Gay Crossdressing Cuckold Stories

153 results
Orientation
Length
Source
Infinite Scroll

Cocksucker: Cocksucking Training

by silkstockingslover on Sep 14, 2017
Gay Male

Summary: A twink teaches a straight man how to suck cock properly. Note 1: Thanks to goamz86, Robert and MAB7991 for editing this story. You do not need to read the first part to enjoy this story. In case you are curious, here is a brief summary of part one called "Cocksucker": Chris, a married straight man, is stuck at the airport when his flight is d...

A Real Bathhouse Slut is Made

by Danmo1 on Sep 16, 2017
Gay Male

This true account of the activities of a mature 50'ish guy continues from my first time at a bathhouse entitled The Making of a Real Bathhouse Slut. As I drove home from the bathhouse the first week I had a hundred different things going through my head, one of which was guilt. I quickly realized that after years of no sex with my wife there was really noth...

A Slut is Born

by Luvsishyp on Apr 21, 2020
Gay Male

Special Thanks to madam_tasha for amazing editing and assistance. I sat on the motel bed feeling a nervous excitement. "This will do just fine," I thought to myself, as I looked around the cheap, seedy room. It was relatively clean but had definitely seen better days. The carpet, an ugly pale green, was worn and faded from years of use. An oddly patterned...

Exploring my Sexuality

by alexis19901 on May 12, 2020
Gay Male

I'll just start by saying that I've never attended any sauna that may get mentioned in the story. No names that are mentioned are real people either. It's something I've purely put together based on fantasy alone. Thanks for reading! Today was finally the day. I'd been waiting months to go and push myself to try the closest sauna to me which was a short tr...

How Did I Get Here

by bart_allen on Oct 15, 2017
Gay Male

I found Wendy on OKCupid. She was just another face as I scrolled down, albeit a fairly attractive one. I clicked on her profile, glancing over it: she was older than me, which is not usually my type, and she was six years older than I at thirty two. She had a darker natural red hair in shoulder length cut, but a sort of light olive complexion, and pouty lip...

Bathhouse Heaven Ch. 32

by glory_first on Aug 22, 2018
Gay Male

The bathhouse was fairly empty this Wednesday afternoon, a reminder of different rhythms from the past. Following the familiar routine, today with more space to undress than the case lately. The beer was quenchingly cool, and quickly finished. Going upstairs, I walked towards the sling room, noticing a couple of men going different ways than my path. How...

Eric's Little Buddy

by alphafan on Aug 18, 2017
Gay Male

I was staring out my office window at the worst blizzard in New York history when the phone rang. I answered the ring and recognized the voice on the other end. Eric was calling from his house in the Keys. Eric is a successful advertising executive with a house in Key Largo, a condo in New York, and offices in New York and Miami. In addition, Eric is an a...

The Massage

by george51 on Aug 18, 2017
Gay Male

Massage. A new experience for me. I am lying there on my stomach being kneaded by strong hands, with a tiny little towel doubled folded and laid over my ass. The masseur is a sun tanned body builder type who also has a little towel wrapped around his waste. He has a very hot body of course and is the sort of man every woman wants to fuck. He is slowly rubbi...

Fed Up with Tiny Tom Ch. 02

by MildmanInVA on Sep 16, 2017
Gay Male

********************************** Tiny Cuckold Tom meets 20 year old Adonis David and is humiliated further ************************************ I thought that cleaning my beautiful wife's dirty ass was the ultimate in humiliation, but that was nothing compared with the evening I spent with Shannon and David Walker, her new 20 year old lover. As instruc...

Descent into Marital Depravity

by HerLittlePiggy on Sep 14, 2017
Gay Male

The big king sized hotel bed shook and I glanced at the clock on the night stand. It was after two and I had to get up for a seminar in four hours. I'd left her in the hotel bar downstairs almost four hours earlier and at the time she was standing next to a group of five young men who all looked to be half her age. "Did you have fun?" I asked as my wife cli...