Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

Handyman Pt. 05

by lovedart54321 on Sep 28, 2020
Transgender & Crossdressers

I arrived at my hotel and got checked in. There was a bar downstairs in the hotel, so I thought it might be nice to have a drink before I went to bed. I had brought my Rachel clothes with me, at least, my lingerie and make up. I didn't really have a dress, but I had bought a shirt that definitely looked a bit girly, and with a pair of jeans, and my hair done...

Not a Man Ch. 03

by rarmons on Sep 19, 2017
Transsexuals & Crossdressers

My alarm rang at 7:30 am, and for the second morning in a row, I woke up with my head pounding like someone took a hammer to it. I sat up, and looked around in confusion. I was still dressed from the night before, back in my own bed, with no idea how I got there. The memories slowly came back to me, while I turned on the coffee maker, drank some water, and...

The Waxing Ch. 04

by thecuriousgeorge on Sep 15, 2017
Exhibitionist & Voyeur

This story is part of the series "The Waxing." It actually picks up after part two, from the point of view of John's wife Jane. You won't miss anything by skipping the other parts of the story, except for some more hot sex, but the twists of the story will make more sense with the background provided by the other parts. ***** Saturday Morning I woke up e...

Cherry Hill Ch. 03

by Dark_and_Red on Sep 14, 2017
Novels and Novellas

George Krest awoke to first the feeling, then the sound, of a pair of lips racing on his rigid cock, giving him a sloppy blow job. He didn't need to open his eyes to know the tongue begging cum from his balls was his foreign exchange daughter, Ava. Ava was the hottest little brunette to have come from Bohemia since the song from Queen, and she was above and...

Code Name Tequila Ch. 03

by Travel_by_day on Sep 13, 2017
Transsexuals & Crossdressers

The same day that Ria Ortega boarded a plane to head to Argentina, Jarvis Cleethorpe was rushing down a hall in the Langley, Virginia headquarters of the Central Intelligence Agency. He had a meeting with the man known simply as "Black Oak," the man who was in charge of a number of projects at the CIA, including the one to identify and eliminate the South Am...

Busted Wearing Panties Ch. 01

by tonyl65 on Sep 25, 2017
Transsexuals & Crossdressers

I went through forty-five years of my life as a single man, no one to answer to but myself. I watched my friends marry, have children, and get divorced. I kept hearing the same old stories, 'money problems', 'she wasn't the same in bed after the kids came', 'we are too tired because of the kids', and the best of all 'we fight too much over money and the kids...

Consent Ch. 01-02

by sublocked on Sep 25, 2017
Transsexuals & Crossdressers

Author's Notes: (1) I start slowly, and build up, so be patient. (2) And please, please...erotica is in the minds of writers and readers. One man's erotica is not necessarily another's. (3) This is for cross dressers and fetishists, and it is fiction. There are sometimes no boundaries on where one can go in fiction, so, you trolls out there, just park log...

Changing Room Prank

by Littleblackdress54 on Sep 25, 2017
Transsexuals & Crossdressers

My two best friends and I were walking through the mall, as we did most Saturdays. We lived in a pretty small town, so this was the closest thing we had to entertainment outside the house. We passed through the women's clothing stores, taking a shortcut to get to our favorite food stand. After ordering, we sat down in the corner of the hall, minding our busi...

Good Little Bitch Pt. 01

by Baron_Cumhausen on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 1: Halloween "Seriously!" my girlfriend Claire declared, "Nothing faggy or anything like that, just yoga outfits and a little makeup, y'all will be so cute!" It was Halloween night in Austin, always a major event down on Sixth Street with ten thousand people bar hopping and mingling in the street even when it fell on a weeknight. Today was Friday...

Jay's Sex Club Adventures Ch. 09

by WhiskeyIsGood on Sep 13, 2017
Transsexuals & Crossdressers

The day after the party, I woke up in the bed where I had slept with Christy the night before. But I noticed immediately that she was nowhere to be found. I groaned, sitting up and rubbing my head... I had a serious migraine, and my stomach was churning. The beginnings of one of my typical, yet still hated, hangovers. Certainly not shocking though, conside...