older woman sex stories – Page 19

Aunt Carol

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by Christopher **This story is affectionately dedicated to Miss Juliette Anderson and director Henry Paris, two pioneers, never to be forgotten. ****** 'Understanding women' is an oxymoron. You never really understand them. If you're lucky you survive them. Take exhibitionism for example. Why do some women, maybe even a co-worker or the wife of a neighbor, get pleasure from flashing hapless shoe salesmen or "surprising" pizza delivery boys wrapped in just a towel? Power? Danger? What possesses some women to perform sex in front of others or even before a camera? What is the drive that causes them to...

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Tags: masturbate, nightgown, nylon, older-woman

Aunt Delores’ Panties

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I come from a rather close, extended family in the Northeast part of the U.S. Both my mom's sisters lived within twenty miles of us when I was growing up, and we would see each other frequently. My Aunt Delores was about five years older than my mom. She was divorced when I was fairly young and never remarried. Despite being older, she was the "cool" Aunt in the family, and I looked forward to her babysitting me or spending nights at her house when my parents went out. She was pretty loose with the rules. She let me stay...

Aunt Emily’s Boarding House

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One summer early in Peter's teen years, his mother sent him to stay with his Aunt Emily, who ran a boarding house for young men in the north of England. Peter was quite excited, both at the novelty of the trip and at the prospect of being more "on his own" for the summer. He had onlyrecently discovered the boyish pleasures of masturbation, and he waslooking forward to having opportunity to explore them out of thesupervision of his parents. Little did he know that his mother'ssuspicion of his secret activities was the prime motivation for sending him to the care...

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Tags: masturbation, medical, nurse, older-woman, punishment, udders

Aunt Emmaline

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My Aunt Emmaline practiced petticoat discipline on me from the time I was eleven years old, which meant at age 13 I was quite used to being dropped off at her house by my mother on a Saturday morning to spend what we called a punishment weekend. That meant I had to take off my boy’s clothes the moment I arrived, stand completely naked before my aunt, and let her dress me as a girl. My dress for the entire weekend was nothing more than a light cotton little girl’s frock, pink or white lace panties, and some shiny...

Aunt Estelle

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*** True story of a young boy coming of age in 1950's small Georgia town. *** I was born in a small town in Georgia in 1940. My Mom and Dad owned the only grocery store in town and worked 6 days a week from 7 in the morning until 6 at night. I was an only child and was cared for by my Aunt Estelle. Aunt Estelle was not really my aunt. She was a black lady who took care of me before and after school, cleaned the house, washed clothes and cooked supper every day. She lived on...

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Tags: older-woman

Aunt Eva

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I was raised in a fairly typical big city neighborhood. In those days, families lived pretty close to one another if not in the same immediate neighborhood. My aunt Eva (my mother's sister) lived a few blocks away from us in a 2-flat building she owned. She lived on the 2nd floor and did n't rent the other apartment because she thought it was too much trouble and besides she didn't need the money. My aunt lived alone and never married. Because of that she had to do all the maintenance work herself. Yard-work, paining and whatever else was needed....

Aunt Gina at the Pool (part 1)

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I was a young man of 15 when I was invited over to my aunt Gina’s house for the weekend. Aunt Gina was never married 43 years old and lived alone, she also was very wealthy and had recently had an in ground pool installed. I was included in being able to use the pool anytime I wanted granted I kept it clean and was in on the maintenance of it during the summer. No problem I said. My aunt was a very attractive older woman with blondish hair short around her shoulders, her body was built medium in...

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Tags: older-woman

Aunt Gina at the Pool (part 2)

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I quickly tried to wash all of the soap off of myself as I came back from my heart pounding orgasm I just had looking at my aunt out at the pool. I quickly turned the water off grabbed for my towel and dried myself off and threw on a pair of underwear and some shorts and lay on the bed in my aunt’s room. So this is where she sleeps at night huh I thought. I got up like most 15 yr old boys have an urge to look at what she wears under her clothes so I...

A Three Step Ladder

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She answered the door wearing her usual evening attire, an old worn cotton print bathrobe and slippers. Mrs. "B" was busy hanging drapes, and wasn't sure what time Danny, her son would be home. He had gone with his father to a friend's house for a game of cards and pizza. I had stopped by to see if Danny was ready to go. He and I had talked about shooting some hoops at the park and then cruising the local burger joints and hangouts tonight. "While you're here, would you mind giving me a hand with these drapes?" she asked. ...

A Room With A View

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Jimmy O'Rourke sat on the living room couch as he and his parents watched the movie of the week. It was a hot summer night and the O'Rourke's apartment didn't have air conditioning. The outdated wiring of the old Brooklyn apartment house just couldn't handle the load. Instead the 16 year old had to settle for sitting around in his gym shorts and trying to cool off with the large fan over in the corner. The movie was pretty boring, but his mother seemed to enjoy it. His father had dozed off in his chair about a half hour ago....

An Older Woman

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Way back when I was a lad and living in California I shared an apartment with a friend. Across the way was an older woman who kind of adopted us and looked after us. We were in the service and at the time it was hard for servicemen to be accepted in San Diego and she was very nice to us. By older, I mean she was older than us at the time. We were almost 20 and she was late 30's. My friend had duty one night and I was home alone. Our neighbor had stopped by in the...

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Tags: nightgown, older-woman

Another Mother’s Panties

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My panty love began when I was a young boy, delving through my mother's collection of silky delights. I can't remember the details of the first encounter with panties, that first caress and scent, but I do recall sneaking up to her bedroom when she was out or pre-occupied, and sifting through the pairs in her drawer. It was a feast to the eyes and to the hands. However, easily the most memorable and sensual time in my panty experience was with another mother's panties - my best friend's mother's, Margaret… She was an attractive mature woman, early forties, slim...

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Tags: masturbate, masturbation, nylon, older-woman

Anything To Help Him

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I silently thanked whatever god looked out for teenage boys - thanking that higher power from taking my son in that accident that stole half a dozen other parents children. A school skiing trip - four days of fun away from parents, with friends and only two teachers as chaperons - it had turned into a nightmare. Dozens had been hurt, half of the teens that had went on the trip had been of the fourteen found dead at the scene. Their car having taken the brunt of the train crash. Over a month ago and it still stunned...

Airport Flasher

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My husband, (always the inventive one), thought up a situation where I could let other men look up my skirt. He decided an airport would be a perfect place. There are lots of chairs and escalators and the men there would be going someplace so they would be perfect to give a quick peek to. He laid out one of my shorter halter dresses for me to wear along with a pair of nude color, crotchless pantyhose and heels. The halter top of the dress fit pretty loose on the sides and as I moved it was pretty easy to...

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Tags: older-woman

Alexis My Mother-In-Law

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Alexis never really started to look good until she got her second divorce and my wife and I had her come over more often since she relocated closer to our apartment. She was forty-four years old and had the best butt in jeans I had ever saw. My wife has a great ass and I could see where she got it from. Alex, as my mother-in-law liked to be called, was four inches over five feet and had big, full, and still firm breasts. My sister-in-law took after her mom in that department while my wife got smaller boobs. When...

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Tags: anal, anus, big-breasts, huge-tits, masturbate, older-woman, rectal, rectum

A Love of Lingerie

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Part 1 When I was young, I was playing at a friends house for the afternoon. It was the Summer in the late 1970's. My friend was playing outside. I was inside reading a comic on the sofa, when my friends Mum had a group of two or three others Mums come to the front door. They had been out shopping for lingerie. I think it was M+S as I remember the green and gold carrier bags. They drew the curtains and two of them began undressing. I watched them unbutton their blouses and unzip and slip off their skirts....

A Loving Mother

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I am not sure how to begin this story. But Jeremy, my 11 year old son, has been becoming increasingly bold in his curiosity. We have never made any big deal out of nudity in our family, and I always felt it was important to answer his questions fully and honestly, but not to give more information than he really wants or needs I vowed long ago that I would not infect my son with the sense of shame that so many of us have over sex. Jeremy just turned 11. We've always had a close relationship that got even...

Amazing Grace

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Appearances can be deceptive. When I reread this story, I realised that the opening sentence could give completely the wrong impression. You know how it is with a story, you want to grab the reader’s attention straight away, so you say something a little off-track to try and make him or her carry on reading. However, I must make this clear - although this story contains sex, in fact it’s mainly about sex, there is no incest and no under age sex involved. Sorry if that’s a disappointment to some readers, but that’s the way it is. So let’s get...

A Mother’s Discovery

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Arresting the Slide It is a natural condition that a predator doesn't always choose the prey. More often than not, the prey chooses itself, or rather, gets itself into a situation whereby its ultimate demise is assured. The individual predator that effects the eventual `kill' is merely that which fate has determined is the closest at the time. However, it would be fair to say that the theory loses its simplicity when humans are involved, because while the prey still chooses itself, more often than not, the predator has the wit and will to ensure that he is the...

A New Kind of Bridge Game

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"Whoa, Whoa, who's the new kid?" Betty said turning to the three other ladies seated at the picnic table. "Billy, he's here to fix whatever goes wrong in this place," said Wendy looking up from her sandwich. The four ladies ate lunch every day at the picnic table outside the daycare where they all worked. They were all great friends and enjoyed their daily girl-talk even through there wasn't a one of them under the age of forty. "Well, we've finally got someone to take care of all the little stuff huh? And my, my I couldn't have selected a...

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Tags: anal, anus, big-breasts, huge-tits, older-woman, rectal, rectum