older woman boy sex stories – Page 2

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...

Nurse’s Van Raalte Sheerios Brief Story

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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

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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

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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

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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...

Mom (stepmom)

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Tags: incest, mom-son, older-woman-boy

Milli’s First Lesson

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Janice pulled the Lexus into the driveway, and noticed her bedroom light on. She was positive she turned it off before she left this morning. If her wayward Nephew was nosing around in her room there would be hell to pay. She was already extremely ticked off at having to attend a meeting with his Principal this morning. A meeting which ran on too long, causing her to miss her flight to Chicago. Thank goodness she was able to assure the Principal that Bill would be on his best behavior for the next few days, until graduation. Janice closed the...

Forced to Serve at my Aunt’s Tea Party

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When I was 12 years old, my parents went on a two week vacation and sent me to my Aunt's house to stay with her while they were gone. My Aunt Shirley was my mother's older sister. She was about 50 years old at the time. And she was a very imposing woman. She had large breasts, large hips and thighs, and a small waist that was often wrapped with a belt. She was a very strict woman and she informed me upon my arrival that if she was to be responsible for me, then I would not be allowed...

Doctor Laura’s Procedure

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Laura slipped on her white doctor's lab coat and she stood and looked at herself in the office mirror. She was just barely five foot tall more like four foot eleven. She had short professionally cut blonde hair and bright blue eyes. She wore a nice color of red lipstick that didn't scream tramp but did make a man take notice of how full they were. She looked down at the rest of her ensemble, she wore a skirt that came about two inches above her knee with nice black high-heel shoes, and a light pink top with a neckline...

Billy and Aunt Karen (part 3)

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Fashion Conscious Karen It was obvious that Aunt Karen loved fine lingerie, she obviously adored the way that it felt against her body, and he wondered if if she knew how much it could turn on men as well. Karen was an extrovert and she occasionally forgot her natural modesty to discretely, if unintentionally, reveal some of her lingerie finery in the company of others. Being a willing voyeur of Karen was one of Billy's favorite extra-curricular activities at family gatherings. Often she wore a skimpy lingerie-style lace bra under a sheer blouse. The sheerness of the blouse was...

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Tags: aunt, aunt-nephew, hosiery, incest, nephew, older-woman-boy

Billy and Aunt Karen (part 4)

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Karen on the Recliner As they walked back out of the store, they passed through the furniture department. An enterprising salesman offered, "Try our recliner, ma'am. The most comfortable thing around...and they are on sale this week. Karen paused, and the smiled and started to walk on. "Oh, go on, Aunt Karen. Try one out...just for fun." Deciding to humor her nephew, she smiled and nodded her head 'okay'. He quickly re-inventoried what Karen wore -- a nice navy blue suit, three plus inch high-heeled pumps, and sheer light brown hose. He was new at voyeurism, but he quickly...

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Tags: aunt, aunt-nephew, incest, nephew, nylon, older-woman-boy

Billy and Aunt Karen (part 5)

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At the Dentist Karen had promised his mother that she would see to Billy's dentist appointment in her absence. Since Mary also was due for a check-up, she made both of them an appointment for the same day. Mary could then provide any support he needed. Karen dropped him off at the dentist's office and then when off to attend to the matters of the day. Billy was sure he didn't need any support, but a chance to be with his attractive nineteen year old cousin was worth the trouble. Well, she was due at any minute. Billy was...

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Tags: aunt, aunt-nephew, incest, nephew, nylon, older-woman-boy, punishment

Aunt Karen

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Chapter 1 A Bird in the Hand I was always fond of my Aunt Karen; she was a grown-up for sure, but really not that much older than my sister and I. She occasionally baby sat us and we always had a fun time with her. As I got older and started to have "manly urges," I also noticed that she was a very attractive woman. I thought the world of her. That is, until that summer she spent at my house when she brought that world crashing down around me. I was twelve, and my sister, Carol, was eight...

Aunt Karen part 1

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When I was 14, my parents went away for a 2 week vacation and made arrangements for me to stay with the next-door neighbors while they were gone. The neighbor had a son close to my age, that I was good friends with, so it wasn't bad for me. My friend's name was Dave, and he lived with his single mother who I called Aunt-Karen. She wasn't my aunt, but that was how I had been brought up to refer to her. Aunt-Karen was attractive, although certainly not beautiful, and was probably in her mid to late thirties. She was...

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Tags: aunt, aunt-nephew, incest, nephew, nightgown, nylon, older-woman-boy

Aunt Karen Part 2

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My next erotic experience with Aunt-Karen happened later that day. She was taking a shower in the master bathroom while her son (my friend) Dave was showering in the hall bathroom. I was watching TV when I heard her calling from her bathroom to me. "Will you bring me a towel?" she called. "I'm soaking wet, and there aren't any clean ones in here." I grabbed a clean towel from the hall closet and brought it into her room. "Will you bring it in to me?" she asked from the bathroom. The door to the bathroom was opened, and I...

Aunt Karen Part 3

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One day, while I was staying at my friend Dave's house with him and his mother (who I call Aunt Karen), he was at one of his music lessons, and Aunt Karen was going out to do some shopping. "Would you do me a favor while I'm gone?" she asked me. "Of course," I replied, "anything!" "There's a basket of laundry in my walk-in closet," she said. "Will you fold it and hang it while I'm gone?" "Sure!" I said. She gave me one of her big warm hugs and said, "Thank you. You're such a sweetheart!" Then gave me...

Aunt Karen Part 4

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(Changing the Lightbulb) If you've been following my adventures with Aunt Karen, then I won't need to introduce the story or situation to you again. If you haven't been following, then you might want to go back and start from my first installment and work your way up to this one. My last experience with Aunt Karen had been both my most embarrassing and most erotic experience so far. She was kind enough not to mention it again. In fact, she acted as if it had never happened. I think the situation, the tension, between us worked better for both...

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Tags: areola, aunt, aunt-nephew, incest, nephew, older-woman-boy

Aunt Karen Part 5

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(Picking out a Dress) My second week with Aunt Karen was even better than the first! I had forgotten that David (my friend and Aunt Karen's son) was going away on an orchestra tour for a week. I was going to be all alone in the house with Aunt Karen for a whole week! I tried not to sound happy when David reminded me he was going to be leaving. I assured him that I'd be okay. I told him his mom was cool and that I'd be okay staying with her for the week. But secretly, I could hardly...

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Tags: aunt, aunt-nephew, incest, medical, nephew, nurse, nylon, older-woman-boy

Aunt Karen part 6

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We were on our way to the mall when Aunt Karen started talking to me about the “rules.” I don’t remember exactly how she put it, but she talked about how she knew we had both been having fun for the last few days and that she wanted us both to feel comfortable and continue having fun. But she was concerned about my being only 14 years old and that certain things were illegal for her to do with someone my age. She said she would feel more comfortable if we set out some rules that would protect us both....

Aunt Karen part 7

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(Taking a Nap) In the afternoon, Aunt Karen told me that she was tired and that she was going to take a nap. She asked me if I'd like to lay down with her and take a nap too. Of course I said yes. It was a warm afternoon, but not hot. I walked into her bedroom with her and she went to the window to open it and let some air into the stuffy room. I remember I just stood there at the end of the bed, feeling a bit awkward. She sat on the queensize bed and patted...