Gay Crossdressing Halloween Stories

300 results
Orientation
Length
Source
Infinite Scroll

Complete Control

by vicw1392 on Apr 27, 2014
Gay

James had read, and seen, porn about men who could change the world, and that's what he'd been doing last night. After a quick, and mostly unsatisfying, wank, he'd fallen asleep wishing that there was more of this type of porn for gay men; where was the fun in reading about unlimited possibilities if all the characters do is make everyone's tits bigger? Then...

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Becoming a bitch

by Testytesterton on Nov 28, 2019
Gay

(Skip this if you don't like boring behind the scenes stuff. Wow! Over 3000 likes and story of the week for my first story here! Thanks to everyone who has liked, bookmarked or commented. The feedback lets me know what works and what might need work. I would love for this to be the most popular story in its category, so if you like the story, "like&quot...

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My Gay Crossdressing Vacation Ch. 06

by Flame666 on Jun 9, 2020
Gay Male

I woke up looked at the clock, it was 10 am the sun was out and hot, it was a beautiful day. I rolled out of bed realizing that I had cum all over me, in my hair, in my mouth and leaking out of my boi pussy. I peeled off my 40 D breast forms and headed to the shower. While in the shower, I thought about my plans for the day and the coming night. I remember...

Pussyboy Nephew Ch. 01

by bufmuck1 on Sep 16, 2017
Gay Male

So I went to stay at my aunt and uncles. I had finished another year at university, and my mom said I should spend a few weeks with them, if I had nothing better to do. At first I wasn't that interested, what with my aunt living in a quite area and they were both in their forties, I liked the city where we lived, and enjoyed being around my mates. However I...

The Boifriend Ch. 01

by AdmiralSquish on Aug 8, 2018
Gay Male

[pre-story]Content Warning: SUPER gay. Crossdressing. Sissy self-deprecation. There's going to be some unrealistic anatomy later on, huge cock, huge balls, and huge loads. Disclaimer: All characters are 18+[/pre-story] ***** The Boifriend, Chapter 1 "Whelp!" Leo exclaimed as he stood up and gave an exaggerated stretch, feigning a yawn. "Looks like it's t...

Aquata Cove Ch. 99

by Feare909 on Oct 9, 2017
Gay Male

Chapter 99: Happy Halloween The water of the sea splashes on a rock as seagulls screech in the distance, flying overhead at the break of noon. On the small rock, a small otter breaks out of the surface, and climbs onto it, standing on his hind legs. He wears a gleaming brass collar scribed with kanji, along with a marble dangling from the base, besides his...

Rex's Horny Halloween Pt. 02

by TeamCravings on Dec 12, 2018
Gay Male

Handsome Rex Davenport soaked his fit six-foot body in a nearly full tub just before having to get ready for work. It was Halloween and this ginger-haired 40 year-old had a fascinating evening ahead of him. This special night had all been suggested and planned by his dear sex mentor Lorna, a hot MILF who had launched herself headlong into his life in just a...

Cocksucker: Cum Slut

by silkstockingslover on Sep 14, 2017
Gay Male

You do not need to read the first four chapters of this story to enjoy this story of a straight man that gets submerged into the drag queen world of San Francisco (but obviously it helps). In case you are curious how this straight married man got into this predicament here is a brief summary of the first four chapters of "Cocksucker": Chapter 1: Cocksucker...

Hotel Night

by guy_manuel on Aug 18, 2017
Gay Male

It was my first time crossdressing. I have no gender identity issues or anything, I just wanted to try it. But I also wanted to have a little fun since I was sure this would be the only time I'd do something like this and I hadn't gotten laid in a while. It probably wasn't the smartest idea, but if literotica had taught me anything it was that Craigslist was...

Rex's Horny Halloween Pt. 03

by TeamCravings on Dec 19, 2018
Gay Male

Rex smiled warmly and began to obey his apron-clad Nordic bear master. Stripping for this hungry appreciative group was becoming so easy, almost second nature! The host devil had made sure the drinks of the guests were not going unfilled. A Spiderman costumed waiter seemed to be eagerly topping all the strong drinks up. The party was ramping higher and Rex...