Father Sissy Stories

71,718 results
Orientation
Length
Source
Infinite Scroll

Introspection

by Sissy_Sammi_ on Jun 19, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. *** *All characters are 18+ years old ***** Jimmy was born into a small family in Colorado. His mother was a beautiful woman named Dianne, and his father was a gruff working man named Thomas. If only kids could have been given a choice to be born, Jimmy would have chosen otherwise. He...

A Missy Affair

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

I knew I was being careful. I thought I was being clever. But I never thought I could be caught in such incriminating circumstances by of all people my sister-in-laws husbands parents. I was playing the good brother-in-law by doing a bunch of minor home reno's for my wife's sister and her husband. To my delight they trusted me implicitly and left me alone in...

Getting to Know Me Pt. 02

by eviltwin52 on Oct 5, 2020
Transgender & Crossdressers

I was still excited about what had happened yesterday and was so looking forward to meeting Butch again today at noon. The clock seemed to be stuck between 10:30 and 11:00. The morning passed so darn slowly. Remembering my instructions, it didn't matter what I wore as long as I wore some of my sexy underpants. I selected a maroon pair of the full backed bik...

Black Sissy For Black Dominatrix

by Samuelx on Sep 1, 2017
Group Sex

As a Black mistress, I totally love it when my Black male Sluts dress up for me. Gleefully I slid my strap-on dildo into Reginald/Slut Gina's ass while spanking him and cussing him out like the bitch he is. The big Black dude is now wearing a frilly pink dress, red panties, stockings, and a wig, and his ugly mug is well-made up. Transforming macho Black truc...

Young Master Ch. 04

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

"I can explain..." I was standing in a French Maid outfit, with a sissy's cum still dripping from my chin because as usual she missed a spot, and I had just been caught bent over a desk getting pounded from behind...all I needed to make it the perfect shit storm was for Dale to notice my cock was stick disturbingly hard in my panties for some mind boggling r...

Sissy Academy

by Cynthia Sissy on Jan 2, 2019
Transsexual

(feel free to message me about anything! I'd love to hear from my readers :)) The alarm beeps away as you groan at the sound of it. A cool breeze rustles the curtains, letting the sun peek through. Pushing your hair to one side, you check the time. "Oh, it's still early," you say, pushing the sheets away to reveal your blue satin panties and chemis...

Open in Reader

Becoming a Sissy Maid & Slut Vol. 13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Two: Satin, Ruffles and Lace, Sissy Maids contracted out to Work. Monday morning and I arise as typical at 7:30am, enema, shower, shave do my makeup and put on a maids dress for the day. Today it's back into a black satin one. Master told me though to put on black back seem pantyhose for today which I dutifully do and make sure the seems are...

Mother Dear Pt. 12

by keptsissy on Sep 14, 2017
Fetish

My white frilly lace panties delicately pulled down passed my stocking tops, so as to not crimp the lace, dangle from my ankles. The twelve inch small chain that holds my ankles and the thin steel cuffs locked to it rests on the carpeted floor, the panties rest on top of it and cover the tops of my 3" spike heel pumps. My small but erect penis exposed in fro...

Black Femdom For Black Sissy

by Samuelx on Sep 11, 2017
Fetish

Sitting comfortably in her basement/dungeon, Ottawa's premier dominatrix Madame Whitley looked at her submissive, Shane Johnson, as the big and tall, formerly masculine Black dude stepped out. Clad in a pink Tutu, blonde wig, crimson pantyhose and high heels, the brother was finally letting out his inner slut. For years, Madame Whitley struggled to help Shan...

My Stepmother's Surprise

by sissybr on Sep 12, 2017
Transsexuals & Crossdressers

This is my first story, so I would appreciate some tips and comments. Please enjoy ^^ * My name is Robert, I'm 18, skinny and not too tall. I've never had much luck with girls, in fact I never dated one and I used to spent my days playing games on my computer and watching porn. Shemale porn. Dominant shemales fucking men. I wish i could be one of those men...