Gay Crossdressing Halloween Stories

300 results
Orientation
Length
Source
Infinite Scroll

AU Ch. 06

by FangsAnarchy on Aug 30, 2017
Gay Male

((Sorry everyone there isn't any sex in this. I split the chapter and so the sex was cut out. I promise to make up for it in 7 and 8)) "He had been distant this week. Every time I tried to invite him out he'd find an excuse. I feel like he knows I'm hiding something from him. I mean I'm not hiding it on purpose; I'm just waiting for the right time to tell...

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...

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...

The Watcher and the Woods

by Pelaam on Aug 18, 2017
Gay Male

Looking around, Jackson smiled at the thought of spending some time in the picturesque area. The autumnal colours a dazzling array of gold, ambers and reds. The crew of which he was a part were renovating a small hotel on the outskirts of a scenic, little town that relied heavily on tourist trade. The town had a nice variety of shops, not that he expected to...

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....

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...

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...

Insatiable Rob & Eric Ch. 17

by insatiablerob8 on Jan 30, 2018
Gay Male

A warm afternoon sun, cast through the greenhouse, while I was watering. Amidst a lush jungle of foliage and the steady whine of circulating fans, it was peaceful and I was startled when I felt a swat over my ass. I turned to find Eric, grinning and very proud of himself. "Fuck! You scared the shit out of me. But... I like it when you drop by... what's up?"...

Earning Danny Ch. 05

by EricMorrison on Sep 19, 2017
Gay Male

Jake's Point of View The next morning, as I was driving to pick up Danny for school, I was a bundle of nerves. I had no idea how he would react to my admission the night before, so I had no idea how I should act around him. I really didn't mean to tell him I loved him, but he caught me completely off guard with his boldness, and I couldn't help it, it jus...