Crossdressing Strapon Stories

2,832 results
Orientation
Length
Source
Infinite Scroll

A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

Batman: The Masturbation Menace

by KarennaC on Sep 14, 2017
Celebrities & Fan Fiction

The Bat Signal lit the sky over Gotham City. On a hill just outside the city limits, Batman said, "Quickly, Boytoy Wonder. To the Batmobile. We have to get to police headquarters." Dildo the Boytoy Wonder wiped his mouth and stood. "What's going on?" Batman sighed. Why hadn't the sidekick temp agency sent him someone with brains to fill in while Robin was...

Encounters of a Crossdressing Slut

by KAshton on Sep 16, 2017
Transsexuals & Crossdressers

This is an introduction to my crossdressing experiences, touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever. I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like sli...

Lena et Tatiana Ch. 03

by Eltee84 on Jun 15, 2020
BDSM

She was his Maitresse. There was no doubt about it. She was his lover, she was his friend, she was his darling, honey, babes... whatever. Even when she switched she was his Maitresse. She knew that. But right then... she didn't feel it. Right then she was nobody's Maitresse. She was dominant to nobody. She was a slut. She was a bitch. She was game for whatev...

Power Plays Ch. 15

by Ice_Tease on Sep 16, 2017
BDSM

Author's Note: Thanks to TexasWriterGuy for not only editing this story and his suggestions. * Sitting on the bench behind the wheel John watched as Alayna and Janice approached from opposite sides of the boat. The sunlight off the water reflected nicely off their naked bodies. Janice walked directly to her husband giving her chest a little wiggle as she l...

The Court: Last Resort Ch. 02

by Lottiessub on Sep 14, 2017
Fetish

I was released from the stocks and ordered to stand at defense counsel's table. My hands were uncuffed and I stood where I had many times before, but midst circumstances very unlike any I had encountered in my career. The Judge smiled from the bench and welcomed me to HER Court. "Counsel, it is nice to see you...all of you...in my Court today. You are, howev...

The Gynarchic Alliance Ch. 08

by gynarchite on Mar 5, 2018
Sci-Fi & Fantasy

Chapter 8 - Finale Tolan served the women more drinks and a light evening meal as they sat in the airy, wood-panelled lounge. Lonna had him stop in front of her so she could admire his perfect, hard bottom, squeeze his balls and brush her finger past his anus. Lonna had submitted to both domwives in the household all day, and she was craving a man to domina...

A College Professor's Discovery Ch. 03

by escriterra on Sep 26, 2017
Fetish

The driver who had met Sherrie on her first and second arrivals at the Christchurch airport was grinning at her as he waited at baggage claim while she made her way through a throng of people, all who seemed intent on being the first to retrieve their luggage. "Dr. Mathison! So good to see you again!" said the dark-skinned man known only as "Catchy" to Sher...

Night at Amber's

by simple_jack on Sep 14, 2017
BDSM

Stuck in rush hour traffic, Amber lightly shook her head to ward off the oncoming drowsiness that seemed to follow every major workday. As an investment banker, the slender, red-haired 29-year-old was dedicated to becoming a partner at the firm within the next decade. However, such a goal was not without sacrifice. Luckily, she knew what awaited her when she...

Ragdoll Ch. 07

by CapriciousRain on Sep 16, 2017
BDSM

"Strip princess," Victoria commanded Violet. For the moment, Chelsea and Niobe lounged in sumptuous chairs and watched the scene play before them. It was a short time after the end of Brentwood's impromptu meeting, and the four girls were closeted away in Victoria's room. Victoria's tone was icy, yet laced with a dark sensuality. She was in a mood to play...