masturbation sex stories – Page 18

Grandma’s Silk

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My balls ached... I watched as my grandmother draped her silky black nylon half slip over my throbbing erection. She then gently caressed my cock by brushing the slip up my body,my cock twitched as the nylon barely brushed across it. I arched into her rubbing,remembering how this started. I was 20 and was sent to my grandmothers to do some yardwork and spend the weekend. I had forgotten to bring any extra clothes though. I had spent the day pulling weeds and digging a flower garden.I came in filthy and dirty.Grandma was in her middle 60's,but she looked no...

Golfing With Mrs. M.

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I recently posted a story relating my masturbation experience with the gorgeous Mrs. M. As you remember, Mrs. M was the mother of a good friend of mine. She was an absolute knockout with dark, long hair, 36 DD tits, a perfect ass, and a smile that could drive you wild. My experience with Mrs. M. in the her bathtub propelled us into a frenzy of wild, sexual experiences that I still dream about today. Five days after Mrs. M. masturbated me in her bathtub, she invited me for a round of golf at an exclusive country club along Chicago's...

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Tags: big-breasts, huge-tits, masturbate, masturbation

Getting My Nephew Naked

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I’ve recently come across this CFNM fetish across the internet. I’ve seen many people, including women like me, who grew up watching their father’s or brother’s penises . I similar stories that I wish to share, I’ve never have shared this with anyone and I hope you all enjoy it. Well first things first. My name is Samantha and I am now 32 years old. I have long black hair, dark brown eyes, white skin. My breasts are 34C and have been the fantasy of many men, including my brother, he’s seen them before, specially when we were teenagers. I...

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Tags: masturbate, masturbation, medical, nurse, older-woman

Girl Time

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"I just don't know what to do with Greg. I caught him going through Alicia's panties drawer again." "Mom, he's 13 years old. You never had boys; you don't know what it's like. They're all hormones and no brains." "I was expecting the normal kid problems when I told Alice that I'd watch the kids for her while she was in Europe. Alicia's no problem. She's 16 and rather mature. In fact, she's a great help in getting me to the store. I was expecting the normal boy stuff from Greg; you know: dirt, scratches leaving his stuff all over....

Girl Time 2

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Amy opened the envelope addressed to her. "Oh mom, it's so great." "What is, Amy?" "Debbie's pool party. It's next Saturday and she invited me to the sleepover afterwards." "Aren't you forgetting something?" Amy screwed up her 11-year-old face and then it hit her. "It's Girl Time!" Girl Time started when her grandmother caught her Cousin Greg going through his sister's panties drawer. Greg was sent for the summer to live with Amy and his Aunt Kay to learn how to be a girl. When his mom got back from Europe she noticed the change...

Giving Something Back

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The sexual tension in the Simms household had been running on high for a couple of months. If you look at the situation its surprising things didn't come to a head sooner. First you've got Phyllis Simms a thirty-four year old single mother of a twelve year old son. Her husband had run off leaving them high and dry four years ago forcing Phyllis who had never had a job and very little education to provide for both her son and herself. This meant working two minimum wage jobs and having no social life at all. Sure she could probably...

Friday Night With Aunt Kay

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As a 13 yr old boy, I frequently spent days at my "aunt's" house since both my mom and dad worked full time. "Aunt Kay" was really no more than a very close family friend (someone my mom grew up with) who lived only a few miles away. She was divorced and her only son was already graduated from college, so she lived alone in a very nice home on 2 acres with a great pool in the backyard. Many afternoons Kay and I spent hanging out, swimming, sipping drinks, and listening to music. She had a basketball hoop in...

Fun with Aunt Sally

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Both of my parents traveled a lot mostly to Europe and the like. As result I grew up going from place to place, never really developing many friends. As far a my sex education was concerned my parents simply didn't have the time to explain much to me. They were well off and always had business meetings and traveling to do. So I had to learn on my on so to speak. As I matured I discovered the pleasures of masturbation and finding some of dads porno magazines helped me learn a lot about sex. In their travels to Europe...

Getting Caught

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God, I was a horny little bastard, but I was shy and still a virgin at 17. I really didn’t know how to approach girls sexually, so dating consisted of going to the movies or bowling but never going anywhere. Over the summer, I was invited to go visit my sister, who was 19 at the time, at her apartment. She was living with an 18-year-old girl friend during their sophomore year in college and thought it would be fun to have me stay with them for a week or so. Since Tammy, my sister's roommate, was cute and liked...

Getting Caught in Mom’s Panties

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I often wondered what would happen if Mom walked in on me while I was dressed in her underwear ever since the close call I had when I was 8. I was wearing her white nylon slip bra and panties. She came home while I was in her room. I closed and locked the door, changed and came out, claiming to have 'taken a nap'. I'm sure Mom saw right thru me and knew something was up. I was so tense it took me an hour to calm down from the adrenaline rush. From then on, I had a heightened...

Exposed Naked For The First Time!

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As a young person I wasn't much of a sexual being. A late bloomer, I had discovered the joys of masturbation but hadn't really put it all together yet about sex. My body was slim and I had only a small amount of pubic hair. My entire sexual experience was limited to what I saw in magazines which I eagerly and regularly pored over while stroking myself to orgasm. My life was to change the summer my parents decided to vacation in Maine. My brother and sister were older than me and both had summer jobs so when my parents...

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Tags: masturbate, masturbation

Exposed to Neighbor’s Friends

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As a 13 year old I was constantly horny, as most boys that age are. Because my parents both worked, many afternoons I would return home from school and would have 3-4 hours alone. During my "free-time" I would of course masturbate, mostly looking at my mom's clothes catalogs and the pictures of women modeling underwear. One afternoon in the middle of doing my thing, I heard the voices of girls coming up the street. I peeked out the side window of our house from behind the blinds and saw three girls who I knew just a little who lived...

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Tags: areola, masturbate, masturbation

First Time in Girly Clothes

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I had to spend two weeks with my aunt while my mom was away on business, and I flew into the airport. My aunt picked me up, but my luggage was lost. The Airline said it could be a couple days before it turns up. So I had no clothes. We got to my aunts house about 2pm, my aunt had to be at work at three, and would not be home till 11. She told me that her ex boyfriend and his teen daughter lived with her a year ago, and the daughters clothes were upstairs in the spare...

Enjoying Her Panties

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My first year out of college found me working for a large well known personal loan company. At the end of each month I had to go out and knock on doors of customers who were behind on their payments and ignored all of our phone calls for payments on their delinquent loans. I had a couple of interesting things happen to me while I was in some customer's homes, so I have to share the best one of all. Every month I would have to go to this same house where the customer's wife was always home with the...

Examining Billy

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Part I It was a warm summer afternoon. Courtney Benson had her nearly 14 year old son Billy laid over her lap for a well-deserved bare bottom spanking. Since the boy had just come back from swimming at a friend's house, Courtney made her son remove his still wet swim trunks and t-shirt in the washroom adjacent to the kitchen and then escorted the naked naughty boy to the master bedroom for his spanking, smacking his buttocks with her hand until they reached the bedroom. Then of course, she grabbed the dreaded hairbrush from the vanity and made Billy lie...

Dear Diary

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May 17th Today, Mom walked in on me while I was masturbating. That's the word she used. The guys at school call it whacking your wiener, but Mom says that's crude. Now that I'm eleven, Mom says I'm old enough to stay by myself after school. I usually get home about 3:30, and Mom's usually home from work by 4:00, so it's not that big of a deal, but today, school got out early, so I was home at 2:00. I didn't know she was getting off work early. When I know I'm going to have some privacy, I like...

Don’s Panties

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*** Chapter 1 *** Don was quite small the first time he put on his older sister's pink silk panties but he liked it. He was quite upset the first time his sister and her girlfriend caught him wearing these panties. "What on earth are you wearing," Jane said as she and Judy walked into the room. They stood staring at Don wearing nothing but pink panties. "You're not supposed to be here yet," was all the young Don could say but he knew he had been caught. "Wait till I tell Mom," Jane laughed. "No, please you can't...

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Tags: humiliation, masturbate, masturbation, older-woman

Dream Ticket

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The experience I am about to relate could only have happened in Britain in the romantic days of rail travel, when there were still real trains hauled by steam locomotives. Those were the days when tights were worn only by principal boys in pantomime. Women wore fully fashioned nylons with sexy heels and seams and held them up with suspenders. The day it all happened, I was just turned 18 years of age. Forty plus years on the erotic images in my mind of what happened on that day are as vivid as ever. I have to confess though that...

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Tags: anal, anus, doctor, masturbation, medical, nurse, nylon, rectal, rectum

Dressing Memory

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In the 1950,'s when I was 12 years old, I grew up in a family of all women, so it wasn't unusual to wander by an open bedroom door and catch one of them dressing up for a date. I always admired the clothes that girls and women got to wear. Such a variety of pretty things, from delicate undergarments to soft, sensuous outerwear. For a guy it was pull on a pair of Jockey shorts and a pair of pants or jeans, top it off with a white shirt and bowtie and you were dressed. A young girl dressing...

Ed

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The school bell rang, sounding the end of the school year and the start of summer vacation. No one could be happier than Ed. The thirteen-year-old boy walked home from school with his two best buddies, Chuck and John. They planned all of the things they were going to do this summer, fishing, swimming, and long bike rides. Ed lived in Miami Fla., with his mom Jen. He was an only child and his dad left them when Ed was only four. Jen worked in a market and supported Ed all by herself. After supper that night,...