Gay Cross Dress Stories

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Infinite Scroll

The Christmas Eve Wish

by endthedream on Aug 18, 2017
Gay Male

It was a warm early Spring day. It was Monday. School out in two weeks. He was a teacher. He was fifty today. He taught senior English with one Junior class. He has been teaching since he was 25. He stood at his lectern and looked out at the class. Some here and there looked up from their notebooks and their texts, out the three oblong windows, at the warm s...

Suck Thy Neighbor

by ret123 on Apr 8, 2019
Gay Male

I am a masculine, aggressive businessman who keeps himself in good shape by lifting weights and cycling almost every day. I am married and have two kids who are terrific. I work hard, make a lot of money and go to church almost every Sunday. I was heterosexual and faithful to my wife until I was in my 50s. My attractive wife is a lot younger than me and we h...

St. Andrew's Cross

by MadExhibitionist on Sep 14, 2017
Gay Male

This is a true story from the Bournemouth gay sauna-bar at its old location, when it had a dedicated playroom. Locals will know what I mean. The sauna-bar was huge. Half of it consisted of showers, saunas, hot-tubs and the like. Separated by a bar in the middle, the other half was a dark labyrinth of rooms. Some were private, some had mirrored windows and s...

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...

An Afternoon 'Bi' the Pool

by Rckymtn110 on Aug 18, 2017
Gay Male

I had always felt a little different growing up. I was probably a little more sexual than most people were, but it was a private thing. I didn't sleep around or do anything most would consider wild; but nonetheless, a part of me was different from most guys. It is difficult to explain, but it is as if I have lace under my exterior of leather. It wasn't an ev...

Bicurious Fantasy Becomes a Reality Ch. 02

by StraightButCurious on Sep 25, 2017
Gay Male

A few days had passed since I sucked cock and took it into my ass for the first time. Greg, my coworker and good friend, had easily seduced me into worshiping his big cock and plum-sized balls with both my mouth and my ass. I considered myself extremely lucky because my first gay experience was with a well-endowed man in every aspect. Just the thought of his...

Pony Boy Ch. 08

by ChestersBoi on Sep 14, 2017
Gay Male

Gosh, has it really been eight months since I last posted. Oops Sorry. I guess you'll need a catch-up as much as I did. So here's the story so far. Ben, when desperate for a little extra cash, discovered that there was good money to be made running in races as a 'ponyboy'. Despite being assured that the worst he would be subjected to would be a 'certain amo...

How Sweet It Is! Ch. 02

by walterio on Sep 16, 2017
Gay Male

Rick, Tom and Danni had a very routine first week as roommates. Rick and Tom were busy in their new jobs and did not go out clubbing or drinking after work Monday through Thursday. In fact they worked late, came home and had a light snack for dinner. Danni was a sweetheart as he dressed as Danielle and made a light dinner for the guys. His reward each evenin...

I Make Believe I'm a Cuckold Ch. 04

by donaldelliott11 on Feb 10, 2020
Gay Male

This is the fourth and final chapter. You should read the others first. This chapter contains a scene of incest between two adults. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help me improve my writing; ratings help other readers find what they most will enjoy reading. Ra...

X Rated Robotic AI Ultimate Lover

by Alluring_Crimson_Shifter on Aug 18, 2017
Gay Male

*** "--------------------------" Chapter One: Home Alone with a Statute "--------------------------" Janie was home alone. Her husband was off on another lengthy business trip and she was so horny that at times she could not think straight. She stayed in bed and started rubbing her breasts. It felt so good that it was almost like being with her man on a...