Sissy Fisting Stories

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Orientation
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Infinite Scroll

Jack and Jill Pt. 01: Jean

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

Dinner was almost ready when the doorbell rang. He turned down the stove and went to answer the door. She was taller than he expected, broader too, but she was undeniably a very attractive black woman. 'Hi,' she smiled 'You must be Jack, I'm Jean, it's nice to finally meet you.' Jean was Jill's colleague from work, he had heard about her many times over t...

AliExpress and Sissy Downfall Pt. 09

by His_fag_wife on Aug 20, 2018
Transsexuals & Crossdressers

Charlie stood wobbling slightly, on the 5 inch heels. Legs a little apart to accommodate the very substantial base of the Fenrir Dragon cock currently stretching her wide open, holding her buttocks apart and her asspussy wide open with the 2 1/2 inch diameter. She felt better now, shattered and tired but she was basking in the looks of approval from both her...

Location, Location, Location... Pt. 02

by DoxyTrainer on Dec 9, 2019
Anal

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** "We can't keep drugging Gabe! (can we?)" That night I couldn't help but stare blankly at the ceiling of my room. The things I had done. The things that had been done to me. What hungered within me. Just turning over in bed, my well-fucked, recently reorganized insides stre...

Mom's Big Black Hobby Ch. 06

by MiddleKoala on Jul 13, 2020
Transgender & Crossdressers

This story has with incestuous and homoerotic themes as well as non-consensual sex. If you are offended by such, do not read. This level of depravity is not to be taken lightly and the deeper down the rabbit hole you go the more you will find that may offend you. You have been warned! All characters in this story are over the age of 18. The entire story is...

Slave Ch. 01

by slaveheathen on Sep 25, 2017
Fetish

My name is slave. Of course, that's not my real name, but for the story I plan to tell, it will do. For the record, I'm a bisexual submissive male. There are few who know this fact. Common enough story there, I suppose. Truth is, my family and friends could never accept my lifestyle, so that part of myself stays safely locked away. But behind closed doors....

Tee and Gino

by gin0aki56 on Sep 16, 2017
Transsexuals & Crossdressers

Tee: You knock on my door, and I let you in my place. I am dressed in lingerie -- stockings, garter, and a lace thong -- and wearing heels. You smile when you see me, which makes me feel sexy. Once inside my house, I lead you to the bed. You sit on the bed and pull me to you. You grab my exposed smooth butt cheek and squeeze it, while you pull me close and...

Fifi La Femme: A Pansy at Last Ch. 02

by pris69696 on Sep 14, 2017
Transsexuals & Crossdressers

Chapter 2- Missing Big Frank Coming Out Telling our wives wasn't easy especially for me who had seduced Shirley's gorgeous hetero husband by dressing up in my wife Doreen's lingerie and make-up and offering him full homo sex as a limp wristed effeminate lady-man. It was my first experience as a queer and when Frank asked me to marry him; to be his gay wi...

To the Manor Bound Ch. 03

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

[So I finally got around to finishing chapter three, apologies for the delay. As with the other two chapters this includes forced feminisation, BDSM, and non-con, so it might not be your cup of tea. Regardless do comment and email me to let me know what you think, or just to say hello!] ***** Chapter 3 -- Three Weeks after Transformation "Now it is ver...

A Mistress to Obey

by gbr2004 on Sep 12, 2017
BDSM

This story involves bdsm action, forced bi, pain and humiliation. Not your thing? Please pass on by. * I met her online. She was older like myself and was looking for a submissive man. We exchanged a few emails but she really wouldn't say much about what she was looking for and expecting from her sub. In her profile she said she was into such things as bo...

Slave Ch. 02

by slaveheathen on Sep 25, 2017
Fetish

Chapter the Second Just a note: This story contains bisexual sex, fisting, bondage, piss play and more. That's why it's in the fetish section. If this isn't your cup of tea, don't read it. If it is, enjoy! Now, on with the depravity... As I knelt there on the piss soaked blanket in my piss soaked clothes, I tried to gather my wits, not to mention catch my...