older woman sex stories – Page 10

My Much Older Woman

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I don't know which is more strange, writing this story, or that it actually took place. It's about my mother-in-law. It's about a fantasy that accidentally became a reality. My wife, Chris, and I visit her mother quite often since she's on her own for many years. While the drive to her house is a long one, my wife insists on visiting Kate, who is 74 years old and widowed for many years. She is a pleasant enough, non-engaging dumpling of an elder. Certainly the last kind of woman that I would think about in any sexual way. She goes...

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Tags: nightgown, older-woman, stockings

My Neighbor Peg

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I was the oldest in a family situation that was unique to families of the WWII era. There were four of us but I was seven years older than my next youngest brother. My three younger brothers were born after the war and I happened earlier before my father left for military service during the war. I was a toddler when he left and a big kid when he returned, we never did connect as father and son. I can't say that my parents didn't love me for they always were there to give me a word of encouragement when...

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Tags: doctor, first-time, medical, older-woman, romance, woman-boy

My Neighbor Spies on Me

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I've been turned on by allowing women to see me masturbate ever since I was about 15 and saw my older Sister's hairy pussy by accident one day. She asked me into her room to tell her if she looked nice in a certain pair of jeans. After I had commented, she changed back into the dress she had been wearing. As she pulled the tight jeans down, she pulled her knickers with them by accident and I saw my first pussy. She pulled them up - after letting me look for a second - and said "That wasn't supposed...

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Tags: masturbation, older-woman

My Obsession with Panties

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I've been obsessed with panties from a very early age; probably the first time I noticed the difference between my sisters' silky, lacy undies and my own boring cotton "Tidy Whities." I should probably add here that I have three older sisters, one more beautiful than the other. Mom is rather attractive too; that's where they get it from! Dad left early on, when I was about 10 or 11. When my parents divorced, Mom gathered my sisters and myself and told us things would be different from now on. She said she got a new job and that we...

My Friend’s Son

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*** Her friend Ronda needed a place for her son Ron to stay while finishing his senior year in high school and on into college as her husband was being transferred to another city. Having a nice young son around the house would be nice especially considering that her husband traveled quite often and she was alone. *** Rhonda and I were friends before her son was born. We have not had children of our own, as I could not get pregnant. We consider Ron one of our own and his Mom and Dad were grateful as they both worked...

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

My Life and Hard Times

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by JAS INTRODUCTION"The United States and England are two nations separated by a common language!" or something like that. I don't know who said that but it sounds like either Mark Twain or George Bernard Shaw. They're probably two of the most often quoted writers in the English language after Shakespeare and arguably a lot more humorous. Well, this is another story from England, where in an ideal world ladies wear stockings and use suspenders to hold them up. Here Braces are used by men to hold up their trousers as well as by dentists for straightening teeth. A Fanny...

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Tags: older-woman, stockings

My Formative Years

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I have for some time been writing about a current and ongoing relationship with my partners, 76 year old, Aunty Jean and her daughter Jane. I feel it is time to commit to paper how my attraction for much older women started some 31 years ago when I was 19. Like a lot of young men of that age I was obsessed with girls and sex and spent most of my waking life thinking about and trying to get plenty of the latter. So onto Aunty Elsie my grandmother's cousin. *** Having been brought up in a morally strict household...

My Favorite Aunt Fantasy

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This is a pure fantasy that I developed many years ago and concerns what some might consider incest… this fantasy helped to produce many loads of hand-pumped cum in my early 20’s, and actually came about as the result of a real-life experience. Through high school and my early college years I did some part-time work for an uncle who was in the home remodeling business. During Christmas break of my sophomore year of college he was working on the home of his sister. Since he was my uncle through marriage to my dad’s sister, his sister wasn’t actually my...

My First Encounter with Wonderful Directoire Knickers

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When I was in my last year at school some new neighbours arrived. It was a couple with baby twins, and the wife, who was younger than her farm worker husband, became very friendly with my mother, who used to look after the twins. At that age I was very interested and inquisitive about girls and noticed that as Irene bent over to attend to the twins, her rather short dress rode up at the back. I was intrigued to see the elasticated legs of her white or sometimes pale blue knickers. These knickers were similar to those that my...

My First Exposure (part 1)

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----------------------------------------------- This story is woven around an old friend's fantasy she shared with me over a span of nearly 30 years. ----------------------------------------------- Like a lot of women, I've had some fantasies during my 40+ years, but had never had the opportunity or nerve to live any of them until Mike took me for a fantastic massage last month. I ended up feeling physically great and so very excited that I was nude under my towel as Mike watched another man give me a really professional massage. But the best part was after ... on the ride home and later in...

My First Exposure (part 2)

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"Maybe I can help him get a better look," I thought as I reached for a napkin on the table and "accidentally" dropped it. "I'll get it for you Mrs. Tyler," he said as he bent over to retrieve it. I pretended to look away while he was bent over but saw him turn his head and look up my skirt as he was leaning over. For that moment, I parted my legs and left them open a little longer to give him a clear view of my moist panties. He was so engrossed at looking at them, he had...

My First Exposure (part 3)

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You're looking at my panties again Jimmy. Still curious about what it looks like under there?" "I sure am. Gee, you're almost naked now any way. You might as well let me see you completely naked. Come on Mrs. Tyler, let me see a naked woman for the first time!" He was getting smarter for an innocent kid. Here I was, a 40+ year old woman almost naked in front of a teenage boy and loving every minute of it. But hey, why not. I was enjoying it as much as he was and what could it hurt. Every young...

My Aunt Liz

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From the time that I could remember my Aunt Liz always had a playful demeanor with an edge of sarcasm within her playfulness. When I was just a child and she came over to visit her younger sister (my Mom), she would always take the time out to show me some attention. Generally back then; even though it encompassed some physical touching, the playfulness was wrestling or tickling, or a combination of both. Aunt Lizzie lived in our state's capitol a couple of hours away from us so it wasn't as if we saw her on a regular basis, so...

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Tags: first-time, masturbation, older-woman, tease

My Aunt Sandy

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Part1 My first visit at my aunt's. (age 9) I grew up in a very loving yet strict home. I have an older sister (5 years older) while growing up she was not only my friend but also my protector against bullies and at times my parents. On many occasions she would either cover up for me or talked my parents out of punishing me. She was very wild especially for a girl-- for this reason my parents spend most of the time disciplining her and were more lenient with me. I guess she trained them well because they often...

My Aunt Sharon

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It all started a week ago on a Saturday. I was out with three mates for a few beers and a curry. Later, we went to several clubs in the city centre and I was well wrecked, not picking up any cum sluts, puking in an alley and shaving to stagger home. It was nearly one in the morning when I reached home. I could see downstairs lights on in the trash quality, council house we existed in. That's my Mum and Dad, me and my two sisters Charlene, she's the adopted black one aged sixteen and Karen, who is...

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

My Aunt Violet

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This is a true story of my youth. It’s amazing how life takes its shape. I had the good luck to be able to live out my fantasy with a wonderful lady. My aunt Violet. My aunt Violet was the first real love of my life. I was 18 and reveling in the excitement that older ladies were now causing me. A little while earlier, I had been seduced by my teacher, a Nun. But that’s another story. Violet was a young boy’s dream. Long shoulder-length raven black hair, ruby red lips, a voluptuous, well-rounded figure and a way of...

My Aunt Was The Answer To All My Sexual Desires

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When a boy starts puberty, his curiosity and desire become very strong. He could think of nothing else but sex. Then one day his aunt became the answer to all of his questions and desires. *** Back in 1967 when I was approaching 13 years old, my parents were both killed in a car accident and being left with out a dad and mom, my mother's sister Elsie took me in and continued to look after me. She was 34 years older than me at that time and had been divorced for a number of years. And since she had...

My Big Breasted Cuban Babysitter

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I have a story to tell that involves many years of living next door to one of the hottest and most loving women I have ever had the chance to know. It all started when I was about 11 years old. We lived next door to an older Cuban woman who at the time was in her mid to late fifties who fascinated me with her very large and attractive porcelain colored breasts. When I was about ten I began to get very aroused every time Grace, not her real name, would come over to our house to see my...

My Aunt is Easy to Hypnotize

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*** My parents go on a 6 week holiday while I stay with my sexy aunt June. I find it easy to hypnotize her to get what I want from her. (m/F, inc, 1st, nc, ws, mc) *** PART 1 My parents are leaving in 2 days on a month cruise and a 2 week land tour of Asia but due to a run in I had with a fucking cop I can't get a past port so I am going to stay with my aunt June. I do like June because for one thing she is only 6 years...

Mum and I

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===== CHAPTER 1 I'm writing all of this down on my computer and keeping it in a password-protected document while it's still fresh in my mind. I'm 19 as I write this but the pages I'm taking this from are from my computer diaries which I've kept from the age of 8. They are more like accounts of the things that happened to me using understandably rudimentary language but nevertheless, it's still there and all I have to do is translate it into readable accounts and fill any gaps in with my own memories which are still vivid enough. My...