Sissy Doll Stories

23,968 results
Orientation
Length
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Infinite Scroll

Karate Girls Ch. 1

by jabberwok on Sep 17, 2017
BDSM

It was my senior year in High School. Things were looking good. I was going to be on the honor role. College was a surety! All is well. Both my parents worked as reporters for a nationwide newspaper. My dad came home in November with his big break. A sixth month Africa on-site story about Witchdoctors and their "supposed" cures. The newspaper offered the tr...

New Rules

by skinnysailor on Sep 23, 2019
Transgender & Crossdressers

It began several years ago. Shortly after John’s death. I was out for dinner with my best girlfriend, Margaret. “Donna, honey, it’s been eight months. I know you want to keep working, and stay busy, and you love your job, but really, you should get a maid to do the housework. You could come home and just relax. Keith and I love our Sally. She cooks and clea...

Another Submissive Slut Ch. 05

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

By the time Mr. Lennie had arrived I was once more primped and preened. She laughed meanly as She put me through my paces while awaiting His arrival. Harping at me mercilessly that Mr. Lennie would make me suffer painfully for my inadequacies. The sudden sharp knock at the door made my heart flutter and my knees tremble with anticipation. My dickette bell ti...

A Picture Perfect Sissy

by meeah sue on Sep 16, 2017
Transsexuals & Crossdressers

"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted what he was doing to be okay. It was dreadfully important to be okay. Kare...

Transforming Brent Pt. 05

by sissymissyct on Dec 2, 2019
Fetish

I awoke early, partially due to the pressure of morning wood in the chastity. Once I settled down, I showered and slipped on a robe and quietly made my way to the kitchen. I quickly familiarized myself with the layout and, finding what I needed, started cooking a nice breakfast for my mistresses and myself. Ham and cheese omelet, OJ, toast and sausage, along...

Lulu's Lockdown Diary

by lululuvsblack on Jul 6, 2020
Transgender & Crossdressers

Day 1 So, with this virus we've all been told to stay home and not have any physical contact with people outside, not get together in groups at all, and not even step out of the house if not completely essential. We're locked down. I guess it wasn't a great time to move in with a couple of guys I barely know, but there you go. There's nothing I can do about...

Sissy Wife Adventures

by Maddylim on Apr 4, 2016
Transsexual

You open your eyes and turn to the alam clock on your bedside. "Seven a.m.," you whisper to yourself as you stretch your arms out wide. You pull down your blankets to reveal your slender and smooth body wrapped up in a very cute pink babydoll that barely covers your privates, which themselves are covered by a sexy pink thong. Your long bpack hair l...

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Lesser of Two Evils

by Andi_Lembke on Sep 25, 2017
Transsexuals & Crossdressers

[So to update you all. I'm sorry I haven't completed any more chapters of NWTBYG or Porn Princess. They're in the works, but creation, and good storytelling takes time, something I have less of now. I left my receptionist job to take a writing gig, and all my writing energy is going into that, but my passion for hot stories smolders intensely under the surfa...

Young Master Ch. 02

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

There I was, still impaled on a shemale's cock, one belonging to what was supposed to be my sissy slave, wearing her bra, her cum on my cheek along with my post-fuck smeared make-up, and my cum running down the full length mirror. "I fell" wasn't the best explanation for what happened, but it was all I could think of with my step-father's hulking frame loomi...

Skins vs Boys

by Couture on Sep 14, 2017
Fetish

Please do not read if under 18 years of age, or offended by sexually explicit stories and situations. (TG, FM, femdom, anal) (c) 2001 Couture * * * * * The biggest football game of the year was almost over, and my husband sat next to me angry and blushing in humiliation, while I cheered. Call me a bitch, but I took extra pains to rub it in. "Wahooo! The Sk...