Male / Older Female

Empire bays lake house

We have what were looking for Chapter one We used to be close As a young boy I had always enjoyed going to the family cottage with my parents. We always crammed as much activity as possible into the month of July: sailing, swimming, going to movies in the evening etc. I had always enjoyed a close relationship with my parents but this all seemed to end when I turned 15. Suddenly I hated being at the cottage, wanting to be anywhere else, feeling like I was a prisoner within the confines of my parents’ world. To make matters worse I was not allowed to bring my own friends, but my parents, of course, were constantly welcoming their boring friends to the cottage. July was hot, as always, and I tried to maintain my mental …

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Busty Babysitters with Young Boy

Ashley was a young girl growing up in the suburbs of her small hometown. She was a fun-loving kid that was constantly bubbling with happiness and energy. Ashley lived with her mom and dad in a moderately sized house. Her sister used to live with them, but she had since moved out with her boyfriend. Ashley looked stunningly beautiful for her age. She had sparkly blond hair that dropped down just below her shoulders. She had deep brown eyes and a very pleasant face to look at. She had large breasts for her age; a large C cup. (Almost a D.) She had a succulent, curvy body and a nice round, perky ass. It was 4:00pm on a Friday afternoon and Ashley had recently gotten out of school and she was texting her friend, Rachel. …

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TANYA’S RETURN VISIT

Sarah made small chat as she lay face down, resting on her elbows. with a huge smile as though this situation was nothing unusual as I oiled her back, then her magnificent ass cheeks. “I had heard rumours about your ass. All true, big, firm, no dimples and just magnificent. I had also heard rumours about the size of your man’s erection,” she told us with a tremor in her voice. “Rumoured to be thick and nine-inches when fully erect. Awesome, even flaccid you must be five or six-inches,” she smiled as she ogled my almost hairless cock. “Would you like to see his cock fully erect?,” Sarah teased knowing right at that moment Tanya would like nothing better. Also knowing she and I would both enjoy flaunting my erection for an attractive, beautifully dressed …

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MY LADY HAS PROMISED ME A NEW SEXUAL EXPERIENCE

Sarah was relaxed, wearing heels, a short denim skirt and a matching denim jacket, just one button fastened, obviously no bra, as she flaunted her wonderful thighs and modest cleavage. As the time of arrival of my new sexual experience neared (or will it be our sexual experience}, Sarah teased me by asking, “Your new sexual experience is due at two-thirty. If you had a choice for today, what would it have been? Let me guess a young boy and girl in their early twenties. You love flaunting your thick, nine-inch erection for a boy in his early twenties. So do I, before I have him.” Before she could continue our intercom announced the arrival of our guest or guests, I still had no idea what Sarah had organised for me. Sarah buzzed them in …

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Teachers Pet 2_(1)

When last we left our intrepid teenager he was taking a shower with his homeroom teacher, learning more about the birds and the bees than his A B Cs. After Scotts Saturday afternoon fuck-fest with Miss. Porter (Patty) he walked home with his mind full of what this new relationship would mean. Was she his girlfriend now? She had already told him that he couldn’t tell his friends or anyone else about what they had done or she would be fired, arrested and charged with sexual assault on a minor. In short, her life would be ruined. “That sucks” he thought. He wanted to tell the whole world how he had fucked and sucked a REAL WOMAN. How could he ever look at girls his own age the same again? He wanted the kind of …

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Robin and Mary Part 2

Robin and Mary Part 2 Don’s phone rang about 9:30am. After the exhausting night he had spent with Robin, he had managed a short nap after the great titty-fuck she gave him that Saturday morning, right after she sent her husband (Jake) off to work for the weekend. Jake would be doing system upgrades for two banks and wouldn’t be home until the following Tuesday. “Hello, mister big dick. Are you ready for my mom?” “Actually, sugar, you just about killed this old forty-three year-old man last night. I can’t remember knocking off that much fine pussy, even in my younger years.” “Donnnnn…,” came a little whine, “you promised…” “Yeah, well, I really didn’t expect to be filling you up all night long, though. But… if you still want me to give her a shot, …

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Seduction of a Babysitter Part IV

In the middle of the night, Nathan woke up, laying next to Melissa, holding on to her. He rolled over, trying to find out what time it was. He looked at her alarm clock and it read 3:00 a.m. He jumped out of bed realizing Janis would be home in few hours, and he didn’t want to get caught in bed with her daughter. He hurriedly went to the laundry room and put the couch cushion covers into the dryer, and took Melissa’s sheets into her room. As they were drying he went to the front room and started watching TV, trying to pick up the mess in the front room. After the dryer finished, he put the covers back on the cushions. He went to Janis’ room and found an extra blanket and laid …

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I Accidentally Called My Boss Mom Pt. 1

I Accidentally Called My Boss Mom Pt. 1 Being an office temp is better than a flipping burgers, I suppose. I’m 20 years old, and I skipped out on college so my options are limited. I started this new job four weeks ago. I had to get a suit from Goodwill, fill out a proper resume, and had to endure a tense interview with the director of the department I was to work at. She introduced herself as Amanda Jones, and I had never met a more beautifully intimidating woman in my entire life. She was slightly shorter than me, about 5’8”, but her presence was intense. She was significantly older than me, probably 38, and aging gracefully. She wore a modest black knee-length dress and wore her hair down to her shoulders, with deep …

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EXPLORING OUR SEXUALITY

“We both have strong sex drives, we are both exhibitionists and voyeurs, we both have a kinky side. I want us to be unapologetic about what we both want and set boundaries. I want us keep an open and honest communication channel with our sexual partner or partners. “I want to get to know every inch of your body and you mine. And yes, that means mutual masturbating. Even better with someone watching. Let’s have fun. Sex should feel great, so remember to prioritize pleasure.” I thought we were having fun, our sex feels great and we were prioritizing our pleasure,” I replied. “Yes, however, I want us to be unapologetic about what we both want and set boundaries. For instance I would love an attractive young boy, naked, early twenties, with a good body …

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My Polish Neighbour Chapter 3

My Polish Neighbour Chapter 3 (Maria’s been neglected by me awhile!) A holiday away with my parents intervened. We had hired a boat to go on the rivers and lakes about 100 miles from where we lived. It was bliss with my Mum and Dad both ecstatically happy. I could hear them every night getting off with each other in the room at the rear of the boat, whilst I had a bunk and room to myself at the bow of the boat. We all swam in the water which wasn’t too deep. Mum was at her most relaxed in her one and two piece swimsuits. I don’t know which I preferred. But occasionally when we were alone, she would flaunt her body a little at me, casually allowing the tops of her breasts to …

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Strict rules of engagement Part 2_(1)

Part 2 “I’ve never been a squirter!” Janice thought to herself as she squeezed her thighs together and felt her cum spread around her inner thighs from the pressure. She held that position for a while as she leaned against the center counter in the kitchen, amazed at having that much fluid leave her pussy during an orgasm. Brody came up stairs and sat in the living room. Dinner was almost ready so he found no point in going up to his room only to be called down in a few minutes. While sitting in the living room, instead of watching TV he was watching his mother move about the kitchen. He noticed she was still wearing her cum soaked yoga pants which made his cock twitch, he adjusted in an attempt to conceal it …

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Ramblings of an Old Man – Part 10 “Oh Maggie, Maggie-Mai…”

As an old man, in my seventies, who has been given the nod by my doctors that my days are numbered, I spend a lot of time looking back at my life. Recalling what I have done and achieved. Regretting the things I should have done and did not do. I do not suppose for a moment this is unusual, but when it happens to you, it takes it out of you, initially at least. I never planned on these thoughts going public. It was just a few scrappy notes for my own consumption. The ramblings of an old man, as it were. But one of the individuals concerned saw those notes. They thought that others may identify with some of the situations and suggested I tidy them up into a story and post them …

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11 – College Years 3 – Home for Thanksgiving

Note: As per my other stories, the character names are all changed on the off-chance that there is someone who recognizes any of the descriptions of living arrangements or furniture. If this is the first story of mine that you are reading, I have stories before this – while the other stories are not necessary to read, they do help to build up some backstory to where I was in my life at the time. Once again, while the verbal interaction may not be accurate, the physical interaction is to the best of my recollection. I’ve edited the titles of my other stories to include numbering in case anyone is confused. I apologize that the site doesn’t list them in publishing order, but I can’t really do anything about that – doing what I can. …

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4 – Senior Year

Note: As per my other stories, the character names are all changed on the off-chance that there is someone who recognizes any of the descriptions of living arrangements or furniture. If this is the first story of mine that you are reading, I have three stories before this – while the other three stories are not necessary to read, they do help to build up some backstory to where I was in my life at the time. Once again, while the verbal interaction may not be accurate, the physical interaction is to the best of my recollection. ——————— Eleventh grade was incredibly non-descript. I did a lot of the same things I imagine most teenage boys did in the early 2000s in a big city – smoking pot, drinking when I could get my hands …

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Grandma Jeanie and Her Younger Lover

This is another true story about my conquests with the older woman. I just really love sex with these old woman, there bodies just turn me on. This story start like most of mine. I started chatting with this lady on one of the well known hookup sites. I had been online for a few weeks without much success until I started chatting with Jeanie. I sent her an initial email and then started chatting through messenger with her. Jeanie is about 5’3 and about 150 pounds. She’s your typical grandma shape, nice, soft and plump. Now Jeanies age may shock some of you, she’s 70 years old! She’s still married but husband is in care and she’s not had her needs met in years. It wasn’t long after we started chatting that the conversation …

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Breeding My Widowed Aunt Rose

After a year in college I had become very disillusioned with my prospects. Not only was I failing my classes but I felt like a little cog in a big machine; a machine designed to extract money from people like me. However, my parents had high expectations and I didn’t want to disappoint them. After much consideration, I figured I would take a semester off to figure things out. As expected, my parents were not only disappointed but angry as well. “So, what the hell are you going to do?” my father asked. “ I don’t know yet,” I replied. My mother joined in on the scolding and pretty soon I felt like a failure. As I retreated to my room my father yelled “Maybe you should join the marines, that way you can get …

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ANOTHER PROMISE

“Yes, you know I could handle that, I always reply, knowing that would be exciting for her, very exciting – and me. We have followed through a number of times with two men, usually much younger. Always a buzz for me watching my naked lady pleasuring and being pleasured by two men. Most of the men or boys I source from my gym, it lessens any jealousy I might feel. On the occasions Sarah organizes two men there is always increased sexual tension while I wait for the boys or men to arrive, wondering if they will be a threat to me. “No need to feel threatened baby, we still haven’t had any boys or men more impressive than your, thick, nine-inch erection, some were close though. However, some of my girlfriends have the same …

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A BOY FOR MY MAN AND ME

Mike had masturbated many times while watching me with new sexual partners, female and male, his strong exhibitionist streak in full flight. I had had sex with him while one of my voyeuristic female friends watched and masturbated. The sudden realisation Mike and me had never had sex while another male watched while masturbating for us, came about when one of my girlfriends told us over coffee how she and her husband like to fuck with another man watching and masturbating. Asking if we would like to hear about the man who watched them fucking while he masturbated last Friday night? Of course we would! “He was a hunk of a man, just a boy really, only twenty-years old. My husband insisted on me undressing the boy while we were both wearing short white, Terry …

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Cougar Stepmother Slut Fun!

“You always seem so nervous, Steve!” Rikki’s mom was standing in his bedroom wrapped in a bath towel and looking into an open bedside drawer that had Rikki’s dildo just laying there. “I was just wondering what you’re doing in our bedroom, that’s all.” Steve was trying to be polite but couldn’t help seeing that his wife’s mother had a nice body. He was sure she was doing this intentionally. “I was just looking.” She said curiously. “So how do you like married life? What’s it been, three months now?” Trying not to stare he said, “Yeah just about. I love it. I really love your daughter a lot.” “That’s nice. You ever wonder what your wife is gonna look like in twenty years?” It was an odd question. “I… uhh” But before he can …

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A Milestone to Remember (revised)

That is what it is, a milestone of life that requires something put into the bucket list. My fortieth birthday, the entrenching realization of middle age setting in with a building sense of urgency to experience something or anything that can check mark a life with enough excitement to carry oneself for that long steep decline of age. Maybe a long ways to go, but I was bound and determined not to go gently into that good night. So I forced the issue, demanded to my family I needed to do something…anything. Thought about a cruise…everything was booked on the major lines for a year or so. Looked into an all-inclusive…the choices were slim, none for the bigger names, but found an opening in one obscure resort that actually got my blood moving. My husband …

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