Keptsissy Stories

102 results
Orientation
Length
Source
Infinite Scroll

A Photo Session, My First

by keptsissy on Sep 18, 2017
Transsexuals & Crossdressers

When he called and said "We're going to something special today, sissy boy." I got instantly wet in my panties. He arrived at my house and stripped out of his clothing almost before I had a chance to close the door. I feel his large hand cup my penis and balls. He covers them completely and easily. I'm small, less than 3" erect, baby-like. I feel my little...

Cuckold Sissy Husband Goes Further

by keptsissy on Sep 18, 2017
Loving Wives

PART EIGHT: "Baby, I've been thinking about you. Been thinking you need something more to look forward to. I think that you would enjoy cumming more, enjoy your little thing played with more if it was more a special occasion." She's seated at the kitchen table. She has a small package on the table. "Come here." She watches as I walk to her. "Mistress, I n...

Devoted Husband Learns a Lesson

by keptsissy on Sep 18, 2017
Loving Wives

PART ELEVEN: I was her houseboy-slave almost two years prior to her taking a lover. She took over my submissive fantasy, made it completely hers. At first it was talking dirty when I'd service her. She started 'expanding' on that, got very cruel, teasing and dominant. She started checking out dominatrix websites too. After about six months she was a complet...

Mother Dear Pt. 14

by keptsissy on Jul 11, 2018
Fetish

"Hold that skirt up like a lady! Show a little dainty elegance. And push that hip out like I taught you to do. Sometimes I think you don't listen when I talk to you!" She is kneeling in front of me adjusting the lace on the top of my panties. They are down around my ankles displayed over the tops of my 3" spike heel thin little ankle strap shoes. She adjust...

The Man That Owns Me Ch. 01

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

Unlike many of the other men I saw, let visit me and have their way with me, he was not to the cum-and-run type. Most men are. He was different than all the rest. Most of the men I met online and allowed to visit me at my house were all hot and bothered in the chat rooms, hot to be with a sissy boy that was all femmed up and girly girl. But as soon as they w...

A Sissy Girl Bitch, 'BEST IN SHOW'

by keptsissy on Mar 3, 2020
Fetish

** Author's note: All characters depicted in this story are fictional, well beyond age-of-consent, and are consenting adults. ********************************* He made a point of showing me off, displaying me. That was obviously his thing from the start. Many men at the clubs he'd take me to were allowed to not only look but touch me too. I never thought a...

The Perfect Age Ch. 07

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

It wasn't long after I became his lover that he had me seeing other men. The first time was at a party he took me to several months after I started seeing him. He had me go down on a friend of his while he watched. Assured me all was okay, it would be 'safe'. 'Just do it, you'll do that for me, baby, right?'...I did. I actually enjoyed it. I found out early...

The Perfect Age Ch. 06

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

He's up over the top of me, slighty off to my side with his left nipple in my mouth. He has his hand on my penis and strokes me softly as I suck, nibble and kiss him. I can still taste his cum in my mouth. I can taste my rear end too, it was all over his cock when he came in my mouth. After he fucked me for over an hour he finished in my mouth. It's the fi...

Mistress Marisa's Estate Pt. 11

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... ******************************** The matron sits at the front of the room, gorgeous and tailored perfectly. She's wearing a tight short black dress and nee...

Mistress Marisa's Estate Pt. 05

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... *************************** "Hurry up, just the things you need for the weekend, that sissy shit you do to look like a girl. Let's go." He's staring at m...