Stepbro Pegged While Crossdressing Story Stories

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Erika's Story Ch. 06

by Quantarx on Mar 2, 2020
Transgender & Crossdressers

This is the sixth segment of the Erika story, if you would like to know how we got to this point please go back and read the other chapters. Also I appreciate feedback, comments, and a 5 star rating is appreciated if you think the story warrants it. *** I slept like a baby that night, I think I was worn out from all the excitement of the day before. Mary h...

My Stepsister has hypnosis powers

by Jcastle on Apr 29, 2025

Billy waited. Nervously. He was about to meet his new stepsister. His mother had been dating a powered man for a bit. His name was Daniel. His power was using sex pheromones to influence (control) those attracted to men. His presence puts them in a horny suggestible state. Bill didn’t like think of that. He didn’t want to see his mother like that. He had nev...

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Stranger Fuck

by hfernandez1983 on Sep 13, 2017
Transsexuals & Crossdressers

It's been a while since I have written something. It's mostly because I have felt so uninspired and didn't know what to write. My main fantasies these days revolve around a man crossdressed while he is pegged by a woman who likes to dress as a man. My last story series Jenny & Mike got a decent reception and I wanted to write more. But like I said, I've...

Exploring Sexuality: A Pegging

by silkstockingslover on Sep 25, 2017
Anal

Summary: Husband is pegged by sister-in-law with wife's permission Note 1: Thanks to Robert, goamz86 and Wayne for editing. Exploring Sexuality: A Pegging I was almost in the city when my cell rang. I glanced at it and saw it was my sister-in-law Sabrina. I sighed. I loved Sabrina, but since her divorce she had been as exciting as a Nicholas Sparks mov...

A Surprise Ass-Fucking in Panties

by hummmph on Sep 13, 2017
Fetish

A very curious thing happened to me the other day and I feel I need to share it with you... I have been 'mildly' crossdressing for over a year now. I say 'mildly' because I am not into full feminization, I just love the feel and look of lace panties when they are hugging a good looking cock, not to mention the taboo. I have taken to wearing stockings too wh...

Caught Out at Work

by alexis19901 on May 12, 2020
Fetish

For those of you who have read the stories that I've already put on, you will already know a bit of my back story, but for those of you who are reading a story of mine for the first time, I will give a bit of background in the intro. WARNING - This story contains m/f, pegging and some crossdressing. So, for those of you who aren't aware, I've taken to wr...

Pretty in Pink Ch. 06

by jealouscuck on Sep 25, 2017
Transsexuals & Crossdressers

My wife, Jessica, not only found out about my crossdressing, she researched and accepted my fetish as part of our sex life. Our adventures had escalated from going out as "girlfriends" to some light exhibitionism and finally to a "lesbian encounter" with a pretty girl. Never in my most intimate moments would I have thought of anything like we now found so...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

G-Punk Community (English version)

by Aregon on Apr 22, 2025

My name is Leon. I’m 19 years old, about 5’6” (1.69m) tall, with long blonde hair and a slim, somewhat feminine build. For a while now, my plan after school has been to explore a bit, earn some money, and maybe even move away from home for a while. My relationship with my family isn’t exactly great, and most of my friends went abroad and barely stay in touc...

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A Big Surprise!

by rj1774 on Jul 6, 2020
Transgender & Crossdressers

As a man's sexual desires come to light this story features, femdom, pegging, crossdressing, and dating a TS woman. Please share any constructive criticism or where to take a next chapter. I hope you enjoy! **************** My sweet, caring, brilliant girlfriend, Stephanie, and I have been dating for a few months and we decided to plan a long weekend get a...