Once upon a time in Italy by Enox

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.”