Crossdressers Stories

12,121 results
Orientation
Length
Source
Infinite Scroll

Finding the Perfect Fit Pt. 19

by Joshana on May 11, 2020
Transgender & Crossdressers

February 12 Man, reading back over that dream is a fucking trip! Jesus I was out of it... But if I'm being completely, totally honest with myself, I still feel the echo of that gut wrenching disappointment when I reached down and didn't find anything sticking up. I expected it to be there, I knew a dick was there without question and suddenly, it wasn't. Ty...

Intersex Pajama Party

by Rallynoangels on May 11, 2020
Transgender & Crossdressers

**All characters are 18 or over. This is a little different from my normal type of story. Be sure to check the tags.** * Delilah had a complex medical history. For months after her birth she had several surgeries to "Fix" her. Her parents told the doctors keep her as natural as possible. No implants, no amputations, and trying to save as much utility and s...

The Good Neighbour Ch. 04

by MicheleNylons on Sep 9, 2019
Transgender & Crossdressers

Chapter Four - Retribution Then... Robert Brinkley recalled his last few months in prison. He was enamoured with a transvestite prisoner named Mary Reynolds. Most of the old timers didn't condone men having sex with other men in prison but the younger breed was more enlightened. A lot of prisoners would accept blowjobs from submissive or effeminate inmate...

Bluepilled Ch. 05

by petmyhead on Jan 6, 2020
Transgender & Crossdressers

I've always liked science. No, not exactly true. I can track it all the way back to the end of November, the week after my ninth birthday. My Aunt Rose had stopped by with an early birthday present for me. My very first chemistry kit. Such a simple thing. Baking soda and vinegar. Slimes made from borax or cornstarch. Color changing solutions. To me though...

Revealed to My Roommate Ch. 01

by gaildaniels84 on Jan 6, 2020
Transgender & Crossdressers

Paul watched the clock on the office wall with rapt attention. He'd finished his work hours ago, the truth was doing the minimum at this dead-end office clerical job didn't take more than a couple hours of hard work a day, and since then he'd tried everything to distract himself. He'd been to the water cooler a suspicious number of times, taken several bathr...

The Surrogate Ch. 03

by MicheleNylons on Jan 20, 2020
Transgender & Crossdressers

Chapter Three - Redhaven To say that Mila was excited when she was handed the keys to the silver BMW Z4 would be an understatement. She followed Peter who was driving his new Mercedes A-Class, who was in turn following Brian and Dianne Hislop who were driving a late model SUV. When they flew into Redhaven yesterday Mila had been amazed by the wide expanse...

Working Out Issues Ch. 12

by blake1 on Jan 20, 2020
Transgender & Crossdressers

"Adam, I love you so much, and I really wanna have sex with you," I said. Adam hesitated. "What's wrong?" I asked. He shook his head, "Sorry. I just feel like I'm waiting for context." I giggled, "No context. I just love you. And you're really sexy." "You're really sexy," Adam grinned, and before I could make fun of his shitty comeback, he kissed me har...

He is Your Master Now Pt. 02

by DomAlphamann on Jun 1, 2020
Transgender & Crossdressers

Ambrose Sweet meets the fierce Cassilda Chambers, a sexual wanton whom he comes to believe may be of eldritch origin. Before long, he finds himself ensnared in a scheme to eradicate his will and fundamentally change the nature of his entire being. He is Your Master Now Part 2: A Most Eldritch Vixen Six months ago, Ambrose Sweet was walking in Midtown Manha...

Crazy Hot

by LeatherWallett on Jun 8, 2020
Transgender & Crossdressers

Crazy Hot I had pretty much given up on dating, which was a good thing, as the Covid crap had everybody scared to death nowadays so nobody was really dating anyone always. I had given up dating because I seemed to be a magnet for crazy. My dad said I could be dropped into a million women with one that was crazy and that was the one I would date. My experien...

School of Futas Ch. 03

by FutaMonster on Feb 11, 2019
Transgender & Crossdressers

Author's Note: Hi everyone. I'm really sorry for the extended delay between the second and third chapters. I want to thank everyone for their patience and for the messages I've received encouraging me to continue the story. The extra motivation was a real help. I hope you find this chapter a good read and I'm sure there won't be anything near to the same d...