Sissy Shopping Stories

44,561 results
Orientation
Length
Source
Infinite Scroll

Creating Ginger Ch. 08

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Michelle awoke to the smell of coffee, which as of late had become her...

An Evening in Red

by poule_mouillee on Aug 21, 2018
Transsexuals & Crossdressers

Jack was nervous. As a young man in his early twenties he had his fair share of fantasies, however this was going to be his first true time exploring them. And with what a woman to explore with! They had only just started dating, a few weeks all up, which wasn't enough when going around busy work schedules; but enough to know he was smitten. Victoria was som...

Ginger the Living Sex Doll

by njcaptionlover on Sep 16, 2017
Transsexuals & Crossdressers

Growing up I've always felt like I was born the wrong sex. That I should have been a girl rather than a boy. However, living in a traditional family where I was made to suppress these feelings. The majority of my teens were spent trying to be boy and not the girl I wanted to be. After turning 18 years old, I moved out of my parents' house and decided to li...

Transforming Brent

by sissymissyct on Jul 9, 2019
Loving Wives

Katherine decides she wants to live with her lover Wendy. They come up with a plan to slowly change Wendy's husband, Brent, into their girly sissy maid full time. Will his resistance be broken? I put it in loving wives but it fits multiple categories. Will he will learn to love his new role in life? Yes, The narration switches between characters. If this bo...

The New Routine:

by subservient_husband on Sep 17, 2017
BDSM

Saturday morning, I woke with Jennifer's warm body next to mine. It was wonderful and I did not move until she woke. We locked eyes and she gave me a morning kiss on the cheek. "Go ahead and make me some eggs and toast". I left her in bed to go get her breakfast ready. While I was, I heard the shower running and as I was putting it on the table, she came in...

Sarah Gets to Wear her New Panties

by SarahCD on Sep 13, 2017
Transsexuals & Crossdressers

I was posting a picture of me in ruffled panties when I remembered something naughty that happened to me a while ago. There is a fetish/lingerie shop that I love to visit. Several times I have gone there at lunch times to get panties and bras. They specialize in really sissy girly stuff. For example, I got my French maid panties there. I love to wear my blac...

Jade in Control

by Slutboy88 on Oct 26, 2020
Fetish

I woke up still lay on the floor with my hands tied behind my back. I could still taste my own cum in my mouth after Jade had made me eat it from her pussy the night before and my ass hole was throbbing from the brutal fucking she had given me with her strap on the night before. My mouth was dry and I felt disgusting. I desperately wanted Jade to untie me so...

The Cock Clock Ch. 04

by HarveyMarcus on Sep 26, 2017
Erotic Couplings

WARNING: The following story is for the entertainment of ADULTS ONLY, and contains descriptions of explicit sex. If you are not an adult, or reading sex stories upset you, or you are offended by subjects of a sexual nature - do not read any further! This story is for entertainment only. It contains adult oriented material. This is a work of fiction. The a...

Operation Pucks and Panties Pt. 01

by JPantyboyVSL on Aug 18, 2017
Fetish

I grew up a hockey fan. I've always loved the sport, and I've always had a fetish interest in being a woman, as well as serving women. I've always wanted to dress like a woman (more specifically, I have a fetish interest in wearing women's nail polish and wearing women's underwear). Everytime I buy the SI Swimsuit, issue I picture myself wearing those gorge...

Sissy Stretching for Princess T

by Subboi23 on Apr 15, 2020
Fetish

I balance my phone up against my dresser, take a deep breath and wait patiently for further instructions. I had already received orders to be dressed in my pink negligee with no panties (or underwear of any kind) on and my butt plug inserted by 7 pm. I was in position 10 minutes early and was attempting to clear my mind and focus solely on obeying whatever o...