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  1. Once upon a time in Italy
  2. Once upon a time in Italy 2

Once upon a time in Italy

Categories True Story, Gay, Consensual Sex, First Time

Author: Enox

Published: 29 December 2017

  • Font:

When I was 18 me and a big group of friends went on a trip to Italy. Before we arrived we had been told that we would have three person rooms, once we arrived at the hotel they however told us that it was going to be only two of us per room. Because of that Daniel and I ended up sharing a room. The two of us were friends back than, although he really was more a friend of another friend of mine than my friend. Anyway. During the second day of our stay I had been eating at a local restaurant with some people but not my room-mate and when I came back I was sweaty and just wanted to take a shower. I however had to realise that I couldn't because he was in there already. So I just sat on my bed waiting and hoping that he wouldn't take to long. He didn't. When he came out however he was naked, probably hadn't heard me coming in. He had a really nice body and little pearls of water were still visible on his skin. I just stared at him and said: 'Wow', without even thinking about it. I instantly blushed red and cringed. Why did I always have to be this awkward? He was just as surprised and shy about the entire ordeal and after a moment of shock and me saying something stupid he simply turned and vanished back into the shower to grab a towel. We didn't really speak much that evening.

The evening after me first seeing Daniel without clothes was tough. I certainly would have needed sleep, but I also had a hard-on and needed to release my pressure. That however I couldn't do, because the reason for my problems was just across the room and I was afraid he could hear me. After everything that happened before I really didn't want to risk that. So I lay there trying to keep my hands from wandering underneath my blanket. I couldn't stop thinking about his body. He had already used the summer to get tanned. His hips, as well as the upper half of the thigh were less tanned than the rest of his body, but without any real tan line. (I assume he had worn wide shorts and swim trunks, that kind that moves a lot during the day.) It looked like he shaved all of his body, except for the lower legs, but there his blond hair was a lot less visible anyway. To sum it up he looked brilliant. Slender with the hint of a six-pack that was meet by lean legs and a wonderful round butt. His penis, for all I could tell, was pretty average but perfectly shaved and overall very much in accordance with the rest of his body. I don't know how it happened but at some point I finally managed to fall asleep.

When I woke up the next morning and looked around Daniel was already gone. I was slightly worried because I would have liked to talk about the last day, than again I was also happy because that meant I could finally take a shower and rub out some of the tension from the last evening.
That evening we meet in one of the hotel rooms with around 20 people. Someone had smuggled in alcohol (either Vodka or Korn, definitely something strong) and we were the evening drinking and playing different games. Daniel was also there, but the two of us didn't really do a lot of talking, just like the evening before. However he also didn't really seem any different and over all was just his usual self. That put me at ease.
When every bottle was empty we started heading to our room. Daniel and I were both drunk, not wasted but certainly in a good mood. We arrived at our room talking about this and that. Each one got into their respective beds and than I had the glorious idea to play truth or dare. At that point I honestly wasn't thinking about anything sexual. In fact the first dare I wanted to give to Daniel was to annoy the fuck out of our friends by going to their door, knocking running away and than repeating the entire process for like three or four times. (That stupid kind of stuff you find funny after a few drinks.) However when Daniel agreed to play and asked “Truth or Dare” I foolishly said “Truth”.

His first question caught me off guard. “Why did you say 'wow' yesterday.” I blushed and failed to answer at first. Than however I came up with what I thought to be a brilliant lie because it was in fact a half truth. I answered him that I was only surprised at how sporty he looked and that once I had said the 'wow' I instantly realised how strange it may have sounded. I am not sure why but he bought it, maybe he was a bit shy.
So now it was my turn and Daniel picked truth as well. So I asked him why he came out naked in the first place. His answer was a pretty simple: “Because I thought you were not in the room.”

When it was my turn he dared me to jump the distance between his and my bed. I made it.....almost. Fell flat on my face, but with the luck of any intoxicated person managed to miraculously only get a small bruise at my elbow. Still not my proudest moment.
It now being my turn he picked dare as well so I dared him to scream some obscenity of the balcony, which he promptly did and with slightly more enthusiasm than I had imagined before. After a few of these pretty standard truths and dares I took all the courage I could muster and asked the first slightly sexual question of the evening. “Have you already masturbated since we arrived at the hotel room?” After I had asked that he just looked at me with somewhat of a blank look on his face. Than he looked away and very silently so I could barely hear it said: “Yes”. I was really surprised by that. I had talked with other friends about this kind of stuff before and all of them were pretty open and casual about it.

Ok so after he had answered my question with a “yes” it was turn again to get asked or dared to do something. Daniel still seemed a bit timid about everything, which really creeped me out. After all we both were 18 years old. Masturbation as a joking matter came up quite often and one would assume that with 18 even a serious question about such an over all harmless topic should not really throw anyone off. To get him out of being so damn uncomfortable I said “Truth”. He looked up at me and took an eternity to come up with his question. He asked: “Do you often watch porn when you do it?” That really confused me but I answered: “Of course I do. You don't?” There was a forced smile on his lips. “I can't, you know, we are really religious and my parents are very strict. I don't have a TV and I am not allowed to close my bedroom door at home. They also monitor my W-lan and check my mobile.” That revelation really shocked me. I obviously knew that his parents were strict, I only had meet them once and back than they seemed all right, maybe a little uptight. I would never have guessed that they were that bad. The idea of getting controlled in such a way was actually beyond me. My parents certainly hadn't allowed me to do whatever I wanted growing up, but after I was 15/16 the more or less treated me like an adult (in both ways of getting freedom and carrying responsibility.)

“But how do you do it than?” My shock must have shown because Daniel seemed really abashed when he answered. “Well, I ehm, just kind of wait till it is really late and they sleep and than I use my imagination. Or I do it under the shower. That is one of the few places they leave me alone.” That moment I really pitied him. “It is really annoying, they simply want to control all of my life.” That moment really called for a drink and I left to get something from another friend of mine who I assumed still had something, but not before squeezing Daniel's shoulder. It was the best I could think of that moment. I actually managed to get hold of a bottle of something and when I came back Daniel was still sitting in the same spot on his bed, shoulders slumped forward. I sat down next to him and handed him the bottle. While he took a drink I told him about something mundane I had seen along the way just to talk about something different. The conversation slowly started to become more light-hearted and after some time we were both laughing again. At some point he said that he wanted to go on with the truth or dare game. It being his turn to choose he choose dare. And something I had already wanted to try for quite some time came back do my mind: “So you know how in the movies they always do shots out of the bellybutton of an insanely hot girl that than starts to giggle? I dare you to drink a shot from my bellybutton.” He burst into laughter. “You do realise that you don't exactly look like Megan Fox right?” I just laughed. He than went on: “Well I brought the game up again so I have to deal with the consequences.” I lay back lifted my shirt and poured it in and he actually drank it, although a bit clumsy. That was probably one the oddest and looking back strangest moments of my life, but it also was good fun. Nothing really came of it, I just let my shirt back down and we continued playing. Daniel however seemed to loosen up, probably because of the rising level of alcohol. Next up I choose “truth” and he asked: “How often do you normally masturbate a week.” That was the moment when I realised that he really wanted to talk a bit more about this stuff. I was more than happy to keep the conversation going into that direction, so I thought about my answer and tried to answer as honestly as I could: “Well, currently I'd say roughly 4 times a week, when I was younger a lot more. But I also have weeks where it may only be once or days when I do it 3 or 4 times. It really depends on my personal mood and how occupied I am.” He nodded: “Yeah, that is the same for me. Sometimes more sometimes less, although I of course also have other reasons to not do it like I already said.” After a short pause he added: “Ok I am going to take truth as well.” I wasn't sure if I should ask the next question but did it anyway. “Did you ever have sex Daniel? I'd assume with your parents it be tough to bring home a girl.” He nodded again his eyes fixed on the ground. “Yes it is really hard. I am still a virgin.” That I did not find to be to much of a problem at that point I had also only slept with two girls. He however seemed to be rather unhappy with it. Not wanting him to get all sad again I interjected: “Don't worry. It will all happen eventually. I'll take dare this time.” He brightened up and got a mischievous smile on his face. “I dare you to show me your favourite position by dry humping the air.”

Now it was my turn to laugh. I crawled up on the bed getting on my knees in a doggy-style position. On arm stretched out as if I was grabbing a girls hair the other arm smacking the air in front of me as if it was the most beautiful butt I'd ever seen. My hip thrust forward first slow than faster and faster. After what must have been a good minute I even acted out an orgasm moaning and screaming “Yes baby”. I couldn't really stay serious during the entire act. Neither could Daniel. That moment I felt really comfortable. We both had fun and was I was looking forward to the rest of the evening. After our laughter had calmed down a bit, I asked him what it should be next and he answered with “Dare”. Now it was my turn to smile mischievous. “Well”, I opened up: “After you forced me to exhaust myself it'd be only fair if you'd help calm down again. You know I could really use a back massage right now.” He simply shrugged: “Ok sure, why not.” There was however an edge to his voice that made me believe he was not as nonchalant about it as he wanted me to believe. When I started to unbutton my shirt he looked at me with a perplexed gaze: “What are you doing?” I smiled back at him, throwing my shirt over to my bed: “Have you ever heard of someone getting a massage wearing a shirt?” There was a short nervous chuckle: “Ehm, I guess not really.”

“You see, it would be stupid.” I laid down on my stomach while Daniel was still sitting on the edge of the bed. “You going to start now or do I need to fall asleep before you get over yourself and continue with the game YOU wanted to restart?” The words were a joke, but they motivated Daniel to sit up turn around and kneel beside me on the mattress. When he laid his hands on my back I was surprised by how cold they were and abruptly shuddered. Daniel immediately asked me if everything was all right. I told him not to worry and go on. He started out slowly and with little actual pressure, it was more like he was petting me than giving me a massage. However after the first initial soft touches he grew more courageous and started giving me an actual massage. It was, however, mainly a shoulder and not a back massage. When he asked me how it felt I poured that it was nice, but he also should work the muscles a bit lower down. He followed my instructions even though he was very careful not to get anywhere near my lower back or the waistband of my jeans. Still I was only able to suppress my arousal by focusing on my body and the round, kneading movements of his hands rather than on my thoughts what those implied. It may sound weird, but focusing on the relaxation of my muscles is what prevented other parts of me from getting hard right away. After his massage had gone on for a few minutes and me wanting it to continue a bit longer I said “Truth” again. This time Daniel didn't think long. “Have you thought about someone from our school while doing it and if yes who?” I tried to nod than realised that from his position he may not really see it and answered. “Yes I have.” Now I could of course only say names of the girls because telling him the name of a guy, even though it would have been true may come across strange. So because I didn't want to lie I simply said: “For example Laura and Jennifer.” He seemed to be contempt with that answer because he wanted me to ask him another truth question, so I did. “So when I saw you the other night, it looked like you had shaved pretty thoroughly. Did you, well how to say it? Did you actually shave your butt as well?” I wish I could have seen his face, but because of the way we were positioned I couldn't. His answer was a simple: “Yep. Truth or dare?” Nothing more. So I said “Dare”, sitting up and effectively ending his massage. He scratched his head: “Hmm, how about you try to do the splits?” I used to be quite flexible when I was younger and the alcohol told me that surely I still was able to do splits so I jumped up and tried without even answering. I however had to realise that with my jeans on there was no way in hell I would even get close, so I simply took them off and threw them next to my shirt. Now in my wide boxers I was able to get a lot further down, the shorts slipping up the further down I went. But I was not able to get full splits no matter how hard I tried. After a couple of failed attempts I got up and shrugged. Daniel however seemed to be happy with my attempt because he simply said: “Dare”. I looked him up and down blatantly and than suggested: “Why don't you have a little run down the hotel hallway in your underwear? A little exercise would probably help you to get sober again.”

“You just want to get me to take my clothes off”, it was meant to be a joke but he was actually 100% on point. However I of course did not tell him that. “Oh come on. There is nothing there I have not seen yet, remember?” That seemed to convince him because he got up and started pulling his shirt over his head. There it was again. That exquisite stomach, that I could not get out of my head, followed by toned thighs when he pulled down his trousers. I tried not to stare at him but only managed to look somewhere else half the time. Twice he caught me staring and once raised his eyebrow at me. I ignored it. Like me he now was only wearing wide boxers. The imagination of what was under them, the idea of me being able to see MORE once he sat down at the wrong angle already turned me on. We went to the door, he positioned himself in a sprinters crouch in the middle of the hallway. I counted him down from three using hand signs and of he left, sprinting down the hallway in what can only be described as a straight line if one is very generous with the definition of the word 'straight'. He however made it till the end of the hallway, turned around and was back at the door and in the room, before any of the other doors opened.

“Man what a sprint. I thought you were going to hit the wall at the end. You did not exactly look graceful Daniel.” He was still a bit of out breath and didn't bother to answer before sitting down on his bed again. “To be honest I felt a bit unbalanced.” He offered still panting. I slid down next to him, close enough for my shoulder to barely make contact with his. I started to get really nervous. Here we were both in our underwear, loose, drunk and open to talk about stuff. How far would this go? How far would I be able to dare going? I hit him on the knee with my hand in a gesture of friendship and left it there. “Well you made it, fast enough for no one to catch you, that's what matters.” The skin above his knee felt perfectly soft on the surface, freshly shaven even and I wondered if that was what he had been doing in the shower yesterday. However I was still able to fell that right underneath the skin was muscle. Really not surprising, his legs were not exactly big, but they also did not look like there was a lot of fat to be found. I was instantly reminded that he played in a football (soccer) team.

Being so close to him I felt heat starting to swell up inside my body. Something in my boxers twitched nervously, waiting to finally be allowed to tense. “Truth.” He looked at me from the side, than down at my stomach and legs. “Do you also shave like I do?” The question was easy to answer and I was a bit sad that he had 'only' asked something like this. My heard was racing. I asked: “You mean like this?” I used my hand that was already on his leg and caressed it a bit. “Yes I do.” He did not seem to uncomfortable with the movement so I kept going. Slowly but surely my shorts were rising and it felt like I was already half the way to getting an erection. “Dare”, he said. I felt like this was it. All or nothing. Now or never. Sweating I looked into his eyes and than with a smile said: “Strip for me.” My plan was to claim it was just a joke if he understood it wrong and try to limit the damage to a minimum. However he simply blushed and sat there for a moment. Than he got up and positioned himself out of my reach. Facing the wall he made some dance moves but they felt stiff. Than he started playing with the waistband of his boxer letting it sink a bit and than pulling it back up again. He repeated the process a couple of times and each time I could see more of the firm untanned butt that lay underneath the cloth. Finally he dropped the shorts entirely and clutched his hands in front of his junk. This however meant I got a good look of his backside. When he turned around to sit down again he did not dare to look at me. I however couldn't take my eyes of him. At some point he noticed my gaze and we locked eyes.

His head was still fire red with embarrassment, but I assume mine must haven been just as bad. After what felt like an eternity he simply stated. “What are you waiting for? Now is your turn.” The words took some time to register but when they did I got up and started dancing. I felt just as stiff as Daniel had looked. At some point there was a voice in my head that screamed: 'You know what? Fuck this, you can do better than this.' With my new-found motivation I started to loosen up a bit. I turned around and was pleasantly surprised to see that Daniel was following my every move hands still clutched over his manhood. That turned me on even more and I started to really get into it. I looked him in the eyes and started to move towards him. Once I was close enough I laid my hands onto his upper thighs, stretching my back and arms as far forward as possible and slowly slid down towards his knees while righting my back. I was rewarded with goosebumps for both of us. I now started playing the same game he had played with his waistband just unlike him I was facing him. My dick was rock-hard the boxer kept getting caught on it. When I was finally able to slip it past the tip, everything sprung free. I raised my arms behind my back and got closer to him. It was easy to see now that Daniel also had a throbbing erection, his effort to hide it was rather volatile. I did not try to hide anything. With arms raised I approached him, using my legs to push his legs together, than lowering myself to sit on the part of his thigh just above the knee. My skin rubbed against his. Hips constantly moving. I took one of his hands into mine and placed it on my lower back right above my ass. He almost automatically grabbed it. My other hand cupped his cheek and I pulled him in for a kiss. I could feel his heat. When we were face to face I could feel his warm breath. I closed my eyes and opened my mouth anticipating the moment our lips would meet. Than it happened. He tasted sweat. First the kiss was shy and innocent.

Lip on lip, but than it became more demanding. Opening up our tongues became locked in non ending dance. This way we slowly fell back on the mattress. Me laying slightly sight ways and partly on top of him. While we kissed both of our hands started exploring the new terrain. Mine was still moving along the ups and downs of his six-pack when his had already found it's way to my cock. He played with my foreskin pulling it back and forth. His fingers smeared my precum all over my shaft and the soft skin at the tip. Than he started stroking. When I finally arrived at my destination I simply pulled his skin back and started going to work, he was already covered in a large amount of bodily fluid. He started kissing my neck and upper body. I in turn pulled him close towards me, turning him so I could get a firm grab on his perfect ass. Both of our bodies moved in sink. Skin pressing against skin. Wild kisses firing back and forth and the never ending rhythm of moaning matched the stroking going on further down. I was the first one to give in. Under the constant onslaught of flesh and heat I felt an orgasm roll over me like a wave, sweeping me away. I started pumping. Daniel did not slow down one second. Everything exploded out of me. I sprayed all over his lower stomach and cock. Some of the cum ended up on his penis, which was still firmly in my hand. He came shortly after. Shooting an equally impressive load further up to his own chest. For the next 15 minutes we just lay there. Covered in cum, Daniel sufficiently more than me, breathing heavy and radiating heat. We caressed each other, kissing ever now and than. At some point we decided to get up and shower, washing each other from head to toe. That was the end of night number two of our six day holiday.

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Once upon a time in Italy

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