My 1st time fucked: The high school football player

Now that the ice had been broken, so to speak, following our first time jerking off together on the beach, Ben and I started jerking off together on a daily basis. And it didn’t have to be at night anymore. Broad daylight and the outdoors made our jerk-off sessions all the more exciting. Daily was not nearly enough for my raging hormones and I always pushed for a second jerk off session later in the day, with some success.

One thing Ben didn’t like about his family vacation in Greece was that he didn’t have access to a proper gym in the village, making it difficult for him to stay fit ahead of the upcoming football season. So, he would do tons of push-ups and sit-ups instead. But that wasn’t quite the same as pumping iron. On my side, I cherished our sit-ups sessions when Ben asked me to hold his feet with my hands. I’d watch his sweaty torso be lifted up and down and his exposed armpits when he crossed his fingers behind his neck. On the way up, his lips would be just inches from mine, which would stiffen my dick in my shorts.

Since he couldn’t really build muscle mass during his vacation, just barely maintain what he already had, Ben would focus on cardio instead. The Greek countryside around the village was beautiful and there were plenty of trails to explore. As he always said, running on rocky trails was better for his core than running on pavement anyway. And the terrain was hilly with lots of steep inclines that got our heartrates up. I never really enjoyed running, especially if there is no ball to chase. But running behind Ben was completely different. Staring at his muscular ass bouncing on the uneven ground was all the motivation I needed to go run. He had brought cyclist shorts, which were in style in the 90’s. They left nothing to the imagination, either in front or behind. The middle seam in the back even dug into his ass crack, which was 100% homoerotic. Seeing his sweaty body shining in the sunlight at the end of our runs was up there on my hardon-o-meter, close second to drooling at his wet Speedos at the beach.

At the beginning of my stay in Greece, we would get back home after our runs and hose ourselves down in the backyard. Ben preferred the lukewarm water from the hose to cool off his body, more so than the shower inside the house. And so did I. Is there anything more electrifying than watching a shirtless hunk hose himself down in the sun in his tight cyclist shorts? But following our initial jerk-off session on the beach, we would usually find a quiet spot toward the end of our run, whip our cocks out, and jerk off together before going back home. The region of Greece where their summer home was located wasn’t touristy at all. There were no resorts or campgrounds and I never heard anybody speak any language other than Greek. If we went for an hour-long run, we would rarely cross paths with more than a handful of locals. Finding a remote spot where we could jerk off in peace wasn’t that difficult. And the thrill of knowing there was still a slight chance we could get caught, no matter how remote that chance was, made it all the more exciting.

We weren’t shy about jerking off next to each other and watching each other jerk off. We actually enjoyed comparing each other: our bodies, our packages, our technique, and our cumming patterns. I’m sure Ben was turned on by the fact his cock was bigger than mine. And I was turned on by watching his big fat cock. Everybody was a winner!

One day, when we had just started beating off, I asked Ben: ‘I’ve noticed your technique of twisting your fist around your dickhead. Why do you do that?’

‘I don’t know’ he answered, ‘it just feels great when I do it’.

‘Have you ever wondered what it would feel like to be jerked by someone else? I asked, ‘I could try to twist my fist the same way you do’.

‘No’ he replied: ‘Are you gay or what?’

‘No, I’m not gay’ I briskly responded, faking being offended by his insinuation, ‘I’ve just always wondered what it would feel like to have a girl jerk me off’.

‘Let me try on you’ I insisted, ‘If you don’t like it, we can stop right away’.

I brought my hand to his cock, pushed his hand away, and started jerking his cock up and down.

‘I think it’d be better if you closed your eyes’ I said.

Ben closed his eyes, and I continued jerking him off, trying to imitate the twisting motion of his own hand.

‘How does it feel?’ I asked.

‘It feels great’ Ben responded, his eyes still closed.

‘It feels like my left hand is doing it’ he joked.

It was my first time holding that big piece of meat that I had been fantasizing about for so long. It was clearly meatier than mine. It just felt heavier, more powerful, more manly. His dickhead wasn’t as prominent as mine, which made his dick pointier. But the middle portion of his shaft was extra wide, even wider than the base. That’s the part where my thumb and index finger could barely touch each other. There was also a big purple vein running along the top part of his shaft. Ben needed some serious blood flow to power his big tool. His cock was probably an inch or so longer than mine. That meant the up and down motion was a lot longer than on my own cock. When I was jerking my own cock, my hand could almost grab my whole length. With Ben’s cock, when my hand was bottoming out in his pubes, his dickhead plus another inch or two were still sticking out.

I brought my left hand to his balls and started fondling them, the same way I had seen him do. Ben moaned a little. His balls were not much bigger than mine, but they were hanging much lower. My ball sack was always so close to my body that it made it harder to play with my balls the way I could with Ben’s. Looking at Ben’s face, he seemed to savor my manhandling his package. But the excitement was all mine too. I had only played with one other dick before. But it was the German exchange student, who was only 14 at the time and only had a 5-incher. Ben’s big sausage was my first real cock ever. Holding it in my hand felt awesome. My dick was throbbing on its own, with ample amount of precum leaking out of it, forming a little puddle in the red dirt underneath me.

Ben started moaning more intensely. He started making faces. And a volley of white cream shot out of his cock and landed in his treasure trail. The following ones didn’t even shoot, they just dripped on my fingers. Ben didn’t precum the way I did. As a result, his man juice was a lot creamier and a lot whiter than mine. My boy juice always looked more translucent, half semen and half precum. Ben’s thick cream kept flowing out of his piss slit and running along my fingers. It was now dripping on his pubes. The flow eventually stopped, and Ben opened his eyes.

‘How did I do?’ I asked.

‘You did great, man’ Ben replied, ‘It felt different, but awesome’.

‘Good’ I said.

‘And you don’t have to jerk me off if you don’t want to’ I added, ‘I can take care of it myself’.

‘No’ said Ben, ‘I want to return the favor’.

I lied on my back in the grass, and Ben lied next to me, grabbing my dick with his hand. His hand touching my hardon sent shivers all over my body and I almost came right on the spot.

‘I’m so horny right now that I’m probably gonna cum in just a few strokes’ I told Ben. ‘Don’t try to twist your fist on my dickhead. Just go up and down’.

And up and down, he went. I closed my eyes and relished his fingers on my cock. It felt incredible. The scent of cum and sweat intertwined filled up the air. It was electrifying. So much raw masculinity radiated from our bodies, even though we were just teenagers. The sensation of Ben’s fingers was so much more intense than when I was doing it. And as I had predicted, my dick erupted within a few seconds. Without even having a chance to warn Ben, big volleys started flying all over my body, much further than Ben’s volleys. One landed on my chin, another on my neck. Some landed in the grass on my side. But most landed on my chest.

‘Dude, you always shoot so far!’ Ben exclaimed, ‘How do you do that?’

‘I don’t know’ I responded, ‘The horniest I get, the further I shoot. It’s always been that way’.

We both rested on the grass, soaking up the moment. Then, we cleaned up as much of our teenage juice as we could, put our shorts back on and finished our run home. This time we didn’t hose ourselves out in the backyard. The hose was great to rinse sweat out. But we had a lot more than just sweat to rinse out. We showered in the bathroom where we had more privacy to clean up our boy mess.

After getting changed, it was already time to prepare lunch. Ben’s jokes while peeling carrots became a lot more direct. There was no hiding that my carrot was smaller than his and, from that moment on, he never missed an opportunity to rub it in. Every time there was a skinny carrot, Ben would waive it under my nose and joke that my dick’s size couldn’t even rival the carrot. But I didn’t care. If it was the price to pay to continue handling his big zucchini, I was game. And I would just joke back: ‘I’ll stick my carrot up your ass, and we’ll see if you feel something’. To which Ben would come up with comebacks along the lines of: ‘Based on the size of the dump I took this morning, your mini-carrot wouldn’t even touch the sides’. Just two teenage boys pumping their chests at each other, all in good fun.

But I also had comebacks for Ben. Once he finished shooting, Ben’s cock would go soft right away, while mine could stay hard. I had also showcased my ability to achieve double orgasms. That gave me something to brag about. Whenever a carrot was curved, I would point it downward and joke about Ben’s inability to keep it up. Boys will be boys!

One day, we had stopped by our usual quiet spot and started jerking off. I pointed to his cock and asked: ‘May I?’

Ben responded: ‘Be my guest!’.

An inside joke, it would take too long to explain.

So, I grabbed his hardon and started jerking him off. Ben had his forearms flat on the ground, his upper arms straight up, his elbows forming a 90° angle. His torso formed the third side of the triangle, so that he could watch his big cock being jerked by yours truly. I moved closer to him and started playing with his balls with my left hand. I was on my knees, bending down in front of Ben, allowing me a better grip on his cock. Every so often, I would look up at Ben’s face, just making sure he was enjoying what I was doing. And the look of pure relaxation on his face confirmed he was. But in-between, I kept my head down, focusing on my manual work. My mouth was less than a foot away from the tip of his dick. His low hanging balls were jumping up and down with my fingers tapping them from underneath. Ben was moaning a little. And all this was happening right in front of my eyes… and my mouth.

The scene became too tempting. I just lowered my head, opened my mouth, and before Ben even realized it, my mouth engulfed his dickhead, while my right hand was still jerking the base of his pole.

‘Dude! What the fuck! What are you doing?’ Ben asked.

But I just kept going. Moving my mouth up and down his shaft.

‘Jeremy! What is wrong with you?’ he continued.

I looked him up and replied: ‘Close your eyes and think that Angie Parker is doing it’.

Angie Parker was the most popular girl in school, she was in my senior class and the quarterback’s girlfriend.

And I went right back at servicing his cock.

‘No, Jeremy. Stop! This is wrong’ he insisted.

But I ignored his complaint and kept engulfing his girthy shaft with my tight lips. I wasn’t trying to swallow the whole thing. My hand was still jerking the middle part of his shaft, from his pubes to just below his dickhead. But my tongue was swirling around his dickhead, trying to recreate the twisting motion that Ben enjoyed so much.

‘Oh, Jeremy. Stop!’ Ben pleaded.

‘Shut up! And enjoy!’ I ordered.

Ben’s tone of voice had already started to change. The confusion in his voice betrayed him. His mind was still asking me to stop, knowing that being blown by another dude was wrong. But his cock begged to differ, sending signals that being sucked by a mouth was way more pleasurable than being jerked by a hand. Ben’s cock was sending electric waves all over his body and he started shivering a little. But the electricity was moving both ways and also traveled through my mouth, fueling my entire body. So, I ignored Ben’s plea altogether and kept sucking.

His cock, balls, and pubes were all sweaty from our running. With my nose a couple of inches away, I could smell the sweat evaporating from his hairy bush and from his entire body. It was intoxicating and brought me into another dimension. I kept sucking his cock like I was in a trance.

‘Oh, Jeremy!’ he continued, ‘This is wrong. But it feels so great’.

His moaning got louder, and he was starting to lose his composure. I stopped playing with his balls and brought my left hand to his mouth, trying to muffle his moaning. Not that it really mattered since we were in a secluded place and could be as loud as we wanted. But I just thought it was hot. His moaning subsided a little and I went back to playing with his balls.

‘Dude, I’m getting close’ Ben warned me.

As if I hadn’t noticed. I thought to myself it was a nice gesture for Ben to give me a last opportunity to escape the flooding in my mouth. But I wasn’t going to let my best friend down. I wanted him to explode like he had never exploded before. And I wanted that explosion to take place in my mouth and nowhere else.

‘I’m gonna cum! I’m gonna cum!’ Ben warned one last time, signaling he couldn’t hold it any longer.

I felt his balls rise up on their own. I felt his cock swell in my mouth. And his dick erupted, coating my tongue with big blobs of that white creamy juice I had been craving for so many times. Ben was shaking uncontrollably, and his moaning had turned into plain grunting. We normally tried to keep the volume down when playing with each other outdoors. But the pleasure was more than Ben could handle. His dick kept pumping more juice in my mouth, and I had to puff out my cheeks to not waste any.

Ben collapsed on the ground, his back now lying on the grass. And I let go of his deflating cock, my mouth still full with his boy juice. Now that I was no longer focused on pleasuring Ben, the taste of his Greek nectar on my tongue really hit me. I wish I could say I enjoyed it… but I didn’t. It was salty and kind of tart. I ended up spitting it back on the grass on his right side. The mix of his juice and my spit probably amounted to half an ounce. I’ve never been good with measurements anyway. It just looked like a lot.

Ben was still lying on the ground, inert, recovering from the orgasmic explosion he had just experienced. He looked so vulnerable. I could have done anything I wanted to him. But all I did was admire his magnificent body, his now soft but still swollen cock resting below his pubes, his sweat-covered chest, and the little patch of hair in between his pecs. He ended up rubbing his eyes with his fingers, giving me a full view of his hairy armpits. I had a grinny smile on my face, admiring Ben, motionless on the grass, trying to regain his senses. I felt the pride of a painter admiring his own masterpiece.

Meanwhile, my own dick was throbbing and leaking precum profusely. I lied right next to Ben, not on the side where I had just disposed of his cream, but on the other side. And I started attending to my needy cock. I closed my eyes, picturing Ben’s spasming body as he was about to shoot. And my dick exploded, sending ropes of boy juice everywhere. My cannon always shoots pretty far, but the more precum blocks my canal, the further I can shoot. My first jet flew over my head and ended up in the bush behind us. Had that bush not been in the way, my missile could have cruised all the way back to the US. That’s how horny I was. The following ropes landed on my face, on my neck, and on my chest.

Ben and I were now both lying motionless next to each other, each recovering from our orgasmic explosions. We looked at each other. Ben saw my cum-covered face and started laughing. I started laughing too.

‘Dude, it was incredible!’ Ben told me, ‘So much better than jerking off!’

‘You don’t even know how lucky you are’ I replied. ‘Angie Parker could never have sucked you like that’.

‘You, arrogant bastard!’ Ben joked, ‘But you’re probably right. You’re a master cocksucker, you know?’ he joked.

‘What about you?’ he then asked, ‘How was your first-time sucking a dick?’

‘Actually, it wasn’t my first time’ I admitted.

‘What?!?!?’ said Ben, with an astonished look on his face.

‘Do you remember Timo, the German exchange student?’ I asked.

Ben nodded.

‘I blew him once in his bedroom in Germany. And he liked it!’ I said with an evil smile.

‘I liked it too’ Ben said.

‘And then, he blew me back’ I added.

‘Sorry, dude. But I’m not sucking your dick’ Ben replied.

‘That’s OK’ I said: ‘I don’t expect you to’

I looked Ben in the eyes and told him: ‘Ben. There’s something else I need to tell you.’

‘What?’ he asked.

‘I think… I think I’m g…’

I stumbled. The g... word just wouldn’t come out.

‘I think I like guys better.’ I managed to say.

Before Ben could say anything, I kept talking: ‘I know you enjoyed getting your dick sucked. There’s a big puddle right here to prove it. But I enjoyed it too, probably even more than you. When you came in my mouth, I almost came too, without even touching my dick. That’s how much I enjoyed it. I’ve never told this to anybody, but I think I’m gay’.

Finally! I said it! I was finally able to say these three words: ‘I’m gay’.

Conflicting thoughts raced through my mind. On the one hand, I felt like a huge weight had been lifted off my shoulders. I had wanted to say these three words to somebody, anybody, for months. But while I was still in high school, I was paralyzed by the possible repercussions: the funny looks in the hallway, the laughing behind my back, the jokes to my face, and possibly even bullying. But now that I was heading to college, I cared less about the consequences. And since I told Ben 5,000 miles away from home, my secret was pretty safe, unless Ben told somebody.

‘Ben, I’ve never told this to anybody. My parents don’t even know. And I don’t think I’m ready to tell them just yet. Can you keep this to yourself?’

‘Don’t worry, Jeremy. I’m no snitch’ Ben responded, ‘And I don’t think I really want people to know I just got blown by another dude’ he joked.

I was hoping this episode didn’t freak him out and wouldn’t change things between us. Although I LOVED having Ben flood my mouth, blowing another guy was something I had already experienced before. What I had not experienced yet was having a dick up my ass, and that was still my ultimate goal. I was afraid that my coming out to Ben would change our dynamics and make my last couple of days in Greece uncomfortable. But I got confirmation it wouldn’t be the case that very afternoon when we went to the beach. When lying on his back, Ben would be adjusting his Speedos in suggestive ways, tracing his shaft in ways that served no practical purpose. He would do that while looking at me, smiling, and pumping one of his cheeks, mimicking a dickhead pressing against the inside wall of his cheek. The immediate effect was that my ragging hardon became even more difficult to manage and there was nothing Miss Nelson could do about it.

On the last day, Ben decided we should run all the way to the top of the hill, which was probably a 2,000-ft climb. That run would get our heart rates way up. The view from the top was magnificent. That’s when I realized we were on a peninsula, and we could see the Mediterranean on three sides. After admiring the view, we went down a little and found a quiet spot.

Ben asked me: ‘So, what do you want to do? Do you just want to jerk off or do you want to blow me again?’

It was my last day in Greece and probably my last opportunity to lose my virginity before going to college. I hesitated a little, looked Ben straight in the eyes, and said: ‘Ben, I want you to fuck me. I’m going to college in a month, and I don’t want to be a virgin when I get there’.

He looked at me without saying anything. And before he had time to say no, I continued:

‘I know it’s a lot to ask from you, but I really want you to be my first one’.

‘Jeremy, I’m a virgin too’ he responded, ‘And I was really hoping my first time would be with a girl, not with a dude’.

‘If that makes you feel better, I was hoping that my first time would be with a guy who has a small dick, not your 7-inch shlong. But I also want my first time to be with someone I trust, not some drunken college student’.

‘Please Ben, don’t make me beg for it’ I continued ‘Trust me, it will only take a few seconds. The moment you break in, I’ll cum in less than 10 strokes. I want it that bad. Don’t even consider it as your first time. Just consider it as practice. It will make you look more experienced the first time you do it with a girl. Please Ben. I know I’m asking a lot from you. Don’t make me beg for it’.

‘I don’t know Jeremy. I’m not gay’ he said ‘Us jacking off together is just two horny teenagers releasing the pressure. No big deal! You sucking my dick is two guys experimenting, kind of pushing boundaries. I wasn’t too sure at the beginning, but I really enjoyed it’.

‘But anal sex, that’s completely different!’ he added.

‘All these jokes about stuffing my ass with your zucchini. And now that you have a real-life opportunity, you’re chickening out?!?!?’ I deplored.

‘Ben, you think I haven’t noticed your little games when we’re at the beach. You think I haven’t noticed how you flex your muscles in front of me, showing off your armpits and your chest hair, just because you already have some and I don’t. And you constantly reminding me that your schlong is bigger than mine. I’m not stupid. I know what you’re trying to do. If you’re trying to establish your male dominance over me. Then go ahead! Dominate me all the way! Stick your big dick up my ass and make me squirm like a little bitch! If you think you’re more of a man than me, just show it to me!’

That seemed to have done the trick, tapping into his competitive side, and waking up his raging hormones.

‘OK Jeremy, I’ll do it. But nobody can know about this’ Ben said.

‘Yeah, like I want the whole world to know that I’m gay and you fucked me up the ass!’ I responded. ‘It’ll be our little secret’.

‘Do you even have a condom?’ Ben asked.

It was in the 90’s, AIDS was still so prevalent that teenage boys had all been conditioned to use condoms, although they weren’t always ready for it when the first opportunity arose unexpectedly.

‘I don’t’ I replied. ‘But since we’re both virgins, we can’t catch anything from each other’.

Ben seemed to be fine with my logic. On my side, I was actually happy that I didn’t have any condom because I really wanted to feel Ben inside me. I wanted to feel his big cock rubbing my inner walls. And above all, I wanted his Greco-Dutch seeds to inseminate my boy cunt.

‘What about lube?’ he asked, ‘Don’t we need something to grease up my dick?’

‘I brought some olive oil. That’s all I could find’ I replied.

Since I’m a planner, I ended up rinsing one of my empty travel-size shampoo bottles, and when nobody was watching, I filled up the shampoo bottle with olive oil from the big jar in the kitchen, hoping I’d be able to put this olive oil to good use with Ben. And that moment had finally arrived.

From our quiet spot, we could see the Mediterranean down below. It was a beautiful sunny day. Every day was a beautiful sunny day in Greece in the summer. There was a big boulder next to a patch of grass. I got down on my knees, spreading my legs apart, exposing my virgin hole to Ben behind me, and I put my hands on the boulder in front of me, looking at the Mediterranean down below.

Ben positioned himself behind me. I turned my head to look behind me and I could see his big fat cock about to impale my inexperienced hole. My dick was so hard I could have lifted a car. But my hole was tight, trying to hold the fort against the invasion, even though I had been craving that invasion for days. Neither Ben nor I had any experience with penetration, let alone butt sex. I had no clue I was supposed to prep my hole and stretch it with my fingers beforehand. All I did was insert one finger in my hole to try to push in as much olive oil as I could. But Ben’s cock was a lot thicker than my finger, a lot thicker.

Ben started pushing his big cock up my hole, but my ring wouldn’t budge.

‘Push harder!’ I ordered Ben, ‘I don’t care if you tear me apart, but we’re not leaving this place until you’ve stuffed your dick inside me’.

I put my hands on my butt cheeks to open my hole wider. Ben forced his way in, and my ring eventually gave way. Ben’s big fat cock wasn’t fully in yet, but at least, his pointy tip had broken through. The pain was excruciating and I felt like a welding torch was blazing my ass.

‘How are you doing?’ Ben asked.

‘You have no idea how much it hurts’ I told Ben ‘Your dick is so fucking big’.

‘Do you want me to pull out? Ben asked.

‘No fucking way’. I responded. ‘Now that you’re in, you have to push through. I don’t care if I die after that’.

My ass was literally on fire. I could relate to the pain of women giving birth, like I had seen in movies. I had never been in so much pain in my life. The entire jar of olive oil in the kitchen could not have eased my pain. It was just basic geometry. Ben’s cock was too thick and nothing even close to that size had ever violated my hole. But strangely enough, my dick was still hard, even harder than the rock in front of me.

‘Keep pushing’ I ordered Ben.

Ben pushed in and I now felt the middle part of his shaft, where it was the thickest, stretch my hole even more than his dickhead already had. It was the most confusing experience of my life. Physically, Ben’s dick tearing my hole apart was pure torture. I couldn’t understand how anybody could ever enjoy sodomy. And I couldn’t comprehend how things could ever get any better. But mentally, my mind was overwhelmed by the thought of having a cock up my ass. I had been waiting for this moment my whole life. And it was finally happening. So many thoughts collided all at once. How could it hurt so bad but turn me on so much at the same time? I was losing my virginity. This obsession, which had been driving me crazy for months, was finally being fulfilled. I never felt so powerless, but I loved it. I was a senior being dominated by a sophomore, but I loved it. I was at Ben’s mercy, but I loved it. How could it be? I had a stiff dick inside me. And not just any dick: Ben’s dick. The one that had formed the bulge in his Speedos, the one that had kept me rock-hard for two weeks straight. The dick of my best friend, the dick of a football player, the dick attached to that amazing body. My best friend, who wasn’t even gay, was giving me a gift that I could never repay, drilling me from behind. His pubes were tickling my butt cheeks and his low hanging balls were pounding against my ass, sounding like the drums of an African warrior. And we were doing all this outdoors, in broad daylight, looking at the Mediterranean. We were breaking so many taboos all at once.

All these conflicting thoughts in my head were like electrons colliding in a cyclotron to create a nuclear explosion. And the nuclear explosion came quickly. I kept my promise, less than 30 seconds, not even that. Just a few strokes of my hand and my first rope shot out of my dick and crashed onto the boulder in front of me. It was the biggest rope to ever shoot out of my dick. I actually heard the sound of my spunk being shot out of my dick, quickly followed by the sound of that big glob of semen crashing against the boulder, forming a huge puddle. It was surreal!

My second volley lasted what felt like an eternity. Instead of my usual quick shot, it felt like I was actually pissing semen out of my dick. The sound of it was like me pissing in a trough at a stadium at half time. But it wasn’t piss, it was cum. And it wasn’t in a trough, it was on the rock in front of me. All my boy juice started dripping down the rock. And then a third and a fourth volley added to the buildup.

I tried not to be too loud since we were outdoors, and I didn’t want to attract any attention. I just whispered: ‘Oh my God, Ben!’ as I shot my first load. But even though very little noise came out of my mouth, I felt like the entire village could hear the explosion coming out of my dick, with the sound of my jizz crashing onto the rock echoing in the mountains.

Luckily, for the sake of my aching hole, Ben didn’t last very long either. My ring was so tight that it must have squeezed his girthy cock, providing way more friction than his hand ever could. And I don’t care if you’re gay or not, there is no way the HUGE puddle of my white cum on the boulder in front of us didn’t turn him on, especially knowing it was his own cock that had pumped the juice out of mine. I felt Ben’s cock expand in my hole and felt hot liquid coating my inner walls. I have no clue how much Ben came versus what he normally cums when jerking off, but it felt like my insides were being flooded by a torrent of warm jizz.

It all went down so fast that the excruciating pain of his big dick destroying my virgin hole never had time to subside. My overstretched hole was on fire. But I had so wanted this. I had so wanted his big cock inside me, that my excitement overcame the pain. We could have been fucking on a burning volcano and I would have overcome it. Even though the pain of his big fat cock splitting me in half was excruciating, along the way, his dick also seemed to hit a spot inside me that I didn’t even know I had. But it all went so fast that I didn’t know if I ever felt it or if it was just my brain playing tricks on me, with the excitement of Ben making me his bitch.

As always, Ben’s cock deflated as soon as he was done shooting inside me. His exit was a lot smoother than his forced entry had been. It still stung a little though. We both collapsed on the grass and lied on our backs, looking at the blue sky above us. We stayed like this for what seemed like an eternity, until I eventually broke the silence.

‘I don’t know how it was for you Ben, but for me, it was incredible. I never came so hard in my life’ I said, pointing at the white puddle of my boy juice on the boulder. ‘I’ll never be able to repay you for all you did for me’.

‘You don’t have to repay me anything’ Ben said, ‘I came a lot too. It felt so different from jerking off. So much better actually’.

‘Did it hurt?’ Ben asked.

‘It hurt like hell. In case you didn’t know, you kind of have a thick one down there’ I said jokingly, ‘But it felt amazing everywhere else. Your first girlfriend will have no clue how lucky she is to have you’.

‘It’s funny’ I added ‘I never pictured that my first time would be taking a dick up my ass. I always assumed I would be the one fucking the other guy. But I’m so glad it happened that way’.

‘I’m glad I could help’ Ben said.

We cleaned ourselves as much as we could and put our shorts back on. On our way down from the hilltop, we stopped by a secluded beach that Ben knew about. As expected, the beach was completely empty and we just skinny dipped to rinse off the smell of man sex before getting home. I had never had to deal with cum dripping out of my ass before and I wasn’t sure how to handle the whole process. Part of me wanted to keep Ben’s babies inside of me forever, but part of me was happy to part with them in the Mediterranean rather than in the bathroom of that crowded house, where Ben’s parents would have heard me. I just went into the water and pretended I was taking a shit. Skinny dipping with Ben in broad daylight should have been a dream come true. But at that very moment, I had more pressing matters to take care of.

I was very self-conscious the entire way back home. We ran into a couple of Greek grandmas, and I felt like the grandmas were looking at me funny, as if they knew exactly what Ben and I just did. And looking at the two of us, they must have known I had been his bitch. I was also mortified at the thought of facing Mrs. Thanos and how the both of us would react when she asked us how our run was. But we managed.

I flew back to the US the next day. I had already left for college by the time the Thanoses came back from their Greek vacation. I never saw much of Ben after that summer. Not that there was anything wrong between us or that we were trying to erase that part of our life. But we just went our own separate ways. Life can be funny that way. College was a completely different chapter of my life, and just like Mike before me, campus life (and boys) consumed most of my time. I only came back home for Thanksgiving and Christmas.

Ben became a starting player on the football team and his popularity grew exponentially after that. I don’t know if tight ends are supposed to score touchdowns, but I heard he did. And then he scored his first touchdown in real life. The girl’s name was Jenny Ambacher. She was a cheerleader. And she’s the one who took his virginity, for real, assuming what we did in Greece didn’t really count. Lucky bitch! Things only lasted for a few months with Jenny, but she was quickly replaced. Apparently, girls were lining up to take her spot, to take my spot. Of course, they were! Ben could get any girl he wanted.

He eventually went on to college. He managed to land a football scholarship. It wasn’t at the likes of Ohio State or Alabama; just a division II school. But between going to a second-tier university for free or a more prestigious one at full tuition, the decision was easy to make. Once Ben went off to college, his parents became empty-nesters and they eventually moved down south. I completely lost touch with Ben and his family. Such is life! But I’ll always remember my Greek vacation, the bulge in his Speedos, his big fat cock tearing my virgin hole apart. And the image of my cum puddle on the boulder will be engraved in my memory forever.

(The End)