Strapon Sissy Stories

8,068 results
Orientation
Length
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Infinite Scroll

A Night at Home with Mistress

by Georgie27 on Sep 19, 2017
BDSM

Saturday evening found me in my usual position. I was handcuffed to the radiator in our bedroom, on my hands and knees. My upper body was tightly laced into my red corset, my false boobs filling the bodice. My freshly shaved legs were encased in fishnet stockings. Black spike heeled boots came up to my knees. i was wearing a blonde wig and tarty make-up, inc...

The New Neighbors (Black Femdom)

by Dunn81 on Aug 12, 2019
BDSM

Hi my name is Julia i'm 42 years old and i'm with my daughter Sofia who's 20. I'm a pretty fit girl who are vegan. I Lost my husband 5 years ago and since that i never dated anyone. I'm a 5'2 brunette with medium size boobs and a medium sized ass too. I weighted around 130 pounds. My Daughter is 5'5 big boobs and small ass. She trained at the gym a lot since...

Turned into a Slut Ch. 04

by xaitonnar22 on Sep 19, 2017
BDSM

After grabbing some quick sandwiches, Jennifer and I returned to her home. We found a note on the kitchen table from her parents letting us know that they would once again be out of the house for dinner. They didn't expect to be back until ten o'clock, it was seven right now. Once in her room, Jennifer commanded me to strip out of my jeans and bend over the...

How I went from Domme to Slut Ch. 03

by Ms_Allison on Mar 7, 2018
BDSM

Another night of not knowing and torment was coming, this time I would have company, amber would be with me. This would be new. Ms. Linda had contacted me during the day via text. Her instructions were quite simple, amber and I were to bring a selection of slutty lingerie for her to choose from, our highest heels, and not bring any attention to ourselves as...

Sindys Undoing

by SindySuxALot on Sep 26, 2017
Transsexuals & Crossdressers

Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Corn...

A Letter to Our Pantyhose-Sissy

by Sheermistress on Sep 19, 2017
Transsexuals & Crossdressers

I'm on my bed on my knees, my skirt pulled tight and just a little high, exposing my control-top pantyhose to your eager eye. My feet are dangling over the edge of the bed and you, my little pantyhose-slut, are standing behind me, dressed in your sexy schoolie outfit and mary-janes. Your face is made up in a prissy, sissy, teen-girl way and your hair is fini...

Finally a Real Sissy

by Parasissy on May 7, 2019
Transgender & Crossdressers

I have to tell you about the experience I had with my wife the other night. But first a little background for context. I have been married to my wife for over 10 years, I told her a little about my "adventurous" side before we got married, and I've slowly revealed more as time has passed. She tries to accommodate my Sissy desires, but truthfully she is not...

Total Drama Island

by Yelawolf on Oct 12, 2019
Fan Fiction

(Every character in this story is 18+) You step off the boat last. You see all of your competition. Most of the chicks looked pretty damn hot. Especially the cool goth chick. The guys mostly seem like idiots besides a tough-looking dude with green hair and piercings. You walk on the dock seeing the poor condition of the island for the first time. You didn't...

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Haitian Dominatrix with a Strapon

by Samuelx on Sep 1, 2017
Group Sex

Black men the world over got this nasty habit of walking around like they own the place. Act like they're the toughest guys. Swagger like they've got the biggest dicks. And I both love and hate them for it. My name is Jeannette Saint-Mathieu. I was born and raised in the town of Cap-Haitien, in the North side of the Republic of Haiti. I've been living in the...

Sissified by My Sister

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

I will never forget that night. The night I discovered how I truly am. My true self. Its an unforgivable night. And I never thought my little sister would be the one to help uncover this part of me. I was a young, average 19 year old, my sister and I were home from college for winter break. I had short, blond hair and my sister had brown hair cut about at h...