Dating Grandma Stories

37,208 results
Orientation
Length
Source
Infinite Scroll

Worth the Wait

by hiddenthinker on Sep 12, 2017
Fetish

Mom had been single since I was born. No boyfriends that I can remember, no dad for me, since he left before I was around. It was just the two of us. I can't really say that, since she was always working with her "career" in advertising, leaving me with the baby sitter or the neighbor or whoever was to take care of me that day. But I knew that she would alwa...

A Proper Young Woman's Guide to Anal Etiquette Ch. 00

by lordodie on Sep 18, 2017
Anal

A Proper Young Woman's Guide to Anal Etiquette: Foreword Disclaimer: The following is a work of pure sexual fantasy and is intended for adult audiences ONLY. If you are under the age of 18, please stop reading NOW and go tell your parent and/or guardian that you need stricter internet supervision. Any physical resemblance to a real person that any fictiona...

Fallen Girls and Holidays Ch. 02

by SeesFourEver on Sep 16, 2017
Romance

Authors' note: This is my first attempt at a story. So feedback is certainly appreciated. It gets off to a rather slow start but hopefully will pick up a bit in later chapters. I have the first few chapters mostly done but I can't make any promises as to how quickly I'll be posting new ones after that. I can however promise that I'll finish it at some point...

Former Student

by Jason1974 on Sep 16, 2017
Interracial Love

Before graduating from college, I faced a common dilemma: What am I going to do with the rest of my life. I knew that I wanted to go to graduate school, but I also wanted to work for a few years. At the same time, I wasn't interested in entering the business world. After discussing my "dilemma" with my brother, he suggested that I move west and look for a t...

Internet Meeting Ch. 01

by johm55 on Sep 17, 2017
BDSM

After several weeks of email correspondence, we were finally to meet. I had arranged to pick her up at the local train station and she was to stay with me for the week-end. All being well, this would lead to her moving in as my 24/7 slave. We had arranged for recognition signals, just in case, and I had told her what to wear, a simple dress, shoes and no un...

Wanted: One Good Man Ch. 01

by Fantasealor on Sep 14, 2017
Toys & Masturbation

The ad read: Wanted, one good man with a kind heart. Preferably one who has a fondness for BBWs (Big Beautiful Women). No experience needed...will train. It was signed with a ‘wink’, along with her Canadian yahoo mailing address: Luvy On a hunch, he punched in her messenger name and left a brief note: Hi Luvy, just wanted to drop you a line. I love Canadian...

Restaurant Fun

by LoneEagle on Sep 12, 2017
Erotic Couplings

I had been dating my girlfriend for about three months, when we went to dinner at a restaurant near my home. We both knew she was going to spend the night, so it was no secret when she put a little overnight bag in the car. Her housemate would take care of her daughter overnight. Eve would certainly return the favor soon enough. Finding these little restaura...

The Demise of Snow White Ch. 1

by bunny-n-tiger on Sep 17, 2017
BDSM

Everyone knows the fairytale story of Snow White and the Seven Dwarfs. But this is not a story about Snow White the cartoon character, but rather, her real life equivalent. A dark haired beauty that was virginal, pure, kind and good that had yet to meet her prince. In fact, she was married to a toad for a very long time. In her search for that Prince, she li...

Damien

by sweet_slit on Sep 16, 2017
NonHuman

Lita arrived at her babysitting job on her usual Friday night. She never had a normal date, of course nothing in her life was ever very normal. She was being raised by her grandparent's, after her parent's were killed in an auto wreck when she was just three. Her grandparent's were strict, and because she was only 18, her dates had been a limited occasion, a...

Love Me Like You Do

by manchesterkate123 on Sep 14, 2017
Erotic Couplings

This is a very short story but I hope you enjoy it anyway. ***** When I saw you at my best friend's wedding, it was the first time I'd seen you in over seven years. We'd had a tempestuous on/off affair from the first year at Leeds University and continued to our mid-twenties. Despite the arguments and pain, you were and I guess still are, without doubt ,yo...