Sissy Caught Dressed As A Bimbo Stories Stories

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Do You Wanna Be A Ditzy Bimbo Barbie Doll!?

by Crissy on Apr 22, 2025

The Rise of a Sissy, Bimbo Barbie Doll! What makes & is a Bimbo? Bimbo is term or slang word for a conventionally, _'golden/bleached blonde, attractive, buxom, sexualized, naïve, and unintelligent woman'. Bimbo culture, or bimbofication, exemplifies the character type of “a conventionally attractive, sexualized, naïve, and unintelligent woman.” The term...

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The Naked Bleached Blonde "Sissy Barbie Bimbo"

by Crissy on Apr 22, 2025

Did You Know? According to a study conducted on 293 female college students at the State University of New York in Albany, exposure to semen can lower symptoms of depression. And it’s mighty healthy: One teaspoon of semen contains over 200 proteins and several helpful vitamins and minerals including vitamin C, calcium, chlorine, citric acid, fructose, lacti...

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My Bestfriend's Girlfriend

by Shauna_Wood on Jul 9, 2019
Transgender & Crossdressers

When I was in my early 20's I used to play a lot of online video games. First person shooters, mostly. The Battlefield series, especially. I had started playing games online with a guy named Chris who had gone to high school with my ex-fiancé. He and I had met through her and had really hit it off. We had remained close even after she and I split. He lived u...

Being Holly

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Okay like right off I want to make it clear it's Holly now and forever. Holt's fucking dead and I'm killing anything that's left. And that's a damned good thing. See Holt was an asshole, I...he...that person I was...I was raised by an asshole. My dad and he wasn't a nice guy. He was a jock, he was a mean jock raised by worse my grand dad. Holt was part...

Subliminal Obsessions

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Finding a place in the city is rough sometimes for a good place honestly and I spent two years in a real shitty studio apartment with not even a laundry room in the building and just no room or increasingly no room. And my luck turned around after I won money. Seriously there's a 50-50 draw at work and just sort of on a whim I put my name in and I won. Not...

Halloween Pool Party Pt. 04

by sissymissyct on Sep 14, 2017
Fetish

Monday morning I was awakened early by Miss Annie releasing the air from my plug and swiftly pulling it from my bottom. I cried out from being so crudely awakened from my slumber and that got me a quick but hard smack on my already bruised bottom. "Good morning Brenda, time to shower and get ready for a big day", she informed me. "Thank you Mistress" I answ...

Halloween Pool Party Pt. 05

by sissymissyct on Sep 14, 2017
Fetish

We arrived home and Annie greeted us warmly, then stepped back to get a good look at me from head to toe, having me turn to see the full look. Satisfied with what she saw, I was told to bring in my clothes, put them away and then pick something pretty to wear as dinner would be ready shortly. Miss Maddy and Annie headed into the main house and I went about m...

Cockland Island Pt. 05

by Sissyhalo1 on Feb 3, 2020
Transgender & Crossdressers

Waking up like that I think my brain wanted not just more but to place everything that happened to me in an order that I could handle. So deeper into sissyness it was. Playing with my butt plug until I was edging myself and losing myself in it. Abby showed up. Rolled a joint and watched me. "C'mon Nikki, up, let's get you fed and working out." It was h...

Halloween Pool Party Pt. 06

by sissymissyct on Sep 14, 2017
Fetish

I was exhausted and slept until 5pm when I was awakened by a gentle kiss from Miss Annie. She took off my headphones and rocked my shoulder a bit. "Come on my sweet sleepy sissy, it's time to get you up and about. We have a fun evening planned for you baby girl". I rubbed the sleep from my eyes and saw Miss Annie's beautiful face looking down at me. "lets ge...

Re-tooled

by Sissyhalo on Mar 13, 2018
Transsexuals & Crossdressers

Re-tool your life. Re-tool yourself. Sick of not getting what you should? Sick to fucking hell of all these assholes getting with hot people they really don't deserve? Sick to hell of Liberals and Feminists making impossible to jump through hoops so that only the privileged people get to be happy? Sick of being a goddamned incel? Look we all know that...