Gay Dress Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Dress Rehearsal

by ManInTraining on Aug 18, 2017
Gay Male

It had been a tight month and that's what had decided him. His rent was due – and he'd make it – but he wouldn't be eating for the rest of the week. Male escort work beckoned... He knew enough about the industry though to know that if he wanted to do well, he'd need to be available to male clients or he just wouldn't make it in his city. So, here he was sit...

Dressing Room Encounter

by rimaday on Jan 6, 2018
Gay Male

It had been a rough few weeks. I had been traveling non-stop and arrived at the airport for a convention and business meetings filling the whole week. My flight arrived on Saturday afternoon ahead of a Sunday evening dinner and convention starting Monday. It was a new town for me and, I thought, I might do some sightseeing Saturday afternoon and Sunday Morni...

Dressage Training

by sr71plt on Sep 19, 2017
Gay Male

(Written for specific fetish request by SA) "The Hamiltons have asked whether you can go to Lexington with Mr. Hamilton for the Dressage at Lexington competitions in July, Santo. You'd be his groom for the three days there, and if you worked out well, you could stay on helping them here at Ash Creek Farms for the rest of the summer before you go back to s...

Dressing for Larry

by loneguy01 on Jul 11, 2018
Gay Male

I met Larry through a gay web site and had a threesome with him and my friend Justin. Justin lived 50 miles away and it wasn't convenient for us to meet very often. Larry, however, lived in my city. He had mentioned that he would like to meet again and it would turn him on to see me in lingerie. I went on-line and saw images of men in lacy panties, silky sli...

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...

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...

All Dressed Up

by xsbelle on Aug 18, 2017
Gay Male

I tugged lightly at my tie in the elevator, carefully loosening the knot so that it began to show the button at my collar. It looked, I hoped, as if I'd tightened it that morning and then launched myself into a busy day of meetings and firm handshakes. Using both hands to hold my jacket away from my sides, I scanned myself. The shirt I had ironed an hour ago...

Playing Dressup Ch. 01

by mfs1390034 on Jan 21, 2020
Gay Male

"Sure. Why not?" I said and we went upstairs to his parents bedroom. My best friend and I had watched several YouTube videos about men who dressed up in women's clothing and, after helping ourselves to his parents liquor cabinet, we decided it would be fun to try on his mom's clothes. At first we tried on her wraps and coats and had fun drunkenly strutting...

Playing Dressup Ch. 02

by mfs1390034 on Mar 18, 2020
Gay Male

Jeff and I spent the entire week at school without discussing what had happened. How I had dressed up in his mother's clothes, which turned him on so much he asked if he could jerk off to me. How one thing lead to another and, before we knew it, we were jerking off to each other and even tasting each other's pre-cum! I didn't feel wrong about it, I was actua...

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...