Gay Accidental Crossdressing Stories

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Tickling the Ivories with Derek

by alexcarr on Aug 18, 2017
Gay Male

Following the footsteps of my father I wanted to learn how to play piano. But attending a tutor's class turned out to be a lot more than tickling the ivories! I guess it didn't take me long to realize Derek aimed to show me more than just how to play a piano. It was just the way he'd close up behind me and extended his arms each side of me as I sat on the p...

Surf's Up

by FloridaSmoothie on Aug 18, 2017
Gay Male

Far from being my masturbation biography, this is how I started masturbating with other men. The first time I even thought of masturbating with another male was some years ago, at age 33. It started with my visiting nude beaches, first when on business trips to California, then at beaches in Florida, where I live. With my first accidental visit to Blacks B...

A Much Needed Vacation

by DictionDoctor on Aug 18, 2017
Gay Male

"Life is the great indulgence - death, the great abstinence. Therefore, make the most of Life – here and now." – Anton LaVey Chapter one| Jay closed one of his favorite books, a book read so many times over the corner of a majority of the yellowed pages went forward with evidence of many a bookmarking. The weight of the paper book felt good against his th...

Cocksucker: Cocksucking Training

by silkstockingslover on Sep 14, 2017
Gay Male

Summary: A twink teaches a straight man how to suck cock properly. Note 1: Thanks to goamz86, Robert and MAB7991 for editing this story. You do not need to read the first part to enjoy this story. In case you are curious, here is a brief summary of part one called "Cocksucker": Chris, a married straight man, is stuck at the airport when his flight is d...

A Real Bathhouse Slut is Made

by Danmo1 on Sep 16, 2017
Gay Male

This true account of the activities of a mature 50'ish guy continues from my first time at a bathhouse entitled The Making of a Real Bathhouse Slut. As I drove home from the bathhouse the first week I had a hundred different things going through my head, one of which was guilt. I quickly realized that after years of no sex with my wife there was really noth...

A Slut is Born

by Luvsishyp on Apr 21, 2020
Gay Male

Special Thanks to madam_tasha for amazing editing and assistance. I sat on the motel bed feeling a nervous excitement. "This will do just fine," I thought to myself, as I looked around the cheap, seedy room. It was relatively clean but had definitely seen better days. The carpet, an ugly pale green, was worn and faded from years of use. An oddly patterned...

Risky Business

by XxPrinceAnonomousxX on Dec 9, 2017
Gay Male

Damien knew that it was risky business to play with his lover, he knew that Scottie wasn't one who could take it for a joke but he couldn't help himself. Damien couldn't help but love the fact that he could turn on his boy so easily. Damien found himself getting a little too close to the boy, making the younger man's breath hitch momentarily, and then backin...

Exploring my Sexuality

by alexis19901 on May 12, 2020
Gay Male

I'll just start by saying that I've never attended any sauna that may get mentioned in the story. No names that are mentioned are real people either. It's something I've purely put together based on fantasy alone. Thanks for reading! Today was finally the day. I'd been waiting months to go and push myself to try the closest sauna to me which was a short tr...

How Did I Get Here

by bart_allen on Oct 15, 2017
Gay Male

I found Wendy on OKCupid. She was just another face as I scrolled down, albeit a fairly attractive one. I clicked on her profile, glancing over it: she was older than me, which is not usually my type, and she was six years older than I at thirty two. She had a darker natural red hair in shoulder length cut, but a sort of light olive complexion, and pouty lip...

Bathhouse Heaven Ch. 32

by glory_first on Aug 22, 2018
Gay Male

The bathhouse was fairly empty this Wednesday afternoon, a reminder of different rhythms from the past. Following the familiar routine, today with more space to undress than the case lately. The beer was quenchingly cool, and quickly finished. Going upstairs, I walked towards the sling room, noticing a couple of men going different ways than my path. How...