older woman boy sex stories

Mom Taught Me to Fuck with Grandma

5/5 - (1 vote)

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

4/5 - (1 vote)

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

4/5 - (1 vote)

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

4/5 - (1 vote)

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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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

4/5 - (1 vote)

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

5/5 - (2 votes)

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...

I Just Need to Examine Your Penis

2.5/5 - (2 votes)

In the 70’s I was at boarding school and the school nurse sexually abused all of us. In the 70’s when I was still little I was sent to an all-boys boarding school where I lived until I was 15, but when I was 12 I and all the other boys were sexually abused by the live-in nurse, but we didn’t know it was sexual abuse until we were adults. Every 2 weeks we had to go and see the school nurse for a health check-up, when we were younger it was just a simple “Take off your shirt.” And...

Mrs. Peters

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"Hi Mrs. Peters, is Rick home?" the young man asked as the very pregnant Mrs. Jane Peters answered the door. "No Kevin he's out with his dad" she said rubbing her swollen belly. "Come on in though, they should be back soon and you can keep a beached whale company." Entering the house the boy replied "Your no beached whale Mrs. Peters" "Well Kevin I certainly feel like one. Only a few more weeks until I deliver and I really can't wait." She said engineering her way onto the love seat. Kevin sat across from the pregnant Mrs. Peters. Before...

Billy and Aunt Karen (part 1)

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At the Restaurant It was mid-afternoon, which gave Billy a few hours to get ready for the evening and the two weeks to come. In thanks for everything, Carl and Karen Stone had been invited to dinner with his parents, and of course, he was invited, too. He knew they were going to a very fancy restaurant, which also meant dressing up appropriately. He thought about what to wear, and then imagined what his Aunt Karen would be wearing. She had such an attractive body, shapely legs, pointed breasts and a narrow waist. For the longest time, he had a...

Billy and Aunt Karen (part 2)

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The Ties That Bind His Aunt Karen was attractive, somewhat independent and ran a household with the efficiency of a military officer. Billy had just turned thirteen, although he still looked more like nine or ten at the time he spent two weeks with Aunt Karen while his mom went with his dad on a business trip. His two older cousins were busy teenagers - more away than home, and she could use the company, or so his uncle had reasoned. His aunt had a very pretty face, a very good figure with pointy breasts and nice legs. And,...

Billy and Aunt Karen (part 6)

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Lingerie Show Two days later, Karen Stone and nephew, Billy had sat at the kitchen table for some time. She was working on the household accounts. They had become quite good friends during his stay. Billy thought she was very attractive, but he knew that at his young age she wasn't attracted to him, however Billy was happy just being around his attractive aunt. He had, however noticed that since the second 'tying-up game, his aunt had at first been a bit standoffish. When he had made a veiled reference to her behavior change, she had immediately begun catering to...

Aunt Mary part 6

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by StockingTops Aunt Mary started getting a little less discrete about her flirtations with me after the episode that early morning in my guest bedroom. But she always maintained a modicum of decency. Everything was an accident, or just "natural for two people living under the same roof." When I got up later that morning, I intended to throw on a pair of shorts and go to the shower to rinse off. But when I checked my bag, and then the closet, it became apparent that I had nothing to wear. Not even the nightgown and panties that had...

Aunt Mary part 8

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The Sleeping Pills by StockingTops After my erotic experience with Aunt Mary in her kitchen (see part 7), and her telling me that I could wear or play with her panties and lingerie any time I want, I began taking advantage of her offer quite often. I was fascinated by the feeling of her silky lingerie on my body. But I was also fascinated by the thrill of exposing myself to her, and the thrill of seeing and touching her body. Aunt Mary had a doctor's appointment later that day and I stayed home alone. As soon as she...

Aunt Mary part 5

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by StockingTops I awoke the next morning to the sounds of Aunt Mary in the kitchen. As I lay in bed awake, I started thinking about how she had come in to wake me up for breakfast the day before. Thinking (hoping) she might do the same thing today, I started thinking about pretending that I was asleep when she came in. I wanted to expose myself to Aunt Mary. But I didn't want her to think it was intentional. And I wanted her to be able to look as long as she wanted, without feeling self-conscious. I left...

With Grandma’s Help

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This happened to me when I was 15. I was visiting my grandmother for a few weeks in the summer. She lives by her self in a two-bedroom house. One morning about 7:30, she comes into the room that I am sleeping in and tried to wake me up for breakfast. I had a morning erection and I really wanted to masturbate, but I never got time because she kept coming in to the room and I had to act like I was asleep. At about 8:00, tired of trying to wake me up, she grabbed the blankets and put...

Robbie – First Punishment

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Part 1 It had started out of boredom. I was a young 8 year-old and really knew better but the game of the day was to see if we could skip a rock underneath a moving car. My best friend Mark and I had been practicing on our quiet street for ages it seemed when a likely car appeared. It was up to me and I had my little stone ready to go. The plan was ridiculous of course. The rock took one bad bounce and flew up into the side of the car with a resounding 'thunk'. To Mark's...