Sissy Friends Stories

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Becoming a Sissy Cuckold Ch. 02

by Pantieslave on Mar 26, 2019
Fetish

Beth was now fucking Jerry every 2 or 3 days and each time they had sex Dan was required to be dressed in girly clothes and made to watch them as well as to video them. Beth loved watching the video's with Dan on those days that she didn't have sex with Jerry. Dan was also required to suck on Jerry's cock getting it hard so that he could fuck Beth and Dan wa...

Ultimate Sissy Weekend Ch. 06

by SissyTwinkleToes on Feb 4, 2020
Transgender & Crossdressers

Susie wonders if she'll ever get used to the horn honks. The gasps. The shouted comments. The whispers. The cruel laughter. She is stood with her sissy sister, Tinkerbell, in her pink OTT sissy dress she's been trapped in for over two days now, on the corner of the bad neighbourood where she now lives. It's 7:45, and she's been stood in public for almost two...

Cockland Island Pt. 04

by Sissyhalo1 on Dec 16, 2019
Transgender & Crossdressers

It was one of my first lessons as a sissy that I learned on my own. New girl only appealed for some men. And there were all sorts of hotter sissy girls there just working it in the food hall and other places. With real breasts or close enough, with great asses that were getting attention. And as femmed up my brain was there was still this sort of competi...

This is What I Want

by bisissystephenie on Jan 22, 2020
Fetish

My wife Pam has started going out for a "Girls Night Out" and this time she came back a little tipsy. And very late! She knows how I love to give oral sex to her and she hardly ever says "No". We went to the bedroom and she laid back on the bed. I got in my position, on my knees and between her legs. I started kissing her knees and going up. She stopped m...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

Humiliated Sissy Slut

by Allice on Sep 16, 2017
Transsexuals & Crossdressers

I have been dressing as a woman at home in private for many years. No one has ever seen me dressed as a sissy slut before but I do it to feel sexy. I know I would never pass as a woman for I am 6 feet tall, 170 lbs and at the age of 45 not a real trim body. My girlfriend Rachel who lives with me is must younger at the age of 35 with a young trim body that h...

Sissy Girl Forever Pt. 01

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

The call from Mistress Andrea made my day. I hadn't seen her for over a week and was looking forward to playing with her & having my chastity finally removed. You should know that Mistress and I have known each other for many years and have I always enjoyed being her sissy sub. Lately she has been training me to be more feminine in appearance. I have been r...

Momdom a sissy son's wish

by Viking973 on Jun 20, 2020
Transsexual

Intro: You never had much luck with the girls in high school. You had a few girlfriends early in high school but the last 2 years before college was rough. It had come and gone, you enjoyed it, you weren't an outsider and had many friend groups but you never went out to parties or out of school to meet up with friends. You enjoyed video games and porn too mu...

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Feminizing First Step Ch. 06

by antares34 on Jun 1, 2020
Transgender & Crossdressers

(All characters are age 18+) Today my mom was having her friends over for a pool party in our backyard. They had been here all afternoon --mainly lounging around the secluded swimming pool and patio area. Michelle had been first to arrive. She was my mom's old roommate from university and came wearing a black bikini and floral print sarong. Next was Kendra...

Another Submissive Slut Ch. 07

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

Getting ready to go anywhere was beginning to take more and more time. Cleaning myself properly just encase I encountered Ms Shawna or Mr Lennie during my excursions entailed various time consuming activities that a well presented sissy just couldn't ignore. I viewed my naked body in a full length mirror searching for flaws. I now kept myself smooth, hairles...