Chris - Trip To Italy

Shortly after graduating from film school, my friend Georgio moved back to Italy because his student visa expired. Many times he told me he wanted me to check out Italy, and that he would tour me around and all that stuff. But since he was going to be stuck back home for a while waiting on paperwork to get back to the US, I decided to take him up on his offer.

I had never traveled outside of the US before, so I was really excited. We planned it all out: a few days in the city of Bari and then a few days at his family's Trulli in the country.

When I arrived, we hit the ground running. I checked into a hotel a few blocks from the condo he was staying at. I would’ve stayed in the condo, but it was small, and his mother lived there too. He introduced me to a friend of his, Paulo. They had known each other since they were small children. It was fun watching them joke around. Paulo was hilarious. Unlike Georgio, Paulo was closer to my height, around 5’9”, he was skinny like me, but he had the longer, thicker Italian hair that kept falling into his model-like face.

I didn’t see Paulo again until the weekend. We went out to a few bars in downtown Bari. Georgio brought a girl with us that he was trying to hook up with. She was a lot of fun, too. The more we drank, the more she directed the conversation to sex. She asked us all about our first times, condom practices, and even if we had tried same-sex sex. I was a bit tipsy, and since she admitted to having had sex with a woman, I admitted having tried sex with a man. I didn’t mention that I had tried it more than once, mainly because Georgio was very surprised by this information, and I figured I’d just leave it alone since up until this moment, he thought I was 100% straight.

We went to two more bars before I noticed Georgio and his lady were getting touchy with each other. So I decided to bounce to let him seal the deal.

“Man, I’m wiped, I’m going to head back to the hotel,” I told them.

“Oh, ok, I will walk you back,” Geo said, being a good friend.

“Nah, you stay. Enjoy your night,” I said, giving him a look that he picked up on.

“I’ll walk you back, I have an early day anyway,” Paulo insisted.

He and I walked the ten minutes back to my hotel. I told him I wasn’t really tired, just wanted to give Geo the chance to get laid. Paulo laughed and told me he didn’t have an early day tomorrow and was doing the same thing.

“You want to chill in the pool at my hotel?” I asked, hoping to keep the party going.

“Fuck yeah,” he said.

We ducked into a sketchy corner store where Paulo seemed to know the owner. I got some whiskey, and Paulo disappeared while I was paying. He reappeared outside, smoking a cigarette. When we got into my hotel room, he told me he had purchased some weed for us from the guy at the store.

“Awesome, let me change into my swimsuit, and we can smoke by the pool, it’s a rooftop pool,” I told him. “Do you need to borrow a suit?” I asked.

“No, I’ll swim in these,” he said, pulling the waistband of his underwear out of his shorts and grinning.

“Cool,” I said, grabbing my swim trunks and heading into the bathroom to change.

The pool was empty and glowing on the roof. It must have been 100 degrees out even in the late evening, so I was ready to hop in. I grabbed us some towels and turned around to see Paulo pulling off his shirt, showing his cut abs and nicely defined shoulders. As I was walking up to him, he dropped his shorts, revealing a pair of bright green sport briefs from a brand I don’t recognize.

I handed him a towel, and he set it up on one of the lounge chairs. Then he sat down and started to roll a joint. I tried not to stare at his package, but I was tipsy and had not had sex with a guy in well over a year. Not to mention his briefs did little to hide the size and shape of his dick which turned me on even more. My hormones started to get the better of me, so I dove into the pool to prevent a situation where I was hard and staring at this hot Italian guy.

“Oh wow, this water is bath-warm,” I said, pushing my wet hair back.

Paulo sat at the pool's edge, putting his legs in the water, and lit the joint. He took a long drag and then held it out for me to take. I slowly moved to the edge, flicking my hands to try to dry them before taking the joint. When I got to him, I tilted my head and took a drag while he held it for me.

Paulo just smiled at me, then took a hit off the joint. He slipped into the pool slowly, keeping the joint dry, and brought it back to my lips so I could get some more. We passed it back and forth a few times, him holding it and me sucking it from his hands. It was the most erotic moment I had with a guy in a long time. I could feel myself getting hard. I quickly took my last long hit and then started to swim away so he wouldn’t see my hard dick.

Paulo finished smoking and then swam around with me for a few minutes. Just casual swimming, back and forth down the length of the pool. I watched as he floated on top of the water on his back. His face, chest, feet, and package were the only parts of him above the waterline. My eyes zeroed in on his package. The wet green fabric clung to his cock and balls, the skin darkening the fabric making it almost translucent, or maybe my horny brain was filling in the details.

“Do you have the whiskey?” he asked me, still floating.

“Oh yeah, it’s with my towel,” I pointed.

He turned upright, feet on the ground, nodded, and with just his arms, he lifted himself out of the pool in slow motion. The water cascading down his sexy back, his soaked underwear clinging to his skin like they were painted on. He walked three steps to my towel, bent over, pulled out the whiskey, and opened the bottle. I watched as he took a swig and swallowed it like it was water.

“It’s good,” he said, walking towards me to hand me the bottle. His dick was clearly visible through his wet briefs now that he was out of the water. I couldn't help but watch it swinging as he walked. He sat on the edge of the pool again, legs in the water, and held the bottle out for me.

I swam over, took the bottle, and took a swig. Handing it back to him my eyes fixated on how big his dick looked through his wet underwear. It might have been in my head, but I’m nearly certain he spread his legs knowing I was looking.

Unsure of what the protocol was here, I just decided not to make a move. I dove under the water and swam until I couldn’t hold my breath anymore. As I surfaced, I heard him dive in. I wiped the water from my face and felt him pull me under the water. We wrestled a little, and I eventually got away laughing. I made my way to the shallow end and sat on one of the steps, the water still above my legs and kissing my balls with every splash.

Paulo swam over to me, sat beside me, and spread his legs a little again. I missed when he grabbed it, but he produced the bottle of whiskey and took another swig, and again passed it to me.

“I always wondered if Geo was bisexual,” Paulo said, out of nowhere.

I laughed, nearly spitting out the whiskey, “I don’t think he is.”

“You two never hooked up?” he asked.

“Nah, why did you?” I asked.

Paulo laughed, “Not exactly,” he said, taking another swig.

I felt my dick twitch, “what does that mean,” I pressed with a grin.

He laughed again, “Oh... no, never mind. " He tried to pull the pin and not throw the grenade.

“Oh no, you can’t start that thought and not finish it,” I laughed.

He got a little shy, taking a long, dramatic pause before he started again. “Well, when we were younger, before we had girlfriends, we used to do this thing…” he trailed off, probably trying to find the English words for his story.

I didn’t say anything, I didn’t want to scare him out of going down this detour of memory lane.

“You know, when we were horny and discovering ourselves,” he continued.

“What, like jerk off together?” I asked.

“No, no, we did a thing like…” he was starting to struggle to find the English words to finish his thought and started to gesture what looked like he was holding the hips of his friend and fucking him from behind.

I laughed, “You had sex?”

“No, no, we had our clothes on,” he told me with a laugh.

“So, you just dry-humped?” I asked, confused.

That didn’t seem to translate for him; he looked at me with a confused grin.

“No, come here,” he said, grabbing my arm and trying to pull me up while he stayed seated.

I laughed and stood out of the water, my wet bulge clearly visible, but at this point, I was not giving a fuck and just having fun. Standing with my slightly bulging shorts in his face, he told me, “Turn.” So I turned to show him my ass. He grabbed my leg and had me step over him, and I realized he wanted me to straddle him.

I laughed, “Oh, I think I get it,” and moved down a step so I could lower my ass down onto his lap. As soon as my ass landed, I heard him let out a small gasp. I felt the semi-soft length of his dick sausaged between my cheeks and our clothes, involuntarily I clenched my cheeks which pulled another soft moan out of him. In a softer tone, I asked, “Like this?”

He put his hands on my hips and spread his legs a little more so his hardening bulge pressed more into me. He whispered, “Si, and then we rock.”

I started to flex my ass around his obviously bigger dick, slowly rocking my hips, feeling my heart beating so fast and hard, I let out a soft hum of pleasure.

“Yes, like that,” he said in a breathy voice, grinding into me.

It felt good; the heat coming off his lap was making my blood boil. My dick was rock hard and I could feel he was too. He started tugging on my trunks, so I quickly stood and dropped them to my ankles, then right back down onto his now hard bulge. He kept grinding, feeling my ass cheeks with his hands and flexing his dick with every thrust.

I felt his hands pulling down the front of his wet briefs and his cock sprang free, audibly smacking my bare ass. We resumed grinding, him pulling me harder into his now fully hard 8 in uncut cock with every rock of his hips.

He let out a soft moan, and then we heard the door open and close around the corner. I quickly slipped into the pool, getting waist-deep in the water, resting my folded arms on the edge of the pool, trying to look like I was just chillen and not hiding my nude erection. Paulo quickly swam to the deep end and held himself up from the edge as we watched a hotel worker restock the towels.

The hotel worker didn’t say anything or even look at us, and went back inside. As soon as the door closed, I felt Paulo’s body heat behind me again. Standing behind me, he put his hands around my waist and pressed his hard dick between my cheeks again. Now at an angle where he poked my hole with the head of his dick. I let out another moan.

He held my swim trunks out in front of me with one hand and used the other to wrap around my waist, pulling me tight into his dick.

“Do you want these?” he asked, giving me the option to get dressed.

I said nothing as he dropped them on the edge of the pool in front of me. Paulo started grinding so hard he was slightly lifting me out of the water with each upthrust. With each grind, we shifted more and more into the shallow end until my ass was completely out of the water. I let my head fall back so I was cheek to cheek with him, his heavy breathing right into my ear. I let out a soft moan, meeting his thrusts.

I reached around, pulling his firm ass into me, “did you guys ever do it like this?” I asked.

“Once or twice,” he laughed, his uncut cock sandwiched between my bare ass cheeks, sliding across my hole so gently.

“Mmm,” he moaned, feeling skin against skin.

“Oh man,” I whispered, bringing my arm up to his neck, pulling his head even more into mine, hoping he would take this a step further.

He kept thrusting; I kept spreading my legs more to give him more access. His precum pooling inside the foreskin of his dick, and then it smears on my hole with each pass. I was so horny I wanted more. I didn’t want to say it, though, in case this was as much as he wanted. I just moaned every time his head rubbed against my hole, hinting that he was hitting the spot.

Paulo leaned away from me and rubbed his dick up and down my crack, smearing more precum on my hole, wiggling his slick head right on the pucker, both of us let out a heavy breath. He lined up the head with my hole and started to push a little; I jumped forward when the head popped in.

“Oh, shit dude, spit on it or something,” I tried to laugh through the sting.

“Si, si,” he said, still holding my hips.

I heard him spit, then rub it into my hole. He quickly did it again, and again until he was satisfied there was enough.

“Can I?” he asked while already pushing the head into my tight hole.

“Gentle,” I groaned, trying to relax, feeling him stretch my hole with his Italian sausage.

“Ah, si, si,” he said, slowly pushing in another inch and letting out a low, breathy moan.

“Oh shit,” I whispered, feeling him start to stretch me out.

I felt him bottom out inside me, and he bit my shoulder. Paulo just froze there, his heart beating so hard I could feel it pulsing in his cock.

“You like?” I asked.

“Oh wow,” he mumbled, “so good.”

I felt him make a small thrust; I let out a moan. He only pulled out an inch and rocked it back in deep.

“So tight,” he said and held me tighter, his chest to my back, sucking on my neck.

Out an inch and then back in, holding it there.

“Mmm,” he moaned, making me moan.

I started to jerk myself off, clenching my ass around his massive dick. I tried to rock my ass on his cock but he had such a firm grip on my chest and waist I could only get the small, slow thrusts he wanted to give me.

“Fuck that feels good,” I told him, trying to keep my voice down. I was quickly feeling myself get close, beating my dick like I just learned how to masturbate.

“Si, così buono,” his voice low, vibrating through his chest into my back.

I clenched my ass some more, stretching my legs getting a little more dick from him. My toes stretched on the floor of the pool as I flexed my ass muscles around his cock.

“Fuck I’m close,” I told him.

“Me too,” he said, “il tuo culo si sente così bene, ho intenzione di venire dentro di te,” and rocked his swelling dick deep into me. He let out a soft moan, I felt his dick pulsing as he quietly moaned.

It felt so good, it sent me over the edge, “Oh fuck I’m cumming,” I said and started to shoot my load into the pool. I clenched tight on his cock, he held me tight.

He moaned in my ear, both of us catching our breath. He held me tight and slowly started to pull all 8 inches out of my ass.

“Do you want to cum?” I asked, turning to face him.

He smiled, “Oh," a nervouse chuckle, "I did cum."

I smiled, “Inside?”

“Of course,” he said as if no other option existed. He smiled as he tucked his semi-flaccid dick back into his soaked briefs.

I let out a laugh and pulled him in, giving him a sensual kiss. He recoiled a little at first, but then got into it. We started to make out right there in the pool, even hotter than when he was dry humping me.

I put my trunks back on, and we toweled off. We quietly walked back in and called it a night.