Sissy Shopping Stories

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Orientation
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Infinite Scroll

Mrs C

by pantywriter on Sep 11, 2017
Mature

This is a lengthy story covering many different subjects. Be warned that some fetish concepts are explored. ***** When Mr. Caruso next door unexpectedly passed away, I attended the funeral along with my parents. I think that the entire neighborhood turned out. The Carusos were popular, friendly people and his sudden passing shook everyone. It happened in...

Vegas Sissy Wedding

by Sissytilly on Jul 6, 2020
Transgender & Crossdressers

Story: Abbie looked up at the clock as she continued thrusting her hips back and forth. Half past 3. 'That messes Wolfie's plan touched down half an hour ago' she thought excitedly, 'he'll be her soon.' As she continued her thrusting she thought back to the start of her holiday... —6 hours earlier— Abbie had arrived at the hotel in Las Vegas with her fian...

The Fantasy Twist Ch. 02

by oneguy4fun on Sep 18, 2017
Transsexuals & Crossdressers

Sunday morning was a morning for sleeping in. Dan spooned Lisa's naked body. This was not typical of Dan, as he usually preferred to sleep facing away from Melissa. Melissa was happy with this change. She enjoyed the warmth of his body. She stirred under the covers, snuggling even closer to Dan. Dan broke the morning silence, whispering into Melissa ear, "L...

Appointment by Card Only Ch. 01

by Sputnik57 on Sep 17, 2017
BDSM

She had always been so vulnerable, growing up with the other boys it was so obvious she was not like them. Now in their late teens as adulthood announced itself to the others by adorning them with bodily hair and a developing musculature, they laughed at the soft hairless form of the one who was well known to them, but only from an external perspective. The...

Sissy Dust Pt. 03

by Sissyhalo on Sep 11, 2018
Transsexuals & Crossdressers

*Before... I lose track of everything after he seeds my insides and kept going. No not everything. Three highs after the mixture entry affected me. Three times Steven came inside of me. I dimly remember the clock. And my body in some sort of perfect fuck shock after he was done and shaking with him vibrating too our hearts pounding after that and him s...

Older Sister's Nylons Ch. 01

by BlkNYLONS on Sep 18, 2017
Fetish

This took place in 1966. A time when the fashion called for women too wear girdles, garters, and shiny ultra sheer reinforced heel and toe nylons, spiked heel pumps/mules daily! A time when my fetish for nylons was young and in full bloom! You little pervert! I jumped up, dropped the high heel pump in my hand that I had held over my nose and I turned around...

Humiliated at an Outlet Mall

by willow619 on Sep 25, 2017
Transsexuals & Crossdressers

A month before my birthday my wife Mel (short for Melanie) hinted she had a special surprise planned. I dislike having a fuss made about my birthday, and even though it was my 30th I expected nothing more than a dinner at a nice restaurant. Instead, on my birthday my wife and I headed to an outlet mall, a regular activity for us. But this time we drove to a...

Humiliated Sissy Slut

by Allice on Sep 16, 2017
Transsexuals & Crossdressers

I have been dressing as a woman at home in private for many years. No one has ever seen me dressed as a sissy slut before but I do it to feel sexy. I know I would never pass as a woman for I am 6 feet tall, 170 lbs and at the age of 45 not a real trim body. My girlfriend Rachel who lives with me is must younger at the age of 35 with a young trim body that h...

Cyber Sissy Ch. 03

by missvicky53 on Sep 25, 2017
Fetish

"Good, you may begin by repaying my hospitality. I want you to clear the table and rinse the china. You may then put everything in the dishwasher. When you are finished, I will continue your training." I obeyed at once, being very careful with the china. I wondered where Megan was while I was doing my domestic chores. The answer to that came a minute later....

Neighbourhood Terror to Sissy Pt. 13

by Fibaro on Oct 7, 2019
Transgender & Crossdressers

Chapter 15 Only 10 minutes had passed since they left from the homeless shelter and they were already pulling up in front of CC's. Mark had had no time to process the humiliation he just experienced yet while he was already getting confronted by a whole new sense of dread creeping up to him. He knew Lisa meant well, but he was also sure she would get corrup...