Shy Grandma Stories

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Carl & Gladys

by atkins on Sep 14, 2017
Mature

I didn't like Carl when I met him. I liked him even less when I realized what he was up to. The place was an upscale bar in a big city. It doesn't really matter where. It could have been anywhere. It could have been in your hometown. You know the kind of bar I'm talking about. Lots of wood, a friendly but quiet bartender, maybe a little jazz trio on some...

Grandma's Butterfly Tattoo

by dlcalguy on Sep 18, 2017
First Time

Me and Davey were back together after our first year away at college. We'd been inseparable in high-school, but had gone to different universities and hadn't reconnected since he went away. I'd picked a school in our home town, so was still living at home. It was cheaper, but I wished I was getting more of the college experience by living away. Anyhow, we...

Shy Couple

by Magna12 on Sep 14, 2017
Loving Wives

Over the years, I've been fortunate enough to have had a vast amount of experience with married couples who want an added male to join them for some fun. It started long ago when I was quite the young man and by chance met a couple who invited me into their bedroom. Then I discovered ways to advertise and contact couples, and was, as I say, fortunate. Part...

Bribing the Babysitter

by Mister_Shy on Aug 21, 2018
Mature

Chapter 1 It had been two months since Jenni had first let Mr. Taylor masturbate on her. It was becoming a bad habit. Mr. Taylor didn't make a mess on her thighs every week. Jenni typically babysat for the Taylors on Tuesdays and Thursdays when no one would be home until late, and on the occasions that Mrs. Taylor drove her, the nights went by uneventfully...

Spunky Blackmail Ch. 04

by Mister_Shy on Sep 19, 2017
Erotic Couplings

I needed a date. My company was having a big end of the year bash at a downtown hotel and they were providing the rooms, the food, everything. All we needed to do was show up and have fun. There was business involved as well, some late afternoon seminars to attend, but the important thing, the major thing, was that I needed a date. Because afterwards, there...

Spunky Blackmail Ch. 02

by Mister_Shy on Sep 19, 2017
Anal

Tara and I were making love. It was a Thursday night and about a month since I'd cum all over her sister's face and tits. My blackmail had worked in a faithless and uninterrupted way and by the time Tara had returned from the grocery store Courtney and I had both cleaned up and pretended like nothing had happened (Courtney did spend the rest of the weekend g...

Grandma's Milk Maid

by Libertine on Sep 17, 2017
First Time

She came on a Sunday evening riding a bicycle. She rode all the way to the doorstep where I was sitting in the evening sun. "Hi there Buster. I am Lena. Grandma around?" She called before she even had dismounted. I knew that she was coming or, more correctly, that someone was supposed to. Grandma always tried to get what she called a vacation in the middle...

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...

Plumbing the Depths of Sex

by Egmont Grigor on Sep 13, 2017
Erotic Couplings

Shy and a little sly, Peggy-Sue Graham had taught similar age but a slightly late developer Pete Pitt everything he knew about the subject dominant at the centre of his mind - sex. The closest Pete had come to sex pre-Peggy-Sue had been the towel flicking fights he'd with the guys after coming out of the showers after football practice when the coaches wer...

Me and My Grandma

by EenViezeVent on Nov 6, 2017
Illustrated

Hello all! Welcome to yet another illustrated story. I was into the flow with the last one and decided to make a follow-up to that story. So here we have it, another short story with some rendered goodness! Again, each render in this story is made by the use of the free program DAZ 3D, all characters are again custom made by yours truly. As always, each ren...