Gay Crossdressing Cuckold Stories

153 results
Orientation
Length
Source
Infinite Scroll

The New Order Pt. 04

by Iamkrazy4 on Apr 21, 2020
Gay Male

Part 4: On The Road to Love There I was, on my back, a dick in my butt, mouth, and both hands as I laid on table they had brought into the locker room. Around 3/4ths of the football team, and the coach stood around cheering as they celebrated their upset victory over our rivals. My throat and ass were sore as this onslaught had been going on for over an h...

It Was So Exciting

by sindyxdresser on Aug 18, 2017
Gay Male

It was about 230 am Friday night when I walked into the Crypt adult book store on 30th Street in San Diego Calif. The Crypt's usual clientele was mostly gay men, and tonight was no exception. I felt my face burning as I walked back into the peek booth part of the store. These booths had no doors or curtains so offered no privacy of any sort. There were sever...

The Reluctant Bear Hunter

by newpaulman on Jul 3, 2019
Gay Male

First I must apologise to any gay men reading this who like their stories with a romantic element. That is not what I am looking for with a man. I am a part-time bisexual. I can go months without thinking about gay sex, but then the urge comes back. The urge to be fucked, that is. The urge to suck a cock and see spunk fly from it. The urge to get naked with...

Crossdresser's Unexpected First Time

by kprice1984 on Nov 27, 2017
Gay Male

Just want to say firstly, that this story is 100% true. Secondly, it was much better in person. I'm just getting around to writing it after several years. ***** I'm a 20 year old guy, very good looking, easy to get girls. Brown hair, green eyes and a sexual appetite that's hardly ever satisfied. I had always had a craving or tendencies towards being a lit...

My First Kiss

by amygurl on Aug 18, 2017
Gay Male

It all started about 2 months ago when a new neighbor moved into the apartment next door to me. His name is Jason, he is very personable and just an all around amazing guy. He is 34, about 6'3" with black hair and blue eyes and we hit it off pretty much as soon as we met. We are both veterans and newly single and we both liked to watch sports on TV, but we d...

I Make Believe I'm a Cuckold Ch. 04

by donaldelliott11 on Feb 10, 2020
Gay Male

This is the fourth and final chapter. You should read the others first. This chapter contains a scene of incest between two adults. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help me improve my writing; ratings help other readers find what they most will enjoy reading. Ra...

Cuckold at a Cocktail Party

by CuckoldGuy on Sep 1, 2017
Gay Male

When I was a young, naive, immature man or maybe I should say boy, I was engaged to be married to a very beautiful, sexual, voluptuous, full figured girl. She had full puffy lips, large rounded breasts, curvy hips with full rounded buttocks. I introduced her to my boss. He was an old wise man and she must have made an impression on him because a couple of da...

The Road Sometimes Traveled

by rnumbers123 on Aug 18, 2017
Gay Male

The following is a first time gay tale that grew out of the dark place in my mind. My stories tend to have a cuckold theme. Most cuckold fantasies have a bisexual element. This is no exception, but it crosses a line. It's not uncommon for cuckolds to question their sexuality. As a mental exercise, I've looked at another man in the gym, wondering if I could...

You are a Sissy Pt. 07: Cuckold

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello, princess. Hello again. I see you are back. That pleases me, sissy. It pleases me that you have come back for more of what only I can give you. The truth only I can give you. And we have come so far together, princess. We have come so far exploring the depths of your sissy feminine mind. And your mind is feminine. Make no mistake about it, princess....

Bikini Boi

by MySissyWorldx on Oct 3, 2018
Gay Male

My Brothers Troublesome friends... Note: everyone is of a legal age, and names have been changed for the sake of this story Enjoy *** My first time was more than a little bit terrifying, but enriching to my life beyond my wildest dreams. It began on a family holiday, just after my older brothers 21st birthday, him being 2 years older than I was at 19. Be...