older woman sex stories – Page 15

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

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...

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, aunt-nephew, 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

Dirty Boy

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"Please Samuel, remove your shoes and socks before stepping a single foot in here," Bethany Cannony said to young Sam very matter-of-factly, "we are going into the nicest room in my home you know." As they stepped through the arched doorway, Sam felt very out of place in what was clearly the tidiest and most elegant room he had ever set foot into in his young life. His bare feet sunk into the lush white carpeting as they made their way past the expensive decorative lamps perched upon antique marble tabletops. Delicate glass menagerie hung from display stands on delicate...

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Tags: doctor, humiliation, medical, older-woman

Doctor Laura’s Procedure

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Laura slipped on her white doctor's lab coat and she stood and looked at herself in the office mirror. She was just barely five foot tall more like four foot eleven. She had short professionally cut blonde hair and bright blue eyes. She wore a nice color of red lipstick that didn't scream tramp but did make a man take notice of how full they were. She looked down at the rest of her ensemble, she wore a skirt that came about two inches above her knee with nice black high-heel shoes, and a light pink top with a neckline...

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...

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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,...

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

Caught by Mom and My Aunt

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Mom and dad divorced when I was about ten, it wasn’t a very amicable divorce, so when everything was finalised me and mom ended up living in a small 2 bed apartment near town, and I only got to see my dad about once a month, and on birthdays and holidays. About six months after we moved in to our apartment Aunt Paula moved in with us, to help mom out. For the last five years she shared a room with mom, so I could have my own room. I recently discovered she’s not really my aunt, and being only...

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Tags: nylon, older-woman, punishment

Caught by my Aunt

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It was the summer of 1978 or '79. My parents had gone had gone out of town for several weeks and I wasn't considered old enough to be alone. My younger brother was sent to my grandparents. In the meantime, they sent me to stay with my aunt and uncle including cousins. Melissa, was 2 years my senior while Sherry was the youngest, a year younger than me. My aunt and uncle lived on a farm which was very different from our sub-division where we lived. My uncle worked mostly during the days so we didn't see much of him....

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Tags: aunt-nephew, nightgown, nightie, older-woman, spank, spanking

Getting Caught in Mom’s Underwear

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Anonymous 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 was so tense it took me an hour to calm down from the adrenaline rush....

Caught Peeking

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Kent quietly stepped up to the teacher’s desk and handed Miss Taylor his paper. She nodded quickly as she took it, mouthing a quick thank you. As she turned in her seat she quietly said, “If you’ll wait I’ll go ahead and grade this.” “Yes ma’am,” the young man said. He shifted slightly as she laid her answer sheet next to his paper and began to check his answers. Kent wasn’t that eager to see what he would score on the test but he was glad Miss Taylor had decided to grade it while he stood there. He had a...