Sissy Fisting Stories

10,571 results
Orientation
Length
Source
Infinite Scroll

Sissy Powers Ch. 14

by ClarasBestFriend on Sep 29, 2020
Sci-Fi & Fantasy

When I woke up the next day, I smiled as I felt Clara's arm resting across my chest, indenting my breasts with a pleasant pressure. It was amazing being a woman; every part of my body felt electric with sensitivity. The slightest touch, which before would have been completely inconsequential, now gave me a staggering amount of stimulation. I wasn't really su...

The Indian Slut Chronicles

by Keannalee on Sep 16, 2017
Loving Wives

Disclaimer: This story chronicles the adventures of an Indian bride who joins a club to fulfill all her fantasies and the later events that follows. I hope you will enjoy reading it and all feedback is welcomed. Happy reading. * 1.Prologue: I was lying quietly on the bed waiting for them to come. The camera was in position. The large mirror reflected my a...

Cornholed

by LaBlancheTraversee on Sep 11, 2017
Fetish

I'm in Tori's basement - tied to a chair, blindfolded, naked and gagged. My hands are cuffed behind me and my rock-hard cock is locked in the plastic cup of a chastity belt, engorged and aching for the feel of her delicate skin. Fantasies of her jacking me off with her hand send a jolt of electricity rushing down to my cock as thoughts of our earlier phone c...

A Sissy Surprise "The House Warming"

by Simply_Sissy on Feb 6, 2018
Transsexuals & Crossdressers

My girlfriend Vicki had been really pushing me to go to her friend Mary's house warming party on Saturday night. Mary had been quite the bitch lately not like the two of us ever really hit it off. To make things even worse she is aware of my panty wearing secret. Vicki had shared this bit of information with her when she first discovered my little fetish abo...

Anthony/Toni

by orvette1 on Sep 16, 2017
Transsexuals & Crossdressers

When I was 15 I was hanging out with some bad guys. We robbed a store, I got caught and went to jail for five years. Anthony, my brother, was only ten when this happened. When I got out of prison my parents told me to not come back to the house. So I moved out of town. Five years after getting out of prison things weren't going well for me. When you are an...

Simon Sissy Slave Ch. 01

by Timewarp10 on Jul 30, 2019
BDSM

It was late summer in 1964, and it was Simon's first day at his new job. Simon had read his letter of appointment several times; and he held it in his hand now, standing anxiously outside the imperiously heavy door, embossed with "Post Room" in faded gold lettering. The door was probably victorian, Simon judged, and perhaps it had been a post room for many d...

Chains Willing Ch. 08

by Radiantlies5 on Jun 1, 2020
Sci-Fi & Fantasy

Chapter Eight: The Red Letter and The Monster in the Mountain. I know... Tales of love take turns for the worst. Bad people bring bad things like shadows and strange omens of apocalyptic events. But, what if? What if the tale was about simply loving girl-cock and tentacles? And so the Red Letter remained unopened. The Monster in the Mountain stayed as...

Start of the Summer Ch. 03

by emelle78 on Sep 18, 2017
Transsexuals & Crossdressers

Part Time Helper Those first two days with the Walkers that I told you about in Part 2 were incredible. When they came home early and caught me wearing Mrs. Walker's lingerie and jerking off on their bed it changed my life. Mrs. Walker dressed me up in frilly, girly clothes, did my makeup, and then I had sex with both of them in every way imaginable. After...

Superstars Rise and Superstars Fall Ch. 01

by felicia_rene on Oct 6, 2020
Transgender & Crossdressers

Superstars rise and superstars fall 1 Part 1 of 4 By Felicia Rene This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy the story Synopsis: The underlying theme is transformation and sexual punishment of the main character for his anti-gay womanizing feelings. For his heinous actions initially making h...

He Calls Me Naomi

by CarrieQ on Sep 13, 2017
Transsexuals & Crossdressers

He calls me Naomi, though it's not my name. Rather, it's a mnemonic that occurred to him when we first met, after he'd realized I'm a high. Neither a man nor a woman; that's what it reminds him of. That's how he thinks of me... It's also his induction method. Because wherever I am and whatever I'm doing, if I happen to hear his voice call that name, I fall...