Sissy Breeding Outdoors Stories

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Another Tasty Creampie

by Skymaker on Sep 13, 2017
Transsexuals & Crossdressers

It was 7:30 in the morning as I stepped off the treadmill. A light sweat shimmered on my fair, smooth skin. I walked into the middle of our gym room and started doing my post-workout stretches. My body ached a bit after my morning run, but it was a good feeling. Every curve felt warm, glowing, supple and sexy. I bent over at the waist to touch my toes. My b...

X.S.X Experiment

by njcaptionlover on Apr 4, 2018
BDSM

All characters are over the age of 18 years old. ***** Hello. My name is Justine, and I'm a 25 year old single male whose fetish curiosity had finally gotten the best of me. My owner granted me permission to recount my story. I started collecting Playboy magazines at an early age. When I had my first computer at the age of 18, the world of porn opened...

Mistress Marisa's Estate Pt. 11

by keptsissy on Sep 12, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... ******************************** The matron sits at the front of the room, gorgeous and tailored perfectly. She's wearing a tight short black dress and nee...

His Breeding Cow

by SWGirl on Sep 12, 2017
Interracial Love

(DISCLAIMER: If you're not a fan of interracial sissy cuckolding, go no further. Don't bother with the righteous indignation or the crude comments. Celebrate why you're here in the first place and move on.) "He said he wants me off the pill, he's going to breed me Tony!" "What!" I said. "Jenna, he can't do that.... You can't do that. You're my wife." I w...

My Life with Little Sparrow

by DomAlphamann on May 11, 2020
Fetish

I almost never come home early unless it's for a good reason. I have two reasons today; one of those being to keep you on your toes, of course, the other one is to give you news. If you followed the rules, as you should always, you might have heard the car pull up, but just in case you were busy doing anything for your own sake and enjoyment and didn't hear...

First time Sissy

by PR Sissy on Sep 29, 2019
Transsexual

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any s...

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A Sissy Maid's Tale Ch. 01

by Erotictales4u on Sep 19, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy in the femdom niche, it is focused on male submissive humiliation and has a Sissy theme running through it. Is set in an imaginary future. ***** The cool air licking at my almost bare ass cheeks enhanced the feeling of nakedness, but I wasn't naked. In fact, it would have been...

Open Your Holes to New Horizons

by basilLEAF on Apr 22, 2025

University of Falika 69 Grand Stellar Lane, Falika, Throbbi Empire April 25, 2024 Dear William Bottoms, We are thrilled to inform you that you have been accepted to the prestigious University of Falika for the Fall term commencing in September 2024! The Admissions Committee was very impressed with your application, particularly your respect of the natural h...

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In the Club

by girlygay on Sep 23, 2019
Transgender & Crossdressers

No longer virginal, now degraded. That is my life as Dave's sissy whore Chandra. With my girlfriend Nikki and her boytoy Adam, we descended into our city's LGBT club scene with a fervor. Dave and Adam were only too happy to share their girls with their friends, and Nikki and I adored the attention, the sex, and the feeling of being desired by so many men. O...

Femberly: Worth the Trip

by hobbnobb77 on Dec 23, 2017
Anal

Sunday morning as I lay awake in a strange bed going over the events of last night. I noticed I had nothing on but smeared lipstick and my choker. I wasn't surprised that the warm body next to me was a handsome young guy completely naked except some of my red lipstick smeared all over his cock and balls, and i started thinking back to my child hood. I now...