Feminized Sissy Stories

6,870 results
Orientation
Length
Source
Infinite Scroll

Cleaning Her Kitchen

by michaelssubmission on Sep 17, 2017
BDSM

"Today you will learn to clean the kitchen, but more specifically how to clean my kitchen," she said, looking directly at me. "You will begin by going to the cabinet above the stove and removing the box that is there. Place it on the floor next to my feet. I reached up and opened the cabinet. I am not tall and it meant reaching up on my toes. Naked while sh...

A Girl And Her Sissy

by TollWard on Sep 18, 2017
Transsexuals & Crossdressers

Life is good. Life is really, really good. As I write this I'm sipping on a very expensive wine and wearing a very expensive dress while sitting in my very expensive apartment. I no longer work, having not needed to earn my own income for little more than a year now. That probably leads you to wonder how I pay for all my nice things. Well while I enjoy my lu...

Tee and Gino Ch. 02

by gin0aki56 on Sep 16, 2017
Transsexuals & Crossdressers

The first time had been, well it had been a lark. I regularly look at the craigslist personals to see how much loneliness there is in the world at any given moment, admittedly it's not the most accurate of indicators, but that's the excuse that I use. I usually don't put too much stock into the fantasies or desperate pleas I find there, but hers had been dif...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

FILF (Fathers I'd Like To Fuck) Ch. 03

by Angelscuck on Sep 17, 2017
BDSM

A couple of weeks had passed since our last adventure and I decided it was time to further Sandy and Shelly's sexual education. They had called me several times during the last week and I knew they were anxious to have their next lesson. This time I had planned something very hot. While teaching gymnastics at the alternative high school several years ago...

My Master

by SissyKaty on Mar 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I pulled into the driveway to my house and I was disappointed to see my future mother-in-law's car in the driveway. "Oh great" I think sarcastically. I'm not looking forward to interacting with her so soon after getting off work. I had just come from a long day working in IT for...

Sissy Lesbian Rita Meets Lisa

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my two already published stories: 'Miss Johnstone's Lesbian Sissy Slut' and 'Further Training as Sissy Lesbian'. I sincerely recommend reading these stories first as it provides background for this one. My stories have been well received and I would like to thank you all for the positive response! Enjoy and please ta...

Yeliza Awakens Pt. 01

by Yelizaveta on May 11, 2020
Transgender & Crossdressers

First of two, hope you like it. Based on real experiences. Part 1: Morning excitement Early on a Saturday morning, he came out of a gentle sleep. He was giddy. As he had been every time. This time was special however, this time he had done the most preparations ever for this event. His legs and pubic area rigorously shaven the night before. His clothes fe...

My Friend Ashley Ch. 05

by jealouscuck on Jul 29, 2019
Transgender & Crossdressers

Things were no longer in the experimental stage. Gretchen had set me on a path to feminization and Ashley was following her lead. Ashley had already broken one of her restrictions. She had allowed Gretchen to perform oral sex on her. The distinction that I was performing oral sex on the women while dressed as a female. When Gretchen ate Ashley's pussy, Ashle...

Crossdresser Evolution Ch. 03

by pantyhigh on Jun 12, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties, though there was still a feeling of shame surrounding it. I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's pantie...