Older Man Stories

255,186 results
Orientation
Length
Source
Infinite Scroll

North to Alaska

by komrad1156 on Sep 15, 2017
Mature

"A sense of adventure is one thing. You could go scuba diving in the Keys or zip lining in Costa Rica. Moving to Alaska is...insane! Somewhere along the way you must have seen episodes from the '90s TV show, Northern Exposure. You know, the Jewish doctor from New York who goes to Alaska to pay back the state for paying his medical school tuition and ends up...

Lockdown Toy Boy

by BarracudaSwordfish on Jul 13, 2020
Mature

This is a lockdown story, but not necessarily the lockdown we are experiencing at the moment. It is merely the vehicle for the story. In it, a naïve and inexperienced eighteen-year-old boy and an older woman with an interesting past find themselves isolated together. They are a long way from civilisation and things inevitably happen. All those participatin...

At the Cabin

by Duskford on Sep 26, 2017
Amateur

Welcome, everyone. Thanks for checking out the story! This is 'At the Cabin', but despite its title, over time it became more than just a story about teens spending time at a cabin, because it became more about the characters than the setting as we expanded on their backstories, their families and the small town they live on. The story wasn't and isn't writt...

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What Craigslist Got Me!

by SissySlutPrincess on Oct 13, 2017
Transsexuals & Crossdressers

I had been crossdressing and playing by myself for years. A simple fun way to pleasure myself and satisfy my love for all things girly. I just needed more being from a small Ohio town made it tough to actually find someone to share this leisure with. Everyone knew everyone so no one wanted to get caught, but me! I decided to check out Craigslist. I posted a...

Young Nastya Earns Her First Salary

by lukefantasist on Oct 15, 2017
First Time

Young Nastya waited in the hotel room for her first client for what felt like eternity. Her boss had dressed her in a figure hugging skirt and a simple white vest. She wasn't wearing a bra and her top was tight and revealed the shape of her perfect firm breasts. She didn't know exactly what was going to happen but she needed the money so desperately, and it...

Captive to a Dark Night Ch. 02

by DancingNymph on Sep 13, 2017
BDSM

I woke up to a throbbing head against the bright light, a hand that was numb and tingling in its cuff and a dick trying to wedge its way into my asshole. "Gah!" I said into the black silk sheet. My curls were in disarray on a plush pillow. I lay on my side, my breasts fondled by a large hand. I turned my head and saw Derek's eyes staring into my own. His w...

The Dirty Old Man

by fuckbunny21 on Sep 19, 2017
Mature

"So now that football season is over what are you going to do with all your time?" I asked Josh. Josh was a friend of my folks and a complete babe. He would come over almost every Sunday to watch the game and drink it up with all of the others. "I have no idea," he faked a frown when he said; "I just don't know what I'm going to do with myself every Sunday...

Girlfriend Finally Cuckolds Pt. 02

by writemarksmith on Sep 13, 2017
Fetish

After I had watched my girlfriend strip for her ex boyfriend Barry and give him a long, slow handjob, she teased me about it constantly. "He really loves my ass. Did you see how he couldn't keep his hands off of it?" she'd ask even though she knew very well I had seen and memorized every second. "His cock got soooo hard. I really wanted to be good but I co...

Addicted to Love

by rachlou on Sep 13, 2017
Reviews & Essays

Thanks to all those men who gave me such great research material... * * * About a month ago I bought a book called How To Break Your Addiction to a Person, written by Howard M. Halpern, PH.D. I am not a great lover of self-help books; the one or two I have purchased over the years have been hit and miss to say the least. (The only truly useful one was Hot...

A Different World Pt. 03

by Henry_C_Roberts on Apr 25, 2018
Sci-Fi & Fantasy

"...as she adjusts her outfit. Standing in her white high heels, she looks amazing. The transparent blouse is tied just under her vastly ample chest. With her mountainous chest lifted and on display through the top, her HH breasts are a perfection of art on display." Copyright © 2018 by Henry C. Roberts. All Rights Reserved. Copyrights: This story is w...