Dating Grandma Stories

37,208 results
Orientation
Length
Source
Infinite Scroll

Shady Oak

by Stringar on Sep 14, 2017
Mature

My thanks goes out to Kttn and Aleirian for taking the time out of their busy schedules to edit Shady Oak. ***** This year Jean and I celebrated our thirty-sixth wedding anniversary. I pause occasionally to glance at my wife, when she first crawls out of bed in the mornings with her white curls all tangled and snarled, or when she lays a loving hand on on...

Memoirs of a Variety Artiste Pt. 01

by giandomenico on May 28, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** My birth name was Daniel Terris. I have a cousin of exactly the same age called Jimmy Terris. Our fathers, after whom we were named, were brothers. They married two sisters, the Joyce sisters. Both families were, near enough, Variety royalty. My grandparents and great-grandparents...

A Black Lebanese Superstar

by Samuelx on Sep 14, 2017
Interracial Love

What am I going to do with myself? That's what I wondered as I sat inside the food court of the Saint Laurent Mall in the City of Ottawa, Ontario. Of all the sexy ladies of all hues walking by, why is it that only SHE arouses me? I don't frigging know. All I know is that what I'm feeling isn't normal. And I consider myself a pretty normal guy. My name is Art...

Three Ages of Woman Ch. 03

by istanbulnoir on Sep 13, 2017
Erotic Couplings

AN EROTIC PICARESQUE A couple of days later I was with Mum and we were getting down to it and her delicious dirty mouth was getting to work on my cock, when she suddenly stopped gobbling me off and got hold of my balls and pulled them and dug her nails in. Yeeouch...she was not just playing around...it fucking hurt! 'What are you doing that for?' I screame...

Dragons of Fraidel Ch. 04

by Zodia195 on Sep 13, 2017
Sci-Fi & Fantasy

A/N: Sooo sorry to my fans who've been waiting for almost a year for this next chapter. I've been super busy with college and now I have the summer off. I am thinking of dividing the chapters up just so I can update sooner. Just got to make sure I have enough words. I am already working on the next chapter and it's a pivotal one. I apologize for any grammati...

The Marital Bed

by Tx Tall Tales on Sep 13, 2017
Mature

======================= He loves her family, one of them, perhaps too much. Several years ago, I read Penasweapon's My Perverted Life, and it gave me an idea for a story, which I jotted down. It's taken quite a while to get it finished, my original notes are from 2010, so it's been percolating a while. The Alzheimer's and dementia described isn't wholly a...

Fucking 5 Black Women in a Month

by Bruson on Sep 12, 2017
Interracial Love

I'm 55, white and was looking for a woman 47-57 to have a relationship with. My latest LTR had ended about 6 months ago. Some women consider me good looking. Others think I'm average. I'm some kind of Rorshach Test for women. I'm blonde, or used to be before graying, blue eyes, slim from still working out 5 days a week and 5-11. And I eat healthy most of t...

Four Friends in a Parking Lot

by SilverCatEyes on Sep 1, 2017
Humor & Satire

After work one day Brandon, Chuck, Quinton, and myself were talking in the parking lot sharing stories of sex gone wrong. Everyone agrees that they should be shared and perhaps warp the readers as bad as it did them. But, since I wasn't there, I can't really stretch them into full blown stories. Just pass along what I "lucky" enough to hear. I swear to you e...

The Lost Camera

by thornapple on Sep 15, 2017
Romance

Philip Johnson Chapter One Her phone rang and when it's picked up I say, "Hi Jennie, it's Alex. "Alex, how are you?" "Almost as good as I'm likely to get. I called to see if you would like to spend the afternoon with me and since its July and hotter than hell, I thought we could rent a pontoon boat, have a picnic and maybe take a swim in the lake?" "...

Memoirs of a Variety Artiste Pt. 02

by giandomenico on Jun 5, 2019
Transgender & Crossdressers

When Franco and Roberto Guiglielmo called on us grandma, Janie and I were all in black. I am amazed that they didn't 'turn tail and hop it,' to use grandma's phrase. She had wanted us to change out of mourning but we thought it would be disrespectful to our husbands after less than three months. The two men had put on a certain amount of weight in the year...