Shemale Boss Stories

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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...

Jimmy Olsen Shemale Bimbo Ch. 01-02

by tawnysuede on Sep 17, 2017
Celebrities & Fan Fiction

Chapter 1 - Junior reporter on the job! Jimmy ran the brush through his shoulder length hair one more time and stepped back to admire himself in the full length mirror. The wig looked good. It was the same wig he wore each time he dressed up. He took the cap off of the lipstick tube and applied a generous coating of the scarlet wax to his lips, and then bl...

A Shemale Christmas Carol

by ThomX on Sep 16, 2017
Fetish

I got a job working as a mall Santa at the local mall during the Christmas shopping season one year. It had been a real shitty year for me. My wife of almost twenty years left me for a younger man, I lost my other job due to layoffs and, on top of all that, my doctor diagnosed me with high blood pressure (gee, I wonder why?). So believe me when I say the las...

How I Met My Shemale Pt. 04

by Eroticalover1968 on Sep 25, 2017
Group Sex

Ever hear of the expression, 'Led around by the balls'? Well, it brings back visions of an epic fuck up. Whose fault? It hardly matters. Joyce peeled around the corner, cast a delirious water-eyed glance at me. She drove over a curb—our suitcases jostled around like they were fucking. "What the hell just happened? How does Cheryl have a cock? She put it in...

Transformed Into A Shemale

by girlboybootsie on Sep 13, 2017
Fetish

I was 18 when I first had sex with a man. This is the story.... I am a very hot looking guy. I say that knowing that some may consider me vain, or arrogant, but over the years I have had so many women and men tell me how fine I am, that I know it is true. I am 35, blond and blue eyed, 6'1," 180lbs, with a tan athletic body and a 7" beautiful cock. I have be...

Sister's Shemale Friend

by silkstockingslover on Sep 12, 2018
Illustrated

Sister's Shemale Friend Summary: Family seduced and dominated by an irresistible shemale. Note 1: This is a Summer 2018 Contest Story so please vote. Note 2: Thanks to DarkBreezly for creating the pictures in this story. Note 3: Thanks to Tex Beethoven, Robert and Wayne for editing this story. I came home from work a couple hours early, as our manager...

Pam's Gangbang Experience

by majicman21 on Oct 14, 2017
Group Sex

Author's Note #1: This is a continuation of 'Pam's Shemale Experience' from the Transsexuals/Crossdressers category. Although reading those stories is not necessary to appreciate this one, it will enhance the experience. Either way, enjoy. ***** The splashing in the hotel pool provided an aural backdrop as John read his Kindle, learning about the history...

Gremlins Crossover

by Maxout Hearts on Apr 22, 2025

Introductions The names the characters below this sentence belong to @PearlteaRizzy also go by @MiiyaUwU_EN at Twitter. Please her show some love by following at Twitter or go read her webtoon comic The Beevs. Ash muller age: 30 redhead femboy programmer. Gabby Jarvis-Park age: 28 livestreamer tay's girlfriend/roommate. Tay Cunningham age: 30 web designer ga...

A Chance Encounter Ch. 02

by grover10 on Sep 14, 2017
Celebrities & Fan Fiction

Chapter 2 (Pornstars, Fan-based, Transsexual, Shemale and Female, Seduction, Creampie, Fantasy-based, Masturbation, Lesbian, Threesome, Orgy) Characters (in order of appearance): Julia Ann, Vaniity, Alina Li, Rachel Starr (Non-Sex), Randy Spears (Non-Sex), Elsa Jean, Diamond Jackson, Alura Jensen, Heather Hunter, Simone Sonay, Venus Lux, Brandi Love (Non-Se...

Genie Chronicles - Make a Wish 00

by BebopJet on Sep 25, 2017
Sci-Fi & Fantasy

A big thanks goes to Joe Brolly for the original Genie Chronicles. As many people have done, I'm simply taking his original story format and giving it a twist. Fair warning, lesbian and futa (shemale) sex will feature heavily in this storyline. * Vicky wiped a thin layer of dust from the back shelves of the University of Texas central library section of E...