Date Night Stories

254,424 results
Orientation
Length
Source
Infinite Scroll

Affairs

by R. Richard on Sep 11, 2017
Letters & Transcripts

Date: Sun, 15 Feb 2004 12:11:09 -0500 From: TallDarkStud Subject: LastNight To: AngelOfTheMorning Last night was the most fantastic experience I have ever had. Our chance meeting at the Valentine’s Day dance was incredible luck! I could tell that you were a little uncomfortable with the rather revealing dress you wore. However, even with your initial shynes...

Man at The Bar

by MissFaith on Sep 17, 2017
BDSM

It was a warm evening. One of those that carry the slight hint of autumn in the air but the promised coolness hasn't arrived yet. The sun was softly sitting on the horizon as people bustled past as I sat on the bench and awaited my date for the night. We had met a few times and I was beginning to get comfortable with him. I had chosen to be brought by my car...

Metamorphosis Ch. 02

by FrederickJones on Sep 17, 2017
Loving Wives

Tina enjoyed telling me about it. "She's been having all kinds of fun. I guess it's rebounding after a divorce or something. When she talks about romantic dinners out with strangers, then bringing them back to her place, well, it sounds so exciting and sexy. Maybe I'm jealous. She sure seems to be having a lot of fun these days." I offered my opinion. "She...

Holly and (What's Left of) the City Pt. 04

by neolim on Jun 9, 2020
Fetish

"Where are we going?" Maria curiously asked. They've been walking for the better part of an hour, but the cool night air made it totally manageable. Every now and then a cool and cheerful breeze would rush past the two women and play with their hair. It wasn't too cold or too hot, the weather was just perfect. Maria toyed with the thought the futa might eve...

Kate's Date

by saddletramp1956 on Aug 24, 2020
Loving Wives

Kate's Date Many thanks to those who offered comments and constructive criticism on my previous stories. For those who want to say this or that would never happen, remember this is my universe, a place where nearly anything can, and often does, happen. At least on paper... Please refer to my profile for more on my personal policy regarding comments,...

Amanda Guesses Wrong

by Just Plain Bob on Mar 27, 2019
Loving Wives

I looked at her like she was some alien life form as my mind digested what she'd said to me over dinner. She had waited until the fresh baked apple pie was cut and then she had hit me with it. "There is no easy way for me to do this so I'll go right at it. The kids are gone. I've been a damned good wife, mother and homemaker for the last twenty-four years....

Chaperone

by SIGSEGV on Sep 11, 2018
Fetish

Samantha nibbled on a French fry. She turned her eyes toward her date and blushed when she saw how him watching her. She smiled. "What is it?" she asked. "Oh, nothing," the boy replied dreamily. Samantha couldn't help but giggle. It was late at night and they were both sitting in a booth at a retrofitted 50's style McDonald's. There was a tray of cheap fo...

From a Husband to a Dutiful Sissy Ch. 12

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Twelve: New Days, New Times, New Possibilities. As in life the Sun still rises and sets, days will pass by, tears will dry, life will go on...Over the last few days, I have kept myself busy as I can to keep my mind off of Jack. It is hard not to think of him to sense him and to want to be held by him. He was my first love now that I live as a trans...

The Clean Up Girl, Ally

by Zandslut on Sep 26, 2017
Exhibitionist & Voyeur

My wife is pretty well known to the guys in our town. It must run in the family. When they were younger, my wife and her sister, Ally, were very trying to fit in at a new school, where they had moved in high school. As there were very few Asian people at their new school, they were seen as a mix of exotic and outsider. Bec found her way to popularity, throu...

Is Love All or Nothing? Ch. 02

by DestinyReader on Sep 18, 2017
Romance

Thank you again Tigersman for editing this chapter and covering up all my mistakes. For newcomers to this story welcome and I hope you enjoy. * Keith wakes up just before noon, but was hoping he could just stay asleep and not have to deal with the day or his best friend. He didn't want to get out of bed but knew this was something he could not avoid. Andy...