older woman sex stories – Page 13

Landlady Love

★ ★ ★ ★ ★

0 average (0 rating(s))

"Age is not a barrier...Many a good tune is played on old fiddles" I can still remember the first time I found out what it was to be a man. I guess I was about eighteen at the time and living in a rented room somewhere in the city. My landlady, who I had always referred to as Mrs. McLaren, had been kind enough to take me in at a reasonable rent when she found out that I was struggling through university. That was eighteen months ago. My studies had kept me from pursuing the pleasures of female flesh so...

Laundry

★ ★ ★ ★ ★

0 average (0 rating(s))

I was sorting out the dirty clothes in the laundry basket, and came across a pair of my panties. I usually go for black cotton 'tangas' although sometimes I wear black lace 'bikini' briefs. Just because I'm 45 I don't see why I shouldn't look sexy - although to be honest no man has actually seen me in my underwear for a year or two. My only child, Robert, who's 16, doesn't count - or so I thought. The panties in question were screwed up into a ball. I tried to open them out so they washed better and discovered...

Laundry Day

★ ★ ★ ★ ★

0 average (0 rating(s))

Chris stood a little back from the wooden fence and watched the children walking to school. Most walked in pairs he noticed. Some carried lunch pails or books. Many had those backpacks slung over one shoulder. He was grateful they were too busy laughing and watching each other to notice the naked man tied to the clothesline in their neighbour's backyard. The fence with its thick, angled boards worked well to hide him. Chris sheltered behind the fence, knowing he was not invisible. He could feel the blush rise in his cheeks each time one of the kids looked in...

READ MORE

Tags: humiliation, older-woman, punishment

Kathy

★ ★ ★ ★ ★

0 average (0 rating(s))

By Bob Because Kathy was unable to get around I offered to stay and help her out. She wanted to pay me for fixing the porch but I refused any money from her. "Oh please Bob, take this money; you worked hard fixing my porch. If it wasn't for you, I don't know what I would've done." She begged. It was hard for me to take the money; sure I fixed her porch and what have you but if I'd been looking out in her interest in the first place she wouldn't be lying there on her couch with her...

Johnny Gets Spanked (part 1)

★ ★ ★ ★ ★

0 average (0 rating(s))

John was perplexed. The teacher had just handed him a note, that a senior girl had brought into class. He looked at it briefly but couldn't quite believe it. This was bad, really bad. As bad as he could think of at the moment. The chemistry teacher was reminding them of their quarterly paper, which was due in two weeks. He shook his head; he hadn't even started it yet. The loud tone that signaled a period change went off. He looked at the clock and confirmed it was 1:30, the end of today's school day. As the other students...

READ MORE

Tags: nylon, older-woman, punishment, spank, spanking

Johnny Gets Spanked (part 3)

★ ★ ★ ★ ★

0 average (0 rating(s))

John slept little Friday night, lying in bed wondering what was happening to him. When he did fall asleep he had another one of those scary but unbelievibly sexy dreams. He dreamt that Ms. Anderson was the head coach of the Cheerleaders and had decided they needed a mascot. She came to his classroom in the middle of the day dressed in a short cheerleader skirt and tight sweater that emphasised her breasts. She anounced to the whole class that "little Johnny" was to be their new mascot. Everyone, especially the girls, laughed at him and Ms. Anderson grabbed his...

READ MORE

Tags: anal, anus, humiliation, older-woman, punishment, rectal, rectum, spank, spanking

Johnny Gets Spanked (part 4)

★ ★ ★ ★ ★

0 average (0 rating(s))

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)

★ ★ ★ ★ ★

0 average (0 rating(s))

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...

READ MORE

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

Julia Modeling (part 2 – The Pink Panties)

★ ★ ★ ★ ★

0 average (0 rating(s))

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...

READ MORE

Tags: nylon, older-woman

In Praise of Older Women

★ ★ ★ ★ ★

0 average (0 rating(s))

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 train line...

READ MORE

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

I Was a Teenage Panty Thief

★ ★ ★ ★ ★

0 average (0 rating(s))

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...

READ MORE

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

Jamie Learns His Lesson

★ ★ ★ ★ ★

0 average (0 rating(s))

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 habits followed him to Kent where he was caught stealing a shirt from a small clothing store run...

Jason Is Caught In His Mother’s Undies

★ ★ ★ ★ ★

0 average (0 rating(s))

*** 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

★ ★ ★ ★ ★

0 average (0 rating(s))

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...

READ MORE

Tags: directoire-knickers, older-woman

Helen’s Hot Boy Lusts

★ ★ ★ ★ ★

0 average (0 rating(s))

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

★ ★ ★ ★ ★

0 average (0 rating(s))

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...

READ MORE

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

Her Bedroom

★ ★ ★ ★ ★

0 average (0 rating(s))

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...

READ MORE

Tags: nightgown, older-woman

Holiday At Auntie Joan’s

★ ★ ★ ★ ★

0 average (0 rating(s))

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...

READ MORE

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

Home Alone with My Mother-in-Law

★ ★ ★ ★ ★

0 average (0 rating(s))

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

★ ★ ★ ★ ★

0 average (0 rating(s))

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...