Master Sissy Stories

61,161 results
Orientation
Length
Source
Infinite Scroll

A Shemale Vacation Ch. 01

by britneyfan on Sep 12, 2017
Transsexuals & Crossdressers

I was eighteen, naïve and horny. After graduating from school a group of us decided to head to Europe for a last trip before having to enter our real adult lives. It was a chance to get completely drunk and have lots of wild sex. At least, that was the idea in our simple teenage minds. As for me, wild sex was something I wasn't exactly familiar with. I was s...

My Second Piece of Ass Ch. 27

by Fable on Sep 13, 2017
Erotic Couplings

On Monday morning I overslept. Having had my bedtime delayed by Petri’s telephone call and having it interrupted by Ollie’s telephone call and being awakened again by Laura’s hand around my cock in the early morning gave me three good reasons to turn off the alarm and go back to sleep. Petri’s call came early and was welcome. She was alone and wanted someon...

It Finally Happened!

by d_p_sweetie on Sep 17, 2017
Loving Wives

The car came around at about 9 o'clock for her. My stomach was a bundle of nerves waiting up for this, but no matter how many angles we discussed, this was possibly the best option we had to save our marriage. I looked over at Lauren and smiled at her fresh, present, and sexy as the day I met her —sexier, even, if it was possible. She blushed a little, look...

Kasey's Confession Ch. 21

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

Neil and Ted collected themselves, and before I could position myself on my knees in front of Tony, they made it clear they were leaving. I got up from the floor, steadied myself in my heels, and walked with them to the door. "Catch you later," they intoned to me before turning to Tony and saying, "We'll be down at McMurphy's later if you want to meet up."...

Kasey's Confession Ch. 07

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

Whatever Derek had given me, it lowered my inhibitions and made me very eager to give into my fantasies. The voice inside that told me to run from the situation was getting fainter and while I was somewhat panicked by Mr. Smith's stated intention to "break" me, a larger part of me was intrigued. It wasn't like I hadn't been with men before and it wasn't like...

Liz and John Solve Their Problem

by Quietoldie on Sep 12, 2017
Fetish

Liz is getting very frustrated. She has been married to John for four years now and there are things in their marriage that are not quite right. They've bought a house with help from both their wealthy parents. John has good job and they could easily manage without Liz's wages. Liz wants to start a family but she knows that you cannot do that until she irons...

My Michelle Ch. 02

by d_p_sweetie on Sep 12, 2017
Loving Wives

The next day, I think we both expected to take it a little easy. Our little foray into sexual openness had been thrilling, but I was nervous about where it would go from here if I didn't step on the brakes a little. I'm sure Michelle was having similar thoughts. We talked about it on the way out of camp. I asked her, "How do you feel, baby?" She said, "Oh,...

Dominated By and Older Couple

by Icantthinkofone on Sep 17, 2017
BDSM

Author's note: This story is a fictional fantasy. I wasn't sure how to categorize it. There is gay male sex, although there is a female involved in the story. Since it's about submission, I thought I'd put it in the BDSM category. * I had been surfing the internet for weeks, looking for a dominant male or couple that wanted to play with a bi curious male....

The King and I

by SarahConnor210 on Sep 14, 2017
Celebrities & Fan Fiction

The King and I - A Can of Peaches Finally, my mother thought I was ready to take on projects of my own. She's a seamstress, she's been teaching me the craft for as long as I could remember. I am now 22 years old and have made a living sewing and designing on my own, for 2 years. My mother generally didn't like my designs. She's very old fashioned and woul...

Sissy Secret Exposed Ch. 01

by LtBroccoli on Jun 5, 2018
Loving Wives

Leaning across the bed to kiss her husband goodbye, Amy noticed her own naughty scent still clinging to his chin. "How lazy," she thought, "I really need to teach Mike how to clean up after sex." Fortunately for him, there was no time for admonishment this morning. She had a big meeting with the CEO in less than an hour and a crucial dinner with clients toni...