Gay Tights Crossdress Stories

168 results
Orientation
Length
Source
Infinite Scroll

Bi Man's Bathhouse Adventure

by nubianjock on Jul 3, 2018
Gay Male

I was on a business trip to Cleveland got into town late on a Monday night. The condo I arranged to stay in through my favorite home share website was easy to find from the Amtrak station, which was a short 15 minute cab ride drive. After settling into a really great, modernized apartment downtown with large floor to ceiling windows overlooking a busy strip...

Cock-Sucker: Slut Tales

by tristantrotsky on Dec 24, 2019
Gay Male

COCK-SUCKER: SLUT TALES PAYMENT IN KIND (MY CONFESSION) Did you ever wake up in the morning feeling tousled and hung-over, only to find blobs of drying cum in your hair, and not remember where - or who, it had come from? Grab a coffee and slump down on the chair. Fuck... you look a mess. Think. Think back to last night. Yes, you get dressed up in all you...

Sex Mercenary Ch. 02

by KittyAshleyy on Mar 12, 2019
Gay Male

After accepting the Underworlds job offer I packed all of my belongings in a medium case and dressed in a white crop top, ripped skinny jeans on top of newer fishnet tights (all of the holes the right size), my black leather jacket and my boots. "How do I look?" I asked the Underworlder in the suit. He simply nodded and we left my room. Outside was a blac...

Pounded by my Lecturer

by atera on Sep 26, 2017
Gay Male

From my very first lecture at university, I instantly knew I wanted Mark. Then again, nearly everybody did. He was stereotypically good looking: 6ft 2, dark and toned. He was also my contract law lecturer. Forbidden fruit. I could never pay attention in his classes, I'd be focusing on anything but him to keep my cock from being rock hard and causing embarras...

Gym Submission Ch. 02

by AltErik on Sep 16, 2017
Gay Male

************ Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-) This story contains Male/Male sex, Male/Female sex and Dominant/Submissive themes, so if this is a problem . . . wave off! This story is fictional story based on a fantasy of mine. While it is fiction, I did...

First Time by Candlelight

by Richard963 on Aug 18, 2017
Gay Male

There is a first time for everything in life. The experience of having sex in one form or another is such enjoyment that one never forgets it. So it was with my sex life. I was born in 1954 to an unmarried mother. She tried to bring me up by herself and I remember her as loving mum but when I had to go to school she could not afford to clothe me so I was fos...

MMF First Time

by Erotic Celt on Aug 18, 2017
Gay Male

From the moment I arrived I knew I was in for a treat. A sexual experience that would last with me forever. Janet had always been a sexual dynamo, and she could never get enough sex and was always trying out new things. I had only been going out with Janet for six months, and I already felt incredibly relaxed with her. Sometimes, I found, it could take years...

Rex's Horny Halloween Pt. 02

by TeamCravings on Dec 12, 2018
Gay Male

Handsome Rex Davenport soaked his fit six-foot body in a nearly full tub just before having to get ready for work. It was Halloween and this ginger-haired 40 year-old had a fascinating evening ahead of him. This special night had all been suggested and planned by his dear sex mentor Lorna, a hot MILF who had launched herself headlong into his life in just a...

Costume in a Costume

by MVP6 on Jun 15, 2020
Gay Male

It all began three years ago, in October. I remember because my wife was visiting her sick mother for an extended period of time. Feeling unusually alone and commonly horny I had too much time on my hands to consider the most satisfying ways to shoot jizz. After many lonely nights of jerking off I reflected on the odd realization that many of my fantasie...

Tales of Jason Ch. 05

by Bjsroxxs on Oct 6, 2020
Gay Male

Chapter 5: Lady Daphne When Khauther, Jake and I got to House Achilles, I decided to stay over in Khauther's room. We didn't have sex, we just talked some more and got to know one each other more. When it was time for shut eye, we just slept together in the same bed. He wasn't bothered by it. The next morning, the sun was trying to break into the room thr...