Sissy Slut Stories

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Sister, Meet My Sissy

by satinmarabana on Sep 16, 2017
Transsexuals & Crossdressers

George was mincing around the bedroom on his new high heels, almost moaning in joy as his big cock slid around in the inside of his panties. I could see the thick buttplug in his ass through the thin panty material and I smiled. George was a lovely sissy with almost feminine body type and features but with that delicious big cock. He'd taught me as much abou...

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...

Black Lady Cuckolding Black Men

by Samuelx on Sep 17, 2017
BDSM

What's up dear family? My name is Yasmina Hussein and I'm a Somali Canadian woman living in the City of Ottawa, Ontario. A while ago I discovered the world of BDSM, shortly after my divorce, and have been really into it ever since. I discovered that I have a talent for and a desire to dominate people, especially men of color. As a Somali Canadian woman, I wa...

Panty Jerkoff Encouragement

by dirtywordygirl on Sep 13, 2017
Exhibitionist & Voyeur

Right now, I just want you to lay back on the bed and show me what you have down there... No! I DIDN'T SAY YOU COULD TOUCH IT! That's very naughty of you to do that. First you have to ask me, so let go of your cock and show it to me like a bad little girl...you're a very bad little girl, aren't you? Let's get you a little wet and slippery, ok? Ask me if y...

Sissy Pantyhose Twins Ch. 01

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

Twice The Fun... Part One... My Slut had received her orders in the envelope which was always left on the kitchen counter before I left for work. She was to perform whatever was mentioned in this envelope, each day, without question -- either during the day if so asked, or to be ready for me when I get home. Whether it was a new outfit, a specific outfit,...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Caught in Panties & Dominated Ch. 05

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Cast Trace - me Tracy - me, dressed en Femme Rick - head of security at work, had just caught me masturbating at work, dressed as a woman Ken - my roommate Ok, ok, I hadn't mentioned this before, but my roommate Ken is gay. He would flirt with me from time to time, even hit on me, and I pretended to discourage him, but sometimes, late at night in my roo...

Sissy Slave Fantasy

by tinkerslut on Sep 13, 2017
Transsexuals & Crossdressers

A fantasy written to my mistress.. Sissy kneels before you, her eyes down, waiting on your pleasure. Sissy is wearing frilly panties with a matching bra, thigh high black lace stockings encase my legs. The red dress barely covers her smooth bottom. The high heel shoes, locked on my ankles, crossed behind me. I can't speak because of the ball gag in my mouth...

The Awakening of a Sissy Pt. 06

by sissyjolie4u on Mar 2, 2020
Transgender & Crossdressers

While still admiring myself in the mirror, I received a text from Mistress, that read: I am so happy to hear that you are embracing and accepting that you are and were always meant to be sissy Jolie. Let me assure you, I will assist you and help you blossom into the ultimate sissy that you are meant to be. In time Joe will be completely stripped away. You ha...

High School Fuck Slut

by TonyaTV69 on Sep 25, 2017
Transsexuals & Crossdressers

I grew up out in the country as a boy with my mother and 2 sisters. My dad was never around since he was always off working or as we found out some years later running around cheating. If we saw him at all it was on the weekends for a quick family outing to the mountains or park. Once in a while mom and dad would get all dressed up and go out to dinner. This...