Helping Grandma Stories

62,858 results
Orientation
Length
Source
Infinite Scroll

Prone

by hobbleddream on Jul 4, 2018
BDSM

We had been playing "text sex" all day while Id been out shopping and about an hour had gone by since the last message: "when you come in you will go upstairs, get naked, put the red leather cuffs on both wrists and both ankles, put in some ear plugs and put on the leather hood" I was almost running home at this, but still had to go and finish some shoppin...

Gullible Danielle

by Nudiebooty24 on Jul 31, 2018
Exhibitionist & Voyeur

Danielle was a quiet girl. She was very shy, although you might not know it from her reputation. Danielle was also not very bright. She did ok in her classes, however she could be quite ditzy sometimes. And she was very gullible. She often ended up on the receiving end of many "pranks". However, one day in particular Danielle was at Katie's house for a pool...

Naughty School Girl

by Lovelaw on Mar 6, 2018
First Time

As I sit in my office, I can see you bending over to put away a file in the bottom drawer of the file cabinet. You have always been a sweet girl, helping out in the school office, running errands for me. The last few months though, I've noticed you more; lingering around my door, watching me when you think I'm not looking. Even now, as your hair hangs down i...

Camp Out

by ScentualEncounters on Mar 6, 2018
First Time

I woke up this morning in our tent in the woods, the faint clinking of camping cookware being arranged over a crackling fire, the sun barely visible through the treetops on its approach. Forest sounds so comforting, campfire smoke wafting through the screened "windows"... I smile, remembering where I am, pulling your pillow close to hug and inhaling your sce...

A Fateful Trip Pt. 02

by TTM86 on Mar 13, 2018
Transsexuals & Crossdressers

My wife was waiting for me to pick her up and I was stuck wearing pink heels. I could run home quickly to pick up regular shoes, but our house was a 'smart' house with alarm. If I opened the garage door, front or back doors a notification would hit her phone, which would require a lot of explanation. Even if I managed to find a way inside the house, I would...

The Touch of a Stranger

by Secret_Passion2018 on Mar 21, 2018
Group Sex

Jo and Nick had been playing for a few months when he finally arranged for one of her fantasies to be fulfilled. Since they had chatted Nick had teased her with the idea of a threesome with one of her friends. At first she had been interested but the more she got to know him the more interested she was. She was tall, a few inches shy of six foot, and had go...

Mankind Survives Nuclear War

by tsar7 on Nov 21, 2017
Sci-Fi & Fantasy

Svetlen grew up in Moscow. A pretty girl, at 18 she won first prize in the Miss Moscow beauty pageant. Olga also had won a beauty contest. Both had been hired as secretaries to work in an underground bunker. While exchanging notes with another secretary there, they discovered that she too had won first place in a beauty contest. The girls typed up endless...

Empty Nest Escapades Ch. 03

by smithbill1970 on Mar 6, 2018
Loving Wives

This story is focused on the male on male piece of the encounter, if this is a bother for you do not continue, if not then enjoy. Thank you, LarryinSeattle for his efforts in making this much more readable. ***** Doug finished his shower, dried himself, and went to check on the two lovers. Seeing them still cuddled up in each other's arms asleep, he starte...

Caught In Lingerie Ch. 02

by hicutlover on Mar 5, 2018
Transsexuals & Crossdressers

As I awoke, I found myself on my side, with Tim's arm wrapped around me. He too was sleeping. I looked at the clock and figured I was out for 30 minutes or so. My bed sheet was covering the two of us and all I had on was my bra and thigh highs. Tim was still naked. My sissy clitty was hard; my horniness woke me up and I wanted more cock in my boypussy, right...

The Unexpected Guest

by CRWestminster on Feb 6, 2018
Erotic Couplings

It had been 6 or 8 months since Surena and I had last visited them in their small desert town. On that weekend we had swapped partners for the first time. We all enjoyed ourselves but, we hadn't heard from them in 4 or 5 months when the phone rings. It's Bob. "Hi, guys...what's up?" Bob was passing through town and was wondering if he could catch a shower a...