Boipussy Stories

101 results
Orientation
Length
Source
Infinite Scroll

Slut in the Basement

by KittyAshleyy on Apr 27, 2020
Transgender & Crossdressers

"Come on, Slut!" Daddy barked at me with a yank on the chain leash attached to my leather collar, causing me to stumble forward in my black high heels. I knew where he was leading me, the basement, Daddy had told me I was going to entertain some of his friends down there. I knew what that meant, which caused my boipussy to squeeze on the large silicone buttp...

A Sissy's New Daddy Ch. 05

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

When the loud speaker blared that Billie had a visitor he was tied to a stool. Billie had become a plaything for a few of the more business savvy residents of Blofield State Penitentiary. When prisons became smoke free buildings cigarettes were no longer the illicit currency of choice. Stamps had come into fashion because they couldn't keep you from mailing...

A Sissy's New Daddy Ch. 04

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

It was with great pleasure that I am finally able to upload chapter 4 of "A Sissy's New Daddy" I have spent the better part of a year working on this chapter. I was surprisingly hard to get down on paper. I want to thank all the readers that have taken a time to comment and rate the chapters of this story. It has meant a great deal to me and has at a few dar...

Cissy's Pegging Parlour

by Pinkmanties on Mar 18, 2020
Fetish

Fella's are you looking for a little backdoor action? Maybe you want those cheeks to feel the sting of a riding crop, or you want your boipussy filled with a firm supple dildo, or maybe you're just looking for a girl who will put your manclitty in a cage and tell you what a bad boy you've been! Come on down to Cissy's Pegging Parlour where your dreams become...

The King's Secret

by KittyAshleyy on Apr 22, 2020
Transgender & Crossdressers

King Mike was a great king, the people loved him, he had a beautiful queen, he ruled firmly but fairly and, at the age of 24, had a great reign ahead of him. He was tall and well built, keeping his lovely blonde hair short. He had blue eyes and a gentle smile. But he also had a secret. That secret was me, his concubine. He had picked me up off of the street...

A Sissy's New Daddy Ch. 02

by sissyneko on Oct 8, 2019
Transgender & Crossdressers

I hope you enjoy this second installment of 'A Sissy's New Daddy'. I worked hard on it and hope that it brings all of you the same pleasure reading it that it has brought me writing it. There are some extreme moments in this chapter but also some very tender ones. There was a line in the first piece that gets expanded on at the end. I hope you enjoy what I h...

Date Night with Daddy

by KittyAshleyy on Jul 15, 2020
Transgender & Crossdressers

As always after work, I entered mine and Daddy's empty house, quite exhausted from my day. Daddy always worked an hour later than I did, which on a normal day would give me time to redo my makeup, change into one of my skimpy maid outfits, and have dinner ready for when he returned. However when I entered our bedroom, I saw a tight black dress, a garter belt...

Birthday Wishes Ch. 03

by b_wishing on Sep 16, 2017
Transsexuals & Crossdressers

Everyone here is of legal age and they are having lots of fun. PART III "I am so glad you enjoyed me licking you earlier and how you enjoyed licking my pussy too. But now it is time for me to lick me some sissy asspussy. I have waited to do this for quite sometime now Kelly" she says as her hands massage my little backside. Soft kisses occasionally or a li...

A Sissy's New Daddy Ch. 06

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

A loud crack of thunder broke the silence and Billie smiled in his bunk. Lights had been out for almost an hour and he couldn't sleep. The prison had gotten a new influx of prisoners. The first night was always the hardest and it was hard on Billie too, he could never sleep listening to the crying. Plus Billie had gotten a new cellmate in the process, a cell...

A Sissy's New Daddy Ch. 07

by sissyneko on Oct 8, 2019
Transgender & Crossdressers

The interrogation room was cold and they hadn't given Billie anything to wear under the orange prison jumps suit. When Billie had been arrested he had only been wearing a bright blue satin teddy, but it was covered in blood so the police had been taken it as evidence. Now one had asked Billie anything, they stripped him photographed him and then shoved him i...