older woman boy sex stories – Page 2

Spending the Night at Grandma’s House

★ ★ ★ ★ ★

0 average (0 rating(s))

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

★ ★ ★ ★ ★

0 average (0 rating(s))

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

★ ★ ★ ★ ★

0 average (0 rating(s))

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...

READ MORE

Tags: medical, nurse, older-woman-boy

Mrs. Peters

★ ★ ★ ★ ★

0 average (0 rating(s))

"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...

READ MORE

Tags: big-boobs, mommy, older-woman, older-woman-boy, pregnant

Billy and Aunt Karen (part 1)

★ ★ ★ ★ ★

0 average (0 rating(s))

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...

READ MORE

Tags: nephew, nylon, older-woman-boy, stockings

Billy and Aunt Karen (part 2)

★ ★ ★ ★ ★

0 average (0 rating(s))

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...

READ MORE

Tags: medical, nephew, nylon, older-woman, older-woman-boy, stockings

Billy and Aunt Karen (part 6)

★ ★ ★ ★ ★

0 average (0 rating(s))

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

★ ★ ★ ★ ★

5 average (1 rating(s))

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 been...

READ MORE

Tags: nephew, nightgown, older-woman-boy

Aunt Mary part 8

★ ★ ★ ★ ★

5 average (1 rating(s))

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 left...

Aunt Mary part 5

★ ★ ★ ★ ★

5 average (1 rating(s))

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 the...

READ MORE

Tags: nephew, nightgown, nylon, older-woman-boy, satin

Auntie’s Panties

★ ★ ★ ★ ★

0 average (0 rating(s))

I've had a panty fetish since age 11. My aunt came to live with us after my father died. Always after my aunt came home from work, she would undress and wander about the house in a white nylon full slip or a bra and half slip. She would wear a white or pink full-brief panty brief that I could see thru her slip. Usually, I was the only one home and I always felt a little strange looking at her (like I was doing something wrong) and she knew it. She was always pulling me close to her,...

A Few Days with Aunt Jen

★ ★ ★ ★ ★

0 average (0 rating(s))

I was staying with Aunt Jen for three days while my parents went to Scotland for the funeral of Uncle Jack. “Aunt Jen,” as I had always known her, was not actually my aunt but Mum’s friend Jennifer, but she had always been known as Aunt Jen for as long as I could remember. Aunt Jen was in her mid-forties and worked as a nurse, quite ordinary but nice. Although I think she had struggled financially since her husband died, she was always very smartly dressed and always seemed to be wearing stockings, I remember. She and her husband had...

With Grandma’s Help

★ ★ ★ ★ ★

0 average (0 rating(s))

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...

Tommy Gets Taught

★ ★ ★ ★ ★

5 average (1 rating(s))

Little Tommy Turnell wasn't so little anymore. At least that's what his Aunt Susie said every time she saw him at Christmas. Except now that he had recently turned fourteen, there had been some definite changes. The sandy brown-haired youth was filling out in some areas. Muscles, teeth, hair. All are getting stronger and more mature. But it was those other areas he didn't need to worry about before that were really giving him worries. Tommy was concerned when he found weird hairs growing out of his armpits, and even worse, around his private parts! And that private part was...

Step-Aunt and Painkillers

★ ★ ★ ★ ★

0 average (0 rating(s))

I was about 14yrs. old. I had to always go to my grandma's house after school so she could watch me cause my mom had to work. One day my uncle who was a truck driver had to move in with my grandma and his new wife too, my step aunt. My grandma had gone thru cancer and stuff so she was on pain killers. Well my aunt started to steal them, all the time. She was fucked up a lot. Any way she and my uncle lived down in the basement. My uncle was always on the road. My...

Robbie – First Punishment

★ ★ ★ ★ ★

0 average (0 rating(s))

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...

Nurse’s Van Raalte Sheerios Brief Story

★ ★ ★ ★ ★

0 average (0 rating(s))

My real weakness is seeing and touching a woman wearing full cut, white nylon panties. It goes back to when I was just a kid, when I was in the hospital for a short stay with the flu. Late one evening when I had been asleep for hours, a very pretty young nurse came into my room to check on me and my roommate. She didn't realize that I woke up because I kept my eyes closed most of the way, and got to see her slip out of her dress and give herself a quick sponge bath. She was...

Oliver’s Aunt

★ ★ ★ ★ ★

0 average (0 rating(s))

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...

My Start with Auntie’s Things

★ ★ ★ ★ ★

0 average (0 rating(s))

My auntie kept her underwear in a drawer in her bedroom. I used to sneak in and pull it open, and run my hands over the neat piles of white slips, bras and panties. The sight of them aroused me greatly. My heart would pound as I imagined myself slipping into them. One day when we were alone in the house she caught me with the drawer open, running my hands over her undies. I was about sixteen at the time. She asked me sharply what I was doing. I mumbled shamefaced that I wanted to dress in her clothes....

My Grandmother Masturbates Me

★ ★ ★ ★ ★

0 average (0 rating(s))

It started with her just washing me... I was raised by a single mom. When I was younger I would have to spend two days every week at my grandma's while my mother worked. My grandmother also lived alone. Every night when I was there, grandma would give me a bath. She would take out a special sponge and wash every part of me. When I was older, I began to think it was odd--her bathing me, since my mom didn't even do this. But I really liked it, so I never said anything. By the time I was a...