Alessandro, Chapter 3

Alessandro

When I woke up it was Wednesday, my third day in Milan. I had dreamt about Alessandro, so I woke up with major morning wood. I pushed it down as if that would help. I stretched out and got myself out of bed. Today I was going on a trip to where Giulia’s clothing is manufactured. I mainly had to look out for working conditions and listen to a presentation about carbon footprints. It helped that I didn’t need to impress today, I was the one who needed to be impressed.

I made myself some cereal and leaned back against the counter as I ate it. My dick was pointing ahead, still rock hard, as I looked around the apartment. It was starting to feel like home. Milan was a great city. I didn’t feel like going back to New York yet, not before some closure with Alessandro. I still had two and days for that to happen.

The day ended up going great. Everything the representatives for Giulia’s had promised about their manufacturing process was true. Conditions seemed to be fine. Everything seemed to be a go for the contract. Daniel had asked I’d scan the hardcopy of the contract they had given me per e-mail to the New York office so the legal team could look it over. So after the visit to the factory, Alessandro drove both me and Mahmood back to Giulia’s office. It was about a 90 minute drive from Milan, so it was the afternoon once we arrived.

When we got there, Mahmood said goodbye to me and had said he hoped for a good final meeting tomorrow morning. Alessandro brought me to the copy corner where he showed me how the scanner worked. It was quite a number of pages, so it took a while to go through.
“So… Milano visit almost over”, Alessandro said.
“Yeah”, I replied.
He looked happy, relaxed. We looked at each other.
“I had a great time, you did very well looking after me”, I said, breaking the silence.
“Good. Is my job”, he said, looking away.

Things had continued to be awkward between us, only because of our relentless chemistry that wasn’t being acted on. Every day Alessandro had looked like an absolute hunk of a man, in his Giulia’s men’s wear. He really sold the designs to me, even though he was far too buff to be a traditional runway model. I had also started to enjoy his personality, even though it did take a while to show itself.

Again, Alessandro dropped me off at my apartment in the late afternoon. And again, he got out of the car to give me a hug. It was a longer hug this time. I smelled his smell and felt his muscular arms around me and I just wanted it to last. I pulled my head back and we just looked at each other, faces inches apart, bodies still entwined. Every fiber in my being wanted to kiss him.
“Tomorrow”, he whispered.

He let go. He squeezed my bicep and walked back to the driver seat, leaving me standing on the sidewalk. He winked at me from the car and drove off. I was left with feelings of desire and anticipation. When the car was out of my sight, I went into the building.

I called Daniel and talked him through what I had seen today. The legal team was still going over the contract to see if everything was the same. I would get the final go-ahead via text the next morning because of time difference. So far though, everything was looking good.

I had made myself some food in the apartment and went for an evening stroll through the city. I passed the gelateria Alessandro had taken me to when it had started to rain on my first day. I ordered a large ice cream and thoroughly enjoyed it as I walked back. I had a hard time falling asleep thinking about everything that could happen the next day.

As was to be expected, in the morning I got the green light to sign all the papers. Alessandro picked me up again and gave me a firm hug. I felt his bulge press against me just above my own. He was looking mighty fine in just a crisp white shirt and light blue slacks. He drove me to the office and I was feeling very calm. In the conference room, it was just me, Mahmood and Francesca. After Alessandro had gotten us all coffee, and I suspected all three of us looked at his butt as he walked away, he closed the door behind him and we went through the contract one more time.

I signed the contract and there was champagne. Mahmood wanted to know if I was going to explore more of Milan before my flight tomorrow and I replied that I surely would. I told him I had more than 24 hours before I needed to be at the airport. He suggested I had Alessandro show me around more of the city if I liked.
“Oh, that would be great”, I said, thanking him.
“And I would like you to enjoy lunch on behalf of Giulia’s. Our treat.”
“That is so kind, thanks a lot.”

I said goodbye to Mahmood, thanking him for everything these past few days. I had felt so welcome and my stay had been amazing. I wasn’t sure if personal drivers and lengthy lunches with alcohol always happened on trips like this, and were always paid for by the company in question, but just in case this was a rare occasion, I made sure to thank him.

Within an hour I stood back outside with Alessandro, feeling like I had just done something big for the first time in my career. As I was driven back to the apartment, I texted Daniel that everything was over and done with. I put my phone away and told Alessandro that Mahmood had OK’d for us to have lunch and spend the day around Milan together.

“I no show you the city. Or, maybe later.”
“Wha- why?”
He looked away from the road and right at me.
“You fuck me, yes?”
I smiled so widely, my cheeks hurt.

When he parked the car, we basically ran inside and stepped into the elevator. We started making out, this time I noticed his moaning to be more high-pitched and desperate. We had been waiting for days for this to happen again, and only now I realized how much he had felt the same. I was aware of when the doors opened and broke the kiss. The exact same lady stood by the 6th floor, waiting to get in.
“Signora”, I said, nodding, as I took Alessandro’s hand and walked past her to the apartment.

Clothes started flying off the second we got to the apartment. We ripped open each other’s shirts and pulled down our own pants. Both of our underwear were tenting with boners. Alessandro didn’t miss a beat and went down to his knees to take my cock out. His blowjob immediately got me to thrust my dick in his face. Practically choking on my cock, all he wanted was more as he held on to my ass and pushed me back into his mouth further and further. Just as I was about to cum, Alessandro’s gag reflex made him pull back.

Alessandro wanted back at my cock, but I felt like now it was finally going to be my turn. I put my hand on his shoulder and pushed him back. I pulled him up so he could stand. I pushed him to the bed. I pulled down the front of his briefs, which were again a very luxurious-looking Emporio Armani pair, and his hard cock popped right out. Uncircumcised, 6 inches hard and thick, and beautifully curved to his right. It looked like a very juicy cock. I went down on my knees and finally reciprocated the Italian blowjob.

I took his briefs all the way off, and pushed him down so he would sit on the bed. He leaned back and moaned as he received my blowjob. Immediately I saw his beautiful hole peek out at me. I licked his balls and gradually found my way down as Alessandro continued to moan. I licked his hole shortly, which made him gasp. I knew what he wanted.

I pulled one leg over the other so he would flip around. It was the first time I saw his round, smooth bubble butt uncovered. With two hands I massaged his large cheeks, really taking in these two handfuls of ass. I pulled them apart and in between such hairless cheeks was a slightly hairy crack. I licked him all over. His moans and gasps got more and more frequent. He also started saying some words in Italian that I didn’t understand, apart from “Si… si…”.

I was more than ready to fuck his beautiful ass. He laid on his back and spread his legs apart for me. I put on some protection and entered him slowly. His expression changed to a combination of worry and arousal.
“Aaahh… si…. Si…. Scopa mi…”
Once I felt his hole get used to my cock I started fucking him faster and faster. He moaned and looked at me with that familiar look of pain and pleasure. His cock was hard but remained in its foreskin as it flopped back and forth on his belly. I cupped the hairless globes of his ass as I fucked him relentlessly. The built-up tension had gotten to me and now everything was coming out.

I took his left leg and threw it over my shoulder so I could fuck him deeper. His moans got so loud I was confident the neighbors could hear us.
“Si! Is the spot, si!”
Alessandro now started jerking himself off with a speed that told me he was about to cum. His orgasm face was so hot, as he looked and sounded almost surprised as the cum flew across his stomach, slowly seeping into the crevices between his abs. Seeing this, I also had to cum. I pulled out and took the condom off. My cum flew across the room, managing to hit Alessandro’s chest and chin.

We looked at each other as we caught our breath and laughed. Alessandro picked some of my cum off his chest and licked it off his finger.
“Was very good”, he said.
“For me too”, I replied.

I let my body fall on top of his as we cuddled for a while, our cum in between our bodies.
“I am so happy”, he sighed.
I looked at him and he did look the happiest I’d seen him. I kissed him.

We showered together and I got to soap down his big body. I took my time and he seemed to really enjoy it. Then we got dressed to go somewhere for lunch. Alessandro showed me his white briefs and how they had gotten soaked with precum throughout the morning. I smelled them and smiled. He decided to go commando, which drove me crazy as we went outside. I had to slap his ass every time it came into my view and we walked hand in hand through some of Alessandro’s favorite spots in the city. I felt like I was on a romantic trip with my lover.

We sat down for lunch somewhere and Alessandro confirmed Mahmood was paying as he showed me the company credit card. The lunch was flirty, romantic and kind of sexy.
“I love Ben serious face”, he told me. “When you work, you get… frown? In your face. Is so sexy.”
Alessandro put his finger on my forehead. I laughed.
“I love your big ass in the tight pants you wear.”
That made him laugh.
“Yes, you like? Is all Giulia pants.”
“I know. But it’s your ass.”
He thought that was really funny.
“Is just a big ass, is not easy to have. I break pants and I make things fall off the table.”
That, in turn, made me laugh.

“Hey, can I ask you something?”
“Yes, of course.”
“I saw Mahmood, he… he squeezed your ass as well.”
Alessandro’s smile disappeared. He looked down at the table.
“Yes. Is true.”
“Is that why you didn’t want me to tell him? Are you a couple?”
“No… Well… No. No more.”
I saw the doubt in his face. He was looking for the right words and I gave him time to find them.

“I was personal trainer but I was 35. I want to be something else. Mahmood was in gym a lot, and flirting with me. I train him sometimes. This is maybe 4 years ago.”
Alessandro was looking very serious as he told the story. I realized this made him 39, which was older than I expected.
“We talk sometimes. He offer me job as security in office. Giulia’s. I… very… thankful. I have boyfriend at the time, Maurizio. I love him then a lot. When I start new job, Mahmood think I have sex with him. I say no at first, but I like him. He help me and he very nice penis, I saw in shower of gym. Not as nice as you, of course.”
He giggled and smiled at me, I smile back.
“So, I kiss Mahmood a little sometimes in the office, but I… feel bad. I love Maurizio also. This is like 3 years. I no want more and then Mahmood offer me assistant job. I tell Maurizio everything and he angry and… leave me. I very sad so call Mahmood. He come over and fuck me. Was nice. I love him too. But he no love me, he only fuck me sometimes. So sex is good, but we not a couple.”

I was very surprised to hear all of this. Mahmood had been using him.
“I don’t think it’s very nice of Mahmood to give you a job and expect sexual favors”, I said.
“I know. Is not. And I was wrong to do.”
“But he is wrong especially.”
Alessandro nodded.
“If Mahmood find out between us, I not know what happen. If you find out about Mahmood, I not know what happen. Deal come first.”

Now I understood why Alessandro had acted the way he had. We had just finished our lunch and the waitress picked up our plates.
“Are you OK with this job now?”
He shook his head.
“I want something else again, but… how?”
“You can apply for a new job?”
He shrugged.
“I don’t know. I like to be assistant and I like fashion. What if Mahmood won’t…”
He was looking for the words, so I guessed.
“Give you a recommendation?”
“Yeah.”

I had an idea. I took out my phone.
“Hold on a second…”
Alessandro looked very confused.
“Hey Adele, it’s me calling you from Milan…”
“Why so early… Wait, what? Milan? How come you didn’t tell me about this last weekend?”
She made me laugh.
“It was a pretty sudden thing. Anyway, I was wondering. Do you have any jobs open for an assistant?”
Alessandro’s face lit up.
“I can ask?”, Adele replied.
I explained myself to her. She wanted to hear everything about my trip as soon as I got back and promised to let me know about any assistant jobs she saw.

Once I ended the phone call, Alessandro immediately piped up.
“Look. I love to go to New York. But if you give me new job and you fucking me, is going to be same thing.”
“I promise, you won’t owe me anything. We will be at different places of work and if we don’t work out, you can keep the job and you won’t see me anymore.”
“Promise?”
“Promise.”

After lunch, Alessandro walked around the city with me and it felt great. I let my hand rest on his ass, knowing it was only the fabric of the pants separating me from his smooth, olive skin. Milan seemed pretty open minded when it came to gay public displays of affection. Though when I heard someone yell something in Italian, I asked Alessandro what he had said.
“Is nothing. He stupid.”
I smiled. I kept my hand where it was.

Our sexual chemistry was off the charts, but I felt like we were bonding on another level as well. That said, when we got back to the apartment in the evening I fucked him again, this time doggy style. Seeing his beautiful ass right in front of me as I fucked caused me to not last very long.

We had fallen asleep spooning each other. When I woke up in the middle of the night finding his ass pressed against my hips, I immediately got hard again. This woke up Alessandro, and before I knew it, he was riding my dick like an absolute champion, with his rock hard dick bouncing up and down in my face, moaning. The neighbor knocked on the wall, presumably wanting us to keep quiet, but we pretended not to hear. Alessandro shot his load on my chest while I was still inside of him.

In the morning, I felt like the luckiest man alive waking up next to him. We cuddled and had sex one last time before I had to pack. He drove me someplace where we had breakfast and coffee. He drove me to the airport and I could tell he was very sad to see me go. He wiped away a tear, which made me tear up a little as well.
“Very happy that we meet, but now I miss you.”
“I will miss you too. But who knows, we might see each other sooner than you think. Hang in there.”

We kissed, right there in the airport departures hall. It was like a scene from a movie, only it was real. I gave him one last squeeze on the butt and said goodbye.

It was great to be home, but I did feel like I left a piece of me behind. When I got into the office on Monday, Daniel arrived on crutches. I couldn’t help but laugh at how much of a workaholic he was. The very first thing he did was ask me to come into his office. I was offered a raise and the promise of more responsibilities.

That week, I met with Adele at our favorite restaurant so I could tell her everything. She was impressed with how I had handled myself and thought it was justified that I was being rewarded for it, finally. When I told her everything about Alessandro, she took it very seriously and said, “OK, we got to get that man out of there. There were no openings in my office, but we both have connections, so… We got to find something!”

And that is how Adele and I sat across from each other in a crowded restaurant, each on our phones, sending out texts and e-mails to every contact we had, just to get Alessandro here. I had complete faith that it was going to work out just fine. I sent Alessandro a picture of Adele across from me, busy on her phone.
“Thank her soooo much”, he said, followed by heart-emojis.
I smiled. I sent heart-emojis back.


THE END

Comments

  1. The emotional - not to say sexual tension - in this story is intense. Wow.

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