older woman sex stories – Page 13

Johnny Gets Spanked part 4

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They walked over to a corner of the locker room and she picked up a large plastic garbage bag that was at least half full. She continued back into the training room and walked up to the table. With little ceremony she up ended the bag onto the table and emptied out a bounty of women's intimate garments. He stared wide eyed at the collection of panties, bras, slips, and other items. There were light pinks, blues, yellows, hot red, evil black and even a tiger striped kind of soft one piece bathing suit garment. The gym teacher turned and...

Julia (part 3)

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If you have read the first two Julia Stories, you know that Julia, an older woman, and friend of the family, had been really allowing me to explore my interest in women and their sexy undergarments, and had finally given me my first blow-job as a 15th Birthday present. Thats where this story begins. The day after the blow-job, I came home from school to find out that Julia wanted me to come over and cut her grass. I practically ran the whole way to her house, hoping there would be a repeat of the previous day's events. When I...

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

Julia Modeling (part 2 – The Pink Panties)

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Modeling pink leads to some real kink As was revealed in part 1 of this series my Mom's friend, and my sex-buddy Julia had modeled a new pair of panties she had been hired to model for a retail catalog. She still had two more pair to show me, and the very next day I was rewarded with the second pair. I got home from school and Julia had left a message on the answering machine asking me to come over to help move a few more boxes. I arrived to find Julia wearing a pair of tight fitting black...

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Tags: nylon, older-woman

In Praise of Older Women

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From the word go I was interested in older women. No, obsessed would be the better word for it. In those days, of course, that meant just about all women, if you disregarded the giggling, barely pubescent girls who seemed from another planet. No, it wasn't them I was interested in - it was their older sisters and mothers, and the mothers and aunts of my friends that fascinated me. Take Dougie's mum - and my fantasy was to do just that. Dougie was my best friend in Que Que (pronounced Kwe Kwe), a town on the main...

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Tags: masturbate, nightgown, nightie, nylon, older-woman

I Was a Teenage Panty Thief

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Rustling in my covers one September morning prior to school, I discovered my manhood for the first time. Rigid. Inconceivably large. I was fascinated. Tentatively, I explored myself, amazed by the myriad sensations, stunned by what was happening to my body...until, quite unexpectedly, I found bliss. A sensation like no other. A shocking warmth burst in my chest and spread to my extremities. I sank into my sheets, spent and ecstatic. I had no idea what I had just done, but I knew with absolute certainty that I would rush home after school that day and do it again and...

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Tags: anal, anus, nylon, older-woman, panties, panty-fetish, rectal, rectum

Jamie Learns His Lesson

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(femdom, spanking, forced nudity, voyeurism, forced panty-wearing, older women) After getting kicked out of a Swiss boarding school for smoking cigarettes and stealing, Jamie had been sent by his parents to a day school in Kent, England for his junior year and placed with a widow who rented an extra room in her home for the occasional foreign student. Mrs. Constance Worthington was a kindly but no nonsense woman in her mid-forties living on a small pension since her husband died in a car crash five years earlier. Unfortunately, Jamie's bad...

Jason Is Caught In His Mother’s Undies

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*** Jason, at 14-years of age, one day wandered into his mother's bedroom and, looking through her dresser, his world was suddenly turned upside down as he picked up and eventually tried on his mom's panties and bras, one set after the other. He didn't expect mom to come home and catch him, but she did. Mom was divided on how to deal with her son's activity. (Fm, ped, inc, cd, mast, oral, 1st) *** When Jason was only five, his father Troy was killed in an automobile accident when a 47-foot long, 18-wheeler ran a stop sign and struck...

I Like Knickers

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I am a big knickers lover, especially the navy blue school knickers, and directoire knickers. As a lad I use to live with my auntie and her daughter. She was a few months older than me, and she used to let me put my hand up her skirt and feel her knickers as we sat and did our homework in the kitchen. I really enjoyed that, and would get a bit excited, to the extent when it was bedtime I would go the basket in the bathroom and get a pair of knickers, and take them to my room. There...

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Tags: directoire-knickers, older-woman

Helen’s Hot Boy Lusts

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The Summer heat hung deep on the small town of Riversdale and young 12 yr old Randy could not wait to finish his summer lawn mowing job at Mrs Henderson's. He had been hired to mow the grass twice a week but sometimes wondered why they had not hired an older boy because he was still quite small and struggled on the uphill parts of the lawn. Randy was a perfect specimen of a boy - lithe and almost girlishly beautiful with blonde hair in a center parting and golden bangs over his forehead. Just 5' 2" tall and about...

Helping Aunt Breast Pump

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Kenny Morgan was engaged in one of his newly favorite pastimes - that of fantasizing about his attractive aunt, Nancy Belding. His first recollection of being attracted to his mother's younger sister had come only recently. now as a student in junior high, his head was swimming with thoughts about his lovely aunt even though he only saw her infrequently. His aunt, who was in her mid-thirties, was an attractive woman with light brown hair who had what Kenny had observed to be a spectacular figure and shapely legs. She also had nice boobs, or so he...

Her Bedroom

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I grew up in a small mid-western town, in the far north snowbelt. My mother, like most of the women in the town, wore jeans, flannel shirts, sweat pants, and athletic shoes most of the time. The only exception was for Church, then I might see a few women in dresses and heels. There were no real "fashion plates" in the town. Except then came Marge. She was a rather plain looking brunette, about 5' 6" tall, but she had a fantastic figure. Marge had grown up in Chicago and moved, as an adult, to our small town because her...

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Tags: nightgown, older-woman

Holiday At Auntie Joan’s

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May I start with a little introduction; I am 33 years old of average height, average build, wear glasses and would pass by in a club without much of a fuss. May I also point out that I am adopted so any liaisons with family members are not strictly incest? Since my interests in the fairer sex go back into my earliest memories, I thought that the others of like mind out in the vast underbelly of this beast we call the internet would enjoy a quick resume of my past and contact me with comments and perhaps opportunities to...

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

Home Alone with My Mother-in-Law

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Daughter invites her MILF of a mother to stay with her and her husband. After losing her job as a waitress and unable to afford her rent, sexy things happen when Audrey comes to live with her daughter, Jennifer, and son-in-law, Daniel. Unaware that her husband has been sexually lusting over her mother and her mother has been sexually lusting over her husband, Jennifer invites her mother to stay with her and her husband until she can get a job and get back on her feet. Note: Being that a son-in-law is not blood related to his mother-in-law, normally having...

Home Care

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There are certain things that I think we all take for granted, at least for some time in our lives. Well, I had one of those things taken from me, and it wasn't fun, except for what Ginnie brought to me. Let me explain. I live in a large city, and in a large apartment building with many tenants on each floor. So what we trade off for volume, we get some amenities. It is a nice building with kept grounds, indoor parking, and security. That's important to many of us the this growing climate of danger of being shot...

Hooked on Panties

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I have been hooked on panties since I was a child of about 7 or 8 and was forced to wear my mother's panties to school one day after I had wet the bed wearing my only pair of clean undershorts. I went to school feeling very embarrassed and bad for having made my mother so angry. I also must have felt angry at her for having made me wear her nylon panties, and was terrified that some of my friends would somehow find out and laugh at me. Of course they never did, but I felt as though they'd...

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

Hotel Paradise

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'So there we have it,' said the manager of the Hotel Paradise. 'Your son has admitted the theft and Mrs Crenlee told us all when she caught the boy in her room she wants justice. I have no choice but to call the police.' To the horror of the three people sat opposite him the man reached for the phone on his desk and started to dial. 'No, wait,' said Jon Owens, getting to his feet. 'Surely we can work something out. We can talk to Mrs Crenlee about compensation.' The manager stopped dialing and looked at the worried man...

Hot Neighbor

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This is an account of my earliest, and most vivid, sexual experience. Although intercourse never occurred, it was, for a just-13 year old boy, very sexually exciting. I can remember it as if it happened yesterday, because of how it affected me. As I mentioned before, this happened twenty years ago when I was thirteen. I was an only child and I had been to a few `make-out' parties, but the only sexual contact I had had with girls was the usual kissing and maybe a feel of little budding breasts through a t-shirt. Of course, I'd learned to...

House Arrest

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It was only a few weeks since ten year old Randy first jacked off. His friend showed him how to whack his Willie and thereby have this incredible sensation, his friend having himself just learned the trick from his older brother. The very first time that feeling swept over him, it frightened Randy, thinking that he was about to go blind or even die or something. But he didn't die, he just felt... well, incredible. When he realized that he hadn't died, gone blind, and that nothing terrible had happened, he naturally wanted to do it again, and each time...

Housewife Teases Phone Workers

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It was a hot summer day, Linda was home alone, and she was horny. Her children were visiting their cousins, and her husband was at work and not expected home until late tonight. Linda really wanted something sexual to occur. She hadn't had sex with her husband for a while, and hadn't even seen another man close-up for days, it seemed. Linda peered out the windows, hoping to see a neighbor out working. She was praying to see a man without a shirt on, anything that she could fixate a fantasy on, and spend some of the afternoon playing with...

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Tags: areola, older-woman

Granny Knows Best (ch.10)

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Hayley wandered home, her mind full of contradictions. Biology was telling her that she was young, fit and fertile, and that this was the time to mate - she didn't realize the cause, but she was filled with the powerful urge. Economics was telling her that she was still a dependent, a child who was years from being able to lead an independent life - pregnancy would be a disaster. Her peer group was beginning to drop heavy hints that things were progressing between them and their boys - several girls had admitted to having 'done it', although none...

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Tags: anal, anus, doctor, enema, medical, older-woman, rectal, rectum