Master Sissy Stories

61,161 results
Orientation
Length
Source
Infinite Scroll

Kitty-Chan: Freshman Year Ch. 01-04

by Foreverhiskitty on Jul 28, 2020
BDSM

We'd already been going out for five months when I let my boyfriend, at the time I knew him as Will, take my virginity. We'd been each other's firsts and it had been the best feeling ever. At first I thought losing my virginity, in the middle of the woods would be weird but he definitely changed my mind, he was so sweet and passionate, if I hadn't known him...

Reversals Ch. 07

by RachelClark on Sep 14, 2017
Fetish

Sisterly Advice Eric toiled in the kitchen, scrubbing the bottom of the kitchen sink for the second time that day to remove some gunk he'd missed earlier. Rinsing and drying followed. The sink needed to shine for Julia's inspection when she returned home from work. Perfection would be demanded. It had been three days since Julia had declared that they were...

My Saturday Night: Edging

by honey28 on Sep 16, 2017
Transsexuals & Crossdressers

Dear Fellow Literoticans, This is the third installment of my non-fiction series (see "My Friday Night" and "My Saturday Night"). While it is obviously intended to turn you on, this isn't just a 'stroke story,' so if you're looking for a quick way to get off, you might want to move along. That said, this story contains cross-dressing (obviously), femdom, r...

Turning Summer Ch. 1

by monika ikon on Sep 12, 2017
Transsexuals & Crossdressers

I remember holding up that first tiny pair of swim trunks in disbelief. "You want me to wear this?" I said. "Outside?" "Of course silly," Kathy said. "Don't you just love it?" The bathing suit consisted of two tiny triangles of white nylon that hardly looked big enough to cover what by law had to be covered. I was used to my oversized blue boxer-style sw...

Susan and John's Return Ch. 01

by dan57 on Sep 17, 2017
Loving Wives

Chapter 01 Several Years Later By Jill York and dan57 Susan and John had fallen under Mr Gupta's domination for years now but routine had slowly eroded his lust for Susan and his pleasure when he humiliated her husband John. _ _ _ Susan and John had settled down so nicely. They were now in their early thirties and the trials and tribulations of earlier...

Michelle My Hotwife Ch. 02

by KINKYCanada on Sep 13, 2017
Group Sex

When I awoke the next day, I was amazed at how relaxed I was. I looked over at Michelle and saw that she was sleeping soundly, as she usually was as I got up three hours before her most days. In the shower, I jerked myself to one of the best finishes ever. I had a hard on all the while I ate breakfast and made my lunch. I went and got dressed and looked at m...

Maid for Pleasure

by Sucker4Boobies on Sep 25, 2017
Fetish

Life was going pretty well for Agnessa. She had come to the United States 5 years ago from Ukraine and had successfully gotten her green card. After working at her uncle's custodial company, she was able to get a cushy job as a live-in housekeeper for a wealthy family in Delaware. Mr. Richards was the owner of a property investment company, and lived in a l...

My Little Penis and Me Ch. 03

by mceh501 on Sep 13, 2017
Fetish

(((Note: All Characters in the following story are based on real people in my life, however it is not a true story. All the character's names are changed. All of the following characters are over 18. This story is about humiliation and a person with a Napoleon Complex, so to speak. If sph isn't your thing, move on.))) * It's been a few months since I lost...

Marilyn: Going Your Way

by BrettLynn on Sep 13, 2017
Transsexuals & Crossdressers

Welcome to the latest installment of my tales of pure, unadulterated lust. Wait a sec, I’ve just adulterated it. Oh well. I’ll keep it short and sweet. After all, I have enough problems with people bashing my work. No disclaimers. If you don’t have the good sense to realize that this my work, and that if you’re gonna make money off of it, it is my legal righ...

Mormon Chicks Like Big Black Dicks Ch. 02

by MormonChicks on Sep 16, 2017
Loving Wives

Interracial sex begins in later chapter. Fucking Joni was like a dream. I could not imagine I could be that into her and that slim body. She had wiped off on a handful of tissue, dressed, and hurried home. It was odd that after what we had just done she had put her Mormon garments back on under her clothes. I had cleaned off the leather couch where we fu...