Sissy Pimp Stories

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Orientation
Length
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Infinite Scroll

His Sissy Whore Pt. 02

by laumadhr on Sep 16, 2017
Transsexuals & Crossdressers

Hey guys, I'm back with part two of His Sissy Randi... Thank you for soo much love on the previous story. As always, please send feedback (positive or negative) to my profile. Please read part 1 before this, or you will not have full context. ~~~~~~~~~~~~ I looked at the makeup bottles...liquid eyeliner and mascara, lipstick, and some jewelery. He came to...

Simply Friends

by puzziboi on Mar 30, 2020
Transgender & Crossdressers

"Hey, Eli," the common law wife and mother of two spoke into her cell phone. She paused a moment then said, "We're around the corner for your place." Valencia Williams ended the call. She looked at her husband, Durrell, who was driving the cash rental car. It was a metallic white gold 2010 Volkswagen Passat station wagon. Durrell, at 34 years of age, was a...

Little Sex Toy Ch. 06

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

Squatting on my heels, feet just up under the curve of my cheeks, I can feel the ruffles on my sissy sox up against my bare legs. They would tickle if I weren't so afraid and focused on doing what he demands I do in front of these men. My knees pushed up toward him and spread wide, don't dare hold them together, don't want to get slapped, I feel his hand o...

AliExpress and Sissy Downfall Pt. 06

by His_fag_wife on Mar 6, 2018
Transsexuals & Crossdressers

"Ok, now you've been fed, back in the chair and Candice will get your make up done, so that you are as pretty as you can be when you return to your Mistress and Master." "Get all that mess cleaned off her face please Candice and start making her up to look pretty." "Yes Miss Bell." Charlie got back in the chair and Candice prepared to make her look as pre...

Ginger the Living Sex Doll

by njcaptionlover on Sep 16, 2017
Transsexuals & Crossdressers

Growing up I've always felt like I was born the wrong sex. That I should have been a girl rather than a boy. However, living in a traditional family where I was made to suppress these feelings. The majority of my teens were spent trying to be boy and not the girl I wanted to be. After turning 18 years old, I moved out of my parents' house and decided to li...

A Phone Call

by trixie_leigh on Sep 2, 2017
Fetish

--Welcome to Mistress Wanda's World of S and M. THE home for ALL your most sick and twisted fantasies. Feel the sting of her whip. Hear the crack of her lash. Unleash your most INTIMATE desires. --If you're over 18 and have a credit card, enter the number now. --First time callers— [XXXX YYYYYY ZZZZ] --(laughter) --Very good ... Slllaavvvvvve. --Now, l...

Easy and Hardy

by Tiberius_Daniel on Aug 6, 2019
Loving Wives

Don't miss this modern fable. It's a fictional story, has nothing in common with reality. Please don't suppose anything; I give you only original stories. For local flavor, I used English and London words and phrases. (Example bare means a lot, fag= cigarette.) ***** First chapter For today we have two couples who lived in Chiswick, where rents are high...

Letting My Wife Cut Loose Ch. 04

by weaponx on Sep 17, 2017
Loving Wives

As the video continued, I watched in amazement as Beth's pussy welcomed Jeff's throbbing cock in one gentle push. Within seconds Jeff had completely submerged his cock into her pussy. As soon as he had rested his loins against her back side completely entering her, the camera panned back to show Beth's body. Beth's head pulled back and her arms pulling again...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

A Mistress to Obey Ch. 03

by gbr2004 on Sep 12, 2017
BDSM

I woke up when she whipped the cover off the cage. I had been able to curl up enough to sleep on my side but when I tried to move I was very stiff. She opened the cage door and I backed out. She told me to go take a nice long shower and that my clothes would be on the bed when I finish. She was wearing a pair of tan slacks and a yellow blouse and looked like...