Keptsissy Stories

102 results
Orientation
Length
Source
Infinite Scroll

Little Sex Toy Ch. 06

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

Squatting on my heels, feet just up under the curve of my cheeks, I can feel the ruffles on my sissy sox up against my bare legs. They would tickle if I weren't so afraid and focused on doing what he demands I do in front of these men. My knees pushed up toward him and spread wide, don't dare hold them together, don't want to get slapped, I feel his hand o...

His Sissy Bitch Ch. 06

by keptsissy on Sep 18, 2017
Transsexuals & Crossdressers

I think about it all the way home, makes me so hot I want to masturbate right there in the back seat of the cab. I can feel the wet spot on the end of my little thing, feel it against my inner thighs, feel my small baby like penis slide around tucked up under my butt, pushed down and held between my legs as we ride toward my house. I try to keep my penis tuc...

A Wife's Lover, His Boss Ch. 02

by keptsissy on Aug 30, 2017
Fetish

"I take it she's spoken with you about me, about me and her?" He sits behind his desk and stares at me. He's aloof. He's never said more than two words to me before, passing in the hall at best. I'm so nervous I can hardly speak. When we got invited to his all-company BBQ party at his house it was the first time he'd ever really paid any attention to me. Mo...

Mother Dear Pt. 09

by keptsissy on Sep 13, 2017
Fetish

"I love this place, baby boy. Every time we dine here I think back to that one fateful dinner, the dinner where this all began. The dinner after I came to your home unannounced innocently enough, wanting to take you out to eat only to find you dressed like a girl and on your knees doing what we bad girls do, delightful." She winks at me over her wine glas...

His Sissy Bitch Ch. 07

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

He makes sure they all get a good look at my rear end. He pinned my skirt up in the back, large safety pin holds my skirt up at the top. It's a large baby diaper safety pin, one that women used in the 1950s, pink plastic shows at the top. Kind of cute, the pink plastic matches my ear rings. I could just take my skirt off but he says it's way sexier this way,...

The Perfect Age Ch. 05

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"Look at you. You're beautiful, honey." She sits on the couch and stares at me, a big smile on her face. "You're the daughter I never had." She laughs, looks adoringly at me. I'm wearing a short soft tight-knit pink off-shoulder dress. White short stack heel summer shoes with ankle straps that show off my pink toenails. And under it all white satin pantie...

A Husband Further Learns His Place

by keptsissy on Sep 18, 2017
Fetish

PART FOUR: The first time they were together was at our company bbq at my boss's house. We were at a huge party, tons of people there. Many were his clients. When my boss met my wife for the first time I could tell he liked her, openly complimented her on the shorts she was wearing. They were short to say the least and tight. She always dresses much sexier...

The Perfect Age Ch. 01

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

I'd just turned 18 and it was high school graduation. Most of my graduating class was at the raging pool party at my best friend's house. I lived next door to him and his parent's house was the place to be that day and most hot summer days. I didn't think much about the fact that his dad kept talking to me about 'the future' or that he seemed to be around wh...

Dominant Wife Entertains Her Lover

by keptsissy on Aug 30, 2017
Fetish

"Who does this belong to? Who owns this, little girl?" He rubs her pussy in his hand. She's soaking wet, dripping. Her breathing is deep, a slight sigh with each breath. She moans softly with her eyes closed. She opens them and sees him inches from her pretty face. "You. You do, baby, you...uhhhh, don't stop, baby...uhhhhh..." She is cut off as his lips g...

A Dominant Wife Takes Another Slave

by keptsissy on Sep 16, 2017
Fetish

"You love your wife, don't you, baby?" She reaches down and runs my erect penis through her hand. I whimper, shudder at her touch. She smiles down at me as she sees me quiver. Her hand covers the entire length of my erection and then some, something she teases me about. The CB-6000 penis harness I wear at all times, except for reward or punishment sessions...