Shy Grandma Stories

54,743 results
Orientation
Length
Source
Infinite Scroll

New Moon Pt. 03

by GrimmsOtherBrother on Sep 11, 2017
Erotic Horror

Chapter 6: Everyone Loves A Tupperware Party! A week past uneventfully. I never saw Mrs. Bickers anytime I passed by her house. I think her husband came back home the day after our little ...er, experience...and so I assume she was otherwise employed and no longer needed my services. Thank goodness. I spent the week playing with my brother and bugging t...

Favorable Odds

by Fiend21 on Apr 11, 2017
Amateur

Watching your parents' SUV drive off down the road, you're left standing in front of the massive red brick building that serves as the Clear Water Institute's main center. You glance around, seeing a shining blue lake that you assume has given the campus its name, a large metal building you assume is a sports hall and two large dormitory buildings. You grima...

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Eating Out

by secret_admirer72116 on Sep 12, 2017
Mature

I guess the most frustrating thing about my getting older is that my dick doesn't work as well as it used to. I guess it started malfunctioning when I turned 60, I'm 67 now, but my wife didn't seem to mind all that much because my tongue still worked. My fingers still had magic in them. But about three years ago I lost my wife after a short battle with can...

Three Generations of Tits

by PositiveThinker on Sep 13, 2017
Novels and Novellas

I accompanied my girlfriend, Laura, to a family get together in California last September. Her two daughters Ellen and Christine and her Mom, Grandma Patricia, were the main reason for our visit. I didn't want to go. I hate family reunions. Moreover, I was hoping to use the opportunity of her absence to get together with some old friends and watch a game or...

Cougar House Ch. 23: Icy Hot

by SZENSEI on Dec 16, 2019
Exhibitionist & Voyeur

Cabot Ross had spent the last two days at his parents home. Family pulling together in trying times led to their placing his grandmother Edith into a nursing home. Unable to care for her properly, being very busy with their careers, they chose the easy way out. Cabot was not very happy about her new home feeling his folks just gave up on her. Taking the day...

Strawberry - A Shanghai Girl in America Ch. 04

by ChloeTzang on Sep 18, 2017
Interracial Love

Strawberry – A Shanghai Girl in America Ch. 04 Strawberry Under the Mistletoe – Part I – I'll Keep You Warm by Chloe Tzang © 2016 Chloe Tzang. All rights so reserved. This story or any portion thereof may not be reproduced or used in any manner whatsoever without the so express written permission of the author except for the use of so brief quotations i...

Time for Truth Ch. 02

by Iread2relax on Sep 18, 2017
NonHuman

Hello everyone. Welcome back to my exciting world of the Ivanovs and the Loess Pack. I tried to stay away, truly I did, but the story just wouldn't be quiet. So many unanswered questions, and who would ask the most. The children would. So here we go once again. It's time to learn the truth. This story is a continuation of the She Wolf Series. Please read...

Allyson Ch. 07

by carvohi on Sep 16, 2017
Romance

The two women helped each other down the stairs. Both had a lot on their minds. The younger woman, Allyson, was recovering from a vicious beating. She didn't actually need help, not in a physical sense, but her emotional situation was far different. At the moment she felt about as needy as she'd ever been in her entire life, and from the standpoint of a fo...

Anna

by JustLikeEwe on Aug 31, 2017
First Time

This story involves a young man who is a virgin, and a woman over three times his age. Therefore, this is both a "first time" story and a "mature" tale. * This wasn't the way that most guys my age want to spend the summer before heading off to college, I recall thinking as I looked out the kitchen window to the tiny yard and the postage stamp lawn that mig...

Edie's Journey Ch. 04

by penny_coyne on Sep 14, 2017
Transsexuals & Crossdressers

Part 4 -- Life with Grandpa The plane touched down uneventfully and being a domestic flight there was no customs inspection. I wheeled my luggage tote through the arrivals area seeking a taxi stand which I found in short order. My grandparents lived in the more rural part of the state and had been farmers. They sold off most of their land as their children...