Dirty Old Men Stories

253,495 results
Orientation
Length
Source
Infinite Scroll

Coming of Age

by slyc_willie on Sep 13, 2017
Mature

(Author's note: This is an official entry into the 2009 Literotica Summer Lovin' story contest. It is a work of fiction concerning a brief, May/December relationship between a young man and older woman. I hope you enjoy this little tale, and please don't forget to vote.) * * * * "Andy! Package pick up!" I was halfway across the warehouse, approaching the...

The MD and IT guy

by tallone123 on Sep 19, 2017
Mature

Working in a bar So here I am due to some financial miscalculations during my university years having to work 2 jobs, during the day I work in the IT department of a large financial services company in Colchester, 3 evenings a week I work in a local bar to make ends meet. My name is Steve and I am 24 years old, I am 6ft tall with dark brown hair and an av...

The Plumber's Daughter Ch. 03

by beagle9690 on Sep 19, 2017
Romance

"Dad, I....." "Your father went storming out to the garage, dear," Mom said, coming back on the telephone, "don't worry, he'll get over it. I'm looking forward to your visit and meeting your young man. I have a feeling that Patrick will be quite a challenge for my Dominick..." After I finished talking with my mother I went looking for Patrick. I found him...

Accidental Daddy: A TS/CD Novella

by RoryOmore on Dec 24, 2018
Transgender & Crossdressers

Authors Notes: This is an edited and consolidated version of "Accidental Daddy," originally posted in separate parts between November 2017 and March 2018. ----------------- This was my first attempt at a TS/CD story, written to explore the reactions of a straight older male on encountering a sissy for the first time. Tory Buckingham was inspired by my im...

Rodney's Nude Humiliation Ch. 12

by aaronburr on Nov 7, 2017
Exhibitionist & Voyeur

It was the living room of Mrs Reilly's house, high-ceilinged and richly decorated, a room all the ladies of Brewer longed to visit. The light poured in the tall bay windows, catching the swirl of the women's cigarette smoke. On the wall, in the shadows, one could just make out the oil painting of Venus hauling a nude Cupid over her knees- an 18 year old Cupi...

How To Get Ahead

by TheDarkCloud on Sep 14, 2017
Erotic Couplings

Julie sat on the soft chair in the reception area and flicked casually through the magazine. It was a generic women's magazine and held no real interest to her critical eye, though she did enjoy the various pictures of famous actresses and singers who were perceived as "hot". They didn't impress her; they didn't even know what "hot" was. Now someone with the...

Bottoms Up

by SEVERUSMAX on Sep 13, 2017
Exhibitionist & Voyeur

I was just barely done unpacking boxes for the afternoon, nice and sweaty as a result in the hot August sun. Whatever possessed me to move to Georgia during the "dog days" of summer was beyond me. Well, it was the furthest thing that my wife expected when I left her and took my half of all bank accounts to roll over into my own. Sorry, Ginger, but I wasn't g...

Coffee and a Blowjob

by younghungblack on Sep 13, 2017
Interracial Love

Angie is a real woman with a strong desire to submit to a big, black cock. This story contains aspects of her real and fantasy lives...and yes, some of mine as well. Everyone in this story is above the age of consent. * For the ninth time in ten days, Angie parked her silver Honda Accord in front of the convenience store, opened the door and swung her nylo...

Going to Night School

by vanessa.evans on Aug 19, 2017
Exhibitionist & Voyeur

Hi, my name is Vanessa. I was born in December 1975 and now have a 34A--24--35 95-pound figure with blond hair. In 1998 I quit my boring existence in a little town in North Wales and went to work as a Housekeeper for a middle-aged man in the East Midlands of England. It was a brave decision to make as I'd applied for the job after seeing the job advert in a...

To Love And Not to Love

by Kalies on Sep 15, 2017
Loving Wives

Cara checked herself out in the mirror and smiled. She looked good. Okay. She looked beyond good. Her rich mahogany brown hair was straightened and styled to flow like liquid chocolate down to her waist. Her choice of cloth for the evening? Leather. Lots and lots of figure-hugging leather. She loved the way her favorite burgundy red leather top accentuat...