Crossdressing Strapon Stories

675 results
Orientation
Length
Category
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Infinite Scroll

Marion Turns Me Out Ch. 02

by jomar on Sep 13, 2017
Fetish

If gentle femdom, crossdressing, strapon and male-male sex isn't to your taste, please back out and try one of my other stories. And let's imagine this is set in a world where unprotected sex is safe. ********** It was looking to be a glorious day. Marion and I were on vacation in the tropics at a five star resort. We started the day with Marion touching u...

Marion Turns Me Out Ch. 01

by jomar on Sep 13, 2017
Fetish

Marion Turns Me Out Ch. 01 by jomar If gentle femdom, crossdressing, strapon and male-male sex isn't to your taste, please back out and try one of my other stories. ********** "There, baby, that does it. Your toes will be dry in no time. A nice shade of mocha. Do you like it? It'll go perfect with your new bathing suit." Marion put the lid on the finger...

Tony and Alicia Celebrate Halloween

by Ice_Tease on Sep 16, 2017
Fetish

Author's note: The Tony and Alicia stories are more about experimentation between a loving couple than hard core stories in a certain category. If you are looking for a hard core crossdressing story this is not the one for you. If you want a story of a guy who will do anything for his girl to include dressing as a hooker and strapon sex then please enjoy it!...

Billy's Sissy Adventures.

by Trom1806 on Aug 21, 2023
Interracial

Billy's Sissy Adventures. Adventures of a young white sissy guy in sunny California and maybe somewhere else... Synopsis You are Billy Atkins, a white male student at Hayne College in Hautenville, California. Chapter 1: Introduction You are Billy Atkins, a white male student at Hayne College in Hautenville, California.......

Slave Ch. 09

by slaveheathen on Sep 25, 2017
Fetish

SLAVE Note: This is about a bisexual submissive man and his journey as he explores his sexuality. I put it in the fetish section because that seems to be the best fit. There is piss and scat. There is bondage and crossdressing. There is fisting. There is group, gay and bisexual sex. There is non-consensual and reluctant sex. There are even elements of reali...

Slave Ch. 08

by slaveheathen on Sep 25, 2017
Fetish

Note: Story following the adventures of a bisexual submissive man. Some elements are based on my own personal experiences, some are purely fantasy. Yes, I love cock in my ass. Yes, I am slave to a Mistress who fucks my ass beautifully. Yes, a great many things that I write about we've either done or intend to do. There is bisexual sex, group sex, crossdressi...

From Submissive to Slave Pt. 01

by HerBetaBoy on Sep 25, 2017
BDSM

So I sat there, my wrists and ankles bound to the chair I was sitting in. My mouth forced open by the pink ball gag wrapped around my head. My cock, as pitiful as it looked at the moment, was locked in its cage covered by pink lace panties. The view in front of me was both humiliating and exhilarating at the same time. My wife of 4 years was on her back, her...

Slave Ch. 11

by slaveheathen on Sep 25, 2017
Fetish

SLAVE Note: I have no idea if a resort like the one in this chapter actually exists, but damn I'd love to go if it did! If you haven't read the previous chapters, I'd suggest you do, as it would help to understand the characters better. This story is about a bisexual man who has completely submitted to his Mistress. It contains scenes where he has sex with...

Undercover Mistress Pt. 02

by nexomorph on Dec 2, 2019
BDSM

The first part was a bit raw. Sorry, I rushed it a bit. Read it if you want the plot. In this part I cut to the main thing. The series will contain all kinds of BDSM stuff and fetishes Have fun! *** I was in front of woman of my dreams. Aurora. Mistress Aurora. In black corset, garter belts, stockings, black thong, glassy high heel platforms, oriental hair...

Life as a Gooner

by Yelawolf on Feb 18, 2024
Bisexual

Life as a Gooner A guy life as a porn obsessed loser Synopsis You are a Gooner. A person who loves to masterbates to porn nonstop. Will you fall deeper into your addiction or finally lose your virginity Chapter 1: Introduction "Come on {mc}. Me and Trey are going to shoot some hopes down at the YMCA. You need to stop d......