Shemale Underground Sex Club Stories

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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...

Chen

by spitzharder on Sep 14, 2017
BDSM

Chen, a beautiful, olive skinned, Israeli, Shemale was the owner manager of an underground club called 'Weals and Squeals', which encapsulated the nature of its customer's interests. The lesbian clientele were of all ranks and walks of society, the fees were high but then so were the scale of desires. A lesbian mistress used to bring a nubile naked young...

Stiff Sentencing For A Young Man

by SugarandSalt on Sep 11, 2017
Transsexuals & Crossdressers

Ellis stood warily before the judge. His crime was small but this was a small town. Crime was an insignificant concern in Sparklewater. Ellis knew the reason for that was because Sparklewater had the reputation of swift and particularly harsh punishment. So swift in fact that Ellis had been tried and convicted in a matter of days. All that was left was sente...

Bisexual Orgy

by Samuelx on Sep 14, 2017
Group Sex

Gino Harrison walked into his office. He had been working for Jefferson & Mason for three years now. It was an advertising agency. Gino was a tall black man in his early thirties. He had dark brown skin and curly black hair. A rather handsome man. Gino was a somewhat successful man. He engrossed a couple hundred grand a year and that wasn't bad at all. Espec...

Cuckold in the Family Ch. 12

by swmichcuck on Sep 15, 2017
BDSM

After a fun filled night at the BDSM club in Detroit, as promised I prepared our little trio for a trip to Chicago to an underground sex club that a Dom had turned me on to. After researching the club on it's website, I registered us and paid the stiff fees that the club required. I had a meeting with Kayla and Cassie to let them know what to expect. They b...

A Night Out

by Boomerjr34 on Sep 12, 2017
Transsexuals & Crossdressers

NOTE 1: I'd like to thank those who edited this story and helped make it better. Gaymaninawomansbody, Kate09 and ThePastBehindMe. NOTE 2: This story has had some man on man sex, shemale on male sex, group sex and a woman too. ***** I have been working with the same sales group for years when they hired a new guy from out of state. He moved to town when hi...

Dark Life

by Samuelx on Sep 14, 2017
Transsexuals & Crossdressers

Kiara looked at herself in the mirror. She liked what she saw. A tall girl with long black hair and pale blue eyes. Her skin was light bronze. She stood five feet eleven inches tall in her bare feet. She had just stepped out of the shower and finished drying herself up. Kiara was a pretty girl and she could hold her own against most of the other females out...

Healthy Behavior

by BrettLynn on Sep 16, 2017
Transsexuals & Crossdressers

Yes, it's a new series, fans of mine. I know you like Marilyn, but she's on hiatus. Deal. Anyway, I do have something interesting for you. It's an unusual tale, but then again, my writing tastes have proven to be a bit unusual. I'm about as mainstream as N'Sync is underground. So without further ado, let's get started. Oh, and yadda yadda yadda over 18 to re...

Amy Finally Lives Out Her Fantasies Ch. 02

by LuvAGoodPegging on Sep 11, 2017
Transsexuals & Crossdressers

(Author's Note: This is a continuation of "Amy Finally Lives Out Her Fantasies -- Shy Amy uses her strapon on Kyle". Thanx to all who provided such great feedback. Hope you like part two. Warning: this story contains male/female strapon sex, cum eating, and as the category suggests, shemale sex. If those aren't your things, you won't enjoy this story. Love t...

Leather Shemale & Leather Wife

by LeatherKev on Sep 19, 2017
Fetish

I have always loved seeing others wear leather. I, too, love to wear leather and have a growing collection. I can't remember when it started but it seems I have always had this fetish for leather. During my first job out of college, I met a lovely young woman named Mikky. She was beautiful. Long dark hair, blue eyes, and long legs. All I could think of was s...