The Loan From My Best Friend

PART 1

CHAPTER 1

"You already owe me $50,000 and want to borrow another $5,000?" Charles said exasperated. "You are digging yourself deeper and deeper in the hole with your fucking gambling! When is it going to stop, Jim?"

He looked me straight in eyes and asked me, "How are you planning to ever pay me back, Jim?"

I looked down and said to him, "Charles, $55,000 for you is a drop in the bucket, man! I have no one else I can borrow from and if I do not pay these guys $5,000 today, they'll put me in the ER, maybe the grave!"

Charles looked at me with a perplexed expression.

We were standing in his kitchen eating sandwiches. Charles was my best friend from college. He is white, blue eyes, blond, a little over 6 feet tall, athletic build from working out every day and, at 25, he had already sold a software company and was worth a few million dollars.

I am six inches shorter, half-white and half-Latino, skinny, not athletic, and not as attractive or as successful as him, and one year younger.

Yeah, life is grand for him and a bitch for me.

"I have become your enabler! You continue to gamble because you know I am here to bail you out! I have to put a stop to that." He protested.

"Please, Charles! Now is not the time for an intervention. They can seriously hurt me if I don't pay. We've been best friend since college! You want to see your best friend dead?" I pleaded with him.

The guy that ran the underground card games had two thugs that come looking for you if you did not pay your bill. If you try to hide, that only makes the inevitable much worst. I've seen guys never walk again, because, they tried to hide.

Charles said, "I will not be your enabler, Jim. I cannot just give you another $5,000. It has to cost you something or you won't stop!"

"Fine. You want me to come work for you until I pay it off?" I asked.

There was silence. We were both thinking, but, I couldn't come up with anything I could do for him and it appeared neither could he. He was a software engineer. But, all I knew about computers is how to surf the web for porn.

Charles looked at me and said, "I wish I could give you a job, but, I can't think of anything. I would ask you to scrub my toilet, but, I already have a lady that does that and she's the best maid I've had. I can't afford to lose her."

We continued to eat our sandwiches and he had an expression of being in deep thought.

Finally, he said, "My all time favorite stripper at the strip club retired. She's going to Nebraska to marry some jerkoff." He said.

I did not understand why he was changing the subject. I need $5,000 from him. I didn't want to talk about some stripper.

He said, "Her name is Carmen. She worked at Paradise Gentlemen's Club."

"She is a hot little Latin girl, about your height and your complexion. Actually, she could be your twin. I am really missing her. She gave the best blow jobs and she had a nice tight pussy. She was my girl whenever I needed some relief, you know what I mean? I am going through serious withdrawal symptoms right now without her." He explained.

"Sorry about that, Charles." I said.

"Can we get back to the subject of you lending my 5 grand so I can continue to be alive a little while longer?"

Finally, he said, "Jim, I need to get serious with you to get you off your gambling addiction. I can't just give you the $5,000. I am not going to be your enabler. If I give you the money, I need to make it painful for you. I need to degrade you and put you through hell to get it."

I said to him, "What, like hazing? Like when we joined Alpha Mu Delta in college? Yeah, yeah, whatever. Just give me the money and you can haze me. I'll eat a goldfish or whatever."

Charles looked at me sternly, and said, "You're not listening to what I am saying, Jim. Carmen sucked my cock and balls and she let me fuck the shit out of her and I only paid her $500 for a blowjob and $1,000 for full service. You are asking for $5,000. So, what does that tell you?"

I replied, "What the fuck, Charles? I'm not asking you to give me $5,000. I am just asking for a loan. I'm going to pay you back."

Then Charles said, "You already owe me $50,000. I'm not sure that if I give you $5,000 I am ever going to see that money being paid back to me."

He looked out the window and said, "I had great respect for Carmen. She provided a stellar service to earn my money, she didn't just beg or try to guilt me into giving her charity. She was the best cocksucker I have ever met in my life! Her retirement is going to fucking kill me! I don't have time to go out looking for a girlfriend, I just need to get serviced twice a week."

I said, "What the fuck are you saying, Charles? You want me to be Carmen?" I chuckled, but, he did not.

I yelled at him, "You are turning your back on me, your best friend? $5,000 is nothing to you, man! You're rich!"

Charles replied, "I'm not turning my back on you, Jim. I'm saying yes. I will loan you the money you need. But, you have to suck my dick! It's actually a brilliant idea. I need my dick sucked real bad, and, you need to suffer humiliation and pain to make you quit your gambling addiction."

Surely, he was joking. I waited for him to laugh. He did not.

He explained, "I cannot continue to be your enabler, Jim. I'll loan you the money you need, but, it has to cost you a lot. Sometimes men need to be torn down to be rebuilt in a better version of themselves."

He looked me straight in the eye and said, "You'll hate me for making you do this, Jim, but, it will make you stop your gambling. Someday, you might even thank me."

I was flabbergasted.

I still waited for him to tell me he was just kidding. But, he didn't.

My God, he cannot be serious!

The room felt like it was spinning. I felt lightheaded.

"Think it over. The money is yours as soon as I cum in your mouth." He said.

I said to him, "Charles, you're kidding right? Please tell me your kidding! You're not gay and I'm not gay."

He replied, "No Jim, I'm dead serious. We've had conversations about your gambling for the past year and you just keep coming back again begging for another bailout. Only something really drastic will break your downward spiral." He said.

I exploded, "You are an asshole, Jim. You are a fucking disgusting jerk. You gay bastard! I would rather die than suck your dick! Fuck you and your money." I headed for the door.

He sighed and said, "I cum fast, Jim. It is really a good deal! We can treat $500 out of the $5,000 as payment for services, so, I'll only add $4,500 to your existing debt."

I walked out of the door shouting to him, "Fuck you, Jim. You queer asshole!"

Chapter 2

The motherfucker! That fucking motherfucker! I was fuming.

Later, when the thugs came knocking on the door to my apartment at about 8:00pm, I opened the door. You might think that was stupid, but, resisting the inevitable only made it twice as brutal.

The two thugs must have been at least 6 foot 2 and built like linebackers. One was white and the other was black.

They invited themselves into my apartment.

"You got the money you owe Sebastion?" The black guy asked me.

I looked up at them. "Please guys, give me just one more day. Please!" I begged them.

The white one pulled out brass knuckles from his pocket. He ignored me and spoke to the black guy, "I bought these brass knuckles this morning. My last one broke while I was punching and smashing Pete's skull. They don't make them like they used to."

If I had not taken a piss ten minutes before their arrival, I would have pissed on myself at that moment.

They started to remove their jackets. Then, the cell phone of the black guy rang and he answered it. From what I could hear, some guy that must have been more important to them than me had been spotted about ten blocks from us.

The thugs looked at each other and then looked at me.

The black guy said to me, "Jim, it's your lucky day. You get one more day. Be smart and use it well, rob a bank or something. We will be back at the same time tomorrow. Do not even think of hiding and making us come looking for you. Oh, and by the way, the extension is going to cost you an additional $1,000."

With trembling fingers, I spent the next three hours making phone calls to everyone I knew trying to find someone to lend me money.

CHAPTER 3

The next morning, I bought a mask and a toy gun and I went to a liquor store to rob it. But, I couldn't go through with it.

By 5pm, with only three hours left, I drank a few glasses of whiskey. I considered driving to Mexico and other crazy ideas. When I was all out of crazy ideas, I called Charles.

He picked up the phone and I said to him, "I'm asking you, again, please lend me five grand. It's just a few coins to you."

But, he was unrelenting. He said, "Jim, I am doing it for your own good. I have to make you suffer an extreme degree of humiliation to deter you from further gambling. Just take your damn medicine."

Then, he sighed and said, "Well, I have to go. I am in the middle of writing a new software. Catch you later."

I said, "No, don't hang up. I'm coming over."

He was quiet for a few seconds.

Then, he asked, "You are coming over to, um," "Yes, Charles." I interrupted him, "I am coming over to blow you, you fucking prick! I have no choice! These bastards where at my apartment today and I'm lucky to be alive. Please, take a shower. I'll be there in twenty minutes."

I hung up the phone. This was it. I had no other choice. Fuck it, I can get through ten minutes of hell.

I got to Charles' house and he let me in. We sat awkwardly in the living room. Neither of us knew what to say to the other. It was tense and awkward.

Charles brought us rum and coke. He mixed us drinks.

I did not beg him for the money anymore. I was exhausted of begging. I just wanted to get it over with. I told him, "I need $6,000. I got an extension yesterday, but, it cost me $1,000 more."

"Sure, Jim." He said.

I chugged some rum straight and said to him, "Pull your pants down! Let's get this over with!"

He got up to dim the lights and turned on the radio to some slow music. I said to him, "Charles, this is not a fucking date!"

He said, "Jim, I'm just trying to make this go easier for the both of us."

He sat on an arm chair, pulled his pants down.

He pulled his head back, looked up at the ceiling, then, closed his eyes.

He said nervously, "I guess I'm ready when you are."

CHAPTER 4

I had consumed enough alcohol to give me some liquid courage. "I can do this." I said to myself. It is abhorrent, but, getting my skull bashed in is worst.

I walked to where he sat and got down on my knees in front of him.

I kept encouraging myself by repeating in my head, "You CAN do this!"

His cock was limp and it was about 6 inches soft! I just stared at it for about a minute.

"Well?" Charles asked.

"Don't rush me, dammit!" I said.

He said, "You can start by just touching it, if you don't want to put it in your mouth right away. But, don't try to cheat me out of a blow job or you get nothing."

I wrapped my right hand around his limp dick and it came alive in my hands. It got hard and grew several inches longer. I starred at it stunned guessing must have been at least 9 inches long and massively thick! I had only seen cocks this big in porn. It transformed in my hands to a big, thick and heavy cock!

I started to stroke him gently in a steady rhythm. I felt his breathing get deeper and he arched his back. It felt so different from playing with my own dick. Charles was about twice as long and three times as thick. I wished my cock was as big and fat as his. At the risk of sounding weird, I must say it was an impressive cock.

I tried to imagine how I was jerk off if I had a cock like Charles'. I pretended his cock was mine and I was touching myself. This made it easier to play with his cock. I stroked it how I would have liked to be stroked. I grabbed him a firmly using my thumbs to tease the head of his cock.

He started making whimpering and moaning noise and he got dripping wet with pre-cum.

I squeezed his balls and teased the underside of his shaft and his moans and grunts got louder. He was getting very excited. I teased him and stroked him. He was loving everything I was doing with my hands. This was easier than I had imagined, at least the touching part. It was surprised that I was not sick or repulsed by what I was doing. I was adapting.

Then, Charles said, "Carmen, baby, suck my dick now." I brought my face closer to his dick until I could smell his musky scent. I closed my eyes and I pulled my tongue out. But, I chickened out at the last minute. I couldn't do it.

I tried two more times, but, I chickened out both times.

On the fourth attempt, the tip of my tongue just barely touched the tip of his cock. I tasted the salty pre-cum. It was a weird salty taste, but, not the most horrible thing in the world. "Yes, I can do this." I convinced myself.

I licked the tip of his cock.

Charles pre-cum was viscous, salty, foamy and sticky. Little sticky strings formed between the tip of his cock and my tongue, but, they broke and fell down to my lips and chin when I moved away from him. Instinctively, I licked my lips to clean them and got more taste of it.

I hate to say this, but, the taste wasn't all that terrible. I have done shots that tasted a lot worst. I felt a little emboldened and continued to tease him with a few quick licks.

I thought about the areas of my dick head where I am the most sensitive and I flicked my tongue in those spots. He whimpered and moaned.

I was teasing him real bad!

To my surprise, I was not hating this experience. I love to go down on girls and this did not feel so different, except for the obvious. Charles said, "Suck it already!" and grabbed the back of my neck to pull me to suck his cock.

I said to him in a fake girl voice, "No baby. Not yet. Carmen wants to tease you a little more." This made his cock jump a couple of times.

He begged, "Carmen please! Suck me already!"

He grabbed the back of my neck a few times, but, I resisted him. He begged and begged and I teased him mercilessly. I was getting even with the bastard by sexually torturing him!

Then, I realized that more than 10 minutes has passed already and I was prolonging this for both of us. I reminded myself that I wanted to get this over with as soon as possible.

I let him grab the back of my neck and pull my face to his cock. But, once I submitted to him, he became forceful and excessively rough. I got a taste of what it is to get face-fucked. Charles huge cock felt like it was going to tear my jaw apart and when it reached my throat, I had a really bad gag reflex and I couldn't breath and I started choking!

Charles released his grip on me when I started to gag and cough. My eyes were moist with tears. I felt like I was going to throw up.

"I'm very sorry." said Charles. "I did not mean to get so aggressive! You teased me into a frenzy and I got carried away." He said.

Surprisingly, I did not feel any anger or resentment. I was actually flattered by him saying that I teased him into a frenzy. I felt my own dick hard. I did not understand it, but, I realized I was horny and I started to touch myself. I have never been attracted to guys. I can't be gay. Maybe I was excited because I hadn't had any sexual contact with another human being for over a year.

I said to him, "It's okay, Charles. Don't worry about it. I'm fine. Just cum already." I did not want him to go soft and make me start all over.

I just needed to quickly learn to overcome my gag reflex and to know how much of his big fat cock could actually fit in my mouth. I started with just the tip in my mouth and progressed slowly.

I grabbed his wrists to prevent him from attacking me again, though, he is a lot stronger than me and I would not be able to actually stop him if he was determined to fuck my skull.

The musky smell of his manhood, the salty taste to his pre-cum and its thick sticky texture quickly become familiar very quickly. It seemed that my limit was one-half of his dick in my mouth without gagging. I gently fucked him with my mouth. I squeezed my lips to make them feel like a tight pussy. When all I had in my mouth was his tip, I licked the head like a lollipop and this drove him crazy.

Charles was moaning like he couldn't take much more of this. "Yeah! Yeah, Carmen! Oh my God, Carmen! Fuck, that feels incredible!" He moaned, sounding like he was about to cry from joy.

Was it weird that I was feeling good about his compliments? I was surprised by how quickly I evolved into a willing cocksucker. I started to feel good about sucking Charles cock! I had gone down on two girls in my life and they both seemed to enjoy it, but, not like Charles was enjoying my mouth, not even close. It seems I was by nature a better cocksucker than clitlicker.

Charles' moans and convulsions made it clear that I was rocking his world. I felt strange pride in this. I got into it and gave his cock all the love and worship it deserved.

I felt comfortable enough to put his hands on my neck. He was about to cum and I was willing to let him fuck my face for the last few seconds left. He grabbed me with his big strong hands on the back of my head and pulled me towards him forcefully.

Charles fucked my face. He was a bit rough, but, he knew how much I could take and avoided hurting me. He was trembling and grunting like a wild animal.

My biggest shock of all this was that my dick was hard as a rock. I unzipped my pants, pulled out my little dick and started jerking off.

Why was I aroused by this? I was being degraded, emasculated and violated! I was confused about why this experience was making me so damn horny!

Charles' cock throbbed in my mouth and I knew he was about to cum. I stroked myself fasted to catch up to him.

When he whimpered, "I'm about to cum!" I was ready to cum too!

God, I have never been so horny in my life! I was swimming in uncharted waters, because, I had never experienced this level of sexual intensity. My heart was beating out of my chest and I was barely able to breath fast enough.

When Charles' body indicated his climax was imminent, I took as much of his cock as deep in my mouth as I could. I wanted him to shoot his load down my my throat so I gulp it down. I felt his body tighten up in one last convulsion, and then, the shots were fired! His body spasmed, and, with a loud grunt, his cock exploded in my mouth! He moaned while cuming, "Drink your milk, Carmen! You submissive little cocksucker!" He grabbed my head firmly not letting me pull away. He held me like he was afraid I would pull away and let a drop of his cum go to waste. He did not know I wanted it about as bad as he wanted me to have it. His cum poured down my throat and I swallowed as fast as I could, but, the load was so heavy it was impossible to keep up with it. Some spilled on my shirt.

I came too! My orgasm was shockingly powerful! The tidal waves of my orgasm flooded my brain and I thought I was about to pass out. I spasmed, my toes curled and my back arched. My eyes went to the back of my head. But, it did the best I could to hide all this from Charles. I did not want him to know that, what was supposed to be my awful "medicine" had made me cum harder than I had ever cum in my life.

He kept his eyes shut for a few minutes after cuming. I hoped that he had been so overwhelmed with his own orgasm to notice mine, even though I had moaned with his cock in my mouth.

I had to clean up. I had also left a puddle of my own cum on his marble floor. "I need to clean up. I'll be right back." I told Charles, and went to the guest bathroom.

He still had his eyes closed and did not reply.

When I walked in the bathroom, it suddenly hit me! Did that really just happen? My God, it did! I had just been degraded, demasculated and fucked in the face by a dude, my best friend, and, it had turned into the best sexual experience of my life! What the fuck is wrong with me?