Great Grandma Stories

192,140 results
Orientation
Length
Source
Infinite Scroll

Sundae by the Sea

by atkins on Sep 13, 2017
Mature

It was warm as it often is in late September along the Florida Gulf Coat, but not hot. And at 2 p.m., just like clockwork, she was going about her ritual. It didn't seem to matter whether it was hot, warm or threatening rain, she always did the same thing. And Colin, as usual, was watching her closely. Here was this old woman (Colin figured she was 70 if a...

Further Training as Sissy Lesbian

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one. Enjoy and please take time to give me some feedback! Theo 3. Intermission: Further training Following the loss of my sissy virginity just after I had turned eighteen years old,...

Decades Ch. 01

by YDB95 on Sep 16, 2017
Novels and Novellas

Doug had a photograph of Grandma and Aunt Doro on the beach, which he had kept on his desk throughout his four years at Columbia. Snapshots of various buddies and girlfriends had come and gone, and for appearance's sake he had occasionally also displayed a picture of his mother when he could stand to; but Grandma and Aunt Doro were there with him throughout...

18-year-old Designed for SIN!

by showguy on Sep 25, 2017
Group Sex

If you enjoy this story please revisit my last two submissions: Naughty High Class Mom parts 1&2. Thank You, hotteeat60. I would like to express my thanks to istanbulnoir for helping edit this feature. Background In The White Trash Trailer Park: The following story is an account of the wild experiences that a friend of mine had fucking my trailer par...

It's Not Easy to Be a Love Goddess Ch. 09

by Cheleste on Sep 16, 2017
Novels and Novellas

Angela got her veterinary degree and went into practice, and I made sure to refer every pet owner I came across to her. My devotees were only too happy to take their dogs and cats to her office. And after two years of successful practice, we were overjoyed to learn that Angela and Sam were to be parents. I liked Sam. He reminded me a little of Barry—so sma...

Life's Changes Ch. 03

by EmeraldKitten on Sep 17, 2017
Non-Erotic

I'd like to thank anyone who's read my 'series'... this last three non-erotic pieces are the baring of my soul. When this particular one was originally posted, it got a few negative comments about the way it was written. I tried to do it a different way, but this is how it wanted to come out. I appreciate the time you've taken to read these submissions....

Red's Riding Hood

by SciFurz on Sep 19, 2017
NonHuman

*The familiar story, but with a twist that came suddenly to me a while ago and I couldn't resist writing it. *Literotica rules apply, which means everyone is an adult. Grandma especially so. * Chapter 01 Red woke up from a deep sleep, sat up in her soft bed, her long blond hair draped haphazardly around her shoulders, blinked her sticky eyelids slowly, y...

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...

Nina's Night Visitor Ch. 02

by SexyNina071989 on Oct 12, 2020
Romance

This story is pure fiction. This story Is for adults only. Do not read this story if under eighteen years of age, or live somewhere where adult material is illegal. All Characters are eighteen years of age or older. ***** Nina's body continued to tremble post-orgasm. The juice of her sex still dripped, Her cunt still agape. She had mixed emotions. Nina...

Mistress Myriam of Buttermilk Falls

by justincbenedict on Sep 15, 2017
BDSM

Chauncey Nodalsky looked desperately at Myriam's breasts, poking as they were, nearly falling out of her little corset. "Okay, Grandma...I'll think about it. Yeah, I love Uncle Gideon, but Buttermilk Falls is a little too boondocky for me, like, no offense. Love you, bye." Myriam stroked Chauncey's cock as he knelt naked on the bed, his hands tied snugly to...