Shemale Gloryhole Stories

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Punished in Paris

by maia24 on Sep 16, 2017
Transsexuals & Crossdressers

Maria the very pretty Irish transvestite had arranged to meet the men in Paris. She had agreed to be taken to a house in the suburbs to be punished, abused and sexually defiled by a number of men. She was dressed in a purple mini dress and wore very expensive lingerie. She was totally smooth and as she walked to the avenue to meet one of the men she was full...

Dick World

by darkness_drearing on Dec 25, 2019
Bisexual

For contributors As was stated at the top: while there were will be two general threads to go off of (for a guy and girl), feel free to create your own characters or scenarios. The only shared premise among them needs to be that they find themselves, however you decide that happens, in this universe and, as The Eagles would say, "You can check out any t...

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Shemale Fun

by orangemaestro on Sep 26, 2017
Transsexual

You are a good-looking man in your mid-twenties. You are 5'10, 170 lbs., and in good shape, with some muscle definition. You have always considered yourself a man's man, but lately you have developed a curiosity about women with...something more. When you fantasize, you sometimes find yourself imagining a cock between the girl's legs. Pretty soon, that's the...

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Brazillian Punsihment

by Ravenarioch on Feb 7, 2018
Transsexuals & Crossdressers

Frank Shepard a private detective who is trying to find his luck in Rio de Janeiro awakes in his bed during the day of Carnival, the sun's rays hitting his eyelids he turns himself over in bed and looks at the sky on this lovely day. His sky blue eyes thinking about what a horrible day to be a private investigator, his case was to find the little brother of...

Neighborly Gloryhole

by tabber on Sep 25, 2017
Group Sex

Dave's wife Sue was going to be out of town for the weekend, so he invited several of his buddies over for poker night. They had played for about two hours, and downed half of a keg of beer when Dave mentioned that instead of smoking cigars after the game, he had an alternative activity. Everyone was curious and when he told them the plan, they all agreed t...

Blossoming Shemale Ch. 02

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by:http://www.literotica.com/s/reluctant-shemale tawnysuede's Reluctant Shemale if you enjoyed it, I hope you'll enjoy this series. * * * My name was James. It was, before everything that happened, anyway. I'd come from pretty good stock, as the snooty, upper class would likely say. I guess I still did, although it would take a DNA test to...

The Wish

by Fangslover on Jan 16, 2019
Fetish

—This is my first public story, my plotlines are usually quite lacking... I tend to get straight to the point of this kind of writing, which is erotica. I know it’s probably not the best, but I hope someone else may find it enjoyable. All characters in this story are fictitious and are at least 18 years of age.— “I wish I would be seduced, bitten, and turned...

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When Sara Met Bob Ch. 05

by yellowfrog on Sep 14, 2017
Fetish

Bob remains the love of my life, the fountain of my admiration! Handsome beyond words, virile and composed, sexually insatiable in many ways, Bob has become what every woman wants - in addition to her own husband, of course. In the intimacy of our extra-marital affairs I enjoy massaging his prostate, deeply and slowly, my fingers moving very deliberately to...

Sissy Whore Ch. 04

by DebbieDublin on Mar 14, 2018
Transsexuals & Crossdressers

I stumbled to the bathroom to fix my face, my head still spinning. I reapplied my lipstick and dusted off my foundation. Wiped away the mascara stains from my cheeks and reapplied. When I was done I returned to the living room. 'These are for you.' He said when I approached. He reached into his jacket, extracted a pair of large gold coloured hoop earrings...

Gloryhole Sex Toy Fun

by winterknights on Sep 12, 2017
Exhibitionist & Voyeur

I'm a young 23 year old and as you can imagine I do tend to get excruciatingly horny pretty much on a daily basis. I'm currently single to so it drives me insane, having to sneak off for a secret wank while in work, while watching TV, riding on the the bus. Well not really on the bus, it's not that bad yet. OK, OK I did do it on a bus once when I was younger...