Gay Caught Cross Dressing Stories

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First Time in a Long Time

by twotimeloser on Dec 24, 2019
Gay Male

A little about myself. I am a panty wearer. I love everything about women's panties and sexy men's underwear. A few years ago I stumbled upon a very popular app, where members can share photos and began posting pictures of myself in panties and lingerie. I have been identifying myself as bisexual most of my life. But, at 54 years old, it had been since my te...

Winners and Losers Ch. 07

by bawdybloke on Sep 15, 2017
Gay Male

If you have missed the previous instalments the premise of the story is that after a football match, the losing team must provide sexual relief for the victorious players. Previous chapters for Winners and Losers are on Literotica. * * * * * There was no denying that the last minute loss to AFC Kerlon had dented confidence in the dressing room, but when...

Fair Is Fair Ch. 05

by bgdddy_2000 on Sep 18, 2017
Gay Male

This is a story of married men having gay sex and it's pure fiction. If you are offended by this kind of story, read something else. Any inference to actual people is purely coincidence. Since this is not reality, safe sex isn't practiced. In real life, always use condoms and practice safe sex. ***** Here I was on my knees, with hard cocks pressed against...

Becoming a Gal Friday Pt. 03

by Showoff888 on Sep 14, 2017
Gay Male

I just turned twenty, was in a relationship for almost two years to a hot older commanding bitch who was ten years my elder. We had great sex but she left me for an older and richer man. I also lost my job at the law firm were we both worked, probably due to her efforts, I was just an office person there. Now I'm out of a job and have to move out from sleepi...

On the Rebound

by corruptiveInfluences on Sep 14, 2017
Gay Male

I've tried writing several different stories, but have never posted anything before this. So hopefully this is something at least somebody out there enjoys reading as much as I did dreaming up. The usual warnings apply: if you're under 18, or these types of stories are illegal for you to read in your area, then go somewhere else. Otherwise, enjoy. ***** Th...

Passing at Christmas

by sr71plt on Aug 18, 2017
Gay Male

Lord Reginald was receiving an early Christmas present. Lady Caroline and her Oxford student son, Percy, were first-day-of-advent dinner guests at his country home, Morton's Staff, in Hampshire. Lord Reginald couldn't countenance the giggly Lady Caroline normally, but he'd waited for years for the luscious Percy to reach his majority, and Reggie wanted to be...

Keep Me Safe Ch. 03

by miles801801 on Sep 14, 2017
Gay Male

Ryan didn't know what was worse as he sat at the hospital, the screams or the quiet. Miles was unconscious when the paramedics arrived and he didn't regain consciousness until reaching the hospital an hour ago. Then the screaming started. The desperate cries coming from Miles made everyone feel sick. These weren't the usual cries from a hospital patient, th...

Backseat Introduction

by SluttyBisexualGuy on Feb 12, 2019
Gay Male

I can't believe this is happening. So I'm going to write this story as it happens because it's happening to me RIGHT NOW and I'm freaking the fuck out and it's helping me to pretend I'm busy on my phone because holy mother fucking holy shit balls. I'm on a cross-County road trip with my 22-year-old college girlfriend Kelly, and her family. We're travelin...

Long Time, No Suck Ch. 04

by Stontstr on Sep 1, 2017
Gay Male

That weekend was amazing. I felt really great about my relationship with Marc. Cloe, Stephanie's girlfriend, turned out to also have a surprise. See, she turned out to have a rather nice penis, a nice extremely large, uncut penis. Cloe had even named it, Clarence. Marc had to go back to town on business for several days, but Stephanie said he knew all about...

A Natural 'Gurl'

by sexyR2 on Aug 18, 2017
Gay Male

Yes, I know that it has been a few years since I last posted. I was busy. I hope, however, that this new story makes up for the delay. It is in a new category for me, gay male instead of gay female like two of my previous submissions. Enjoy! Debbie, er, sexyR2... ***** Today... When the somewhat urgent knocking came to the door, Debbie knew in an inst...