Sissy Boy Stories

107,893 results
Orientation
Length
Source
Infinite Scroll

The Photographers Assistant Pt. 02

by panty_wearing_sissy on Nov 13, 2017
Transsexuals & Crossdressers

If you are under 18, please stop reading and delete this document immediately. This story is pure fantasy. It does not relate to any real events, either past, present or future, and is only suitable for persons over the age of 18 mature enough to understand, and distinguish the difference between fantasy fiction and real-life. ***** Jake didn't remember e...

The Descent

by pantywriter on Sep 28, 2020
Transgender & Crossdressers

It had to be too good to be true, I thought. No woman had ever come on to me like that before. She was pushy and for all intents and purposes, demanded that I escort her to this dinner date in the city. Sure, it was Valentine's Day, and she did admit earlier in the night that being mid-50s and single on this day agitated her; hence, she demanded my presence....

Being a Sissy for Viv Ch. 04

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

With great care I slowly pulled the 10 denier black nylon stocking up my leg. I had other pairs, but these were my best and today it was important to have the best. Cautiously I rolled up the second one and with the same deliberation pulled it onto my other leg. The feeling, of soft nylon sliding over my naked skin exquisite and exciting as always, but today...

House Rules Pt. 02

by GavinNuisance on Mar 16, 2020
Transgender & Crossdressers

Terry laid naked on Lana's couch, face down with his ass sticking up. Her cum had dried. Drowsy, and still a bit tired, Terry began to move, and stretched as he adjusted his eyes to light. He noticed the sun was setting and he was clearly there for at least a few hours. He rubbed his eyes, but noticed a peculiar feeling in his backside. "What the fuck?" He...

Ensnared by a Corset

by spinder on Sep 16, 2017
Transsexuals & Crossdressers

Warning: This story is a work of fiction and contains descriptions of explicit sexual acts between women. If this type of content offends you or you are under the age of 18 do not read it. Author's Note: This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at you...

Discovered at the Bar

by CrossdresserCaitlyn on Mar 25, 2019
Transgender & Crossdressers

It was 9 pm on a Friday night and I was just getting off work. It was a long day of running meetings and I really needed a drink. I was out of town and didn't know anyone so I decided to go to the bar by myself. As I sit down at the bar I take off my suit coat, untuck my shirt and loosen my tie and ask the bartender for a Jack and Coke. The first drink did...

Service Day 01: Sissy's Breakfast

by SissyHubbyD on Aug 7, 2019
Transgender & Crossdressers

His alarm goes off at 6 AM that Saturday. On any other Saturday he would ignore the alarm and sleep in until 10 or 11, but not today. Today is Service Day, and he couldn't be happier about it. He gets out of bed quietly, careful not to wake his wife as he does so, and tiptoes out of the room and down the hall to the empty guest room. His outfit for the day...

Becoming Her Whore

by ecdilettante on Sep 19, 2017
BDSM

Last time we parted, you told me that you were going to fuck me when we next met. You loved the fact that I've never been taken with a strapon and you promised to be gentle, in the beginning. It sent a shiver of excitement and fear through me, which made you smile. I can imagine heading to your small apartment, anxious and excited. I haven't cum for days a...

My Glorious Transformation Pt. 01

by switchhitter420 on Sep 18, 2017
Transsexuals & Crossdressers

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry. ***** About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass an...

The Sissy Diaries Ch. 1

by colettegrrl on Aug 18, 2017
Fetish

This is a story about my new life, my new way of being. I wanted to share my story so I started to record my events. I figured the best place to start was, well the beginning. Here's how it all started. * * * * * I come home to find you sitting at the dining room table, laughing and drinking with a tall, dark, well-built and handsome black man. You introdu...