Dating Sim Stories

34,232 results
Orientation
Length
Source
Infinite Scroll

There All Along

by Unexpectedlyexpected on Oct 3, 2018
Romance

Logan was my best friend; we had been best friends since elementary school. I'm sure there were rumors about us dating, but we both had other relationships. We were just really great friends. He was good looking, tall, dark hair, dark blue eyes. The opposite of my short, brown eyed, strawberry blonde self. We parted ways in college, but we still kept in touc...

Professional Engagement Ch. 04

by Eclectic_Morsel on Nov 19, 2018
Romance

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** I walked swiftly back toward my house, Van's footsteps sounding behind me. I knew if I turned he'd be watching my long legs cover the ground. He'd probably be thinking about how we just did it in the forest, mere feet away from the gathered neighborhood. I know I was thinki...

Let Me Help You with That

by Eterriswolf on Oct 30, 2018
Exhibitionist & Voyeur

A/N: This piece is a work of fiction, the people in it are not real (well I am but the events and other people are not). Any similarities are coincidence, and should be dismissed. The first half of this story is based on real events, the walk and the pants, so have fun with that understanding. This story is about a Trans Woman, and I refuse to use the "tr...

Debut

by BataBitch on Mar 25, 2019
BDSM

My husband and I have been married for about five years. I am a 26-year-old Caterer, my husband is 32 and has a corporate job. To be honest I'm not entirely sure what he does. When he starts talking about statistics I tune out. We are happy, but lately we have been a little stale in bed. It is always the same, I'm on my back he climbs on top. After he slid...

Chastity with Ex as Keyholder Ch. 03

by chastity_sissy on Mar 12, 2019
Fetish

Back at my apartment, I wanted nothing more than to just get the chastity device off of me, but I still couldn't help but be aroused at my humiliating situation. Here I was, chastised by my previous girlfriend who now controlled not only my orgasms, but whether I could have sex with another woman. Suddenly, my phone buzzed, notifying me of a new text messa...

Do You Know Why I Pulled You Over?

by moreandmore on Mar 9, 2020
Loving Wives

My contribution to support the April Fools 2020 event. If you want to whine about me or any of my stories, be forewarned that I gave up caring about whiners for Lent. I have to tell you that it feels so good that I may adopt it as a new lifestyle. It only takes a few seconds to delete a rant, so please don't spend more time than that writing it. If you need...

Stuffed

by xerox2 on Mar 16, 2020
Fetish

Kelly went to Macy's, bought a silicon vulva the size of a t-bone steak, and shoved it into her pants. Despite having touched the material through the clamshell packaging's "feel me!" hole, the sudden touch of cold silicon against her shaved sex sent a shiver up her spine. She adjusted the prosthetic vulva, nestling the rubbery ridge on its backside between...

Bimbo Journey Ch. 01

by lacyamore on Mar 30, 2020
Erotic Couplings

Chapter One Leah woke up at 6, the same time she woke up every morning. She stretched her long legs and arched her back causing her B cup tits to strain against the fabric of her vest. She sat up and rubbed her eyes before getting to her feet and walking to the bathroom. She washed her face and stared at herself in the mirror. The usual thoughts came to min...

Unintended Consequences

by 10Bender on Mar 17, 2020
Erotic Couplings

Jay was a late bloomer. He never had a girlfriend in high school, nor in college. When he was twenty three he finally did get his cherry popped by an unremarkable girl, in a rushed and forgettable ten minutes. Except you never do forget your first time, no matter how regrettable, or mediocre it was. He ended up with his first girlfriend by the time he reache...

Hammock: Late-Night Swing for Two

by Ravenmiller on Mar 18, 2020
Romance

Alex and Bryce finished a long run and are now scarfing down burgers the same way they fuck—fast and hungrily. Bryce is a former college football player and Navy SEAL. His massive body shows every lean ounce of his hard-earned muscle. Everyone has always called him by his last name, even though his first name is Timothy. Despite weeks of dating and calling...