Gay Accidental Crossdressing Stories

315 results
Orientation
Length
Source
Infinite Scroll

Perfect Stranger

by isadore on Aug 18, 2017
Gay Male

I met him in an online chat room and within 20 minutes we were telling each other our deepest secrets and which way we preferred to get or give sex. I think it was my suggestion to go over to his place, but he was not against the idea and before you knew it I was scribbling his address and door code on the pad next to the computer. It took me all of 10 min...

My First Male Massage

by HerLittlePiggy on Sep 14, 2017
Gay Male

I closed my eyes and tried to relax as I lay face down on the massage table with only a sheet covering my bare naked ass. The masseuse's strong hands felt amazing as he kneaded my tired flesh but my mind reeled as I struggled with the strange primal desires dancing within me. I had never in my life entertained a gay thought but his hands felt so good and ero...

My First Time

by K_Martini on Sep 14, 2017
Gay Male

I can't remember when it first happened. When it changed from me just going out for a beer with him, to me noticing the way his hands wrapped around the bottle, the way his tongue flicked the rim before sucking in a long, cold swig of beer. When it changed from standing on the deck smoking a cigarette, to me fixating on how his lips wrapped around the filter...

Internet Holiday

by Sean943 on Jan 20, 2020
Gay Male

My current assignment in Den Haag was nearing completion, time to look for a new assignment; first, I would take a few weeks off. Where would I go, what would I do when I got there. Being a solo traveller has its restrictions. Checking out options on the web, I came across someone looking to share a cabin on a cruise ship. I sent him an email saying, I was p...

Overnight: GM2

by JimBob44 on Sep 14, 2017
Gay Male

*Author's note: Any and all persons engaging in any sexual activity are at least eighteen years of age. Disclaimers: Yes I need an editor; no, I do not want an editor. Yes there's too many people to keep track of, yes it jumps around too much, yes it's too long, yes it's too short, yes it's in the wrong category, yes it is stupid shit, and yes, I am a horri...

Never Too Old!

by noody2005 on Aug 18, 2017
Gay Male

Joe who had moved next door to us about three months ago asked if I could help him with running a cable in his loft whist our wives went shopping. The day was hot and I was wearing an old coverall, the heat in the loft was so intense that I stripped to my briefs before inching my way to where Joe was pushing through the cable. I moved to the other end of the...

Stephen

by hornygemini87 on Aug 18, 2017
Gay Male

As a kid, I was effeminate and people bullied me for being me, gay. I didn't have any concept of "gay" until I reached my teens and realized what being gay meant. I decided I wasn't like that, so I tried to act straight and toughen myself up. I also tried bulking up some muscle, but that was just not what I was made of. I remained slim, but I tried so hard t...

Southern Magic Ch. 04

by PhoenixKing on Sep 14, 2017
Gay Male

We were at our spot, the Space Needle, this time making sure to stay well away from the edge. I was lying in between Nate's legs, his arms around me, enjoying one of those rare days where the sun warms your skin and the breeze flutters through your hair. In this moment I knew what life was supposed to be like. I once read a quote that said that humans weren...

A Night at the Pub

by VeryCuriousIan on Mar 9, 2020
Gay Male

Adam lived in a respectable suburban avenue, quiet but for the kids playing football in the street. His mum was downstairs, banging away in the kitchen and his dad was talking football outside with the neighbor. He peered out as they both gesticulated about the last game, Mr. Mitchell from two doors down. After his taxi experience, and to be honest a few m...

The Train Ride

by ScotishGuy on Aug 18, 2017
Gay Male

23:50hrs. The overhead display was showing the expected time of departure so, no delays. I was standing at London Euston station with five minutes to spare. I looked around for one of the customer service people, wondering where the platform was. Pointed in the right direction, I picked up my bag and dashed along the platform. I walked up the carriages, loo...