Sissy Fisting Stories

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Proud Beta

by Sissyhalo on Mar 13, 2018
Transsexuals & Crossdressers

All parties are over 18 years of age. *** I'm a beta. And yeah for those that get what that is, we're real. I was a white kid that was on the skinny side and I was born and grew up with a little dick. And I was everything that came with being a small dicked little loser then. Bad at sports because that meant dressing rooms back in high school and never...

Webcam Mistakes

by chrissycockslut on Apr 3, 2019
Transgender & Crossdressers

I guess I should've been more careful. But what can I say? I was a young man and I was stupid. I had just passed my 18th birthday a month earlier and I had treated myself to my very first, brand new dildo. Nothing crazy, only 5 or 6 inches long and just 1.5 inches girth with a suction cup base, but it was perfect for a beginner. Luckily, I had plenty of ti...

Getting Some Helping Hands Inside

by Cumfusion on Sep 14, 2017
Anal

[This is a sequel to 'Cream Buns after the Party'] It had been scary towards the end of the party as I knew, if any of the hotel staff had walked in, I would have been instantly dismissed in disgrace. That's kind of not what you need in your first job after college. I had been asked to be bar tender in one of the hotel function rooms. I didn't know it wa...

AliExpress and Sissy Downfall Pt. 03

by His_fag_wife on Nov 2, 2017
Transsexuals & Crossdressers

Tim cupped Emma's arse cheek as they went into the hotel room, stroking her, sliding into the cleft of her cheeks, warming her up a little more, not that she needed it. Charlie didn't notice them come in at all. Not that she could really turn her head with the thick COCKWHORE collar padlocked tightly around her neck. The cords attached to the dildo were als...

Black Woman Owns White Slaves

by Samuelx on Sep 13, 2017
BDSM

My name is Nicole Swanson. I'm a five-foot-ten, short-haired and golden-eyed, dark-skinned and voluptuous young Black woman living in the city of Brockton, Massachusetts. The City of Champions. At least, that's what the locals call it. I call it Shit Hole, USA. I'm a woman who turned her sheer contempt for human beings into an asset. You see, I am a Professi...

Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

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Sissy Powers Ch. 13

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

"You know, once you take my ass, there won't be a single one of my holes that another man could use..." Heather moaned, overcome with arousal at the thought of belonging to me so totally. "Uh, what about your mouth, babe?" Clara teased from slightly to the side, rolling her eyes at the overly horny girl forgetting one of her own fuck-holes. "Nuh-uh, becaus...

The Bimbo Dildo

by Sissyhalo1 on Dec 24, 2019
Transgender & Crossdressers

It came to me through a yard sale at this house full of super hot chicks in town living together selling all their ex-boys stuff. It was a smooth ivory dildo a full foot long and super realistic and thick too. It made my pussy twitch just looking at it. All of them, all of them were super hot but too hot that porn guys wet dream with round perfect asses,...

On a Scale of 1 to 10

by His_fag_wife on Apr 17, 2019
Transgender & Crossdressers

He couldn't help himself, it was a new office environment for him and she truly was stunning. Even her little sister Claudia was delightful and sexy, but in a more understated way. The fact that she worked for Georgia her sister, set the hierarchy, but even more so, Georgia towered over her younger sister, and then there was Georgia's innate sense of style a...

Anna from Amsterdam

by OpenMouth on Sep 14, 2017
Erotic Couplings

She was a nicely-built brunette, early 20s, glasses, eye makeup; she was wearing pushup bra, tartan micro skirt and heels and smoking a cigarette every time I passed. I looked at her for three days; she started to wave after a while, then she opened the door and I told her I was just looking. She replied "yeah, for three days..." I was with a work colleagu...