Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Julia, Ben and Lisa Ch. 16

by chloejacobs83 on Mar 31, 2020
Transgender & Crossdressers

Ch. 16: Wednesday A few quick notes: 1. this is the sixteenth chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned * "Oh honey! Y'all are sooooo cute in those shorts." I semi-s...

Julia, Ben and Lisa Ch. 14

by chloejacobs83 on Mar 23, 2020
Transgender & Crossdressers

Ch 14: Monday A few quick notes: 1. this is the fourteenth chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned * I woke up late, almost 9 o'clock, but felt great. I was excited...

Princess Chelsea

by Sublithium on Sep 25, 2017
BDSM

Ever since puberty I have been enamored with beautiful dominant women. Most of the fantasies I have ever had revolved around being at the feet of, and wrapped around the finger of a beautiful femme fatale. Throughout my entire life I have sought these types of women but have never found one that really shared my desires. Sure, I have met my share of demandin...

Neck Deep Ch. 03

by XtinaSmith2017 on Sep 18, 2018
Transsexuals & Crossdressers

"Mm..." Brittany moaned lightly, arching her back under the warm embrace of the duvet as she felt her mind and body begin to stir from the loving embrace of sleep, the vibrant memories of her dreams, many of which had been delightfully sexual and erotic, quickly growing distant and evaporating away as she slowly came around, her eyes opening slowly to greet...

Important Business Comes Up Ch. 02

by Emmcee20 on Sep 13, 2017
Transsexuals & Crossdressers

In the opening chapter of this story Jason Meadows has arisen to the level of Vice President in an advertising agency and immediately become the target of office predator Dana Jones. She quickly discovers his interest in wearing lingerie under his business suit and, after an initial meeting, invites Jason to her house for further discussions about his new ac...

The Writer's Secret Conclusion

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Synopsis: Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of feminizing her husband. How far would they go? * Chapter 13: Laura Blossoms A routine developed. During the weekdays, Kathleen would come over to watch Loren work. They wou...

Best Girl Ch. 06

by afstories on Sep 14, 2017
Transsexuals & Crossdressers

TO BE READ BY ADULTS AT LEAST 21 YEARS OF AGE ---------- Laying in bed, Todd heard someone rustling from the other side of the room. Not moving himself, he whispered out the side of his mouth. "Candy, do you hear something?" Chris woke up and said, "What?" "Shh. I think there's someone in our room." Both Chris and Todd slowly rose up and saw a figure st...

A Bend in the Road Ch. 03

by Oldguy45 on Sep 14, 2017
Transsexuals & Crossdressers

This story has been on my mind for a long time. It involves two characters from previous stories of mine: "A Bend in the Road," Chapters 1 and 2. This story is going to take a bit of a different direction from the other two. All of these stories are pure fantasy and maybe a little wishful thinking on my part. I hope you enjoy this one. * I had been out of...

Literotica

by komrad1156 on Sep 13, 2017
Mature

"Dear RomanticGuy05, I'm not sure why I feel the need to apologize for writing you, but if you knew me, you'd understand. That's just me. I suppose it's because sending you an email makes me feel like I'm intruding into your personal life, and since you don't know me, I'm sure you see me as some stranger butting in without an invitation. So I hope you'll fo...

Michele Nylons' True Stories Ch. 04

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

This is a continuation of my True Stories series, where I tell my readers about my real life adventures as a part time Transvestite. In this instalment I will tell you about my most recent encounter; my first encounter for some time, and also for me a milestone; my first time out and about dressed as a Transvestite. This is the story of my latest encounter,...