Gay Caught Cross Dressing Stories

11,656 results
Orientation
Length
Source
Infinite Scroll

Five in One Night

by jordan80 on Aug 18, 2017
Gay Male

When I walk into the bar there are only a handful of people inside. The bartender gives me a grin and a nod; guess that happens when you're a regular. The waitress comes over to take my order and I admire her uniform. This place is attached to a very nice hotel, so the waitress's uniform is a cross between professional and slutty. For some reason, that turns...

Pony Boy Ch. 04

by ChestersBoi on Sep 14, 2017
Gay Male

This is the fourth chapter of 'Pony Boy' and, if you haven't read the rest, then please do so first. Quite a bit of the story refers back to events in the earlier parts and it won't make much sense if you read them out of order. And, of course, there are the usual disclaimers; anyone involved in sexual acts is over eighteen and we're all fictional. There'...

I Make Believe I'm a Cuckold Ch. 04

by donaldelliott11 on Feb 10, 2020
Gay Male

This is the fourth and final chapter. You should read the others first. This chapter contains a scene of incest between two adults. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help me improve my writing; ratings help other readers find what they most will enjoy reading. Ra...

Cross-Country with My Uncle Ch. 09

by John Hill on Sep 14, 2017
Gay Male

Mikey, a studly 18-year old finds himself intimate for the first time with Mike, his namesake 24-year old uncle whom he's idolized all his life during a cross-country drive. Steve is the 20-year old collegiate gymnast who hitches a ride with them. As he lay between my legs, Steve and I were still grasping each other's arms. His arms were extended over his h...

Castaway Love Ch. 01

by kwchancellor on Oct 29, 2018
Gay Male

I awoke to the sound of a roaring I couldn't place and a pounding headache. Forcing my eyes open, I saw blue, a deep sky blue. I turned my head to the left and saw a row of thick mangroves and palm trees. To the right I saw the ocean crashing on the shore. I was on a beach. Sitting up, the world tilted, and I was hit with a wave like dizziness that threw me...

Zius

by Scotsdude on Aug 18, 2017
Gay Male

Year: 2084 "There is still much talk over who will win the next General Election on the planet Zius." The EBC reporter announced. "The current Zius government feels they could lose to the Global League, who already control the planet Reid and IO. Should this be the case, then they could end up imposing a Feudal status on the planet as has happened on others...

Rick Needed a Beer, Gets Much More Pt. 12

by Iwanttwo on Sep 23, 2019
Gay Male

I was awakened by the rough landing and was surprised I had slept through the entire flight. I was glad I had all my gear in one carryon bag and headed straight to the rental car desk after getting off the plane. I rented an average rental as I wanted to have a low profile and keep to myself this week. After checking in, I looked around the hotel. It had a n...

We Meet Eventually Ch. 09

by 1suitedbi on Sep 23, 2019
Gay Male

We meet eventually This is a multi part story that contains MM, MF, and MMF sex. Chapter 9 -- Monday Morning Back to work for Alex and an unexpected interview. I went through my usual routine in the bathroom before heading for the dressing room, slipping on a pair of tight lace sheer pink boxers, enjoying the firmness around my cock and balls of th...

An Old Friend Ch. 02

by jjdtx on Sep 14, 2017
Gay Male

Chapter 2 – The Next Day The next morning, Joe left early for work and I didn't have an appointment until late in the day. So, I lounged around, looking at his DVD collection. In a small box, I found his porn stash. It was a nice selection of compilation DVD's. About twenty in all, most were straight cum shot movies, but there were four bi movies. All were...

Bathhouse Observations

by glory_first on May 12, 2020
Gay Male

The baths are undoubtedly the easiest place in a city to have male group sex, after allowing for individual circumstances during any single trip. After more than a hundred visits over the last few years, basically all of them involving satisfying sex with other men, often writing about the experiences afterwards, leads to a few general observations. Visitin...