Older Man Stories

255,186 results
Orientation
Length
Source
Infinite Scroll

Tales of Hedonism: Kathy

by Obobby on Dec 16, 2017
Loving Wives

Kathy's Friendly Neighbor I'd gotten so used to the old neighbor's schedule that I didn't even think as I took off my bikini top to lay back in the sun next to my pool in the warm May sunshine of Southern California. My husband, Mark, was off on a business trip for three days and I hoped to be a few shades darker from my pale winter white when he got back....

The Guitar

by Egmont Grigor on Sep 14, 2017
Romance

ONE Frankie served a fat, greasy looking man dinner at 3:15 in the afternoon, the time indicating he was a shift worker. He, she and the useless cook and a part-timer preparing vegetables and loading and unloading dishes were the only occupants in the diner. Fat man kept eyeing Frankie's tits, but she didn't mind. She followed a drill that sometimes worke...

I Almost Lost Him

by LaPatitMort on Sep 14, 2017
Romance

I 'm twenty-nine now. Blond, tall, not fat but with soft curves, a small C-cup and with a combination of hips, legs and ass that seem to attract the men. For the last five years I've stripped and been paid well for the fantasies I have provided to both men and women. The money is too good not to dance. I've had more than my share of experiences and discovere...

Change of Heart

by lilblkboy on Sep 16, 2017
Transsexuals & Crossdressers

[[names changed to protect the naughty]] "Okay, Shasta--what's the deal with that chick?" It was late January. Shasta and I were sharing a cigarette under the eaves of Rod's, one of the more notorious gay hangouts in the city. This one featured drag shows four nights a week, which tended to cause many of the bolder TG girls to visit at least for part of t...

Annie & the Driving Instructor Ch. 02

by badidea211 on Sep 19, 2017
Mature

This concludes Annie and the Driving Instructor. If stories about older men having sex with much younger women offend you, please do not read on. If stories about marital infidelity also offend you, please do not read on. ***** Annie resumes the story about Eddie, her randy driving instructor... "So we get to Stephanie's house and he's basically been gr...

The Long Wait

by Moondrift on Sep 17, 2017
Mature

Trent stood behind the woman being served at the post office counter. "Your name?" asked the assistant. "Gabriele Cracknel." Trent froze and felt the blood drain from his face. "Gabriele?" he said. The woman turned her head to look at him questioningly. "Yes?" There was a pause as they stared at each other then with a smothered cry she said, "Trent, T...

Claudia's Lessons

by xpc316e on Sep 12, 2017
First Time

My story really needs me to paint something of a pen picture if you are to believe how a man in his mid-fifties came to be fucking a group of young women, so here goes. As I said, I am in my mid-fifties, living with my partner Jo for the past ten years. She is a nurse who works night shifts, always at weekends, and when this happened we had all three of her...

Penny's Freaky Friends Ch. 1

by AngelzDevil on Sep 14, 2017
Group Sex

My new fried Penny invited me to a "freak friend party." I had met Penny at work and we had started talking. Slowly over a few weeks it turned out we both liked the same things. Well, specifically one same thing – sex! Penny was 36, a BBW lady, but very pretty, with huge eyes and a gorgeous smile. And she had massive tits, lol. I wanted her tits in my mout...

Kicking the Habit of Virginity

by MaryAnn678 on Aug 18, 2017
First Time

Mary took one last look at herself to see if it had been worth all the trouble. She'd been coiffed, her face soften in a mud pick, a manicurist had taken an hour on her nails, and toenails. And her dress! The designer in a haute couture emporium had outdone herself. She even took care to ensure the slit skirt would almost, but not quite, show Mary's derriere...

Wild Flowers

by Paul44 on Sep 2, 2017
First Time

"You must come with my dear cousin," cousin Grace exclaimed excitedly. "Oh. Why must I come my dearest girl?" I laughed inwardly at her discomfit as I expressed her youthfulness to me. True it was only six months but when you are a man of twenty it all counts. Still Grace was not one to sulk and she smiled quickly enough and pulled at my arms again and bi...