Gay Accidental Crossdressing Stories

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Out of Uniform Ch. 03

by gustavca on Sep 15, 2017
Gay Male

I awoke well rested and refreshed after a short but deep sleep. I reflected back on the previous day's adventures and regretted nothing. In fact, I was feeling very comfortable with myself as I prepared for my day. After taking command I developed a routine I called 'My Patrols'; the crew apparently referred to it as the 'Captain's Prowls'. My Patrols, one...

Accidental Cocksucker

by silkstockingslover on Sep 25, 2017
Gay Male

THANKS: To Robert, goamz86 and MAB7991 for editing. ***** Sometime after ten o'clock, following a late administrator's meeting about next year's school year, I pulled into a truck stop that I drove past every day but had never stopped at and went directly to the restroom...barely able to keep from pissing myself...still half an hour from home. I walked...

An Accidental Public Performance

by Giganet on Aug 18, 2017
Gay Male

This occurred a year, maybe two, before I met Paul, who will be introduced in coming stories. I was 18 or 19 at the time, so, it all happened quite some time ago. I was in college taking Business Administration, for what would ultimately turn out to be my last semester. I was a dishwasher at a local mall restaurant to pay the bills at the time. There was...

My First Experience - the Cinema

by AlanDavis767 on Dec 9, 2017
Gay Male

The story, or I should say experience, that I am about to tell you about occurred many years ago, when I was 18 to be precise. I was a young, fit, good looking lad with dark wavy hair and a sporty physique from playing many hours of football and cricket. At the time I was relatively inexperienced sexually, although had had a few very exciting gropes and fumb...

A Long, Long Time Ago

by OhioCurious on Aug 18, 2017
Gay Male

These real events took place a little over 30 years ago, while both my wife and I were college students. * We had married young. I was 21, she 18, and both of us had very limited sexual experience. Penthouse Forum was our ticket to erotic fantasy and the air was full of sexuality. We spent our weekends like most college students, hanging out with friends,...

Bill Finds It Never Too Late

by noody2005 on Sep 14, 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. As I pulled it through he cli...

The Hapless Detective

by idsweaterguy on Sep 16, 2017
Gay Male

Chapter 1: I parked my car four houses down from the house the man I was following had parked in front. I watched the middle-aged man who was about six-two and wearing a brown fleece jacket, jeans and a brown baseball cap get out of his car, throw a backpack over his shoulder and walk up to the front door of the non-descript but rather large house in a newe...

Exploring my Sexuality Ch. 02

by alexis19901 on Jun 2, 2020
Gay Male

Just a quick recap from the first chapter. I'd made my first trip to a sauna, lost my virginity, got spit-roasted and then another guy came in my ass all before I left. The last guy left me his number and I just couldn't resist. This story will contain some crossdressing. I'd gone back to my normal life for a number of weeks since my trip to the sauna. Havi...

Awkward Reunion

by xrydog on Oct 31, 2018
Gay Male

I don't think I am that unusual. That is, not that unusual before my accidental encounter with a high school acquaintance turned my life upside down. I am married, fit guy, in my mid-thirties. At just a tad under five foot eight and 155 pounds, I have a slight build. I am a naturally hairless and smooth guy. I always considered myself straight but have als...

How it Happened

by loverofintersex1 on Sep 14, 2017
Gay Male

This is a fictive tale, and any resemblance to anyone outside of it is purely accidental. Do not read any further if you are not of legal age in your jurisdiction. ***** I was supposed to suck his cock and then butt-fuck him, so we'd arranged, or I thought we had, but in between making out he rolled me over and got on top, his weight pressing me down, legs...