older woman sex stories – Page 15

George part 2

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By BOB The noise and smoke inside the bar was a shock to our senses as we came staggering in, by the time we made our way to the bar through the jammed room the effect of the air conditioning was lost. The place was full mostly men that had stopped in on their way home from work. Luckily we found three stools together at the bar and ordered a round of drinks. There was an uproar as the guys saw Gladys' outfit, whistles and lewd comments from deep in the room. All the attention seemed to inspire her to...

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Tags: anal, anus, older-woman, rectal, rectum

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...

Finish What You Started

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"Son, always Finish What You Started," my father once taught me. "It may seem awkward at first, maybe even boring and you may not see where it's leading. But with some stick-to-it've-ness, you'll get your prize at the end with a big payoff." *** When did I realize that I was in love with the most beautiful woman I've ever seen? I've always 'loved' my mother, yet I don't remember when I fell in love with my mom. I do remember that the first time I came from masturbating happened while I was fantasizing about her. That may be when...

First Panty Spanking

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I was at my friend Linda's house. Linda was a year older than me but we were very good friends for many years. Linda and I were going to go swimming that evening, but first she had to baby-sit a couple of neighborhood kids for a couple of hours. Instead of going home, we decided I should just wait at Linda's house. Her Mom was at work and I could watch TV for a while. When Linda left I waited for 15 minutes to make sure the coast was clear. Deciding it was safe; I headed to her bedroom and...

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Tags: nylon, older-woman, spank, spanking

Evan’s Aunt

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Evan had not lived in his aunt's house for nearly four years. After the death of his mother and father at the age of six and a half he had been placed with his Aunt Phoebe and spent the next three years there. Phoebe was not actually his aunt; she was officially his third cousin but, because of the disparity in their years, he had always been expected to refer to her as 'Aunt Phoebe'. When, at the age of 39, Phoebe decided to take a leave of absence from her position as a rural visiting nurse to pursue...

Exploring Aunt Julie

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When I was 16 my mother sent me to spend the summer at my aunt's house in the country. She thought it would be good for me to spend some time with her side of the family, I guess. My aunt was divorced, in her late 30s, and had three sons older than me. Problem was, they no longer lived at home and were never around. So I spent all my time by myself or hanging out with Aunt Julie. I helped her out with her vegetable garden and lawn work. Now, I had always liked Aunt Julie. She was...

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Tags: areola, aunt-nephew, masturbate, older-woman

Family Friend Jane

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One summer, when I was 18 years old, my parents went on a vacation. My parents were going to be gone for three months and they didn't trust me to be alone for that length of time. I didn't know how to cook for myself, and I didn't know how to keep the house clean. I had lived a sheltered life where my mom had done all of the housework and I just studied and did my homework. So they had a family friend, Jane, who had just graduated from college, come to baby-sit the house and me. Jane's family...

Female Nurse Takes My Rectal Temperature

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I was 13 years old and that spring I began to develop asthma again. When I was several years younger, I had a mild case of asthma and I was taken to our family pediatrician quite frequently. Because I was entering my teens my mom now switched my doctor to a regular physician and I stopped going to our old pediatrician. I remember that spring day very clearly when my mom picked me up from school and told me that we had a doctor’s appointment, but not at my new doctor. She had made an appointment with my old pediatrician...

Diane And The Lawn Boy

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*** Diane is an attractive older woman with a bit of a problem. She is extremely sexual but she is attracted to young boys. (Fb, ped, voy, oral) *** Diane was lying in her tub with the water pick gently spraying her open cunt. She was older but still good looking and was thinking of her last young boy. She knew that young boys had powerful hormones and, if you didn't scare them away, they were fucking machines. She was lonely now that the pizza delivery boy had moved. Her orgasm was getting closer as she remembered his hard young...

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Tags: older-woman

Dirty Boy

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"Please Samuel, remove your shoes and socks before stepping a single foot in here," Bethany Cannony said to young Sam very matter-of-factly, "we are going into the nicest room in my home you know." As they stepped through the arched doorway, Sam felt very out of place in what was clearly the tidiest and most elegant room he had ever set foot into in his young life. His bare feet sunk into the lush white carpeting as they made their way past the expensive decorative lamps perched upon antique marble tabletops. Delicate glass menagerie hung from display stands on delicate...

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Tags: doctor, humiliation, medical, older-woman

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...

Doing it for a Younger Girl

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I think this must have happened when I was about 12 as I remember it being quite soon after I first started "playing with myself" as I called it then. For years my mother had been a friend with a woman who lived up our street and I had known her and her two daughters for a long time. My mother's friend kept a small holiday chalet on a development by the coast and we regular used to get invited there for the weekend. It was at this chalet that these events took place. My parents and their friends had...

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Tags: masturbate, older-woman

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

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,...

Embarrassing Panties & Garter Belt

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Back in the 60's every young girl couldn't wait until she turned sixteen to have her "Sweet Sixteen" birthday party because that was the advent of her becoming a young woman. Going to a Catholic grade school until eight-grade I had to wear uniforms with knee socks to school and my parents forbid me to wear stockings out socially, remember pantyhose weren't invented yet. So when I turned sixteen I was ready for some wardrobe changes. Vividly I remember that morning of my sixteenth birthday taking a bath to get ready for my afternoon party and as I walked out...

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Tags: humiliation, nylon, older-woman

Enema on the Farm

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We lived on a farm way out in the country where there were not too many visitors and, because our house was set well back from the seldom-traveled road, we had had a lot of privacy. I can remember, when we were preschool and even in the pre-teens, on hot summer days, instead of bathing in the hot bathroom, my two sisters and I would wash up outside, soaping ourselves and then using the garden hose to rinse. We didn't feel too self-conscious about our bodies because we had seen each other nude so often, it really didn't seem unusual....

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Tags: enema, older-woman

Confessions of a Panty Slave

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There are several kinds of boys in this world: those who have masturbated to their sister's panties, those who say they haven't but are lying about it, those without sisters, and those who are sexually dead. I am a member of the rather large first kind. I grew up in the 1950's we didn't have internet then. As a young pre-teen, the best I could do was the girl's section of mom's Sears Catalogue and at least they showed pictures of women and girls in their undergarments. I didn't have a lot of time alone in the house (mom was...

Crazy Handjob

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Back when I was about 13 I started developing quite well for a boy my age and at this age I was already 5'6 and a firm, sturdy 140 lbs. But the biggest change to me was in my cock. I was a solid 8 1/4 hard and quite wide with a large purple head. Guys at school soon noticed and gave me mean nicknames like donkey dong or pipeline Pete. I never gave much thought to my cock size until I noticed girls and even older women staring at my package during the summer between my 12-13th years. I...

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

Cumming in Front of Older Ladies

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A few things before I begin. Noelana (I call her Noe) is a lady I've known for about 7 years. She's 46 but usually acts 26, and rents a house from my uncle. She's about average for her age, if not a bit plump(she's had 2 kids). Over the years I've gotten to know her and her best friend, Lana(I think she's a few years younger than Noe, slightly plumper with a waaay bigger ass), pretty well over the years. We've got an open relationship in that we talk about everything, and can ask each other almost anything. Noe's been...

Curious Boy, Concerned Mother, Seductive Aunt

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While fantasy, this story does contain some truths. And they were: Mother knew all about her son's 'deep, dark secret'. Unwilling to confront him, she turned that unpleasant chore over to her younger sister. Elaine, a three-time divorcee was well versed in the proverbial facts of life. She agreed to help her older sister in this most delicate task. However, after a short discussion with her nephew she concluded that this deep, dark secret was in fact an irreversible life-style decision that was quite harmless. In her opinion, she saw nothing wrong with it. Indeed, he had an open invitation...

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