First Time

[tigerfeet]

I was almost 17 and I had just broken up with my long term girlfriend, Jessica. She was all I'd ever known, and I was lonely, angry, and kicking around in the dust for something to do.

My parents had booked a holiday - with Jessica, and me - to go to Portugal and stay in my uncle's house, which was a quiet and remote villa outside of a village near the sea, somewhere in a fairly average part of the Algarve in Portgugal. To avoid wasting the ticket, after Jessica and I broke up, I asked my friend Jamie to join us. Jamie had been my best friend since I was 13. He was a couple of years older than me. He was funny and erudite, tall and slim and blonde, with skin that would quickly tan a kind of golden brown. Jamie had never been good at sports, but he had aced the arts and had taken all the lead roles in the school plays so was a bit of an enigma. I was proud, and jus a little in awe, to call him my friend.

It was a kind of ordinary holiday. Trips to the beach, trips to the market. At night my parents used to go to a restaurant while Jamie and I drank gin and smoked cigarettes at the apartment. We'd swim too, in the dark. And when Jamie dared me to swim naked with him I laughed, a lot, then slowly took off my shorts. I can still feel the pulse in my cock as I slipped my swimwear down over my ankles for the first time.

We swam. i think it was the first time for both of us - being naked and close. I remember us kind of going through routines: stretching, swimming past each other, or underwater. Coming close but not too close, dipping under the water so our skin shimmered in the ripples and moonlight. All that. It's all a mess in my mind, but it ended when my parents came home and we swam to the side with sheepish grins and our swimming togs in our fists. Saying sorry. Laughing. Watching them turn the light off and go to bed.

And that's how it started.

if you'd like to hear more, let me know...

 

[Bxblknight]

4sho'! Great start!!

 

[tigerfeet]

I was almost 17 and I had just broken up with my long term girlfriend, Jessica. She was all I'd ever known, and I was lonely, angry, and kicking around in the dust for something to do.

My parents had booked a holiday - with Jessica, and me - to go to Portugal and stay in my uncle's house, which was a quiet and remote villa outside of a village near the sea, somewhere in a fairly average part of the Algarve in Portgugal. To avoid wasting the ticket, after Jessica and I broke up, I asked my friend Jamie to join us. Jamie had been my best friend since I was 13. He was a couple of years older than me. He was funny and erudite, tall and slim and blonde, with skin that would quickly tan a kind of golden brown. Jamie had never been good at sports, but he had aced the arts and had taken all the lead roles in the school plays so was a bit of an enigma. I was proud, and jus a little in awe, to call him my friend.

It was a kind of ordinary holiday. Trips to the beach, trips to the market. At night my parents used to go to a restaurant while Jamie and I drank gin and smoked cigarettes at the apartment. We'd swim too, in the dark. And when Jamie dared me to swim naked with him I laughed, a lot, then slowly took off my shorts. I can still feel the pulse in my cock as I slipped my swimwear down over my ankles for the first time.

We swam. i think it was the first time for both of us - being naked and close. I remember us kind of going through routines: stretching, swimming past each other, or underwater. Coming close but not too close, dipping under the water so our skin shimmered in the ripples and moonlight. All that. It's all a mess in my mind, but it ended when my parents came home and we swam to the side with sheepish grins and our swimming togs in our fists. Saying sorry. Laughing. Watching them turn the light off and go to bed.

And that's how it started.

if you'd like to hear more, let me know...

So, we finish swimming. Sit on the side of the pool with towels around our waists and the moonlight above us. Quietness. Crickets. Jamie turns to me:

'Let's go to bed.'

This 19 year old boy, laughing, and dragging his body out of the pool in front of me. Heading, dripping, to the door. I hear the shower start to run.

 

[tigerfeet]

And I push back against the tiles in the pool. Silence, crickets, the sound of Jamie in the shower, the cold water against my body, my hand finding my cock for the first time that night. Wondering what happens next....

 

[Fortheloveofmen18]

Mmm. This is the kind of story I love!

 

[Florenzp19]

This is awesome!

 

[miamirt]

Sounds great!

 

[justbigenuff]

This is a good start, but will the mods object to under-18 sex? Is there a way to describe events in a more neutral way, like "I was young" or "I was a teenager"? In truth, many of us begin meaningful sexual adventures before 18....

 

[tigerfeet]

I was almost 17 and I had just broken up with my long term girlfriend, Jessica. She was all I'd ever known, and I was lonely, angry, and kicking around in the dust for something to do.

My parents had booked a holiday - with Jessica, and me - to go to Portugal and stay in my uncle's house, which was a quiet and remote villa outside of a village near the sea, somewhere in a fairly average part of the Algarve in Portgugal. To avoid wasting the ticket, after Jessica and I broke up, I asked my friend Jamie to join us. Jamie had been my best friend since I was 13. He was a couple of years older than me. He was funny and erudite, tall and slim and blonde, with skin that would quickly tan a kind of golden brown. Jamie had never been good at sports, but he had aced the arts and had taken all the lead roles in the school plays so was a bit of an enigma. I was proud, and jus a little in awe, to call him my friend.

It was a kind of ordinary holiday. Trips to the beach, trips to the market. At night my parents used to go to a restaurant while Jamie and I drank gin and smoked cigarettes at the apartment. We'd swim too, in the dark. And when Jamie dared me to swim naked with him I laughed, a lot, then slowly took off my shorts. I can still feel the pulse in my cock as I slipped my swimwear down over my ankles for the first time.

We swam. i think it was the first time for both of us - being naked and close. I remember us kind of going through routines: stretching, swimming past each other, or underwater. Coming close but not too close, dipping under the water so our skin shimmered in the ripples and moonlight. All that. It's all a mess in my mind, but it ended when my parents came home and we swam to the side with sheepish grins and our swimming togs in our fists. Saying sorry. Laughing. Watching them turn the light off and go to bed.

And that's how it started.

if you'd like to hear more, let me know...

Thanks for all your comments so far. Here's what happened next.

The house went dark. We'd stopped laughing and playing around. There was an awkwardness, to be honest, and if I remember correctly we both ended up doing laps of the pool as if it was all normal and we were only there to swim after all.

Jamie got out first, when I was at the other end of the pool. He had his back to me and I could see him pulling up his shorts over his ass as I swam another length of the pool. When I got out, he was gone. Back inside the villa. My cheeks burned, and my heart skipped. I know these posts are often about the pure hard drive of our first experiences, but the nervousness and fragility is what I remember.

I smoked then, something about being more grown up than my years, and sparked a Marboro light up with my towel wrapped around me, sipping a slightly deflated diet coke. Darkness around me, but still warm too. Hot even, despite it being late. Nerves and exercise and heat making the beads of sweat pop through on my chest and neck. Droplets running lazily down my chest and stomach to the towel at my waist.

I hadn't noticed it before, but the deck by the pool looked over the room Jamie and I were staying in. Two single beds, white walls, tiled floors and an ensuite bathroom. And a large window over the pool. So as I smoked and sweated a little, I realised I could see Jamie move around the room, headphones in, olive skin (I think his mum was Italian), leaning against the wall by the window. The outline of his neck, chest, stomach, and a definite bulge in his shorts that made me gasp a little, silhouetted in the window frame.

My coke was finished, and I let my cigarette burn out.

I just walked to the bedroom. To where Jamie was.

Shut the door behind me.

Jamie was leaning half out of the window, letting the breeze and the curtains cool his skin. Dark hair in lazy curls. Tight, white underwear, not the shorts I had seen him in earlier, or the PJ bottoms he'd been wearing over the previous nights. He didn't look round.

Something in the air. Electric. Panic. Heartache. Hope. Everything.

I gambled.

Walked to the window in my towel.

Leaned forward, with my forearms on the windowsill, touching Jamie's. Tried to breathe.

Silence. Heart pounding.

His hip seemed closer - had he done that, or was I imagining it?

No, his hip was closer, and his thigh touched mine. And then his shoulder.

I could feel my heart start to race, a dull throb in my cock and butterflies in my balls as Jamie turned to me, lips a little open like he was starting to smile. His eyes working their way from mine, to my lips, to my neck, my chest, across my stomach, down to the wet towel that still hug around my waist. My cock pushing against the fabric.

I remember being suddenly really embarrassed under his gaze. Moving my hands until they covered the throbbing erection that was pulsing away under the towel.

So Jamie reached out and cupped my hands, moved his fingers over them - tracing the heavy bulge of my cock through my fingers as he did so, staring at me all the time. Until I dropped my hands and gave in. Let him. Let him touch me, pulling the towel away and wrapping his fingers around my rock hard cock for the first time, his other hands finding my balls and cupping them. Pulling me towards him. His lips on mine for the first time. With the window wide open and the breeze starting to move the curtains.

All my nerves went. My heart stopped skipping, and starting pounding. I was in Jamie's hands.

 

[tigerfeet]

This is a good start, but will the mods object to under-18 sex? Is there a way to describe events in a more neutral way, like "I was young" or "I was a teenager"? In truth, many of us begin meaningful sexual adventures before 18....

Hey there. The age of consent in the UK and Europe (where this is written and where it took place) is 16 so this falls within that framework. However this is a great point and I wouldn't want anyone outside of those jurisdictions to find this odd, so I've tried not to mention age in my second post. I hope that helps.

 

[tigerfeet]

Hey - I've written a second part to this story, above. there are a couple of other replies to the first part of the story under my name but, if I'm honest, I don't recognise them ad don't think I wrote them, so please ignore.

 

[JackWesterJr]

First time with a man...
Both of us were older. He wanted some simple mutual masturbation. We stripped and started to explore each other in bed, very quickly reaching 69 and mutual tasting of all parts. Lots of fine play time for both of us.