older woman sex stories – Page 2

An Indecent Aunt

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Tommy Parks could barely believe his eyes: as his Aunt Jennie stooped over in her garden, Tommy could see her butt. Not just the shape of it; his aunt's cut-off jeans shorts were on so loosely Tommy could see from her mostly bare back all the way down her crack. The more she bent over in front of him, the more creamy white ass flesh he could see. Tommy tried not to let his aunt see him sneak furtive glances down her smoothly shaped backside; as he peered he could see, much to his surprise, that his aunt wasn't wearing...

Physical Exam for Football

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I had to get a physical in order to play football at my school, but I got a lot more than a physical. It was 1972, I was 11 years old, and going in the 6th grade. I wanted to play football on the school team and in order to do that, I had to take a physical. Because I didn’t have a regular doctor to go to, my mom just looked one up in the white pages and made the appointment. We arrived at the appointment a few minutes early so my mom could fill out paperwork. While she...

My Son and My Panties (different story, same title)

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I made a discovery last summer that changed the way I think about my fourteen year old son... A few months back I was cleaning up the house and doing some laundry while the kids were out. I opened the door to my son’s room and noticed that there were piles of dirty clothes all over the floor, which didn’t surprise me, but it was a little frustrating because I’d asked him to clean up several times the day before. I started picking up his dirty clothes and throwing them in a pile in the middle of the floor, and...

Mommy Takes Me to the Doctor (ch. 1)

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5 average (1 rating(s))

Part I: Waiting Room As I walked into the doctor's office, following my mother, my head hung down. It hung down because I knew what I would see if I looked up: my mother's unbelievable body, encased in a tight business suit. If my eyes drifted upwards, I'd see her tiny, 4-inch-heel-encased feet, her curvy, tight legs, her full, slightly swaying ass. And, framing her petite torso, her gigantic, round breasts. Yes, from the back. Her breasts were so massive that the poked out from either side of her body. At 5'3" - in those heels - she was completely...

I Tricked My Busty Step-mom (part 3)

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There are three things that make a pair of breasts fantastic: 1) They need to be of some substantial size. A very full C cup up to about a maximum of a DD-cup is just about perfect for a pair of hungry hands. Well, there's always the exception of a very thin Japanese woman with E-cups, but I digress..... 2) They need to be firm and have a great shape to them. They can't hang somewhat flat lacking shape, no, no, they must have a solid roundness and fullness like a pomegranate, or a firm teardrop shape, like a pair...

I Tricked My Busty Step-mom (part 2)

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So, I got my busty step-mom Becky to parade around the house half-naked with her tits jiggling, squeezed up with her bra stretched down below them. They were bouncing around like some firm platters of jelly waiting to be gobbled up, exposed and tempting as hell and she was doing it just as I had asked her to do. The way the bra, pushed up from below them, made them look as if someone had both hands around the base of each of them, squeezing them so they bulged out so smooth, round and firm, with their thick nippled-tips jutting...

12th Birthday Medical Exam (part 8)

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In Chapter 1, we met Family Practice Doctor Marcy Harris. The 54-year-old woman with two grown sons of her own was a respected Doctor who gave thorough exams. In the first six chapters, she examines several boys of varying ages, and in Chapter 7, she hosts a charitable day in an underprivileged neighborhood and uses one of her nurses" sons to demonstrate how to properly examine and spank a young boy to a group of moms and guardians. Erica Jimenez was one of the women attending Dr. Harris's presentation that day after seeing a flyer on her college campus. While...

12th Birthday Medical Exam (part 5)

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In chapter 1, we met Family Practice Doctor Marcy Harris. The 52 year old woman with two grown children of her own was a respected Doctor that gave thorough exams. In the first four chapters, she examines two boys, Kyle Roberts and a new patient Michael Sanchez, 11. Our story continues with Dr. Harris seeing a patient, Wayne Andrews, a boy that she has known since he was one year old. Wayne Andrews had very mixed emotions this summer morning. On one hand, the boy was excited to be on summer vacation and it was his 14th birthday. On the...

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Tags: anal, anus, doctor, humiliation, medical, nurse, older-woman, rectal, rectum, spank, spanking

She’s Moving Away – 1

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5 average (1 rating(s))

Marilyn, the woman who lives next door, has always fascinated me. She's not a world class beauty, has a few wrinkles and is a little over weight but attractive to me none the less. As an empty-nester couple, she and her husband are involved with their church and a few civic and neighborhood projects as volunteers. I've been out to dinner with them a few times. Love her... can't stand him. He's a professional, religious snob. When I moved in about eight years ago, she and her husband welcomed me with a pot of coffee and some homemade bread. Her...

She’s Moving Away – 2

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*** Further adventures with my sweet, older, well endowed, married neighbor, Marilyn. What a sweet, innocent hottie. What a remarkable Fuck Toy. (MF) *** A short while back I wrote a story I called, She's Moving Away, that you may have read on this website, about the incredible, serendipitous, sexual adventure I had with a sweet, neighbor lady named Marilyn. Sweet Marilyn is an older woman on whom I've always had a crush. For years I would secretly gaze at her, from my house, as she worked in her yard and often fantasized various erotic scenarios that included the two...

Mrs. Peters

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"Hi Mrs. Peters, is Rick home?" the young man asked as the very pregnant Mrs. Jane Peters answered the door. "No Kevin he's out with his dad" she said rubbing her swollen belly. "Come on in though, they should be back soon and you can keep a beached whale company." Entering the house the boy replied "Your no beached whale Mrs. Peters" "Well Kevin I certainly feel like one. Only a few more weeks until I deliver and I really can't wait." She said engineering her way onto the love seat. Kevin sat across from the pregnant Mrs. Peters. Before...

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Tags: big-boobs, mommy, older-woman, older-woman-boy, pregnant

A Computer Nerd Gets Lucky

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I had always been a bit of a nerd and being a dab hand with a computer just confirmed it. The school year had finished and I had six weeks to kill before Six Form College started. I was eager to get out and earn some money; with there just being mom and me, things were a bit tight at home. Therefore, I decided that it was time I went out and earned my keep. I was always fixing computers for my school friends, and it was one of them that suggested that I try to make a few pounds...

The Lady Next Door

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Fresh out of college, I had just joined a rather large company. I had worked hard for my degree, and I was approached by a number of large firms. I decided to join one that was going to send me to a desert city in the Southwest. The company arranged for me to move, and in the process, I found a rather unique nearby community. It was a mobile home park, situated out in the desert. The first thing I discovered was that it was very, very hot in the desert. There was a pool at the mobile home park,...

Mum’s the Word

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1 average (1 rating(s))

CHAPTER ONE You're going to think this is a sad story, because it starts out sad. But don't be sad for long, brothers and sisters, because it ends up pretty OK, at least to me it does. I'm Bobby, by the way, Bobby Henderson. That really doesn't matter to the story, except that it's about me and my mother, Claire Henderson. There are a few other people in it too, but they only matter a little. I'll mention them later. My mom's story starts out like a lot of people hope their adult lives will start, with a good marriage...

Billy and Aunt Karen (part 2)

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The Ties That Bind His Aunt Karen was attractive, somewhat independent and ran a household with the efficiency of a military officer. Billy had just turned thirteen, although he still looked more like nine or ten at the time he spent two weeks with Aunt Karen while his mom went with his dad on a business trip. His two older cousins were busy teenagers - more away than home, and she could use the company, or so his uncle had reasoned. His aunt had a very pretty face, a very good figure with pointy breasts and nice legs. And, Billy...

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Tags: medical, nephew, nylon, older-woman, older-woman-boy, stockings

Barbara’s Panties

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I had to attend a convention and it happened to be in the same city that my wife's older sister lives. My wife suggested that I go a day early so I could visit her sister and family. I was going to spend the first night with them and then check into the hotel. I arrived around noon and visited with the family that afternoon. That night my sister in law informed me that she was going to let me sleep in her youngest daughter's room. She said Barbara had agreed to give up her room for the night. Barbara...

Billy and Aunt Karen (part 6)

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Lingerie Show Two days later, Karen Stone and nephew, Billy had sat at the kitchen table for some time. She was working on the household accounts. They had become quite good friends during his stay. Billy thought she was very attractive, but he knew that at his young age she wasn't attracted to him, however Billy was happy just being around his attractive aunt. He had, however noticed that since the second 'tying-up game, his aunt had at first been a bit standoffish. When he had made a veiled reference to her behavior change, she had immediately begun catering to...

Slutty Best Friends

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"Jenny? Jenny, wake up." Jenny's little brother, Kevin, quietly tried waking up his sister from her bedroom doorway. "Huh? What?" Jenny sat up in her bed. She was dressed in what she usually slept in, a thin nightie and panties. Jenny was 14, about a year older than her brother. She had long black hair, was a little short for her age, and although she was still pretty young, her tits weren't very small any more and she had a really nice bubble butt. "Wake up," Kevin repeated. "I made you breakfast." Kevin made Jenny's breakfast occasionally so he can...

Young Lover

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"Shouldn't you be in school?" Jennifer was taking advantage of the warm, spring weather to get her yard in shape. She had been pulling up weeds in her front yard, and for the past 15 minutes, she had had an audience of one. Kevin was the 11-year-old boy who lived next door to her. He had strolled up the sidewalk and sprawled himself out on his front yard. Now, he was lying on his belly with his bare feet kicked up in the air, watching her. "It's spring break," Kevin said flatly, as he pulled himself up off the ground...

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Tags: masturbation, mommy, older-woman, spank

Young Awakenings

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Chapter 1 I was only 12 when it first happened It was pouring down hard and the field was muddy and wet. I had watched the other boys leave one by one. Most of them had parents who stayed and watched the game. The only thing keeping me from mother nature was a thin soccer jersey with my favorite number on the back. I made my way to a wooden picnic table I used to sit under to wait for my mom when I was younger. I crawled under and wondered how I ever used to fit under there before....