older woman younger man sex stories

Older and Naughty

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I was visiting my grandmother in her rest home a few months ago. I chatted with her as usual and enjoyed her company. She needed to go to an appointment across the facility but wanted to keep visiting with me when she returned. I agreed to wait on her and proceeded to nap on her apartment couch. While I was napping I got the hugest boner and I began to touch my cock, slowly pulling it and massaging it. Grandma's roommate Annabelle had an adjoining room that opened near to the couch where I napped and stroked myself. Annabelle had...

Full Service Landlady

4/5 - (1 vote)

I have often pondered the manner in which society has changed in its view of sexual relations over my lifetime. It is now quite accepted that older people, for example grandparents, still enjoy sex. It has not always been that way. There is no doubt that Grandparents used to to do it back then, but it was simply not acknowledged. Today of course, one could make a date with a grandparent online and be screwing that evening. I learned about mature sex from an older woman when I was about 21 years old. They say that men’s brains differ from...

Helping and Seducing Granny

3/5 - (1 vote)

Every week I go over to my grandmother's house to mow the lawn and generally fix up and clean up her yard. She tells me how much she appreciates the help, now that her husband is gone. One day this summer I learned just exactly how much she appreciated me! I walked into her kitchen that afternoon all sweaty, and drank a glass of lemonade she made for me. She noticed how hot and tired I was and made me sit in the kitchen while she fixed me a snack. I sat and watched my grandmother move around the kitchen,...

My Mom’s Old Friend from College Comes to Stay with Us

5/5 - (1 vote)

My Mom’s old friend from college comes to stay with us I was just waking up, after a long night of studying. I could hear my Mom, yell something down the stairs. I rolled out of bed. I barely got a pair of boxers on and a t-shirt before my Mom opened my bed room door. “Morning.” She said. I smiled. My hands were in my lap, covering my morning wood. “Hey!” I said. “I’m running late for work. I should be home on time tonight. Don’t forget my best friend from college is coming for a visit.” Said my...

Buttfun

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Back when I was in high school I met a 30 year old women that changed the way I thought about sex. I am now 33 and practice what she taught me and look for those things in a women today. Her name was Doe and I met her in one of those bars where, when you are underage, it's easy to get into. And I was underage. The legal limit was 21. I was playing pool and she just walked over and grabbed the front of my crotch. I was surprised and a bit embarrassed. I was 18 years...

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Tags: anal, older-woman-younger-man, pegging, strap-on

Obsession with Granny & Old Ladies part 1

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A story of a teenage boy who discovers the joy of grannies lingerie and panties that leads to a life long obsession. It all began one summer vacation I was staying with my grandparents for a weeks holiday by the seaside. They were both 70 years old but still very fit and active as they had always been sporty people playing tennis regularly. They lived in a large old house with lots of rooms it was like a maze and I found it really exciting as I could go off and get lost in the place while exploring all the...

A Visit to the Doctor’s

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Six months shy of my eighteenth birthday, my father was killed while writing a citation for speeding on I-294. He was a state trooper, the drunk driver was found guilty and sentenced to thirty years in jail. Four days before my birthday, my mother and I moved due to her being transferred. She got a well deserved promotion to chief analytics officer for one of the top educational institutions in the country. After getting settled in our new home, she found a doctor and made an appointment for herself and one for me. I told her that I would feel...

Mama Bear

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A few sprays of cologne and I felt ready to go. I was dressed rather nicely, wearing some designer jeans, a nice, buttoned shirt, and a blazer. I wasn't on my way to a wild party, or a date with a hot chick; I was having dinner with my neighbor, Mrs. Holt. I lived with my widowed father in a nice neighborhood. My dad was a vice president at this big pharmaceutical company, which meant he was either working at his office, or wining and dining people for work. Thankfully, his huge paycheck meant that I wanted for nothing. Still,...

Jamie and Mrs. Gray

5/5 - (1 vote)

I'd been renting a room from Mrs. Gray for almost 4 months. She was an older lady, a divorcee who looked similar to my mother in many ways. They were both tall, almost a full head taller than I stood. They were both sturdily built with broad shoulders, big boobs, wide hips, and thick thighs. And like my mother, they were both kind, but strict at the same time and could become firm if the need arose. Affectionate is not a word I'd choose to describe either of them. Even more, Mrs. Gray never liked to repeat herself or be...

Giving My Widowed Neighbor Some Horny Shows

2.5/5 - (2 votes)

I live in a single level ranch, and I got this office where I keep the computer, and where I masturbate quite a lot. I have a tv/vcr in here, too, where I watch porn sometimes. The windows in here are different, in that they are very high. I like them. They're good for having privacy inside the room from people walking by, and from houses across the street. I love to get completely naked, sit in this comfortable office chair, and masturbate for... hell, sometimes a couple hours while watching some porn, or just checking out some web sites....

She’s Moving Away – 2

5/5 - (1 vote)

*** Further adventures with my sweet, older, well endowed, married neighbor, Marilyn. What a sweet, innocent hottie. What a remarkable Fuck Toy. (MF) *** A short while back I wrote a story I called, She's Moving Away, that you may have read on this website, about the incredible, serendipitous, sexual adventure I had with a sweet, neighbor lady named Marilyn. Sweet Marilyn is an older woman on whom I've always had a crush. For years I would secretly gaze at her, from my house, as she worked in her yard and often fantasized various erotic scenarios that included the two...

A Computer Nerd Gets Lucky

5/5 - (1 vote)

I had always been a bit of a nerd and being a dab hand with a computer just confirmed it. The school year had finished and I had six weeks to kill before Six Form College started. I was eager to get out and earn some money; with there just being mom and me, things were a bit tight at home. Therefore, I decided that it was time I went out and earned my keep. I was always fixing computers for my school friends, and it was one of them that suggested that I try to make a few pounds...

The Seduction of Aunt Jodi

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John just turned eighteen and it being the start of summer he was home reading the want ads cause he still didn't have a summer job. His mom and dad both just left for work and he was sitting at the kitchen table wearing only his jockey shorts. His tanned fit body had matured quite a bit since puberty and he worked out all the time. John liked the looks he got from all the females at the beach or the gym where he spent most of his time. He always was able to seduce some young fox into sharing...

Thawing the In-Law

5/5 - (1 vote)

I was lucky I got a job, but it was in the city, 400 mile from the little bush town where we lived. Still, it would be a welcome break. We, I mean my wife and I lived with her Mother since we were married. This wasn't a bad thing, except for one aspect, her Mother was not accepting of her daughter's wanton abandon the bedroom. When we were first married, she walked in on us several times while we were having sex. I didn't mind, in fact it was a bit of a turn on for me; having my...

Proper Placement

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Agnes, my mother-in-law looked at me, an exasperated look on her face. "What is wrong with you?" She snapped. "Am I asking the impossible, or what? Is it too much that I ask a simple little favor?" "Oh c'mon, Agnes." I argued. "Jesus! Where do you get the idea that it's such a simple goddam favor, eh? I'm thinking that.." "Stop that profanity!" She said firmly. "I'm not religious, but I won't have you talking to me like that. A little respect if you please!" I modified my voice. "I'm sorry Agnes. You know I respect you. But this is...

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...

My Middle Aged Neighbor Lady

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My moms best friend lived right next door to us for many years and was probably one of the most uninhibited people I've ever known in my life. She was what I always considered to be a very attractive petite Cuban woman with pretty well done gray hair, a curvy set of hips and a very nice set of big tits for her size. She would walk around without a bra, and her boobs bouncing and barely covered. My brother and I loved when she came to see my mom cause we almost always got a free peep show. I...

My Insane Granny

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If you are looking for an unususl sex story then this one is for you. My name is Raj and I am from Chandigarh. I was an only son of my parents. My father worked as cashier in a small hotel. I was in tenth standard When my mother died. After that I lived with my father but just after three years he met with an accident and died. I was compelled to leave my studies and start working. My job was that of a sales agent who books orders from the shops. This enabled me to adjust my timing...

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 Aunt Watched Me

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I have always loved my aunt. I've always found her pretty and sexy. She is about ten years older than me. When I was 38 I confided in her that I found her extremely sexy and I thought about her often. She was very surprised to hear this, but she smiled warmly at me and gave me a warm hug. Maybe a month later, one day we were talking on the phone and I asked her over. It was in the middle of the afternoon and she had nothing to do so she came over to visit. We sat in...