Keptsissy Stories

102 results
Orientation
Length
Source
Infinite Scroll

A Wife's Lover, His Boss

by keptsissy on Sep 13, 2017
Fetish

I didn't act like it at the time but I was shocked by what had happened. I didn't let my husband know it but I was scared. I felt like a little girl. I smile to myself when I think back about that now. I acted brave, vixen like, but I was scared. I was putting up a good front and didn't know if I could go through with any of it. I learned that not only could...

The Perfect Age Ch. 04

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

When I saw the light go on in his garage I felt faint. I had been daydreaming about him, his taste in my mouth, thinking about what it felt like to suck him. Every time I thought about pumping him with my mouth my little thing would get hard. He hadn't fucked me yet, not like I now wanted him to. He'd run his cock up between my cheeks and cum all over my che...

The Man That Owns Me Ch. 02

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

I feel a sharp slap on my left cheek. His strong hand comes down so hard across my butt it shakes the bed, it makes me cry out. A loud 'SMACK' reverberates off of the walls in my bedroom. "Please..." I hear my voice quiver, tremble as I look back over my shoulder at him. It's the fifth time he has hit my rear end hard letting each slap sink in before the...

A Very Special Marriage

by keptsissy on Sep 25, 2017
Fetish

"I wouldn't blame you if you left me but it would break my heart if you did." She's sitting at the dining room table. She just came home from being with her lover. She's been gone over night. There is a large stain on her blouse. I know it's his cum. "He fucked me twice and then he had a friend of his fuck me while he watched. I kept thinking about you the...

His Sissy Bitch Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"You've come a long way, baby." He smiles at me, watches me as I cross my legs. I'm sitting across from him. I can tell the effect I have on him, every time he visits, sees me dressed fem for him, he's hard, rock hard when I meet him at the door. And I know what outfits turn him on the most. I know he fantasizes about me when he's fucking his wife. She doesn...

His Sissy Bitch Ch. 02

by keptsissy on Sep 18, 2017
Transsexuals & Crossdressers

The next day at work I felt my face flush every time I saw him, felt embarrassed and felt like stammering every time I spoke with anyone in the office. His office is across from mine, he's my boss and I have to see him daily. It felt like everyone in the office knew! I was so nervous I didn't speak to anyone, avoided everyone as best I could. He didn't say a...

The Man That Owns Me Ch. 04

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"Don't be shy. Pull your panties down, baby boy. Show the man that cute little thing." He laughs, smiles at me. He's seated on the couch next to a man I've never seen before. When they entered my house I expected only him. I hurry to do as told. It's something that is part of me now. I never hesitate to do as he orders, dominant of otherwise. He owns me com...

A Devoted Husband

by keptsissy on Sep 18, 2017
Loving Wives

PART ONE: I never question her, ever. I hate having to clean her after she's been with him but I never talk back when she tells me to do it. I usually do it at the door as she returns home from a date. I do the best I can to imagine what it's like to be allowed to go down on her without his presence, without his cum all over her. I'd never tell her that; ne...

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...

A Well Groomed Sissy Boy

by keptsissy on May 15, 2018
Transsexuals & Crossdressers

"If I receive any complaints I'll diaper you and put you in your dog cage for 48 yours, no exceptions. Do you understand?" He looks down at me. I feel his dominance over me. I see the look on his face. I start to cry hard. "Please, Daddy, no. Don't do that to me, please...I'll be good...please..." I stammer through sincere tears. "Well then, all you have...