Gay Enema Stories

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Orientation
Length
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Infinite Scroll

A Truth or Dare Game to Remember

by Mikehawk2187 on Apr 21, 2020
Group Sex

[Warning: This story contains guy on girl, girl on girl, and guy on guy. If you aren't into that sort of thing you might want to stop reading.] *** Four friends haven't seen each other since they all graduated high school. They had all gone their separate ways and hadn't talked much since. They were all sophomores in college at this point. Jason had long...

The Path to Happiness Pt. 07

by brendachaplin2000 on Nov 18, 2019
Transgender & Crossdressers

Several days had passed since my encounter with David, I have since meet him for coffee as Brenda, and I can see us becoming good platonic friends. We are both clearly bottoms, and we made a date to check out a few of the gay clubs in London. I also had my second appointment at the gender clinic, the hormones had already taken some minor effect and my bust...

Male Model Nude for Money and Sex

by MotherandSonTrueConfessions on Oct 7, 2019
Exhibitionist & Voyeur

After modeling naked for women that he knew, years later, modeling nude while in college brought back fond masturbation memories. Author's Note: This is a true story about Dave, a proud crossdresser who goes by the name of Kelly when he's dressed as a woman. A submissive male with a medium build and feminine features, at 5'6" tall, when dressed in drag, mo...

Lovers That Never Were

by catchercradle on Mar 2, 2020
Romance

Lizzie, my lesbian friend had tried and failed many times to set me up with different straight friends of hers but there was never that chemistry between myself and her picks for me. We were besties. When one of us was down after a break up the other was always there to listen. Have a cuddle and a drink. We would even sleep together though nothing more untow...

Gina Falls for Friend Yvonne

by 0ExpirationDate on Jun 9, 2020
Transgender & Crossdressers

"How? Is it really possible?" Gina wondered in disbelief. A tiny niggle of a feeling at the back of her mind had started months ago. She had been refusing to allow it to come into the light. Despite this, the niggle had blossomed. It had started with a seedling of a friendship. That friendship had not only grown but blossomed. She had been trying hard to br...

Who Killed Jenny Schecter? Ch. 16

by OGSalli on Jun 9, 2020
Celebrities & Fan Fiction

Chapter 16 The Morning AfterThe next morning they were quiet with each other. When Lauren was ready she zipped up her overnight bag and went out into the hallway, closing the door to her hotel room behind her. She turned and saw Carmen sitting on an upholstered bench by the elevator bank, with her overnight bag, ready to go. "Been waiting long?" "No, just g...

My Flagrant Public Nudity Ch. 03

by LuckyLizLondon on Aug 24, 2020
Exhibitionist & Voyeur

Susan had long forgiven me for laughing my ass off at her self-inflicted predicament in Portland and even let me record her account of the events. But now she was wound up like a top and spinning wildly. "I really do think I'm becoming a lesbian," Susan said. "Or maybe a lesbian of convenience. And it's all your fault. I never felt any attraction to women b...

A More-Men Wife Ch. 01 Pt. 04

by PolySwingerWife on Dec 14, 2020
First Time

I'd gotten married on Friday afternoon, and by Monday afternoon I'd had sex with eight other men. On Friday morning I was a virgin. By Monday afternoon I'd lost my virginity to a man that wasn't my husband, been gangbanged by five black men, then I went out looking for more men to fuck me. I was eighteen years old, and the man that took my virginity was th...

Humiliated at an Outlet Mall

by willow619 on Sep 25, 2017
Transsexuals & Crossdressers

A month before my birthday my wife Mel (short for Melanie) hinted she had a special surprise planned. I dislike having a fuss made about my birthday, and even though it was my 30th I expected nothing more than a dinner at a nice restaurant. Instead, on my birthday my wife and I headed to an outlet mall, a regular activity for us. But this time we drove to a...

Allison

by Timewell on Sep 14, 2017
Anal

"Uncle Joe, please! I'm serious, OK? You have to stop sleeping with my friends!" Lilly, my niece, was livid. I'm not exactly sure how she found out, but then I hadn't exactly been going to great lengths to hide it either. Emily and Laura were both consenting adults. Sure, I was twice their age. But it was they who had come to me. Laura had been the first a...