older woman sex stories – Page 20

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 Mary...

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

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....

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 me...

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 Extraordinary Old Woman, A Willing Young Man

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I could barely walk by the time I made it to the doctor's office, or 'surgery' as they called it. An old woman sat behind a desk doing some paperwork. 'Can I help ye?' she said in the thick accent of the Scottish islands. 'Would it be possible to see the doctor right away?' I asked. 'What's yere problem then?' she asked, staring at me with huge blue eyes through large round glasses. 'I have a pain in my groin.' I said. 'Are you the doctor?' 'Aye, I am.' She said, getting up. She was thin, and as high as...

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...

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...

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Tags: anal, anus, masturbate, medical, mommy, nurse, older-woman, punishment, rectal, rectum

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 one...

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

A New Learning Experience

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My relationship with my two aunties had always been filled with sexual overtones for as long as I can remember, with references made to how I would always be trying to sneak a look at my aunties' stocking tops and lacy panties whenever I could. However, things began to take a more serious turn when I heard my mother telling them how she had caught me wanking into a pair of her panties and my aunties from then on seemed to provide me with many more opportunities to get a good look at them whenever they came over or whenever...

A New Peter

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A New Peter 1 Mrs. Veckly could hardly sleep that night. After her discussion with Mrs. Bradford, her accountant, the day before, she finally felt she was going to get some control over her twelve-year-old son, Peter. Peter was going to find his new place in the family as well. In their casual conversation, Mrs. Veckly had mentioned that she was having some trouble getting Peter to behave. Mrs. Bradford seemed unusually interested in this and offered some advice. According to Mrs. Bradford, Peter needed to be raised the same way she had raised her son. That meant that Peter...

12th Birthday Medical Exam (part 3)

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In Chapter 1, we met Family Practice Doctor Marcy Harris. The 52 year old woman with two grown children of her own was a respected Doctor that gave thorough exams. On this particular morning, she reviewed all the patients she would see that day with her head nurse Janet, noting that she had a brand new patient named Michael Sanchez, age 11, as the last patient of the morning. "Why does his name sound familiar?" Dr. Harris asked Janet. "You had his dad as a new patient a couple of months ago," Janet replied. Then with a giggle Janet added,"...

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Tags: anal, anus, doctor, medical, nurse, older-woman, rectal, rectum, spank, spanking

A Friendly Neighbor Offered Me the Use of Her Shower

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I lived in an apartment complex with a friendly, older, neighbor lady a few doors down from me. She always had a cheery smile and hello for me when we'd see each other, usually at the mailbox. We never really talked much up until this. But she got to know me very well. I had a leak in the shower of my one and only bathroom, and the management was in the process of repairing it. The leak was fixed but there was a big hole, exposing the plumbing. It wasn't planned on being completely repaired till that next Monday....

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Tags: older-woman

After School Helper

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PART ONE I had always been interested in the sciences during my schooling and at times I nurtured visions of myself as a great physicist, in the mould of Isaac Newton, Maxwell or Faraday. Of course I was interested in Biology but it seemed to be a branch of Science of more interest to the girls. I was somewhat surprised therefore, when one afternoon, just as I was pushing my bike to the school gates, Miss Griffith the Biology teacher stopped her mini and asked me if I would like to help her with some work she was doing. She...