older woman sex stories – Page 13

Lingerie Model

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Geoff was thrilled. Sharon's words brought the promise of fulfillment to a fantasy he had recently found repeating itself in his thoughts during their times together. As erotic and satisfying as their sexual explorations had been together, his thoughts often strayed to the idea of bringing a second female into the act. Over dinner, Sharon, an extremely attractive camera technician at the local TV station, told him, that she'd met a young beauty contestant in the course of shooting a story for the station, who wanted her to do a "lingerie shoot" for the girl's portfolio. Anticipating Geoff's interest, she...

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Tags: areola, masturbation, nightgown, older-woman, spank, stockings

Living With Aunt Jane

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What a great year this was turning out to be. I had just completed my internship with a company and was offered a full time job with a sister company in another state. I was excited about moving to a new city , but because of my reckless spending I did not have much money in the bank to afford a big move like this. It was depressing to know that after just turning twenty-five, I did not have much to show for my hard work. I was scheduled to begin my new job at the beginning of the next...

Lady Eleanor

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I had always had a thing for my neighbor Eleanor; she was in her late fifties but had an incredible body for a lady more than twice my age. She stood around 5'8 had legs that went up forever an ass that was big and round and her breasts had to be at least DD's. One day as I was sneaking around my parent's room I went to my favorite spot, my dad's plethora of porn he had stashed in a box deep in his closet. As I tore through the various magazines I came to the conclusion that he...

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

Lady Voyeur Spied on Me

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I have been an avid masturbator since I was 13, and am now a recently divorced 34 year old male. The following experience happened only a few weeks ago. I was home for the day (Friday), off from work to get caught up on things around the house. I recently moved into a small ranch in a quiet neighborhood, and haven't met many of my neighbors yet. After cleaning out the garage and sweeping the deck, I was very sweaty and was about to shower when, on impulse, I decided to sit on the deck nude and have a nice...

Lana’s Adventures

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First, I would like to describe this beautiful creature to you. Lana is a natural blonde with gorgeous blue eyes. She stands about 5'6" tall with a beautiful figure. Her measurements are 38inch Double D cup breasts, a 24 inch waist, and 36-inch hips. Needless to say Lana's soft, firm, natural, magnificent 38-inch DD cup breasts are what she is most proud of. She is a little on the heavy side, however most of her weight is carried in her huge mammaries and in her curvaceous ass. Alot of guys don't care for ladies with a large tush, but if...

Landlady Love

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"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

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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

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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...

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Tags: humiliation, older-woman, punishment

Learning Birds & Bees from Aunt

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When I was 11 my dad died suddenly. An only child, my mom raised me the best she could and worked full time, but times were tough. Fortunately my dad's sister, my Aunt Pam, lived in town and she was very helpful to me and my mom. I spent quite a bit of time with her in my teen years, and many days after school I would go there instead of home, and would often stay the night when my Mom worked late (she had a second job as a waitress). As I turned 13 I was of course perpetually...

Lee’s Mom

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A couple of years ago I had an experience that gave me a whole new perspective on how I look at older women. I went over to my friend's house to hang out, when I got there his mom answered the door in her swimsuit. She told me Lee wasn't there, but she figured he'd be home soon. She asked me if I wanted come in and wait for him. She told me she was going to work on her tan and invited me to come out and take a dip in the pool. I didn't have my swim trunks...

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Tags: masturbate, older-woman

Kathy

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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)

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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...

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

Johnny Gets Spanked (part 3)

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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...

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

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

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

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 train line...

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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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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...