Sissy Bitch Stories

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The Prostate Exam Pt. 04

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by not being able to resist pushing back against her finger, forcing her finger deeper into asshole. At that point his female doctor had decided to test just how submissive he was. She gave him the option to back out if he...

Mistress In Control

by polishjoe on Sep 17, 2017
BDSM

Last Friday evening when I got home Mistress informed me that tonight was going to be a very hot night but I did not realize until later just how hot things were going to get. Mistress had dinner ready and she told me she wanted us to eat quickly so we could get straight to the "activities" she had planned. I thought it curious because Mistress usually did...

Stevie's Journey Ch. 02

by gbr2004 on Oct 7, 2019
Fetish

I sleep soundly but finally wake up and realize it's almost nine o'clock. I get up and take a shower. The hot water feels so good. I get dried off and go over to the dresser and open the top drawer and there are several pairs of panties in the drawer. I pick out a red pair and slip them up my legs. They feel so soft as I pull them up. I reach in and tuck my...

Discovering Mistress Sarah's World Pt. 04

by oneguy4fun on Sep 12, 2017
Transsexuals & Crossdressers

Special thanks to Mistress Sarah and Miss May and Miss Mill who are my motivation for this story. Thank you for your guidance and wisdom and for the privilege of serving you and writing about you. Chapter 11 Discovering the Girl in Him For the first time since he arrived at Mistress Sarah's house, Josie was left alone in silence. His cock was still thro...

Sissy Pool Wager Pt. 01

by maxy007 on Sep 14, 2017
Transsexuals & Crossdressers

My name is Max, and I'm your typical high school graduate. White, short brown hair, blue eyes, skinny, and 6'4. I never had muscles or any masculine traits other than my lanky height. I had just finished high school, and had 4 months off before university to myself! As you could imagine, an 18-year-old horny boy like myself really got into my porn, which f...

Mommy and Goddess

by force_transitioned on Sep 12, 2017
Transsexuals & Crossdressers

Andrew never saw the noose. He was uncomfortable around his new mother in law - his wife's new step mom. And rightly so - he was, after all, going through the woman's intimates since the day she entered their lives, some two years ago, shortly after the marriage. Had he overcome his guilty reaction, he may have noticed a recurring theme in their conversa...

Spanking Night Ch. 06

by Angelscuck on Sep 14, 2017
BDSM

"On your knees slave!" Mistress Sheila commanded. I immediately fell to my knees in front of the beautiful dominatrix who was standing before me. "Who are you?" she asked. "Your sissy slave," I meekly replied. "That's right slave," she said as she hooked her thumbs into the waistband of her tight mini-skirt and slipped it down to her knees revealing her...

The Babysitter Takes Over

by sissysherry2 on Mar 13, 2018
BDSM

"I know your secret." These were the words that I had both dreaded and longed to hear from my babysitter. Let me start at the beginning. I am single and have a couple of kids at home who aren't quite old enough to be on their own when I have business obligations. I share custody with my ex, who left me to be with another man, who happened to be black. I ge...

High School Fuck Slut

by TonyaTV69 on Sep 25, 2017
Transsexuals & Crossdressers

I grew up out in the country as a boy with my mother and 2 sisters. My dad was never around since he was always off working or as we found out some years later running around cheating. If we saw him at all it was on the weekends for a quick family outing to the mountains or park. Once in a while mom and dad would get all dressed up and go out to dinner. This...

The Booth in the Back

by mona215 on Sep 16, 2017
Transsexuals & Crossdressers

On my knees on the vinyl floor, the metal choke chain around my neck, one end of the chain under the pointed toe of her fuck-me heels, keeping me bent over so that my pantied ass is sticking up into the air. The sound of her crop slapping against my silky undies punctuating the mean things she says to me in a bored voice. "Real men don't wear girly panties...