older woman sex stories – Page 15

Girl Time

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"I just don't know what to do with Greg. I caught him going through Alicia's panties drawer again." "Mom, he's 13 years old. You never had boys; you don't know what it's like. They're all hormones and no brains." "I was expecting the normal kid problems when I told Alice that I'd watch the kids for her while she was in Europe. Alicia's no problem. She's 16 and rather mature. In fact, she's a great help in getting me to the store. I was expecting the normal boy stuff from Greg; you know: dirt, scratches leaving his stuff all over....

Girl Time 2

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Amy opened the envelope addressed to her. "Oh mom, it's so great." "What is, Amy?" "Debbie's pool party. It's next Saturday and she invited me to the sleepover afterwards." "Aren't you forgetting something?" Amy screwed up her 11-year-old face and then it hit her. "It's Girl Time!" Girl Time started when her grandmother caught her Cousin Greg going through his sister's panties drawer. Greg was sent for the summer to live with Amy and his Aunt Kay to learn how to be a girl. When his mom got back from Europe she noticed the change in him immediately. He was...

Getting Caught in Mom’s Panties

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I often wondered what would happen if Mom walked in on me while I was dressed in her underwear ever since the close call I had when I was 8. I was wearing her white nylon slip bra and panties. She came home while I was in her room. I closed and locked the door, changed and came out, claiming to have 'taken a nap'. I'm sure Mom saw right thru me and knew something was up. I was so tense it took me an hour to calm down from the adrenaline rush. From then on, I had a heightened...

Forced to Serve at my Aunt’s Tea Party

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When I was 12 years old, my parents went on a two week vacation and sent me to my Aunt's house to stay with her while they were gone. My Aunt Shirley was my mother's older sister. She was about 50 years old at the time. And she was a very imposing woman. She had large breasts, large hips and thighs, and a small waist that was often wrapped with a belt. She was a very strict woman and she informed me upon my arrival that if she was to be responsible for me, then I would not be allowed...

Forced to Wear Mom’s Briefs After Accident

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I have been hooked on panties since I was a child of about 7 or 8 and was forced to wear my mother's panties to school one day after I had wet the bed wearing my only pair of clean undershorts. I went to school feeling very embarrassed and bad for having made my mother so angry. I also must have felt angry at her for having made me wear her nylon panties, and was terrified that some of my friends would somehow find out and laugh at me. Of course they never did, but I felt as though they’d...

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Tags: anal, anus, masturbate, nylon, older-woman, panties, panty-fetish, rectal, rectum

Friend’s Mom

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I was a typical teen with raging hormones I guess. I can remember frantically scouring through my mother’s magazines for a Maidenform or Warner’s ad, inspiring me to go pleasure myself to the image of an almost naked woman. Or of course who could forget the all important Sears catalog. Surprisingly, it would be the underwear that would be more inspiring for me. My life changed when I was 17. I let curiosity get the best of me and the effects of that moment are still with me today 23 years later. Of course I’m referring to my first experience...

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Tags: nightgown, nylon, older-woman

Fun with Aunt Sally

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Both of my parents traveled a lot mostly to Europe and the like. As result I grew up going from place to place, never really developing many friends. As far a my sex education was concerned my parents simply didn't have the time to explain much to me. They were well off and always had business meetings and traveling to do. So I had to learn on my on so to speak. As I matured I discovered the pleasures of masturbation and finding some of dads porno magazines helped me learn a lot about sex. In their travels to Europe...

George part 2

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By BOB The noise and smoke inside the bar was a shock to our senses as we came staggering in, by the time we made our way to the bar through the jammed room the effect of the air conditioning was lost. The place was full mostly men that had stopped in on their way home from work. Luckily we found three stools together at the bar and ordered a round of drinks. There was an uproar as the guys saw Gladys' outfit, whistles and lewd comments from deep in the room. All the attention seemed to inspire her to...

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Tags: anal, anus, older-woman, rectal, rectum

Evan’s Aunt

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Evan had not lived in his aunt's house for nearly four years. After the death of his mother and father at the age of six and a half he had been placed with his Aunt Phoebe and spent the next three years there. Phoebe was not actually his aunt; she was officially his third cousin but, because of the disparity in their years, he had always been expected to refer to her as 'Aunt Phoebe'. When, at the age of 39, Phoebe decided to take a leave of absence from her position as a rural visiting nurse to pursue her...

Exploring Aunt Julie

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When I was 16 my mother sent me to spend the summer at my aunt's house in the country. She thought it would be good for me to spend some time with her side of the family, I guess. My aunt was divorced, in her late 30s, and had three sons older than me. Problem was, they no longer lived at home and were never around. So I spent all my time by myself or hanging out with Aunt Julie. I helped her out with her vegetable garden and lawn work. Now, I had always liked Aunt Julie. She was...

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Tags: areola, masturbate, older-woman

Family Friend Jane

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One summer, when I was 18 years old, my parents went on a vacation. My parents were going to be gone for three months and they didn't trust me to be alone for that length of time. I didn't know how to cook for myself, and I didn't know how to keep the house clean. I had lived a sheltered life where my mom had done all of the housework and I just studied and did my homework. So they had a family friend, Jane, who had just graduated from college, come to baby-sit the house and me. Jane's family...

Female Nurse Takes My Rectal Temperature

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I was 13 years old and that spring I began to develop asthma again. When I was several years younger, I had a mild case of asthma and I was taken to our family pediatrician quite frequently. Because I was entering my teens my mom now switched my doctor to a regular physician and I stopped going to our old pediatrician. I remember that spring day very clearly when my mom picked me up from school and told me that we had a doctor’s appointment, but not at my new doctor. She had made an appointment with my old pediatrician...

Finish What You Started

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"Son, always Finish What You Started," my father once taught me. "It may seem awkward at first, maybe even boring and you may not see where it's leading. But with some stick-to-it've-ness, you'll get your prize at the end with a big payoff." *** When did I realize that I was in love with the most beautiful woman I've ever seen? I've always 'loved' my mother, yet I don't remember when I fell in love with my mom. I do remember that the first time I came from masturbating happened while I was fantasizing about her. That may be when...

First Panty 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...

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Tags: nylon, older-woman, spank, spanking

Doing it for a Younger Girl

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I think this must have happened when I was about 12 as I remember it being quite soon after I first started "playing with myself" as I called it then. For years my mother had been a friend with a woman who lived up our street and I had known her and her two daughters for a long time. My mother's friend kept a small holiday chalet on a development by the coast and we regular used to get invited there for the weekend. It was at this chalet that these events took place. My parents and their friends had...

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Tags: masturbate, older-woman

Don’s Panties

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*** Chapter 1 *** Don was quite small the first time he put on his older sister's pink silk panties but he liked it. He was quite upset the first time his sister and her girlfriend caught him wearing these panties. "What on earth are you wearing," Jane said as she and Judy walked into the room. They stood staring at Don wearing nothing but pink panties. "You're not supposed to be here yet," was all the young Don could say but he knew he had been caught. "Wait till I tell Mom," Jane laughed. "No, please you can't tell...

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Tags: humiliation, masturbate, masturbation, older-woman

Ed

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The school bell rang, sounding the end of the school year and the start of summer vacation. No one could be happier than Ed. The thirteen-year-old boy walked home from school with his two best buddies, Chuck and John. They planned all of the things they were going to do this summer, fishing, swimming, and long bike rides. Ed lived in Miami Fla., with his mom Jen. He was an only child and his dad left them when Ed was only four. Jen worked in a market and supported Ed all by herself. After supper that night, Jen told Ed...

Embarrassing Panties & Garter Belt

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Back in the 60's every young girl couldn't wait until she turned sixteen to have her "Sweet Sixteen" birthday party because that was the advent of her becoming a young woman. Going to a Catholic grade school until eight-grade I had to wear uniforms with knee socks to school and my parents forbid me to wear stockings out socially, remember pantyhose weren't invented yet. So when I turned sixteen I was ready for some wardrobe changes. Vividly I remember that morning of my sixteenth birthday taking a bath to get ready for my afternoon party and as I walked out...

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Tags: humiliation, nylon, older-woman

Enema on the Farm

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We lived on a farm way out in the country where there were not too many visitors and, because our house was set well back from the seldom-traveled road, we had had a lot of privacy. I can remember, when we were preschool and even in the pre-teens, on hot summer days, instead of bathing in the hot bathroom, my two sisters and I would wash up outside, soaping ourselves and then using the garden hose to rinse. We didn't feel too self-conscious about our bodies because we had seen each other nude so often, it really didn't seem unusual....

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Tags: enema, older-woman

Diane And The Lawn Boy

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*** Diane is an attractive older woman with a bit of a problem. She is extremely sexual but she is attracted to young boys. (Fb, ped, voy, oral) *** Diane was lying in her tub with the water pick gently spraying her open cunt. She was older but still good looking and was thinking of her last young boy. She knew that young boys had powerful hormones and, if you didn't scare them away, they were fucking machines. She was lonely now that the pizza delivery boy had moved. Her orgasm was getting closer as she remembered his hard young...

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Tags: older-woman