Keptsissy Stories

102 results
Orientation
Length
Source
Infinite Scroll

A Sissy and His Master's Hand

by keptsissy on Aug 8, 2018
Fetish

AUTHOR'S NOTE: No character in this story is under the legal age of consent. They are all 21 years of age or older. No sex act in this story takes place other than between two CONSENTING adults. No character in this story does anything against their will or is seriously hurt, permanently physically harmed, abused without prior consent, maimed or killed. Ever...

A Well Groomed Sissy Boy Pt. 02

by keptsissy on Jun 19, 2018
Transsexuals & Crossdressers

I was scared to death. I think I was visibly shaking, at least it felt like it. I was at the door as soon as my doorbell rang dressed as my boyfriend told me to dress—to kill. I had on a micro-mini soft pink flexible tight rubber skirt. It was so short you could see the soft little head of my penis if you looked just below the bottom of it. My butt was lubri...

His Sissy Bitch Ch. 04

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

He treats me just like the woman he's made me into, like the second wife I've become for him. I do all the dirty things his real wife won't do. I dress however he likes, wear what ever turns him on, do things she would never do for him. The only time I wear male clothing is at the office and he never talks to me there other than in a business-like manner. Ou...

A Severe Paddling

by keptsissy on Sep 16, 2017
BDSM

"You know this isn't about you displeasing me, right? I mean I was displeased, very much so. When I saw that your toenails were not painted pink, after I fucking told you to paint them pink, I was displeased, oh yeah. But this is more because I like to do it. I should say I love to do it. But don't think that you didn't disappoint me, little bitch. And you k...

Mistress Marisa's Estate Pt. 23

by keptsissy on Mar 26, 2019
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... ******************************** "I want to thank you for meeting me for lunch. I know you probably would have turned down my invitation had I made it on m...

The Perfect Age Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"Hold still!" Felt his hand come down across my rear so hard I saw stars, wanted to cry out, stifled it as best I could. He slapped me again much harder, loud 'crack' as his large hand came down across my bare butt, made my cheeks quiver. I pulled forward but could not get away. He had the index finger and thumb of his left hand in a vice-like circular gri...

Dominant Wife, Cuckold's Reward

by keptsissy on Sep 25, 2017
Fetish

She's sitting on her worship chair. It's the chair she forbids me to sit in, the one chair in the house for only her. Her or her boyfriend when he visits. He sits where ever he pleases. "Do you want me to touch it, baby?" I look up at her. Kneeling, my hands at my sides, naked on the floor in front of her, I stare up at her. She's beautiful. Wearing a tigh...

Mistress Marisa's Estate Pt. 01

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... ********************************* I am fitted with the tightest of CB-6000 cock harnesses in your closet of harnesses, hurts to sit. Robert has fastened it...

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...

Doggy Style

by keptsissy on Sep 13, 2017
Fetish

I feel his middle finger slide up into my butt. He drives me crazy every time he does that. Each time is like the first time. It's the most erotic thing he does with me. It makes me hotter than when he fucks me, breeds me. I never get used to it. Every time he does this to me it's like the first time. He pushes his finger into me as far as it will go. He fe...