Sealing the Deal

"Personally, I'm a whiskey man," he said, still with that strange smirk, "You don't sound like you're too picky about what you put in your mouth, is that right, boy?"

"Umm..." that was a strange way to phrase it, but I just laughed, figured he was making a cheeky joke, and nodded, "I guess you could say that, sir."

The smile on his face got even wider. Slowly, he pulled his legs off the table just as the man named Rocco came back with two glasses of scotch. He grabbed one and raised it in the air.

"Cheers to us, little Sam."

"Cheers, sir," I did as he did and put the glass to my mouth. I've always hated whiskey, to be honest, and I didn't know crap about it, but I wasn't stupid enough to let that show, "It's amazing, sir. You can really appreciate how aged it is."

"Only the best of me and my partners," he responded, "Well... potential partners. The deal is not quite closed yet, is it?"

I nodded and figured that was a signal for me to pull out the briefcase. I put it on the table and pushed it a little closer to Angelo. He didn't seem to pay a lot of attention to it though, for some reason. He just kept staring at me.

"It's all there, sir," I assured him, "Five hundred thousand, just as you negotiated with my father."

He finally glanced at the briefcase and then turned to his goons.

"Can you believe this, boys? I told Sam that I might be willing to settle for half a mil... given that he found a way to sweeten the deal somehow," he said, amused, "I didn't think the old bastard would actually take me seriously."

All that went over my head, but I saw that both the goons lost their poker faces and were now cracking a smile. What was going on? Was this going well, or not? I couldn't tell...

"Um..." I said, blushing a little bit, "Sorry, but I'm not sure what you're referring to, sir. My father didn't really give me anything else."

"Oh, that's where you're wrong, boy. Your father gave you quite a lot," he said, again with that cryptic tone, before snapping his fingers again. This time, both the goons started moving - without a single command given to them. They slowly circled around the table and stopped at the sides of my chair, maintaining an uncomfortably close distance to me.

"We have high expectations of people we work with, you know...," Mr. Angelo continued, while I was busy looking around nervously to see what his two guards were up to. They still watched me with those smiles as they approached me from my sides. Crap, were they going to rough me up? Did I do or say something wrong?!

"Um..." I turned to Angelo, my heart beating a little faster. He didn't seem angry. On the contrary - he looked very, very pleased. His men had me surrounded from the sides. Rocco put his enormous monster hand on my shoulder and the stocky one, whose name I later found out was Lucius, nonchalantly stroked my hair with his fingers. I didn't like those toothy grins on their faces at all. I kept looking at Mr. Angelo, looking for a hint about what was happening.

"I expect all of my business partners to drop whatever they're holding the moment I ask them for anything and only tend to me, whether it's for business or just for my pleasure," Mr. Angelo kept explaining, "Do you think you're capable of that, Sammy?"

"Of course, sir, anytime you ask for anything, sir," I nodded frantically. The men on my sides stepped a little closer - their crotches now almost pushing on my shoulders.

"Well, Sammy," Mr. Angelo said, "Put your... mouth, where your mouth is, then. My colleagues and I would like some pleasure. Right. Now."

I heard two distinctive sounds of zippers opening on both my sides. I looked up and saw the men towering over me, grinning - they didn't have to say another word about what they expected me to do. I looked back at Mr. Angelo and saw the same expression on his face. Was I expected to... have sex with these three men?!

Suddenly, everything started to make sense - why father thought I was the one who should go on this mission, the reactions of the limo driver, everything. The first knee-jerk reaction I felt was being a little upset. My own father, whoring me out like this? Basically exchanging the virginity of his son for a business deal? He had to know that this would happen he wasn't stupid!

On the other hand... It showed me that he trusted me with this. Knowing why I was sent to carry out this task made things more understandable. He knew that I wouldn't hesitate and would do anything to seal the deal - not like my pussy-ass brother. No, I was a man of my word. I promised I would come back successful, so that's what I was going to do.

I was nervous, of course. Being fucked by one of the most powerful men of the city? The stakes were high, and I was inexperienced - if I fucked up because of that, I could bring down my father's reputation so low, it might never recover.

But on the other end, my inexperience was an asset here. It was one of the things that attracted Angelo so much. And it was hard not to get excited by the possibility. Even though this wasn't what I signed up for, I couldn't help but feel excited at the thought of fooling around with someone so powerful, and handsome...

I found myself repaying the grin on Mr. Angelo's face.

"Right away... boss," I finally answered. Both my hands went to their respective sides and wrapped around their inner thighs. Slowly, they went up until they reached the bulging bumps of man-meat, making themselves very visible between their legs.

My experience with anything above making out was pretty much non-existent, but I knew that was what Angelo was after. Breaking in an inexperienced boy, who was there to service him and anyone he tells me to. I was more than willing to play out this fantasy of his.

I decided to start with Lucius - I didn't have much experience but intuition told me that he would be smaller and therefore easier to take into my mouth. I was mostly wrong. The stocky, bald man was smiling down at me and I knew he was going to be happy with anything I had in store for him. And I wanted to give him my best. I reached into his open fly and stroked his thick manhood through his underwear. I underestimated him - he was definitely packing. And a small spot of wetness on the tip of his bulge told me that he was looking forward to this a lot...

Slowly, I pulled out a seven-inch, extremely thick cock that was already semi-hard and uncut. It felt so good and heavy in my hand, almost like some sort of a powerful, expensive gun. His balls were shaved clean and they were big, promising a huge, thick load. I licked my lips. Was it bad that I wanted to swallow, even if nobody asked me?

"First time looking at a man's cock, huh?" Angelo commented as he saw me staring at Lucius, "I can practically see the stars in your eyes... Go on, boy. Give into the excitement. Give Lucius a kiss."

I looked up into the gangster's horny eyes, leaned down, and gave him much more than just a kiss. I pulled his cockhead into my mouth and sucked eagerly on it, tonguing the uncovered part of the tip. And fuck, did it feel right... It's hard to explain what it is about a man's cock that just tastes so good. The taste itself is hot enough, but the immediate connection your brain makes with what you're doing - you, a cocksucker, opening your mouth to service another man - that's the real treat. I immediately knew that I was going to love this experience.

My mouth made out with it for a while before pulling away, with a thin string of Lucius's precum hanging loosely between my lips and his cock. Then, my fingers tenderly pulled his foreskin back and I was met with a beautiful, purple head and a whiff of that musk - not like the gross, unkempt body odor, no... Just a nice, earthy smell of a dick.

I didn't know much about sucking cock but I knew the potential of an uncovered cock head of an uncut guy from my own body. I leaned in, fingers holding the foreskin back, and my puckered lips went to take that sensitive head for a ride.

"Ohhh, fuck..." Lucius's deep groan told me that I was on the right track. His fingers were in my hair and he was pushing me forward impatiently. My lips didn't hesitate - they swallowed more and more of that hot shaft until the tip of his cock started tickling the back of my throat. I wasn't quite ready for that, so I started to pull out slightly and give the tip some tongue action instead.

It was my first blowjob and I fell in love with the act already. I started bobbing my head back and forth on the gangster's dick, which was now fully hard, taking more of him inside my throat, which was slowly getting used to the new experience. His hips were helping me with that too, as he was so eager to have the most of my mouth he could get. I was so glad he was enjoying it - I knew that the whole deal relied on my skills to get these mobsters off.

I got so into it in fact, that soon, Angelo's fingers had to snap me out of my trance.

"Don't get too attached, boy. There's more dicks in this room than one."

With that, he pointed me at Rocco. The taller, scruffier gangster seemed to enjoy the show that I was giving and already lost both his underwear and his pants. His cock was much longer than the one Lucius had. It was standing straight up from his thick bush of pubic hair, pointing upwards. Another beautiful uncut cock, waiting only for my mouth to show it what it can do.

Rocco was holding it by the base, lowering it to an angle that was more appropriate for my mouth. Well, boss's orders are boss's orders... And I wasn't about to pass on an opportunity to taste another dick anyway.

I moved in my chair and wrapped my lips around Rocco's tool without hesitation. He tasted so good, and even a little stronger than Lucius did. Unfortunately, I didn't get a lot of time to savor the taste, because the next thing I felt was Rocco's huge hand on the back of my head.

"You'll have to be a bit understanding with Rocco," Mr. Angelo chuckled, "He's always been a bit impatient."

What an understatement that was! The guy didn't care that this was my close-to-second time blowing somebody, he started jackhammering my throat right from the get-go! His huge dick was stretching my throat and testing my gag reflex without mercy. I bulged my eyes out as I started getting facefucked while repeatedly slapped on the chin with the gangster's low hangers. The man's hairy bush kept rubbing against my nose so fast that I felt it was going to leave a mark! I didn't have a lot of options, besides just sitting there and taking it, being facefucked like a cheap whore. Which, I'm ashamed to admit, didn't feel as bad as it probably should...

Rocco was grunting periodically as he violated my untrained throat. His precum was leaking straight into my stomach and with the fast thrusts, it also got everywhere else - soon my lips were all sticky and messy from the gangster's precum. I could smell it and it felt so dirty and incredible... if only he would slow down just a little bit so I could enjoy it properly.

"All right, that's enough for now," Mr. Angelo commanded after his goon violated my face a little bit more. I was panting and coughing when Rocco finally pulled his merciless dick from the depths of my throat. I looked up at him and he gave me a toothy grin and a nod of approval - apparently, he didn't expect me to be able to keep up with his temper and he was pleasantly surprised.

"I'll let you choose your own tempo now, slut," Mr. Angelo said, sipping his drink and rubbing his growing bulge, "Give me a bit more of a show before I let you taste the real prime beef you can get in this city. And don't forget to use your hands - if you're going to be working under me, I expect you to be resourceful and multitask."

I went back to sucking Lucius, which was a refreshing change, as his thrusts were not as aggressive and I could really focus on enjoying his cock and doing a good job. Following Mr. Angelo's instructions, I reached out with my left hand and started stroking Rocco, while I sucked Lucius - servicing the two of them at the same time. I loved being able to just lick, suck and enjoy the beautiful piece of meat in front of me. I enjoyed playing with his foreskin, his piss slit, and his balls, which he particularly seemed to enjoy.

But on the other hand, when I finally switched up and got back to Rocco, I kind of started enjoying his treatment too. It was a lot on my throat, sure, but being grabbed and held by a man like him, stuck in place while he debased himself on me, showing the true animalistic nature that he was hiding under that suit... That also got me really fucking hard, I'm not gonna lie. My other hand had to focus hard on jerking Lucius off while I obediently served my mouth on a silver plate to this savage only to have it ruined in the hottest way.

Alternating between the two dicks, the taste of the two men started mixing in my mouth. I started savoring, comparing... but I couldn't decide which was better. I only knew I wanted to have more. Precum was dripping down my chin at that moment as I was quickly switching between the two gangsters like I was at an all-you-can-eat buffet. The whole scene was dirty and hot - hot enough that even Mr. Angelo decided it was time he got some action.

"All right," he said, "That's about enough. I think it's time for you to crawl on this table, boy."

I pulled Rocco's dick out of my mouth and saw the devilish look in Angelo's eyes. The man was a true movie-like villain, but of the classiest, hottest kind. I wanted to serve him, I wanted to submit myself to him, to pave the way for my father with whatever my body was capable of. I stood up from my chair, wiped the precum away from my chin, and stepped closer to the table.

"That's right, boy. Get on it and lay on your belly. Don't be afraid to push out that plump ass. My men won't hurt it, I promise you."

I heard the two goons chuckle behind me. Well, whether he was joking or not, I wasn't about to give up at that moment. I crawled on the table, ass in the air, and found myself right in front of Mr. Angelo's crotch. The goons behind me wasted no time and with their help, my pants loosened and ended up around my ankles, leaving my ass exposed in my new jockstrap. I was more focused on Mr. Angelo though. He smelled like expensive, heavy cologne... but I was sure that the musk of his cock was going to be even better. I was hungry for him, and he knew it.

"What do you say, kid? Are you ready to suck off the boss of this city?"

"Yes sir... aah!" I exclaimed as I felt an unfamiliar sensation on my backside. Two strong hands on one of Angelo's associates grabbed my ass and spread my cheeks wide. Then, I heard one of them chuckle and kneel behind me, smacking his lips.

Mr. Angelo stood up and I could see that the gangster was packing a big gun... and I didn't mean the actual firearm holstered to his belt. The tight suit pants were hardly effective at hiding the outline of his monster of a cock. It looked very impressive together with the massive silver buckle. Mr. Angelo rubbed it teasingly as he stepped closer to the table.

"Your father is a good businessman, you know," he said, as his hand met my hair. He stroked it and pulled it up a little bit so I could look into his eyes. "He knows how to make a good offer. I'm gonna send you back to him with an empty suitcase and your ass full of cum."

"Hmmph..." I moaned as I felt something wet pushing onto my hole. Based on the light scratching, I figured it was Rocco who was about to eat me out. I've never had anyone touch me there, so I couldn't help but feel a little strange about it... but his tongue did feel good. Really good. Mr. Angelo, ever so good at reading people, noticed.

"Nervous, huh?" he asked. I pondered for a bit if I should answer that but since he already knew and appreciated the fact that I was a virgin, I nodded yes.

His fingers slid down to my face and stroked my cheeks. His warm thumb started rubbing against my lips, applying slight pressure to make me open my mouth.

"Don't you worry about anything, my boy," Mr. Angelo's strangely calming voice said, "Rocco is going to make you feel really nice and prepared for me, while you service my cock like you just serviced his. Are you ready for me?"

I decided it was about time I pulled myself together - this was a business transaction after all. I needed to stay professional. I opened my mouth to accommodate his finger and sucked on it eagerly, like it was his cock, while my hands reached forward to open his pants and get a look at that beast.

Meanwhile, Rocco wasn't wasting time with my asshole. His bearded mouth started feeling really pleasant against my virgin opening, licking and smacking obscenely. The gangster was going to town on my ass and his tongue started being more and more demanding. Even though my hole began very tight and unwilling, it slowly started opening to the mobster's skillful tongue. He was so good at it that I wondered if part of his job was what he was doing right now - loosening tight holes for his boss. Or perhaps it went even further than that?

My hands were shaking as they opened Mr. Angelo's fly. The buckle was almost heavy enough to pull down the pants when I finally managed to get them open. I grabbed the edge of his pants and pulled them down, revealing a pair of brand and expensive-looking underwear. His cock was long enough that the uncut head was partially sticking out of the leg part... and it was only semi-hard!

"Who's the biggest man in the city?" Mr. Angelo asked me.

"You are, sir," I answered with my eyes glued to his cock, being completely honest.

"And who do you belong to?" he growled as his fingers played with my hair.

"To the biggest man in the city, sir" I played along.

"And when I text you, or your father, that I need you to come here, what are you gonna do?"

"Drop whatever I'm holding and get right here to service you, sir."

"That's right, boy. Now, don't waste any more time and show me how much you want to make your daddy happy."

I wasn't sure if by "daddy" he meant himself or my actual dad, but at that point, I was fine with both. I wanted to show my dad that I could close this deal on my own, and more importantly, stick it up to my brother. And when it came to Angelo, well, my mouth was already watering just looking at the bulging outline of that cock. He could be my "daddy" any day.

The underwear slid down and his huge tool swung out, looking powerful and heavy. A big, veiny, uncut cock and a pair of round balls that looked ready to shoot. I exhaled loudly, partially because of what I saw and partially because of Rocco's tongue, which successfully pushed deep inside my hole.

Mr. Angelo chuckled and stepped just a little bit closer, pushing his shaft against my face. I took a whiff of his cologne mixed with his amazing natural smell and waited no further. My mouth opened almost automatically to start pleasuring the big boss. He was bigger than both of his goons, which was fitting - he was the biggest man of the city after all. I thought I knew that already, but now I could finally understand what that truly meant.

His cockhead felt amazing in my mouth and almost made me feel honored to be in that position. My throat was trained from Rocco's rough treatment from before, so it was able to relax easily and open itself to make room for Mr. Angelo's dick. Third cock I've ever taken and I already knew that I would never stop doing this. Having a man - and not just any man, but the most powerful gangster in the city - throb and leak precum in my mouth was so hot.

Rocco was really enjoying my ass and I felt more comfortable and loose with every passing second. The hard surface of Mr. Angelo's table actually almost brought me to the edge - Mr. Angelo's thrusts and Rocco's face planted on my hole were sort of shuffling me around, rubbing my hard dick against my pants and the wooden desk. Luckily, I was able to hold back. I wasn't sure if the boss wanted me to cum so soon.