older woman younger man sex stories

Ms. Demeter

3/5 - (1 vote)

Still living at home with my parents at 21 was not exactly ideal. Even less ideal was the fact that I was still a virgin. I was working hard to save up money and move out by working shifts in a warehouse, lugging boxes around. It was laborious, boring work but it came with two advantages. Firstly, the physical effort was good exercise, keeping me fit and toned, meaning I didn't have to waste money going to a gym, and even if I wasn't proud of much in life, I was at least happy with my own body. And secondly,...

Naughty Mature Lady

4/5 - (1 vote)

Mary was in her late sixties and I'd been working for her for quite some time. She was a very friendly lady, and I often had a cuppa with her in her kitchen. One day, I’d started a bit earlier than usual and gave a knock on the door to let her know I was there. She answered the door in her dressing gown. “You’re early,” she said, “I’m not even dressed yet.” I apologized and offered to come back later. “Don't be silly," she replied, "you are still welcome to come in for a cuppa if you like." “Well,...

Grandma’s Best Friend

5/5 - (1 vote)

When my wife Chloe and I were in college we often got together with her family, most of whom lived in the same city. We were in our mid-twenties and in really good physical shape when this happened. It was Saturday and we were invited to visit Chloe's grandmother. When we arrived the usual family members were gathered. This time, though, Chloe's grandmother had invited an old friend of hers. When I introduced myself to her I noticed that she was still attractive for a lady who must have been in her late sixties. She was in decent shape...

A Model Mom

5/5 - (1 vote)

Finally after a long day of work at the office I was home. I had to work overtime today to finish up some paperwork for Dr. Crunell but now looked forward to a nice relaxing weekend at home. I walked into the house “Mikey you still awake?” No answer At thirteen years old my son didn’t really have much of a social life; I mean what kid goes to sleep at 10:00 pm on a Friday night? Aw well, I didn’t really blame him, ever since my husband and I broke up last year he really hadn’t been the same....

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...