Sissy Fisting Stories

10,571 results
Orientation
Length
Source
Infinite Scroll

Money Shot Pt. 02

by GavinIsaNuisance on Jul 27, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and completely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Tanya introduces a newly sissified Danny into the world of erotic photography which gets them into a hot offer they can't refuse. Author's Note: So, I establ...

Castro - Shemale Goddess Pt. 01

by Llawmaker on Mar 7, 2018
Transsexuals & Crossdressers

Chapter 1 -- Well Met Nobody would have believed the scene was true, her slender, smooth and tanned legs crossed in such a deliberately provocative way as to reveal a glimpse of crisp white panties. Her tightly fitting, classically styled little black dress cut to ensure firm large breasts were displayed to maximum effect through the low neck. Her blonde h...

Life's Changes Ch. 08

by Scribler on Sep 16, 2017
Fetish

I awoke to the sense that something was different. I realized I wasn't in my own bedroom. The only light was coming from somewhere behind the wall. Then I smelled the scent of fresh brewed coffee close by. I felt a warm body next to mine that held me in its grasp. It was female. I could feel the swell of her warm breasts against my back. And the faint smell...

Fisting and Wine Bottles

by 57hangar on May 12, 2020
Fetish

This is an account of a true event.... Started playing and stretching with a new friend recently. She contacted me through a website, talking about her desire to be fisted. We talked about our fantasies and experience. She really wanted to have her pussy fisted up to my wrist for the first time and have it stretched. Anal play was also something she wanted...

Mistress Viagra Pt. 01

by Njstraponlover on Sep 13, 2017
Fetish

This story is 100% pure fantasy. None of it ever happened. If you are offended by stories of a mature nature containing references to bondage and humiliation, please do not read. This is fiction!! ***** I had been chatting with a new online mistress for a number of months and during that time she had me buying all kinds of sexy woman's cloths, new sex toy...

Into The Abyss: Vaginal Fisting

by Kael01 on Sep 26, 2017
How To

A bottle of water based lube and a pair of gloves. These are the basic tools that you need for a lot of different endeavors. Medical Play, anal play, putting new grips on your golf clubs, and replacing the washers on that leaky faucet are just some of the wonderful uses for these two tools. The one that we are going to discuss today is fisting, specifically...

How I went from Domme to Slut Ch. 06

by Ms_Allison on Jun 26, 2018
BDSM

I would like to thank the darlin mymantoy999 for his editing and insight and in particular keeping my math and thought process straight while writing these! ***** As amber had suggested she and I settled into our new normal relatively quickly. Now on top of waitress duties every other week, house cleaning trips and the random frustration amber experienced...

Vaginal Fisting

by Hand on Sep 26, 2017
How To

Editor's Note: The opinions and/or information in the how-to section are not those of Literotica.com, and anything you do with this information, you do at your own risk. Thank you for reading, and enjoy! There are many people who have never heard of fisting, or have no idea what is really involved. There are two types of fisting, vaginal and anal, this arti...

Draining the Slave's Balls

by MsCarol on Oct 12, 2017
BDSM

"For the last time slave, stop asking me for an orgasm," exclaimed Mistress Gail. "I don't care that they are swollen with cum, that they are sore from being spanked last night, or that you have not been allowed to cum for two months now! What do you have to say to that?" "But Mistress it has been four months since you last allowed me a release! I endure ev...

MilkTitty Farms Ch. 02

by BlackMadonna on Sep 19, 2017
Sci-Fi & Fantasy

CHAPTER 2 – ROOMIES Before any plotting or planning to win the affections of her pretty bull girl, Kelly had to get settled in, and so turned with the rest of the group in search of a cozy bunk and a place to store her things. True to their nature, most of the other dickgirls had already begun pawing at one another and breaking off into tiny clicks with wh...