Sissy Shopping Stories

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Carmilla's Perfume

by egyptfrazier on Sep 14, 2017
Erotic Couplings

Molly was a typical housewife who lived in a "white picket fence" life. She was a mother, cook, gardener, and a wife to a respectable businessman name George. The only problem with Molly's perfect world was her marriage. Despite his busy schedule, George didn't seem to be intimate with Molly like he use to. One day, a friend of Molly's came over to her hous...

Before I Knew Her Name, I Knew

by jimfunone on Sep 14, 2017
Erotic Couplings

It was late. The mall was closing and I wanted to get out fast. The combination of cheerful perpetual daylight and the muzak version of "Smells like Teen Spirit" was depressing the hell out of me. I passed the jean store and saw you immersed in folding clothes and restoring symmetry to the displays picked clean by rapacious customers. I did a double take. I...

Soft, White, Satin and Lace

by butterflybridgette on Sep 16, 2017
Transsexuals & Crossdressers

Almost 19, travelling home from my usual job at the take-away, and still thoroughly a virgin. Sigh. I stand on the platform in the warm summer evening, and smell the intoxicating perfume of the women walking past, and the sound of their heels on the hard asphalt surface. The sound stops, my gaze goes from her heels and follows the curve of her calf muscle in...

Just a Quickie

by lorenqt on Sep 14, 2017
Transsexuals & Crossdressers

I had to do some shopping one night, and I happened to be feeling particularly naughty. I put my hair in pigtails, put on my makeup, pink lipstick, black bra, white tank top, black thong, pink miniskirt, white stockings, and pink 6" heels. After grabbing my purse, keys, and phone, I headed out the door. I arrived at the store and parked my car. As I went in...

Caught My Husband...in Lingerie

by TheGenderBender on Sep 16, 2017
Transsexuals & Crossdressers

I had been away on a spa weekend with my girly friends so was going to surprise my husband by arriving home 4 hours early. He had been so happy for me to spend two nights in a luxury spa hotel I had to repay him the favour, and I knew just how to do it. I crept slowly into the house, and by the sounds of it he was upstairs in our bedroom, probably doing som...

To Live Forever

by Decayed Angel on Sep 17, 2017
Non-Erotic

To Live Forever     Breakfast:         Cereal with milk         Several grapes         Orange juice He ate healthy, paying close attention to a properly balanced diet and making sure he got plenty of exercise. He plann...

First Fantasy - First Task

by shyexhibitionist on Sep 13, 2017
Exhibitionist & Voyeur

Today you're going on a shopping trip. Wear something you don't mind giving away. I suggest old clothes, skirt, top, old bra and panties. Heels of course are required. Here's 67,80€, 65 plus 2,80 in twenty cents coins. Leave any other money or credit cards here at home, but bring two bus tickets and a pair of scissors in your bag. You'll be taking the bu...

How Embarrassing!

by Fred1177 on Aug 19, 2017
Exhibitionist & Voyeur

When I was 19 (back in '79), my older sister (age 32) was visiting on a Sunday and my parents were gone shopping. I sat down on a wooden seat and managed to get a huge splinter lodged in my left buttcheek. I tried to remove it myself, but I couldn't get it out. I was in a lot of pain, but I really didn't want to my sister to remove it for me. Eventually I h...

Weekend Getaway Ch. 02

by Innocent_Ty on Sep 3, 2017
Exhibitionist & Voyeur

"That was by far the best dinner with friends I've ever had" I tell you as we pull out of the parking lot. "Your friends Peter and Melissa seem to be pretty adventurous. I can't believe that you gave Melissa your toy in the middle of dinner and I didn't even know!" "That was so much fun! I couldn't help but tell her how hot you were making me when we were t...

Hitting the Hot Tub

by Dot_May_Nip on Aug 19, 2017
Exhibitionist & Voyeur

It had been a shitty week. Really bad. The Windows guys had totally fucked up an update, even after doing a week of regression testing. Well, Charlie and I had, at one point eons ago, been MS certified, so my boss said "go help them". Jeez, that was a mistake. But WE fixed it. Let's be honest, it took me more time to scratch build Gentoo on my home machine....