Abused Sissy Anal Stories

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Abuse my Sissy bitch

by Red10Dog on Mar 3, 2020
Fetish

This is a story from the sissy's wife. Telling you a story that happen a few weeks ago and it was orgasmic! So late one Saturday night I put my sissy bitch in a teddy, nylons, cock cage and a jeweled anal plug under his pants and shirt and headed out to the casino. I am not ready dress him out in public yet, but I am getting close. I decide to slut mysel...

Simon Sissy Slave Ch. 03

by Timewarp10 on Jul 30, 2019
BDSM

Mr Berne watched with satisfaction as the sissy paraded in the post room. Sissy walked gracefully in high heels. His ballet training made it easy. He knew how to walk like a woman. He had practiced, and he could walk with a book balanced on his head. It gave him poise, and the high heels gave elegance to his calves. The skirt was short enough to look slutty,...

Dinner Date with Mommy Pt. 04

by SissyStoryTime on Dec 3, 2018
Transgender & Crossdressers

Disclaimer - This story includes the following themes: Femdom, sissification, feminization, forced-bi, forced cum-eating, butt plugs, anal play, strap-ons, spanking, humiliation, CBT, chastity, and domestic servitude. If these themes do not interest you, then this story isn't for you, sweetheart. For everyone else... This is it. What you've waited for. Th...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Developing Emma Ch. 03

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

As Kurt caressed Emma's sweetly pronounced bottom, she realised she had never felt so feminine before, despite her newly freed cock standing stiff in nervous anticipation. She looked at the powerful male and the leering male audience; the few females there would now witness her being used as a woman. Kurt's large stiff cock rubbed against her belly as he mov...

Dinner Date with Mommy Pt. 01

by SissyStoryTime on Nov 20, 2018
Transgender & Crossdressers

This is Part 1 of an update on the sissy Sophie and her cruel but loving Mommy, Amanda from the story Meeting Mommy (https://www.literotica.com/s/meeting-mommy) It contains numerous perverse and offensive themes that I'm sure you'll all eat right up. This story includes the following: Femdom, strap-on, implied forced-bi and cucking, enemas, butt plugs and...

Fukee Sukee Beach

by JamesMiehoff on Nov 19, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

My Initiation

by lockedupslut on Sep 13, 2017
Transsexuals & Crossdressers

(This story is a work of fiction. If you don't like erotic stories that contain cross dressing, heavy gay themes and water sports please just don't read it. Thank you.) * I was determined. This weekend it would happen. I would loose my gay virginity and complete manhood. The hard way. Tonight would change everything. Until now I've never had sex with a ma...

Teacher Made Me into Sissy

by johntamilandrea on Sep 13, 2017
Fetish

HI! I am Sissy Andrea. This is one my fantasies about my teachers. This story is about feminization, fantasy. If you don't like these topics Please don't read. ALL THE CHARACTERS IN THIS STORY ARE ABOVE 18 YEARS OF AGE. My special thanks to "mywifesslave" for helping me in editing this story. ***** The story happened when I was 19 years old I loved sho...

Jack and Jill Pt. 03: Anna

by candyflosslover on Jul 13, 2020
Loving Wives

The next day Jill was at work in her office, a parcel had arrived for her and when she opened it to her delight she saw it was a double ended dildo. She had ordered it some weeks ago so she could use it with her sissy husband. It was longer and thicker than she imagined and she felt heat between her legs at the thought of what she would do with it. She was s...