Asspussy Stories

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Orientation
Length
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Infinite Scroll

Jenny and the Wedding Dress

by Gemsissy on Sep 13, 2017
Fetish

I parked my car on the side street as I'd done a dozen times now. I was very excited and my cock was hard in my sissy panties as I got out of the car. Grabbing my gym bag, I felt the weight of the breast forms I carried in it, excited to put them on soon. I'd waited several weeks since my last visit to save up a nice amount of mad money. I never got out of a...

She Dad Ch. 02

by FirstTimer69 on Sep 15, 2017
Transsexuals & Crossdressers

Read part 1 to get caught up. * Following the life changing events of Friday night where 'Darla' had given 'her' virginity to her virgin teenage son, Jack, sucking his cock and allowing him to fucker her ass twice... there had followed a dramatically uneventful weekend. Darla had prepared a new outfit consisting of a catholic school girl's uniform, red...

Terri Lynn and the Train

by Marlene on Aug 30, 2017
Group Sex

My name's Mark. You might have read about me in a few stories that have appeared on here written by my friend Marlene (Dirty transvestite bitch! God she's fucking hot!) I'm what I call an effectual bi-sexual. In other words I'll do most anything sexual other than scat (I guess there're folks that like that but I'm sure not one of them.) And am constantly on...

Uncovering the Sissy Beneath Pt. 07

by jefferyscott745 on Aug 6, 2019
Transgender & Crossdressers

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional. This is part seven of my previous work. Be sure to read parts 1-6 if you wish to understand the background of this section. Three days had gone by, since Sherry and I had our intimate session together. We had practiced multiple times after t...

Craigslist Adventures 05

by PorscheKaru on Jun 9, 2020
Transgender & Crossdressers

I arrive at my new place and lug the gurly things suitcase inside and into the bathroom. Daddy messaged me that he's about 30 minutes away, he had to take a business call. He mentions in the message he would really love to see me in full passable makeup when he comes over, he's so horny and can't wait for me to finish him off. I guess I do owe him big for h...

AliExpress and Sissy Downfall Pt. 08

by His_fag_wife on Jul 10, 2018
Transsexuals & Crossdressers

Emma's gaze swung around the room taking in as much of the contents of the room as she could. So many of the items being completely unrecognizable to her. "Close your mouth my dear little slut or I may have to put something in it." "Yes Master, sorry Master, it is just an amazing collection." "It is, isn't it and we'll get Charlie to choose your new plug...

Craigslist Adventures 04

by PorscheKaru on May 13, 2020
Transgender & Crossdressers

Before I tell more of my stories from the past I'm going to update you on what's going on with me most recently. The girlfriend I have been living with has left me and moved to another state. So despite the hurt I figured the best thing to do was to order gurly stuff and start dressing again. But before that, while still together with my girlfriend, she...

O Holy Night

by puzziboi on Dec 23, 2019
Transgender & Crossdressers

Mike Dyer knew full well that his employer was one of the most transgender friendly college campuses around - especially in the South. The hardy, rangy, shiny-headed facilities supervisor had attended more than one training regarding LGBTQ+ issues. He knew not to assume pronouns when meeting people. The thirty-seven year old native Carolinian had no issue wi...

Aficionado Gets in Trouble Ch. 04

by His_fag_wife on Mar 17, 2020
Transgender & Crossdressers

Taryn told me to sit down, which I did with difficulty as I was only just getting used to breathing with the corset on. She knelt down in front of me, but this time it had no hint of submission. She was plainly completely in charge of me at this moment. She took the first shoe off, and prepared the first stocking, rolling it over her thumbs. I put my foot o...

Covid 19 - Pete Turned into Charleigh Pt. 03

by His_fag_wife on Jul 13, 2020
Transgender & Crossdressers

"OK off with the wig now and we'll get rid of body hair first and then we can document the necessary changes." Mistress Red pulled off Charleigh's wig, one of the last vestiges of Charleigh's feminine sissy armor and as Pete looked in the mirror, he wondered if he was doing the right thing. With his bald head, flabby pecs and miniscule caged cock, he certa...