older woman boy sex stories

I Sucked My Grandmother’s Tit While She was Sleeping

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4 average (1 rating(s))

Took the forbidden fruit from the forbidden tree. It was one Friday evening when my grandma, Ellie, came to visit us. She would do that often, dine with us, talk a lot, and then spend the night here. It was an evening like any other. We eat, watch TV, talking about different things. But what happened after, changed all. It was late so everyone had gone to sleep. My grandma slept on the couch, as usual. I got to my room and played some games for an hour or so then I felt thirsty so I went to the kitchen....

I Babysat a Teenage Boy and Gave Him A Biology Lesson

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5 average (1 rating(s))

The story of Jasmine, a sexually frustrated woman making a sweet young boy named Flin cum on her sweet juicy thighs. I had always been a very sexual woman. Since my teenage years, I had explored many fantasies and been with multiple men. But after moving to this new city, I had calmed down...until now.I needed money, so I took a job as a babysitter for a rich family in a luxurious penthouse. Their only child was Flin, a 14-year-old boy, short, baby-faced, with soft hazel eyes and an extremely innocent personality. When his parents left for a three-day vacation,...

Aunt Peg

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Chapter One (of two) Looking at my mother and her younger sister, it was hard to imagine that they were separated in age by ten years. My aunt, recently divorced from her very successful and work-addicted attorney husband, was an exceptionally youthful-appearing 34-years-old woman. My mother, soon to be 44, had the same tawny hair and blue eyes, the same slim feminine figure, toned by tennis and aerobics. The family resemblance was striking. That they were sisters was not questioned, but that they were ten-years apart was remarkable. We'd picked up Aunt Peg at the United Terminal at SFO this...

Adventures with Older Ladies (chapter 2)

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5 average (1 rating(s))

The rest of my week seemed to fly past in a blur. I found it hard to concentrate on anything as my head kept going back to Mary and her big tits. It was nice to have a real mental image to go back to. On Sunday morning, I had breakfast and then took a shower. To make sure that any sexual experience that may happen today with Mary would last as long as possible, I decided to toss myself off in the shower. My morning wank that day was different; every other wank in my life had been wanking...

Adventures with Older Ladies (chapter 1)

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5 average (1 rating(s))

I will always remember my first time. Well, let’s be honest guys don’t we all, that moment when you stop being a boy and become a man? Well, this story is all about my first time and the education I was given by some amazing ladies. So first, let me paint you a picture of myself. I was basically your boringly average, simple teenager, into sports and music. The school I went to was mixed gender, so I knew plenty of girls, but I was far too shy to chat any of them up. At our school, the boys hung...

He Needed it Really Bad

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3 average (1 rating(s))

He was an only child living with his lovely voluptuous mother. Having entered puberty some years earlier than most, his hormones were like a raging river. His lust for his mother could not be overcome. He executed a plan that did not turn out quite as he expected. As an only child living with his mom, they were very close. But he had entered puberty very early in life and his hormones were like a raging river. At every chance he got he would take out his magnificent member and spill his copious cream. He could not resist the temptation...

Timmy

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"I'm sorry Timmy, I know it's only your first day here, but I have to punish you!" Claire Markham, Timmy's aunt, was mopping up the milk from the table, looking at the young ten year old sitting on a wooden stool, an empty glass in his hands. Timmy had only arrived at the station a few hours before, clutching a small bag containing everything he owned in the world. His aunt still couldn't understand why such a beautiful boy hadn't been adopted years ago. His large blue eyes peeped out from under a shock of blond curls. Her words took...

The Boy Next Door

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I live in the country & live alone so it is easy for me to just strip off & go skinny dippin anytime I like. And I usually do as often as possible. Lately I feel that I am being watched so I cautiously look around when I am swimming. I saw the culprit late the other evening. It is the boy next door. My neighbors aren't that close so his intentions were to come observe me when he didn't think I would catch on to what he was doing. I pretended not to notice him. He was standing behind...

Bath Time at the Farm

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3 average (3 rating(s))

When I was 16 years old my parents sent me back to the old country to spend some time with my relatives. A distant cousin of mine had a small vineyard and peach orchard on the mountain not far from there home in town. The mountain where many people had small farms or orchards was on the outskirt of town. I gladly voluntered to help that summer as it was a new experience for me and I enjoyed their company. The first week I went up when this woman her husband, their daughter-in-law and another older woman who was...

Hot Massage for a Hot Mom

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My name is David, and I am 14 years old. And I live alone with my 30-year-old Mom. My Dad accidentally got my Mom pregnant, so they decided to get married. From what my Mom tells me, my Dad was a loving and proud father, but he passed away when I was a baby, leaving my Mother as my sole parent. She did the best she could, but her job as an elementary school teacher didn’t provide much for us. We made due, though. We bought a one-bedroom rancher out in the country; it was small, but we liked to...

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Tags: big-breasts, incest, massage, mom-son, older-woman-boy

Mom Taught Me to Fuck with Grandma

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5 average (1 rating(s))

My name is Kevin. I’m 12 years old and I’m the only child to a 38-year-old single mom. My mom is single because my dad died 2 years ago when I was 10. I’ve been having regular sex with my grandmother, who is 73 years old. Not only does my mom know, she frequently watches. When I was 8 years old, my dad brought his mom to live with us because she was showing early signs of dementia. At the time I didn’t know my mom couldn’t stand her, but realized that after my father died and her true feelings...

Tommy’s Drunk Mother

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Exploring Mrs Miller Note - this story is about two English boys and the drunk mother of one of them. As such you will find a few English phrases as the boys use English expressions and names. For American etc readers: - Mum = Mom, Fanny = cunt Knickers = panties. This story is almost certainly a work of total fiction. I had my first fuck when I was just turned 12. Most guys get their first experiences with their girlfriends the same age but mine was with the mother of a school friend -and he was watching and encouraging...

Mommy and her Baby Boy

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Jack waited on the corner for the car that picked him up every afternoon. As usual, he was impatient and shifted his weight from one leg to the other. He looked through the chain-link fence into the schoolyard which was empty at that time of day, but suddenly turned his head and smiled when he heard the car pull to the curb. The woman quickly got out of the car and almost ran around it to the curb where she took Jack's bag and gave him a peck on the cheek. She then opened the car door for him and...

My Old Grandmother

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3 average (1 rating(s))

When I was young I sometimes went to stay with my grandmother who was in her 70's and who lived with my unmarried Aunt, her daughter. It was a small house and I had to sleep in the same large bed as my grandmother. She would change for bed in the bathroom and wore a very long, modest nightdress buttoned up to her neck and down to her ankles. But I could still clearly see the shape of her body, the swaying of her large saggy breasts and the outline of her nipples as she moved to the bed. One...

When I Was Twelve!

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1 average (1 rating(s))

When I was twelve years old, my parents had been divorced for several years. One day, my mother was in the bathroom when she called me to get her a clean towel from the laundry. I got the towel and went over to the bathroom door. It was opened a crack, so I just pushed it the rest of the way open, and stopped with my mouth open. “I’m…I’m sorry, Mom,” I said. She was sitting on the toilet seat with one foot pulled up and polishing her toenails. She was completely naked. I just stood there and stared at...

A House Full of Women (part 2)

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I sat there on the chair in the laundry room my cock still wet from my Great Grandma's mouth and tongue, a little drop of cum dripping from the slit. I couldn't believe I just had a BJ from the old crone and even more I liked it. Well I guess technically it wasn't a full BJ but she had swallowed my cum and milked me empty. As I thought about it, and the offer the old crone had given me before she left my young cock started to get hard again, and I wrapped my hand around it, then...

Aunt Mary’s Fun Day

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I got my first enema one summer when I was visiting my Aunt Mary. It was a hot September day and I spent the morning working outside for my Aunt. I was having a hard time concentrating as I had been constipated for a week now. I knew my Aunt Mary would be the only one that could make me feel better. After lunch, Aunt Mary asked me if I'd had a bowel movement today. She told me I had to have one today, period. I knew I needed something to help me but had no idea what was...

Grandmom Visits

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Billy was 7 and his older brother Toby was 13. Mom had a job overseas for a year and grandmom would be living with them. Grandmom was a sprightly energetic woman at 58. She had a secret thing for little boys and her pussy just gushed when her daughter asked her to take care of her son's for the year. She loved her grandsons and had lots of nasty fantasies she wanted to act out with them. Even though little Billy said he could bathe on his own, she insisted on bathing him herself. She took him to the bathroom...

Spending the Night at Grandma’s House

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My name is James and at the time of this story I was 13 years old. I was just starting to go through puberty at this time, my voice cracking, hair coming in, but most noticeably, my dick was starting to make sperm. I was always so young and naive and even at this age I didn’t really understand sex like my friends seemed to. I was still just a short little boy, no real muscles or anything. One day after school, my mom dropped me off at my grandma’s house to spend the night. Later in life I realized...

Physical Exam for Football

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I had to get a physical in order to play football at my school, but I got a lot more than a physical. It was 1972, I was 11 years old, and going in the 6th grade. I wanted to play football on the school team and in order to do that, I had to take a physical. Because I didn’t have a regular doctor to go to, my mom just looked one up in the white pages and made the appointment. We arrived at the appointment a few minutes early so my mom could fill out paperwork. While she...