older woman sex stories – Page 6

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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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...

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...

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...

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...

Rick and Caroline part 8

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I was alone in the young couple's home, Rick was away in Chicago, and Caroline had gone shopping. I had only been over to the house once since the pool party. So to get caught up on what was happening if anything I unlocked the desk drawer and took out Caroline's diary. There were a few entries expressing her concerns about several of the male executives phoning her and graphically describing her vagina and naked body. They thanked her for allowing them to see all of her hidden charms and assured her that the next time they met they would...

Rick and Caroline part 9 (part 1)

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by Bob ************ Note: This story contains scenes of non-consensual sex. This is a work of fiction, and is only intended to be read as a fantasy. Just as some women have fantasies of rape, but would never actually want to be raped, this story is only a fantasy and neither the author, nor the site on which the story is posted, would condone these acts in reality. If you are offended by this type of fantasy please DON'T READ THIS STORY. ************ As August wore on I didn't have much work at the young couples house. We were waiting...

Rick and Caroline part 9 (part 2)

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By Bob While I was in the basement watching the Avon lady thrilling herself with Caroline's young body, I could hear the distant rumblings of thunder. After I watched Larry follow the Avon lady down the dead-end street I hurried outside to dismantle my camera fearing it would get soaked in the approaching storm. I packed up the sound equipment and left it by the door. Caroline was passed out and it'd be hours before she would come to. My curiosity got the better of me and I took a walk down the dead-end street. Approaching Kathy's car I slipped...

Sammy’s Hot Summer Ch. 5: Strike a Pose

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When I arrived at the front door at noon the next day, Thursday, there was no answer. So I went around the side of the house, back to the pool, thinking that was where I'd find the lovely "Busty Bethany", a web model who'd moved in next door to me less than a week ago, and who'd already managed turned my 13 year old world upside-down. Her car was parked in front of the house, so I assumed she must be home. After all, she was the one who'd specifically told me to show up at noon. Yet as I...

Sammy’s Hot Summer Ch. 6: New Developments

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That night, I had a strange dream. In it, I was sitting on the couch late at night, watching TV. I heard a noise upstairs, like something pounding. I looked around for my baseball bat, and could only find a tiny one I'd received during "Bat Day" at a Phillies game once. Stupidly believing that it would protect me, I ventured up the stairs. The noise grew louder, and I promptly realized it was coming from behind my parents' door. Dreading what I would see -- my parents having sex or something -- I was nonetheless unable to help...

Sammy’s Hot Summer Ch. 7: Personal Growth

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The next morning, I woke up with a woody. This, of course, wasn't really unusual. After all, I was 13 years old. Any morning following any night that I didn't have a wet dream -- and even some when I did -- I could count on having a rager in my underwear as I rolled out of bed. The usual result of this was that I'd have to stand over the toilet for at least five minutes, waiting for my erection to die down, so that I could take my first leak of the day. It was a ritual...

School Days

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Reilly woke up early that morning and quickly showered and dressed in his school uniform. He was a freshman at St. Mark's Academy for Boys, and, although his studies were progressing nicely, he was still homesick. It was November, and he had been away from home for over two months. He had always been an excellent student in grammar school and, from his earliest years, had been something of a teacher's pet to the nuns at St. Stephen's. Boarding school was a new experience, however; he missed his mom and sisters and, although he never would have dreamed it before,...

School Daze

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School Daze - Chapter 1 - Assistant Principal I' m a teacher at the local high school. A few weeks ago we had a problem, to many students were cutting classes. While this is normal for students, it had reached epidemic proportions at our school to the point where our budget was at stake. If we didn't correct the problem soon, we could be out of jobs. After trying several solutions, none of which worked, the Principal approached me for advice. After a little discussion, he allowed me full authority to proceed with any ideas I might have. Although I...

Sensible Shoes

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I am a shoe salesman. I work at GERARD'S, which is a small up scale independant shoe store in west L.A. We sell women's shoes, and, in order to compete with the big stores we have to give the customers reasons to come in to our store rather than going to the competition. One of those reasons is our policy of service to the customers. The boss says, "Treat 'em like they just bought a dozen pairs, whether they ever spend a dime or not." That meant measuring every foot, and helping them on and off with shoes, which means...

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

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

Reaping the Benefits of a Drinking Sister and Mother

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Terri sighed. Here was another Friday night, and the fifteen-year-old was stuck baby-sitting her brother again! By all rights she should be out with Bobby Flynn right now! Specifically, she should be in the back seat of his beat-up old car, with her legs up in the air while the twenty-year-old college student used up three packs of condoms giving her the pounding she craved! She had grown so used to Bobby bitching about using the condoms, that she considered it just a part of foreplay. Despite all his begging to go bareback just once, he was scared shitless at...

Rick and Caroline part 3

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The next morning Caroline greeted me at the door wearing the shirt to Rick's pajamas. She had on a pair of feather trimmed high heel slippers. As she walked up the few steps into the kitchen I saw the bare cheeks of her ass. "Coffees ready!" She said, placing a cup on the end of the table where I usually sat. I could smell the bacon cooking in the frying pan. "RICK! Rick your breakfast is ready!" She called out lovingly to her husband. "I'm so hungry I could eat a horse!" Rick said coming into the kitchen. He was...

Rick and Caroline part 6

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Caroline greeted me at the back door after I'd knocked twice. After my outing with the three women my night of appreciation, I didn't know what to expect. She seemed happy to see me as she pushed the door open for me to enter. Caroline must have been in the shower, her hair looked damp and I could see that she'd just started to apply some make-up. She wore a vividly sheer black top; it was a small jacket of sorts. With a single tie just below and between her breasts. From the join between her breasts (that just screamed...

Peter File #11

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In which Nurse Collins recruits Peter for a demonstration of patient care procedures. Editor's Note: Every practicing nurse is well aware of the involuntary sexual arousal experienced by many male patients receiving enemas. The symbolically submissive posture of the enema recipient, the forced exposure of private parts of his body, the sense of personal invasion, and (most importantly) the intimate pressure of the warm enema fluid on his sensitive prostate gland often produce a sexual response in the male. Although the response is harmless and entirely involuntary, and usually goes away as soon as enema delivery is completed, many men...