The Gay-Cation

'You stand out so much,' he smiled. 'We'll get you to blend in.'

'Fine,' I pointed at him. 'If you want to update my wardrobe though, you'll have to pay for it. I haven't got anything left after paying for this holiday.'

We finished our breakfasts before heading out to the shops and a couple of bars. I was enjoying to get to know Alvaro a little more. He told me all about his upbringing, how his parents struggled with the fact he was gay but eventually they were able to move past it. He then explained to me how he was a versatile top, and then he had to explain what that meant. I asked if he was concerned about the risks of STDs from gay sex, but he then said he was taking something called PrEP and that was followed by an explanation of what that was.

'So, what position do you think you'd be in bed?' He asked, a devilish smile across his face.

'I don't know,' I blushed. 'It's not something I've thought about.'

'Not even with everything you've seen and heard the past couple of days?' He was really pushing me for an answer.

'I suppose a bottom?' I questioned my own answer. 'Seems like they might get the most pleasure out of it.'

'I can see why you think that, but for me, you must try both to make a decision, unless you're 100% sure that's what you want,' he said.

'I feel like you're leading me down a dark path here Alvaro,' I laughed awkwardly.

'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.

'Would you mind if I take these off?' He asked, tugging at the waistband of my shorts. 'I'd like to see more of your ass and play with it, if that's okay with you?'

'I'm not sure,' I didn't want to regret anything that could happen.

'We'll take it slow, all focus on you and at any point we can stop,' he tried to reassure me. 'You don't have to do anything you don't want to.'

'Okay,' I told him feeling at ease and more comfortable. He hooked his fingers into the waistband of my shorts and tugged at them as they started to fall down my legs. Once they hit the floor, I stepped out of them, leaving me in just the thong with a rock-hard cock trapped inside it. I felt a little uneasy, being this vulnerable in front of another man, but the way Alvaro touched me, kept sending me to a different world of pleasure.

He squeezed my ass cheeks, 'wow, you have such a nice ass.' He looked over my shoulder to get a better look, 'such a cute butt and so smooth.' He continued to grab at my ass, spreading my cheeks and giving me a playful slap occasionally before he started kissing me on the neck which made me go weak at the knees. He physically started moving me at the same time, directing me towards the bed as I shuffled my feet backwards until I felt the bed behind me, and he pushed me onto my back before he landed on top of me. He kissed me on the lips and then started to kiss his way down my body, spending a lot of time on each nipple before kissing my torso and then his face was just inches away from my cock, my breathing started to intensify. 'I'm not going to touch your cock yet in case it goes off a little... prematurely. But your cock looks magnificent.' He smiled at me, 'if you somehow cum without anyone touching it, then I'm onto a winner.'

Alvaro went beneath my cock, pushed my legs into the air and pulled the thong out of my ass. He gently started to lick my taint and I immediately let out a soft moan. That was a sign for him to continue and he went lower once more, this time spreading my cheeks slightly and lightly brushing his tongue against my asshole. 'Oh fuck, oh fuck, oh fuck,' I moaned as pleasure shot straight through my body and to my cock which I just wanted to grab and jerk off.

'Is that okay?' He asked.

'Oh, fuck yes,' I told him quickly. 'Keep going.' And that's exactly what he did, he continued to lick my asshole and I laid there enjoying every minute of it. Moaning away quietly as he worked his magic on my body. I could feel my ass started to relax as Alvaro kept lapping away at my hole. I was staring up at the ceiling wondering how I'd got myself in this position, and mainly how I hadn't been in this position before now. He moved his tongue in circular motions around the entrance to my ass which was hitting the right nerves and driving me wild, I wanted to grab his head and push it further into my ass.

Alvaro stopped, and I let out a small whimper in the process. 'Stay there, he told me, and I watched him walk into the bathroom, his trunks tenting out in front of him with what looked like a big cock. He quickly returned with a few things in his hand, one of which I quickly worked out was lube. He was soon back on his knees and licking my ass again, so I was happy. When he moved back to my taint and then stopped licking, I already knew what he was going to ask next, but I didn't stop him. 'Can I put a finger inside you?'

'Yes please,' I said after pretending to think about it. I heard a bottle cap pop open, then something cold around my ass which made me jump a little. Then there was some pressure as his finger tried to force its way into my ass. And with some persistence and more lube, his finger broke through. 'Oh, fuck yes,' I moaned again. The finger inside me started to slide in and out of me, and when he was so far in my ass it was like he was pressing a pleasure button inside me which he quickly told me was my prostate. It was making my cock feel like it could explode at any point.

I held my legs open by grabbing them behind the knees, Alvaro slowly continued to slide his finger in and out of my ass whilst he used his free hand to massage my cock and balls through the thong. I told him to stop playing with my cock because I felt like I was close to cumming and the fact he was massaging my prostate wasn't helping one bit. When he pulled his finger out of my ass, I was disappointed, feeling empty once more but soon there was even more pressure. I tried to get a look to see what Alvaro was doing and I could see him trying to slide more than one finger inside me, stretching my hole open. I moaned with pleasure every time he pushed his fingers deep inside me despite my cock going soft now that he wasn't playing with it.

He fingered my ass continuously for another five or ten minutes. I just laid there enjoying every moment of it until he slowed right down, and I could see him looking at me. 'I'm going to keep fingering you until you tell me you want it,' he said with a smile.

'What?' I asked confused, or maybe it wasn't confusion, I was just on another planet at the minute.

'I'm not going any further until you tell me to,' he said again. This time the message was clear.

'Oh fuck,' I tried to tell him what I wanted until he pushed his fingers deep inside me again. 'Please, fuck, please will you fuck me?'

'Are you sure?' He checked with me.

'I've never been surer of anything; I want to feel that cock inside me.' I told him, looking directly into his eyes.

Alvaro removed his fingers from my ass and stood up, my eyes were immediately drawn to his big cock which was still trapped in his trunks. He threw a condom onto the bed from down on the floor where he'd been fingering me which was quickly followed by the lube. I couldn't believe that his cock would soon be inside me. He gathered all the pillows from the top of his bed and told me to stand before he stacked them at the end of the bed. When he turned to face me, I kissed him this time, the first time I had initiated anything between us. I then started playing with his cock through his trunks before he pulled them down and I touched his cock for the first time. I took it into my hands and felt how big it was, bigger than mine. I was a good 6 inches when hard and Alvaro felt like he had a couple of inches on me. This all just felt so right.

'You're going to enjoy this,' he told me before spinning me and pushing me back onto the bed. I shuffled myself so I was on the pillows to give him easier access and then waited. And I watched as he removed his trunks, slowly rolled a condom onto his cock, and then started applying lube, and lots of it. His cock looked so good, and my first thought was to take him into my mouth, but I knew this wasn't the time for that. He pushed me back, so I was laid down, and I felt him applying more lube to my ass before pushing some inside me with his fingers. 'Ready?' He asked me.

'Yeah,' I gulped as he moved forward, and I felt the thick head of his cock pushed against the entrance to my asshole. My legs were spread wide, and he held me by one ankle whilst his other was in control of his cock. The pressure was enormous as he slowly pushed himself against me, I tried to relax the best I could, but it was difficult having never experienced this before. He pushed again and the head of his cock broke through my hole. I almost jumped off the bed, but gripped the bed sheets with both hands, I lifted my shoulders off the bed and watched as a man put his cock inside me. The pressure deep inside me continued as he pushed, stretching my asshole to accommodate his cock.

'I can't take it,' I told him, panicking that his cock was too much for me.

'Ssshhh my handsome boy,' the hand that was no longer on his cock was now pressed against my lips. 'I'm all the way inside you now.' He moved his finger across my lips, and I instinctively opened my mouth, and his finger worked its way between my lips. I treat his finger like a cock and started to suck on it as Alvaro started to rock backwards and forwards slowly, giving me time to adjust to this new feeling.

'Your cock is so fucking big,' I moaned at him as he continued.

'How does it feel now?' He asked, and I appreciated it him checking in.

'So much better,' I told him, and he leaned over to kiss me. 'It feels so good.'

'Fuck, I love breaking in a new guy,' Alvaro said and started to move a little quicker.

Before long, Alvaro was into a proper rhythm, and I was now being properly fucked. I wasn't even focusing on my own cock, the pleasure through my ass was more than enough. As he fucked me, my eyes kept rolling into the top of my head, I found myself staring at the ceiling, not knowing how I was now in this position. If someone had told me that this would happen on this holiday, I'd have bet my life savings that it wouldn't. He was moving in and out of my ass effortlessly, he pushed my legs back, so they were towards my chest, and he placed his hands on my hamstrings and kept thrusting. I was making all sorts of noises, moans, and whimpers. And they were noises I'd only ever heard my ex-fiancé make. If only she could see me now.

'This ass is so fucking tight,' Alvaro moaned before slapping my ass. 'Do you want to try another position?'

'Fuck yes,' I moaned as he drove himself deep inside me. 'What... fuck... would you suggest?'

'Should we try reverse cowgirl?' He suggested quickly.

'Oooo cowgirl,' I laughed. 'Let's do it.'

Alvaro slipped his cock from my asshole and climbed onto the bed. I stood up, trying to balance myself on the mattress. Once he was ready, I turned so I was facing away from him and started to lower myself down, keeping a hold of the thong so it didn't slip back into position. He gripped his cock and held it steady for me as I continued squatting until I felt him against my hole. Then I let him slip back inside me, and slowly started to bounce up and down. I was struggling though as I had nothing to hold onto, until Alvaro grabbed both my hands as they flailed behind me. Now that I had some balance, I started to get really into it. I caught a glimpse of myself in the reflection of the glass and that spurred me on and turned me on even more. The angle of his cock was pushing directly against my prostate, and that new feeling of pleasure was driving me insane.

'You getting tired?' Alvaro laughed when he noticed that I'd slowed down. 'I thought with an ass like that, you'd be used to squats.'

'I have a new respect for people who ride cock,' I laughed back before coming to a complete stop.

'Bend over on your knees and arch your back like a good little slut,' he pushed me off his cock and I did as I was told. Getting into position as quickly as I could before Alvaro was behind me, hands on my hips and fucking me again.

'Oh god yes, fuck me please.' I screamed. Alvaro pushed my legs together, I assumed to make it tighter for him.

This was the best position for me so far. I felt so submissive on all fours, arms out in front of me grabbing onto the end of the bed, moaning with pleasure. I squealed with delight every time he brushed against my prostate. I turned my attention to the reflection again, and I could see most of my facial expressions as he fucked me. He grabbed me by the tops of my shoulders and pulled me upwards, I could see he was also now focused on the reflection in the glass, and he really started to pound me.