Gay Cross Dressing Stories

3,699 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Cross-Dressing, Gay & Lesbian Sex 04

by SusanJillParker on Aug 30, 2017
Gay Male

There are no underage characters in this story. All characters are over the age of 18-years-old. Daniel and Martin swinging in a foursome, k-i-s-s-i-n-g. * "One more thing?" He looked at her as if she was about to ask him for a divorce. He looked at her as if she was about to ask him if Greta, Maureen, Ebony, Janya, and Veronica, along with Martin, coul...

Bathhouse Heaven Ch. 32

by glory_first on Aug 22, 2018
Gay Male

The bathhouse was fairly empty this Wednesday afternoon, a reminder of different rhythms from the past. Following the familiar routine, today with more space to undress than the case lately. The beer was quenchingly cool, and quickly finished. Going upstairs, I walked towards the sling room, noticing a couple of men going different ways than my path. How...

Bathhouse Roles

by glory_first on Sep 14, 2017
Gay Male

Arriving right at the bathhouse's opening time on Tuesday, the sky dark enough to think that rain would be arriving soon, the entrance was busy. 5 stacked bundles of the latest edition of a free local gay magazine were outside the door. Going in, before I could mention the delivery, a man with a blue t-shirt that read "I like face fucking - ask me" brushed b...

Cross-Dressing, Gay & Lesbian Sex 07

by SusanJillParker on Aug 30, 2017
Gay Male

There are no underage characters in this story. All characters are over the age of 18-years-old. * Emma and Daniel invite Veronica and Martin over for some sexy fun. Daniel and Martin have bi-sexual sex while watching their wives having lesbian sex "Won't you join me?" Directing his conversation to his cock, Martin gave Daniel's big bulge a raised eyebr...

Cross-Dressing, Gay & Lesbian Sex 05

by SusanJillParker on Aug 30, 2017
Gay Male

There are no underage characters in this story. All characters are over the age of 18-years-old. * Daniel's one time bi-sexual fantasy consumes him "Maybe if you allowed me to have sex with Martin," said Emma to Daniel pausing without finishing her thought. She looked at him with teasing eyes and flirty sexiness in the way she used to look at him when t...

"You Go First" (Ch. 10)

by donaldelliott11 on Mar 2, 2020
Gay Male

This is the 10th in a series. "Samantha" was the 3rd chapter and "Donnie" was the 4th. I regret that my inconsistent use of titles prevents Lit from properly displaying the series. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help authors improve their writing; star rating...

Taking Him as Payment

by CKBrooks on Jul 4, 2018
Gay Male

Don't panic if this seems familiar! This is the original version of a scene from a book I wrote that I ended up majorly toning down for the actual novel (it ended up being a love story, so I wanted to start the book off far less... mean). I still liked the scene I originally wrote, so I decided to put it here for people to enjoy! This story has non-con eleme...

Graham and Griffin Ch. 03

by emilyandalucia on Aug 18, 2017
Gay Male

Chapter 3 Griffin's POV Graham just came out to me. I don't know how to react. My first reaction is to grab Graham's hand and say, "Me, too," but instead I do something that is horrible, unforgivable. I get up and walk out of the coffee shop. I don't really know where I am. I decide to go left towards the thrift store where we had been a half hour ago. Wh...

First Experience With A Man Ch. 1

by girlboybootsie on Aug 18, 2017
Gay Male

I wasn't always attracted to men. In fact, until I was 18, I never felt confused about my sexual orientation. In terms of sex, I was only attracted to girls, especially sexy ones who dressed in provocative and sexy clothes. I was popular with girls, and had lost my virginity when I was 14. Without meaning to be immodest, I was, and am, a very good looking gu...

Sharing Secrets Pt. 05

by Showoff888 on Sep 14, 2017
Gay Male

I'm a shy, smallish, slightly pudgy from my waist down, a bit wider in the hips, butt and rounder legs, small delicate hands and feet. I think I'm a very passable nubile little Japanese girl, with shoulder length black hair, small nose, full lips, long lashes, and a tiny penis, and obviously flat chested. This summer, my Mom divorced my kinky Dad, for someon...