Dating Grandma Stories

37,208 results
Orientation
Length
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Infinite Scroll

A Start Of Something Nice

by bobbymcgee on Sep 16, 2017
Group Sex

On the night of my high school graduation I met an amazing girl. We ended up dating for three and a half years before things just didn't work out. (Hey shit happens.) The time I went to pick her up for our first date, her dad answered the door and told me to wait in the living room. So I sat in the living room waiting for Cathy to get out of the shower. Eve...

Candy & Buddy's Romance Ch. 2

by sweet9tee on Sep 17, 2017
Mature

After Buddy and Candy enjoyed a cozy dinner together, they started talking about all sorts of things, including how fast Candy has grown up. Buddy mentioned how he noticed that Candy had been developing into a "mighty, fine lady" and that he would remember the times when she would come over on her bicycle to see Ann feed her pet lizard, years ago. Meanwhil...

Tarotica Ch. 02

by Anais on Sep 14, 2017
Loving Wives

The Magician The Magician is experiencing the establishment of his own identity through his own creativity and capabilities. . . .The Magician signifies originality and creativity. (Stewart Kaplan, Tarot Classic) You are able to master new situations, take positive action, and focus your attention to realize your potential. Making good use of available eq...

Fucking Sarah

by not_so_innocent_flirting on Sep 13, 2017
Erotic Couplings

"I like it when you do that," was all he needed to hear to send me over the top. Sex was Sarah's business and she was very good at it. I had been dating her for several months now and just sort of accepted her career as a high priced call girl simply because she was good to me and when we are together she makes me feel like I am the only man she wants to be...

First

by CassandraDreams on Aug 16, 2017
First Time

The seat is too soft. That is all I can think about as we ride to the hotel from the airport. It is Saturday and my parents think that I am with my friends' family enjoying a casual vacation in Florida. I should feel guilty but I don't. Adam is there smiling while he drives his beat up old car with its too soft leather seats. He is looking like the cat tha...

Discovering Allison Ch. 7 & 8

by story_time on Sep 14, 2017
Loving Wives

Chapter 7: Commitment Randi headed for work secure in the knowledge that things would be different on Monday. Having been the bearer of good news (as well as excellent blackmail material) Randi was now going to be rewarded by the new boss of Westman and Associates; Mrs. Westman. While John would still run the company, he would be doing so at the orders of...

A New Found Passion

by DarkrSide on Sep 14, 2017
Erotic Couplings

I'm not sure exactly how long Taryn and I have been sleeping together or what even started it all. We had known each other for a while, we were pretty good friends. Neither one of us was looking for a relationship. We were just out for fun, that's all. We were friends with benefits. Yes, we slept together but we were also real good friends. She always knew t...

He Sure Likes That Back!

by ElaborateHoax on Aug 31, 2017
Erotic Couplings

As a larger girl, you don't get many offers for sex, let alone many boyfriends. When a bigger girl can find a guy that will treat her right, she better make sure he can treat her right in bed as well... Destinee is 19 years old, she's about 5 feet 9inches tall. She weighs about 350lbs. Destinee is a big girl. Just because she's bigger does not mean that sh...

Small Town Dreams Ch. 01

by meganjoadams on Sep 14, 2017
Romance

Author's Note: All characters are over the age of 18. **BEEP BEEP BEEP** Mary Beth slaps the off button on her alarm clock and lies back on her bed. She thinks about what all she has to do today. She thinks "Yea...First football game of the season...so excited...not..." Mary Beth gets out of bed and goes through her morning ritual of getting ready for s...

The Architect Becomes Her Ch. 03

by Mistress_Joli on Sep 14, 2017
Mature

Again I want to thank my editors, MrWhiteTiger and autoplot, for their wonderful editing and help in making this a bit more interesting than it was before. Sorry T, for not putting in the part about Torture methods in Turkish prisons. I just didn't think it fit. For all my readers, thank you so much for your comments and the 'fun' chapter is next after this...