Sissy Boy Stories

107,893 results
Orientation
Length
Source
Infinite Scroll

A Well Groomed Sissy Boy

by keptsissy on May 15, 2018
Transsexuals & Crossdressers

"If I receive any complaints I'll diaper you and put you in your dog cage for 48 yours, no exceptions. Do you understand?" He looks down at me. I feel his dominance over me. I see the look on his face. I start to cry hard. "Please, Daddy, no. Don't do that to me, please...I'll be good...please..." I stammer through sincere tears. "Well then, all you have...

Instructional Jerkoff Sissy

by dirtywordygirl on Aug 19, 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...

Betty Finds My Story

by JackorJill on Sep 12, 2017
Fetish

The office was quiet at this time of the morning. I came in to get some paper work done. The phones never sounded better. I had put some coffee and stopped for a bagel. The applications on my desk had been piling up and that was a good thing. I never heard Betty until she was standing behind me. "Hey, you're early. Knock'em dead big guy." She was older then...

Discovering Mistress Sarah's World Pt. 02

by oneguy4fun on Sep 12, 2017
Transsexuals & Crossdressers

Chapter 4 : Introducing Miss May! Miss May's arrival seemed sudden and quick to Joe. He heard the door close downstairs. Then there was the sound of somebody running up the steps. The bedroom door flung open and before Joe could look up to see anything, he heard an excited voice exclaim, "kitty-kat!" "I think someone is excited to see you," laughed Mistres...

The Man That Owns Me Ch. 04

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"Don't be shy. Pull your panties down, baby boy. Show the man that cute little thing." He laughs, smiles at me. He's seated on the couch next to a man I've never seen before. When they entered my house I expected only him. I hurry to do as told. It's something that is part of me now. I never hesitate to do as he orders, dominant of otherwise. He owns me com...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

Mama Mia Pt. 02

by grizzley123 on Jul 27, 2020
Fetish

This story contains many themes including cuckolding, gay sex, bsdm, incest and submission. If these are not your things, please skip. This is the second installment and it obviously helps to read the first part. The starting point here: I have just finished sucking off my temporary neighbor's cock. I have been set-up by my wife and her lover to be a submis...

Being a Sissy for Viv Ch. 05

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

Mistress Viv wondered around the bed, filled with the most feminine and sissy items from my wardrobe. Her fingers stroking and examining various items in turn. The first things she picked up were some nylon panties. They were one of my earlier eBay purchases. A double layer of nylon ensured they always gave that nylon sliding on nylon feel even when worn on...

Jade in Control

by Slutboy88 on Oct 26, 2020
Fetish

I woke up still lay on the floor with my hands tied behind my back. I could still taste my own cum in my mouth after Jade had made me eat it from her pussy the night before and my ass hole was throbbing from the brutal fucking she had given me with her strap on the night before. My mouth was dry and I felt disgusting. I desperately wanted Jade to untie me so...

The Dominatrix Order Pt. 04 Ch. 03 - Femdom

by Jwwsmith on Apr 23, 2019
Fetish

Sixteen days before the next supply of Medication 42 was due to be manufactured, General Callisto paid another visit to Femininus. Upon the General's arrival, she was nonplussed when she received an invitation to have drinks with Isabella at her castle. She arrived at Isabella's residence that morning, dressed in a modest black knee length dress. Servant Bul...