Dating Sim Stories

34,232 results
Orientation
Length
Source
Infinite Scroll

Why Did I Make That Call?

by Thompson99 on Aug 31, 2017
Fetish

This story contains very little sex. It is about a husband with a hang up opening up a Pandora's box of information about his wife's past. Move on to another story if that isn't for you. Jim had recently taken a new job in a new state. He enjoyed the job but missed his family, His wife, Marie, and kids hadn't yet made the move. They were waiting for the...

Doctor and Domina

by justincbenedict on Sep 13, 2017
BDSM

Eldred Plimsoll knelt before Luisa Earnshaw with trepidation. "So you thought you could take a little time off to play golf, did you, Eldie?" Luisa said, laughing heartily. Eldred was terrified, but he watched Luisa's breasts hungrily in her snug blue top. "Ma'am, I-I cleaned the house before I left. You wanted me to clean, and I did. All five bathrooms, an...

Stripper Night

by off2bed on Sep 14, 2017
Erotic Couplings

Surfing through TV channels, Carla paused on a show about male strippers. "Woo!" she said, surprising me. I didn't know she found that entertaining. Sure, we love watching hardcore porn together and she loved a good fuck as much as I do, but I thought her attitudes on stripping were a bit more conservative than mine. She told me once, "I don't mind if you w...

Pretty Peggy

by Teddy46 on Sep 13, 2017
Erotic Couplings

The night is dragging on toward morning and I've gotten no where, sitting here swilling gin and tonics till I'm about to fall off the barstool. And I'm not that fond of gin, but it seems to be the least offensive so I keep sucking them down. Now, my reason for sitting here is not to drink this swill, but to pick up a woman. Right, I simply want to get laid,...

I Didn't Know I Had It In Me

by sweetthing0864 on Sep 17, 2017
BDSM

After a bad relationship I had decided to take some time off from dating and sex. My self imposed celibacy had been going on two years. At first it had been really hard, I would wake up finding myself masturbating. But before long I was doing alright with it. I had inherited some money from an Uncle and could take my dream vacation. I had always wanted to g...

A Better Master

by WFEATHER on Sep 17, 2017
BDSM

How many times over the years had He made use of my ass, either with His own thick cock or with one of the anal toys in the collection? i could never begin to count, but i would guess that it would be over one hundred times during the first two years of marriage, plus perhaps another fifty times while dating and while engaged. Without question, He loved fi...

My English Whore

by DandyDom on Sep 19, 2017
BDSM

I met her online, not on a dating website or hook up site, just Twitter. Rather open as I am, one day I decided to make a tweet concerning my fetish, simply stating, "Are there any decent submissives out there?" I didn't think anyone took anything by it, in fact, it wasn't until a few weeks later did I get direct message about it. The message was incredibly...

Boundless Love Ch. 01

by trussedandobey on Sep 17, 2017
BDSM

A trigger warning. Although the acts in this story are consensual, there are mentions of rape, which could be disturbing to some readers. ***** Liddy traced her finger over her clitoris, closing her eyes as she sank into her pillows, breathing deeply. Memories of the past weekend, spent naked in a snowy cabin in Vermont alone with Patrick, flooded her mind...

My Angel on the Line

by dirtyjoe69 on Sep 16, 2017
Romance

I really don't care how anyone rates this story because it is the story of a time in my life when I fell in love to the most amazing women in the world. It is about meeting the woman I still have and will always want... * It was another lonely night; I was at the bottle again. My life was a tragedy most pathetic. I was 24 years old, already divorced and on...

One Memorable Night

by LoreLai on Sep 16, 2017
Romance

To Michael: You've changed me, for both good and bad. But no matter what the future holds, a piece of me will always love you for the way you made me feel that night. I'll never forget it. ***** I stood in his tiny bathroom, brushing my teeth before bed. We hadn't been dating long, but things were going well; we were enjoying each other's company quite a b...