Gay Crossdressing Stories

23,246 results
Orientation
Length
Source
Infinite Scroll

Playing with a cheaters wife Ch. 01

by Indianaboy6555 on Mar 30, 2020
Loving Wives

The story starts with me playing on my favorite app one evening. I got a notification telling me someone was interested. Then they messaged me. We chatted for a bit, then the guy sent me his picture. I w was shocked when it popped up on my screen. It was a good friend of mines husband. It probably shouldn't have surprised me as much as it did. He's the onl...

Pegged Ch. 02

by ndeavour on Dec 30, 2019
Group Sex

Editor's note: this submission contains scenes of gay male sexual content. * A week had gone by since "the Peg Sisters" had re-emerged from retirement. My gorgeous wife Alison, five-eight with 38DD boobs, legs that don't quit, red hair and green eyes and I had always had a great sex life -- now it was heading in an entirely new direction. Her best friend,...

I Make Believe I'm a Cuckold

by donaldelliott11 on Jan 20, 2020
Fetish

[Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either one. The story carries the label "BCS". In other words, if I put it in the Loving Wives section, it would be lambasted as Bi Cuck Shit. Tough crowd over there.] +++++++++++++++++ Every few weeks I travel with a female coworker to three-da...

Kaycee Ch. 03: Evolution of a Fantasy

by BillandKate on Mar 3, 2020
Exhibitionist & Voyeur

In the previous chapter (Kaycee: Confessions), Tony, now that he understands his voyeuristic tendencies, listened and was highly aroused as Kaycee shared the secrets of her relationships with two different sets of college roommates. Kaycee explains that, for her, most of the excitement was performing for one roommate by fucking the other - she's an exhibitio...

The Duplex Ch. 03 - Making Plans

by TheCandyManCan13 on Jun 22, 2020
Fetish

[Yes, I have been away. Doing things. Living Life. There are no direct same-sex scenes for the main character in this episode, just setting up moments for later. As such, I have put it in the "Fetish" category to avoid confusion for those who don't know what my stories are about.] Chapter 3 - Making plans I woke up to the sounds of sex. I looked over to se...

Lisa Cuckolds Jake

by lapraline70 on Oct 20, 2020
BDSM

I met Summer, what - 1999...? - 14 years ago. New job, new folks, new city. I was married at the time to someone I knew I should never have married (a straight girl who never grew up; different story) and while there were many opportunities to take that right turn and keep on going, I was always faithful. Until my wife wasn't. Divorce was painful but ther...

Exploring Bisexuality

by adani on Sep 28, 2020
Transgender & Crossdressers

Part 1 We knew each other from face to face interactions but that was only really as acquaintances. Then, when we were living in different countries, we became a lot closer. It is funny how technology enables that to happen these days. She knew my big secret, that after always thinking that I was a heterosexual guy who was a little effeminate, I now acknow...

Crimson Reborn Ch. 15

by Quixerotic1 on Sep 28, 2020
NonHuman

Author's Note: Due to the setting of this chapter, I'd like to reiterate that all characters in this story are above the age of eighteen. Lucy leaned back on the desk as Oliver's forked tongue lapped at her slit. She ran her fingers through his hair, stroking him like a pet as he desperately tried to please her. One room over, the remaining students diligen...

Mindy's Moving Day - CFNM Ch. 01

by BuckyDuckman on Sep 25, 2017
Fetish

Author's Note: Humiliation, CFNM and pegging lie ahead! I've had this idea for a while about an adventurous married couple on the edge of opening a new chapter in their married life. I hope you enjoy reading it as much I enjoyed writing it! On her first day in town, Debbie and I were Mindy's only friends. The professional moving company hired by Mindy's...

Claire Reborn Ch. 01

by HMAuthor on Sep 19, 2017
BDSM

The red-eye from Hong Kong had been late and I was again regretting the flight choice. Deadlines are deadlines though, so I stood waiting for the carousel to show some sign of movement that might indicate baggage handlers attempting to make up for lost time. Fat chance! A small disturbance to my right caught my ear. "Stupid bitch, whadya mean you lost your...