Crossdressing Strapon Stories

2,832 results
Orientation
Length
Source
Infinite Scroll

A Look Into My Mind: Uncle Sissyboy

by rickiee_2002 on Sep 25, 2017
Fetish

The telephone was ringing and the voice on the other end was my sister-in-law, Arlene. She asked me, in her usual cold manner, if she could speak to my wife. "Hi Rich, can I please talk to Debbie". There was something about her that I could never really stand, but she was my wife's sister, so I always kept a smile on my face when I was around her. "Arlene, c...

Neil and Kate Explore Anal Desires

by neil96nz on Sep 26, 2017
Loving Wives

Chapter 1 Kate and I were an everyday couple. Together for two years and with two children from Kate's previous marriage. We were both in our early forties and both highly attracted to each other emotionally and physically. We both thought the other was ideal, although we both did carry a little extra padding in the usual places. I am 6 foot 3 broad shoulde...

What are Sisters for? Ch. 01

by Dreamthiev on Sep 13, 2017
BDSM

(Author's Note: This story contains elements of incest, lesbian sex, and transgender sex. If any of these are offensive to you then this might not be a story for you. Also, there is a bit of character and story development before the "action" really starts, so if you're looking for a quick stroke-story you might also be disappointed. Otherwise, I hope you en...

The Board Room

by sydian on Sep 16, 2017
Transsexuals & Crossdressers

1 Bigots The firm was not without its bigots. Though Sydd had gotten there by talent alone—her first case was sexual and gender discrimination...she brought in the client—a wmn, just like herself: educated, professional, sophisticated; discriminated against, and highly put out—she won big—really big—and the 'big daddies' couldn't just let her walk....so an...

Suburban Wife Ch. 05

by qm2x1798 on Sep 19, 2017
Group Sex

This is the continuing adventure of a couple as they expand and grow sexually while staying with a dominatrix and her servants. Special thanks for AC for helping edit this chapter. Constructive comments about the story and the characters is welcome. The sun had not yet crested the horizon, and John was slowing leaving the depths of his dream. He had bee...

A Couple Pt. 03

by SierraSprite on Sep 16, 2017
Novels and Novellas

Author's Note: Oscar discovers his women are full of surprises. If you are just joining the story, the first two parts are essential and may be found at and http://www.literotica.com/s/a-couple-pt-02 ***** After a long flight from London, Natalie picked me up at the airport with a bright smile and a warm kiss. We drove down the Peninsula freeway and I loo...

My Perfect Other Half Ch. 06

by Katiekatsman on Feb 4, 2020
Fetish

Chapter 6: Destiny - The Making of a Goddess Tyler pulled into the driveway around 5:30 that evening. Because an unfamiliar car was parked by the garage door instead of Destiny's BMW, Tyler's curiosity was piqued. "Dez?" He called once inside. She appeared from around the corner. Her eyes were blurry, her makeup a mess and she generally looked terrible....

First Meeting Ch. 02

by Gamblnluck on Nov 16, 2020
BDSM

This is a continuation of my story 'First Meeting'. I suggest you read that one first. It contains elements of domination and submission but very little sex. All characters are over eighteen. ===================== "You see, unlike other dommes you might encounter," Brenda said "I have no interest in your money. I really don't care much about this thing han...

One Fateful Evening Ch. 01-10

by Pippa on Sep 16, 2017
Transsexuals & Crossdressers

Pippa's Story. (Part One.) One Fateful Evening… It all began as a bit of a joke really. We'd all been out clubbing in some really raunchy night-spots and were still high on both the atmosphere and the two Love-doves that we'd swallowed a few hours before. As the night wore on and, as morning was quickly rearing its bright and beautiful he...

Quiet Servitude Pt. 01

by AmandaMI on Sep 15, 2017
Transsexuals & Crossdressers

Author's Notes Before reading this story please be aware that that some people would label this work as obscene and pornographic in nature. It contains several themes including transgendered, homosexual and lesbian issues in addition to graphic sexual descriptions. To make the action flow more freely and the stories light-hearted, I have taken a socially n...