Older Woman Stories

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Older Woman

by jameshart on Sep 13, 2017
Erotic Couplings

When I first met Susan in the flesh I suppose my over-riding emotion was relief. She was just how I had imagined her; long sandy hair, pretty eyes, showing her age a bit - after all, she was in her 40s - but very attractive. She had only flown into London that morning, but was not looking too jet-lagged. I ordered two black coffees from the waitress in the c...

Older Woman from Work

by johnthepostman on Sep 15, 2017
Loving Wives

I was 28 years old and owned my own place. I lived alone in the two-bedroom house following the break up with my girlfriend the month before. Most nights I would masturbate before going to sleep. As I lay on my bed jerking off, I thought about a number of women. There were women at work, a local girl from the same street and of course the barmaid at the pub...

Older Woman Excites Senior Students

by Hopebeach on Sep 12, 2017
Illustrated

Emily Brigstock rose from the wooden seat on the railway station and boarded her morning train. She took her usual seat for the 20 minute ride to her place of work, and then took out the Daily Mail newspaper and lost herself in the stories of the day. She knew that fellow commuters were ogling her legs and her fine breasts because they did so every day.....a...

Older Woman Fantasy Comes True

by a_decent_fellow on Sep 26, 2017
Mature

I have, as long as I can remember, have had a fantasy about being with an older woman. I don't know when or how it started, but it was fueled even more by something that happened between my Aunt and I. (This is not a story about that encounter. See my other story, "In Memory of Aunt Lisa".) The woman that I had married confessed to me that she lost her virg...

Older Woman & Stockings

by Hosieryboy on Sep 17, 2017
Mature

My first sexual stocking experience happened when I was 18 years old. I was visiting my Grandparent's home in Canton, Ohio. There were a few petting experiences that I had with girls my own age in the past, where the girls would let me stroke their legs to the tops of their stockings but that was about it. That summer in Canton, my mother's friend, Irene wa...

Older Woman on Porch

by Red_Dwarf on Sep 2, 2017
Exhibitionist & Voyeur

For the past couple of days I was walking along the country road I live on and about ½ a mile from my place there is this nice house up on a hill over looking the river. It has a fair sized porch with one of those porch style fireplaces with the back of it facing the road so the light of the fire was reflecting back towards the house obscuring the view of th...

Older Woman Holiday

by lilguy on Sep 26, 2017
Mature

This is a story that takes place on a Holiday. You pick which Holiday It also a tale of 3 mature women that hang together. They are 3 women with an appetite for young men and women (especially virgins). They are 3 women who loved to get into trouble and have adventure The characters Beth- Beth was black with short black hair and big hazel eyes. She was 55 an...

Older Woman Fantasy Comes True Pt. 02

by a_decent_fellow on Jul 29, 2019
Mature

LOLLYPOP, LUMBER CENTER AND LADDER From Part One: "She told me how she just loves to suck dick. She loved the taste of cum. She used to suck "her Johnny's" dick just about every night. She would fall asleep under the covers with his dick in her mouth. She said she would wake up through the night and begin to suck on it as if she were a baby sucking on a...

The Older Woman Next Door

by juge1 on Sep 12, 2017
Mature

This story begins when I was a Senior in school. I was your typical 18 year old . I loved to go to parties and like every kid my age, I tried to get laid. I never was successful, so I had to resort to looking at dirty pictures in a magazine and jacking off. Life was unfair, but when our new neighbor's moved in, my life was about to change. The family consi...

The Older Woman in My Life

by Strapping Young Lad on Sep 19, 2017
Mature

I was fifteen when Mrs. Smith asked my mom if I could mow her lawn. I was sixteen when Mrs. Smith became Ms. Smith, and I remember when my mom had commented on how Ms. Smith was gonna be all alone in that house of hers. I was seventeen when Ms. Smith began showing an outwardly affection towards me, which I must confess I didn't really catch upon. Women in ge...