The Gay-Cation

Eventually, after the constant pleasure to my prostate, my legs turned to jelly, and I could no longer hold myself up. I collapsed onto Simon's cock, driving it deeper inside me to the point I had to climb back off because he went a little too deep. I had to lay down to catch my breath, but Simon wasn't interested in any sort of break. He quickly had Jack on all fours and was fucking him from behind making him scream with pleasure.

I watched them fuck for what felt like an eternity. It gave me time to recharge my own batteries, and I played with my own cock whilst watching Jack get fucked like a rag doll. Hopefully one day, that's how I'll be getting fucked, but it still may be too early for me. By the time I was ready to join back in, Jack had been flipped over and was getting fucked in the missionary position again. Simon had his hand wrapped around Jack's cock and was slowly jerking him off, and Jack was enjoying every second. Maybe a little too much, he looked like he could cum at any moment and slapped Simon's hand away.

'James, sit on his cock while I'm fucking him,' Simon told me. 'It won't take him long to fill you up.'

It took some figuring out, but Simon released Jack's legs as much as he could until eventually, I was able to climb on top of Jack with my back to Simon and started to feel around for Jack's cock before finding it and lining it up with my hole. It slipped in with ease this time and I started to ride him while Simon got back to fucking him. I bent over so I could kiss Jack whilst I did my best impression of twerking on his cock until he started to warn me that he was going to cum soon. I sat back up and put all my efforts into bouncing on his cock. Simon wrapped his arm around me from behind and started kissing my neck.

'Fuck,' Jack moaned. 'I'm cumming.' As I bounced on his cock, I watched as Jack started to squirm before his cock started pulsing inside my ass and he started to fill me with his cum. The warm feeling of his cum inside me, almost made me reach for my own cock to make myself cum but I still had Simon's cock to think about. Once Jack had finished cumming, I climbed off him and his cum immediately started to leak from my ass. And I'd now decided that cum leaking from my ass was the best feeling in the world.

When I stood up above Jack, Simon immediately pulled my jockstrap down my legs and threw it away to the side. Jack rolled away and Simon had me lay down on my back. One of my legs was spread wide and Simon picked the other one up and rested it on his shoulder. He put some more lube on his cock and pushed himself inside me. I immediately felt that wave of pleasure and my cock showed it as a trail of pre cum started to appear at the head of my cock. I gripped onto the blanket and threw my head back.

'Oh fuck,' I screamed. 'I need to cum soon, this feels to fucking good.'

'Nearly there,' Simon replied and quickened his pace. He was really slamming himself inside me now and soon started to breathe heavily and I could tell he was close.

'Fill me up, please,' I screamed at the top of my voice.

'Arghhhhh, fuck,' Simon moaned, and he thrust himself deep inside me one last time before he held himself there and I felt his cock starting to pulse. And it must've pulsed at least 6 or 7 times before it stopped. He then withdrew his cock from inside me and Jack practically jumped headfirst onto my crotch and took my cock into his mouth.

He swirled his tongue around the tip of my cock, and after everything I'd been through tonight, that was all I needed. I started to squirm and writhe on the blanket as I filled his mouth with cum. He continued to suck me until I couldn't take it any longer and had to stop him. We all took some time to recover before sharing one last kiss and going our separate ways. I immediately headed back to my room, showered, and climbed into bed.

I slept and I slept well. Turns out being fucked can really make your tired. I didn't wake up till noon the next day and had already missed half of my last full day. I climbed out of bed, showered, cleaned my ass, and then got dressed to head down to the pool for some snacks and a cold drink. I checked my tan lines out in the mirror, and they looked like they were coming along slightly. I was going to go back home looking like I'd barely seen the sun. So, when I got ready, Alvaro had bought me one thong swimsuit, so I put that on, covered it with some shorts and went on my way.

I'd been around the pool for a little while and received some admiring looks from passers-by as I laid there in my thong with a little bulge showing off my cock. Not sure how many people checked me out when I was laying on my front, but I was hope there was more than a couple. After a while, I made my way over to the pool bar, ordered an iced drink and some snacks. As I sat quietly eating my snacks, a familiar Irish accent appeared from behind me.

'Knew you wouldn't survive,' the voice said, and I turned around to see Paddy walking towards me, dressed in a t-shirt and jeans.

'I'm saying nothing,' I smiled and then said, 'I don't know what you're talking about.'

Paddy laughed, 'you've probably had more cock than I have on this holiday.'

'There's still time for you to catch up,' I said jokingly.

'Not much,' he said. 'My airport transfer is in just over an hour; my holiday is over.' I supposed that explained the ridiculous outfit he had on in this heat.

'That's a shame, I thought we were just getting to know each other,' I slyly smiled at him. 'You must've seen some action, a good-looking guy like you. And you've got the accent that makes people weak at the knees.'

He laughed, 'I would like to say I got some action, but I got none. Turns out a lot of people think I'm a bottom, don't know why they do, but I much prefer putting my cock in someone.'

'Is that so?' I looked at him, 'and you've not managed to find someone to take your cock.'

'Well, there is one guy, but the day I met him, he told me he was straight, but then I saw him taking cock a couple of days later.'

'Typical straight boy,' I laughed. 'What if that guy was interested now, would you have time?'

'Definitely,' he smiled from cheek to cheek. 'I think I could squeeze a quicky in.'

'Should we head to my room then?' I suggested.

'We'll have to,' he laughed. 'I've already checked out.'

'Shall we?' I stood from the pool bar and Paddy did at the same time. We both walked to the elevator and headed for my room. As soon as the doors closed, I started to kiss him, letting him feel me and getting me all excited for what was about to happen. At one point someone joined us in the elevator, and we broke off our kiss and I stood in front of him, and he continued to squeeze my ass and push himself against me until we eventually made it to my floor.

I fumbled with the key card to get into the room, but it wasn't helped by Paddy who was still groping me until we got into the room, and he immediately pushed me against the wall when the door was closed and kissed me again. It felt slightly strange being dominated by a smaller man, and most likely a younger man, like this, but I was all for it, he had me wanting to bend over for him there and then so he could fuck me. While he was kissing me, he quickly pulled my clothes off, first removing my shirt and then my shorts, leaving me in just my thong.

'The thong stays on,' he said as his hand brushed against my cock. He lifted my chin and started kissing all around my neck and I struggled to keep myself upright. My hands were flat against the wall. 'Let's get to the bedroom,' he said and led me by the hand before turning and pushing me onto the bed.

Paddy started removing his own clothes and neatly piled them on the chair in front of the dresser. As he removed his briefs, a nice cock popped out. He had some nicely trimmed pubic hair surround his cock and balls. And his cock was a decent size. Not as big as the other cocks I'd had on this holiday but big enough to do the job. As he was getting undressed, I rolled around onto my front and started sucking his cock whilst laying on the bed. I took my time, slowly licking my way around the whole of his cock and making sure to get his balls as well.

He reached over and slapped my ass, 'do you realise how good you look from this angle?'

'But do I look better like this? Or like this?' And I changed my position and got up onto all fours and arched my back.

'Fuck,' he muttered. 'Definitely like that,' and he started to squeeze my ass cheeks while I worked his cock.

I carried on slobbering all over his cock, but kept a keen eye on the time. There was no way I could let this run over and not have him fuck me. I started deepthroating him, placing my hands on his ass and pulling him towards me, driving his cock deeper into my throat until I could barely breath and started to gag. I kept shaking my ass for him, trying to make it so that he couldn't resist and that he wanted to fuck me. But in the end, I think he was going to make me beg for it.

'Do I have to remind you how long you have till your airport transfer?' I looked at him whilst stroking his cock, 'or are you going to fuck me now?'

'Where's the lube?' He asked almost immediately.

Shit, I thought, I didn't think there was any in the room until I remembered there was some in the bag Alvaro gave me, 'in the bag, in the bathroom,' I told him, and he quickly disappeared while I repositioned myself on my back and pulled the thong to the side.

When he came back, he smiled when he saw that I was already in position. Lube was quickly spread around my hole and then all over his cock before he was sliding himself inside me. 'Oh, fuck yes, just what I needed,' I moaned as Paddy quickly got into a rhythm with his fucking. I had my hands wrapped underneath my knees, keeping my legs spread for him and focused on his cock driving in and out of my ass. I paid zero attention to my own cock; I wanted Paddy's cum and that was my only concern right now.

'You're fucking me so good right now,' I moaned at him. 'Do you like my tight ass?'

'You've turned into a little cock slut, haven't you?' He smiled.

'Did you want to fuck me when we met that first time? I bet you did, didn't you?' I managed to say in between his thrusts which made me moan.

'Of course, I did, even more so when you told me you were straight,' he said. 'I think it's safe to say you're NOT straight anymore.'

'I'd rather be the one getting fucked now,' I moaned.

'Good,' he knew he was in control and had me to do whatever he wanted. 'Now, give me those legs.'

He grabbed my legs and pulled them together and then bent them, so they were moving towards my chest. He was folding me like a pretzel and not once did he stop fucking me. Paddy then lowered his head towards me and started to kiss me before placing his hand gently round my throat and pounding me. I could do nothing but moan and whimper, begging him for more. The only time he stopped fucking me was so he could bring my ass further off the bed, but his cock was soon back inside me and I could feel my ass jiggling every time he drove himself back inside me.

After a little while longer, he pulled his cock out of my ass and threw a couple of pillows onto the floor. 'Come here,' and he picked me up from the bed and kissed me, my legs felt like jelly, but he guided me down onto the floor. 'You're about to experience my favourite position, you'll love it.' And he guided me through getting into position. First, he had me get down on all fours before he knelt behind me, resting on one knee. When he was behind me, he picked up my right leg and placed it across his knee, almost tilting my hips and turning me into a right angle. He kept one hand on my raised leg and the other guided his cock back into my hole before coming to rest on my body.

At first, it seemed like he was only putting the tip of his cock inside me and pushing inside me with a couple of inches before pulling out and doing the same thing. And then he pushed himself all the way in, 'fuck that's so deep,' I screamed as he brushed against my prostate and kept doing so in this position. He was like a Duracell bunny, and he just kept going. Thrust after thrust, my prostate was taking a good massaging and I had that weird feeling from yesterday. It felt like I could cum, but at the same time I needed to pee, but I didn't say anything to Paddy. I just continued to let him have his way with me.

'Fuck, you're so deep inside me,' I kept moaning repeatedly. It just felt so good, and my brain didn't seem to come up with anything else to say. The feeling inside me seemed to constantly grow, and I started to panic, thinking I was going to pee myself while Paddy fucked me. But at the same time, I was enjoying it far too much for him to stop.

'Oh yeah, bottoms love it when I fuck them like this,' he grunted while fucking me.

We held this position for another 5 minutes and that feeling continued to grow inside me, almost to the point where it felt like I was holding it in. But as Paddy slowed down, the pressure on my prostate increased and almost felt more purposeful. I knew my cock would be leaking like a tap every time he pushed inside me, but then this feeling inside me grew to a point that I didn't think I could hold it in anymore.

'Oh fuckkkkk,' I moaned as my body started to tremble, my legs started to shake, and it felt like an orgasm was rising through to my cock. Then my cock started shooting but I didn't know what, my cock was still soft so I didn't think it would be cum. But as I looked down between my legs, I saw cum leaking through my thong. Not pre-cum either, proper cum and lots of it. 'Fuckkkk.'

'Did you just cum?' He asked, almost sounding out of breath.

'Yes,' I whimpered as cum was still leaking from my cock and I was still on the come down from the most amazing orgasm I'd ever experienced.

He withdrew his cock from inside me and helped me gently onto the floor while I recovered. He stepped outside onto the balcony for some fresh air, and I barely moved. I couldn't believe what had just happened, but I wanted it to happen again. After a few minutes, Paddy reappeared in the bedroom from the balcony, 'I've got about 5 minutes,' he said.

I slowly pulled myself to my feet, 'well, we better make you cum then,' and I walked over to the balcony glass and placed my hands out in front of me. Paddy quickly lubed himself back up again and started fucking me in the standing doggy style position.

I was a lot more sensitive this time, so didn't know how long I could take it, but I don't think Paddy was planning on it lasting much longer. He gripped my hips tightly and pounded me once again. I was pressed against the glass from the force that he was fucking me, and then he started to grunt. 'Arghhhhh fuck yeah, take it.'

'Give it to me,' I told him. 'Cum for me.'

'I'm cumming,' he groaned as he started to fill me up. And his orgasm seemed to last an eternity, he must have unloaded weeks' worth of cum inside me and I could feel his cock pulsing for a long time as the warm cum continued to fill my ass. When he was finally done, he pulled his cock out of my ass and a load of cum followed it, covering the floor. He left me there whilst he disappeared into the bathroom to clean up, and by the time he came back, I'd moved to the bed with cum still leaking into my thong. We exchanged numbers and one last kiss before he departed. I'd never forget this holiday, but I'll never forget the way he fucked me and made me cum.

For the rest of the day, I had a quiet one. I went down for some food and then packed my suitcase ready to return home tomorrow. While I had some free time in the afternoon, I went and did some shopping and all I came back with was more underwear, more specifically, more thongs. I didn't want to go back to boxers, so I needed some new underwear for the flight home after I'd ruined what Alvaro bought me. When I woke up the next morning, I was in the same position as Paddy. I was dressed for my flight home. Although, I dressed more sensibly, I was wearing a t-shirt, some shorts, and trainers. And underneath I had one of my new thongs on. I dropped my bags off at reception and was hanging around in the hotel lobby. I had a few hours to waste so was just reading a book when I saw a young man arrive to check in. I could see he looked a little nervous and as the staff guided him to his hotel room he walked past, and I smiled at him as we made eye contact.

A short while later, he reappeared in just an open shirt, and a pair of swim shorts with flip flops on. He wandered around for a little bit, until he came over and sat on a sofa near me. And as I kept on reading my book, I could see that he was trying to catch my eye. After the holiday I'd had and the experiences that I'd been through, I made the effort to speak to him.

'Is this your first time here?' I asked him, and he looked across at me and smiled.

'Yeah,' he said nervously. Thank god he was English, otherwise this conversation might have been over quickly. 'I've never been anywhere like this before.'

'Me neither,' I told him. 'I didn't even know what this place was when I got here.'

'Really?' He laughed and seemed a bit more relaxed.

'Yep, but it's safe to say I'm leaving as a different man,' I said.

'What do you mean?' He asked.

'I arrived a straight man,' I began. 'But I'm certainly leaving either as bisexual or possibly gay.'

'I've erm... never done anything with a guy before,' he said quietly.

'And this is where you chose to come for your first time?' I laughed.

'I know,' he continued. 'It was my 19th birthday a few months ago, and no-one back home knows I'm gay.'

'I get it,' I sympathised. 'Sometimes it's easier to come somewhere like this to explore yourself. So where do you parents think you are?'

'A lads holiday,' he said.

'So, do you think you'd like to top or bottom?' I asked the killer question.

'A bit of both, I think, but more of a top,' devious thoughts started to run through my mind.

'Would you like to lose your virginity today?' I asked, and winked at him.

'Really?' He seemed surprised and his face lit up.

'Have you got some lube handy?' I asked.

'In my room,' he said, and I told him to go and get it.

He was back within minutes, so I told him to follow me and found the toilets on the ground floor. Luckily, they were just individual toilets, so we were able to go in and lock the door behind us. 'You have two choices,' I said to him. 'You can fuck me without a condom and cum in my mouth, or fuck me with a condom and cum in my ass?' He thought about it for a small time before deciding on no condom. 'I'd normally let you cum in my ass, but I have a flight to catch in a couple of hours.'

I then slowly dropped to my knees, and pulled his swim shorts down to reveal an average sized cock. Not to dissimilar to my cock really and I quickly took him into my mouth and ran my hand down his chest as his cock stiffened between my lips. And his cock started to grow until he was an inch or so bigger than me. I continued to suck his cock, taking my time, and making sure I teased him. He was enjoying himself; his head was tilted back, and he was moaning and groaning whenever my tongue touched his cock.

'Slow down, slow down,' he moaned at me.

'You going to cum already?' I teased him.

'I will if you keep doing that,' he said. 'Maybe I could fuck you now?'

'You can fuck me whenever you want,' I told him and stood up in front of him as he started to tug on my shorts until he finally started pulling them down and he saw my thong, and I thought that might make him cum.

I stepped out of my shorts and then bent over the toilet, 'use lots of lube, on both of us,' I told him, and he did. He covered us both, before he started to push his cock inside me, and I immediately moaned. 'Fuck me,' I moaned at him, 'fuck me hard and fast, then I want you to cum for me.'