Sissy Friend Stories

145,580 results
Orientation
Length
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Infinite Scroll

Slave History

by timeagain93 on Sep 17, 2017
BDSM

These are my recollections of my slave history. Four Goddesses have dominated me. I'm writing this to let my current Mistress understand my story. Mistress D read "Variations" magazine and spanked me with a wooden spoon. She tied me naked to a chair and blindfolded me. She made me sit there in silence. I was wearing her panties while talking on the phone w...

Mindy's Moving Day - CFNM Ch. 01

by BuckyDuckman on Sep 25, 2017
Fetish

Author's Note: Humiliation, CFNM and pegging lie ahead! I've had this idea for a while about an adventurous married couple on the edge of opening a new chapter in their married life. I hope you enjoy reading it as much I enjoyed writing it! On her first day in town, Debbie and I were Mindy's only friends. The professional moving company hired by Mindy's...

Chuck

by wajawhiii on Jun 5, 2018
Erotic Couplings

My name is Marjerie. I'm thirty-nine years old. I was married to George when I was only twenty. He left when I was just twenty-three and Charles was only two. I got an uncontested divorce three years after he disappeared. Charles is the only thing George gave me and the best thing I've ever received. Charles is now eighteen and just graduated from high scho...

A Friend Catches Me Ch. 03

by PinkPanties4me on Dec 2, 2019
Transgender & Crossdressers

Sorry it took so long to continue my story...For those of you just finding this, please read my first two sections, A friend catches me 1 and 2. *** Karen looked at me and said," I have had an idea for a while, so now is as good a time as any!" She took out her cellphone and made a call. "Hello Roberto, no I don't need to make an appointment to get my hai...

Steve to Stevie to ?? Ch. 07

by gbr2004 on Sep 13, 2017
Fetish

I had returned to work after my first nite with Ms Storm. The night she turned me from a young man to her slave. Ms Storm had came to my work place and had talked to my boss for a long time but I don't know what she told her but my boss, Ms Hunter, had talked to me like never before. Then I had been ordered to return to Ms Storm's house that night. Upon arri...

Momdom a sissy son's wish

by Viking973 on Jun 20, 2020
Transsexual

Intro: You never had much luck with the girls in high school. You had a few girlfriends early in high school but the last 2 years before college was rough. It had come and gone, you enjoyed it, you weren't an outsider and had many friend groups but you never went out to parties or out of school to meet up with friends. You enjoyed video games and porn too mu...

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Mistress Joan Ch. 01: Punishment

by slutty_sissy_nikki on Mar 10, 2020
BDSM

BASED ON A TRUE STORY! All characters are over the age of 18. This is my first short story and I welcome constructive feedback. PRELUDE The cane cut through the air to deliver another mark onto my plump bum. I tried, unsuccessfully, not to flinch when I heard the wish sound of the cane travel through the air. Knowing it was coming was the worst part, or ra...

Robin and Jimmy Olsen - Sissies Ch. 04

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

The Date Continues (finally) ***** Just as Ollie and John began to wonder what was keeping their dates, they spotted the delectable pair of sissies returning from the rest room. When they reached the table, both men stood. Their politeness was rewarded by a brief kisses from the pretty lads. Each girlyboy also managed to run her hands across the crotch of...

Caught!

by centrum1000 on Sep 18, 2017
Transsexuals & Crossdressers

It all happened so quickly that I can barely remember the details. It was a Saturday afternoon and I was doing my laundry in the dorm laundry room when she came in. I've seen her around campus before and regularly pictured her naked body pressed against mine while I pleasured myself. Her name is Carrie. She is almost as tall as I am at about 5'7" with bleach...

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...