older woman sex stories – Page 4

The Truth, The Whole Truth & Nothing But The Truth

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This is a true story, although it happened many years ago, I remember it as though it was yesterday. Only minor details have been changed to protect identities. It happened to me when I was 21. I was still living at home with my parents at the time. My sister (Kelly) who is 3 years older than me, left home and got married (to Eddie) at the age of 17. Kelly had a gorgeous little girl called Amy who was 4 years old. I often visited my sister on a Saturday afternoon to see my niece and play with her,...

The Shooter

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First of all, I am not some super-endowed stud who can perform sexual feats of porn-star proportions. I am fairly normal in size, but maybe thicker and with a large penis head. This attribute has lead some partners that I have been with to say that I am well-endowed, something that 5 minutes of viewing adult video proves to be false. However, if there has been one part of my physical sexuality that has intriqued some women in the past, is the intensity, volume, and distance of my ejaculations. Thus, since I live in a small town and have had...

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Tags: older-woman

The Strict Aunt

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Aunt Cecilia had lived alone until the day her sister died in 1955 she was forced to take in her sixteen year old nephew. She enjoyed living alone and was not offended by the term old maid or spinster, she enjoyed her job as a librarian and thought a good book and a hot coffee an enjoyable evening. At 43 she was still quite attractive but considered plain due to her glasses and the way she wore her hair tightly bunched up in a bun and also for her penchant for tweed skirts and sensible shoes. No freedom was given...

The Surprise Blizzard

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We open the scene in the early morning of a non-descript February weekday, in a house 90 minutes outside of Boston Time was just 6am. James and Wendy were in the kitchen, The Television was on the local new show the hosts were asking the weather guy about today "A picture perfect day ahead folks details at 17 minutes after the hour." Wendy was dressed for the day. So Wendy was organizing the kids things for school, She was so busy that she didn't notice that James Sr. was wearing a long Tee shirt and Jockey shorts as he was...

The Scavenger Hunt

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*** A young man overcomes his lack of confidence by using a scavenger hunt ploy to introduce himself to widowed mature women. (Fm-teen, inc, 1st, anal) *** From the Journal of Damon Wentworth as Augmented by Katrina Ruza Prologue The events of the year 1992 culminated with a birthday party for Damon Wentworth at my home. In addition to celebrating his 19th birthday that evening we were marking the end of a one- year pact we three mature women had with Damon. The pact came about through an ingenious naughty mission this young man through a very clever scavenger hunt....

The Seduction of Aunt Jodi

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John just turned eighteen and it being the start of summer he was home reading the want ads cause he still didn't have a summer job. His mom and dad both just left for work and he was sitting at the kitchen table wearing only his jockey shorts. His tanned fit body had matured quite a bit since puberty and he worked out all the time. John liked the looks he got from all the females at the beach or the gym where he spent most of his time. He always was able to seduce some young fox into sharing...

The Older Woman Next Door

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This story begins when I was a Senior in school. I was your typical 18 year old . I loved to go to parties and like every kid my age, I tried to get laid. I never was successful, so I had to resort to looking at dirty pictures in a magazine and jacking off. Life was unfair, but when our new neighbor's moved in, my life was about to change. The family consisted of Mom and Dad and one little guy of 3. Mom's name was Barbra and as I learned later, she was 41. Her hair was long...

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Tags: masturbation, nightgown, nightie, nylon, older-woman, satin, stockings

The Panty Teaser

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I think everyone, well, every guy, has a partner in their memory that they just never quite got to have. Not the way they wanted anyway. Mine was Debbie. A beautiful and petite brunette. She had what I would describe as close set eyes which ran in the family. She was so short she seemed to be, like, a little girl to me. Smart as a whip but innocent in a way some girls are. I met her in high school and we got together very quickly. I kissed her on our second date and, on the third, she...

The Paperboy

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The best job I ever had was that of a newspaper delivery boy. I did this job for 6 years-from age 10 till age 16 (I lied when I first took the job and told them I was 12). It was hard labor to be sure, hauling pounds upon pounds of newspapers from one household to another- especially for a 10 year old. But it had its benefits. Who knew that suburbia could harbor such perverted secrets? I didn't start to catch on till I was about 13 years of age (three years, utterly wasted!). As the hormone changes kicked...

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

The Party

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When my girlfriend and I first got together, we were rather naive in the way of sex. Of course, experimenting is the best way to go, and as we found out, we loved everything sexual, and I mean everything. Our sex life was an open affair for us. Light touching and caresses in public were not out of the question either. A lot of this was due to the watching of pornographic videos, with us experimenting at the same time that the video was running. Of course, my girlfriend was an exhibitionist. She loved to wear short dresses or tight...

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

The Plumber’s Apprentice

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I have had a panty fetish since an early age. I had a playmate whose mother thought nothing of it to run around the house in her bra and panties, and of course my imagination ran wild seeing her in sheer panties. She was young and very pretty and had a nice body and a somewhat large but firm butt. I stole my first pair of nylon briefs from her laundry hamper and engaged in many sex adventures with her using her yellow, slightly stained briefs and a wild imagination. Kenny who is her son never knew that I wanted...

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Tags: nylon, older-woman, panties, panty-fetish, stockings

The Masseur

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It's been a fantasy of mine that we have talked about numerous times over the last few years. I would love to watch my wife seduce and make love to another man. Since I am avid voyeur, the curiosity is natural. My biggest question though is how I would feel if and when we ever crossed that line between fantasy and reality. We toyed with the idea many times as she flirted and teased with men she met at a local nightclub, but we were always hesitant to invite any of them back to our house. Tina is a very...

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Tags: older-woman

The Neighbor Lady

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I was seventeen and had the requisite experience with an older woman. I used to mow my grandparent's lawn every couple of weeks when I was a teenager, and like all teenage boys my hormones raged, leaving me in a constant state of horniness. I'm my father's son in that respect. I have a half sister in Australia because my dad was one horny fucker, and dear old dad passed his proclivities on to me...which explains a lot about my love of fucking. Like father, like son. I learned how to love to fuck at a very early age. Anyway,...

The Office Slut Ch. 01

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The Start of things. The whole thing started with a discussion among a group of us in the rest room at Hinkerman's, the company where I worked in the typing pool. It was all about how far you would be willing to go for money. It had started with a reality TV program that had been shown the previous evening, where girls had been offered money to flash their boobs in public. The shows presenter could have offered the girls up to £100, but it was surprising just how little he got away with. There was one especially attractive young...

The Office Slut Ch. 04

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Martin rang me on Sunday to enquire how I was, which I thought was nice of him. He said that he had spoken to his farther and he had suggested that I take a few days off to get over Friday. I thanked him and said that I was OK, but he insisted, so I did not return to work until Thursday. It was a good idea, because when I returned to work, I was feeling much better because of the rest. The marks and bruises on my body had gone, and down below, things were back in full working...

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Tags: humiliation, older-woman, satin, stockings

The Job

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Several years ago I worked for a company in a major city. I started out as a temporary worker because the firm was waiting for some positions to open up before hiring any more permanent employees. I really enjoyed the place because it was interesting high-tech work and the people were friendly. The pay as a temp wasn't really great but the prospect of being hired in permanently was an incentive enough to stick with it. After six months, the day I'd been waiting for came. I was asked by my immediate supervisor to report to our division vice president...

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Tags: masturbation, nylon, older-woman, stockings

The Gym (The Beginning)

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(A continuation of My Mother in Law) By Bob As truckload after truckload of used lumber arrived, George divided the loads into three piles. The crap consisted of broken or split boards and lumber full of nails. Good stuff, consisting of good dimensional lumber with few nails in it. And the best, lumber and boards free of nails, plywood sheathing and anything that George thought that he could use for Gladys's workout area. The pile of the best stuff was moved from outside into the barn after sorting through each truckload hiding it from Pete. While George looked after sorting...

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

THE HAY LOFT

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I couldn't believe it; I'd just filled the small gas tank on the top of my In-law's small lawn mower for the second time this morning and I hadn't even made a dent on their tall over grown yard. Pushing the lawn mower back out into the yard where I'd left off I pulled the rope to start the machine. The going was slow and tedious because their grass was so long and thick. I had to slowly push the lawn mower into an uncut area and patiently wait while the blade chewed away at the lush green grass. The...

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Tags: anal, anus, forced-nudity, nylon, older-woman, rectal, rectum

The Ice Storm

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This story is absolutely true which you will no doubt believe when you read it. Nothing really happens, there is no plot, just an attempt to describe the wonderful experience I had one night as a youth. Our winters are somewhat mild here in Kentucky but we do occasionally have a small blizzard or ice storm. One of the later fell one January day when I was twelve. The roads were impassible for three wonderful days and school had already been cancelled. In anticipation of the storm my mother had bundled me and my brother up and taken...

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Tags: masturbation, nightgown, older-woman, satin

The Drive

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A few weeks ago my mother in law's cousin Beth died after a long illness. The burial was to be in her home town about a 3 hour drive from us. As my father in law, Frank, was now confined to wheel chair, I offered to drive them both to the funeral. On the morning we were to leave, Frank decided he did not feel up to the long drive there and back in one day. As I had to be back as work the next day it was decided that only my...

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