Sissy Shopping Stories

44,561 results
Orientation
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Infinite Scroll

The Challenge - Wear a Thong

by taraterry on Oct 11, 2017
Transsexuals & Crossdressers

There is something deliciously naughty about a boy wearing women's thong panties for a day, after all, the first time you wear a thong all day long, especially on a week day, you will be going about your normal routine. Whether it be to class, to work, or whatever you normally do, you will have it on all day, even when you're not fully sexually aroused. Why...

Neighbourhood Terror to Sissy Pt. 07

by Fibaro on Apr 23, 2019
Transgender & Crossdressers

Mark regained consciousness when Stephanie pressed her lips against his and started pushing his load of cum in his mouth. He had only just sucked a load off of Linda's toes and now he was swallowing yet another one. Every time he came here he seemed to get stuck with a taste of cum in his mouth. Only made worse by the way in which he was fed the load. Well a...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...

Mommy Adriana and the Video Booth

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

Dear Readers, I never imagined to get so far but funnily the more I write the more ideas I get. I hope you still enjoy the ride. * I closed my eyes. Not wanting to see people staring at the bound and gagged bundle which I had no doubt they were, especially when we stopped at red lights. In fact I didn't see where we were going. The only thing I...

Sissy Awakening Ch. 02

by Torbjornson on Oct 19, 2020
Transgender & Crossdressers

- A Sissies Choices - It was sometime in the middle of the night I woke cold, just laying on top of the covers I realized I was hungry as hell too. Still wearing the clothes they had put me in when I left the spa, I wrapped a blanket around my shoulders and headed for the kitchen. Standing there hungry but not wanting to really make anything I saw the jar...

Transforming Brent Pt. 04

by sissymissyct on Dec 2, 2019
Fetish

In the morning I showered and dressed casually as directed by Mistress Wendy. My new black skinny jeans and a plain blouse with light day make up and my cork wedges. Some jewelry and my handbag and I was ready. Mistress wore leggings and a tunic top with her long hair tied up in a bun. Wearing flats, she was still much taller than me. We had a light breakfa...

My First Time as a Sissy Ch. 03

by SissyTara on Sep 13, 2017
Transsexuals & Crossdressers

I suggest you read the first two chapters before reading this one. I was coming to the realization I was a natural born sissy. I had sucked Raoul's cock a few times and had been feminized with the help of his sisters. I found I loved being feminine, specially wearing the clothes and makeup and I loved sucking Raoul's cock. I wasn't completely "out," yet but...

Miss Guided Pt. 03

by MissMarianne on Apr 9, 2019
Transgender & Crossdressers

That evening I went to dinner at Donna's house. Donna opened the door and was beautiful in her little black dress. She wore impeccable makeup, stiletto heels, black nylons. I felt like a frump in my plain outfit. She explained that her husband Mary Lou just got home from work and was upstairs changing. We talked and drank daiquiris for about a half hour...

Randi Michelle's Sissy Subjugation

by Randi_Michelle on Sep 16, 2017
Transsexuals & Crossdressers

To me, part of the process in my case of stripping me of my masculinity involves documenting my transformation and the humiliation that it would involve. For me it started through an encounter with a dominant man who enjoys feminizing submissive males and turning them into 24/7 gurls. It just took the right dominant man to make it happen for real. I've spen...

Sarah Gets to Write Her Own Story

by SarahCD on Jan 6, 2020
Transgender & Crossdressers

If you are an adult, looking for some kinky fun, live in the San Francisco peninsula and would like to star in a re-enactment of one of my experiences, contact me. My experiences here show what I like to do. We can write our own scenario and then act it out. I'd love to help you make your fantasy a reality. Now for my latest adventure, I found a Classified...