Shemales Stories

429 results
Orientation
Length
Source
Infinite Scroll

Cassandra Ch. 01

by AngelCherysse on Oct 13, 2020
Transgender & Crossdressers

Cassandra is a tease, a flirt, a slut, a girl who lives very much for the moment. Unconcerned with propriety or fashion trends, she dresses in clothes that go right for the jugular of a fetishist's libido. Spandex, leather, latex, spike heels, corsets, overdone hair, make-up and fingernails - these are her stock-in-trade. Cassandra flaunts her outrageous bod...

Finishing School for Shemales

by Imogen_TS_2020 on Sep 25, 2017
Transsexuals & Crossdressers

Mistress K looked at the school report and smiled. She wouldn't describe herself as an evil bitch, but plenty had. She was proud of her position. Headmistress of the Finishing School for TGirls. So many beautiful shemale girls had left her careful administration and gone on to happy lives, or sometimes porn careers. Sometimes they had been bought outrigh...

My Treasure

by Tetris07828 on Sep 19, 2017
Transsexuals & Crossdressers

I drive truck. Have all my life, ever since I was a kid. My dad took me to my driver's test in a jacked up Ford 150 pickup and had to explain to the examiner that this is what I practiced with. Since then I got my CDL license and have been driving the big rigs. Got to admit, I love the life. You have to love it or you're going to be one miserable bastard. Th...

Shemale Tales: The Christmas Party

by silkstockingslover on Sep 2, 2017
Illustrated

Summary: Young woman discovers the perfect man... a woman with a dick. Note 1: This is a Christmas 2016 Contest Story so please vote. Note 2: Thanks to TexBeethoven, Robert, Dave, and Wayne for editing. Shemale Tales: The Christmas Party I'd been working at the firm for only a couple of weeks and originally wasn't planning on attending the staff Christ...

Wannabe Cuckold Gets Found Out

by tombrennen on Jan 20, 2020
Fetish

A little about myself before I start the story. A trim 35 year old man that would probably be diagnosed as a sex and porn addict. As long as I can remember, I've been extremely sexual. Starring at cleavage and tight pants, led to porn mags and the occasional video, led to the internet. Once the internet exploded, so did my sexual fantasies. Shemale porn, and...

Fetish & Fantasy Pt. 01

by GavinIsaNuisance on Jul 13, 2020
Transgender & Crossdressers

This work is completely fictitious, any similarities to any persons living or dead is purely coincidental and entirely unintentional. All persons depicted in naked/sexual acts are 18 and up. Down and out aspiring model Taran Kilkenny becomes the hottest commodity in an escort service for trannies! But first he's gotta get trained by his new and domineering b...

Finishing School for Shemales Ch. 02

by Imogen_TS_2020 on Sep 25, 2017
Transsexuals & Crossdressers

Please note, all characters portrayed in this story are over 18. * Davina hurried down the hallway, her books clasped in front of her heavy breasts to stop them jiggling as she ran. It had been almost two weeks since she had truly given herself to Mistress K in the beautiful, imposing headmistresses study, drinking the transgendered woman's seed from anot...

The Lost Boy Ch. 04

by DamienDeath20 on Sep 25, 2017
Transsexuals & Crossdressers

A.N. Hello errybody! This chapter was kind of a special treat where the commissioner gave me free reign for the scene so it's near and dear to me :3 The Following Contains: Sexy/Kinky Librarian dickgirl fucking a bottom femboi senseless because that's hot x3. If you're not a fan of such things, avert your delicate eyes! Other than that I hope you all enj...

My Submission to Laura

by sub_hubby_steve on Sep 26, 2017
Loving Wives

1 The Reveal I arrived home early from work and an envelope addressed to "My Submissive Slut" greeted me at the door mat. I was shocked. Who was it from? Who was it for? I picked it up, it smelt of my wife's favourite perfume. The adrenaline started pumping through my body. Who has Laura been submissive for? More to the point, who has she been a SLUT for!?...

Fetish Pro Wrestling Ch. 02

by VexingVanna on Jan 28, 2020
Fetish

Authoress' note: Thank you all so much for the reviews and comments! This is meant to be an intersection of story and sex, with "real" and meaningful characters, both "on-screen" and "backstage". Think of this like an episodic multimedia show, kind of like if WWE seamlessly blended Raw or Smackdown with Total Divas and a "reality" show backstage. It's not al...