Sissy Clitty Stories

9,676 results
Orientation
Length
Source
Infinite Scroll

A BDSM Sissy finds Daddy Ch. 01

by Secret_sissy712 on Jul 13, 2020
Transgender & Crossdressers

As I walked back to my van after finishing up the apartment complex two men pulled up in a van and park a few spaces away. As I open my door and I take my tool belt off my shirt rides up just enough for them to get a sneak peak at the red satin thong panties popping out the top of my jeans. The fact that they do is no mistake. I wear them high and the jeans...

First time Sissy

by PR Sissy on Sep 29, 2019
Transsexual

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any s...

Open in Reader

The Journey

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

Tom couldn't believe he was wearing a CB-6000 chastity device while driving to Knoxville to actually meet face to face with Jason. He and Jason had been chatting on a kink oriented website for the last few months. Jason had asked him to buy the CB6000 and Tom found himself incredibly eager to comply with Jasons' desire. Jason had asked him to wear it while t...

A Biker Became My Daddy Ch. 02

by SissyKyliegirl on Mar 16, 2020
Transgender & Crossdressers

While I was waking up, opening my eyes to a dark room, noticing I was naked and a strange place. As I was trying to figure out where I was, I suddenly felt a massive hand grab my hip and pull me into closer, I immediately started remembering the night before. It turned me on so much, I bucked my hips back to feel his warmth and greeted with a massive hard co...

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...

Caitlin and Mistress Vicky

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

*Clack* *Clack* *Clack* The sound of my heels on the kitchen tile was distracting me right when I needed to focus. My wife, or Mistress Vicky as I'm to call her from now on, had left me quite a bit of chores to do today. I had just finished dusting and was getting ready to polish the kitchen floor when the doorbell rang. *ring ring* Swallowing nervously,...

A Natural Sissy Ch. 06

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a woman turning a man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you don't like this kind of story, but read it anyway, please don't bomb me. I warned you to go away. If you like the idea, read on, and don't forget to vote and leave a comment. More will be added if...

Mistress Emma's Revenge

by sissymissyct on Oct 15, 2017
Fetish

Hi I'm Ken. Well I was, now I'm called Brenda. Here's a bit of my story for you. I hope you don't make the same mistakes I did. Because until I got caught misbehaving by my mistress, life was pretty good. At 38, I had a great job as an office manager in charge of 25 or so employees, mostly women, a really good salary, a nice office and plenty of job securit...

A Day Alone with My Inner Sissy

by Abitinsecure on Jan 21, 2020
Transgender & Crossdressers

It started off like any other of the rare days I have the house to myself. I woke up early at sunrise and slipped out of bed and headed for the shower to cleanse myself for the fun I was preparing myself for, something I always make sure to do as my mind starts flooding with my sissy fantasies and curiosity. I would consider myself a straight guy, work a la...

First Time Sissy - The Bike Path

by Phillysissylexi on Jun 15, 2020
Transgender & Crossdressers

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to wh...