Gay Crossdressing Halloween Stories

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Daddy's New "Wife"

by Shadow Shark on Dec 4, 2019
Gay

Hello! My name is Tristan Wood, or Triss as my friends and family like to call me. I'm 22 years year old, recent college graduate, and unemployed. Right now I'm living with my old man Harry Wood, he's a thickset man in his late 40s. Though, pops has been living in constant sadness since mom passed away seven years ago. At first, he barely bothered to do anyt...

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My Gay Crossdressing Vacation Ch. 01

by Flame666 on Apr 21, 2020
Gay Male

It was mid-January and I was getting tired of the cold and I was horny so I started to think about planning a gay vacation. After a lot of thought I decided on Palm Springs in Mid-February. A bit about me, I am a straight looking and acting man 60 years old slim and fit. However, I love cock and like to dress up in panties and other lingerie. A few years ag...

My Gay Crossdressing Vacation Ch. 05

by Flame666 on May 12, 2020
Gay Male

As I was falling asleep, I realized that the egg and the plug were still inside me. Terri must have put the plug back in after fucking me. I wonder where the remote for the egg is. Oh well off to sleep. I was dreaming, I could feel soft hands on my back and running over my panty clad backside. Then I realized that it was not a dream. A pair of delicate hands...

Remember Yahoo Chat? I Sure Do

by FinallyOpeningUp on May 22, 2019
Gay Male

The news was unexpected. I can't say it was devastating. In fact, it elicited no truly emotional response from me whatsoever. But just a few months ago I was scrolling through my Twitter feed and a headline jumped out: "Yahoo Chat to shut down permanently." I paused for a moment when I read that headline. Yahoo Chat. It had been probably ten years since I,...

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...

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...

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...

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...

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...