The Gay-Cation

‘All I’m saying is, I’m very experienced,’ he winked at me. ‘Why don’t we go to some shops before you run away?’ He laughed and we left the bar. Alvaro took me to numerous shops around the little town near the hotel. Given it was Pride month, there was a lot of LGBT things taking place and Alvaro seemed to know a lot of people in the area. As we headed into the afternoon, Alvaro said he had one more shop to go into, after that we could return to the hotel. He asked me to stay outside whilst he went in, and he returned about 10 minutes later carrying another bag to add to the others he had from the other shops.

As we approached the hotel, we turned and started walking down the entrance way to the hotel lobby. Alvaro turned to me, ‘did you enjoy what you saw yesterday?’

‘What do you mean?’ I asked him, knowing exactly what he meant.

‘The action around the pool,’ he confirmed before looking at me for an answer. I tried to speak but stuttered, I couldn’t bring myself just to say yes. ‘It’s okay if you enjoyed it, it doesn’t change anything about you.’

‘It’s the first time I’ve seen anything sexual in real life,’ I told him. ‘That obviously doesn’t include me having sex. It’s the first time I’ve been a voyeur,’ I tried to clear up what I was saying.

‘But did you enjoy it?’ He asked again.

‘I think the outcome of yesterday says I did,’ and I felt myself blushing immediately.

‘What if I offered to show you something else?’ He suggested.

‘Like what?’ I hesitated, not knowing where this could lead.

‘Just follow me,’ he said and walked off in front of me into the hotel lobby. I followed along as we walked through the hotel and to the pool. The pool area was busy given it was an extremely warm day, but nothing exciting was happening but we weren’t stopping here. We carried on around the side of the pool and eventually found the stairs to the private beach. I made it halfway down the stairs before I saw exactly what Alvaro wanted me to see. ‘What do you think?’ He turned and looked at me.

I just stared. There wasn’t lots of people on the beach. A handful of people were sunbathing on towels and all of them were naked. And those people were acting like nothing was going on around them even though two people were currently having sex. One guy was on his hands and knees on a towel as some other guy fucked him from behind. I was shocked that this was happening out in the open in front of everyone, even after what I’d seen yesterday. The guy getting fucked kept throwing his head back and I could hear his feint moans despite how far away we were. I could feel my cock starting to stiffen in my shorts. My mind started to wander, and I quickly found myself standing there imagining that feeling. Imagining how it would feel to have another man do that to me.

‘How does this make you feel?’ Alvaro got close to me and spoke quietly in my ear. He ran his hand across my back and kept going lower until he was touching my ass.

I gulped, ‘turned on,’ I told him.

‘I thought you would,’ he moved his hand again until he brushed it against my cock. He then put his hand around my waist as we both watched this sexual act taking place in front of us. After a little while longer he leaned in towards me again, ‘what would you say if I asked you back to my room?’

‘I’d say yes,’ and I felt butterflies in my stomach.

Alvaro held out his hand which I took, and we headed back off up the stairs, around the pool and into the hotel. I wasn’t sure how many people knew I was straight but as we walked around the pool, I could see multiple people smiling at us as Alvaro guided me into the hotel lobby and up the stairs to the second floor where his room was. He was a couple of inches taller than me as well, which made me feel slightly more submissive to him. As we entered his hotel room, he closed the door and locked it behind him. He hadn’t opened his curtains so far, but that soon changed as sunlight flooded into the room and he had a clear view of the pool.

‘Why don’t you take a cold shower?’ He suggested to me, ‘and take this bag with you, hopefully you see something in there you like.’ He also pointed out some other things I might be interested in doing whilst I was in the bathroom. So, over the next half hour, I cleaned, shaved, and spent time standing under the shower head wondering whether what I was about to do was the right thing. Really, I didn’t even know what I was about to do. Whatever was going to happen, I assumed Alvaro would take the lead.

Once I climbed out of the shower, I dried off and looked into the bag that Alvaro gave me. Inside the bag were multiple pairs of underwear. There were thongs, briefs, and jockstraps. I looked over the underwear and held each one in my hand before my curiosity was piqued by a red thong. I pulled it up my legs and my cock and balls fit snugly into the pouch at the front, and my ass looked good in the mirror. I pulled my shorts back on and headed back into the room. Alvaro was standing there, in just his swimwear, ‘fancy a cold one on the balcony?’ I thought that was a good idea, he handed me a beer from his mini fridge, and we took a seat on the balcony.

We talked on the balcony for what seemed like forever, we watched the people around the pool. A couple of people were getting frisky before they’d get up and head either down to the beach, or up to their hotel rooms. Alvaro explained how most things were okay around the pool, but some things were frowned upon, mainly sex. But as we looked around at other balconies, we could see a few people had moved their fun up there. At least 3 different balconies were currently being used for sex and seeing that started to turn me on.

Alvaro moved forward to the edge of the balcony and then turned to look at me, ‘take a look at that up there,’ he pointed. I climbed out of my chair and moved to the balcony rail and looked up. A few floors above us, someone was getting fucked and all you could see was his cock bouncing between his legs with the cock sliding in and out of his ass. I sat back down and felt my shorts slide down slightly, ‘excellent choice,’ Alvaro said to me and winked. I took a sip of my drink again before Alvaro said to me, ‘what made you say yes to joining me up here?’

‘I guess you could say I’m curious,’ I told him before avoiding eye contact.

‘So, what is it you’d like to try?’ He asked and I could just tell he was loving it.

‘I was hoping you’d take the lead on this,’ I said, and those butterflies returned.

Alvaro stood, smiled at me, and offered me his hand once more. I took it and followed him back inside the hotel room before he turned to face me. He put his hand on the back of my head and brought us closer together until he kissed me. I suddenly felt like I was floating as he held the kiss for a long time before he broke off the kiss. ‘We are still good?’ He asked.

‘Yep,’ I said without hesitation.

He kissed me again, only this time I felt his tongue pushing at my lips until I opened them, and his tongue worked its way inside my mouth. He dropped his hand off my head and eventually wrapped both his arms around my waist and I reached up to wrap mine around his neck. This all felt sensual, but more importantly, it felt right. His hands moved to my ass, and he pulled me as close as he could towards him, my cock pressed against his body, and his against mine. The kissing continued and I had the strange feeling of feeling slightly feminine whilst this man I barely knew grabbed at my ass and stuck his tongue down my throat.

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