Sissy Shopping Stories

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Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...

Sissy Shopping with Princess T

by Subboi23 on Apr 1, 2020
Fetish

I excitedly pull my tight red lacy panties up over my small, limp penis. They feel so nice. Tight, but soft, containing the perfect amount of room to hold my little package. My penis does not attempt to get hard despite the pleasure, if anything it seems to shrink a bit in order to fit more comfortably. This was my first time seeing Princess T without her in...

A Sissy Shopping Trip Ch. 01

by cwsissy on Sep 16, 2017
Fetish

My wife, Cindy, and I were in the bedroom getting dressed for a party at Tim and Karen's place. They were good friends that we had known for even before our marriage four years earlier, with whom we had shared a lot of good times, including many a camping trip and tipsy card game, always with plenty of hot talk rife with innuendo. Well, technically, Cindy w...

A Sissy Shopping Trip Ch. 03

by cwsissy on Sep 16, 2017
Fetish

We were quickly through the checkout and on our way again. Cindy dragging me by the hand toward the mall entrance. "C'mon, lets go. We have some more stops to make and we haven't got much time." Our next stop was a high-end shoe store just outside the department store. I had lingered outside that same store many a time, admiring the sexy heels on display i...

A Sissy Shopping Trip Ch. 02

by cwsissy on Sep 16, 2017
Fetish

At the car, I headed for the driver's side as Cindy opened the passenger door. Before I could take more than the first step her almost shouted exclamation, "Excuse me!" stopped me in my tracks. I looking warily at her, wondering what was wrong. "Come on," she smiled tightly, "girls ride over here. I'll take care of the driving today." My macho pride rebelled...

Another Sissy Shopping Adventure

by sissysherry2 on Jul 18, 2018
BDSM

In my last story, I related a story about a mistress who gave me a sissy assignment several years ago. This involved going to a mall and getting a makeover and getting girly clothes. Like the other story in this topic, there's no sex just some good old fashioned humiliation. This is the latest adventure and I hope you enjoy it! ********************* I h...

Uurf Ch. 05A

by Beatnic_jazzman on Sep 16, 2017
Sci-Fi & Fantasy

We had breakfast with them, an assortment of dried fruit and honeyed seeds, compacted into a bar. And more of the cookies from the barrel, one for now and one for later. We said goodbye to the girls, and Davina, she gave Martin a long lingering kiss as they parted Alice turned and beamed at me as we left, a radiant toothy smile. Like the duchess's cat, on...

Cyber Sissy Ch. 01

by missvicky53 on Sep 25, 2017
Fetish

It was a Saturday afternoon when my submission to my wife began. Megan had gone to do some shopping at the local mall, and knowing her as I did, I knew I'd have at least three hours to surf the web. My favorite sites were those that dealt with the feminization and submission of men. With this in mind, as soon as I heard her car leave, I powered up my compute...

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...

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...