Sissy Shopping Stories

44,561 results
Orientation
Length
Source
Infinite Scroll

Jasmin wears the pants

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

This story is fictional. You know the drill: If you are under aged or don't like TG stories don't bother reading any further. All rights are reserved. If somebody wants to publish this story somewhere else please contact me first. My thanks for editing this story go to alwaysupforyou2004! Jasmin wears the pants By Greta I had just arrived in New York for...

Sissy Shopping Adventure

by sissysherry2 on May 15, 2018
Transsexuals & Crossdressers

This story involves pure public humiliation and not any sex. So if this is your thing read on but if you're looking for a sex story... well there are plenty of those on this site but this isn't one of them. This is based on an actual experience that happened to me. In past stories, I've gotten comments from readers that they seemed far fetched and maybe th...

Kimmy's Discovery Ch. 03

by Deviana on Sep 16, 2017
Transsexuals & Crossdressers

i heard the click of my .. of Dougie's high heels and it was like everything fell silent. i walked around the kitchen, around and around, wanting to hear that click, to have the sound so deep in my mind. i took one of the VS 120s and then a pretty pink lighter that was on a side table- i have to find one of these for me- and lit the tip, feeling the filter e...

Dominating Sugar Daddy

by LittleDickSissy on Jul 3, 2018
Erotic Couplings

The sissy cuckold was at the ATM withdrawing cash for his Mistress. He needed cash for her nails, her new dinner attire, and makeup. As he made his withdrawal his little dick dripped precum in his purple lace panties. He always got turned on every time his Mistress provided strict instructions to him, and of course whenever she played without him. "Now tell...

Sissy Boy Secretary Ch. 03

by Hotenuf4u on Sep 19, 2017
Fetish

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you! After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in...

Sissifying Addictions

by Sissyhalo on Nov 25, 2017
Transsexuals & Crossdressers

They say you're born gay, they say you can't catch gay, that you can't be made into something you don't want to. That somewhere deep, deep down you really want it. It's somewhere in between and none of it either. It's actually so much like dominatingly slick, sinking, drowning...so very like that first time you sink into sweet sissy ass. It started for me...

Surprised Slaveboy

by MsCarol on Oct 15, 2017
BDSM

"Come on slave, out of the cage!" barked Mistress Amanda. "I hope you slept well in that little space. You'll need your energy for today!" As the door to the 24" high 3 foot square cage swung open, Michael crawled out as gracefully as he could, not wanting to earn another session bound over the spanking horse like the last time Mistress deemed him as "ungr...

The Ex That Kept Me Pt. 01

by sissythongluv on Sep 14, 2017
Transsexuals & Crossdressers

She knew I loved to wear panties. She didn't know who long I had been wearing them, but she knew I did, and she had no problem with it. My ex-girlfriend, Kate, who had cheated on my numerous times, always with bigger cocks (which wasn't very difficult considering my tiny size), wanted to meet me at the mall. We had broken up, and she was dating some guy sh...

Trip to LA Pt. 02

by gbr2004 on Mar 3, 2020
Fetish

This story is just a figment of my imagination and shouldn't be read if you aren't into forced fem, sexual service and discipline. Otherwise, I hope you enjoy the story and I love to hear comments about my writing. *** All I can think about is how out of control this all is. Here I am, in LA, god knows where, dressed up in pink and white and looking like...

Developing Emma Ch. 03

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

As Kurt caressed Emma's sweetly pronounced bottom, she realised she had never felt so feminine before, despite her newly freed cock standing stiff in nervous anticipation. She looked at the powerful male and the leering male audience; the few females there would now witness her being used as a woman. Kurt's large stiff cock rubbed against her belly as he mov...