Sissy Anal Training Stories

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Left Alone Ch. 02

by fantaseeboy on Sep 26, 2017
Transsexuals & Crossdressers

Walter stood me up on shaky legs. After spinning me around to face each other, his hands grazed my bare, hairless skin until he hooked his fingers in my dress, which was wrapped around my waist, and tugged it over my hips letting it fall to the floor. His eyes wandered up and down my naked body. I had never felt so desirable and sexy before. Here I stood,...

Anal Training Ch. 01

by Catchandrea2397 on Jan 20, 2020
Transgender & Crossdressers

This is the first in a series of sissy JOI training instructions. I want to provide real instructions that can be followed and enjoyed by anyone (well by any submissive sissy wanabee). Please only read this however if you are over 18. Feedback is welcome *** Day 1: Hello pet. Are you ready to have some fun? Are you ready to begin your training? Get...

Anal Training Ch. 02

by Catchandrea2397 on Jan 20, 2020
Transgender & Crossdressers

Are you ready to be a good obedient sissy pet? Well shall we begin day 2 of training. Have you got everything I asked for last time? Good. Today you'll need: - Bra and panties - Lube - Butt Plug - Vibrator Get these things and lay them out on the bed. Go shower. I want you nice and clean. Clean now? Good. Now I want you to crawl naked to the...

Sheila's Training Ch. 01

by CeliaisAliena on Sep 15, 2017
Anal

Not for nothing are "Ghost World" and "The Doom Generation" my favorite films. I was made for a stark black bob long before I ever got one, before I saw those movies and even before I discovered black hair dye. Without it I might have ended up looking something like Lotte Lenya in "From Russia With Love." Goddess bless Manic Panic!! It's more than the hair,...

Anal Training Ch. 03

by Catchandrea2397 on Feb 3, 2020
Transgender & Crossdressers

Hello pet. Welcome back. Are you ready for the next stage in your training? Good. You're such an eager obedient pet aren't you? Such a slut. Today you are going to need the following items - Bra and panties - Stockings, ideally with suspender - Butt plug - Vibrator/dildo - Lipstick - Perfume You will also need plenty of time. I'm not going to...

Anal Training Ch. 04

by Catchandrea2397 on Mar 3, 2020
Transgender & Crossdressers

Hello Pet Welcome back. Are you ready to continue your training? Good girl. Yes thats what you are now. My little girl. My little slut. I hope you've been training as I instructed. Have you been teasing that desperate ass of yours? Good. Before we continue I want you naked and clean. Ready? Good. I need you to get a few things ready for me p...

Sissy Slave

by mikedoreilly1973 on Nov 24, 2018
Fetish

It was late friday night, and Mike had just gotten home from work, he was tired and filthy from work and decided to take a much needed shower, he went to the bathroom and noticed the door was slightly ajar, he peeked inside and saw his 18 year old daughter Samantha taking a shower. Samantha was his daughter from his previous marriage which had ended badly wh...

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Mistress Jaz's Sissy Slut

by barbiboi on Aug 30, 2017
Fetish

Mistress Jaz had invited me over to give her a pedicure and provide sissy maid service. What I got was a mind blowing day of servitude I will never forget! I arrived in the morning and was greeted by a vision of beauty. I had seen pictured of Mistress Jaz before, but they paled in comparison to meeting this incredible Goddess in the flesh. Tall, curvy, wit...

Sissy and Missy

by ChristopherDB on Feb 12, 2019
BDSM

Copyright 2019 Christopher D.B. * The central vacuum system made barely a sound as I made my way through the apartment. It was spacious and occupied the entire third floor. Although fully furnished and containing some of Countess Tori's personal items, she only stayed here a few nights a week. My feet were hurting, as the toe box on my pumps fit a little...

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...