Sissy Hospital Stories

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Second Sight

by sr71plt on Sep 17, 2017
Non-Erotic

"But don't you find it just a tad bit strange?" Cliff Clayton asked his wife, Susan. Even though they were sitting knee to knee on rickety kitchen chairs, they barely could see each other through the decorated and lit pine branches. Two bushy Christmas trees, enveloping the room in a strong, eerily light, were positioned in the small living room, in opposite...

The Gynecomastia Kid Ch. 01

by Johnboy9 on Sep 14, 2017
Transsexuals & Crossdressers

This story will be told in first person narrative but this first part is written in third person narrative because the first person, or main character, is unaware of the events unfolding in this scene. ***** Inside the kitchen of her boyfriend's house Crystal makes a last ditch effort, calling his stepmom, Dr. Burns, for help: "Crystal, you're saying all...

Pink Panties

by DrLuverotica on Mar 27, 2019
Transgender & Crossdressers

It all started with a pair of pink panties. It was sometime after midnight when Jo arrived home from being on-call at the local hospital. She'd received a phone call several hours earlier about a bleeder and had to rush in. Recently her workload had become almost unbearable, but we needed the money so she was working her sexy curvaceous ass off. By the ti...

Cheap Sissy Whore To Call Girl Ch. 03

by HardSoft on Sep 15, 2017
Transsexuals & Crossdressers

My first few days at the hospital wasn't the typical hospital stay. I'd get fucked by everyone who worked there. Most of the time I was too dazed to realize what was happening but there was always a cock or a pussy that needed attention. The doctors would come in during their breaks to ass fuck me. The nurses would make me lick their pussies clean. I didn't...

A Strange Romance

by toniukcd on Sep 16, 2017
Transsexuals & Crossdressers

Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to the East Midlands. Ever since my parents decided when I was...

April’s Child

by 4glory6 on Sep 16, 2017
Interracial Love

"Annie, you take them children up third floor. They like to wear Miz. Irene out on the trip. And you, Toby, stop moonin' over Annie and get the ice chest goods into the house and in the ice box. You got ice in the ice box didn't you?" "Yes ma'am," Toby answered as he trotted out the kitchen door and down to the Buick car in the drive below. "And you, Miz....

Mistress Melanie's Gay Bar Antics

by Spar on Sep 16, 2017
BDSM

The clothes pins on his nipples were killing him ... and he loved it. He'd come to learn, over about three months, that he was Mistress Melanie's Pain Slut. Often he wondered what it was he sought more: the pain; the humiliation; or Melanie's approval. She had the ability to expertly dole out a measure of each in a way that kept him coming back for more. Hel...

From John to Jenny

by GaysonPerry on Apr 20, 2020
Transgender & Crossdressers

John put on the little black dress and became a she, her little clitty slipped out from beneath the red lace panties and she fondled the outside of the lacing. With this, she felt sexy: combined with the 'fuck me' pumps and a red bra she was about ready to be a sissy, except there was nobody around except her and her toys. All that ruined the illusion was...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

The Holiday Pt. 01

by mandiejune on May 16, 2018
Transsexuals & Crossdressers

My name use to be Frank its now Helen sissyslut and I was surfing web looking at crossdressing sites on my computer when this holiday competition came up. For some reason may be my wife had left me after finding me dressed up like a hooker! I decided to enter the competition not really expecting to winner a free 4 weeks holiday in South of France. Two weeks...