Gay Caught Crossdressing Stories

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Infinite Scroll

The Mentor

by tc64 on Aug 18, 2017
Gay Male

This is a first attempt at a dual POV story and involves my fantasy about a real person, but names have been changed to prevent getting busted somehow. Be kind. 8 Years Ago Me: I had nothing to do on a Sunday, no games or practices and I had a message from Leslie that her son Joey's club soccer team was playing at the complex near me. Joey played for the...

Punished for Jerking Off

by speedodave on Dec 2, 2019
Gay Male

After leaving high school I did some triathlons and the leg that scared me the most was swimming. I was an OK swimmer but not great and not confident at the kind of distances required in the longer triathlons. So I spent a fair bit of time swim training at the local aquatic center. The pool was a city run center with a fifty meter outdoor olympic sized pool...

Jay and Kip

by Santander on Aug 30, 2017
Gay Male

Jay emerged from the bathroom, a white towel low around his hips. Kip was sprawled on the bed, naked, his cock flopping lazily to one side, his eyes closed. Jay was the shorter and more heavily-built of the two, and though he saw him naked every day, he couldn't help admiring the other's lithe, athletic body. As he approached the bed, Kip's eyes opened, meet...

The Ingram-Lewis Chronicles Pt. 02

by JASONSHOMOEROTICA on Oct 15, 2017
Gay Male

PATRICK INGRAM-LEWIS - OLIVER'S FATHER A Homoerotic Short Story By Jason Land FOREWORD Subsequent to publishing the first story in the chronicles of the Ingram-Lewis family, the present Headmaster of Rigby School, having read the first account, kindly gave me access to documents from the school archives which throw a somewhat different light on the scho...

Boys on a Boat

by Sean Renaud on Aug 18, 2017
Gay Male

"You know this was a good idea buddy. I don't know why the fuck we didn't think to do this years ago." Gene shouted running to the ship's bow and lifting himself up on the railing. He loved the feeling of the crisp sea breeze beating against his face and rifling through his short reddish brown hair. Lance turned his attention from his fishing rod for a mom...

Teasing Another Neighbor

by stockingluvr on Oct 15, 2017
Gay Male

I saw Paul a couple of days later while he was out mowing his lawn and I was just getting home from work. After our night of spectacular but short lived sex in the back yard, Paul seemed a little more talkative. He mentioned that he really enjoyed himself and that he wouldn't mind trying that again. I said that we'll have to try something different as the be...

Finally Meeting Ch. 01

by BedtimeRoutine on May 29, 2018
Gay Male

Hello! This is my first story, so if anyone out there likes it, I would appreciate some feedback! I've been a long time reader of Literotica and finally decided to make a contribution of my own. This story is written in the first person perspective of an early 20s male who finally summoned the courage to meet an older man he met online in the webcam world....

Self Exploration

by tc64 on Aug 18, 2017
Gay Male

How long have I been bisexual? Good question. For as long as I can remember, my fascination with sex involved both genders. My actual experiences as a youth, however, always involved girls, women, whatever, the female of the species. There was always a part of me that focused on the men when viewing porn. Was I projecting myself into their role, imagining my...

Four Weddings 01: The Uncle

by WilliamGuppy on Mar 2, 2020
Gay Male

This is one of a set of four 750-word stories, each told from the perspective of a different wedding guest. The order: Uncle, Groomsman, Aunt, Waitress. The first two are Gay Male and self-contained. The last pair are Lesbian and are also self-contained. My wife and I prefer young lovers. For this, weddings are perfect. Young. Impressionable. Aglow with rom...

Chauffeur The Ch. 03

by skinnysailor on Sep 14, 2020
Gay Male

"See it there? The dock? Look up the path and you can just see the red roof." With that the pilot banked the DHC Beaver float plane, circling the lake, checking for boats and the wind direction. He throttled the big Prat and Whitney radial engine back, lowered the nose and the flaps, and down we went. We'd been up since before dawn, loading Mr Nash's Linco...