Sissy Prostate Stories

15,115 results
Orientation
Length
Source
Infinite Scroll

He Be Uncle Genesis

by justincbenedict on Sep 17, 2017
BDSM

Inside the Party Room, 19 year old Zoe bent down on one knee, dropping her chin to the floor and took the china plate in her teeth. Oh, it was disgusting to look at. A piece of pizza, four lipstick stained cigarette butts and an anchovy. Zoe began slowly pulling her chin up, feeling the intense pain from her knees on the floor of the Kappa Gamma Sade Party...

An Enlightened Evening

by HerLittlePiggy on Sep 13, 2017
Loving Wives

She was a big girl. Not fat per se but tall, thick and curvy with wide hips and big natural breasts. Her waist wasn't thin but it had a nice taper with a surprisingly flat stomach giving her a magnificent hour glass figure. Her legs, sprouting from a devilishly short dress, were strong and shapely with narrow, almost delicate ankles. She had long, shiny dar...

A Trickster's Life in Ottawa

by Samuelx on Sep 14, 2017
Erotic Couplings

"Reginald, if you don't have a thousand dollars for me by the end of this week, I'm evicting you, and I swear that I'm tossing your belongings outside," said my landlord, Mr. Jacobs, and I looked at the smug, bespectacled little old white dude, and flashed him a grin a shark would recognize. Must have had the desired effect for Mr. Jacobs flinched, and I all...

Finally, My Sister-In-Law, We Visit

by msm865 on Sep 14, 2017
Mature

To the literary purists – As with all my stories, I act in the role of narrator. This is a short story specifically designed to fit on one page. As such, there is no character development and no witty dialogue. I am not writing the next great novel. If another contributor would like to add names and dialogue and use this as an outline, go ahead. Improbable,...

Anal at Last

by Aussie_Ton on Sep 16, 2017
Anal

To the outside world Dave Blackwood looked like a conservative forty five year old accountant with a nice house two little kids a station wagon and a pretty wife. But to his wife Jackie he was the best sex she'd ever had. Jackie wasn't entirely surprised late one evening after the dishwasher was packed and the kids securely in bed when her husband asked her...

Sharing Sofia... Again

by SofiaMateo on Sep 25, 2017
Erotic Couplings

It had been a couple of months since Sofia and Mateo first acted out their fantasy. During intimate moments, Matt liked to whisper in Sofia's ear and remind her of the intense rush she got when two cocks were inside her. How totally filled and totally satisfied she felt. But he didn't need to remind her. Sofia thought about it all the time. And she hoped t...

Plus Expenses

by bencage on Sep 16, 2017
Anal

I'd broken the golden rule again. It was becoming a tiresome habit. Chandler's boy, Phillip Marlowe, may not be real, but he never broke it. He never did divorce work. The end of a romance is, frankly, the lowest human beings can get before they completely loose it. Even when it concerns basically good people; divorce can bring out the bad in anyone. That's...

Vegas: Interlude

by Marlene on Sep 16, 2017
Transsexuals & Crossdressers

I'm lucky in that I get to travel to Las Vegas for my work eight or ten times a year. I'm not a gambler but I love the city and the nightlife a lot. Particularly the people. As I've recounted in another story, my work requires that I dress as a guy but luckily I get done early enough in the day so that I have time for a full evening of dress-up fun and game...

Chris's Loft

by Marlene on Sep 16, 2017
Transsexuals & Crossdressers

My name's Marlene. I'm a transvestite. A crossdresser. My picture is on this site so you can see what I look like. I like both guys and girls although lately I've really been into cock more than "normal". I dress as much as I can but am limited by my work and that old enemy, time. There's this guy I know named Chris. He's a few years younger than my 34 and...

Stag Party

by donaldelliott11 on Sep 1, 2017
Group Sex

I'm supposed to get married on Saturday to the girl I've loved since High School. It is Wednesday right now as I write this -- 72 hours to go -- and I'm really worried that she'll find out about some of the wild shit that happened at my stag party last weekend. I barely remember most of it, but Jack, my best man, made a videotape of the whole party! He jus...