Sex Sissy 23 Literotica Discussion Board Stories

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Recruiting of a Sissy Maid Ch. 05

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Five: Chantel Settling in with Her other Sissy Girls "Congratulations Chantel." as Maid Penny tells her today is her 3rd. month anniversary at The Jade Maid Club as they are sitting at the breakfast table with the other girls. Other girls also congratulate Chantel as well. Chantel replies, "Oh thank you all." As the girls eat their breakfast befo...

Getting Help Ch. 01

by azkelkel on Sep 16, 2017
Transsexuals & Crossdressers

I nervously sat in the waiting room for my 1:00 p.m. appointment with the therapist/psychologist. I found her through online searches, as I guess we do all things nowadays, where her credentials and location were most important to me. She received her various degrees from decent universities and chose to open up her practice in an area just far enough away f...

Recruiting of a Sissy Maid Ch. 03

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Three: Training Done, Chantel is On Her Way. Waking up back in her cell, Chantel finds that her days being trained, orientated and broken off will here with the Burrows brothers are wrapping up. Mitch enters her cell and has her come back out and back into the house with him and Nate. Mitch says, "Well Chantel, time has come for us to part our ways...

Lexi's Date

by Sissy_Sammi_ on Dec 24, 2017
Transsexuals & Crossdressers

As Lexi scrolled through the photos of lewd sissies, she felt her sissy cock press against its pink cage. She wiggled her butt against the chair to feel the plug that was in her. She felt the soft panties against her smoothly shaven bum, and smiled her pink lipstick covered smile. She checked the time, 1:23 AM, and decided that she needed to finish up and ge...

The Vacation from Hell Pt. 03

by JamesMiehoff on Dec 11, 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 This work may not be published whether for fee or free without this copyright.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...

Sarah's Husband

by JJEroticas on Mar 30, 2020
First Time

Sarah's Husband I was nineteen sitting at a table of other nineteen-year-old degenerates. We sat outside, drank rounds of coke, and everyone had their Marlboro packs obscuring the red and white striped table cloth. I ordered a TGIF burger, greasy, a favorite. My body had a secret inside shimmering of nerves, dehydration, and malnutrition from last night's k...

They didn't need to know

by minelnaz on May 12, 2020
Group Sex

If you decide to have an alternative sex life and at the same time have a family, you should consider how much to tell your children about it. I am the younger daughter and the only one from my siblings that knows about my parents swinging habit. I learned their little secret by accident a year before college. I had to use my dad's PC for a project since my...

Miss Guided Pt. 02

by MissMarianne on Mar 26, 2019
Transgender & Crossdressers

I arrived at Dr. Bill's office and he greeted me and we sat chit-chatting together for about ten minutes. Then, Charles and Emily arrived. Dr. Bill addressed us all. "I have read Dr. Price's diagnosis and report and I concur with her findings and recommendations. It's probably best that Dr. Price tell us about them herself. Dr. Em began saying, "Well, f...

Sissy Lauren Pt. 01

by CdJade on Sep 12, 2017
Transsexuals & Crossdressers

Chapter One: Adjusting To Prison Life On a cold day in September, Freddie Jones sat on a bus on his way to prison. He had been caught four months ago and had recently been convicted to five years' imprisonment on a charge of armed robbery. He was not your typical criminal. He was just a scared young, 23-year-old man who had not wanted to risk upsetting his...

Magic Panties Ch. 06

by nolfon1 on Sep 12, 2017
Transsexuals & Crossdressers

This story is a work of fiction, all characters are fictional and obviously the events are fake. You may reprint this as needed, just give credit to the author. If any differences occur between continuity, accept the one you like better as truth, and enjoy! Here's the last recap for you loyal readers out there (I apologize for the delay, life got hard, un...