Gay Crossdressing Cuckold Stories

153 results
Orientation
Length
Source
Infinite Scroll

The Bartender Ch. 02

by Pan2 on Jun 8, 2020
Gay Male

As soon as Roger walked through the saloon-style doors, Kent reached for a glass. He'd never before seen a man in such need of a drink. If the dark rings under his brown eyes weren't enough, his incorrectly buttoned-up shirt and mop of dishevelled brown hair clearly used to more attention than it was currently getting were a clear indication that Roger was...

Can I Borrow Your Boyfriend?

by knowsbetter on Mar 2, 2020
Gay Male

"Ok, Ok, I got one," Josh said. I was out with my friend Melissa and her new-ish boyfriend Josh, and we were three glasses of prosecco into a late brunch. The waitress was clearly hungover and didn't give a shit, service was winding down, and we were off in a corner gossiping and talking trash. The current topic: terrible first-date icebreaker questions. "B...

Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...

Exploring My Bi Side Ch. 02

by bscurious1 on Oct 19, 2020
Gay Male

Randy and I kept up our meetings, sometimes weekly sometimes two or three times a week, just depended on our schedule and how horny either of us were. We always met at his house in his home studio which offered us a lot more privacy and freedom. As I had stated the massages pretty much stopped but he would still give me one when I needed one or just wanted o...

Cross-Dressing, Gay & Lesbian Sex 05

by SusanJillParker on Aug 30, 2017
Gay Male

There are no underage characters in this story. All characters are over the age of 18-years-old. * Daniel's one time bi-sexual fantasy consumes him "Maybe if you allowed me to have sex with Martin," said Emma to Daniel pausing without finishing her thought. She looked at him with teasing eyes and flirty sexiness in the way she used to look at him when t...

March Madness Ch. 09

by watchdwag on Sep 14, 2017
Gay Male

If you have been following my story, you know that Randy, a friend of mine since high school, has been blackmailing my girlfriend Sandy and me for the last few weeks. Sandy and I agreed to be his sex slaves for one month, as long as at the end of that term, he would turn over the compromising videos he filmed of me. I was the first to be blackmailed into ga...

My Gay Crossdressing Vacation Ch. 04

by Flame666 on May 11, 2020
Gay Male

I slowly opened my eyes, remembering what had just happened over the past 24 hours, I woke up looked at the time, it was just before 7 pm. Earlier I had decided to start getting ready for my date with Paul and John around 7:30 so I got out of bed to get started. I was going to start with a shower and because I had a bit of extra time decided to take off my b...

I Once Was Lost But Now Am Found Pt. 02

by eviltwin52 on Oct 5, 2020
Gay Male

In Part 1 I found a friend in Leon. Having lived the greater part of my life alone, maintaining my bond with Leon was the most important mission I'd ever had. Sucking his cock was my way of showing him my appreciation for his comradery. He didn't ask me to do that. He didn't tell me to do that for him either. All Leon did was nudge me in the right direction....

Comfortably Numb

by Nils Huim on Jun 19, 2018
Gay Male

The humiliation was now complete, and Sean was loving it. He was down on his knees on the kitchen tiles wearing nothing but a pair of lace panties, and his wife's lover's cock was in his mouth. It was a beautiful thing to behold (and taste). Long and proportionately thick, from behind its bulbous pink head until it disappeared, at a slight curve, into Gary'...

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...