Sealing the Deal

My dad's business was an interesting affair, I'll say that much. It was less like the businesses you might be used to. Our business was very community-oriented, family-based, and - yes, I'll admit it - sometimes maybe a bit shady. We grew up in a small neighborhood in one of the less fancy parts of the city and it had its own rules - most of which were decided by my dad and his associates. A lot of people probably imagine something awful when they hear the word "gangster", but my dad has always been the nicest person I've ever known - not just to me or my brother, but also to his customers and business partners. It's not the guns blazing scenes you see in movies - it's mostly deals being made behind closed doors.

Ever since my brother Peter and I were little, our dad always taught us the importance of our business and how it is inseparable from our family. My brother has always been very ambitious. He wanted to be the one who would run our dad's little empire one day, so he took every possible opportunity to learn from him and impress him. But me? To be honest, I was never so much into any of that stuff. I was actually glad that my brother was so interested in taking over because it took a lot of responsibility off of me and I was free to do whatever I wanted. Like my hobbies, my school... or exploring my sexuality.

That's right, ever since puberty, I knew I was more into boys than girls. I tried hiding it away from my dad for as long as possible because I honestly didn't know how he would react to that stuff. But since I was never really that good at keeping it a secret, he eventually caught me with one of my classmates one day after school. I invited a friend to come to my house to "study".

I still remember that day, because of how strange the whole thing was. It was my final year of high school. I was nineteen, and so was my friend. My dad walked into my room right at the moment when both of us were shirtless, with his tongue deep inside my mouth. Once my friend saw my dad in the doorway, he freaked out, jumping out of the bed and backing himself in a corner of my room. Everybody knew that my dad was "the boss" of this part of town and the poor guy thought that the big man was going to kill him for messing around with his son. And while I knew it wouldn't get that bad, to be perfectly honest, I kind of expected him to blow up too - he rarely ever did, but I was sure this was about to push him over the edge.

Instead, my dad did something completely different. Slowly, he walked up to my classmate - who was standing there, half-naked and scared shitless - put a hand on his shoulder, and calmly told him to put his shirt back on and leave the house. He didn't have to repeat himself - my friend basically bolted, not even bothering to put the shirt back on, he just grabbed it and ran. Then, my dad turned to me, still laying on the bed. He sat on the side of the bed and - to my amazement - we had a very long and understanding talk about my sexuality.

He told me that it was okay for me to be curious and that he was okay with me being gay. But, he also told me not to spread myself too thin, whatever that meant... He told me that as his son, I shouldn't be running around messing around with just anyone I saw. Even though I was caught red-handed, I was a little irritated by that part and I asked him what that was supposed to mean. What, was he supposed to choose my partners for me or something?!

He just smiled at me, ruffled my hair, and told me to "trust daddy". Then, he left me in the room. I was perplexed, and not really sure what I was supposed to take away from that conversation. However, since I just barely escaped trouble, I decided not to try my luck any further. We didn't bring it up again, and I kept myself a mile away from any boys - which was not easy for my teenage, hormone-filled self.

A couple years passed by and my brother started being more and more involved in my dad's business. Since he apparently proved himself trustworthy, my dad started entrusting him with smaller tasks of his own. Almost every night my brother would come home, looking all smug, and rub his success in my face. How he was the one taking over the family's business and how soon, I would be calling him my boss.

"It must be nice just laying around, doing nothing after school," he would taunt me, "I guess if real men like my dad and I are the ones bringing bread to the table, there has to be someone who eats it..."

Needless to say, it bothered me. I wasn't interested in being involved with the business, but now that he was rubbing it in my face, I kind of started to. At one point, I couldn't take any more of his arrogance. I told him that we will see about that, although I didn't know what I was thinking. I knew next to nothing about the family business, and I couldn't see any way for me to participate in it that I would enjoy or be good at.

My dad, being the people person he always was, of course, caught on to this tension between me and my brother - even though we never brought it up in front of him - and would frequently remind my brother that I was an important asset to the family and that I was about to prove very important - it just wasn't my time to shine yet. It perplexed me back then, I didn't know what that meant, but it shut my brother's trap for at least a minute, so I wasn't complaining.

Which brings us to that one summer day when my dad finally made me understand.

I was twenty-one at the time and my brother was twenty-six. By this time, he already had his own little responsibilities when it came to dad's business, while I was focusing on my remote university studies. The stupid, arrogant comments from my brother never stopped, but luckily, with all of his newfound responsibility, we didn't have so much time to interact anymore, which was working out just fine for me.

One night, after our family dinner, my father asked me to stay for a while after we finished eating. That was usually the time when my father talked business with my brother. I was never explicitly uninvited from that, but I usually had no reason or interest in staying around for that conversation, so I usually didn't. This was a new thing for me.

"I have something business-related I need to discuss," he said to us, "And I need you both to be present this time."

My brother seemed as confused as I was and kept looking at me like I was supposed to know what was going on. After we finished eating, my dad left the table and went to his study. When he came back, he was carrying a briefcase.

"Thank you for your time, boys," he said in a formal manner - when it comes to business stuff, my dad always addressed us as his associates, rather than his sons, "I'll keep it short and clear. Peter, your tasks for the week remain the same. Make sure the negotiations with Roger from uptown continue and keep things neat and friendly with our friends from the police department. Sam, on the other hand, will be handling a completely new deal with none other than Mr. Angelo."

My brother almost choked on the sip of water he was drinking at the time.

"Mr. Angelo?!" he repeated, "You mean the gang leader from the commercial district?"

"The very same, yes," my dad nodded.

"That guy is a legend, dad!" my brother said in shock, "He controls the whole downtown area... And from what I've heard, he's not one to be fucked with! Are we making a deal with someone like that? That is huge!"

"That's exactly right, son," dad nodded, retaining his calm demeanor.

"And you're sending Sam?" my brother exclaimed, outraged, "He has never, NEVER, done anything like this before! He's gonna get eaten alive in there, and more importantly, the deal's gonna be a bust!"

"More importantly?!" I asked him, angrily, but my dad gestured at me to stop. He kept his eyes on my brother.

"You heard me right, Peter," he continued, still calm, "And you just perfectly demonstrated to us all why I'm not sending you to carry this out. You're great at organizing our regular partners, but you're too much of a hothead to make this deal happen. I know Angelo better than you, and a little bit of humility goes a long way with him. I'm afraid your brother has qualities that simply work better than yours when it comes to this deal. That's why I'm sending him."

The look on Peter's stupid face was priceless - he just froze with his mouth open and kept stuttering.

"I... I..."

"End of discussion, Peter," my dad said with a bit more of a stern tone. Then he turned back to me.

"Sam, this briefcase contains five hundred thousand dollars in cash. I will send my driver to pick you up tomorrow and bring you to Angelo's place. He will be expecting you. However, when you go in, you will be completely on your own. I assure you that nothing bad is going to happen to you there, son. As I said, I know Angelo and the deal is going to run very smoothly. However, his business is very important for us. And I'm sure you know our position compared to Mr. Angelo's. For once, we need to show we're humble, cooperative, and willing to do whatever it takes to earn his trust and his partnership. Can I trust you with this?"

I have to admit, the whole thing made me nervous. But with my brother, sitting right there, feeling so hurt and offended that I got a more important task than him, well...

"How could I say 'no', father?"

*****

My dad planned out everything in advance - all the actual details of what we were negotiating were set, the only thing was me sealing the transaction. Both our driver and Mr. Angelo were expecting me. The only thing I had to do is show up, hand over the money, make a good impression and get out of there. I was nervous about it for sure - I mean I was about to have a one-on-one with one of the most powerful men in the city, but I also knew I usually had no issue dealing with people. And I trusted that my dad would never send me into a situation like this alone if he wasn't sure my safety was one hundred percent guaranteed.

The only thing that I couldn't get out of my mind was why he sent me. Sure, my brother was a hothead and I was definitely more of a friendly person. I also wasn't as proud of my brother - it was obvious dad wanted me to suck up to Mr. Angelo a little bit to be able to close this deal and my brother would probably have issues with that. However, if it was just about handing over the money, were there really going to be so many opportunities for me to show any of that? No matter how unpleasant my brother was, I was sure that even he would be able to swallow his pride for a couple of minutes...

I decided not to think about it too hard and get dressed instead. I noticed that our house servant already prepared everything for me on my dresser when I was sleeping. There was my best suit, fresh and clean, folded nicely. There was also the money briefcase, of course. What caught me off guard was the pair of underwear sitting on the top of the clothes... Sure, our servant was expected to prepare everything for me so the fact that there were undies there didn't surprise me so much.

But these weren't my usual boxer briefs. No, there was a bright red, brand new jockstrap laying on the dresser.

Did dad decide to buy me some new clothes all of a sudden? Perhaps he wanted to buy me some new clothes just because... Or the servant messed up and accidentally gave me some of my brother's - even though this didn't seem like my brother's style either. Why a stylish jockstrap like this?

Again, I decided not to overthink it. After all, my dad chose me for this job because I was less of a stubborn grouch like my brother, who always had a hundred comments about everything. I started my morning hygiene and then put on the clothes. As I was finishing up, I heard a car horn outside. Our driver was already waiting for me. Perfect timing.

Both my brother and my father were out already, so there was nobody to say goodbye to. I grabbed the briefcase and left the house. One of my father's limos was waiting outside, with a new driver that we hired - I think his name was Michael? A handsome guy, with shoulder-length dark blonde hair and a nicely trimmed goatee.

"Good morning, sir," he said to me as I got into the car, "Hope you are feeling fresh and ready for today. Your father wanted me to ask on his behalf if you feel prepared well before the deal?"

"Absolutely," I assured him confidently. I was nervous, for sure, but in a way, I did feel in my gut that it was going to go well. What surprised me was the driver's reaction. He nodded in acknowledgment, but he also gave me this really strange smirk through the rear-view mirror. It was this strange kind of expression - as if he knew something that I didn't? That upset me just a little bit and shook my confidence just a little bit... What was I really getting into?

We drove off and I relaxed in the backseat. I put on my headphones and decided to put on some of my favorite music to calm myself down as much as possible before the deal. It helped a little, but I noticed that the driver kept glancing at me through the mirror all throughout the ride and giving me the same smirk over and over... What was that about? I contemplated asking him about it but ultimately decided against it. My father, the ultimate businessman, would not be concerned about the staff's opinion on business deals. He would just go and do whatever he needed to do, so I would do the same.

We finally arrived at our destination. Mr. Angelo was, of course, loaded and owned a bunch of real estate in the commercial district. The limo stopped in a gorgeous part of the city in front of one of Mr. Angelo's office buildings. It was a huge, modern skyscraper that hosted some of the biggest companies in the city. As I looked out of the window and saw the property of the guy I was about to be dealing with, it all started to dawn on me even more.

"Here we are, sir," Michael said, as he pulled over to the sidewalk, "Good luck with the... transaction."

Again, the weird tone! I shot the driver a slightly irritated look before I grabbed the briefcase and got out of the car. I felt like there was a rock in my stomach as I walked through the front door. I entered a luxurious lobby, with a massive receptionist table in the front. I walked up to it and try to appear like I knew what I was doing.

"Good morning," I greeted the receptionist, "I am here about the meeting with..."

"Mr. Angelo, correct?" she completed my sentence with a professional smile on her face, "Yes, he's already expecting you. Thirtieth floor. Here's your visitor's card."

I took the card and nodded to the receptionist before I headed to the elevators. There was a sign that only the middle one went to the twenty-fifth floor and above, so I chose that one. Then, I needed to use my card to actually confirm my floor selection in the elevator - apparently, Mr. Angelo's floors were off-limits for most people in this building.

A bunch of people clothed in fancy suits entered the elevator with me. They were all older than me and seemed so... mature and confident. I felt a little out of place, being the only one under the age of forty.

We stopped at every other floor, which gave me time to grow even more nervous. As the people in the elevator were slowly leaving, the remaining ones noticed the glowing "30" on the elevator buttons. They would look at me and raise their eyebrows. What was a young nobody like me doing, going all the way up to the boss?

The last guy left the elevator on the twenty-second floor. I was in the elevator alone, only with my thoughts. I felt a drop of sweat dripping down my chin as I watched the number on the display change all the way to thirty. And then the door finally opened.

The first shock of the meeting arrived - apparently, the elevator led straight to Mr. Angelo's office!

I watched the door open and saw a cozy-looking study room, with bookshelves all the way up to the ceiling. It had a very traditional setting - everything was wooden and old, but very classy. It looked less like an office and more like a set of a movie. To top it off, there was a fireplace in the middle of the wall, but it wasn't being used right now. The decorations weren't the most interesting part though...

There were three men at the other end of the room, right in front of a gigantic window that had a view of the entire downtown area. Two of them were standing at the sides of a massive wooden desk - dark blue jackets and red ties, all perfectly fitting and probably custom-made. I also saw two guns on their belts. I immediately identified them as Angelo's right-hand men - his most loyal and trusted goons that doubled as assistants and security.

Both were showing stone-cold looks on their faces and they watched me intently as I entered the room. They were both tall, muscular guys no sane person would mess around with. The left one was wearing a military flat-top haircut and had a scruffy face with a prominent goatee. The one on the right was stockier, completely bald, and with a scar on his face. The two of them would have been intimidating enough even without their boss in the middle.

Mr. Angelo was sitting behind his desk. He looked stunning for his age, only a couple of tiny wrinkles on his face would help you guess he was over fifty. Hazel colored hair with not a single shade of gray flowing down to his shoulders, a cunning look in his dark eyes that would tell you from a mile away he was a confident businessman, and a five-o-clock shadow on his face. He was dressed in a perfectly fitting striped suit and a bright red shirt, matching the ties of his right-hand men. That was topped off with a black hat and a belt with an insanely fancy silver buckle. His feet were casually put on the table so I could see his shiny black leather shoes that looked like he - or probably somebody else - took care of them every day.

They were all watching me - the goons with a calculated look and the boss with a sly smile. Standing there felt like standing in a spotlight on a stage.

"Um... good morning, gentlemen," I started, already feeling my voice growing a little weak and shaky, "I was told you are expecting me, I'm here on behalf of my father, Mr..."

"No need for the formalities, my boy," Angelo interrupted me, "I know who you are. Come closer and sit down with us. Don't be shy. We don't bite."

He winked at me and gestured at the empty chair that was positioned in front of the desk. I took a deep breath and crossed the room, clenching the fist around the briefcase handle.

I sat down before the gangsters. They looked even more intimidating from up close. I started panicking for a second until I remembered why I was here instead of my brother. I could push through this using my personal charm and close this deal with absolute success. I just needed to calm down a little bit.

I flashed Mr. Angelo a wide smile and went for a much warmer tone.

"I must say, it's an honor to be speaking with you personally, Mr. Angelo."

He smiled back, and his eyes looked me up and down.

"Pleasure is all mine," he responded, "What's your poison, little Sam? We should toast to the occasion."

"Oh, water is okay, sir," I waved it away. He smiled again and shook his head.

"Water is not gonna cut it, sport. Not today, not when you're dealing with me."

He gave me another wink. I got the message. This game was meant to be played under his rules.

"All right..." I nodded, "What you're having, then. I trust your judgment."

Just the right amount of ass-kissing, I was sure that it would work. I guess dad really made the right decision - my brother would probably storm out after being called "little Peter". Mr. Angelo turned to one of the goons and snapped his fingers.

"Rocco," he ordered, "We'll have two glasses of Macallan."

The taller hunk standing beside him just nodded and went straight to the minibar on the side of the room that I didn't notice before. I watched him before turning back to Mr. Angelo, who started talking to me again.