Holidays in Italy. If my parents knew the trouble I was about to get into they'd freak out. I ditched my parents last night and wandered around the hot spots. I had a map showing all the hot clubs to hit.

I found a place where the waiters spoke English quite well. It catered to the tourist crowd. I decided this was where I was going to hang out for the night, not a gay bar, just a party place in general. In the first 30 minutes 3 good looking guys hit on me. I was pretty sure 2 were male prostitutes though, the other guys weren't quite my type but they bought me a couple drinks. I always make sure to drink bottled beverages and never let them out of my sight.

Mom and dad had an idea I was looking to hookup, Likely not a man though, ;) One guy was definitely checking me out. I checked out his friends and observed what they were doing. I was pretty sure they were tourists and just out to party and find some sex for the night. I hadn't had sex with a guy yet, just in my mind. When the family travels it's a golden opportunity to find someone, I just keep striking out. The guy looking at me was a bit older than me and looked like George Clooney in his younger days. I caught him looking and next thing I know he's over talking to me.

His name was Angelo, he was Italian but born in USA. He was over tracking his roots. Super good looking guy and single, never been married. He was 8 years older than me. He was feeling me out but for sure he was in the same boat as me, maybe talking a walk on the wild side, or thinking about it. As we talked he told me he'd given up on women. He wasn't getting what he needed from females in the bedroom. He was blunt about it. He said, "My needs aren't being satisfied." I left the nagging question alone for a few minutes then finally asked what need isn't being met" He hummed and hawed. He finally said, "Bum play." He likes bum play. We finished our drinks and went for a walk. The weather was great and we wandered around and hit a couple other places. I was getting a little drunk. We talked about sex and first time with a man would be a rush. I said, "All this talk about first time with a man is making me horny!!" lol. He nodded, "yup. me too"

Angelo had a hotel room a block from where I was staying. We took a cab back the that area. Once we were in the cab he started kissing me and feeling my chest as if I had tits. A force of habit I'm guessing. My cock was tight in my pants. He had me pretty much pinned as he felt me up and kissed me. Definitely the best kisser I ever met. My cock was so hard it felt like it was going to rip my underwear. I couldn't wait to get him alone.

When we got to his room he led me to the bed. He undressed me piece by piece. Every article of clothing he kissed it off of me almost. When he pulled my pants off I was as naked as I've ever been in front of anyone. He was sitting on the bed and he pulled me towards him. He kissed my cock from the outside of my underwear. He rubbed his cheek against it and it swelled. He kind of sucked my cock through the underwear. Finally he pulled them down and my cock sprang out to his waiting lips. He kissed it like baby kisses up and down the shaft. He took me in his mouth as I stood there and reached around, stuck his finger up my bum and pulled me towards him. He steered me around using the finger up my bum. I was running my fingers through his hair and kissed his forehead. He laid me on the bed and I watched as he undressed for me. It was more of a striptease. When he undressed it was sexy, when he finally dropped his pants he wasn't wearing underwear. He had a juicy 8" cock with a nice head. Perfectly shaped. I pictured my lips on it. I knew I'd met my first time with a man and boy he was hung.

Yup, my ass is seconds away from getting fucked by this guy. I told him I had lube and condoms in my pocket in hopes of this happening. He grabbed the lube and smeared it on the hole. I rolled the condom on him as he laid beside me kissing me, bumping his cock against my hole. His hands were constantly roving my chest massaging and rubbing me. Tweaking my nipples and making tender love talk in my ear. He had me in a great position that he could enter me and jerk me as he fucked me. He continued to kiss me as he was gently pushing his cock into me. The anticipation of feeling it in me was making me insane. I couldn't wait for the total euphoric feeling as a man fucked me. Everything I had been waiting for was about to happen and, oh dear lord!!! He was inside me. No pain. Just a slight resistance before he was all the way in,

I couldn't talk, my balls suddenly ached so much. They felt like they'd been squeezed in a vice. It felt like I had blue balls. He was whispering to me in a soft voice. Thank god he was nowhere near cumming (I don't think) as I was in heaven as he fucked my ass. It was my first time, the sensations coursing through my body was amazing. He stroked my cock for me as he make beautiful steady thrusts. My cream was dribbling out the whole time. It flowed as intense pleasure consumed my body. Wave after wave of head to toe rushes flowed over me. I was quietly uttering "oh oh oh" over and over. He kept telling me he loved me. That makes you feel really good as you're being fucked for the first time. He kept telling me how beautiful I was and I replied that it was him that was beautiful. He really was drop dead gorgeous.

He lasted forever, I wasn't complaining at all! He was close to cumming. He chose to pull out and remove his condom and I was mesmerized watching as his cum shot on my belly and nipples and almost my chin. It was a cum bath. It made my little orgasm look pretty small. He cuddled up to me like a real lover. He rolled my cum drenched body towards him and kissed me deeply as he flattered me over and over. Hearing all the praise made me melt into his arms. I really liked Angelo. I couldn't have asked for a better first time lover. He spooned into me kissing my neck and my shoulder. He tickled my nippled with his tongue licking up his pearly man juice then invited me to do him. I asked if he really wanted that. He smiled, "I like it the way we just did it." I agreed. Why wreck a good thing?

Thank god neither of us was in a real rush to go anywhere or had other plans. It was relatively early and he ordered food and wine up to the room. Angelo wasn't shy, when the guy rolled the cart in he answered the door naked and the room service guy saw me under the covers. He just smiled as he left. "Enjoy the rest of your evening" We had some snacks and wine, I could see Angelo begin to get hard. I laid on my back and he spread me open as he held my legs back, he slid in pretty easy this time. I was relaxed, that helped. The second time was more emotional, more intense. The nervous aspect was gone and the sheer joy and feelings of having a gorgeous man fucking me made me grin. I could watch the pleasure and pain look on his face as his orgasm built and subsided over and over till he finally came in me.

Over the course of the next couple hours we repeated this and he sucked my cock allowing me to flood his mouth with my virgin gay seed. Like a good lover he swallowed my cum knowing I would like that. Eventually as he spooned me we drifted off. I woke up in the middle of the nice and after 30 minutes of passionate kissing as he masturbated me I told him I had to sneak back into my room. And hope that my parents didn't know exactly how late I was out. Not that it really mattered. The less they know the better. Of course Angelo and I were in sync to get together as much as we could.

He was here for roughly the same amount of time we were and luckily I'd met him early in the trip. We had almost two weeks together. Everyday we managed to find a time to spend an hour then our evenings were a few drinks at a cafe then race back to his room. It was hard to keep our hands off of each other. The sex was amazing and I really couldn't see fucking a woman now. I can get everything I want from a man, plus a man knows exactly what a man likes. On top of that I told him my secrets that pleasured me too. The scent of his cologne instead of perfume as we made love was better. A mans voice sweet talking me and of course a great cock in my ass made for the ultimate lover. My mom mentioned something to me one day, "You sure seem happy. Italy agrees with you." Yup mom, you have no idea how much I like Italy.

In all honesty I saw very little of Italy. I saw the face of a beautiful man fucking me a lot though. :)

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