older woman sex stories – Page 14

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...

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 masturbate...

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

Hypnotism Hose & High Heels ch. 2

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He heard a voice calling him...calling him from somewhere...urging him awake... "Frank...Frank...are you awake?" The soft voice of his mother, Martha, brought Frank from the land of Nod. He opened his eyes. His mother, dressed in a lavender silk dressing gown, was bending over him. "I am now, Mother," he replied, humorously. His mother smiled at him. "I'm sorry to awaken you, sleepy-head," she teased him, gently. "But it's already past nine o'clock in the morning. Breakfast is still warm, but it won't be much longer." "Nine o'clock...that late?" He glanced at his alarm clock on his bedside table. It...

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 assumed, given how...

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Tags: doctor, hosiery, humiliation, medical, nylon, older-woman, teats

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

Granny Knows Best (ch.2)

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Pete smiled as Granny ushered Mary into the room. Theirs was a long standing friendship - they had been dating for almost a year now, gradually discovering sex together. They had not yet gone all the way, but they were familiar with each other's bodies and sexual needs, and things were moving steadily towards consummation. "Wow, Pete, you look loads better today." They hugged each other self-consciously in the presence of Granny who just smiled faintly at the sight. "I'll leave you two for a while. I'm afraid you can't stay too long, Mary - I want to get Peter's...

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

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 was...

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

Granny Knows Best (ch.12)

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Mary started to undress, but Hayley was suddenly shy and scared, these were deep waters for her. She wanted to get away from the older pair - when Martin was on his own she would tell him that she wasn't ready. She grabbed Martin. "We haven't time for all that now - let's go to your room." She hustled him away, then realized with horror that Pete and Mary had followed them. Mary just casually peeled off her clothes and dived on one of the beds with Pete. Hayley did not know what to do or say - she felt...

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

Great Aunty Lynne

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My grandfather had been ill for a month, he was only sixty-two years old but his heart got a disease that meant he would need a transplant, that was, if they could find a donor that matched him. My father told me to go over to see him in hospital as I was on vacation from school; dad had a bunch of books for me to take to grandpa, oh, and the eponymous bunch of grapes, naturally. I had to catch a bus to the hospital, I had just got my drivers permit but my parents couldn't afford a third...

He Fills Their Needs

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*** An extended family suffers the loss of all its adult menfolk. The 3 generations of women, led by their 57- year-old matriarch, unite and establish a successful life. All that's missing is men partners. Their standards are high and no one qualifies until a little man in their life unexpectedly fills the gap. *** It had been a tragic accident just 3 years ago. At just 10 years of age James had lost his father, grandfather and great grandfather, all in the one car accident as they returned from an agricultural show in the nearby town. Three generations of...

Grandma Em

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In all my years, I had never thought of grandma Em in a sexual way – until the day I walked into their house, yelled for her and got no answer. I could see that grandpa Willie was gone. His Chrysler's absence meant he was either gone to play gin rummy with the guys or he was at the golf course. Either way, I figured she was in the garden fooling around with flowers. As I head to the bathroom, I had whipped out my piss-hard dick, opened the door prepared to lose my pee, when I get shock supreme!...

Grandma’s Big Tits

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She knows he's been checking out her breasts... Colin has been having fantasies about his grandmother's impressive breasts for some time. He fights against his feelings but... Well, read on and see... COLIN GRANT drove through the streets of the town with a weight on his mind. He was worried about the things going around and around in his head. It was getting so bad he was losing sleep, but Colin couldn't stop himself from doing it. He knew, even as he drove to her house, after all the soul-searching and agonizing, Colin knew that when he got there it...