Keptsissy Stories

102 results
Orientation
Length
Source
Infinite Scroll

Outed and Married Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

When I entered the room with their drinks on the tray I was carrying I thought I would be pleasing to my husband. I made sure that my skirt was properly adjusted the way he likes me to wear skirts in the house. He insists that my rear not be covered below my tight little hole, insists that he have instant access to it if he wants to use it for his pleasure....

A New Lover

by keptsissy on Sep 14, 2017
Fetish

"I know it's hard for you sometimes, believe me. I know. This would be hard for anyone. But you have to remember that this was your idea and it's a fantasy that you had me turn into a reality. And I like this reality very much, baby. Not to mention it makes that little dick of your hard almost constantly." She sits, stares at me. She moves to the edge of he...

Mother Dear Pt. 01

by keptsissy on Sep 13, 2017
Fetish

"Let's say for instance that I had son that was a sissy boy. A son that not only was a sissy boy that did very dirty and naughty things while he still lived in my house, dirty things for our next door neighbor, but a naughty little boy that liked to dress up in his mother's underpants too. I think a boy like that would need guidance. Don't you? I remember wh...

Mother Dear Pt. 10

by keptsissy on Sep 14, 2017
Fetish

"Ooooo, I love doing this for my little boy, so pretty. You really are. And the way that little thing of yours shines when it's all slippery like this and the way it throbs is precious, sweetie." She watches my body heave and shudder as her hand moves over my erect penis. I'm seated on my 'reward' stool. It is a four-legged 3' tall wooden stool mounted so t...

The Man That Owns Me Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"Pull that sissy thing down between your balls! I don't care if it hurts. You'll get used to it. The whole point is to have it tucked between your balls, your little baby balls up on the side of it and sticking out in front! The sissy bitch I saw do it on the web did it, so can you." He brings the riding crop down across my butt, hard. I cry out as I strugg...

Mistress Marisa's Estate Pt. 30

by keptsissy on Sep 14, 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... ******************************** "Mary, I'd like you to stay an extra day or two, maybe even for the rest of the week. I have plenty of room. Is that somet...

Mother Dear Pt. 11

by keptsissy on Sep 14, 2017
Fetish

"Mother, please...please...ahhh..." I'm in pain. It shows in my whimpering, pleading voice. She sips her wine, smiles as she watches me walk, mince, strut around the room. I am walking as she told me too, one foot in front of the other, super-model-on-a-catwalk-like prance. She has 'worked' with me almost every night for the past three weeks, 'training' me...

Mother Dear Pt. 08

by keptsissy on Sep 12, 2017
Fetish

She pushes back hard against me, wiggles to get it all the way into her. I feel her weight as she sits back onto me. I feel her cheeks spread and engulf my face completely. She holds her butt in place and starts to grind. I feel her wetness all over my chin, feel the tight little hole of her rear end push against my nose as she sits back on my face. "Oooooo...

Mother Dear Pt. 12

by keptsissy on Sep 14, 2017
Fetish

My white frilly lace panties delicately pulled down passed my stocking tops, so as to not crimp the lace, dangle from my ankles. The twelve inch small chain that holds my ankles and the thin steel cuffs locked to it rests on the carpeted floor, the panties rest on top of it and cover the tops of my 3" spike heel pumps. My small but erect penis exposed in fro...

A Sissy's Reward

by keptsissy on Sep 19, 2017
Transsexuals & Crossdressers

Every time he does this to me he drives me crazy, keeps me addicted to his hand. I feel my sissy-like penis strain to escape from between my legs. I'm very small, only about 3" when hard. I keep it tucked for him, hold it tight between my legs at all times...except for when he does what he's about to do to me now. He's not interested in my tiny thing. Only...