Gay Caught Crossdressing Stories

10,182 results
Orientation
Length
Source
Infinite Scroll

Pony Boy Ch. 05

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. Enjoy...

Failing Upward Ch. 14

by el_wing on Sep 14, 2017
Gay Male

I woke from a nightmare, finding myself wound up tight in the sheets-- one of those bad dreams where your own cries wake you. Les knocked at my door, asking if I was all right. I kicked the sheets, uncoiling my body, and told him I was fine. "To see the world in a grain of sand," I said to myself. I knew what that meant now. William Blake was right. God a...

Aquata Cove Ch. 76

by Feare909 on Sep 14, 2017
Gay Male

Chapter 76: Gain And Loss The surface explodes from the outside as Merrick sinks, holding Arnaav close in his arms. His body changes as his flesh formed into an array of beautiful blue and silver scales, along with wavering fins along his tail. Arnaav holds onto Merrick as his body breaks out in velvet fuzz of cream and mocha colors. The boy peers around...

Trip with Friends Ch. 01

by TheCandyManCan13 on Sep 14, 2017
Gay Male

My name is Jon Grossmann. Despite what you might think, I am not Jewish. At least, not ethnically. Maybe way back when someone in my family was, but no one in my family is anymore. Nope, just regular old uncertain European ancestry, like most North American white people. Anyways, not really trying to make this about race or anything, just making sure you wer...

Fucking Her Boss Up Right

by quutoo on Aug 18, 2017
Gay Male

Debby was carrying some folders to her boss, Jerry Walker. It was close to quiting time and she was anxious to get home to her husband, Craig. They both got home about the same time and in the length of time that it took them to strew their clothes across the living room, they were locked in a loving embrace. Last night they only made it to the hallway leadi...

Fingering the Idol

by Cruel2BKind on Aug 18, 2017
Gay Male

*Normally I get the idea for one of my stories from a show, a movie, a book, or a game. The Bottom Tier series was influenced by 'The Windup Girl', Alone at the End of the World was influenced by 'The Walking Dead'. Slave Boy=Skyrim, Eyes Like Winona=Twist, etc. This is the first time however, that I got a story idea from a session of D&D. This is a one-sho...

Fetish Galore

by sr71plt on Aug 18, 2017
Gay Male

I had been banished. My wife would be joining me in a couple of months, but I was sent ahead—banished from New York—for my transgressions. April's father had known I was bi before he bought me for her daughter—and he also knew how I made my living, because he had been paying April's bills. But I suppose he assumed I would put all of that behind me when we we...

Kasper's Den Ch. 09

by tarzanacide on Sep 19, 2017
Gay Male

[I've been searching in the woods and high upon the hills Just to find my samurai Someone who won't regret, to keep me in his net Yes I need my samurai] +{Kasper's Den}+ Part 9 [By Emri and Xelos] I accidentally saw something I wasn't supposed to see. Amir had left early for class. He wanted to get some things done so he could be back in time to tak...

Bending the Straight and Narrow Ch. 02

by markindy on Sep 14, 2017
Gay Male

+++++++++++++++ Reading the first part of this story is highly recommended. This story is primarily about homosexual play between married men with understanding wives. There is a small amount of heterosexual content, but it still seemed best suited to the "gay male" category. +++++++++++++++ The college years were easily some of the most fondly remember...

Shooting Matt Ch. 17

by Turbidus on Sep 14, 2017
Gay Male

The action shifts back to Liam and Matt at the resort and stories are shared. There's sex, story, then sex. I'm worried the ratio of sex/story is off. I understand if some of you are like, "back to the cock, dude, seriously". If you're in that group, after the first section of sex, which is marked by a double row of "***", you can skip down to the next doub...