Gay Crossdressing Cuckold Stories

153 results
Orientation
Length
Source
Infinite Scroll

Just a Game Ch. 02

by tamgreen on Sep 14, 2017
Gay Male

Pete woke up alone, and the apartment smelled amazing--something delicious was cooking. He tottered unsteadily to his feet and looked down at himself. He was wearing nothing but a t-shirt and a furious hard-on. He pulled on a clean pair of boxers, stuffing himself awkwardly into the fabric tent before trudging to the kitchen. Dean was standing at the stove n...

You are a Sissy Pt. 08: Future

by Roland15Rollin on Dec 30, 2019
Gay Male

Hello, sissy. Well, we have come to the end of our journey together, princess. We have explored every corner of your gay sissy mind and now we have come to the end. And what a journey that was. We learned so much, sissy. We learned about who and what you are. We learned about what you want. We learned about what you need. And we finally got rid of all of...

Adam & Steve, Not Eve

by SEVERUSMAX on Sep 14, 2017
Gay Male

Eve Winters, known to her slaves and the BDSM community, as "Mistress Eve", was quite pleased with her success in controlling her slaves so far. She was especially satisfied with the power that she had over Adam, her husband. She married him to get legal title to half of his estate, which has considerable. She frequently fucked other men, and only allowed A...

Dominating Devin Ch. 02

by Cyanlot on Sep 14, 2017
Gay Male

I imagine that Devin thought it was a little strange when I invited him over to watch a movie together. It wasn't "bizarre strange." We'd talked before about the fact that we both liked bloody action films but often missed them because our wives weren't interested and it just wasn't the same sitting alone to watch a movie. I'd engineered it so that Marcie a...

Sex Starved Cuckold Ch. 01

by Anal Slave on Aug 18, 2017
Gay Male

Before I met my wife I had a few sexual adventures that involved Bi married couples. My favorite is a Bi married couple, who turned the tables on me. I though I would get some pussy from his beautiful wife. Let her suck and fuck my cock. I would suck her pussy and lick her asshole for her BUT NO, She let me know real quick that I was only there to suck her h...

The Hapless Detective

by idsweaterguy on Sep 16, 2017
Gay Male

Chapter 1: I parked my car four houses down from the house the man I was following had parked in front. I watched the middle-aged man who was about six-two and wearing a brown fleece jacket, jeans and a brown baseball cap get out of his car, throw a backpack over his shoulder and walk up to the front door of the non-descript but rather large house in a newe...

Exploring my Sexuality Ch. 02

by alexis19901 on Jun 2, 2020
Gay Male

Just a quick recap from the first chapter. I'd made my first trip to a sauna, lost my virginity, got spit-roasted and then another guy came in my ass all before I left. The last guy left me his number and I just couldn't resist. This story will contain some crossdressing. I'd gone back to my normal life for a number of weeks since my trip to the sauna. Havi...

Research Pt. 02

by eviltwin52 on Aug 18, 2017
Gay Male

Please read Research part one first. ***** "So in summation I submit that although a certain portion of the male population engages in homosexual acts, they aren't homosexual at all. No, they are under-endowed males who wish they could have heterosexual relationships but whom women shun. Through aggressive parenting, peer pressure, and social activities th...

My First Gay Orgy

by yvetteinpanties on Jul 4, 2018
Gay Male

Note: autobiographical, not fiction. Lucky me. *** The idea of sucking cock did not appeal to me for the first 50 years of my life. Then, the love of my life left me, claiming I was too dominant to put up with. In an emotional turmoil, I began to investigate websites about how to be less dominant. Web searches for such things as 'female led relationships'...

My Name is Dave Ch. 03

by davas on Sep 16, 2017
Gay Male

I did not mean to hit accept. That was the thought that kept running through my head. It had been a bizarre chain of events that I could probably never recreate even if I tried a hundred times. They couldn't hold me to that, could they? I didn't mind getting fucked by Steve, in fact, I enjoyed it and wanted to do it more often. My problem was giving him a b...