Gay Crossdresser Stories

23,018 results
Orientation
Length
Source
Infinite Scroll

Aunt Margo - The Family Slut Ch. 06

by Kalimaxos on Jan 6, 2020
Loving Wives

This story is the property of the writer Kalimaxos. In memory of my aunt. A slut of epic levels and magnitude. And a heart of gold. Characters in this chapter: Margo, my uncle's wife George, my mother's brother and Margo's husband Vince Romano, NYPD detective and one of Margo's conquests Angie Romano, Vince's divorced wife Linda, one of Margo and G...

Audition Ch. 03: Chens Pt. 01

by craigool on Jul 6, 2020
BDSM

"Audition 03: Chens Part 1" by CraigOOL BDSM -- A desperate woman sells herself and her daughter into slavery [Author's notes: Warning! This is a BDSM sex story. There are strong Dominance and Submission themes in this story. There are some interracial themes in this story. This story has substantial male/female, female/female, MFM, FFM and group sex sexua...

Dakota's Surprise Pt. 04

by mfan2112 on Oct 12, 2020
Transgender & Crossdressers

Dear Readers, I hope you enjoy this piece. If you like it, please check out my other works. You know, dear reader, Dakota learned in her tax class, the IRS code is broken into sections, which are similar to chapters in a book. Many sections of the IRS code refer to other, earlier, sections and are only understood in the context of what came before it. So,...

Willingly Cuckolded for Love

by silkstockingslover on Sep 25, 2017
Fetish

Summary: A happily married couple both submit to her Dom ex-lover. Note 1: This story is dedicated to Mike and Laura, a married couple, who requested this story. Note 2: Estragon, as always, many thanks for your copy editing work and LaRascasse for his plot suggestions. Warning: Please note this is a story about cuckolding that includes gay submission...i...

Jackie and Artie Ch. 02

by Goodhusband on Sep 18, 2017
Loving Wives

This is the second episode in a series entitled "Jackie and Artie". If you have not read the first episode of this series, I encourage you do so before beginning this chapter. "Jackie and Artie" is a romantic story about a dominant hot wife and her submissive cuckold husband. While they have a deep and abiding love for each other they do lead an alternative...

The Vicar of St. Dunstan's Ep. 22

by Nigel Debonnaire on Sep 19, 2017
Loving Wives

A request for a specific seduction got me thinking it was time to include storylines that focus more on the gay characters around St. Dunstan's. I've never wanted the Vicar to be the center of every sexual relationship or escapade in the series, so this will explore how the other half is living, so to speak. It was one of my favorite holidays again: Twelf...

The Podium

by Baron_Cumhausen on Sep 12, 2017
Group Sex

There's a small auditorium at the small community college I'm attending this summer where, in the late afternoon, I join several other students on Tuesdays for a public speaking workshop. It's nothing formal, no teachers or TAs. It's just a half dozen or so of us guys who decided to start a summer speaking club to conquer our fear of speaking in front of f...

A Sugar Cube Melts

by JimBob44 on Sep 19, 2017
Group Sex

*Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. Also, if male bisexuality offends you, hit your backspace key now. ***** Murphy Margot received the phone call from Glen, his step-father, a drunken, angry and sobbing phone call. Numbly he heard that his mother had been killed at work. His mother and...

Therapy

by B_Couric on Sep 19, 2017
Fetish

The following is a cuckold themed story with minor male on male contact. It's more psychological than sexual, but there is both. ***** Jack parked the car in a virtually empty lot, behind the medical office. It was already 7 pm and the daytime medical crowd, general practitioners and blood laboratories had already shut down for the day. Marlene often used...

Former Roommates Connect

by adani on Jul 2, 2018
Exhibitionist & Voyeur

Part 1 I always thought my old roommate was gorgeous, but as I got to know her over the years I also discovered what a great person she is. She is caring and generous, as well as having a wicked sense of humor. Back when I met her, the fact that she had a great ass and gorgeous blue eyes was just about enough for me to agree to have her share my apartment....