ShandyLeer
Literotica Guru
- Joined
- Nov 21, 2020
- Posts
- 555
……..Amy had always been interested in her man’s past, often playfully jibing him about the popularity he enjoyed - at least according to some of his friends - with girls years before Nathan and her ever met. They’d only been together 5 years now after all.
Mostly she liked to believe it came across as just gentle teasing, but truth be told there was a little bit of her - perhaps thanks to a touch of insecurity more than anything - that liked to feel she knew more or less what and who he had, and hadn’t, done. The headlines at least.
And yet Nate sensed that she wasn’t so keen to share stories of her own.
He wasn’t stupid, she was truly beautiful now in her 40s and must have knocked guys dead at first glance back in her 20s, when life for her as a daughter of well off parents seemed to be endless clubbing and parties. Her looks and circle of friends alone meant an invite to nearly everything in town worth being invited to, and no doubt she’d have met many attractive and successful suitors, including those that may just have designs on her for the night. Nate got that, because had he met her back then he’d no doubt have chanced his luck too.
He reasoned that, since she’d never married nor had a single long term boyfriend for more than a few weeks right throughout her 20s and early 30s, choosing instead to live in her own city centre apartment, it seemed likely there’d have been a few boyfriends.
Nate found the idea of all those men back then wanting her, and frankly the idea of some of them having her, so hot to imagine. And yet he just sensed a reluctance on her side to go there when he might gently push down that road, and so backed away.
And then, quite out of the blue, Amy changed direction.
It was only the second night of their week long vacation. The beach had been paradise all day and now, as evening had fallen they’d eaten well and shared some wine. Tomorrow they’d stay out til late maybe, but tonight Amy wanted to head back to their villa and slowly fall asleep to the sound of the waves lapping the beach only metres away from their door.
She sat outside on the terrace and he joined her on the sofa, wrapping his arm around her.
“Nate, I know you well enough to know you’d love for me to tell you some stories from my past. I get it that it turns you on, and it’s hardly weird or unheard of that you might.
Its just that maybe once or twice I wasn’t proud of myself, let myself down and for some stupid reason I end up beating myself up about a whole decade and a half of my “single’ life, despite maybe only 2 or 3 actual bad choices. I made.
I need to stop that. I only care what you and I think, the rest is nonsense anyway.
So, if it might turn you on, then I‘ll tell you my first “sexual experience”.
I was 19 and my boss who owned the business, a restaurant, was a 50 year old guy who liked to think he was cool, nice car and well dressed and that girls loved him. Of course I didn’t, he was way out of my age range.
He invited me and a co worker for a celebration drink on his birthday, and since I had a girlfriend with me it seemed a good idea and he was, to be fair, a really pleasant and interesting guy.
On the way home in his car my friend hopped out at her place, and Mark - my boss - was supposed to drop me home next, only a mile further up the road. But he swung instead down a side route and up a winding lane and parked the car overlooking the cliffs near my apartment, telling me how amazing the moonlight was and how amazing I was too and how he just wanted to chat with me alone for a few minutes.
And then I saw - and don’t ask how I hadn’t noticed something already, even despite the darkness - then I saw that not only had he undone his belt and his zip, not only did he have his fist around his dick - but that he‘d already cum. I mean, imagine.
It was obvious he’d been stroking his cock as he drove, and I imagine had ideas that I might take over once we parked but he was flustered and apologetic that he‘d “lost control”, because I was just “so hot” which is how he put it.
I mean Jesus Nate, these days I think I’d run to the cops but I was 19 and had barely kissed a guy. I didn’t know if it was somehow my fault or something, which he seemed to be implying - and I had a job to think of.
I mean I hadn’t touched him, nor he me but there it was - right in front of me, still in his hand and ever so slowly losing its hardness - and he’d cum so much, he’d cum such a lot sweetie.
It was the first cock I’d seen and, well, I was a little “impressed” I guess is the word , as well as surprised and a bit shocked. He seemed very vulnerable now, but I’m not sure I’d have felt so calm about it if he was still, well, still “ready”
But what I want to know is whether its sexy for you to finally hear a story from my past Nate…………? “
Mostly she liked to believe it came across as just gentle teasing, but truth be told there was a little bit of her - perhaps thanks to a touch of insecurity more than anything - that liked to feel she knew more or less what and who he had, and hadn’t, done. The headlines at least.
And yet Nate sensed that she wasn’t so keen to share stories of her own.
He wasn’t stupid, she was truly beautiful now in her 40s and must have knocked guys dead at first glance back in her 20s, when life for her as a daughter of well off parents seemed to be endless clubbing and parties. Her looks and circle of friends alone meant an invite to nearly everything in town worth being invited to, and no doubt she’d have met many attractive and successful suitors, including those that may just have designs on her for the night. Nate got that, because had he met her back then he’d no doubt have chanced his luck too.
He reasoned that, since she’d never married nor had a single long term boyfriend for more than a few weeks right throughout her 20s and early 30s, choosing instead to live in her own city centre apartment, it seemed likely there’d have been a few boyfriends.
Nate found the idea of all those men back then wanting her, and frankly the idea of some of them having her, so hot to imagine. And yet he just sensed a reluctance on her side to go there when he might gently push down that road, and so backed away.
And then, quite out of the blue, Amy changed direction.
It was only the second night of their week long vacation. The beach had been paradise all day and now, as evening had fallen they’d eaten well and shared some wine. Tomorrow they’d stay out til late maybe, but tonight Amy wanted to head back to their villa and slowly fall asleep to the sound of the waves lapping the beach only metres away from their door.
She sat outside on the terrace and he joined her on the sofa, wrapping his arm around her.
“Nate, I know you well enough to know you’d love for me to tell you some stories from my past. I get it that it turns you on, and it’s hardly weird or unheard of that you might.
Its just that maybe once or twice I wasn’t proud of myself, let myself down and for some stupid reason I end up beating myself up about a whole decade and a half of my “single’ life, despite maybe only 2 or 3 actual bad choices. I made.
I need to stop that. I only care what you and I think, the rest is nonsense anyway.
So, if it might turn you on, then I‘ll tell you my first “sexual experience”.
I was 19 and my boss who owned the business, a restaurant, was a 50 year old guy who liked to think he was cool, nice car and well dressed and that girls loved him. Of course I didn’t, he was way out of my age range.
He invited me and a co worker for a celebration drink on his birthday, and since I had a girlfriend with me it seemed a good idea and he was, to be fair, a really pleasant and interesting guy.
On the way home in his car my friend hopped out at her place, and Mark - my boss - was supposed to drop me home next, only a mile further up the road. But he swung instead down a side route and up a winding lane and parked the car overlooking the cliffs near my apartment, telling me how amazing the moonlight was and how amazing I was too and how he just wanted to chat with me alone for a few minutes.
And then I saw - and don’t ask how I hadn’t noticed something already, even despite the darkness - then I saw that not only had he undone his belt and his zip, not only did he have his fist around his dick - but that he‘d already cum. I mean, imagine.
It was obvious he’d been stroking his cock as he drove, and I imagine had ideas that I might take over once we parked but he was flustered and apologetic that he‘d “lost control”, because I was just “so hot” which is how he put it.
I mean Jesus Nate, these days I think I’d run to the cops but I was 19 and had barely kissed a guy. I didn’t know if it was somehow my fault or something, which he seemed to be implying - and I had a job to think of.
I mean I hadn’t touched him, nor he me but there it was - right in front of me, still in his hand and ever so slowly losing its hardness - and he’d cum so much, he’d cum such a lot sweetie.
It was the first cock I’d seen and, well, I was a little “impressed” I guess is the word , as well as surprised and a bit shocked. He seemed very vulnerable now, but I’m not sure I’d have felt so calm about it if he was still, well, still “ready”
But what I want to know is whether its sexy for you to finally hear a story from my past Nate…………? “
