Grandma Sex Stories

225,571 results
Orientation
Length
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Infinite Scroll

Never Let Grandma Buy Gifts

by DragonCobolt on Dec 12, 2018
Sci-Fi & Fantasy

If I could blame anyone for this nightmare of a holiday, it would be Jennifer Hale and my grandma. Now, you may wonder why an acclaimed voice actress would take time out of her Christmas schedule to ensure that my holiday was spent getting thoroughly fucked. Well, that's just the thing. She didn't. For those of you who have never played the seminal classic...

A Most Graceful Life Ch. 09

by CJMcCormick on Jul 9, 2019
Sci-Fi & Fantasy

"Can you tell me how he is? Will he be alright?" Stephen was driving a bit too quickly down the road, with Grace in the passenger seat. Shortly after receiving his mother's call, they fully dressed and were out the door, making the short trip out to the hospital. "He's.. in a lot of pain," said Grace, slowly, with a fearful expression on her face. "Is he...

Red Riding Hood, Revisited Ch. 01

by djehuty on Sep 16, 2017
Sci-Fi & Fantasy

Note: I've never liked the subtext of the Red Riding Hood story. Here's a rewrite with a better message. * In the middle of the dark wood there goes a girl in a red cape, not lost but tasting of her first disobedience, and the fruit - a peach she's taken from the basket at her side - will never now see Grandma's, though its juice goes the happier path down...

You Gave Me a Mountain Ch. 01

by DG Hear on Sep 14, 2017
Non-Erotic

Thank you to my editors LadyCibelle and Techsan for making this story a much better read. * I was sitting there in the restaurant in the quaint small town where I used to live. They had one of those tabletop jukeboxes and I was looking through the song titles. I remembered how so many songs seemed to be a pathway for me. I slipped in a few coins and pushed...

Doggy-Style in the Pussy Cat

by Lascivo on Sep 12, 2017
Erotic Couplings

Doggy-Style in the Pussy Cat (or Lick, Pussy! Lick! Lick!) No one ever believes my story. But, hey! Who cares? I'm content to enjoy the memory myself. 'Twas my third year in Phi Beta Kappa, the days when Big Daddy ruled the House. Big Daddy? He really doesn't need any description. It's suffice to say that he lived to perfect the fraternity stereotype. H...

I've Got the Trains to Keep Me Company

by The_Technician on Oct 14, 2017
Toys & Masturbation

A lonely young woman is left the family farmhouse by her grandmother who always said, "I've got the trains to keep me company." This is a VERY mild story that will primarily appeal to those who are into machine self-stimulation or have a fetish about steampunk. There is no explicit sex. Instead this sets up a fantasy which some will live out in their own mi...

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...

Redo Ch. 06

by cassandraharper on Nov 21, 2017
Interracial Love

I want to apologize for the long wait. I'm going through a transitional period right now and also had a bit of writer's block. I know that some of you have asked for longer chapters, but they won't be long. three to four pages on Literotica is actually about 11-12 in Word. All the same, enjoy the new chapter and I'm looking forward to your constructive criti...

The Shy Girl

by deepemerald on Aug 30, 2017
First Time

Jessie Stephenson was a shy high school senior. All through high school she'd wished she was more like the outgoing cheerleaders or the captains of the debate teams or anyone other than herself. She spent the day trying to disappear into the shadows at school and was incredibly relieved when the final bell went so that she could get into her car and drive ho...

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,...