Gay Crossdresser Stories

23,018 results
Orientation
Length
Source
Infinite Scroll

Best Friends

by MrHenry on Sep 15, 2017
Transsexuals & Crossdressers

I had known Brian forever, it seemed. He had just gone through a divorce and I was trying to cheer him up. He wouldn't tell me the reason for the divorce, so I figured she was probably seeing someone else. I was over at his new apartment, helping him get settled in. I picked up a box and asked him which room it belonged to, when the bottom of the box gave ou...

Barbie's BBC Beginning

by jacki697 on Jun 9, 2020
Transgender & Crossdressers

I had always been curious about men. I had always wanted to experiment but alas I was way too scared of being "gay" to ever follow through on any of my urges. Chalk that one up to 18 years of living in a conservative Christian community. Instead I left my sexual urges to the alone time I had to indulge in my other fantasy of crossdressing. I loved the thrill...

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...

You Got the Part!

by Checkmate215 on Sep 26, 2017
Transsexuals & Crossdressers

Coming up with the rent every month was becoming more of a challenge. I was a on again off again actor/waiter. My tips were good but I had to supplement them with acting gigs and odd jobs. This was the price to pay for freedom. I had a one bedroom apartment that ran me 1500 a month. I was avoiding taking on a roommate at all cost. I loved my privacy. A frie...

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...

Mom's Big Black Hobby Ch. 03

by MiddleKoala on Jun 15, 2020
Transgender & Crossdressers

This story has with incestuous and homoerotic themes. If you are offended by such, do not read. This level of depravity is not to be taken lightly and the deeper down the rabbit hole you go the more you will find that may offend you. You have been warned! All characters in this story are over the age of 18. The entire story is fiction as are all characters....

It Started As A First Date

by spandexman on Aug 30, 2017
Fetish

As far as first dates were concerned, Roxy Fox, the 23-year-old, 5'11", Barbie doll faced gorgeous, secretary, with a strong dimpled chin, high cheekbones, big almond shaped hazel eyes, thick wavy shoulder length fiery-red hair, and a very firm, but extremely curvaceous 38FF-26-38 hourglass figure that her skintight white spandex pants, tight red spandex top...

Dreams

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

"Hey! Hey! Wake up, wake up!" "What? Jo, what is it? What's going on?" "I think you should be telling me that!" "I don't understand." I was slowly coming round now, But I was still mystified as to why my wife had woken me at 2 a.m on a Saturday morning. "Erm your cock is as hard as nails and you were waving your ass in the air," Jo said, starting to laug...

I Accidentally Sucked Dick! Pt. 01

by CDJulie on Aug 18, 2017
First Time

I've never given anyone head before although I thought about it for years. I'm a lifelong crossdresser but closeted. I was never brave enough to approach anyone and I shied away from any offers that were made. Mostly, because when I fantasized about sucking dick it was always as crossdresser, more specifically, in the role of a girl. So when I was 33 I vis...

How I was Forced Out of the Closet

by gtanya on Apr 4, 2018
Transsexuals & Crossdressers

I was again dreaming of the night I would lose my anal virginity. It had been such a constant since last 3 weeks. I had been talking to a beautiful CD named Rachel since last 6 months and with the thought of meeting her in person, I had planned a vacation to China where she was living. The only problem that I had here was I was going to be on the vacation wi...