older woman sex stories – Page 10

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 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 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...

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...

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...

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

Mother in Law Fun

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This is a second encounter with my mother in law. Again, she is an older Latina woman with nice big breasts and a big butt to go with it. We usually meet on Sundays for brunch at a restaurant by our houses. It has been several months since our swimming pool encounter and we have never had much time together since then. I was always nervous that she would tell my father in law or my wife of our encounter or something to let the cat out of the bag. Every time I see her I am usually checking her...

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Tags: masturbate, masturbation, older-woman

Mother-in-Law Stripped Naked

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Chapter 1 Incest is not for everyone and there are some who believe that the term incest only applies to sexual contact between blood relatives and not in-laws. Still, whether it is considered incest between in-laws or not, all will agree that sex between in-laws is taboo, forbidden, discouraged, frowned upon and never openly discussed. Yet those who are excited by the thought of bedding their mother-in-law, father-in-law, sister-in-law or brother-in-law may enjoy reading about what happened to me and my mother-in-law some years ago. My mother-in-law's ideals were as solid as her morals, but she liked to drink and...