older woman sex stories – Page 17

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...

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Tags: anal, anus, big-breasts, huge-tits, mommy, older-woman, punishment, rectal, rectum

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...

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

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...

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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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...

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 and...

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

Bible Mom

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I'm going to talk about my mother and her religion in a way that may appear a little dark, depressing and uncomfortable. I think she was a lousy parent but I know I wouldn't be me if it wasn't for her and her mistakes. My mom came from a military family. She was the second youngest and terribly jealous of her younger sister. I think that's why she got married at 18 to Vietnam vet and had me by the time she was 19. Sadly, the marriage was over by the time I was four. I have almost no memories...

Big Evil Auntie

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David had just finished his paper round and was feeling a little tired being small for his 16 years. As he entered the house he saw his Aunt Sheila in the living room sitting on the settee crossed legs showing her ample curves, a woman of 40, strongly built about 5'10" 180 pounds, brown hair tied in a bun. David stared at his Auntie as he entered, she looked up at him her huge breasts jiggled, David's Aunties breasts were at least 49DD, in fact her figure measured a whopping 49DD-33-48, she had a broad but tight waist, broad back...

Big Tits

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Is it a blessing or a curse for a thirteen year-old girl to have huge tits? I was already sporting 34DDs when I entered junior high school. The boys flocked around me, found excuses to rub against my chest, and the bolder ones would even grab at them when they could. It made me uncomfortable as hell. My older sister comforted me and told me I should enjoy the attention, and the power. She said my tits could get me a lot if I wanted, that boys, and even men, would do just about anything I wanted for a chance...

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

A Voyeur’s Dream

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My girlfriend Diane is an exhibitionist and I am the appreciative voyeur. She is forty years old, very attractive, full-figured, and has very large, pendulous breasts. She wears loose fitting, low-cut blouses and tops and bends over in front of her "victims" giving them terrific views of her hanging breasts. She adjusts her bra straps loosely so that her breasts bulge out of the cups and her nipples peek in and out of view when she bends. She also wears denim jumpers and skirts and sits "unladylike" or squats or bends around men and teenage boys, giving them views up...

A Voyeur’s Dream 2

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As I indicated before, there were powerful forces at work when I was a boy that shaped my wants and needs as a man. I stayed with a neighbor lady, Jean, after school. I know now that she was an exhibitionist, but at the time I just thought that I was the luckiest kid around. She was constantly treating me to cock-hardening views down her blouse and up her skirt. I was a horny kid and masturbated furiously and frequently thinking of her and others who I had glimpses and fantasies of. One hot sunny afternoon, I went to Jean's...

Babysitter

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“Mom, do I really need a babysitter? I mean I'm thirteen, after all.” “Probably not, sweetie, but it would make your father and worry less. And besides, don't you think a whole weekend alone in the house would get lonely?” “I guess so. I just wish you guys thought I was more responsible.” “Alright Josh, I tell you what. If you're well behaved for the babysitter and Sam gives your father and I a good report, we'll think about letting you stay home alone next time we go on one of our couple's weekends.” That was seriously good news. My...