Sissy Prostate Stories

15,115 results
Orientation
Length
Source
Infinite Scroll

Locked Up Ch. 03: Maid Maria

by Prof_Owen910 on Apr 14, 2020
BDSM

"Ohh fuck, Gwen, yes, fuck my boicunt, stuff your fat cock up my ass!" Words I never ever would have guessed I would say spilled out of my mouth before I buried my head in my pillow and cried out, my aching balls spasming as my fiancé fucked me to yet another massive anal orgasm. A month of straight anal play with no other stimulation had turned me into a...

My Name is Raquel Ch. 10

by Raquels_Panties on Apr 13, 2020
Transgender & Crossdressers

My name is Raquel and I'm a crossdresser. As my profile indicates, I have been a passive reader of Literotica for at least 15 years. During that time, and even before then, I wrote and rewrote Raquel's stories over end over in my head. If this is your first encounter with Raquel, I encourage you to go back and start at the beginning to understand her stor...

My Last Night of Freedom Ch. 03

by Sungmehetu on May 4, 2020
BDSM

Lindy The cussing from the basement was loud enough to reach the kitchen. Domina was upstairs, recently fed, and I spent an hour at church. Johanna came down stairs after her turn at church and relieving Domina's bladder. Two plates were on the floor with eggs and sausage on them. "Honey I need you. She filled me up." Johanna said. So I lay on the floor a...

The Training of Jeff Stintum Ch. 17

by JoyceJulep on Jun 8, 2020
Fetish

Chapter 17: Sarah Finds the Spot 236.7. Jeff just looked blankly at the number for a few moments. He didn't even register Sarah wiggling the toes on her bare feet in excitement. Her body was vibrating with golden energy as she looked down on him from the scale, his eyes now once again even with the top of her abs because of the scale's extra few inches....

Billy Babb's Bargain

by Nellskitchen on Jun 9, 2020
Fetish

"So, this is for real?" His skeptical and struggling voice is low, gravelly—his vocal cords, inflamed. His nervous chuckle meant to highlight male confidence; instead, conveys agitation. As intended, his initial sure-footedness dropped with his jeans, which, piled loosely about his ankles, makes him appear what he is—alone, foolish. I neglect to answer...

Barely Legal Ch. 06

by AntonioSanova on Jun 9, 2020
First Time

I woke up from my nap only to be met by my little Asian wildcat offering me one of the sandwiches I bought earlier that morning. She'd found the plates, individual bags of chips in the pantry, and everything I'd stored in the fridge. She'd already placed the coke on my bedside table and was gently sitting on my side of the bed. Yes, she was still in her cute...

Estrogenie Pt. 01

by Eterriswolf on Jul 15, 2020
Humor & Satire

A/N: If you're not familiar with me, it is important to know I'm almost completely blind. This series is a first-person fantasy and not all the wishes will be written about in detail. If you're reading mostly for sex, read the intro, then skip the first 9 wishes and finish the bottom from wishes 10-12. I am the main character of this story and my descriptio...

My New Life in Lingerie

by Everyday2 on Jul 14, 2020
Transgender & Crossdressers

It started innocently enough. There was that time many years ago when I saw a pair of my wife's panties in the laundry hamper. I couldn't help myself and decided to try them on. They were amazing! The way they hugged my ass and balls is impossible to describe. I left them on most of the day as my wife was gone to work. Walking in the panties made me hard, an...

The Institute - Thomas Dean Pt. 01

by thomas_dean on Oct 19, 2020
Fetish

"Good morning, Dr Throop." I introduced 6 foot Mr Castleton to the Institutes' Staff Physician, a bespeckled 40 year old svelte 5' 3" doctor with white lab coat over a sky blue blouse and dark skirt, "Let me introduce Mr James Castleton a visitor who is going to take a tour of the Facility. He is thinking of indenturing a daughter here." Hmm, I thought to m...

An Alien Love Bk. 02 Ch. 06

by Read_Moore on Oct 6, 2020
Anal

This week I was so proud of myself! I worked on One Strong Gale (My next Ice Era Chronicle) and I worked on Joe's book which is my next release... however all that hard work and I didn't get to play with this story. But now that I'm all caught up on that stuff, I wrote a few chapters for Octnavin and Sloan. FUN!! So here we go again... If you are new here,...