older woman sex stories – Page 5

The Exploits of a Perverted Young Boy

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My Introduction Into The World of SEX I first started to get erections when I was 10 and I had heard about masturbation but I didn’t really know what it was about. I had overheard some boys in school talking about it one day but thought it was gross. I lived with my mom who was 33 and my big sister who was 12 so I couldn’t really talk to anyone about how to relieve the tension. One day after school I was sat my friends house and he told me he had found a sex movie in his parents...

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Tags: masturbation, older-woman, stockings

The Farm

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Chapter 1 It was one of those long weekends and Mom and Dad decided that they needed to be alone. So, all of a sudden I found myself packed up and leaving to stay over at my Aunt's house. Not to say that I don't like my Aunt Julie, but I had plans. My friends and I were going to go down to the lake and pick up some girls. For, a 17 year old guy it was hard enough just trying to fit in, but being sent off to your aunt's to be babysat was definitely a shot to...

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Tags: anal, anus, aunt-nephew, humiliation, older-woman, rectal, rectum

The Funeral (part 1)

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By Bob Gladys's new 1970 car was parked under the shade of a big old pine tree. The hood was up letting the over-heated engine cool down. We were sitting on a picnic table nearby eating the lunch that my mother-in-law had packed for us. Although the cooler of beer wasn't as full as when we started Gladys had been sampling on the long journey. I opened two more beers for us and took another sandwich from the container. One of Gladys's oldest and dearest friends had suddenly passed away; we were on our way to Sudbury to attend the...

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Tags: anal, anus, masturbation, nylon, older-woman, rectal, rectum, satin, stockings

The Funeral (part 2)

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By Bob Once on the highway I set the cruise control to just under the speed limit. I had to keep my wits about me as I was driving drunk. As I drove along into the bright afternoon listening to the radio and feeling the warm breeze on my face from the open window I glanced over at my passed out mother-in-law. She was slumped back against the seat with her mini skirt still hiked up around her waist. Her sheer black silk blouse hung open her breasts jiggled with each bump along the highway, her nipples semi-erect. We were...

The Church Lady 4

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by Stockingtops I went to the kitchen to join Miss Betty for breakfast. I had found another nightgown to wear, as she had instructed. It was a long pink nightgown, made of sheer nylon material. My nude body was somewhat visible beneath the material. As I thought of appearing before her dressed this way, my youthful erection returned, tenting out the material in front of me. As I walked into the kitchen with my erection bobbing around, I watched Miss Betty's eyes focus on my erection, which she could plainly see beneath the see-through nightgown. "That's a very nice choice,...

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Tags: areola, nightgown, nylon, older-woman, punishment

The Bridge Club

1/5 - (1 vote)

Ann Williams was getting annoyed with her son, Robby, for staring at her friend Lena's tits. Ann knew Lena was a whore who loved to show off her big, if saggy, breasts; but she thought her son was staring more than he should. She didn't blame her son for looking at the long cleavage line in the middle of Lena's low-cut blouse, but there are limits! To make it worse, Ann could clearly see her son's cock sticking up and to the left in his pants, clear up to his belt. "Excuse me for a moment," said Ann to her...

The Camping Trip

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I was a typical 15 year-old boy with raging 15 year-old hormones. It was summer in upstate New York and my best friend Rob and his family had invited me on a camping trip to Wellesly Island on the St. Lawrence River. Since my family never went on vacations, I literally jumped at the chance. It was about a three hour drive up to the river and onto the island, and toting along the huge trailer wasn't speeding us up any. The camping contingent consisted of Rob's father, mother, and two older sisters. Kathy was eighteen, flat-chested but with an...

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Tags: older-woman

The Cavern

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After the initial shock of my divorce, I decided to hell with it, and concentrated my mind on my job. Putting in way too much overtime, taking on extra work loads from everyone. I buried myself in it, forgetting about the one thing we all need. Because of this, I was quickly promoted and went up a floor in the organization that I work for. Rather than having a little opened area that I called an office, I was given a rather large office, nice furnishings, and a secretary. Knowing business like I do, I know that it's ok to...

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Tags: older-woman

Teasing Wife

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Dear Sonia, My wife and I have been enjoying adding some exhibitionism into our love life with rather pleasing results ;-), in part thanks to you ! Here is a true story. Enjoy. One evening on my way home from work my wife called to say that we should go out to dinner at a cafe, and maybe catch a movie as she was not in the mood for cooking, or being at home. She suggested I detour, and meet her in the city at trendy cafe we knew. She would take her car and meet me in about half...

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Tags: older-woman, seamed-stockings, stockings

Thanksgiving

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* Danny "Danny, are you sure you have all the emergency numbers?" my mom asked as she ushered my two kid sisters into the car. "Don't worry, mom, I'll be OK," I said waving back to her as she got in herself. "It will only be a couple of hours until dad gets home anyway." That was the plan. Mom's part of the plan was taking Pam and Amy to my aunt's house for the Thanksgiving weekend early, and I would wait at home for dad to get home from work and ride up with him. I was happy to...

Thanks, Mom

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I first remember wearing my sister's panties when I was younger. I remember walking through the kitchen, while my aunt and mother were looking at the latest catalog. They were laughing, so I ask them why. I thought my mother may have told her how I liked the panty and bra area of it, but they just said they thought it was funny that they were selling unisex panties. I just smiled and kept doing my boy things. The next morning my Mom ask my Dad if I could stay home and help her rather then helping him. I wondered...

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Tags: nylon, older-woman, panties, panty-fetish

Thanks to My Hot Sexy Aunt

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I was 18 years old and had just graduated from high school. I had no idea what I wanted to do with the rest of my life. My mom wanted me to go to college but I wanted to find a job and buy me a new car. The week after graduation my mom suggested that I catch a bus and go visit her younger sister. She called it a vacation or get-away. I knew what my mom was thinking. She had probably called her sister and asked about me spending some time with her in hopes that her sister...

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Tags: big-breasts, huge-tits, masturbation, older-woman

Thawing the In-Law

5/5 - (1 vote)

I was lucky I got a job, but it was in the city, 400 mile from the little bush town where we lived. Still, it would be a welcome break. We, I mean my wife and I lived with her Mother since we were married. This wasn't a bad thing, except for one aspect, her Mother was not accepting of her daughter's wanton abandon the bedroom. When we were first married, she walked in on us several times while we were having sex. I didn't mind, in fact it was a bit of a turn on for me; having my...

The Aunt and the Nephew (part 2)

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a Second Imagining or Much Ado About Nothing The nephew is a robust fellow and as such has normal urges and desires that are not relieved in the manner which Nature intends. Such a build-up of longings and needs must find an outlet and the nephew follows in the time-honored footsteps of countless adolescents by fiddling around and frigging himself. At first this happens in what he thinks to be private moments and in secluded surroundings. After bed- time at night he rubs and tugs with abandon under the covers and at times he is just as unconcernedly active...

The Barter System

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Doreen May and her nephew Tyler watched the woman behind the desk carefully. It was Friday afternoon and they were in the office of the Loan Officer at the First National Bank. Doreen had applied for a car loan and now waited to find out if it was approved. The loan officer was an attractive woman in her forties. She had dark hair and deep brown eyes. Tyler also noticed her long red fingernails. She tapped them on her desk while she was on the phone. The 13 year old boy looked away quickly whenever she smiled at him. The...

The Beginning Of My Panty Fetish

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How and why I love panties To begin with, growing up I was that short, skinny, scrawny kid that everybody picked on. Even in my late teen years I was only five feet tall and weighed approximately a hundred pound and even that was on a good day. So needless to say, I didn’t have a lot of dates, and sex was only something I read about in books, or if I was lucky enough to ‘find’ one…an adult magazine. Usually I bought those cheesy magazines like True Detective or something similar. You know the type, the ones with the...

The Best Experiences of My Life

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I started wearing girl's panties when I was very young. I started by wearing girls shorts I would find in the class room. The first pair of panties I wore were my sister's. I was curious and got very aroused by wearing girl's underwear. Soon after, I started masturbating in them. I must state here that I have never masturbated with my hand. I would masturbate by laying face down on the floor and put something soft, like a pillow or towel under my penis, and then start to rub back and forth while wearing girls panties. When I was...

SUMMER VACATION AT AUNT KAREN’S

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The summer I turned 17 was a very special one that I will never forget. It was spent at the summerhouse of my Aunt Karen, and it helped me discover the full extent of my long time attraction to maternal discipline. Aunt Karen was married to my mother's younger brother, and was hardly 40. She was a very attractive woman, and although young and inexperienced I instinctively sensed that she was much more erotically oriented than most of the women in my family. She always wore make-up, and she dressed in a sensual and even sexy way. And I was...

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Tags: masturbation, older-woman, punishment, spank, spanking

Tammy’s Panties

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I developed my panty fetish early in life when I discovered my sister's lingerie drawer. Like most young males, I began to discover masturbation around puberty. Discovering my sister's panty drawer added a whole new dimension to my methods of masturbation. The feel of satin drove my dick wild. I would either wrap her panties around my dick or jack off, or I would put the panties on a pillow and fuck them until I came. I visualized girls in my class or women I saw during the day while jacking off with my sister's panties. As I got older...

Taught a Lesson by Mrs. Haverford, RN

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My heart leaped to my throat as I heard the garage door opening. Because I was sneaking around in the first floor master bedroom completely naked, fear of discovery made my heart pound and my hair stand on end. All I had time to do was hide under the vanity table and hope the coast would soon clear. My silly little masturbation games were finally going to get me in terrible trouble. To my horror, I immediately heard multiple female voices and laughing as people came in through the garage door, just around the corner from the bedroom where...