Sissyboy Stories

140 results
Orientation
Length
Source
Infinite Scroll

Jennifer Monroe & the Ladies Ch. 02

by corduroysissy on Jan 14, 2018
Transsexuals & Crossdressers

Everyone stopped. The ladies all looked at Jennifer with their mouths hanging open, and Debbie just stood there mortified, not believing what he just heard. "Do you not speak English bitch, I said get the fuck out of here right now. That's your punishment." He didn't move. "Oh, are you feeling sorry now Tinkerbell, well tough shit, beat it, bye-bye." De...

Casey's Submissive Journey Pt. 08

by corduroysissy on Mar 6, 2018
Transsexuals & Crossdressers

Mistress Betty - Part Two When Karen returned from the kitchen she was holding a drink in each hand and the sight awaiting her not only shocked her, but stopped her dead in her tracks. Betty had her skirt pulled up on her belly and Debbie was between her legs licking her pussy. Betty's face was upturned, her eyes were closed and she had a very contented smi...

Casey's Submissive Journey Pt. 04

by corduroysissy on Dec 31, 2017
Transsexuals & Crossdressers

Angie & Debbie (Fag Night) Part Two After putting on the movie Angie walked to the side of the bed and carefully removed her hat, gloves and shoes. As she did she called Debbie over and told him to lie down and get comfy. He took a sip of his drink, put it on the nightstand, then laid down on his side and watched the video. Soon after he felt Angie's w...

Madam Molly Pt. 01

by corduroysissy on Feb 6, 2018
Transsexuals & Crossdressers

It all started in a chat-room, "Closet Sissyboys." Jesse had been spending a lot of time in chat-rooms in the six months following his divorce. He wasn't looking for love, he just liked to drink and have cybersex while jerking off with corduroy. Yes corduroy. Jesse had a corduroy fetish his whole life and now at the age of 36 it was stronger than ever. He...

Casey's Submissive Journey Pt. 02

by corduroysissy on Dec 14, 2017
BDSM

Debbie's eyes bulged when he looked up at Angelina, and his best friend smiled back at him. "This is my Angie, Debbie, he wanted to watch you cream his jeans." Looking through the make-up and wig he could barely make out the face of his young buddy. Casey was blown away by how good Jamie looked as a girl, he was pretty as all hell. The make-up looked perf...

Sandra and Stevie Ch. 67

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the sixty-seventh installment in a series entitled "Sandra and Stevie". If you have not read the previous sixty-six episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I str...

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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Sandra and Stevie Ch. 33

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the thirty-third installment in a series entitled "Sandra and Stevie". If you have not read the previous thirty-two episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I str...

A Showman Ch. 1

by SavageGenius on Sep 12, 2017
Exhibitionist & Voyeur

The window opened on the desktop and Stan adjusted the webcam. The profile screen appeared. Stan considered the things he wanted to reveal to his Wild Web World audience. Name? Mr. Average. Location? At home in Raleigh. Age? 28. Height? 6’2”. Weight? Above Average. He decided that if you were going to be seen on a webcam, you couldn’t really hide the truth,...

Sandra and Stevie Ch. 45

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the forty-fifth installment in a series entitled "Sandra and Stevie". If you have not read the previous forty-four episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I stro...