older woman sex stories – Page 8

Older Woman Flash

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I had something like that happen to me once. I lived in an apartment building and there was a very nice older woman about 51 years of age that lived down the hall from my apartment. Sometimes I would help her bring things up from her car to her apartment. She always thanked me and would look to see if my dick was showing through my pants. One day she knock on my door and asked me if I would put a new battery in her smoke detector in her apartment. I could tell she had been drinking, hell she...

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Tags: older-woman

Older Woman Nextdoor Hanging Laundry on the Line

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Linda carefully hung the sheets and clothes on the backyard line to dry. Of course she had a clothes dryer but it couldn’t match the fresh smell the summer breeze imparted to the clothes. Besides, hanging the laundry in her backyard was a pleasant, leisurely activity that she enjoyed on these warm mornings. The only sound was the gentle breeze in the trees and the birds singing. At 57, Linda was, as she often told herself, ‘terribly typical’. She was a mom with two grown and married kids, one of whom had recently made her a grandmother. Her very natural...

Older Woman Seduces a Young Man

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This story begins when I was 19. I had moved away to take a job and was living in a totally new state, hundreds of miles away from anything I ever knew. It is hard to meet new people when you’re under 21 since you can’t go to the bar or anything. So I was having a tough time meeting people and was getting quite lonely. Fortunately there was a receptionist where I was working that was always very friendly with me. She was 56 and a short rather chubby woman with huge tits. She would always talk to me...

Oliver’s Aunt

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Sixteen years old Oliver had been invited to his Uncle Jeff and his Aunt Barbara's home in the South Coast of England for two weeks during the school holidays. His parents didn't think he was old enough to go away with his friends yet and so his dad had asked his older brother, Jeff, if it was okay for Oliver to go down to stay as Jeff was on leave from work. Jeff worked two months on and one month off for an oil company in the Middle East. He was forty six years old and his wife Barbara was...

Our Big Neighbor

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We moved right after school was out. My father had been transferred to another city in early June, and it was decided that we would move as soon as possible. Our new house was in the suburbs of a large western city and there was a lot to do. After nearly a week of unpacking and straightening, it was time for me to mow the lawn and trim the overgrown hedges. The hedges separated our yard from our neighbors. I had no idea who lived there. I had never seen anyone. The house was quiet and dark most of the...

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

Out of Mischief

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A spoiled 10-year-old brat of a boy regrets causing trouble in an hotel when he gets an early introduction to strict bondage and humiliation from women who won't tolerate his tantrums. (FFb, ped, nc, mast, bd) *** Bartholemew lay on his stomach, watching daytime TV in a plush, second-floor hotel room. The volume was way louder than necessary, but the 10-year-old didn't care. Bored, he popped another chocolate in his mouth with one hand while he idly flipped channels with the remote in the other. He wondered where Mrs Baxter had got to. He also wondered about that big house...

Neighbor’s Mom in Great Shape

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I am a single guy who is still "playing" the field. I date regularly but I haven't had a steady girlfriend for a couple of years. My next-door neighbors are a married couple my age, Janie and Eric, who are very close friends of mine. We help each other out all the time and hang out a lot. Last summer Janie asked a favor of me. Could I help move some boxes and backs into her apartment that her mom was dropping off? She knew that I had off on Mondays and both she and Eric worked. Her mom and...

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Tags: masturbation, older-woman

Nephew Comes For A Visit

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*** My nephew comes for a visit. During a conversation he tells me that he has a problem when it comes to making sex last. So my wife and I devise a plan to help him out with his problem. (MMF, voy, wife-sharing) *** My sister called one day and asked if my nephew could come and spend some time with us. Her husband had left her years ago and she thought that her son needed some time with me 'an older and wiser man' as she put it. Thanks a lot sis, I love you to. Well Brian was...

Nice Neighbor Lady

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After I graduated from college, I lived in an apartment for about five years. I didn't like living in the apartment because of the lack of privacy, lack of parking, and other little things; so as soon as I could afford it, I bought a small house in the suburbs. The house was located in a safe and well-lit neighborhood. Since it was in a circle drive, there wasn't much traffic. My neighbors were real friendly, and I got to meet all of them. There was one lady who lived two houses down from me who I really liked. She...

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Tags: doctor, medical, mom, mommy, mother, nylon, older-woman, punishment, spank, spanking, stockings

Nighty-Ware

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Prologue It all started when mom had hosted a Nighty-Ware party for some friends and neighbors in my house. Instead of plastic storage containers, lingerie of all kinds was sampled and purchased. My first sexual experiences came as a result of delivering these purchases to our neighbors. Since then, I've had more experiences, heightening and strengthening my attention and desire for sex. Part 1 ______________________________ I guess I was just destined to grow up horny. At least, that's what it feels like in retrospect. I thought about sex all the time. My dad had a...

My Secret World

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Daydreaming about panties is what I do a lot. I daydream when I’m busy or bored, or especially when I’m scared or worried and need something to distract me from those terrors. It began back in grade school when I first discovered how soft and smooth nylon panties felt and how wonderful they looked whenever I got lucky enough to catch a peek at them under a skirt or dress. I have to confess, my first fantasies about panties were centered around imagining ways I might catch a peek at the panties worn by girls at my school. It was...

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Tags: nylon, older-woman

My Step Sisters (part 1)

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My own Mother died when I was eight. For the next five years I lived with my Father. Then, when I was thirteen, my Father met another woman. After a short romance he married her and we moved in to her house. My new Step Mum had three daughters Liz who was fifteen, Jayne who was the same age as me (thirteen) and little Becky who was just eleven. When we moved in my Step Mum told me that I would be subject to the same rules as the girls and...

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Tags: older-woman, punishment, spank, spanking

My Story (How my panty fetish developed)

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(How my panty fetish developed) The day was very hot and I came in from playing just in time to get a bath from my mother. It seems strange to say that, but I was very young at the time, but the events that took place that day altered the rest of my life. After the bath my mother could not find any of my underwear to put on me, so she gave me a pair of my older sister's pink (or peach) rayon panties. I did not want to wear them, but my mother and an aunt that was...

Naked with Aunty

4/5 - (1 vote)

CHAPTER ONE I'm sitting at the keyboard and the white screen disappears and I'm looking back a good twelve years, to the time when I still lived at home while making my way through college. I'm an educator now, but at the time, I used to work late nights at a convenience store. My story is based on actual events, so there is no explosive sex to be found here. On the other hand, I think that those of you who are turned on by the sensuous nature of nudity and nudism will find this story stimulating. The same goes...

Necessary Exposure

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Hayley stood before the mirror, working her brush through yet more tangles in her hair. As the brush pulled free, several drops of water fell from the ends of her hair, dripping onto her shoulder and down her breast. She looked at herself in the mirror. Age 40. Assessment. She wasn't 30 anymore, or even 35. Her breasts sagged a bit, but then, 38C was a mature size. Her skin wasn't quite... well, it was just looking aged. Not old, just older. Not clouded with spots, but not blemish-free either. A stretch line here and there. It didn't bother her....

Neighbor

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One summer day as I finished mowing the lawn I noticed my next door neighbor laying out in her yard on a beach chair. She was about 40 years old and I was only 16 but the thought of actually fucking an older woman turned me on. She had a nice big ass and nicely shaped breasts. As I walked by she called my name "Joe can you come her for a second." "Sure Mrs. Walsh I'll be right over" She was wearing a one-piece bathing suit that was very tight around her big, but not large ass. I couldn't...

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

My Mother’s Friend Showed Me

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Since I was twelve years old, masturbation has become a daily routine for me. My story happened when I was sixteen. By then I was a new student at a boarding-school for boys far from home in the mountains. I was very interested in girls but apart from some petting was not very experienced in sexual matters. My mother was visiting me over the weekend and stayed in a private house of a distant friend who's name was Christine. She was a very good looking woman of 38 years, that was married to a marine captain. My mother asked me...

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Tags: masturbation, older-woman

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

5/5 - (1 vote)

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