Gay Caught Cross Dressing Stories

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Top or Bottom Ch. 01

by sandyvalleylad on Aug 30, 2017
Gay Male

MWM 7" Cut Looking for c/d Top Those seven words in a personal ad in our local gay/lesbian weekly got me thinking about what I wanted in my sex life. I've been married, dated a woman and am now married again but I've never tried having sex with a man. Hell I didn't even know the lingo -- what's a MWM and is a Top the person who's on top? I needed to underst...

Anonymous Dick

by dixeenormous on Sep 14, 2017
Gay Male

If we met at the pub or a ballgame, I think you wouldn't think twice about me. Maybe a "seems like a nice chap" or "he really likes his sport" but nothing memorable, nothing of substance. A regular guy, with an ever diminishing hairline, not in bad shape but certainly not a gym rat, probably the quintessential definition of average. My job is regular, I'm...

How I Became a Sissy Slut

by DixeenormousToo on Sep 15, 2017
Gay Male

I wish I knew I had these sissy urges when I was younger. Who knows, instead of getting married, having kids, and living the "American Dream," I might have discovered hormones, worked my body into shape, and become a tranny porn star. After all, how often does the American Dream really work out anyway? I'm unhappily divorced, my oldest is on his 6th year of...

The Dressing Room

by Radames on Aug 18, 2017
Gay Male

I had a late lunch hour and decided to spend it at the mall. While wandering through the big department store, I found a display of 'European-style trunk' underwear. They were something like boxer-briefs but with short-short legs. The trunks reminded me of the bathing suit Daniel Craig wore in the latest James Bond movie, but this was definitely underwear, n...

My Boss and Master Ch. 02

by MitchCapslock on Sep 14, 2017
Gay Male

All comments or criticism welcome. New rules, new life The message light was already blinking when I got to my desk Tuesday morning. "Mitch, this is Wendy. Mr. Compton asked that I remind you of your 4 p.m. meeting this afternoon in his office." Forget? It was all I had thought of since I left his office, the taste of his cum coating my throat. It was...

The Storeman

by starova on Aug 18, 2017
Gay Male

Three months after I qualified as a sports physiotherapist/masseur, I started my own practice at home until I could find work with a sports club or association. I was enjoying a quiet coffee in the café and reading the daily paper when my mobile phone rang. A man's voice enquired about the possibility of getting a massage. He had been working an early shift...

Putting Myself Through College Ch. 09

by RobXXX on Aug 31, 2017
Gay Male

My Spring Break assignments were not finished, just my time pretending to be someone I was not, well at least the sex I was not. I received a call from Kevin the day after the cross dressing assignment, he apologized a little bit for the previous day, then jumped right back into work. That night he had another client for me, this one he said was a known cl...

Halos and Heroes Ch. 13

by WasAlmostFamous on Jul 16, 2019
Gay Male

Thank you all who have been reading and following along. I always appreciate getting feedback. It helps with becoming a better writer and it's always an ego boost, so feel free to reach out. I will always respond! The usual spiel: This isn't a stroke story, (more porn with plot.) Be warned, it's very long. 33+ chapters, and many sexless ones to come before...

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...

Maraschino & a Muse's Cherry

by soupwarsproject on Aug 18, 2017
Gay Male

My boyfriend is going to cheat on me tonight. I just know it. He’s such a whore. Lobo claims that he’s only going to try to get his high school pal to do a little figure modeling. I know better. He’s normally not interested in women at all. However, he’s told me before that he doesn’t really consider her a mere woman, but his ultimate muse. I’m certain that...