older woman sex stories – Page 10

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...

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...

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...

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...

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...

Mrs. Tillman’s Closet

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When I was 14 years old my neighbor Mrs. Tillman asked me to come over and help her move some boxes in her closet. I had always had the hots for Mrs. Tillman because she was a very attractive woman. She was and around forty-eight years old, about 5'10 with auburn hair. She had a big fat ass with wide hips, and a nice set of plump tits that I would have loved to stick my face in forever. When I got to her house that day she was wearing a short blue skirt and a sweatshirt. "Thanks for coming...

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

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...

My Aunt & Her Bedroom

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Growing up in the Midwest, I always loved visits with my Aunt Bonnie. She was so different from my step-mother and my father. So open, so loving, even to a nephew who wasn't related to her by blood. She also lived on the west side of town, so I got to see things and places with her that I didn't see as a north sider. Things that may have reminded me of my first five years, living on the west side. More than anything else, Bonnie was beautiful. As a boy, I really didn't notice that as much as how...

My Aunt Fatima and Me

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I had started masturbating at an early age of 14. Mostly I used to imagine and fantasize about newly married couples whom I knew from my known circles and relatives. As I grew older then it was at times some teachers in my school. Somehow I always fantasized about older than me women and never my age or young females and probably this had been the reason for my obsession for older women. When I was 18, I happened to visit my uncle/aunt in a nearby town and had to live there for 2-3 days to complete some work which...

Mother in Law Visit

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My Mother in Law has been divorced for 3 years now and she works in the school system out of state. Anyway, my wife wanted her Mom to visit for a week during the Holidays so we bought her a plane ticket and she came to visit for 10 days! Now, the MIL is 16 years older than my wife, is a couple inches shorter and only has B cup breasts, compared to my wife's D cups. Yes, I looked through MIL underwear,,,sniff, sniff...LOL. For a woman in her late 40's she still looks hot in tight jeans and a...

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Tags: older-woman

Mother’s Friend

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As I have read the stories on this board I can't help but see myself in many of these situations. My modus operandi is like many where it appears to be accidental or that I am not aware of the woman watching and voyeuring me. It is less threatening and to some degree I hope that the woman/women enjoyed it. I learned from an early age from the previous posting about my mother's friend that it allowed her not to look at me so much as a pervert but that she somehow always caught me with my shorts down....

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Tags: masturbating, masturbation, older-woman

Mrs. Alison Jenkins

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Mrs Alison Jenkins part 1 It had only been two weeks since Steve, my husband had gone to work in Australia for a whole year. Already I missed him and hated living on my own. We had only been married for a few months and moved several hundred miles away from my parents because of his stupid job and now I was stuck here alone. To be fair the small village in North Yorkshire was lovely and unlike London where I grew up everyone was very friendly even if they did consider us both to be “posh southerners”. We had...

Mrs. Cassaway

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We lived in a neighborhood just like you see in the movies with trees overhanging the streets, kids playing in their yards and people mowing their lawns. We lived right in the middle of the block with a nice 2 story house that my mother just adored. I was around 15 I think when this all took place .....its an amazing story which I cannot keep to myself any longer. It was the day after school had let out for summer and we had only been in the neighborhood for about 6 months or so. Our next door...

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Tags: anal, anus, hosiery, masturbate, nylon, older-woman, rectal, rectum

Mrs. Gosden (part 1)

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As anyone who has been reading my recent postings will know my ideal woman is voluptuous, well endowed and totally uninhibited sexually.. Although my current girlfriend, Trudy is a little younger than me I have over the years found that these attributes are more frequently found in more mature women. It has been my experience that for the most part that they have less inhibitions and are more skilled at taking care of a young man's sexual needs. In my mind an older woman's body if kept in good shape is many times more erotic than that of a younger...

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

Mrs. Janson

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I was raised in your standard white bread family, my parents are still married after 42 years, still happy together, my brothers and sisters, ( I have 2 of each ) are happily married, raising families of their own. I am the only one still single at the young age of 23, and not looking for a permanent relationship as of yet. I was laying in bed a few nights ago reminiscing on how I learned about sex, and it sure brought back some fond memories of my first real woman. I had been cutting yards for years for the...

Mrs. Michaels

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I was unemployed, back at home, and staying in my old room. I hadn't been in the old neighborhood in about six years. It is funny how old memories and habits come back. I remember staying up late messing around on the 8088 computer that I had and then sleeping in until noon the next day. The computer has changed but the times are about the same. I rolled out of bed and was heading down the hall towards the bathroom when I happened to glance out the window that overlooked our backyard and the neighboring yard. I stopped suddenly...

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Tags: areola, big-breasts, huge-tits, mom, mommy, mother, mother-son, older-woman

Mrs. Moon (part 1)

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I had known Mrs. Moon since I was probably about 10 years old. The Moon family moved into the town next to ours a couple years after we moved into our town. They had 2 children - a son about 3 years older than me and a daughter who was my age. Even though we lived about a 10 minute drive away, we didn't do family things that often, probably once a month. I even dated the daughter once when I was 12. It was funny. I asked her to go to a movie with me, but I didn't...

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Tags: older-woman

Mrs. Robinson’s Panties

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My mother used to send me up the street to help a single mom with chores around the house. At first I hated it. Then I discovered her lingerie in the laundry and started trying it on. She never found out, but I often fantasize that she did. This is one such fantasy. Mrs. Robinson was like a little sister to my mother. I wasn't even sure how they'd first met, but she was always around when I was growing up. When I was in junior high she'd gotten married and bought a house just up the street from my...

Mom’s Yellow Panties

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The fact of the matter is that all women's underwear is sexy. But, normally, it seems as though black or red panties are talked about the most often as being erotic. When I think of sexy panties there is another color that can be equally stimulating. One might think of sun bathing under the hot yellow sun or picking pretty yellow daisies. You might even think of the sour taste of lemons. But, yellow is also the color of warning. Don't cross the yellow line on the street or run a yellow light or you could be asking for more...