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 planed it all out, a few days in the city of Bari and then a few days at his family Trullo 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 incredibly funny. Unlike Georgio, Paulo was closer to my height around 5’9”, he was skinny like me but he had the longer thick 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 this girl with us that he was trying to hook up with. She was a lot of fun. 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 to trying sex with a man. I didn’t mention that I had tried it more than once, mostly because Georgio was very surprised by this information and I figured I’d just leave it alone.

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 gave 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 purchased us some weed 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 pulled up the waistband of his underwear out of his shorts and laughed.

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

On the roof, the pool was empty and glowing. It must have been 100 degrees out 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. 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 edge of the pool, 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, flicked my hands to try and dry them before taking the joint. When I got to him, I just 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 the joint and then swam around with me for a few minutes. Just casual swimming, then 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 leaving very little to the imagination.

“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, lifted himself out of the pool in slow motion. The water cascading down his sexy back, his soaked briefs clinging to his skin like they were painted on. He walked the three steps to my towel and 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 and started to walk towards me to hand me the bottle. His dick was visible through his wet briefs, 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 to not 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 next to me, and again spread his legs a little. I’m not sure 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.

Nearly spitting out the whiskey, I laughed, “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 and took 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.

I didn’t say anything, I didn’t want to scare him out of going down this 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 in his lap 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 moan.

“Yes, like that,” he said softly, 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 thrust.

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. No sooner did the door close and 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 lifting me out of the water with each upthrust. With each thrust, 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, thrusting 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.

He kept thrusting, I kept spreading my legs more to give him more access. His precum pooling inside the head 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 head right on the ring, both of us let out a soft moan. 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 did it again, and again until he was satisfied there was enough.

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

“Gentle,” I said, 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 groan.

“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 said, “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. But fuck it felt good, I was quickly feeling myself get close, beating my dick like I just learned how to masturbate.

“Fuck that feels good,” I told him.

“Si, così buono,” his voice low.

I clenched my ass some more, stretching my legs getting a little more dick from him. My toes stretching on the floor of the pool.

“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 I did cum,” he laughed.

I smiled, “inside?”

“Of course,” he said as if there was any other option. As he tucked his semi-flaccid dick back into his soaked briefs.

I let out a laugh and pulled him in, gave 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, quietly walking back in and calling it a night.