older woman sex stories

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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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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Confessions of a Panty Slave

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There are several kinds of boys in this world: those who have masturbated to their sister's panties, those who say they haven't but are lying about it, those without sisters, and those who are sexually dead. I am a member of the rather large first kind. I grew up in the 1950's we didn't have internet then. As a young pre-teen, the best I could do was the girl's section of mom's Sears Catalogue and at least they showed pictures of women and girls in their undergarments. I didn't have a lot of time alone in the house (mom was...

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Crazy Handjob

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Back when I was about 13 I started developing quite well for a boy my age and at this age I was already 5'6 and a firm, sturdy 140 lbs. But the biggest change to me was in my cock. I was a solid 8 1/4 hard and quite wide with a large purple head. Guys at school soon noticed and gave me mean nicknames like donkey dong or pipeline Pete. I never gave much thought to my cock size until I noticed girls and even older women staring at my package during the summer between my 12-13th years. I...

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Cumming in Front of Older Ladies

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A few things before I begin. Noelana (I call her Noe) is a lady I've known for about 7 years. She's 46 but usually acts 26, and rents a house from my uncle. She's about average for her age, if not a bit plump(she's had 2 kids). Over the years I've gotten to know her and her best friend, Lana(I think she's a few years younger than Noe, slightly plumper with a waaay bigger ass), pretty well over the years. We've got an open relationship in that we talk about everything, and can ask each other almost anything. Noe's been...

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Curious Boy, Concerned Mother, Seductive Aunt

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While fantasy, this story does contain some truths. And they were: Mother knew all about her son's 'deep, dark secret'. Unwilling to confront him, she turned that unpleasant chore over to her younger sister. Elaine, a three-time divorcee was well versed in the proverbial facts of life. She agreed to help her older sister in this most delicate task. However, after a short discussion with her nephew she concluded that this deep, dark secret was in fact an irreversible life-style decision that was quite harmless. In her opinion, she saw nothing wrong with it. Indeed, he had an open invitation...

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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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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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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. From then on, I had...

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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...

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Caught Red-handed and Punished

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When I was a teenager, I spent a lot of time alone. I was an only child and my parents were rich and in show business and travelled a lot, frequently being gone for weeks and sometimes months at a time. They never seemed to want to take me with them in their travels, explaining that it would interfere with my schooling, so they left me home with a succession of housekeepers who lived in the house and hired other help to cook and clean. I was kind of a strange, geeky kid and didn't have many friends, so I...

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Charlie’s Grandma

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Every summer I used to go swimming at a friends home. We've known each other all our lives and walked in and out of their home without any worries. Since they had a pool we used to hang in the basement, change and run outside. One summer afternoon I walked into the basement and started to change, I did not notice that there were some suitcases and proceeded to get naked. My friends were outside swimming and I noticed that Cindy was there. I walked to the window and peeked out staring at her hot body. With one hand on...

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Chubby Granny

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This is a true story about my affair with an older woman. It happened in 2017. It's not 100% accurate because I don't remember everything but it is real. A little about Val. She was 60 when things started with us. She is about 5 feet 2 inches and has a nice big ass, both wide and out there, with some nice big tits too. Val is a chubby grandma and even has a great grandkid. She is divorced and has been single for about 16 years. She lived with her mother for the last 12 years or so (or...

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Come in Mommy

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The story that follows is true though I've changed a few key facts (namely the town I live in) to hide my identity. I feel an occasional twinge of guilt, but by and large, I'm pretty damn well pleased with myself. And so is my son! I'm a thirty-two year old mother of one son. John is sixteen. It doesn't take a mathematical genius to figure out that I got myself knocked up when I wasn't quite 16. I dropped out of school and, except for some early help from my parents, I raised John all by myself. Between working...

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Black Slips

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I have been sexually turned on by women in slips, and woman's underwear, since I was very young. And yes I agree with most of you out there that it is a great pity that young women these days do not consider slips to be part of every day dress as once it was considered to be. My earliest memory of this fetish for myself was when I used to go through my mother's drawers to see what she would wear under her clothes, at this time my mother was thirty five, and I suppose quite attractive. I remember that...

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Bobby

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*** A boy receives his first mind-numbing orgasm when a teasing older woman drives him over the edge. *** Nancy Wilkerns was the object of lust for many of the young neighborhood boys. She was a 42-year-old mother of one and a stunning beauty. She aged quite well, partially due to her adherence to a good diet, exercise and remaining very sexually active with her husband. The last extended to times even when her son had friends over for the night. This is where Bobby Vanner had his first sexual awakening. He lay in his friend Mike's room, slowly stroking...

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Boy Magnets

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I am the last teacher in the world I would expect to sleep with one of her students. I am good-looking, I have had plenty of boyfriends, and have never been what I would consider some kind of slut. This is what happened to me last spring. Names changed to protect the guilty. I have been a teacher at Andrew Jackson Middle School for over six years. Bobby Hunter was just an average 13 year old kid in my fourth period class. About 5'6", dark hair, blue eyes, average build. I never looked at him twice, or any of the...

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Brenda & Son

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Hello, my name is Brenda, and I’m a little older, a little overweight, and a little bit dumb. This all started when I was about 29 yrs old and I didn't catch on till I was 45. I am a mother of two, and I like to think I’m pretty fair when it comes to raising my kids. Now, like most woman my age, I like to be comfortable when I’m around the house, and I’ve never had a problem with my kids seeing me in a night shirt or nightgown, or even nude if they happened to walk in...

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Brian’s Directoire Knickers Discipline

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It was in the early 50’s when I was at secondary school and my cousin Sheila was at grammar school, that we two cousins used to visit each other and have fun times during our school holidays. I loved to watch Sheila and her friends doing their handstands against a wall. Sheila usually tucked her skirt into the waist-elastic of her knickers when she was doing this and gave us all a good, long look at her gorgeous knickers. The girls’ knickers of the early fifties were rather like adult women’s directoire knickers. However, instead of the lovely, long knicker-legs...

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Briefs Story

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Many stories involving lingerie are fantasy and this one is no exception. It would be interesting to know how many of us would be interested in a fantasy like this and if it was possible, how many would fulfill it. This is a story involving a lady who has always had a desire to own a special pair of briefs, ones she has personally designed and with a very unique material. Julia had worked at JC Penney for the past five years, she had worked in several different areas including shoes, childrens clothing and even mens clothing but her favorite...

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