older woman sex stories

Wish of The Paperboy

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As a youngster I had a paper route in order to earn the extra money I needed to buy some of the goodies that I desired. This was a very profitable route, although it was a once a week delivery. I was always trying to drum up new business. One day my mother told me to go and ask a new family that had moved in, if they would like delivery. Learning of this, I headed to there place and rang the bell. A young girl, about 9 years old answered. I asked if her parents were home. Shortly after,...

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Wonderful Older Lady

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I've been jacking off for as long as I can remember. There is nothing better than laying on the bed naked and rock hard fantasizing about a true life experience, or fantasizing about an experience one wishes they could have. In all my experiences the hottest ones have been where I was lucky enough to be watched by a woman. I've found that in most instances, if I know a woman and I have a good friendly relationship with her, and I am honest and I tell her I'd love to jack off in front of her, most will watch...

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Would I Get Caught in her Bedroom? (part 2)

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By Rick From Part 1: I continued to stroke myself, all the while the pair of dirty panties lay on my face and I continued to inhale the beautiful aroma. As I was ready to explode, I quickly lifted the panties and slip off myself and as I grabbed and moved my tee-shirt, squirted the hot semen all over my stomach. I continued stroking while I smelled her panties ensuring that every last drop would be spent and as I lifted the dirty panties off my face, I opened my eyes to see this woman standing in the doorway of...

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Would I Get Caught in her Bedroom? conclusion

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By Rick From Part 2: The next time she started this routine, she put quite a bit of the vibrator up my ass while her other hand continued to stroke me. I could feel the vibrations all through my lower extremities as she pressed it against the inside of my ass. She felt me tremble, my dick was pulsating, and this time she did not stop. Instead, I exploded all over the inside of the slips and the smooth silkiness touching me was too much to handle. I begged her to remove the slips and was trying to pull my...

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A Christmas Party with an Older Woman

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By Rick I'm a twenty-five year old male and was recently in the laundry at my apartment complex. Usually I don't see many people in here, but just before Christmas just after I had put my laundry into the washers, a woman in her late thirties or early forties came in with her basket full of clothes. She was medium build and wearing a frumpy sweater and dress with what appeared to be pantyhose underneath. She had fairly nice size breasts and an average face. She had her backside to me while she was putting her clothes into the washer...

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Vasectomy

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When I was 29 and dating a woman with two children, I decided that since we didn't want any more children I should be responsible for the birth control so Dianne wouldn't have to take the pill anymore. A vasectomy seemed like the smartest decision. I didn't know where to go for it, but one of my old girlfriends worked at a Planned Parenthood clinic so I asked her. Mary Fran told me that a doctor came in once a month to do vasectomies at her clinic and made an appointment for me for the next open day. She told...

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Voluptuous Aunt Diane

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Voluptuous Aunt Diane Ch. 01 It was a great summer. I was 18 years old, with no job, and no responsibilities. After having been small for most of my life, I had finally had a growth spurt the year before and was up to 6 ft tall, and in great shape. I spent most of those few months in a small town, where I had a lot of family, including my Aunt Diane. Aunt Diane is my mom's younger sister and, at 35 years old, was still a very attractive, voluptuous woman. She has the most amazing set of tits...

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Voluptuous Karen

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--- --- --- --- --- --- --- --- --- --- --- VOLUPTUOUS KAREN -part 1 --- --- --- --- --- --- --- --- --- --- --- No woman in my life had such a fantastically voluptuous shape as Karen Wray, my college landlady. My eternally ideal object of passion. That she was also supremely refined in the art of seduction, you will agree if you read on. This is a memoir of my first amour with a grown woman. As long as I can remember I have been fascinated by women with voluptuous figures, which necessarily implies very large breasts,...

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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...

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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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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...

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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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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...

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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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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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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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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 growing and...

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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 get ready for tonight"....

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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 graduate 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 girlfriend but did date frequently. One Friday night when Tom was eating supper with his mom and dad his father announced that...

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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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