Dating Sim Stories

34,232 results
Orientation
Length
Source
Infinite Scroll

Richard's Bay Pt. 01

by DarkSouls on Jul 3, 2018
Erotic Couplings

The rickety van bounced along the dirt roads toward Richard's Bay driving through rain and thunder to deliver its sole passenger, a young lady, to the Grand Hotel of the Bay. A wall of rectangular lights pierced the stormy night as the enormous structure came into view through the haze of rain. The van pulled close and the driver collected his payment before...

All Tied Up

by The_Dongs_Johnson on Jan 1, 2019
BDSM

Part I After a year and a half of dating, Alex knew Sam pretty well, what she liked and disliked, what scared her, and what got her going. And what he knew about her more than anything else - she loved it rough. He found this out on a whirlwind of a night. It had been the second time they had been intimate. The first was at some house party after drinking t...

Happy New Year with Slutty Sue

by raidernation25 on Sep 25, 2018
Group Sex

I'm a big fan of the holidays because my slutty sister-in-law tends to fly in for a visit and always tells me a new story about the sexual escapades of my wife Sue. Well she was over for a summer visit, and one night the three of us were sitting in the hot tub drinking whenever Kim asked Sue a question. "Have you ever told Ed about New Years Eve at Dave's...

Wife's Night as Play Toy

by whynottrynewthings on May 20, 2019
BDSM

When my wife first told me she was interested in BDSM, I didn't know how to react. I didn't know much about it but I knew I didn't want to hurt her. After some conversations and research, we started trying things weekly. To my surprise, I'm enjoying it. I've learned that even when I'm "hurting" her, I'm not actually hurting her. I'm giving her enjoyment. She...

Online Meet Up

by nastynasto on May 15, 2019
Exhibitionist & Voyeur

I've been on a million dates with friends, strangers, blind dates, set ups, meet ups, online, etc. You name it, I've tried. I like the anonymity of it all. I don't want to be viewed as a slut or loose or whatever. I'm struggling with my empowered bad bitch beyonce side because I should be allowed to feel sex positive and independent to do what I want and who...

That First Time

by Javahead on Jun 18, 2019
First Time

I remember the first time we made love very clearly. It was winter, and the house was - not cold - cool. It was late, and everyone else had gone to bed, but the two of us were still up, bundled under a blanket, and talking quietly between kisses. We had been dating for several months at that point, but we were still a little afraid, I think, to decide ho...

Wanda Back at School Pt. 04

by Pugzilla on Jun 18, 2019
Exhibitionist & Voyeur

As the day draws on, Wanda prepares to attend a class with Julie and several of the key participants of her epic reveal in front of the whole school. Wanda had not been able to find Julie since before school started. The day had been a rollercoaster. It started with everyone openly ogling and mocking her after her total exposure over spring break. She made...

Black Male Bisexuality

by Samuelx on Jan 8, 2019
Group Sex

Meet Jarrod Willer, a big and tall young Black man living in the City of Ottawa, Ontario. He recently moved there from the South Side of Chicago, Illinois, where there are shootings every weekend. Jarrod is studying Criminology at Carleton University and slowly adjusting to his new digs in the Canadian Capital. The brother desperately missed his hometown of...

My First Big Cock

by Wifeluvscock95 on Dec 12, 2018
Loving Wives

"The sheer girth of his cock completely filled my soaking pussy and went in with relative ease". This was the moment that I had taken my first cock that wasn't my husbands since we said "I do". Let me give you the backstory that led up to this glorious moment. My husband and I have been married for 23 years. He's 53 and I'm 51. We look ten years younger an...

Heather's Revenge

by alphawaves on Jan 14, 2019
Fetish

Heather and Ryan Starwood were twin siblings. Heather was a gorgeous brunette with long soft legs, a nice ass and big double D breasts. She was smart, funny and had a great personality. Ryan was also highly attractive. He had a nice square chin, large muscles and a firm ass. In fact, most girls would agree he is one of the hottest guys in town. However, unl...