Sissy Shopping Stories

44,561 results
Orientation
Length
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Infinite Scroll

A Very Public Sissy Adventure

by DivinaTellsAll on Jun 4, 2019
BDSM

At Madame Vega's instruction I had spent the last hour edging myself. This is not always an easy task for a sissy who is not allowed to stroke her clitty. The edging was primarily accomplished by the use of a vibrating wand inserted in my fuck hole, and an Hitachi wand that I could rub my clitty on, as I teased my fuck hole deep inside. I had been banned fro...

Making Holly

by Sissyhalo on Sep 19, 2017
Transsexuals & Crossdressers

My name's Jamie and I moved back to my hometown. I had a lot of bad memories here and most of them stemmed from being bullied in high school and a lot of that came from Holt Thompson. A loud mouthed jock in school he was the center of the basketball team and really, really arrogant. I was a geek, a comic kid and dungeons and dragons kid and all that stuf...

Bootlicker

by GoddessVictoria on Sep 25, 2017
BDSM

BE CAREFUL WHAT YOU WISH FOR. He remembered that later, much later but by then it was too late. By then every semblance of masculinity had been totally stripped away from him. He was no longer master in his own home. How could he have been so foolish? Had there been a part of him that hoped she would find out? He had been so careful, smug even. Why shouldn...

Candi's Conversion Ch. 03

by CandiCumminz on Oct 3, 2018
Transsexuals & Crossdressers

Please read Parts 1 & 2 first. - Candi has had a long night and tomorrow she begins her sissy life properly. First thing? Shopping of course! - I hadn't slept well. I'd gone to bed horny and frustrated, and Lucy's screams of ecstasy in the other room weren't helping. Just as I'd got to sleep, a few hours after I'd crawled into bed, a loud phone notif...

Me & My Wife Are Sisters Now Ch. 02

by gayindia1980 on Sep 16, 2017
Transsexuals & Crossdressers

This story is in continuation of my last story Me & My Wife Are Sisters Now Ch. 01 ***** Next morning, we both slept quite late then our usual time, I don't know about Shivika but I was still feeling cum inside my ass. Last night my wife, Shivika was fucked by 2 sexy men in a 3some and then one of them fucked me really hard. Shivika woke up around 9:30 an...

Teased, Denied and Sissified Ch. 01

by subbieman on Sep 11, 2017
BDSM

My girlfriend and I had been dating for nearly nine months when we decided to move in together. Her lease was expiring so it made sense as we had grown closer and she really seemed like "the one." We got along great and I loved her, but, to be honest, our sex lives had recently been lagging. I hoped that moving in together might rejuvenate it, but, based on...

My Father, The Maid Ch. 02

by SissyOona on Oct 30, 2018
Transgender & Crossdressers

I awoke the next morning fairly early. My sleep had not been as restful as I would have hoped due to the revelations of the previous day. Eventually I pulled myself away from the supreme comfort of the bed and stumbled to the bathroom to take care of my morning business. As I exited the bathroom I could hear the sounds of breakfast being made from the kitche...

Sissy Amy Loves Mummy Belinda Ch. 03

by Sissy Adele Howells on Sep 17, 2017
Fetish

Nurse Sue George sat opposite her best friend, Nurse Lynda Christopher. Both looked stunning in their royal, blue nurses uniforms. Lynda was a tall women in her middle forties, with dark, long hair, tied back in a bun. She wore glasses, but was attractive for her age. The best thing about Lynda Christopher, was that she sneezed frequently and enjoyed blowing...

My Neighbor is My Daddy Pt. 02

by sissyrulez on Jul 13, 2020
Fetish

(Continued from My Neighbor is My Daddy Pt. 01) I sat in my living room, covered in Daryl's cum. I really should say my Daddy's cum. I couldn't believe I had let this happen. God I'm such a little bitch. I'm Daryl's bitch. Daddy's bitch. I looked at the list he gave me. I needed to buy panties, a butt plug, and a dildo with balls and a suction cup. How am...

Miss Guided Pt. 04

by MissMarianne on Apr 9, 2019
Transgender & Crossdressers

The next morning I went to Dr. Emily's office for my appointment and reuniting with Charles. When I arrived There were two people talking to the receptionist and I couldn't see her face. Then, I realized that the receptionist was Charles! I heard one of the patients address him as "Charlene." He looked just like a woman. Dressed in a conservative skirt s...