Strapon Sissy Stories

8,068 results
Orientation
Length
Source
Infinite Scroll

Commander Murphy's Woman

by Grey Eagle 286 on Sep 13, 2017
Romance

Commander Andrew David Augustus Murphy, U.S. Navy (Retired) sat in his lounge chair and watched the Fox News Channel. He was not pleased with what he saw. He was disgusted with the way the war in Iraq was going. Having a fair amount of experience in the Mid-East he was of the opinion that bringing all the factions together in a common government was next to...

Killing Daddy Blue

by WickedDrX on Sep 12, 2017
Novels and Novellas

Wednesdays were always boring for Holly, and this one was worse than most. Her usual trade didn't hit the streets until the end of the week when they got paid, or until the welfare checks came. This wasn't the week for the welfare checks. It was cold, and there was a light mist falling that promised to turn into snow very soon. She could move up a few blocks...

Birthday Present Pt. 01

by donnaallure on Sep 18, 2017
Transsexuals & Crossdressers

Birthday Present or (I've Looked at Love from Both Sides Now) Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all about the exchange and nothing else was said about my birthday. The day arrived and I got home from work exp...

Flowers in the Heart Pt. 02

by JimBob44 on Sep 15, 2017
Transsexuals & Crossdressers

*Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. **Author's Note: This has an alternate ending to 'Flowers in the Heart.' It read the same as the original posting, until page 4. After posting the story, I realized that Scott was just a little too quick to accept his girlfriend's differences, especially...

Coming Together

by davepepperbury on Feb 25, 2019
Novels and Novellas

"Get that down you," Suzi said, "and tell me all about it." Linda took a long swig of the chardonnay, and sighed. Where to begin? The trouble was she had so much going on, and none of it was really a problem, on its own. There were no real money problems to speak of. Yes, she was doing two jobs - part-time at the school, and these occasional PR events with...

Huntress of the Fallen

by GayTripper on Oct 6, 2020
Erotic Horror

+++++ Huntress of the Fallen +++++ The following tale is my entry in the 2020 Halloween Story Contest. It acts as both a sequel and the final act of a trilogy that began with the 2016 Halloween Contest First-Place Winner "Sisters of the Fallen" and continued in the 2019 Halloween Contest First-Place Winner "Redeemers of the Fallen". I hold no expectation of...

Anna's Next Husband

by glossophile on Sep 25, 2017
BDSM

Paul turned up the collar of his light jacket and stuck his hands in its pockets to ward off the chill of the bitter wind that had come with the late November dusk. This part of the city was unknown to him. He had been walking the streets aimlessly since mid-afternoon trying to recover after having his heart and dreams shattered. The day had been warm and s...

A Video of Her Husband Masturbating

by escriterra on Sep 12, 2017
Erotic Couplings

"Oh, damn, babe, that is so hot," Brad panted, his eyes fixed to the big-screen HDTV in their den. One arm was around his beautiful, nude wife, Cheryl, and his other hand was slowly stroking his erect cock. "Mmmmm, it does look inviting," Cheryl said breathily, tugging on one nipple as she lazily traced wet circles around her clit. They were seated on thei...

The Dog Whisperer

by MetaBob on Oct 6, 2020
Fetish

1. Introductions I was on the trail early; the heat and inevitable sunburn of midday get unbearable here. I didn't see anyone for several minutes and hoped for a brisk pace, 6.5 miles in two hours, but my parents' dog Nicky would help; she pulls like a locomotive. Nicky is a 4-year-old shorthaired pointer, rail thin with a big chest and ludicrously fast, t...

The Very Best of Friends

by xelliebabex on Sep 13, 2017
Erotic Couplings

Authors Note: This is my entry into the 2016 Nude day contest. It is slow to start but has elements of both heterosexual and lesbian sex. I understand that long stories are not for everyone but if you manage to read all of this epic effort, please vote and comment. Thank you. ~ellie * Joanna pulled up in front of the pretty little riverside house and got...