Sissy Pills Stories

15,811 results
Orientation
Length
Source
Infinite Scroll

Mommy Adriana Convinces Andrea

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

My thanks go to Cherysse St. Claire, who was so nice and edited my story! Without her my story wouldn't be as good as it is now! Dear Readers I hope you enjoy the ride! When they finally ended their embrace, I minced towards my wife and Mommy Adriana, head bowed, avoiding their eyes. I held out the tray and waited for Andrea to take her breakfast. "Greta,...

Lonely Man Becomes a Sissy Ch. 02

by rebeldoll on Sep 13, 2017
Transsexuals & Crossdressers

I awoke groggy and confused. I normally wake up in my nice queen size bed. I didn't know where I was. I had had the craziest dreams of me being a woman and getting me ass beat and fucked. Then I realized that it was no dream. I was tied down, my arms in front of me, I was on my stomach, my ass stuck in the air, something holding my feet spread apart, and I s...

Hugo From Pode Hole

by egmontgrigor2010 on Sep 13, 2017
Romance

CHAPTER 1 The ruggedly handsome guy with long black hair and very pale complexion leaned back on the chair in the half-empty Starbucks and wished he'd chosen a coffee that tasted like coffee. Idly he studied three under thirties women at a table who were dressed like businesswomen. He winked at one and she turned away embarrassed and their heads went togeth...

Stevie's Journey Ch. 02

by gbr2004 on Oct 7, 2019
Fetish

I sleep soundly but finally wake up and realize it's almost nine o'clock. I get up and take a shower. The hot water feels so good. I get dried off and go over to the dresser and open the top drawer and there are several pairs of panties in the drawer. I pick out a red pair and slip them up my legs. They feel so soft as I pull them up. I reach in and tuck my...

Maria's Sissy Boy

by blaud on Sep 11, 2017
BDSM

A princess housewife finds it useful in many ways to have a sissy house boy in her home. But the husband insists on a precautionary measure. Before Maria came into my life, I was just drifting. I was a West Texas slut boy, whose sole purpose in life was to find the next cock to suck. I'd seen her around the apartment complex, but had no interaction till tha...

Falling into Being a Sissy

by Sissyhalo on Dec 12, 2018
Transgender & Crossdressers

My name's Sonny and well life's been pretty damned golden for me. I used to be a hockey jock in high school and was a defenseman so I was kinda big and tough and had all the usual good stuff going for me. Middle classed family, decent money for all of that, lots of high school pussy and even more in college. Being a jock in college doesn't prepare you for...

Becoming Mindy Ch. 04

by mindyrose on Sep 18, 2017
Transsexuals & Crossdressers

I have taken some shortcuts in this story to make it more readable. The process of getting hormones was a little more detailed (i.e. psychological evaluation and ongoing group therapy sessions), but would bore the average reader, lol. Although I combined three separate visits to tell this part of the story, it is fairly accurate (i.e. He fucked me on each vi...

Cockland Island Pt. 02

by Sissyhalo1 on Dec 3, 2019
Transgender & Crossdressers

I knew I was messed up in the head and didn't care. I knew I was getting brainwashed but didn't care the videos, the drugs, the sex. These nice, big, muscular, handsome guys were there eating with us as we shared a table and were being really nice to Jill and I. In my normal life people are just sorta nice, not nice in this way. It was kind of cool and y...

A Sister's Revenge Ch. 03

by Johnboy9 on Sep 18, 2017
Transsexuals & Crossdressers

I hope you all enjoy this story. I appreciate any feedback you care to send, and will respond to all who desire it. I really do appreciate any and all notes and letters received from readers of this site. Please, as the 42nd St. vendors say, be 18 or be gone (actually, in my day, it was 21, but that was years ago). Again, please enjoy. * Meanwhile, Michael...

How I Became a BBC Sissy Slut

by Satanicsissybitch on Feb 12, 2019
Transgender & Crossdressers

I wasn't always a black-owned little slut if you can believe it! Can you believe, at one point in my life, I actually refused to sleep with black men? I can't even wrap my head around it honestly. These days I belong to a number of hung black guys who use me whenever they want and now I refuse to sleep with white guys altogether! If it's not a black cock I d...