older woman sex stories – Page 16

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...

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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Tags: masturbate, masturbation, older-woman

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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Tags: medical, older-woman

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...

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...

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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Tags: big-breasts, huge-tits, masturbate, older-woman

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...

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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Tags: aunt-nephew, nightgown, nylon, older-woman

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...

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Tags: older-woman

Brighton Bed and Breakfast

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I don't know if any of you have visited a seaside bed n breakfast in the UK before, but they're pretty grim affairs. I spent some time traveling around the south coast of England a few years back, so I saw a lot of them, spent a lot of time staying in them, and I know whereof I speak. Your typical English coastal B&B is a narrow three to five storey Victorian building within one or two blocks of the beach. They tend to be crammed together in rows, with no gaps between the buildings. Formerly houses for the rich,...

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Tags: grandma, grandmother, grandson, granny, nightgown, older-woman

Bunkmates

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Even at an early age I was fascinated by pantyhose. The silky sheen and the soft feeling of nylon never failed to get me excited. Whenever I saw a woman wearing them I would stare at her silky legs and try to sneak peeks up her skirt or dress, becoming instantly aroused even by the slightest flash of control tops. I fantasized about them constantly and would sometimes even sneak into my mom’s or my sister’s underwear drawers just to get a close look at the mysterious fabric that had such a hold over me. Then one day my aunt...

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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Tags: masturbation, nylon, older-woman

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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Tags: big-breasts, huge-tits, older-woman

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...

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...

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...

BBW Stepmom

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It seems I always had this thing for bigger, full figure women. I don't know where is started but I seemed to fantasize about them all the time. My step mom was a bigger woman. My dad divorced and remarried when I was very young. He was away quite a lot with business so it was just me and Sally, that's my stepmom, at home most times. I always thought Sally was quite attractive even when I was young. As I grew older I started to notice her more. She had put on a few more pounds over time...

Be Careful What You Wish For

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Chapter I: Kevin's Shameful Secret As Kevin awoke, the large black nylon panties over his head and face instantly reminded him of the previous nights activities. His right hand instinctively reached down to fondle himself through the silky confines of the pink nylon women's panties he was wearing; as his left hand began to rub the shiney satin cup of the white padded bra that was secured around his chest. His excitement increased upon feeling the stiff nylon of his cum stained panties, as he remembered last nights hour long conversation with his strict telephone dominitrix, Mistress Dawn. Kevin began...

Best Friends Mom

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From the age of 6 to 18, I lived a couple of doors from my best friend. His dad was a doctor and worked long hours, and when he wasn't working, he was on the golf course. My friend was an only child. His mom was about 28 when he was born, and she took great care of herself. I've posted stuff about her before. This thread reminds me of several times where she'd do housework in the sheerest of nightgowns. Of course, only around me, my friend and one other boy. Never around us when her husband or our...

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Tags: anal, anus, doctor, medical, nightgown, nightie, older-woman, rectal, rectum

Bev’s Massage

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My cell phone wouldn't stop ringing, but I had no time to take any calls as we made our way up to her doctor's clinic. Bev had called me at work, and when she told me she had fallen, I dropped everything and rushed to her home. Normally Bev would call my wife for something like this, but Kate had been out of town for 3 days and was not due back for at least another two. Bev wondered if it was Kate trying to ring after I had left the message at her hotel that her mother had fallen...

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