older woman sex stories – Page 3

Voyeur

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"Show time" exclaimed Nat. "What?" asked his friend Steve. "Shut up and watch" Nat ordered, passing a bottle to his friend, "and enjoy." Puzzled Steve looked out of Nat's bedroom window. He hadn't realized until now that Nat's room looked straight into his neighbour's bedroom. Moving about he could see Mrs McPherson sorting through draws and placing items on her bed. "She doesn't realize that we're watching," Nat explained, "Because of the tinting. She probably thinks I'm still at school." The two friends watched in silence, occasionally sipping their drinks. Mrs McPherson stood and stretched. Steve...

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Tags: masturbation, older-woman

Watching Alex

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Hello again. If you have read my previous stories you will know that I'm a married woman who loves to have sex with boys. The ringing of the phone ruining the mood I got up to get it. I was watching on of my favorite home movies while I fucked myself with a vibrator when the phone rang. "Hello?" "Hi Rachael, it's Jen." "How are you sweetheart?" "Oh I'm fine. I have a favor to ask you." "Sure anything." "Well Jack and I are going for a weekend vacation and at the last minute our babysitter fell through I...

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Tags: big-breasts, huge-tits, older-woman, punishment

Trick or Treat

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Henry felt like an idiot. Here it was, Halloween. All his friends were out egging people's doors, throwing water balloons at cars, and just generally causing trouble -- exactly what every 14 year-old boy SHOULD be doing on this day in a small town ... exactly what he should be doing. Instead, thanks to his mom, who had to work an extra shift tonight, he got stuck walking his little sister Trish around for trick-or-treat. It just wasn't fair. He loved his sister and all, and she wasn't nearly as much of a pain in the ass as some 8...

Tutor’s Lonely Wife

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When I was 15, I was struggling with math class and my mom arranged for an accountant she knew from work to tutor me in private lessons at his nearby house. He was apparently a very busy man, because sometimes he would show up and sometimes he wouldn't. However, his wife was always home and was always very friendly, kind and courteous. In fact, I was enamored of her... a typical schoolboy crush for an older, very attractive, more sophisticated woman. Even though I had a girlfriend at the time, I'd hang out with her during aborted lesson times anyway...

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Tags: doctor, medical, nurse, older-woman

Tutor Tits

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My wife, Judy, and I have been engaging lately in exposing her naked body to all sorts of men as foreplay to great times of sex between us that she likes to use as her excuse to do it. She has long been an "innocent" exhibitionist that enjoys being braless and can fluster even good friends or neighbors when we're out working in the yard where she will tease them with close-up views of her nipples poking into the thin tops that she deliberately chooses to wear when she knows she might get caught. Our intentions have always been that...

Two Older Women in the Hot Tub

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My parents hosted a Halloween party this year, and I usually only stay a little while before I go to meet my girlfriend and other friends my age. This year, my girlfriend had to work, so I decided to stick around at my folks party and see what the older people do for fun. Boy was I surprised! Since I wasn't going anywhere and wouldn't be driving, my Mom and Dad let me drink "adult beverages" with them and their friends. I was sort of a hit with the crowd, as I had a well known burger franchise mascot's costume...

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Tags: nylon, older-woman, stockings

Umbrella!

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We are four normal guys, perverts. I'm Gary, that's my best friend, Joey, the one with the black hair, and my other friends Billy, with the blonde hair, and Arthur, the tall, skinny goofy one. We attend the same college in the Northeast and return home to Dayton, Ohio during school breaks to touch bases with our parents; after all, they are paying the bills. Our friend Arthur, the nerdy one of the bunch, developed a sudden interest in hypnosis after watching a video from Japan where they hypnotized a group of women to crawl around the floor while wearing...

Underwear Enjoyment

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I was fascinated by panties, or knickers as we call them in the UK, when I was quite young. I even asked my mother if she would buy me some, but of course she wouldn't! Oh well. I wanted to wear the sort of panties that girls wore at that time (in the 1950s), which were made from soft silky nylon, with firm elastic round the legs, and made in a variety of colors from white, through pink, pale blue, navy blue, red, brown and dark green and others. I had no sisters to 'borrow' from, so my dream was...

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Tags: anal, anus, masturbation, nylon, older-woman, rectal, rectum, stockings

Unexpected Exam

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Wednesday 2:00 PM. I was 16 at the time. Sitting in my 7th. period Civics class. My girlfriend Misty Jones was in the desk beside me. I sat there undressing her with my eyes. Just one more hour and the two of us would be on our way to her house. And I’d be undressing her for real. Her mom is single and usually works late. And gives us hours of quality time to do as we please. Of course she doesn’t know, but does have her suspicions. Motherly instinct I suppose. Or that’s what I thought. Unfortunately things went...

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Tags: anal, anus, doctor, humiliation, masturbation, medical, nurse, older-woman, rectal, rectum

Unnatural Desires

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--==+==-- Miss Barbra was pleased with herself. She had finagled a whole week off from work and planned on spending the entire time at the beach. This was what her Dennis, her son, had asked for his ninth birthday. She was glad to be able to do it. She had felt guilt in the past for the time she spent on the job and she felt like this was a good start in making up for it. They arrived and checked out their room. She was pleased, it was neat and clean. He was pleased, it was barely fifty feet...

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Tags: masturbation, mom, mommy, mother, mother-son, nightgown, older-woman

Tom Part 1

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Tom was a happy teenager who lived in a city apartment with his mom and dad. He attended Washington Junior High School where he would be graduating in three months. He was captain of the school baseball and basketball teams as well as the debating team. Tom was handsome, athletic, a very good student and was very mature for his age. Although he was very popular with both the boys and the girls in school, he had no steady girl friend but did date frequently. One Friday night when Tom was eating supper with his mom and dad...

Tracy Has a Pizza Delivered

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By Slippy Three nights ago Tracy Hunter was out shopping and headed home when she got an idea what to do about dinner. Since John was out of town and she didn't want to go to a lot of fuss, even as hungry as she was, an idea came to her mind that would prove to be one of the best ideas she had in a long time. " PIZZA! That's it," she thought, "I'll have a PIZZA! Humph, maybe I'll get it with extra pepperoni!" Tracy pulled her sporty little convertible into the Pizza Palace and strutted inside. Of...

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Tags: older-woman, punishment, stockings

Travels with Aunt Leigh

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Part 1 Troy was at that age when a growing boy walks around with a, more or less, perpetual erection. And there’s only one thing on his mind:sex….sex, sex, sex, and more sex! It was driving the kid crazy! And it didn’t help that he lived alone with an attractive “older woman” -- his 40s-something aunt, who also happened to be a good-looking blonde. He remembered when his roommate, Patterson, first met Aunt Leigh, at one of those parents’ days at Hillcrest Academy. Standing at the window of their room, Patterson took a moment to eye up the slender blonde...

The Wicked Landlady

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***Need House to Share:*** ***Woman and teenage son.*** ***Please call 555-1234*** Tommy and his mother Pat had moved in with Mrs. Carol three months ago. Mrs. Carol quickly called Pat after seeing her ad in the paper. When they came over she told Pat the rent was half what she had originally intended to ask. The reason was Tommy. The teenage boy was simply adorable and she wanted him under her roof. Pat jumped at the chance to rent space in her lovely Victorian home, and Mrs. Molly Carol seemed like such a nice, benign older woman. After they moved...

The Woman in Apartment 3B

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I lived in an apartment building in New Jersey when I was 12 years old. My bedroom window looked across an alley to the bedroom window of apartment 3B which was occupied by an older heavy set woman of about 58. She wasn't anything special but she was the first woman I saw naked, she was also the first woman I saw masturbate and the first woman who ever let me touch and lick her. It all started one night when I woke up in the middle of the night and saw the light on in 3B. I went to...

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Tags: masturbating, masturbation, older-woman

Tommy Has an Owie

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Tommy has an owie Part 1- 4 Little Tommy Jenkins was, as they say, not the brightest bulb in the box. Although this was due more to his strict, religious upbringing, and overly protective mother, than any mental deficiency. Never the less, he very often gave people the impression that he was much younger than his real age, which was twelve. Lately he'd been having a problem. His body, which was not hampered by any outside influences, was starting to respond in a manner quite common to adolescent boys. To put it in his words, his pee-pee was...

Tommy’s Wicked Stepmother

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"And I want you to be in punishment position when Miss Caulder arrives Tommy". The boy was mortified upon hearing this over the dinner table. His stepsister Julia looked at him and snickered. What his stepmother was saying was that he would have to be totally nude for the visit from his 7th grade teacher tonight. These punishments began shortly after the death of his father. Whenever his stepmother, Sondra, felt he had misbehaved she would strip off all his clothes and humiliate him somehow. After dinner Sondra said "Julia, be a dear and help Tommy...

The Tests 10-2

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The week following Gladys' party Felicia called Sally. She wanted to have coffee and talk so Sally arranged a meeting at the usual coffee shop next to the interstate. It was Felicia's day off so they met when Sally was on the way home from work. Felicia arrived first and Sally met her at a table in the back. They made small talk for a while and got to know each other better. "It seems like you had something specific on your mind, Felicia," said Sally. "Yes, I really do," replied Felicia. "I feel I can talk to you honestly...

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Tags: older-woman, satin, stockings

The Truth, The Whole Truth & Nothing But The Truth

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This is a true story, although it happened many years ago, I remember it as though it was yesterday. Only minor details have been changed to protect identities. It happened to me when I was 21. I was still living at home with my parents at the time. My sister (Kelly) who is 3 years older than me, left home and got married (to Eddie) at the age of 17. Kelly had a gorgeous little girl called Amy who was 4 years old. I often visited my sister on a Saturday afternoon to see my niece and play with her,...

The Unexpected Physical

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By the time Jason climbed off his bike and walked it over to the rack, he was sweating like crazy and could barely feel his legs. It had taken him nearly an hour to pedal up the hill to the high school -- in August heat, no less. But with both his parents at work and no friends who drove, it was the only way to get to his sports physical. He couldn't wait until next year, when he'd be 16 ... old enough to get a permit and start driving himself places. Jason leaned his bike against the rack,...