Dating Sim Stories

34,232 results
Orientation
Length
Source
Infinite Scroll

Haitian MILF Reigns Supreme

by Samuelx on Dec 18, 2018
Erotic Couplings

"You know, Steve, you're always complaining about your girlfriend," Marianne Etienne says, looking at Stevenson Vladimir. Upon hearing those words, Steve paused. The tall, dark-skinned, chubby but handsome Haitian security guard sighed. Truth be told, Stevenson had been telling Marianne stories for these past few months. Nevertheless, the lie-prone security...

Magic Dress - Angela Pt. 05

by SlightlyRude on Feb 25, 2019
Transgender & Crossdressers

I was approached by the Union Reps again. "It was a great party, boss. Shame you weren't there. But on behalf of our members, we sincerely hope it is going to be an annual event, or we may down tools." With the emphasis on 'tools', of course. Susan told me that the women had greatly appreciated our efforts to get their husbands going, and no-one was offende...

The Birthday Suit Club - Mrs. Layton's Story

by Jamie753 on Jan 8, 2019
Exhibitionist & Voyeur

All characters are eighteen or older. *** If you've read any of the other "The Birthday Suit Club" series you know how this all started. If not, then here is a brief recap. I was severely burned, including my face, as a child which lead to me becoming very reclusive as a teenager. My sister, Gail, decided that I needed to have more social contacts so she m...

I Called Her Bluff

by gymratt24 on Sep 25, 2019
Erotic Couplings

My first time to ever tell this story. This is absolutely true, from start to finish. Hope you enjoy, I know I did! ***** Tina was always a lady that I would catch myself staring at. There were a couple of occasions that I would catch her staring back, but I didn't think much of it. I was in college, single, and she was married in her early 30's. I am th...

Wanda as Seen from the Audience

by Pugzilla on Sep 24, 2019
Exhibitionist & Voyeur

Wanda At The Beach told from the perspective of an audience member. I decided to write something for the fans of my exposure fetish fans so they don't abandon me while I write more relationship-driven stuff. When I heard about the event I thought it was too good to be true. I had always had kind of a crush on Wanda. She was pretty easy to crush on. She was...

Jim and Cheryl Ch. 05

by Willupboss on Sep 23, 2019
Loving Wives

Epilog NOTE FROM AUTHOR: This is the final chapter and as such is much shorter than previous chapters. Here we wrap up some final thoughts with our characters. I'm not a legal expert but I did do some research into such cases. I realize that the dollar totals seem totally unrealistic but in fact these type of totals are not without precedence. Especially wh...

Long Expected Day Ch. 01

by jcthatcher4 on Sep 24, 2019
Loving Wives

This is my first story and part of a much longer story I have been working on so I would definitely enjoy the encouragement if you like it. The wedding reception was fun, but rushed. The hotel was just a short drive from the church where the wedding and reception took place. When Tim and Kelsey got there, they checked into the suite that her parents had...

Ally's New Boss

by Tink2019 on Dec 2, 2019
First Time

As Ally walked into his office, she was both excited and nervous. The people in HR had warned her about her new boss. That he was very strict, liked things a certain way, and was very demanding. She hoped to catch on quickly. She walked in with his coffee, black is what she had been told. He muttered under his breath and sighed. He had been gone for two wee...

The Bull, the Bitch, and the Cupboard

by BadBanana2 on Oct 16, 2018
Fetish

Bill is the gym jock and he's sitting butt naked in my front room, ass cheek to sofa, with his hand wrapped around that semi hard monster cock. Nine inches in length and he hasn't even started yet. He has that smug grin on his face, the kind he has after he gives me a shiner. A bitter beer in his hand that the stud has helped himself to too. He's pure tras...

The Red Contestant

by bawdybloke on Nov 5, 2018
Group Sex

She could have said we needed the money, but we didn't. My inheritance was sizeable, my wage was good and our house was one of the largest in our town. We lived comfortably, without any debts and well enough to allow my trophy wife to engage in all manner of leisurely pursuits. She did tennis on Mondays, badminton on Tuesdays, gym on Wednesdays and Saturda...