Gay Accidental Crossdressing Stories

315 results
Orientation
Length
Source
Infinite Scroll

Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...

Exploring My Bi Side Ch. 02

by bscurious1 on Oct 19, 2020
Gay Male

Randy and I kept up our meetings, sometimes weekly sometimes two or three times a week, just depended on our schedule and how horny either of us were. We always met at his house in his home studio which offered us a lot more privacy and freedom. As I had stated the massages pretty much stopped but he would still give me one when I needed one or just wanted o...

My Gay Crossdressing Vacation Ch. 04

by Flame666 on May 11, 2020
Gay Male

I slowly opened my eyes, remembering what had just happened over the past 24 hours, I woke up looked at the time, it was just before 7 pm. Earlier I had decided to start getting ready for my date with Paul and John around 7:30 so I got out of bed to get started. I was going to start with a shower and because I had a bit of extra time decided to take off my b...

I Once Was Lost But Now Am Found Pt. 02

by eviltwin52 on Oct 5, 2020
Gay Male

In Part 1 I found a friend in Leon. Having lived the greater part of my life alone, maintaining my bond with Leon was the most important mission I'd ever had. Sucking his cock was my way of showing him my appreciation for his comradery. He didn't ask me to do that. He didn't tell me to do that for him either. All Leon did was nudge me in the right direction....

The Evan Fantasy

by SilkyDave on Oct 15, 2017
Gay Male

Years of Private Messages and e-mails where I always back down out of fear. My fantasies of a male to male encounter were often over powering. I finally worked up the courage to climb off the fence and take control of my fantasy. I contacted Evan and told him I would be at the mall in Braintree at noon, wearing jeans, flip flops, and a white button down shi...

My Dream Solution Ch. 01

by Cyanlot on Sep 15, 2017
Gay Male

[Note: This is a long introductory setup to a multi-part story. There is *no* explicit sex in this first chapter. If you are looking for quick, hot read, move on. This is not it. Things will heat up in later chapters, I promise. --Cyanlot] Chapter 1: When I Hit the "Change of Life" When Massachusetts became the first state to legalize gay marriage, Todd a...

Bathhouse Observations Ch. 02

by glory_first on Jun 9, 2020
Gay Male

Bathhouses are places with thousands of years of history, yet are extremely easy not to notice, unless someone is looking. That such places have existed is common enough knowledge, whether awareness of Roman decadence or when reading about certain Middle Eastern baths intended for men only. When there is a place where naked men can enjoy having anonymous sex...

Moving Day Memories

by jordongeff on Sep 14, 2017
Gay Male

(...father-in-law-confidential - Prequel) As with most works of fiction, there is plenty of real life experience blended into this story. This actually happened - up to a point... Enjoy. -GJ ---------------- I had boxed up everything in my three room basement apartment and was waiting patiently for my father-in-law Edward to arrive with his pickup truck....

Just a Game Ch. 02

by tamgreen on Sep 14, 2017
Gay Male

Pete woke up alone, and the apartment smelled amazing--something delicious was cooking. He tottered unsteadily to his feet and looked down at himself. He was wearing nothing but a t-shirt and a furious hard-on. He pulled on a clean pair of boxers, stuffing himself awkwardly into the fabric tent before trudging to the kitchen. Dean was standing at the stove n...

James Goes Sledding Naked Pt. 02

by sweetcobs84 on May 7, 2019
Gay Male

I punched in the combination for the side entrance. I contemplated taking the elevator up to my third floor room but thought it might be a bit too risky not knowing who might be on the other side of the elevator doors when they opened. So, instead, I walked up the side staircase. I got up the three flights without being seen, but as I opened the fire door to...