Sissy On Sissy Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll

Genius That He Was

by Art on Aug 19, 2017
Exhibitionist & Voyeur

Billy Bob was quite pleased with the new, or nearly new, VCR that he had acquired at the local pawnshop. It was in its original box and still had the shrink-wrapped owners manual. And, it had cost him twenty-five dollars less than a brand new one. He stopped at an electronics store on the way home and bought a few things to hook it up to the television and t...

Prankster Ch. 10

by Paris Waterman on Sep 15, 2017
Group Sex

Copyright © 2007 Many thanks to "Techsan" for graciously giving his time and effort to me in editing this and other stories of mine in recent months. As always, I appreciate your excellent support, thanks again, Techsan. Chapter 10 After letting the girls out of the van and escorting them into the warehouse, Tony made a couple of calls to old acquaintan...

Prankster Ch. 08

by Paris Waterman on Sep 15, 2017
Group Sex

Late the next afternoon, Tony met with Barely to set things up for that evening's session at Crazy's place. "You know," Barely said, "I came across something last night when I was editing the tapes." "What was that?" Tony asked. "It's best I show you, then you tell me if you want it back in. It was me, I'd keep it out. I just don't feel comfortable with...

The Vacation from Hell Pt. 01

by JamesMiehoff on Nov 27, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

Breaking with Traditions

by Canadagander on Sep 17, 2017
Loving Wives

Copyright © 2005. All characters, events, and text in this story are purely fictional, and are created by and the sole property of the author. All rights reserved. - - - - - - - - - - - - - - - - - - - - - - - Writer's Note: It's time for Canadagander to make a public disclosure, to come out of the writer's den, so to speak. 'Gander is not a real person....

Sissy Boy Secretary Ch. 05

by Hotenuf4u on Sep 19, 2017
Fetish

The whole week was spent on completing the paperwork needed for our customers. There was a lot of work and I had worked through quite a few lunch breaks, but completed the work on time. Business was getting better each week and Elaine had said that I was one of the reasons that it was going so well. Although I still stripped to my panties while in Elaine's o...

A Sissy Shopping Trip Ch. 03

by cwsissy on Sep 16, 2017
Fetish

We were quickly through the checkout and on our way again. Cindy dragging me by the hand toward the mall entrance. "C'mon, lets go. We have some more stops to make and we haven't got much time." Our next stop was a high-end shoe store just outside the department store. I had lingered outside that same store many a time, admiring the sexy heels on display i...

Sissy

by TxRad on Sep 14, 2017
Mature

I came in from work about noon on Friday. I had been gone for a little over two weeks. Pulling in the driveway, I noticed that my daughter's car was gone but her best friend's car was parked in front of the boat on the far side of the carport. You talk about a pair to draw to; those two were it. My daughter is tall, dark, and slender, Sissy is even taller, b...

Sissy Boy Secretary

by Hotenuf4u on Sep 19, 2017
Fetish

As I sit here in the outer office space of the company CO, I look like an ordinary male secretary. On the inside I'm wearing a pair of pink lace panties, at my bosses request. You see I'm really a sissy inside and my boss takes advantage of this at every possible opportunity. I've worked here for 2 years now and it wasn't always this way. My boss, Elaine, a...

Sissy Boy Secretary Ch. 02

by Hotenuf4u on Sep 19, 2017
Fetish

I got into the office 15 minutes early this morning, her panties cleaned and put on under my clothes, as instructed to do. The satiny lace felt good against my cock as I moved around the room. Just when the finishing details for the Scottsdale account were complete, she entered. She looked so sexy walking into the office, her ass swaying so nice. It looked l...