older woman sex stories – Page 6

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 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...

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

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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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4 average (1 rating(s))

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 on the...

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...

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

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 I...

Stepmother’s Lingerie

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I got started in my fetish in my teens. I love the feeling of silky nylon rubbing me especially long slips and nightgowns. Here's a story of my experiences. Well I was about 16 years old, and my dad had been married twice,to my mom then my stepmom and now he's divorced. Well even after his break-up with my stepmom my family still kept up a relationship with her. During the summer I would get to travel and stay the entire summer with her. She was about in her mid forties but a great looking older woman,with a thick build,pleasingly...

Stolen Clothes (part 1)

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4 average (1 rating(s))

When I was almost 15, I used to go skinny-dipping in a lake about 3/4 of a mile from where I lived. This lake was in a wooded area that bordered along my subdivision. I felt quite comfortable swimming there as I never saw anyone around. One day after my swim, I got out of the lake and to my horror my clothes were gone! I never heard anyone and couldn't understand what had happened. At first I thought maybe I was just mistaken about where I laid them down. After a search failed to locate them, I started to...

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...

Skirt Day

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Chapter one: how it began Lisa wondered why it was that despite her successful career in middle management and a plethora of dating options consequent to her tall, blond good looks, she still felt empty and unhappy. In fact she didn't much like dating - all too often she would find the guy's shallow attempts to impress, to make her laugh, and to get into her jeans to be frustratingly unsatisfying. She usually delivered a forceful rejection to each guy, and even went on to instruct him on how to improve his life. Her career was taking off - she...

Sexy Godmother

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My father left when I was 12 years old and shortly after that my Godmother Betty began to take a special interest in me. She stopped at our house often, brought meals and took me out to plays and concerts. Betty was about 40 at the time, a large woman with huge voluptuous breasts. She was five years older than my mother and treated her like a little sister. My general impression was that Betty was a lesbian, since she lived with a woman and my mother always avoided questions about her, including why she never got married. By the...

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

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...