Sissy Halloween Stories

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Sissy Son Taken to Costume Party

by JD2100 on Sep 26, 2017
Transsexuals & Crossdressers

I was making my way to my moms and dads house to house sit for them as they were going to a party that night and I had agreed to be there to watch the house and hand out candy. I was going to be alone in the house. I loved being all alone as it gave me a chance to partake in my fetish of dressing up in girls clothes. My sister still lived there and she had s...

The Story of Keith

by KaseyLegs on Dec 25, 2018
Transgender & Crossdressers

It all began in October of 1998. Keith was working a temp job at a warehouse that was running out at the end of the month. A bunch of the guys would go out to Hooters after work on Fridays, almost like clockwork, and Keith usually went with them. He'd go with Neil and Alan to the bar next door, that had pool tables, cheaper beer, and better wings. Two of th...

Wife in Control Ch. 05

by wifetoy on Sep 25, 2017
Fetish

Or maybe a dance fully dressed and made up for ballet. Stretched and rehearsed to dance any male pride away. This is the fifth chapter of my wife's execution of the punishment poem I submitted to her suggesting ways to atone for my inability to control my orgasm. Please read the earlier chapters for the full poem and the humiliations I have been forced to e...

Mrs. Claus's Predicament

by tcs1963 on Jan 7, 2019
BDSM

Wrote this story right before Christmas, Edited and proofread by my friend, TakeMeDown... ***** It was Christmas time again, and everyone was very joyful at the North Pole. Toys were being made on every table, hot chocolate was brewing and smiles abound. It was a beautiful holiday scene, with the exception of Dear old St. Nick being mysteriously absent....

A Midnight Swim

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

Relaxing by the apartment's pool one Sunday, I relived the previous evenings midnight swim in nothing more than my long baby blue Eva Picone silk gown. The water had felt so good flowing between the silk and my nude body and the walk back to the apartment even better as I had a raging hard on from the clinging sensation of the silk over my drenched body. I...

Mistress Chronicles Ch. 05

by MistressMtoyou on Sep 25, 2017
Fetish

Background: This story involves my on-line subject Nancy, who I introduced in Mistress Chronicles 4. We've had no in-person relationship. In fact, in all of our sessions Nancy has never actually seen me. I have sent him pictures that I have told him look similar to me, but never an actual photo. * By way of background, Nancy is a computer nerd. Brilliant...

A Sissy is Born Ch. 03

by 0ra11yfix8ed on Sep 16, 2017
Transsexuals & Crossdressers

As the title indicates there are two previous chapters. They are quick reads and even if you've already read them a quick review will enhance the enjoyment of this installment! * When the reality of my situation became clear I began to panic. I was seated in a woman's car dressed as a whore and I had no idea where my regular clothes or car keys were! I be...

The Appraiser

by ctlthrmn on Sep 13, 2017
Transsexuals & Crossdressers

The seminar started at the local Marriot today. I, as the lead appraiser for my office was the main organizer for it. We had brought in one of the best appraisers in the East to share his expertise in appraising and developing a larger client base. The real estate market on Eastern Long Island was hot and I wanted to capture more of the $$$ it was spreading...

The Halloween Dangler

by weftandwarp on Sep 16, 2017
Romance

The Difficult Seduction of the Halloween Dangler, Snake Cracker, Bull Dropper and Pacifist Contender. * Christie was ready. Dressed in black with a tall conical hat and carrying a straw broom. She'd even had time to paint her face black. And her legs. And her arms. She'd been ready for a while, was extremely excited, and I was the slow poke. I didn't reall...

You're Like a Little Boy at Times Ch. 04

by Myneed on Oct 11, 2017
Fetish

This is a femdom love story that will make most sense if the chapters are read in order. James is becoming helpless as Mel dominates him and molds him to her will. The characters don't seem to want to engage in safe sex, but in the real world we should. Enjoy. All characters are over 18 Chapter 4 I received a flyer in the mail. Nowdays it is unusual to...