Crossdress Stories

204 results
Orientation
Length
Source
Infinite Scroll

The Door to Door Stocking Salesman

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

In 1959 Brian Macklin was in his mid forties and was making just enough money to get along; his dreams of affluence were ruined when his marriage failed. He used to be a sales executive for an affluent London based firm but all of that came to an end when his wife left him; his father-in-law owned the firm where he worked; say no more. To make matters worse...

Magic is as Magic Does

by AmethystMare on Oct 14, 2017
Transsexuals & Crossdressers

This is a short work of erotic fiction containing furry, or anthropomorphic, characters, which are animals that either demonstrate human intelligence or walk on two legs, for the purposes of these tales. It is a thriving and growing fandom in which creators are prevalent in art and writing especially. These stories have been public for some time, but I am sl...

Becoming Jessica

by Lovely_Jessica on Sep 25, 2017
Transsexuals & Crossdressers

It all started after I told Emma I no longer wanted to have children one day after work on a Friday evening. Over the past few months we were actively trying to procreate after 5 years of marriage. We originally never wanted children, but that apparently changed after her proverbial "baby clock" starting ticking. Don't get me wrong the sex was great and we w...

The Craigslist Killer Pt. 03

by thrillerauthor on Sep 14, 2017
Transsexuals & Crossdressers

I lay there in stunned silence, my death sentence ringing in my ears. "I have H.I.V," Ron just told me. How many times had I warned myself about the dangers of dating on Craigslist? How many guys had I blown off because of the teeniest suspicion that they might not be safe? How much time did I have? I bolted out of bed and raced into the bathroom. There w...

Tranny at the Truck Stop

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

The Perils of Pauline -- Trannie at The Truck Stop Paul sat behind the wheel of his Mustang, the windscreen opaque with heavy rain. It had been raining hard for the last hour and he was hoping it would have stopped before he reached the truck stop. He looked through the windshield as the wipers lazily swept back and forth across the glass. The sodium vapour...

The Surrogate Ch. 02

by MicheleNylons on Jan 20, 2020
Transgender & Crossdressers

Chapter Two - Becoming Mila Mila slept in a satin nighty and panties that night but she was untucked of course. There was no sign of Peter Randal and she had the apartment to herself. She had practiced her makeup for a while and walking in heels and then after a light dinner she retired. She had tried on her sister's clothes and divided them into two piles...

Girlfriend Problems

by colleenslittletoy on Sep 13, 2017
BDSM

This story is about a woman humiliating a man. It includes crossdressing and cuckolding. After a heartbreaking divorce I wasted a a few years in mourning, reflecting on all the things that had gone wrong in the relationship. What had started as an equal-sided affair turned into a female dominated one. Basically, her pussy ruled. Finally pulling myself...

The Ten Game Pt. 04

by THEGREATDANE99 on Apr 2, 2018
BDSM

Summary: -Sam and Marina get invited by their highschool friend, Catherine, to an exotic sex club -They pass the initiation test with the help of a red headed waitress named Audrey -Sam can't help openly bragging about the Ten Club to anyone that will listen -Trixie, a dominatrix from the Ten Club publicly dominates Sam and Marina as punishment for blabb...

Morning Glory

by dreadknots on Apr 25, 2018
Transsexuals & Crossdressers

Reviews for my last crossdress-y story were pretty good! Hurray! This one is a little more teasing in nature, but is ultimately pretty fuzzy. I am a sap. *** Hardcore Fitness was the classiest gloryhole in town. All the right people knew what went on behind the illusory front of a 24/7 gym, and the syndicate behind its operation paid off the right guys in...

How Nathan became Natalie Ch. 04

by saintlycd on Jan 7, 2018
Transsexuals & Crossdressers

The school year ended and Kevin graduated and Jenifer and I went home for the summer break and we got part time jobs for the summer. Jennifer got a job working with her father's very large and lucrative construction company as a marketing representative; which was her major in college. It was a great experience for her but due to the fact her father's constr...