Sissy Fisting Stories

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Orientation
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Infinite Scroll

Carrigan's Kinks

by Scotsdude on Sep 15, 2017
Fetish

To those who have written to me asking to write again, I dedicate this story. It's been a while since I submitted a story to Literotica and a lot has gone on in my life since then...one divorce and one marriage. I do intend to submit some more stories over the coming months, including the long awaited sequel to Zius...I know promises, promises, but it is alm...

Slave Ch. 08

by slaveheathen on Sep 25, 2017
Fetish

Note: Story following the adventures of a bisexual submissive man. Some elements are based on my own personal experiences, some are purely fantasy. Yes, I love cock in my ass. Yes, I am slave to a Mistress who fucks my ass beautifully. Yes, a great many things that I write about we've either done or intend to do. There is bisexual sex, group sex, crossdressi...

Story to My Cuck

by Miss_Delila on Sep 17, 2017
BDSM

This is a story I've started writing to my submissive about you would exactly happen if he came for a visit in real life. It started out as a fun project and I keep enjoying it more and more. Once you make your way to the baggage claim area you will see me waving at you. I walk toward you and take both of your hands in mine and kiss both of your cheeks....

A Sissy's Day of Fun

by sayaSky on Mar 10, 2020
Transgender & Crossdressers

Part 1 It was summer break, so I was visiting home after my first year of college. My parents were going to be gone for the next few days visiting old friends. Being by myself, I went online to a hookup app and searched for a match. In my ad, along with a picture of my ass in a thong, I said I'm a young male looking to get fucked by a top. It only took fift...

I'm Billie, My First Story

by WilliamDeramus on Oct 21, 2019
BDSM

(Everybody in this story is 18+) First I created the free Hotmail account, it was a separate one from the other two e-mail accounts that I use all the time for work and to converse with friends. In a perfect world I would not care if anyone knew I was here writing stories, but I have noticed that this world is pretty far from perfect. Then I used the new e-...

Cuckold Husband Ch. 04

by lace_lover on Sep 25, 2017
Fetish

Having got home from my very humiliating shopping trip, things had progressed quickly. Katrina had teased me all the way home in the car, making comments like, "I'm gonna fuck you tonight like the slut you are," and, "Come on admit it, you want to be my bitch, don't you?" I was embarrassed to answer but my caged cock twitched at the thought and was becoming...

Like a Dream

by Scotsdude on Oct 15, 2017
Fetish

As I arrived at work that Monday, I knew that it would not be a normal day. My throbbing head was a distinct reminder of how my weekend had been. Saturday night was a blinder. It was my friend Kevin's 30th birthday, and as such, we decided to make it a bit of a blinder. It started out with paintball, went on to karting, dinner, and a strip club. Prague's st...

Amazon Sissy Jock

by Sissyhalo on Mar 21, 2018
Transsexuals & Crossdressers

All parties involved are over 18 years of age. *** It started me going to a party. Now that's not unusual because I'm popular, I've always been popular like ever since junior high. I shot up like a weed getting tall and my dad worked me out while I was going through my growth spurts and had me in lots of stuff like to round me out before I got into footba...

Kasey's Confession Ch. 11

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

On Saturday morning, Mr. Smith had me start my day by writing a letter to Nancy. "Dear Nancy," I wrote. "I am sorry for all the trouble I may have caused you with my conflicted emotions. I understand now that the reason I fell in love with you was because you were a woman, because you were the only woman who accepted me as I was. I understand now this was b...

Whore of the Dragon

by Conan The Librarian on Feb 19, 2020
Fantasy

There, amongst the remnants of the dead race, where their greatest queen reigned, two dragons lie dormant. One of pure evil, one of pure good, both yearning for a vessel, both lusting for a mate... She may be adequate for that purpose, our forlorn child... We shall see. "Silence, fools. We are close to the inner sanctum." The two mercenaries exch...

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