Gay Crossdressing Cuckold Stories

153 results
Orientation
Length
Source
Infinite Scroll

Coming to Terms

by HerLittlePiggy on Aug 18, 2017
Gay Male

I stood naked beside the bed. My hard cock jutted straight out from my body betraying my excitement. "I have never done this before," I said softly. "But it excites you doesn't it?" "I guess so," I answered as my cheeks flushed red with embarrassment. "You guess so? It's a yes or no question. Does it excite you?" "Yes," I replied honestly as I cast m...

Caught

by HerLittlePiggy on Dec 3, 2019
Gay Male

Her thick thighs were surprisingly shapely with delicate ankles. Her wide hips framed a well groomed but still hairy pussy. Her waist was nicely tapered despite her chubby belly and her huge 40dd tits were amazingly firm given their size and the fact that she was almost 40. Kristen was a big girl and she towered over my petite 5'2" tall wife. Her long blond...

I Turned Myself Out

by drmweaver705 on Jan 29, 2020
Gay Male

All characters are 18 or over. ***** My journey must have begun with my discovery of porn. When I was eighteen, I discovered a trove of porn magazines hidden out in the abandoned shed of a derelict and condemned house near my childhood home. This was the first time in my sheltered life I had ever seen anything like it. The magazines varied from soft nudit...

March Madness Ch. 08

by watchdwag on Sep 14, 2017
Gay Male

As we arrived at Larry and Ann's, I couldn't believe how anxious I was to see Larry again and to meet this man, Mark, who had so dominated their lives that they would both allow him to "mark" them as his personal property. A month ago I was just an average guy with a steady girlfriend with perhaps a much better than average sex life. But all that changed as...

A Plan goes Awry

by HerLittlePiggy on May 29, 2018
Gay Male

I sat beside my wife in the loud, crowded bar. I'd been drinking for most of the day and I had a buzz but I was purposely acting much drunker than I was. My wife giggled nervously beside me as she talked to a young man she had met less than an hour before. He had an athletic build and an attractive face with dark ebony skin and a bright mischievous smile....

Lady Fortune's Smile

by Malice2 on Aug 18, 2017
Gay Male

From deep in the bowels of Hell, the Prince of Darkness releases his hordes of foul, evil and dysfunctional minions bred for the sole purpose of showing up to roommate interviews. And I, Theodore, the legal head of household, must sit here through each horrifying, grueling one on one session with these abominations and remain cordial, collected and most of a...

My Name is Dave Ch. 01

by davas on Sep 16, 2017
Gay Male

Hi. I'm Dave and this is my story. Let me tell you a little about myself. I am six foot even, 155 pounds with shortish blonde hair, and blue eyes. I am thin, but with strong legs and ass. I have light body hair, a fair complexion, but I can hold a tan. I think I've got a nice body; I'd fuck me if I had the chance. I am twenty-four years old, two years out o...

Failed Threesome

by RSchwuler on Sep 14, 2017
Gay Male

Sarah and I had met Stuart online. He was 42, 10 years older than us. In the sixth months that we had been together, Sarah and I had enjoyed a MMF threesome with a mutual friend twice before, but it been a more conventional affair, both of us giving Sarah all of our attention, careful to avoid crossing swords. Sarah and I were both curious about trying somet...

Mel Takes My Manhood Pt. 02

by RSchwuler on Jan 20, 2020
Gay Male

This story is a very over the top work of fantasy, and it contains extreme humiliation, ws, unsafe sex practices. Please don't read if it's not your cup of tea. ***** The next few days I struggled to return to normalcy. I tried to focus on work. Went to the gym. I got a new phone, ordered a new credit card. But it was impossible to not think about what Mel...

Hay and Straw

by lightskinboy on Jan 24, 2019
Gay

It was a class trip during college. Most of us were between 18 and 20 years old at the time and of course we, the boys, were interested in sex, despite most of us not having any, because girls were always playing hard to get. My name is Tom, and I was the only black kid in our class at the time. So basically, everyone in my class was white and all my buddies...

Open in Reader