Gay Caught Cross Dressing Stories

11,656 results
Orientation
Length
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Infinite Scroll

Knock on the Door

by alexcarr on Aug 18, 2017
Gay Male

"So it's you again, wanting your fix again I 'spose, Jerry?" "How did you guess," I asked like I was trying to be cool, all the while thinking no way will he let me into his life again. Thing is, - well okay I did dump Danny a year ago, it happens, - sometimes a guy needs to move on, search fields anew, thing is the field I searched did not bear oats - it w...

Rye's Encounters Pt. 01

by sissyrye on Dec 23, 2019
Gay Male

Note to reader: The following series of encounters are 100% non-fiction, best of my ability accounts of my real life encounters with horny men. Names, locations, and revealing details were altered to protect identities of course. PREFACE: Hi. My name is Rye. I am a cute, 5'9", blonde, big booty, white boy...with a hunger. I have a fairly symmetrical face...

Taking the Neighbor Ch. 09

by jjdtx on Apr 30, 2018
Gay Male

Allen came downstairs from taking his shower, he was naked and reached for his shorts. "Wait," I said, "You won't be wearing those." I beckoned him over to me, I placed a cock ring around his cock and balls, snapped it into place. "I love these!" He said, as I stroked his hard cock. I then handed him a t-shirt, plain, black, with no logos or emblems. He...

SynerGism

by assxible on Aug 18, 2017
Gay Male

I've been on the business end of several cocks, from short skinny little rascals that barely tickled, through the average sized that served quite adequately, to a few beefy rams that were painful and threatened to split me in half. Truly, size does matter. But several factors other than cock size matter just as much for sex to be considered phenomenal. Once...

My New Career in Modeling

by niplock on Sep 14, 2017
Gay Male

This story is about a time in my life when my financial situation had taken a severe turn for the worse. I was 35 years old and had just gone through a nasty divorce. My then wife was always looking for attention from other men. She needed them to tell how beautiful she was and was constantly searching for compliments. It got so bad that she started to give...

Just A Lift!

by Scotsdude on Aug 18, 2017
Gay Male

This story is complete fiction…but fun I hope! "Not going mate. Soz." Kevin said. I was well pissed off. "Why the hell not?" I asked. "I can't afford the tickets." Great, so that was that. Creamfields for me was off too! Kevin was the one with the car, I was the one paying the fuel, but now Kevin wasn't going, I couldn't get there! "Mate, you can always...

Halloween Rabbit Holes

by hornyyoungboylovesolder on Jan 15, 2019
Gay Male

I had seen some men, one man many times, and was having a lot of fun. The one guy I was seeing constantly was 58 a bit of a belly, but an amazing cock. After a bit he had gotten me into cross dressing. It started with panties. Then stockings and heels. Leading to bras, skirts, and wigs. Eventually I was putting on make up, eye lashes, lipstick, the whole nin...

From Straight To Slightly Bent h. 02

by Akito01 on Aug 18, 2017
Gay Male

My decision to continue the affair is not a clear cut one. In the past, I never would have considered myself the sort of person who would cheat on their mate. On the other hand, I continued to play out the events of our first night together in my head, and all the things that I could still yet do to you... In the end, I knew I had to have you again. The f...

Jeans

by whineluvr on Oct 15, 2017
Gay Male

I was a college student; I forget the year but a student nonetheless. I was tall, lean and lanky and generally regarded as attractive by both sexes. This was back in the disco era before AIDS when sexual ambiguity and promiscuity were at there height. Late one afternoon, I wandered into a small men's store intent on purchasing a new pair of jeans. There wer...

Silk House Pt. 01

by jaiunus on Mar 12, 2019
Gay Male

Author's Note: This story is all about spandex and focuses a lot on the "dressing up" portion of play, as it is the author's favorite. Just a heads up. Happy reading! ***** There were two things I was absolute certain about myself when it came to my personal sexual pleasure. One was that I had an incurable desire to wear, see, and feel spandex. That much...