Older Guy Stories

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Older Guys are Fun

by Etaindarcy on Jun 5, 2019
Transgender & Crossdressers

I was 24 and living on my own in a different town from where I grew up. It was far enough away that I could be anyone I wanted to be and so I got deeper into dressing up. I had a good job now, so I could afford some nicer clothes, and now that I had my own place, I could order things through the mail without worrying about prying roommates or parents. In th...

Older Guys

by goodtimes21 on Nov 16, 2020
Anal

What really excites me changes from time to time. I have been watching the guys on the internet. Getting their cocks out and wanking. So many beautiful cocks. Cut, uncut, Big, small. Somewhere it feels like the hot ones should be the young guys with the muscles and the big cocks and the tight bottoms. But its not them. They dont work for me. If I'm going t...

Young Luci Cleans For Older Guys

by lucioz on Sep 14, 2017
Mature

A young student needs money, to help get her through university. This is based on a true story. My thanks again go to "The Big Bopper" who has helped me so much. At the request of many readers, I have started to use the words, pussy and cunt which I have never liked using. So here goes, thanks to the guys for pointing this out to me. * I had one year to...

MWF Likes Older Guys

by ezygoing4U on Feb 7, 2018
Erotic Couplings

Single living in north central Ohio and dateless. I'd been with a lot of women, more FWB than dating, but was in a dry spell and needed some company. I joined a couple dating sites and started answering some ads. A gal from Columbus seemed interested, we chatted online several times. Very pretty, blonde, about 10 years younger than I and I was in my early 40...

The Korea Girl at the New Aloha Spa

by EllenMelville on May 2, 2018
Exhibitionist & Voyeur

Some older guys are buddies of mine. Winters in Sag Harbor only the fire department bake sale and amateur poetry readings at Ashawagh Hall are exciting. I show up at Rowdy Hall in a tight red dress and start the intravenous Chardonnay drip and make friends. Too bad Rowdy Hall doesn't stock white Burgundies at $250.00 a bottle; I know my buddies would compete...

A First for Three

by Airagone on Sep 19, 2017
Group Sex

Like any older guy it is a fantasy to find a twenty something, hard body who likes you in more than a fatherly way. As an outside salesman I’m often in contact with younger, attractive girls. I flirt and flatter and they accept, as one of them put it, “Oh, I know you’re not REALLY serious”, my subtle advances. It is on occasion that I will entertain a grou...

Dreams of Yesteryear

by Dirkstimson on Sep 1, 2017
Group Sex

The four older guys were sitting in a booth at their favorite bar, almost empty early on a rainy Tuesday evening. They were talking about their kids, the prospects for the Giants this year and how life had treated them. None of these were new themes. Max heaved a sigh. "I can't tell you how happy I am not to travel any more! God! There was a time I woke up...

My Crazy Neighbor

by midnightdeathwriter on Sep 13, 2017
Mature

I'm an older guy; I don't look anywhere near as old as I really am, but I'm in my mid fifties. I'm active and healthy, and haven't' succumbed to "middle age spread". I'm also the "Handy" guy in the neighborhood. I used to have an old schoolmarm living next door, but she finally moved out and a new neighbor moved in. She was mid thirties, and she had a daught...

Good Things in Large Packages

by Silverstag on Sep 17, 2017
Mature

For an older guy in the singles scene it's feast and famine. As guys get older the female to male ratio is terrific but the traditional places to meet women are scarcer. Not that there aren't places to meet women - mainly clubs and meat markets but there aren't a lot of older women there. But, remain hopeful, keep a stiff upper lip and a stiff you-know-what...

Dreams of Yesteryear

by Jimmela on Sep 2, 2017
Erotic Couplings

The four older guys were sitting in a booth at their favorite bar, almost empty early on a rainy Tuesday evening. They were talking about their kids, the prospects for the Giants this year and how life had treated them. None of these were new themes. Max heaved a sigh. "I can't tell you how happy I am not to travel anymore! God! There was a time I woke up i...