The Loan From My Best Friend

But, I did not have time to contemplate this. I needed to collect the money and pay the collection guys.

Charles' taste was on my mouth and his smell was in my nostril. I cleaned my mouth, face and nose, and got rid of most of it, though there was still traces of it. Why am I not disgusted by this? It did not seem to bother me in the least.

CHAPTER 5

When I returned to the living room, Charles was in the kitchen making us sandwiches. I cleaned up the mess I made on his floor without him noticing it.

I went to the kitchen and we made eye contact. But, there was an awkward silence. It seemed like neither of us knew what to say to the other.

Then, after a few second awkwardness, he handed me a sandwich and said, "I made us club sandwiches. Want to watch some TV?" I told him, "I would love to, Charles. But, I have to run to make a payment."

He nodded and said, "I put the $6,000 in an envelope on the coffee table. I use to pay Carmen $500 for what you just did. But, I think you deserve $1,000. I will only add $5,000 to your debt."

I realized this was a big compliment and I couldn't help but blush and smile. I hoped he did me blushing and smiling.

After I picked up the envelope, he walked me to the door.

When we reached the door, he asked me, "Jim, are we good?" I turned and came back to the door. I said to him, "Yeah Charles, we're fine. I took my medicine. I'm good. I think I'm going to cut down on my gambling." I was facing him, but, looking down.

Then he said, "Well, what about all the money you still owe me?" I was taken aback that he would mention that now. I said to him, "I don't know. I don't have a job right now. I can't pay you back right now."

He said, "Yes you can. We work out an arrangement for you to pay it off some way." I realized it wasn't about the money. I rocked his world today and he wanted more. I asked him, "Pay it off some other way? Like more of your medicine?"

He said, "Well, that is an option."

It was a shocking proposal! I could not believe he was proposing this! But, even more shocking was that I was flattered by it and happy he mentioned it! I asked him, "So, let me understand this. You want me to give you 55 blowjobs to pay off my debt?"

He replied, "At twice a week, you would satisfy your debt to me in about 9 months."

I thought about it for a second. Unless I had a big gambling win, it would take me decades to pay him back the $55,000 I owed him. But, I was not just considering the debt. The ecstacy I had experience blowing Charles had turned me into an instant addict. I cannot understand how I came so hard worshipping his cock, but, there was no denying I had reached new heights of ecstacy.

But, I was not ready to admit anything. I replied to him, "I don't know, Charles. I thought this was just a one-time thing. It's not my thing. But, I will give it some thought." I saw him put on a nervous smile, "Jim, this would be better for you than spending the rest of your life owing me money."

I replied sarcastically, "So you are doing me a favor then, making your offer?" He answered, "You want me to be candid? I told you Carmen gave me the best blowjobs. I can no longer make that statement." I looked down at the floor and blushed.

"I'll think about it, okay?" I said.

He smiled and said, "I only have one special request that goes with that offer."

"What is it?" I asked him. He said nervously, "Well, I used to buy Carmen sexy outfits that I liked her to wear for me. It was important to me to be indulged in this."

I became curious and asked him, "What kind of outfits?"

He said, "Nothing too weird. Just sexy outfits. Some outfits were standard stripper outfits, some where roleplaying costumes, and some were fetish outfit, like leather thigh high boots, fishnet stockings, latex corsets, that sort of thing."

I said to him, "No, Charles! I am not a drag queen or cross-dresser. That's a deal breaker for me!" He replied, "I'll give you a $5,000 bonus if you agree to dress up for me as part of our arrangement." I nearly gasped. I could not believe he was willing to pay me that much just to cross-dress. It must be big fetish for him.

I said to him, "I need to think about it."

He said to me, "Hold on just a second. I'll be right back." He went back into his house and came back a few seconds later with a large bag. "What is this?" I asked him.

"It is a few things I bought for Carmen to wear for me before I she told me about her retirement." He explained. "There are some thigh high boots and stilettos, leather skirt, stockings, fishnet tops, wigs and other goodies in there. You are her same size and same body type. I bet you even share shoes size. Just try them on and see how they feel on you." He said. "There is no reason to make a big deal out of it. It is like wearing a costume for a play or for halloween." I was hesitant to grab the bag.

He said, "Five thousand cash for doing something pretty damn harmless like wearing a costume. Carmen didn't charge anything extra for this, she loved the outfits I bought her."

I decided to take the bag, though I wasn't sure I could go through with it.

"Charlie, you are trying to turn me into a whore!" I protested.

He smiled and said, "No, your gambling has turned you into my whore. Maybe I should be encouraging you to gamble more, rather than less. I will own your ass if you continue to borrow money from me. I will lock you up in a room in this house and use you as my indentured sex slave."

I looked away from him and blushed. I thought about being Charles' live-in submissive cocksucking sex slave and realized I was biting my lower lip and beginning to get aroused, again. What is happening to me?

Then, I looked him in the eyes and said, "Charles, just so we are clear about boundaries, you are never ever sticking your cock in my asshole, okay? I would not let you do that for a million dollars. Our arrangement will be strictly blowjobs and, maybe, dressing up, but nothing beyond that! Ever. Do you understand?" I asked him.

He replied "I hear you, but, you should never say never. I mean, you could change your mind in the future." He said.

I said to him, "No! I have to draw the line there. You have forced me to compromise my masculinity and that is all I have left. If I give up my ass, I will have nothing left of my masculinity."

Charles relentlessly agreed, "I get it. I wish you would at least leave it open for future consideration. But, I hear what you are saying."

We shook hands awkwardly and I left him to go pay the thugs the $6,000 I owed.

(More to cum in Part 2.)