older woman sex stories – Page 19

A Visit to the Doctor (part 1)

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The first time I can remember being totally humiliated was when I was younger. During school one morning, I suddenly came down with a rather bad pain in my mid-back. I was sent to the school office, which eventually called my mom. My mom was sure it was a kidney stone and wanted me to see a kidney specialist that she knew. Since she was at work, she arranged to pick me up on her lunch hour and drop me off at the doctor's office. When we arrived, the doctor's office was empty except for a lone medical assistant. My...

Aunt Paula’s Odd Proportions

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It was a 400 mile drive from my home to the Penn State campus, where for whatever reason they chose to accept me back in 1977, and while I could have made it in one day my mother convinced me to stop en route to spend a night at my Aunt Paula's place. Convincing might not be the proper choice of words because I sort of planted that seed of thought when I asked Mom about the best route to take and she said that Aunt Paula's house was about halfway to the college. "Tommy, I would feel so much...

Aunts’ Lingerie Party

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One Friday night during my senior year of high school, shortly after my eighteenth birthday, I drove to a nearby university, to attend a concert with a friend who was a freshman there. After the concert I was starting the long drive home, when I got the urge to drive past my Aunt Valerie's house. I was half-considering stopping in, but it was pretty late, and Aunt Valerie had two young kids. But when I approached her house, there were a number of cars in the driveway and in the street. I recognized several of the cars as belonging to...

Aunt Sue

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After my parents got divorced, I lived with Mom. She had a good job and apparently was well paid because we never seemed to lack for any necessities. She got a recent promotion, though, and now she has to travel quite a bit. Although she seems to really like her job, having to leave me alone bothers her a whole lot. I'll have to hand it to Mom-- she's very conscientious and seems to worry considerably about being a good parent. More than anything else, she worries that I won't get proper care during those times she has to be...

Aunty Kay’s Silky Petticoats and Directoire Knickers

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My love of ladies’ silky underwear started when I was still at school. I went to a co-educational school and at that time girls wore blouses and skirts for the winter term and then light cotton dresses for the warmer months. They also quite commonly wore slips under their skirts and dresses and I used to spend many a happy time during a boring lesson catching glimpses of their nylon and lace slips and underskirts peeking from under the girls’ skirts. There was one particular girl, for whom I had a burning lust, who regularly wore a lovely, soft, black...

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Tags: directoire-knickers, nylon, older-woman

Aunt Jenny’s Panty Paradise

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A year ago, when I was 15 years old, my parents took a two month summer vacation to Europe, leaving me in the care of my mother's friend Jenny in New York City. Jenny and my mother had met in college, and became good friends, and had kept in close contact ever since. Unlike my mother, who had gotten married, given birth to me, and become a stay-at-home mom, Jenny had moved to New York after college and started her own fashion company. By the time I was 12, Jenny's company was flourishing, and she had become a successful business...

Aunt Karen

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Chapter 1 A Bird in the Hand I was always fond of my Aunt Karen; she was a grown-up for sure, but really not that much older than my sister and I. She occasionally baby sat us and we always had a fun time with her. As I got older and started to have "manly urges," I also noticed that she was a very attractive woman. I thought the world of her. That is, until that summer she spent at my house when she brought that world crashing down around me. I was twelve, and my sister, Carol, was eight...

Aunt Karen part 6

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We were on our way to the mall when Aunt Karen started talking to me about the “rules.” I don’t remember exactly how she put it, but she talked about how she knew we had both been having fun for the last few days and that she wanted us both to feel comfortable and continue having fun. But she was concerned about my being only 14 years old and that certain things were illegal for her to do with someone my age. She said she would feel more comfortable if we set out some rules that would protect us both....

Aunt Karen part 10

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The next morning I awoke before Aunt Karen. I decided it would be best to go to my own bedroom. I wasn't sure what she would remember from the night before, and didn't want to push my luck. I still had Aunt Karen's big white nylon panties on when I got out of bed. So I slid them off and threw them in her closet before going to my room. A couple of hours later, I woke to find Aunt Karen standing over my bed. She was wearing white stockings, a white garter belt, white panties, a big white bra...

Aunt Karen part 11

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conclusion ~This episode concludes this story. If you haven't read the other episodes, I recommend that you read them in the order that they were written, since the story builds to the point it reaches in this final episode.~ As Aunt Karen and her older friend June walked down the hallway toward Aunt Karen's bedroom, I sat on the chair in the middle of the living room, in a state of shock from all that had happened. I began hearing giggling and the clinking of glasses coming from the bedroom. I stood up and walked toward the bedroom door. As...

Aunt Mable’s Visit (chapter 4)

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Chapter - 4 Art took one look at his parents and wished he could sink through the floor. What if they found out his aunt had sucked his cock and he had lapped her cunt. He wondered if they could look at him and tell something important had happened to him. He sure didn't feel the same as he had before he'd lapped cunt and had his cock sucked. It must show somehow and he knew his parents would be able to see it. Art's guilty conscience was getting the best of him. How could they not know what he...

Aunt Mable’s Visit (chapter 5)

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Chapter - 5 Art spent another interminable day in school and ran home without waiting for Sally again. He hadn't jerked off all day and his prick was sticking out like an iron rod. Art couldn't see his aunt and guessed she was up in her bedroom. Just like yesterday his aunt was waiting in her room. Art shed his clothes on the way up the stairs. His aunt got up and met him at the bedroom door, hugged him, kissed him, and rubbed his tongue with hers. His prick was throbbing and he almost came again when his aunt...

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Tags: older-woman

Aunt Mildred’s Secret

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* * * * * “Alvin! Aunt Mildred fell and hurt her back. She’s in the hospital.” Those words started a sexual adventure that is still going on today. About two years ago, my mother’s sister took a bad fall. Aunt Mildred had always been an extension of our mom. Sharon and I were kids to a single mom. Our dad took off soon after Sharon was born. I was three at the time so I don’t remember him. Like I said, Aunt Mildred helped mom in raising us. In fact, she was there more than mom was most of...

Auntie Val

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Like a lot of English lads, my introduction to what lay below a woman's clothes came through the good photography of Mayfair magazine, a very popular British men's magazine and, in my view, a British rival to Playboy. Mayfair sourced photographs from some of the best British photographers of the day and had some of the prettiest British girls at their (naked) best. Some of the biggest names in British modeling appeared on its pages: Jane Warner, Kirsten Imrie, Sam Johnson, and others. The magazine - which was in a similar format to Playboy and contained a number of well-written...

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Tags: boy, lingerie, older-woman, panties, stockings, voyeur, woman

Auntie Eileen

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Tommy hung suspended from his wrists in the punishment room set up by his Aunt Eileen to correct her own daughter's naughty behavior but now used for his benefit. He had been caught voyeuristically spying on his older sister while she undressed to bathe and his mother couldn't tolerate any more of this ongoing behavior so she packed him off to her sister's stern care. Eileen looked at the boy and licked her lips. The 11 year old boy looked innocent, almost girlish with milk white alabaster skin and light brown hair. His shorts hung low on his hips exposing...

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Tags: anal, anus, humiliation, older-woman, punishment, rectal, rectum, spank, spanking

Auntie’s Hot Panties

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I have always loved older women, lingerie, stockings, girdles, panties, and yes pantyhose. For me it started when my family made regular trips to LA to visit my Uncle, who loved baseball, & my Aunt Sue who hated it as much as my uncle loved it. He always had season tickets to the Dodger games. Sometimes a friend of my Grandpa's or my Uncles would show up uninvited and I always had to give up my seat at the game. On this weekend they were having several games from Friday thru Sunday, and a relative from up north came to...

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

Auntie’s Panties

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Sam was a bright, 20 year old, radiant young man. He far surpassed his classmates in their studies. Spending long hours in his room completing assignments working many hours into the night. Sam had a somewhat clumsily hidden secret. Sam had a great deal of interest in the underwear of his mother and aunts. He was obsessed. Swiping clothes from the house's only dryer, walking quietly and containing his excitement. Sam would even go as far as to reach into the drawers on his mother's bedroom furniture. But Sam was putting that behind him now. He was behind in his...

Auntie Alice 3

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We got Alice home sometime late Sunday, she was now moved into Gladys's house using the bedroom where I used to sleep. Everything went well, except moving her in a car was a real hassle. Her broken leg was in a full cast from her upper thigh to her ankle. Her badly broken right arm, was encased in plaster from her arm pit to her wrist. Her other arm, the cast went from below her elbow to her hand, her thumb was immobilized. She was in a lot of pain and on some pretty strong medication, she slept through the...

Auntie and I

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My dick sprang up, hard as rock. My Aunt stood by the mirror in her nightgown, pouting her lips and cupping her breasts, so full and firm, they stood out large, barely keeping inside her lacy bra. Peeking through the door crack, I was trying to keep still, but finding it more and more difficult to do. My Aunt finally moved away from the mirror and to the bed, where she laid down and spread her legs. Every morning it was the same, needing to feel the hot clit against her fingers. As Aunt played with herself, I was getting...

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Tags: anal, anus, big-breasts, huge-tits, nightgown, older-woman, rectal, rectum

Auntie Clem and the Clystere

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Mom and I were having breakfast on the patio on a warm July morning. "Oh, by the way," she said as she buttered her toast. "Auntie Clem is arriving on Thursday." I nearly choked on my orange juice. "She...she is?" "Yes. That's two days from now. I thought I'd tell you well in advance, so you'd be sure to be free for her. She'll only be here through the week-end, and of course she'll want to see you." She smiled, and I blushed and looked down at my food"Oh," I said. Auntie Clementine, my mother's older sister, was my favorite...