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You are here: Home / Adult sex stories / Once upon a time in Italy by Enox

Once upon a time in Italy by Enox

by Enox January 16, 2022 Leave a Comment

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.

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