Prostate Fisting Stories

13,270 results
Orientation
Length
Source
Infinite Scroll

A Sissy's Day of Fun

by sayaSky on Mar 10, 2020
Transgender & Crossdressers

Part 1 It was summer break, so I was visiting home after my first year of college. My parents were going to be gone for the next few days visiting old friends. Being by myself, I went online to a hookup app and searched for a match. In my ad, along with a picture of my ass in a thong, I said I'm a young male looking to get fucked by a top. It only took fift...

Cuckolding Sindy

by SindySuxALot on Sep 13, 2017
Transsexuals & Crossdressers

Domina Lucy Sissy Sindy sat in her room staring at her computer monitor. Her mistress Lucy had ordered her to stay in here and watch gay fisting videos. Her eyes watched the screen as closely as she could since she knew she might be tested on the content later. She was mildly distracted from the video by the huge vibrating plug inside of her sissy pussy. I...

MorningStar's Awakening

by MorningStar on Sep 13, 2017
Erotic Couplings

Somewhere along the line, I made a discovery about being a female and being able to be stimulated to such a peak that I experienced ejaculation. I've been encouraged to share my learning experience on here. Who knows, maybe in sharing what I've learned about how my own body reacts, more woman will realize they have the potential and just need to learn what t...

Beach Fuck of a Lifetime

by thonglovinpoolboy on Sep 14, 2017
Erotic Couplings

Here goes... I can hardly believe I'm telling you this, haven't ever told anyone before. I was at a nice secluded beach on Okracoke Island, NC on an intensely hot summer day. I was wearing a neon pink thong with a custom, extra large "torpedo" pouch to accommodate my rather well-endowed form. As I slid the "swimsuit" (really quite inappropriate for swimming...

Mistress and Pet Pt. 01

by jjtsd1981 on Jan 13, 2020
BDSM

Jacob wasn't sure exactly what he was doing, going to a dominatrix recommended by a friend. However, he trusted Dave, despite not having seen him for a while, and it had been a while since he'd had a good fuck. He showed up, wearing jeans and a t-shirt, not knowing what to expect but having had a couple shots for courage. He didn't really want to be dominate...

S is for Slut, Submission, Semen Ch. 03

by chanstevens on Sep 12, 2017
BDSM

Training my new fuck toy 'Slut Boy Craig' was a highly desireable way to end my Friday. Emma & I had just completed an aroused but frustrating 3 hour exercise session with Mr Butt and there was no doubt that we both needed some relief. Acting the filthy slut with Craig and teasing a few loads of watery spunk out of his 22 year old cock was just what we neede...

Marion's Turn Ch. 01

by jomar on Sep 13, 2017
Fetish

I stood in the foyer. She was gorgeous. Hair up, dressed in black; corset, stockings, panties, high heels. And a strap-on. "You really gave it to me good last month, baby. I didn't expect those other guys. At first I was a teensy bit mad...but I gave into it and I couldn't get enough cock, could I, baby. Mmm, those cocks in all my holes, all slippery with...

Mistress Pt. 02: Being the Bitch

by WednesdaysCoffin on Nov 18, 2019
BDSM

Author's Note: This short story contains some BDSM elements, including femdom and a strap-on. All characters are well beyond the age of 18, and none were harmed in the writing of this piece. The title is admittedly dumb, yes. ©WednesdaysCoffin 2019. This story cannot be transferred to any other site besides Literotica.com without prior authorization in writi...

Vegas: The Dirty Dozen Ch. 06

by Benny024 on Aug 31, 2017
Group Sex

I was standing in the in one of the small, dark theater rooms watching a movie. A white woman was sitting on a black man. He was pumping his large cock into her fat pussy while she sucked a large white cock. A third man had moved up behind the woman to put his cock into her dilated asshole, when I noticed a petite, young, white woman slowly enter the theater...

A Strapon Tale Pt. 02

by damn_thats_me on Mar 2, 2020
Fetish

All the events in this story really happened, only the names have been changed. Warning: contains themes of pegging, femdom, leather & latex, chastity play, and mild cuckolding. *** As mentioned in our last story Alex (29) and I (36) are both switches, and enjoy taking turns dominating each other. We had been dating for about a year now. Yet while we met...