Gay Crossdressers Stories

22 results
Orientation
Length
Source
Infinite Scroll

The Warden and his Captive

by levyn on Aug 22, 2017
Gay Male

{Disclaimer: this story contains a transitioned ftm - female-to-male gay character. However, it's not classified under "Transsexuals and Crossdressers", as the author sees this as a gay erotica story regardless. If this does not suit your tastes, please do not read further. If you -do-, enjoy yourself! ] ( He had been waiting there all night. T...

Shipwrecked with My Buddy Ch. 01-03

by KinkPenguin on Sep 14, 2017
Gay Male

From the Author: Hello reader! I'm a long time reader of literotica, but have never created my own story until now. I have always wished someone would make a certain type of story, so finally decided to make them myself! This will hopefully be the first of many! My stories will likely follow one or more of the following. Anal, BDSM, Erotic Couplings,, Exhi...

The Cafeteria Ch. 03

by trikon309 on Aug 18, 2017
Gay Male

I woke with a start. What a nightmare, I thought to myself. I turned expecting to see Kyle next to me and realize everything is OK. But he wasn't there. And it hit me. It wasn't a dream. It was all to real. The man I loved had turned into something I didn't believe was possible. Some sort of controlling monster using me a nothing more than a sex toy. I was s...

The Man I Was Ch. 02

by blendover on Sep 16, 2017
Gay Male

I thought everything would change after my experience with Anna. I wasn't sure how, but what happened seemed so significant in my mind. I thought it would change everything, but it didn't. I went home that night and showered, shaved, and got ready for bed just like I always did. My mind was running in circles, but that was about it. After I finished my show...

New Neighbors Ch. 03

by idsweaterguy on Sep 16, 2017
Gay Male

Jeffrey positioned me on my knees in front of him. My arms were still cuffed behind me but he did untie the rope that had bound my ankles together. The penis gag was still in place and, of course, I was still wearing all that yellow mohair—the ankle length sweater dress with the turtleneck collar, the mittens and the knee high socks. I watched wide-eyed as h...

Turning the Teacher Ch. 02

by Dave933 on Aug 18, 2017
Gay Male

I woke up early, sunlight pushing through the feeble barrier provided by pale yellow curtains. I was lying on a double bed in a strange room, and for a moment I wondered where I was. Then it came back to me. I was at my teacher's house, Mr. Wild. I had found a sordid and sexy video he had starred in before he became a teacher, and used it to blackmail him...

Bob Handles Mark's Huge Tool Ch. 01

by scrotus on Aug 18, 2017
Gay Male

I had long fantasized about being involved in a sex situation with more than one guy. I had done several three ways with a woman (two guys and one girl) but they never involved the other guy and I performing on each other. In recent years, I've developed an insane desire to move beyond my several male-male encounters and add a third guy in. This is because o...

The Lure of Cock from the Closet

by jakladd on Oct 15, 2017
Gay Male

It's true. We desire cock. Our wives have no idea what goes on inside of us with this desire to submit...to cock. We hide it from everyone but in our minds it's a runaway train. To touch, feel, pull on, sniff, rub our faces in it, lick it, taste it, suck cock. We've done it before, maybe a short time or a long time ago. The specter of guilt and shame dampens...

My Dream Solution Ch. 01

by Cyanlot on Sep 15, 2017
Gay Male

[Note: This is a long introductory setup to a multi-part story. There is *no* explicit sex in this first chapter. If you are looking for quick, hot read, move on. This is not it. Things will heat up in later chapters, I promise. --Cyanlot] Chapter 1: When I Hit the "Change of Life" When Massachusetts became the first state to legalize gay marriage, Todd a...

Pony Boy Ch. 07

by ChestersBoi on Sep 14, 2017
Gay Male

*** Chapter Seven of Pony Boy *** Once again, appologies for the wait. I hope you think it's worth it. As ever, if you're new to this story please don't start here. It won't make much sense and won't be anything like as good if you miss the build up. Meanwhile, despite the title, there's no pony play in this chapter. In fact, it explores Ben's other little...