Sissy Shopping Stories

44,561 results
Orientation
Length
Source
Infinite Scroll

More Loving with Aunty Rachel

by Stonemarten on Sep 21, 2020
Mature

Following our illicit encounter on the beach, I only had a couple of days remaining of my holiday in Spain and was desperate to get to grips with Aunty Rachel at least once more before I left. Mum seemed to notice a change of atmosphere between myself and Rachel on the occasions when the three of us were socialising together.. I never seemed to have a chanc...

A Learning Experience Ch. 08

by Joscelyn2tg on Sep 19, 2017
Transsexuals & Crossdressers

"She" had been disowned by a bigoted Father, and rebuked by her Psychiatrist, claiming she'd never appreciated anything he'd done for her. Of course that last part wasn't true, but her father had just tried to kill him with a baseball bat before any of it had been said. In any case... feeling terribly angry towards everyone and everything just then, she want...

Bread and Butter

by beagle9690 on Oct 8, 2019
Romance

Author's note; This story is a Romance, and the sex occurs towards the ending. Some might not like it for its lack of vicarious luridness from the beginning to the very end. The poem John shares with Rachel; "Autumn" belongs to Emily Elizabeth Dickenson, (December 10, 1830 - May 15, 1886). She was an American poet. I chose it because it is my favorite poem o...

My Mom's Black Lover

by standingstones on Sep 12, 2017
Interracial Love

After my mother divorced she took up with a black man. I was shocked to be honest. My Mom was always so conservative and all of a sudden there is this black man at our house. His name was Jess and right from the first, I could see him looking me over. I thought I would tell my mother about my concerns, but she would never listen to me. She was getting black...

Banging My Mom's Hot Friend Pt. 01

by Eyuder on Sep 26, 2017
First Time

Summary: Falling in love with one of my mom's female friends. This woman, Amanda, she has been my mom's best friend since a long time. They were always hanging out together, shopping together, most of the time, mom would spend her free time with her. I was 20 years old and she was a 25 years old married woman, her husband was a Spanish rich man, and they ha...

First Time Show Off

by CAExhibitionist on Sep 11, 2017
Exhibitionist & Voyeur

My husband had always been bit of an exhibitionist. I was happy to help him show off his body, but I never really understood the allure. That is until one night he talked me into showing off in public. Now we're both hooked. On a Tuesday evening, we went shopping and exploring at the Pleasure Chest, a sex shop in West Hollywood. My husband said he wanted t...

Aneraulax, a mythological Creature

by Bakeboss on Sep 1, 2017
Humor & Satire

It has been said that on the little known Isle of Suburbia lives, the strange mythological creature called the Aneraulax. This isle has been lost to the modern era and it is not known whether it ever existed or merely sank from the weight of the hyperbole of its legends. Of course, one of the biggest legends is the Aneraulax, named by the Greeks and roughly...

Dressing Room Delight

by thedevilstrippers on Sep 14, 2017
Exhibitionist & Voyeur

I lay nestled in the crook of your arm breathing in hot, guilty air. I turn to my side and smile at you plaintively. I have scattered thoughts of regret and remorse but your confident smirk acts as a strong breeze and soon my head is empty. My back is sweaty and gleams in the light when I sit up from the mattress. I shudder as you run your fingertips over...

School and Mall

by Spencerfiction on Sep 16, 2017
Non-Erotic

A very short intensive tale, a complicated plot in a tiny package. You may not get it on first read; trust me and persevere ... or not, you're the reader. It is just a story, take it for what it's worth. ***** SCHOOL AND MALL - Pass it on. "Don't go too far, Katie," I cautioned, "Karate'll only be five minutes." Katie was two and fearless. I was 62 and...

My Loving Wife and the Masseur

by watchmywifey on Sep 12, 2017
Loving Wives

My wife and I have been married now for over 25 years. I call her my long-legged, blue-eyed, blonde-haired Nordic goddess. Before we got married we had flown from Southern California to San Francisco for Halloween. We visited my male cousin who had invited us to stay with him. I'll save the details of that visit for another story, but suffice it to say, we e...