older woman sex stories – Page 7

Sensible Shoes

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I am a shoe salesman. I work at GERARD'S, which is a small up scale independant shoe store in west L.A. We sell women's shoes, and, in order to compete with the big stores we have to give the customers reasons to come in to our store rather than going to the competition. One of those reasons is our policy of service to the customers. The boss says, "Treat 'em like they just bought a dozen pairs, whether they ever spend a dime or not." That meant measuring every foot, and helping them on and off with shoes, which means...

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

Sexy Godmother

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My father left when I was 12 years old and shortly after that my Godmother Betty began to take a special interest in me. She stopped at our house often, brought meals and took me out to plays and concerts. Betty was about 40 at the time, a large woman with huge voluptuous breasts. She was five years older than my mother and treated her like a little sister. My general impression was that Betty was a lesbian, since she lived with a woman and my mother always avoided questions about her, including why she never got married. By the...

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Tags: masturbation, medical, nurse, nylon, older-woman

Rick and Caroline part 6

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Caroline greeted me at the back door after I'd knocked twice. After my outing with the three women my night of appreciation, I didn't know what to expect. She seemed happy to see me as she pushed the door open for me to enter. Caroline must have been in the shower, her hair looked damp and I could see that she'd just started to apply some make-up. She wore a vividly sheer black top; it was a small jacket of sorts. With a single tie just below and between her breasts. From the join between her breasts (that just screamed...

Peter File #11

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In which Nurse Collins recruits Peter for a demonstration of patient care procedures. Editor's Note: Every practicing nurse is well aware of the involuntary sexual arousal experienced by many male patients receiving enemas. The symbolically submissive posture of the enema recipient, the forced exposure of private parts of his body, the sense of personal invasion, and (most importantly) the intimate pressure of the warm enema fluid on his sensitive prostate gland often produce a sexual response in the male. Although the response is harmless and entirely involuntary, and usually goes away as soon as enema delivery is completed, many men...

Peter File #13

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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 only recently discovered the boyish pleasures of masturbation, and he was looking forward to having opportunity to explore them out of the supervision of his parents. Little did he know that his mother's suspicion of his secret activities was the prime motivation for...

POISE ‘N’ IVY

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by Mike Hunt Right after school was out for the summer that year, I was 15, I decided that I needed a job to supplement my meager allowance (at least I thought my allowance was meager); but, try as I might, none of my job hunting was meeting with any success. Needless to say, I was getting pretty discouraged! Then one Saturday afternoon, mom was having coffee with Ivy Johnson, a very good friend of my mother's. Ivy had been a widow for a few years and was in her late fifties, she owned a women's wear shop in town....

Posh Mum

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I had never really thought of my friend Pat as 'posh', but his mother certainly was. Her voice had the beautiful lilt of the refined southern Irish. Her manners were impeccable. She looked the part too with short, very dark, well cut hair, a slim but shapely figure, elegant clothes and a regal bearing. You felt you had to be on your best behavior in her presence. At fifteen I fancied her desperately despite her being an 'older woman' of around forty. When she opened the door to me that morning however, she looked just a little flustered. "Hello," she...

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Tags: masturbating, masturbation, nightgown, older-woman

Reaping the Benefits of a Drinking Sister and Mother

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Terri sighed. Here was another Friday night, and the fifteen-year-old was stuck baby-sitting her brother again! By all rights she should be out with Bobby Flynn right now! Specifically, she should be in the back seat of his beat-up old car, with her legs up in the air while the twenty-year-old college student used up three packs of condoms giving her the pounding she craved! She had grown so used to Bobby bitching about using the condoms, that she considered it just a part of foreplay. Despite all his begging to go bareback just once, he was scared shitless at...

Rick and Caroline part 3

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The next morning Caroline greeted me at the door wearing the shirt to Rick's pajamas. She had on a pair of feather trimmed high heel slippers. As she walked up the few steps into the kitchen I saw the bare cheeks of her ass. "Coffees ready!" She said, placing a cup on the end of the table where I usually sat. I could smell the bacon cooking in the frying pan. "RICK! Rick your breakfast is ready!" She called out lovingly to her husband. "I'm so hungry I could eat a horse!" Rick said coming into the kitchen. He was...

Panty Drawer Spanking

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I was at my friend Linda's house. Linda was a year older than me but we were very good friends for many years. Linda and I were going to go swimming that evening, but first she had to baby-sit a couple of neighborhood kids for a couple of hours. Instead of going home, we decided I should just wait at Linda's house. Her Mom was at work and I could watch TV for a while. When Linda left I waited for 15 minutes to make sure the coast was clear. Deciding it was safe; I headed to her bedroom and...

Panty Mom

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This story is of my most shameful, darkest secret, of how I have seduced my only son and become his lover. Although the attraction between us is mutual, it was my inability to control my own lust that has brought us together. I know it is shameful and wrong, but I don't know how I could ever stop sleeping with my son now. It all started when I arrived home a little earlier than usual one day, after closing a sale at the real estate office where I work. After letting myself in and kicking off my high heels, I...

Panty Thief

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Chapter 1 Cammy moved as quickly and as quietly as he could along the upstairs hall making his way to the closed door at the end. When he got there he pushed it open with a slight creek of the hinges and then slipped soundlessly into his cousin Giselle's room closing the door with a soft 'click' of the latch. The room was femininely appointed, definitely decorated to suit a teenage girl's tastes, but Cammy barely noticed as the 15-year-old made directly for the long low dresser against the wall. This was the most daring thing he had done to...

Paperboy Adventures

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I LOVE the stories that have been submitted recently about women's underwear, exhibitionism, and voyeurism. I had several experiences as a young teen that turned me onto girls' underwear for life, and still to this day I enjoy the occasional wank with a nice silky pair of panties, a slip, or pantyhose. The summer I was 14 I delivered newspapers in my neighborhood. I had about 30 customers, and it would generally take me an hour to pedal my bike up and down local streets in the late afternoon to make my deliveries. My favorite days were Friday, "collection day."...

Party Girls

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I was about fifteen. I was invited to a party to accompany a sweet young girl I had my eyes on. She wasn't all that interested in me as it turns out, but I was obviously good enough to be asked to take her. Anyway, all the people there were her friends and relations and I was the odd one out. She wondered off almost as we arrived, to talk with her friends, and left me sitting with a drink, in the corner of the sitting room. I scanned the room and soon worked out who was going with who...

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

Party Preparation

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By Dennis It was last summer and I was going to have a party at my house for all the folks who work in my office that I deal with daily. We are all computer professionals of some sort and there are only about 20 of us. I gave out the invitations and had a response of about 16 people coming over. One of the attendees was going to be the new procurement specialist we just hired. She was young (about 26), petite and very cute; small with just enough curves to be attractive. Being somewhat older than her (40),...

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Tags: older-woman

Paul and His Mom

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The Robinson's were a typical family. John Robinson, 48 years old — the father was a well known lawyer. He was a busy individual. He usually was at his office all day working. Kate 44 years old - the mother - was his secretary before he married her. After the marriage they decided that it would be better for her to stay at home to raise their son Paul, who was now 14 years old. His relationship with his mother was a normal mother - son relationship. They both loved each other very much. Kate despite her age was still...

Peeper

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It was shortly after my 11th birthday when I made the biggest, most important discovery of my life. You guessed it. I discovered the joys of sex, or at least the joys of masturbation, which was as close to sex as I had gotten. It all started one day when I was given the job of cleaning out the garage. My parents had gone shopping, and had promised to give me $10 to go to the movies if I had the garage spotless by the time I got home. I was moving some boxes that had been stored in the...

Pantasy

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As I got older, I began to feel naughtier and naughtier. There's just no other way to explain it. I began taking bolder and bolder chances and actually wanted to get caught in women's underwear. This idea electrified me and began to occupy my every waking thought. The idea of a woman walking in on me, Seeing me aroused in her panties, on the verge of cumming in her silky soft panties right in front of her filled my fantasies day and night. I began to befriend an older neighbor woman in the building. I had known her for years...

Panties

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Why do they commonly and generally refer to the singular of panty in the plural, as in panties? That always struck me as odd. Yet, now that I am so accustomed to writing panties instead of panty, when I write panty, it just does not sound correct. I end up changing it back to panties. This story is about the only fetish that I think that I have and that being, panties. I do not think that I have another fetish. Well, now that I think of it, I am definitely a tit man. I love tits, big tits, medium...

Nurse Kathy

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*** Danny didn't like going to the doctor. At 14 years old, he didn't feel comfortable being naked in front of other people, let alone a woman, and his mother had insisted on taking him to pediatrician Dr. Joyce Cameron for his checkups. What's more, his mother would stay in the examining room and nurses would often wander in and out while he was undressed and undergoing what appeared to him to be humiliating procedures. *** Nurse Kathy showed Danny and his mother into an examination room. The nurse had Danny strip to his underwear and then weighed him and...