Sissy Princess Stories

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Orientation
Length
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Infinite Scroll

Fantasy land

by Litle_man on Feb 26, 2021
Transsexual

Our history takes place in the Kingdom of Rubia, where all kind of fantasy races dwell, while the ruling family of this kingdom may compose of humans that may not be the case on the surrounding nations Our story takes place right before the marriage of the crown prince william of Rubia, to the princess of the neighboring dark Elf kingdom of the Hollow tree i...

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Outed and Married Ch. 02

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

The head of his cock pushes hard against the back of my throat. I struggle not to gag. I struggle to control my gag reflex. I feel my throat spread open as he pushes his erection all the way into me, pushes deep into my mouth. It never gets easier no matter how many times he's done this to me. I feel that brief flash of slight pain as he deep-throats me. Fro...

Mistress Marisa's Estate Pt. 27

by keptsissy on Sep 13, 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... ******************************** "Please Mistress, please...so sorry, I had to go so bad, couldn't get you on the phone, couldn't hold it, couldn't, please...

Miss Guided Pt. 04

by MissMarianne on Apr 9, 2019
Transgender & Crossdressers

The next morning I went to Dr. Emily's office for my appointment and reuniting with Charles. When I arrived There were two people talking to the receptionist and I couldn't see her face. Then, I realized that the receptionist was Charles! I heard one of the patients address him as "Charlene." He looked just like a woman. Dressed in a conservative skirt s...

Casey's Submissive Journey Pt. 09

by corduroysissy on Jul 17, 2018
Transsexuals & Crossdressers

A day With Dorothy -- Part One - The Players Casey -- Submissive closet sissyfag with a corduroy fetish, owned by Karen. Karen -- Wife/Mistress to Casey and member of the Lady's Club. Julian - Submissive closet sissyfag owned by Dorothy (Dottie) Dottie -- Wife/Mistress to Julian and member of the Lady's Club. Maxie -- President and founder of the Lady...

It's For Charity

by Tomsparty on Sep 12, 2017
Transsexuals & Crossdressers

You gaze dreamily at the little black dress in the charity shop window. It's Christmas, it's party season and you'd do anything to wear the delicate feminine dress. You shrug your shoulders and gaze further into the shop. The company Christmas party is tomorrow and you've no idea what to wear or who to take. You stare once more at the dress in the window and...

Life's Changes Ch. 02

by eagle166 on Jun 19, 2018
Transsexuals & Crossdressers

If you haven't read chapter one, please read first. Please enjoy and vote. *** Hello my name is Donnie Baker, after reaching our agreement with Kurt, I've put my Daughter to bed in her crib, My sexy blonde wife Lisa is at the end of the hall probably sucking on the biggest cock we've ever seen. How can I be this calm about it? Well really I'm not so calm...

Jock Princess Ch. 02

by Sissyhalo on Sep 15, 2017
Transsexuals & Crossdressers

My brain trembled with my body. I could feel it, my insides all those nooks, crannies, all those muscles inside me trembling inside from being fucked so hard and so deep. All mirroring my brain and the shock of getting fucked too and how much I loved it. And I did love it, more than I should, more than any jock guy ever should. If there was a part of me t...

Lattés and Logic Pt. 01

by LostOnTheRoad on Sep 14, 2017
Transsexuals & Crossdressers

I was feeling pretty good about myself, and I have to say, I looked pretty good too. I had just come from yoga, and as I stood in line at the Bar Italia, I felt I had a glow. The stretching had released all the right endorphins, I was thin and Rubenesque in all the right places, and my ensemble was cute with the right amount of sexy. Now I was going to treat...

Daddies Slut

by XxPrinceAnonomousxX on Nov 26, 2017
Group Sex

I looked around the apartment happily, the candles in the room giving off a nice glow. I knew what I was going to do tonight; I was going to really entertain my longtime boyfriend. Since him and I met three and a half years ago he'd been obsessed with my feminine body, my long red hair, and my girlish figure. I'd never really cross-dressed much before I met...