The Gay-Cation

I awoke from my slumber a few hours later and saw that it was almost 6pm. I was extremely hungry now, not having eaten since yesterday was taking its toll on me. So, I made the quick decision to jump in the shower and give myself a good wash and clean before getting dressed for the evening. I settled on a pair of chino shorts, a short sleeve button down shirt and a pair of trainers. Underneath, I'd selected a jockstrap that Alvaro had bought. I wasn't planning on looking for sex this evening, but if it found me then I wouldn't refuse it. By the time I made it to the restaurant, it seemed like most people had already eaten, so I had a quiet meal, ate my food, had a couple of drinks, and then headed out to the bar. There were a few people around the bar as the sun was setting and the lights around the hotel were starting to take over. I took a seat at the bar and ordered a drink.

People were coming and going, couples were hand in hand and heading up to the rooms, probably for some awesome sex. I sat there, grinning like a moron, thinking I now know just how good that felt. A few people were dancing around the bar, grinding up against each other. A couple of times people bumped into me, at first it seemed accidental, but then I figured they were most definitely trying to get my attention. A few minutes later, I was sat scrolling through my phone when the barman appeared in front of me, 'a drink, from the gentlemen down the bar.' He placed a pint glass in front of me and I looked to see a much older gentleman there, acknowledging he was the one who'd bought me the drink.

Immediately, I looked at him and thought, 'yeah, I'd let him fuck me.' Which was a new thing that was going on in my head. I'd never looked at other men and debated if I'd let them fuck me. Anyway, the older gentleman had a good head of hair which was grey/silver, he had a beard and was currently wearing a shirt with the sleeves rolled up and from what I could see, a pair of trousers. He was an incredibly attractive man. As soon as he saw me looking, he smiled at me and gestured for me to join him. And I couldn't resist. I picked my drink up and joined him at the other end of the bar.

He offered me his hand, 'I'm Simon,' he said.

'James,' I shook his hand.

'Ah, so you're English,' he laughed. 'That's a relief, otherwise this could've been a difficult conversation.'

'Some conversations have been fun,' I said. 'Especially when you see two different nationalities trying to flirt, but I guess sex is a universal language.'

'It is indeed,' he said. 'So, I guess you already have an idea of why I bought you a drink.'

'Because you'd really like to be friends?' I smiled at him, and he laughed.

'Exactly,' he said. 'And friends can still have sex, can't they?'

'Oh, so that's why you want to talk to me,' I said with a hint of sarcasm. 'I assume you can guess that I'd prefer to be fucked.'

'I could just tell,' he said, placing his hand on my thigh.

'How old are you? If you don't mind me asking.' I needed to know.

'I'm 61,' he said, and my jaw dropped.

'No way, I thought you were in your 50s,' I told him. 'You look good.'

'I have to look after myself to keep up with the younger guys around here,' he laughed. 'Some of them still expect me to go all night.'

'Well, I've only had sex with one person, but I preferred that he fucked me, we went to sleep, then I woke up in the middle of the night, made him cum again and then had him fuck me one more time when we woke up,' I kept eye contact the whole time I told him.

'Let me get the bill and we'll get out of here,' he laughed. 'So, you've only been with one man? I'm guessing it was the guy who was fucking you on his balcony this morning.'

'You saw that did you?' I got slightly embarrassed. 'He fucked me for the first time yesterday afternoon, that was him fucking me again. He wanted to show me off.'

'A lot of people saw,' he said. 'Now you know how I knew you like to bottom.'

'That makes sense,' I said, and then someone else appeared behind us both.

'James, this is Jack, Jack, meet James,' Paul reached out and we shook hands. He turned to face Simon and gave him a kiss. 'We've hooked up a couple of times,' he explained.

Jack looked like he was a little bit younger than I was. But he was tall, slim, and was dressed in a t-shirt and shorts. He had longer hair that reached his shoulders and currently held his fringe out of his face using a headband. 'You're cute,' Jack said to me. 'You look like you might be my age.'

'I'm 26,' I told him.

'26?' He seemed shocked, 'I'm only 22, you don't look a day over 21,' how flattering I thought, if they wanted to have sex with me, all they had to do was ask.

'Jack likes to be fucked and do the fucking,' Simon said. 'And he hasn't had chance to do much fucking on this holiday.'

'That could all change very soon,' I said cheekily. 'I mean if that's what all this is about. I don't imagine you bought me a drink just so we could talk?'

'Would you like to join us down on the beach for the sunset?' Simon smiled. 'I have blankets and extra drinks.'

'That sounds wonderful,' I said, and we stood, Simon revealing he was much taller than me, probably about 6ft 5 and of course Jack was taller than me as well. We started walking and soon found ourselves on an empty beach, but Simon kept going until he found a secluded spot, away from prying eyes. Once Simon was happy with the spot, he reached into a bag he'd brought with him and pulled out a large blanket which he unfolded and placed it onto the sand. We grabbed a few heavy rocks to hold it into place in case the breeze got up.

Simon handed us both a drink and we all sat down, taking in the glorious view of the sunset we had. We had a couple of drinks while we chatted, mainly, I think we were seeing how secluded our little spot was, and no-one had wandered over since we got here. And the wall behind us was doing a good job of blocking the noise from the hotel.

'Well then,' Simon said and reached into his bag, 'anybody want these out ready, just in case?' In his hand, he was now holding a pack of condoms and a bottle of lube.

'Come here,' Jack said to me, as we both placed our drinks down and moved closer to one another. He leaned in first and we started kissing. No tongues at first as he kissed my lips whilst placing his hand on the side of my face.

'Oh fuck,' I moaned as he moved his kisses to my neck before returning to my lips and this time, he pushed his tongue into my mouth. Our eyes closed, we had no idea what Simon was getting up to, but I imagine he was enjoying the show. Jack's free hand worked its way to my lap and started rising until he reached my groin and started to stroke my hard cock through my shorts.

I started reaching around, trying to find his leg until my hand eventually landed on his knee, and then I was able to work my way up to his cock, which felt quite impressive, but it was difficult to gauge the real size through his clothes. We continued to kiss, while our hands roamed each other's bodies. Jack kept reaching around to squeeze my ass, and then he complimented me on my ass before telling me how he couldn't wait to be inside me. At that point my cock twitched inside my pants.

'Ahem,' Simon made his presence known behind us. Me and Jack both laughed, we were getting well into each other before Simon reminded us, he was there. 'I think you should both undress each other.'

Me and Jack looked at each other, and then smiled before standing up. As soon as we were on our feet, Jack started kissing me and unbuttoning my shirt. He then slid my shirt off my shoulders and on to the floor before I briefly broke off our kiss to be able to remove his t-shirt. I went to kiss him again, but he avoided my mouth and bent himself over slightly so he could start kissing my nipples. I ran my fingers through his hair as he continued to kiss my nipples and let his hands run across my chest and torso. Then he started to fumble with the buttons of my shorts, but they were more difficult to access because my cock was acting like a tent pole in my shorts. He finally managed to undo them, before pushing them down my legs, revealing my jockstrap underneath with my hard cock poking out the top.

'Very nice,' Jack said as he started to jiggle my ass cheeks. And I leaned into his neck, trying to tease him by kissing him. 'Do you approve?' He asked Simon.

'Very much so,' he agreed and when I looked over, he was rubbing his own cock through his trousers.

Jack squatted down in front of me, helped me to step out of my shorts and shoes before placing a quick kiss on the tip of my cock. When he stood up, I wanted to go one better. I hooked my fingers into the waistband of his shorts and quickly pulled them down. Underneath he was wearing a black thong which had a cock pouch. I helped him out of his shorts, and his shoes before I just sat staring at his cock.

'Here goes nothing,' I thought as I rubbed the front of his pouch before pulling it to the side to reveal his cock. His cock and balls were hairless. His cock was roughly 7 inches I would say, maybe more but he was bigger than I was. He was almost fully hard as I started to lick my way from the base of his cock, all the way to the tip. I looked up to see him looking slightly shocked and turning to look at Simon who had a smile on his face. I took the head of his cock into my mouth and started to work my way down his shaft until his cock hit the back of my throat.

'Oh fuck,' he moaned. 'And you hadn't done anything like this before yesterday?'

I let his cock fall out of my mouth, 'nope.'

'Liar,' he laughed, and I put his cock back in my mouth. He placed his hand on the back of my head and controlled how deep his cock went. He pushed me all the way down onto his cock and held it there for a little while before he finally let me go and his cock fell out of my mouth covered in saliva and I quickly dried my mouth with the back of my hand. 'I think we're forgetting someone,' Jack said.

Both of us, just in our underwear made our way over to Simon. We helped Simon to his feet, then he started to kiss Jack as I unbuttoned his shirt and helped him out of it. He was slim underneath the shirt; he was in such good shape for his age. We then swapped; he started kissing me as Jack helped him out of his trousers. Simon had his arm wrapped around my waist and kept playing with my ass, sliding his finger up and down the crack of my ass before gently teasing my hole. Jack was now on his other side and Simon was squeezing his ass.

'How did I get so lucky?' Simon laughed.

'May I do the honours?' I asked, placing my finger inside his briefs.

'Be my guest,' he said, and Jack stood to the side, so I had room to get down in front of Simon.

I dropped down onto my knees, and I already could see the impressive shape of his cock underneath his briefs. But I wanted to see the real thing. I started to pull his briefs down until his cock popped out. Fuck. It was big. Bigger than Alvaro, not by much but he was a lot thicker. I took it into my hand and started to gently stroke it. I teased him by swirling my tongue around the head of his cock. I tried to take him into my mouth but barely got a couple of inches in before it became uncomfortable. Jack dropped down next to me to show me how it was done. He started sucking Simon's cock, so I started to focus on his balls and between us we soon add him moaning and groaning.

'Oh fuck,' he moaned. 'Such good little sluts, I chose well tonight.'

Me and Jack alternated, taking it in turns to focus on Simon's cock. The more I sucked it, the more I was able to take down my throat. At one point we both played with his cock at the same time, our tongues meeting as we both worked his shaft. I had a hold of Jack's cock at the same time, which was still hanging freely outside of his thong. I could feel the head of his cock was leaking pre cum. I was surprised I hadn't cum already I was so turned on.

'Jack,' Simon put his hand under his chin and lifted it, so he was looking him in the eyes. 'I think it's time I fucked you, give James here a preview of what's to come.'

Jack quickly got to his feet and went searching for the lube to get his ass ready. That gave me some one-on-one time with Simon, and I made sure to take advantage of the couple of minutes I had. I sucked his cock for a little while before standing up and letting his cock rub against my ass. I bent over, exposing my hole to him and felt him rubbing his cock up and down the crack of my ass. Jack, meanwhile, was ready. He had discarded his thong, and had made a pile out of all our clothes to lift his ass off the beach ever so slightly. He was now on his back, his legs spread, and Simon was ready.

'What are we saying boys, condoms or no condoms?' Simon said, we all quickly agreed no condoms and Simon walked over to where Jack was, dropped onto his knees and positioned the head of his cock at his hole, ready to penetrate him. He lifted one of his ankles onto is shoulder and spread Jack's other leg wide. As he pushed himself inside, it was obvious that Jack was accustomed to taking his cock. There was little resistance and he quickly pushed himself balls deep as Jack started to moan. I laid down beside them and watched this beautiful act take place in front of me. I watched intently as Simon's cock slid in and out of Jack's hole with ease.

'I love your big cock,' Jack moaned as he took whatever Simon could give him.

I leaned over and started to kiss Jack, feeling kind of left out, I wanted to be involved. I wanted to be the centre of both their attentions. As he kissed me, he moaned into my mouth, and I reached down for his cock and slowly started to stroke him back to life till he was fully hard.

'I think you should sit on his face James, let him get your ass nice and wet,' Simon butted in.

I didn't see any reason why I shouldn't, so I let go of Jack's cock and swung my leg over his head, so I was almost sitting on his chest. He freed his arms from in between my legs and I shuffled back slightly so I was nearer to his face. I felt him press his face against my ass and then his tongue started to work its way around my ass. Immediately my cock was twitching inside the jockstrap and then I felt Simon's large hand around my neck as he pulled me forward so I could kiss him. He broke off the kiss and I locked eyes with him and all I could think about was having his cock inside me.

'Your tongue feels so good on my ass,' I told Jack as I started to jiggle my ass up and down causing his tongue to hit all different parts of my ass and taint. I reached forward and grabbed Jack's cock once more, this time though I moved myself down on top of him so I could take him into my mouth. I was soon bobbing up and down on his cock with a perfect view of Simon's cock sliding into his ass.

'I hope you're saving that load for me,' I said to Simon, whilst stroking Jack's cock.

'It's not just my load you're getting,' he smiled. 'We both plan on filling you up before you go.' I went back to sucking Jack's cock and Simon encouraged me with hand on the back of my head to make sure I kept taking him deep.

'How long till I get to feel a cock inside me?' I decided to be bold, it felt like I'd waited and watched for long enough.

'Are you ready for him Jack?' Simon said, Jack muffled a response, but it sounded enough like a yes, that Simon pulled his cock out of Jack's ass and sat back and started to stroke himself slowly.

'Where do you want me?' I asked Jack as I climbed off his face, even though I could've stayed there all night but the need for a cock inside me overruled that feeling.

'Stay on all fours,' Jack told me as he climbed up onto his knees and reached for the lube.

He rubbed a generous amount on my ass and slid a finger inside me. And now he started to finger me, exactly how I would finger Heather before I fucked her. He quickly worked his way up to two fingers and was really pushing them deep inside me, brushing against my prostate every time. My head rocked back, enjoying every second until Jack had me begging for his cock.

'Please fuck me,' I begged him. 'I need to feel you inside me.'

Thankfully, he didn't deny me any longer and I soon felt the head of his cock pushing against my ass. He pushed forwards and my ass opened for him so he could push himself inside. Once the head of his cock pushed past my sphincter I was in heaven. Jack kept edging himself further inside me until I felt him press his body against mine. Jack slowly started to rock backwards and forwards until my ass was ready to be fucked. Once he was able to enter me more easily, he started to pick up the pace and was soon fucking me harder. His balls were soon slapping against my body, and I was just there, gripping onto the picnic blanket with my face buried in it as I just moaned. I knew my cock wouldn't be hard but that didn't take anything away from the pleasure I was feeling.

Soon after Jack really started to fuck me, I felt Simon appear in front of me. He pulled my head up gently so I was eye level with his cock, and he just said, 'suck it', and waved his cock around in front of my face. When it stopped moving, I opened my mouth and managed to get it into my mouth and start sucking. I couldn't use my hands, because I panicked and thought Jack would knock me off balance while he was fucking me.

'What a perfect evening,' Simon moaned. 'We hit the jackpot finding this one. I didn't think we'd have him spit roasted this quickly.' They high fived above me, and it turned me on, thinking that I was some sort of conquest for these two. They'd obviously seen me about and had chosen me for tonight.

Jack took a tight grip on both my hips and started to fuck me harder, and I was now just moaning around Simon's cock as he continuously rubbed his fingers through my hair. He was really slamming himself inside me now, almost like he was trying to force himself to go deeper, even though I don't think it was possible. 'I love fucking a tight ass,' Jack moaned. 'He's fucking milking my cock.' I started to meet his thrusts, not that I wanted him to cum early, but I wanted to push him to the edge. I wanted him to be on the verge of cumming and I knew he must've been getting close. He kept trying to slow the pace, but I wouldn't let him.

'Fuck, fuck, fuck,' he grunted before quickly pulling his cock out. 'I can't, otherwise I'm going to cum.'

Simon laughed, 'looks like I need to step in then,' he let his cock fall out of my mouth. 'I think you should ride me first.'

I stood up whilst Simon got himself onto his back, his big, thick cock standing to attention. I made sure to lather him in lube before doing the same to myself and then started to lower myself down. 'Take your time,' Jack told me as he held Simon's cock steady as I lowered myself down until I felt the massive head of his cock trying to invade my ass. It took a couple of attempts of slowly lowering myself down until finally his big cock pushed past my assholes resistance and entered me.

I yelped slightly at first, 'fuck it's so big.' As soon as I had enough of him inside me that I could start riding him, Jack let go of his cock and held my hands, providing me with some much-needed balance. I started slowly bouncing up and down, trying to take more of Simon's cock each time. I could feel my hole stretching to accommodate his girth. Whenever I took more of him inside me, I would take some time adjusting to his cock before lowering myself down again.

'Big, isn't it?' Jack said with a big smile on his face.

'It's fucking huge,' I moaned. And after what felt like a lifetime, I felt my ass cheeks land on his body, meaning I'd taken his full length inside me. 'Ohhhh fuck,' I let out a long moan.

Now I had him fully inside me, I started to grind myself on his cock, feeling him rub against my prostate which had me in heaven. As Jack held onto me, I started to bounce, the noise of our bodies meeting started to get louder, and so did my moans. His cock just felt so good inside me. I was starting to wish I'd done this a lot sooner. Simon had let me have full control for now, but I don't think he was used to that, and I think he wanted to take more control. He had me reposition myself, leaning back and placing my hands either side of his body so he could start to fuck me. I felt his hands grab onto my hips shortly before he started to drive his cock inside me. My own cock started flapping around my body, but Jack made the quick decision to muffle my moans by standing above me and feeding me his cock. I started sucking, and moaning all over his cock. Simon's continuous driving into my ass had me feeling all kinds of strange feelings. I had a mixture of feeling like I was going to cum or pee. And I didn't want to let it go in case it was the latter.