masturbating sex stories – Page 5

Sleeping Step-sister

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Kelly was 14 when it all started, and while she wasn't supermodel material she was certainly pretty, fairly well-developed and quite popular with the boys at our school. We had been pretty close during our pre-teen years, and were often left alone, so were very used to each other's company. There had been a few experimental games of 'doctor and nurse' in previous years, but they weren't entirely sexual, more out of curiosity and boredom. However when I hit the hormone years I started to get very, very curious about girls. Naturally my step-sister, being the most attractive female in...

Showering with Mom

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When I was a child, I had this problem: Every morning, I would argue with my mom over who would use the bathroom first. We were always in a hurry. I had to go to school; she had to go to work. When I was going first, she was always complaining that I was hogging it, and vice versa. So one day, we got in the shower together. OK, actually she got there first and I kind of crashed. Stubborn as a mule I refused to leave, so we ended up sharing it. But what started as a joke, turned...

Showing Sister

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I discovered masturbation as a child perhaps even before kindergarten. I knew it felt good touching my penis and discovered how to rub it against the mattress to make it feel good. I even started having sexual fantasies to go along with my masturbation sessions. Mostly these involved girls in my class. They would capture me, tie me up take off my clothes (somehow they managed to get me completely naked in spite of my being tied up) and play with my penis. I really didn't know why they would want to do it, and how they would know how...

Sir Sammy and the Red Fox

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by Reed Monday It was another Monday, Sammy rolled over and reached for the snooze button on the alarm. God he had grown to hate that awful buzzing that awakened him every day for the past 25 years. He arose and immediately turned the hot water on in the shower. He stepped in and slowly gained consciousness as the steaming water beat down on his body. Though he didn't want to, he shut off the water after 10 wonderful minutes. He dried, combed his hair, shaved, brushed his teeth, rolled on some deodorant, and splashed on some cologne. Quickly he...

Sister’s Panties

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Every since I began masturbating, I've always had a panty fetish. I don't remember where this particular fetish originated from, but it just came to me. I loved the feeling of the satin or silk panties wrapped around my stiff cock and swollen nuts. It felt like heaven sliding up and down my shaft, bringing me to orgasm. I used to leave huge loads of cum in the panties of my mother and sister. While I masturbated I usually took a few minutes to sniff and lick the panties before I blew a load into them. Since they were from...

Rick and Caroline part 7

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Caroline had been very upset the last few days she hadn't confided in me as to what was happening but I was about to find out. Rick and his boss one of the executives under Mister Pearce were being sent to Japan on an impromptu business trip. There were a few matters that needed clearing up. Mister Pearce knowing Caroline's fear of having to move there hinted that Rick and the other executive were going first hand to arrange living accommodations for a few select employees and their families that were being transferred there. He personally hinted to Rick that...

Rick and Caroline part 8

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I was alone in the young couple's home, Rick was away in Chicago, and Caroline had gone shopping. I had only been over to the house once since the pool party. So to get caught up on what was happening if anything I unlocked the desk drawer and took out Caroline's diary. There were a few entries expressing her concerns about several of the male executives phoning her and graphically describing her vagina and naked body. They thanked her for allowing them to see all of her hidden charms and assured her that the next time they met they would...

Sammy’s Hot Summer Ch. 1: The New Neighbor

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When I first saw that big yellow moving van backing into the driveway, I was angry, I'll admit it. Up till three months before, and from the day I was born, my best friend Kevin had lived next door to us. Then his father got some great new promotion at work. Next thing I knew they were moving to Florida, right in the middle of the school year. When you're 13, and you lose your best friend, it's kind of like losing an arm or a leg. Especially when summer vacation rolls around, and your best friend was the...

Sammy’s Hot Summer Ch. 2: A Helping Hand

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I couldn't believe it. One minute I was laying there in bed, jerking off, and before I knew it, the room brightened, as somebody turned the lamp on. I hadn't even heard the door open. I turned, and there she was, my neighbor Bethany, dressed only in a pair of heels, her red hair cascading down her back, her huge tits ... well, just huge. Before I even knew what was happening, she had crawled on top of me, pushed my sheets aside, and was riding my cock, her nails digging into my chest, her breasts bouncing, moaning louder...

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Tags: anal, anus, big-breasts, huge-tits, masturbating, mom, mommy, mother, mother-son, rectal, rectum

Seen by my Neighbor

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When I was late 18 I began doing odd jobs for our neighbor Miss Grace, who was then about 50-ish and had been widowed. These jobs included a bit of gardening, cleaning the gutters, washing her car, etc. Mom didn't mind my going over there and the pocket money was good. Several months later, one summer day I was standing cleaning some leaves out of the gutter when I found I could look into her bathroom and there she was stepping into a shower. I only saw her bum but it was enough to make me stiff and I had...

Sharing Masturbation With Mother-in-Law

4/5 - (1 vote)

I am 28 years old and been married for a number of years but still enjoy masturbating almost daily. Occasionally, my wife wants me to stroke it for her during foreplay. This really turns her on. So, anyway, about a month ago, we are visiting my mother-in-law, who lives out of town. The first night there, I am taking a bath, and decide to jack-off while in the tub. This was not an extra special session, just lathered it up, stroked it for a few minutes, and shot my load. I get out of the tub, and the rest of...

Shopper and the Stock Boy

4/5 - (1 vote)

Chapter One - Dressing by the rules Jennifer Hart walked determinedly into the exclusive ladies clothing shop. It was late in the day and nearly closing time. She needed a new outfit and she did not want to miss the end-of-season sale. Surely the store could stay open a few minutes longer if necessary. Her high heels which had clicked noisily on the side walk were quiet on the tasteful carpeting. Greeted by a sales clerk who glanced tellingly at her watch, Jennifer looked quickly through the racks of sale clothing. A chic beige colored dress caught her eye. She...

Shower Check by Mom

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This happened when I was much younger, and I have masturbated to this experience many, many times. I grew up in a normal, loving, everyday family with two siblings, older brother and sister. Both my older brother and I have foreskin, which is not that common in the USA where we live. Growing up, mom always told us to pay special attention to keeping our privates clean during baths as she bathed us, inspecting the cleaning job herself. As we got older and took baths ourselves, she did not do inspections that often, but would just ask us if we...

Playing Jacks

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When I was 14 we went to my aunts house for a vacation. My cousins (a boy who was 9 and a girl who was my age) decided to go swimming in lake Huron. I didn't have my bathing suit with me so my aunt lent me a pair of the 9 year olds stretch pants. After coming home from swimming. My aunt told me to take off the stretch pants because if I wore them too long they would no longer stretch back small. I rapped a towel around me and took them off with the female cousin watching...

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Tags: masturbating, masturbation

Playing with Mummy

4/5 - (2 votes)

"Ready for a bath honey?" Anne asked her son as she stood in the living room doorway, already in her flowing white dressing gown. "Almost mummy," Sammy replied. The dark-haired child was kneeling on the floor, wearing just his Spiderman pyjamas as he scribbled in a colouring-book with wax crayons. "It's getting late," Anne replied, "It'll be bedtime soon. C'mon honey, it's a school night. You can't stay up forever." "Okay mum," Sammy said. He sighed and put the book and crayons on the coffee table. Like any eight-year-old boy, he didn't really like the idea of having to go...

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Tags: anal, anus, enema, masturbating, masturbation, rectal, rectum

Posh Mum

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I had never really thought of my friend Pat as 'posh', but his mother certainly was. Her voice had the beautiful lilt of the refined southern Irish. Her manners were impeccable. She looked the part too with short, very dark, well cut hair, a slim but shapely figure, elegant clothes and a regal bearing. You felt you had to be on your best behavior in her presence. At fifteen I fancied her desperately despite her being an 'older woman' of around forty. When she opened the door to me that morning however, she looked just a little flustered. "Hello," she...

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Tags: masturbating, masturbation, nightgown, older-woman

Rick and Caroline part 3

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The next morning Caroline greeted me at the door wearing the shirt to Rick's pajamas. She had on a pair of feather trimmed high heel slippers. As she walked up the few steps into the kitchen I saw the bare cheeks of her ass. "Coffees ready!" She said, placing a cup on the end of the table where I usually sat. I could smell the bacon cooking in the frying pan. "RICK! Rick your breakfast is ready!" She called out lovingly to her husband. "I'm so hungry I could eat a horse!" Rick said coming into the kitchen. He was...

Peter File #09

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==================================== In which Peter gives a generously-bosomed friend a hand with the milking, and the favor is returned. Editor's Note: Partialism, the fixation of sexual attraction on secondary sexual characteristics, is commonly associated with masturbatory addiction. The habitual masturbator, accustomed by long practice to manual gratification, loses his capacity to perform normal coitus and may find the primary female genitalia intimidating (see Peter File #05). He transfers his sexual attention to other parts of the female body, most often the bosoms, usually responding strongly to women with generous endowments. The logic of this choice is clear: After her vulva, the...

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Tags: big-breasts, huge-tits, masturbating, teats

Peter File #10

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- In which Peter explores the connections between masturbation and spanking. (Editor's Note: The explicit sense of shame that afflicts most habitual masturbators causes them to seek out (sometimes unconsciously) opportunities for punishment and correction. Often this results in a poorly inarticulated desire to be spanked, especially by a sexually attractive woman to emphasize the humiliation of the experience. The recent growth of commercial "spanking salons", which provide the masturbator with convenient and affordable adult spanking services, may be largely driven by this phenomenon.) When Peter first saw the ad, a small display in the back pages of...

Peter File #12

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====================================== (Editor's Note: Secondary sexual dysfunction is a frequent consequence of excessive masturbation, and premature ejaculation is one of the most common clinical manifestations. Two complimentary processes are at work: frequent masturbation lowers the ejaculatory threshold and accustoms the sexual organs to non-coital emissions, thereby setting the stage for praecox ejaculation; and the moral degradation of masturbation leads to lowered self esteem and increased anxiety with women, resulting in almost unbearable tension when presented with coital opportunity. The result is a loss of normal ejaculatory control, and a habitual masturbator is often unable to accomplish sexual intercourse even with a...