Crossdressing Strapon Stories

2,832 results
Orientation
Length
Source
Infinite Scroll

The Transition Ch. 01

by Quantarx on Jun 8, 2020
Transgender & Crossdressers

Greetings and thank you so much for choosing to read my story. This is intended to be a multi part series so bare with me as I try to develop the characters and lay down the backstories. As always, Your feedback is always essential in the development of the story going forward. Please leave a comment down below * I Had been Married for about eight years w...

A Wedding Night Pegging

by pwlrstr on Sep 12, 2017
Fetish

"It would be more of a big deal if it was the first time," Jon had said, instantly regretting that it sounded a bit negative, when his fiancée Naomi had asked if he was looking forward to their wedding night. "I mean, I don't really believe in saving yourself for marriage or any of that crap. I think it's definitely been a good idea to have lots of sex first...

Ugly Duckling to Sissy Princess Ch. 02

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 1) My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy c...

All Black Men Love Strapons

by Samuelx on Dec 12, 2018
BDSM

My name is Elisabeth MacLeod and I'm a sex therapist. I don't look like it, though. I'm a six-foot-six, bodacious dame with long blonde hair, pale green eyes and alabaster skin. Yeah, I'm a tall woman. One of the tallest in the Boston Area. And I am proud of it too. Just call me the Scottish Giantess. People come to me to help them solve their problems. Espe...

Jenn's New Job Ch. 06

by marquisdeslut on Sep 14, 2017
Group Sex

A few days later, like Jenn had asked, I took the afternoon off work and met her on the street outside of our apartment building. She walked us a few blocks away, along an unusual route. Jenn stopped in front of a large house. "Here." "Here what?" "The house. The solution to all our problems. I bought this house!" "That's great! But I don't follow." "I'm...

Sissyhood of Travelling Panties Ch. 01

by daddyslittlebitch on Sep 14, 2017
Transsexuals & Crossdressers

Chapter 1: Alex A pair of red satin panties lay on the bed. They were boyshort style with little red lace bows above the crotch. Very sexy and very slutty. Helen ran her fingers along the soft, smooth material. She was dressed in a black lace garter belt holding up thigh high stockings, her large, round breasts, still firm at the age of 45, stood out naked...

Several Stories from Somewhere Else

by Freyasbearn on Mar 11, 2018
Fantasy

This is the landing page that will take you to the several stories re-archiving here. I am also using this section for new stories with the same themes as my other stories. That way I don't have twenty different stories all over the place that cover the same stuff. You can get it here. If you want to add on, or take a story a different way-- please, please d...

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Just Another Fantasy Story Of Mine

by SoNaughty on Mar 17, 2020
Erotic Couplings

I made a date with a guy from Heated Affairs and I had told him I wanted to fulfil my fantasy of having a man wear a strapon on to fuck me! He wanted to help me fulfil my fantasy. So we went to adult store and bought a strapon and came back to his place. We walked into the door and I turned toward him and leaned toward him. He leaned down and started french...

Fulfilling all My Fantasies Ch. 01

by classmate1119 on Apr 23, 2019
Transgender & Crossdressers

"Last chance to change your mind, Cristi," Jalen said. "It's probably the most outrageous one so far! Not that I'm worried, of course, but you never know what else might happen... " I reapplied my lipstick in the reflection of the club's glass entrance. "Hey, we spent too much time preparing for this. Don't back out on me now, Jalen!" I threw him a coy smi...

Mike Meets Jenna and Her Strapon

by Boxlicker101 on Sep 14, 2017
Toys & Masturbation

One Friday afternoon, Mike Harris was about to leave the school when he was stopped by Monica, accompanied by another young woman. "Hi, Mike. I hope you didn't have any other plans for tonight because you have a date with us." "Us?" "Yeah, me and Jenna here." Monica's companion, even though she was smiling, was thin and unattractive. "Glad to meet you Mik...