Gay Caught Cross Dressing Stories

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Pull Toy Ch. 01

by thick_eight on Aug 18, 2017
Gay Male

pt.1 Seduction The beginning of the summer in 1962, I was 18, living in a small town between Ft. Lauderdale and Miami. As usual I was by myself, which was nothing new, considering I had been raised in the military, and was used to not having many friends, being the "new guy" all the time. I had decided that I wanted to get on the swim team, and I had the w...

Slut Scout

by Michele G on Sep 14, 2017
Gay Male

Our neighbors have a really good-looking son," Chad. His room is up in the attic of their house like mine is. Every now and then I see him in his window and he's seen me from his. He knows all about me and is cool about my cross-dressing. I see him with a lot of pretty girls. Sometimes I catch him sneaking them up to his room. The girls can get pretty loud a...

Bonds Unbroken Ch. 04

by Cia81 on Sep 19, 2017
Gay Male

The next day brought little change to Natham's condition. He was still heavily medicated but had stopped hissing at the staff and let them touch him in order to help him without being sedated. I sat with him for a few hours. He kept waking up when I shifted but after a quick check to make sure I was still there, he would knead my hand caught between his, pur...

New Neighbor Ch. 01

by theilluminaughty on Sep 14, 2017
Gay Male

Hey guys. This is a story containing mpreg, fantasy creatures, cross-dressing, and more. You can suggest more tags, and such. There's some guys with pussies and tits. If you don't like it, don't read it. ______________________________ It was fall of 2500. In a city called Colt, on a planet much like earth, except the size of the sun, orbiting a much large...

Rick Needed a Beer, Gets Much More Pt. 11

by Iwanttwo on Aug 12, 2019
Gay Male

This chapter may better fit in the cross dressing category, but I'm keeping it in Gay, as past and future chapters are gay stories. And this chapter does involve some hot gay sex. I recommend you read previous chapters first, if you haven't already, to understand the characters. —————————————————— Tuesday at the office was awkward, to say the least. I avo...

I Thought I Wanted It Rough... Ch. 02

by LonelyVirgin on Sep 14, 2017
Gay Male

I had just been fucked for the first time. I couldn't believe what I had just done. Some stranger had just used my ass for their own pleasure. Someone had stuck their dick INSIDE me. What was I doing? What kind of slut would do something like this? I didn't even know this guy, and I agreed to meet him, and let him pound my virgin hole. Before I had made up...

Our Preference for Black Pt. 02

by eviltwin52 on Sep 19, 2017
Gay Male

This is dedicated to the all anonymous commenters. Bring on the hating... and then go fuck yourselves. LOL. ***** Our role reversals had come about quickly. Surprisingly, it didn't bother me that in our small town it became public knowledge that Cheryl had a black lover and that I was more than accepting of it. That so many people who once respected me, no...

The Joy of Submitting

by loneguy01 on Aug 21, 2019
Gay Male

I had recently answered an ad seeking a submissive cocksucker. I am a total bottom and had experimented with cross-dressing but never really got into the dom-sub thing. However, the ad intrigued me and I submitted myself to a hung black man in his hotel room. The experience was exhilarating and I yearned for more despite being apprehensive about the possible...

Cheating on Our Wives

by StephanieSeymour93 on Jul 15, 2020
Gay Male

The moment my cock slipped inside his asshole I knew it was the real deal. We were going bareback. Neither of us gave a fuck, and we were both married anyway, so the risk was low. He was on his stomach on the bed where he fucked his wife a night earlier. Now it was my turn, and I wasn't holding anything back. I was on top, pumping him. He wore his wife's lac...

I am not a slut, yet!

by stevensinner on Apr 21, 2020
Gay Male

I typically buy my marijuana from Dennis, my friends much older, gay uncle but this day he wasn't home or answering his phone. I knew that his neighbor, Greg, sold weed for him sometimes so despite not knowing him well I went to his door and knocked. "How can I help you?" Greg asked while sizing me up. I am a very petite, 18-year-old male at only 115 poun...