older woman teen boy sex stories

Figuring It Out with Auntie Rosa

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Rosa smiled as she wiped some suspicious white stains off her favorite leather couch, using a chance to leave her yoga class early just to finish a few little tasks, like removing cum from her couch before it was stained for instance. Her nephew had a perfectly natural libido for any young adult… alongside the perfectly natural lack of care on where he worked on himself, were she of a more traditional demeanor she'd have gone straight to him, perhaps even made him clean it up himself, but she liked to think that she was better than that. Sure enough,...

Mom’s Big Boobs

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Mom’s Big Boobs is a follow-up to Sister’s Big Boobs, a story about a little sister who’s insecure about her big tits, and a loving, well-endowed mother who encourages her son to have sex with her to make her feel better about herself. You can read the first part here: Sister’s Big Boobs ***** The next morning, I woke up to the footsteps of Mom moving around the kitchen downstairs. I still felt the ache in my thighs from last night with Sofi, and a certain lightness, like I’d unburdened a part of myself. I took my time getting dressed,...

Jamie & Mrs. Gray

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I'd been renting a room from Mrs. Gray for almost 4 months. She was an older lady, a divorcee who looked similar to my mother in many ways. They were both tall, almost a full head taller than I stood. They were both sturdily built with broad shoulders, big boobs, wide hips, and thick thighs. And like my mother, they were both kind, but strict at the same time and could become firm if the need arose. Affectionate is not a word I'd choose to describe either of them. Even more, Mrs. Gray never liked to repeat herself or be...

Renting a Room from Mrs. Taylor

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My mother wasn't thrilled with my choice of moving to a nearby city. She worried about me constantly. But I finally convinced her I was old enough to take care of myself. I packed up my meager belongings and took a bus into the city. Luckily, it didn't take long to find my new home. I began renting a room in the home of my landlady, Helen Taylor, a woman a few years older than my mother. She was a full-figured lady with wide hips, huge boobs, thick thighs, and broad shoulders. She stood almost a full head taller than...

Seeing Mom

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I used to spend a lot of time in the bathroom of my parents' bedroom, peering through a crack in the door as my mother undressed. She'd call to me not to come out until she said so, unaware that I could see her quite clearly. I'd watch as she unbuttoned her blouse, revealing her large breasts, always in a basic white bra. The mere fact that I was spying on her was enough to arouse me, but the sight of her bra made me even harder. I'd continue watching as my mother took off her slacks, revealing a...

Kind Older Woman

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John had been at the library studying and when he left the building he wasn’t watching where he was going and hit his head on a low hanging branch. The next thing he knew he was walking on an inner-city street. He was still dazed and had no idea where he was. It was raining so he found an entrance to an apartment above a shop that was sheltered. Mary is a 40-year-old single woman who lives in the apartment. She was coming home from work when she found the young teen boy huddled in the doorway. She...

My Widowed Aunt

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Aunt Rita was my mum’s oldest sister and although she lived at the other end of the country she was always very close…. In fact I always thought of her as my second mum… She was married to Harry who was a lovely man and who I was also close to…. A bit like my best friend in fact. When they were sixty uncle Harry died suddenly… I went to the funeral with my mum and we stayed for about a week…. Rita was in bits…. Before we left to come home my mum told Rita that if she wished...

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Tags: aunt-nephew, incest, older-woman-teen-boy

Robert’s Unusual Trip to the Doctor

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16 year old Robert walked into the doctor’s office with his mother, to get semi-annual sports check up. His mother walked up to the nurse behind the counter. “My son Robert Conlin has a sports check up with Dr. Chase.” Stated his mother. “Conlin spelt c-o-n-l-i-n? At 2:30?” came the reply of the nurse. Robert’s mother nodded. “Dr. Chase is out on family business today, Dr. Kelso will be taking his patients for the day” Robert’s mother nodded, without much concern, she wasn’t all that worried about the appointment, it being only a sports check up. They walked over to...

Bath – a Mother and Son Story

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Carol hadn't had sex since her husband Ray had left more than four years ago. Strange as it sounds, the thing that finally brought her celibacy to an end was her son breaking his leg. *** Mike was 14 and a natural athlete. Whatever sport was in season, he played. He was good at all of them and great at some. It was at a baseball game where an inexperienced player slid into second base, spiking Mike's left leg and breaking it. There was knee damage as well, so Mike was now laid up with a cast almost hip to...

Roger’s Auntie Becomes His Mummy

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I have always been a fairly mild and meek person and would never get involved in any sort of confrontation and for that reason people seem to treat me rather badly. As an 18 year old in his last year at school I had begun to rebel a little and although my parents told me off a lot I tended to ignore them and do what I wanted to anyway. One day just as term was about to finish my mum said that I was going to spend the summer holiday with my auntie Dee. She said that as I...

My Aunt

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My story begins during that one fateful trip my aunt made to visit my mom and I. I was 19 at the time and my mom and I lived alone in our condo overlooking the water. Our house was nice, a big pool and a hot tub downstairs (my mom had a great job and that left us very well off). I also had a problem. After many years of masturbation I could not make myself reach an orgasm. I thought I came close a couple of times, but the fact that it never happened to me was cause for...

My First Handjob by My Aunt

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Hello everybody, the following story happened when I was 14, I am now 29. Let me introduce myself as "Jack" for privacy issues. Since a very early age I"ve been very shy, specially around women. I did not penetrate a girl until I was 18, even though I don"t consider myself to be bad looking. Sometimes girls would hit on me when I was in high school but to be honest I was too shy to make any moves on them. I have been playing soccer since I was 8, I love the sport ant that helps me keep in...

Stripping for My Nephew

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I slid my hands over my skinny toned stomach as I smoothly put my slinky black bra over my round D cup breasts. My nipples were still erect from my performance. I slid on a white wool sweater and tied my silky blond hair into a loose bun. I pulled out the last of the bills that were stuck in the waistline of my thong and organized them in a neat pile before putting them into my bag. “How’s the crowd tonight Carly?” “Not bad Stacy, a few horny businessmen but I’m afraid I milked them for everything they have...

A Baby Boomer’s Tale

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It was a hot and muggy Autumn Friday evening in the late 1950’s and I was bored out of my mind. We lived out of town on a small farm holding which wasn’t quite an economical unit and, as a result, Dad worked as a truck driver on long-distance haulage and only farmed part time with lots of help from the family. Our family consisted of me, a 14 year old male, my 15 year old sister, my mother who was in her late 30’s and Dad who must have been about 40. We were a reasonably close family but,...

In the Family

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My aunt Alice, visited my house this afternoon for a social call to see me and my bro, mom, and dad. She's tall and blonde, has glasses and is very slim with nice hips and soft hair, but hasn't much confidence (particularly with men) and dresses in cardigans, big skirts, tights, for a forty year old though, she is quite attractive I guess. On a more personal level, she has small 30a breasts, and has never really had a relationship of any kind. I'm about 5'8" and have shaven blonde hair. I'm slim and a little bony, yet to...

I Tricked My Busty Step-mom (part 2)

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So, I got my busty step-mom Becky to parade around the house half-naked with her tits jiggling, squeezed up with her bra stretched down below them. They were bouncing around like some firm platters of jelly waiting to be gobbled up, exposed and tempting as hell and she was doing it just as I had asked her to do. The way the bra, pushed up from below them, made them look as if someone had both hands around the base of each of them, squeezing them so they bulged out so smooth, round and firm, with their thick nippled-tips jutting...

I Tricked My Busty Step-mom (part 1)

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I've lusted after Becky ever since the first day dad brought her home. Now, after a year of fantasizing about getting her large firm succulent hooters into my hands, I finally 'concocted' a scheme to make her mine. My real mom left us for the west coast about a year ago and I rarely see her anymore. My dad immediately hooked up with Becky and I've certainly been glad just to see her around the house. Becky was quite a bit younger than my dad, only in her early 30's and, though she always dressed rather shyly, you could tell...

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,...

Sharing A Bed With Aunt Linda

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My Aunt Linda and her son moved two blocks from my house the summer I turned sixteen. The week before moving in, she called my parents up and asked for help. My mom handled all things connected with her sister with suspicion and scrutiny and initially heed and hawed over being available. My dad, on the other hand, quickly agreed to help out but then it was obvious that he had a hard on for my aunt. She was petite and tan and with an ass like ripe fruit. My mom gave my dad a look but he just...