Sissy Boy Stories

107,893 results
Orientation
Length
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Infinite Scroll

The Ex That Kept Me Pt. 01

by sissythongluv on Sep 14, 2017
Transsexuals & Crossdressers

She knew I loved to wear panties. She didn't know who long I had been wearing them, but she knew I did, and she had no problem with it. My ex-girlfriend, Kate, who had cheated on my numerous times, always with bigger cocks (which wasn't very difficult considering my tiny size), wanted to meet me at the mall. We had broken up, and she was dating some guy sh...

Discovering Mistress Sarah's World Pt. 04

by oneguy4fun on Sep 12, 2017
Transsexuals & Crossdressers

Special thanks to Mistress Sarah and Miss May and Miss Mill who are my motivation for this story. Thank you for your guidance and wisdom and for the privilege of serving you and writing about you. Chapter 11 Discovering the Girl in Him For the first time since he arrived at Mistress Sarah's house, Josie was left alone in silence. His cock was still thro...

Domina Katarina Goes Shopping

by pbs444 on Sep 17, 2017
BDSM

Several days ago, there was an e-mail in my inbox. It was of course from my Domina, Katarina, because the e-mail account is for her exclusive use, when she wishes to communicate with me. Because I am her sissy slut, and from time to time she finds ways for me to prove my usefulness to her. The e-mail read: "Hello, sissy slut, I have decided I wish to go...

Robin and Jimmy Olsen - Sissies Ch. 05

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Jamie Olsen hated Mondays, because on Monday morning she had to go back to being boring Jimmy Olsen after having spent all of the weekend as Jamie! Sunday evening had been disappointing. As usual she had been out on her street corner on the stroll. Last night she had chosen to look extra trampy, wearing torn stockings, her five inch heels, and her black lea...

Clitty Transformation - One Month In

by DivinaTellsAll on Jan 1, 2019
BDSM

Exactly one month ago, on a cold Saturday night in Dallas, Madame Vega and Goddess Kimberly evaluated what I had previously referred to (my entire life), as my cock. This evaluation revealed what I already knew at heart. It was far too tiny and small to be used as a cock, or even considered a cock. I begged them to allow me to embark on a quest that would...

Sissy

by rogue01 on Sep 19, 2017
Fetish

Sissy It happened at last that he was caught. His wife came home mid-afternoon with her friend Miriam and found him upstairs in the bedroom wearing a pair of her panties. Her reaction shocked him. In the hot instant of his overriding shame he was aghast to discover in her a persona he had not yet known existed. Him, a faintly domineering man, like so many...

Gym Submission Ch. 04

by AltErik on Sep 16, 2017
Transsexuals & Crossdressers

************ Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-) This story contains Male/Male sex, Male/Female sex and Dominant/Submissive themes, so if this is a problem . . . wave off! This story is fictional story based on a fantasy of mine. I hope you enjoy it and fee...

Panty Posers Ch. 03

by EROTICbearscribe on Sep 14, 2020
Transgender & Crossdressers

It was early on Sunday morning. I awoke needing to pee and slipped out of bed, doing my best not to wake Daphne. I could hear him breathing deeply next to me most of the covers on his side as usual. My roomie was lying on his stomach, his head under his pillow. He looked so sexy lying there. I felt the warm rays of the sun on my back as I breathed in his cu...

On Line and Linda

by vinceh23 on Sep 16, 2017
Romance

Linda and I had met through one of those ubiquitous on line dating sites. When I saw her photo it grabbed my attention. We all have certain characteristics in face shape, eyes, kips, those things we can't necessarily define but when we see them we know immediately that we like that face. And she was tall, 5'9", and though not slender she was not overweight....

Falling into Being a Sissy

by Sissyhalo on Dec 12, 2018
Transgender & Crossdressers

My name's Sonny and well life's been pretty damned golden for me. I used to be a hockey jock in high school and was a defenseman so I was kinda big and tough and had all the usual good stuff going for me. Middle classed family, decent money for all of that, lots of high school pussy and even more in college. Being a jock in college doesn't prepare you for...