Sissy Fisting Stories

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Infinite Scroll

Simon Sissy Slave Ch. 03

by Timewarp10 on Jul 30, 2019
BDSM

Mr Berne watched with satisfaction as the sissy paraded in the post room. Sissy walked gracefully in high heels. His ballet training made it easy. He knew how to walk like a woman. He had practiced, and he could walk with a book balanced on his head. It gave him poise, and the high heels gave elegance to his calves. The skirt was short enough to look slutty,...

Futa Island

by Kazza on Nov 18, 2019
Transsexual

This story is designed to be played as an interactive erotic adventure. For the best reading experience, please select the 'start game' button over on the right of the screen --> Futa Island was considered a myth for decades, a tall tale whispered amongst tipsy sailors in the dark corners of port taverns. The rumors spoke of a hidden island filled with...

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AliExpress and Sissy Downfall Pt. 04

by His_fag_wife on Dec 30, 2017
Transsexuals & Crossdressers

As Tim added inch after inch, slowly taking his time, stretching his new slut, driving deep into Emma's tight twitching arse, she moaned with the pain like a wounded animal. He loved the supremely tight fit as he slid forward into her, bit by bit. His sweaty ball sack finally rested on Charlies face, each of his big balls settling into Charlies eyes sockets...

Runt of the Litter

by grimbous on Oct 9, 2017
Transsexual

(This story involves a lot of humiliation of the main character, futa on male action, incest, and other fringe fetishes. If these aren't your thing turn back now. I also wanted to give credit and thanks to the artist Mafen for the above picture which helped inspire this story.) The hall is quiet. You were pretty sure nobody was at home. You creep carefully d...

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Jack and Jill Pt. 03: Anna

by candyflosslover on Jul 13, 2020
Loving Wives

The next day Jill was at work in her office, a parcel had arrived for her and when she opened it to her delight she saw it was a double ended dildo. She had ordered it some weeks ago so she could use it with her sissy husband. It was longer and thicker than she imagined and she felt heat between her legs at the thought of what she would do with it. She was s...

A Night with Clarissa

by Spango on Sep 28, 2020
Transgender & Crossdressers

A Night with Clarissa Dear Readers, I know some of you came here hoping for more about my budding relationship with Kevin but, if you recall, I had promised Clarissa that I would tell her all about my night with Kevin while she pounded my sissy ass with her massive strap-on Big Bertha. Of course that night turned into most of the weekend but that just m...

Finding Claire

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

*Before... I get cleaned up and instead a drink I have a big mug of coffee and a long, long shower. Thinking on all of it a lot. Then I check my bank accounts twice online. I go outside after slipping into sweats and walk around my house and the yard and the garage, the big barn one out back. It's my second house here actually with Roxanne getting the f...

Sindys Undoing

by SindySuxALot on Sep 26, 2017
Transsexuals & Crossdressers

Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Corn...

Robin and Jimmy Olsen - Sissies Ch. 02

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Chapter 2 Robin prepares, Alfred beware! The evening before the date in Part 1... Sitting in her resplendent suite of rooms in the Manor, Robin inhaled a slow drag from her cigarette. As she exhaled the stream of smoke, she admired her lipstick on the filter of the cigarette. It was funny. More than a year ago, when "he" was just "Dick", he was appalled...

The School Slut Ch. 03

by cherrybubblebutt on Sep 12, 2017
Transsexuals & Crossdressers

Over the next few weeks I was working for George he would continue to give me my 'jabs' and we would pretend that I was an honest maid, well in front of his wife anyway, when we were alone (which was most days) I would insert a butt plug and go around doing my chores until waiting in one of the many rooms George would be waiting naked, maybe with a whip or c...