married for 12 years. With our hectic schedules, children have just not been a real possibility and to be honest, neither one of us are in a hurry to become parents...

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Somewhere else.

by latexdoll on May 23, 2010
Fantasy

Waking up this morning I bet you didn’t know it would be the last day you spent here on earth. Climbing out of bed you hit the alarm clock for the third time, you can’t quite place what is wrong, you just can’t seem to get out of bed. Getting ready for work is more of a chore than usual. For whatever reason nothing seems to want to cooperate. Your shower hea...

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Miss Identified

by Dayeandknight on Sep 7, 2008
Transsexual

Your sister Sara is out of town this week at a big science convention and she has entrusted you to look after her house while she's gone. Sara has always been a big nerd when it comes to electronic gizmos and computer stuff. She’s the only one you know that could get excited over a whole week of droning lectures on astrophysics or whatever they talk about du...

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Sissy's sister

by acepmn on Nov 21, 2015
Bisexual

Anna had always seemed like a good girl. Our parents weren't suspecting anything bad about her, just like they didn't suspect I was spending a lot of nights dressed as a girl in my room. I had skirts, cute tops, slutty dresses, panties and sexy thongs, butt plugs, dildos, cockrings, vibrators... A whole panel of varied toys to play with while dressing up. I...

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First Time Cross Dressing

by fethishboy on May 1, 2003
Fetish

Lisa Smith was always a bit spoiled. She was a sexy and teasing little minx. She was 22 years old with a smoking hot body. She loved to tease and be treated like a princess. She acted all sweet and pretty but she had a wild side. She loved to control men. She loved to make her buy her stuff. She loved to cock tease. She made a lot of money on it. She loved t...

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Bullied

by Testytesterton on Sep 12, 2020
BDSM

You are an 18 year old boy surrounded by bullies everywhere you turn. Your high school has apparently elected you the mascot of the losers and wimps and selected you to receive the lion's share of attention from the bully boys while simultaneously being ignored at best by the girls you lust after. At home, your family is cruel and controlling or coddling and...

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