Sissy Father Stories

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Orientation
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Elaine's Neighbors

by Hotenuf4u on Sep 14, 2017
Fetish

Elaine's Neighbors: Their Story Tammy's mother had divorced her father just over a year ago. It seems that his lack of trust got the best of him which ultimately led to his downfall. Tammy was home on a vacation from her college studies when she noticed a change around the house. It seems that now her father has turned into a workaholic which left Mom prett...

Cam Slut Pt. 01

by GavinIsaNuisance on Oct 26, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and entirely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Eighteen year old Jeremy Briarstein is forced to remain home while his parents go on an extended twenty year anniversary vacation. He is further dismayed to dis...

Sabbatical or Continuous Gang Bang?

by TonyaTV69 on Sep 12, 2017
Transsexuals & Crossdressers

My twin sister Laura had already left to go back to college this fall season, but I had decided to take off a semester as I was totally burnt out on school and needed a break. We were twins but not identical though we did look a lot alike and roughly the same size me being a few inches taller. My parents were fine with fine me taking a short break but adam...

A Sissy in the 22nd Century

by JerkGently on Jul 1, 2020
Transsexual

In a future not too far flung, humanity has progressed to a stage where almost all production and provision of society’s needs is automated. With no need to work, all citizens are instead driven to find lifestyles that fulfil their own and each other’s fundamental desires. This is achieved by the medium of an overruling system of artificial intelligences and...

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The New Swim Team Pt. 06-07

by Doubleganger on Sep 19, 2017
Exhibitionist & Voyeur

Disclaimer: I began writing this seven part saga in late 2015. As the old saying goes; all good things come to an end. Here are parts 6 and 7. I hope you enjoy reading them, as I did writing this chronicle. All are over 18 years of age. This story is completely fictional. None of the characters portrayed are real, also none of these sexual encounters ever...

Sissy Jessica Kinky Office Shagging

by Sissy Adele Howells on Aug 18, 2017
Fetish

Hi to all you kinky readers out there. I have been transported into a fantasy world, which resembles the office, in which I work. The women, that I fantasise about every working day, are about to reek humiliation on me for my past behaviour. Tied to a chair naked in a small box room, is not a comfortable way of spending your time over the early part of a col...

Daddies New Girlfriend

by LilLindaMelons on Sep 19, 2017
Transsexuals & Crossdressers

Part 1 Doug suspected his 19 year-old son Jerry was stealing money. Doug worked far too much trying to provide for his son to supervise him properly but drew the line at theft. So he decided to set up a web-cam behind the mirror in his bedroom, he'd used the very same 2 way mirror to film his dead wife Cynthia on more than one occasion. Jerry had been dress...

The Wedding Ch. 04

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 4 -- Teaching, Teasing and Testimonials... I was a little stunned and leery after reading my version of this contract which wasn't all that different from Patti's... From changing my name to rescinding my rights to wear male clothing while in the employment of Darren and Carol -- or Ma'am and Sir, and also, not to f...

Cheap Sissy Whore To Call Girl Ch. 03

by HardSoft on Sep 15, 2017
Transsexuals & Crossdressers

My first few days at the hospital wasn't the typical hospital stay. I'd get fucked by everyone who worked there. Most of the time I was too dazed to realize what was happening but there was always a cock or a pussy that needed attention. The doctors would come in during their breaks to ass fuck me. The nurses would make me lick their pussies clean. I didn't...

The Perfect Age Ch. 02

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

I started seeing him regularly. He became my first real boyfriend, more like my Daddy. And I liked that too. Have had a select few men as erotic as he was since then, he was the first. And he was the one that showed me what I really was, showed me the real me. I'd think about him all the time. I'd masturbate daily thinking of what my 'next time' with him wou...