Sissy Bimbo Stories

10,423 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

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...

Subliminal Obsessions Ch. 02

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

*Before... She settles into a rhythm hard, steady, deep, hitting my spot inside as I moan and watch the flasher as it shows high speed pictures and all those words and phrases. Sissy. slut, bimbo, be a girl, be calm, be happy, suck cock, be happy, get fucked ne happy, sissy, slut, bimbo, live for men, live for cock, be happy, be a girl, be calm, be happy,...

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...

Open in Reader

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. 02

by sissymissyct on Sep 15, 2017
Fetish

Maddy Returns I noticed Miss Maddy getting dropped off at the main house around 10 am. I did a quick final check of the pool room and my "pink" room just in case I forgot anything and around 11 Miss Maddy came in. She greeted me warmly with a light peck on the cheek and asked, "How's Ronnie doing today? I have missed our time here in the pool house". Why do...

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...

Open in Reader

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...

Halloween Pool Party Pt. 08

by sissymissyct on Sep 14, 2017
Fetish

Friday morning cam and I was awakened with an electric shock that ran from my tits to my clit. My eyes flew open to see Miss Maddy and her girlfriend each with one of my nipples in their mouth. Pulling at the rings with their tongue, my high pitched squeal announced I was awake. My clitty tried to get hard but had no place to go. I reached to touch it and co...

Subliminal Obsessions Ch. 04

by Sissyhalo on Sep 14, 2017
Transsexuals & Crossdressers

*Before... I open my mouth and pump the last bits out of him and show him and Sarah's sort of become invisible as she recorded all of this. Alberta's standing and staring from the doorway and I show her too and her wide eyes widen more and then I swallow it. I rise up to standing and deeply kiss Leon. "That was perfect, worth all those years working for...