Pimped Out Sissy Stories

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Pimped Out Sissy Bitch

by Gemsissy on Jan 12, 2018
Fetish

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit. I glanced at the phone....

Our Sissy Slave Ch. 02

by purekink on Sep 25, 2017
Transsexuals & Crossdressers

Would you be our full-time cross-dressing lesbian boislut? Of course you would. I knew that from the moment we'd made you beg to be fucked whilst dressed in a red corset, knickers and stockings ensemble. Your clothes matched those of me and my new student girlfriend, and your makeup was messed only by our juices. It was easy to make you submit after that....

Pimped Out White Sissy!

by nancyvasquez on Sep 16, 2017
Anal

Hi everyone! I haven't posted in a while, but I definitely have been having a lot of experiences. Best news is that I found a new adult bookstore to hang out in! I found out about if from a guy who I gave a blow job to in SECRETS in Jack London Square in Oakland. He asked me if I'd ever been there, and I told him I'd never even heard of it. It's a place call...

A Mistress to Obey Ch. 02

by gbr2004 on Sep 12, 2017
BDSM

This story involves bdsm and gay play. Not your thing, move on. * I can't stop thinking about what happened last Saturday. It was so much more than I expected, and frankly, I did things I never thought I would do. I had fantasized about forced fem but still was surprised how different I felt when in panties. It's just hard to feel very masculine when in a...

Money Shot Pt. 02

by GavinIsaNuisance on Jul 27, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and completely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Tanya introduces a newly sissified Danny into the world of erotic photography which gets them into a hot offer they can't refuse. Author's Note: So, I establ...

Becoming a Sissy Maid & Slut Vol. 03

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Seven: Another Day in Chantel's New Life. It's 7:30am and the alarm clock goes off. I awake to my first morning in my new sissy slave home and life as a sissy maid and slut. I get out of bed, stretch and strip nude for my enema and shower. My butthole still hurts from last night's gang rape session, but I won't protest, nor do I really wish too. In...

Sissy's Decline into a Slut Pt. 04

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Six: Chantel's Decline is Achieved, Owned by a Black Master as his Sissy Maid and Slut. I cannot believe at what is happening to me here. Master named Gage is about to purchase me and place me into slavery as his sissy maid and sissy slut. I am near in panic, I want to run away, get into my car and drive for the safety of my home. But I know this wi...

Rosie Finally Meets Jessica

by DoesAnyNameWorkOnHere on Aug 6, 2019
Transgender & Crossdressers

It was cold. Bitter cold. January always brought negative temperatures and more snow than I care to see. It's the kind of cold that gets into your bones and you can feel it for hours after being in a warm place. Not even a hot shower can soothe the chill you have inside. Short days and long nights made the month long and depressing. My only respite from the...

I am Number Four

by princessnocturne on Sep 18, 2017
Transsexuals & Crossdressers

I stood silently in the middle of my living room, surveying my very own new apartment with a weary satisfaction. I still had boxes of small stuff to unpack, dishes and books and the like, but the furniture and appliances were all in place, and the heavy lifting was more or less done. I felt a warm glow of pride as I saw it take place before my eyes, my first...

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...