The Bookie Ch. 01

When I was in high school, I learned of a guy who was acting as a local bookie, taking bets on sports games. Money was not easy for me to come by back then, so when I heard of the great odds he was giving on my favorite football team, I couldn't pass up the chance to place a large bet on such a sure thing. My plan was to score a good sum on the win, which would give me money for dates and nights out on the town for a while.

Much to my dismay, my team lost and I found myself owing money I didn't have. I tried to run a tab, hoping that I could clear my losses with another bet that I would win. However, John (the bookie) said that new customers have to settle up losses before placing further bets. I explained that I didn't have the money at the moment but could get it soon. He said I could have a week, but after that he would need to be paid in full or he would owe interest to his contact with whom he placed his bets.

I didn't know how I was going to come up with the money and during the week I tried everything I could think of short of stealing. However, after the week had passed I still had no money. When I explained this to John, I asked if there was any way that I could pay in installments. He told me to come by his house after school and he would see what we could work out.

After school, as I walked to his house, I worried about how I was going to be able to raise the money to pay off the debt with interest without my parents finding out. I had heard some stories about the guys that John was connected with and worried about getting on the wrong side of some shady characters.

When I arrived at John's house, I found he was home alone. We sat down to try to come to some kind of arrangement. He explained that he was being charged 20% interest per week. I realized that I would be lucky to make interest only payments working whatever odd jobs and chores I could to get paid. I asked him if there wasn't some way he could forgive the debt.

That's when John said something that caught me totally by surprise. "Look," he said, "you meet me here after school every day and I'll credit you $20 for each blow job you give me. At that rate, you can be paid off in about three weeks without having to come up with any cash of your own. Since it's been a week already, you already owe $40 interest."

I was stunned. I didn't say a word. I didn't know what to say. Sensing my apprehension, he added, "I'm always home alone. Nobody has to know. We'll keep it between the two of us. You can work off your first payment starting today."

"I...I don't know," I said.

"How are you going to pay it off otherwise? You haven't been able to come up with any money yet." He pause a moment and then decided to take charge. He got up and grabbed my hand to lead me back to his room. "It's really your only option," he said. "Follow me."

He tugged my arm just enough to get me to get up and I followed him back to his room. He went over to the bed, unzipped his jeans and pulled them off rather quickly along with his underwear, revealing a rather nice-looking cock. It was still flaccid, probably about 4-5 inches long and a couple of inches around. He was circumcised, and except for a patch of hair at the base of his cock, was rather hairless on his shaft and balls. He got on the bed laying on his back and propped his head up with a couple of pillows.

"C'mon," he said as he began to stroke his shaft slowly and gently. I came over to the bed but didn't get on it.

"I don't know what to do," I said.

"Just start by stroking it a little and then lick the shaft to get me hard. Do what you think you would like if you were getting head. I'll tell you what feels good." I hesitated for a moment and then got on the bed on my stomach and positioned my head between his legs. I took his member in my left hand and began to stroke it some. It was a strange sensation. It was like I was holding my own cock yet I wasn't feeling it. I began stroking up and down the shaft with my thumb teasing the underside of the shaft. I could feel it growing and stiffening by the moment.

"Okay, go ahead," he said. I knew that meant he expected me to start sucking on it. I realized there was no point in turning back now so I lowered my head toward his dick and opened my mouth. As I got the the head of his member, I stuck my tongue out slightly and closed my eyes as my lips encircled the head. I felt him flinch a little, pushing just the head into my mouth while he let out a little moan.

I started working my tongue around the underside of his cock, just below the head--the part that I find most sensitive on my own dick. I started a slow up and down movement, taking in about another inch or so of his now-firm shaft. His cock had grown to probably 6 1/2 or 7 inches and was probably as big around as a toilet paper roll. I had to open my mouth really wide to accommodate it all.

With each time I plunged onto his shaft, he responded by pushing his hips upward into me, encouraging me to take more and more of it. While the rhythm was still slow, I was trying to take in more and more of his cock. I soon found I could get about 5 inches or so until the head reached the back of my throat. Up until this point, I really hadn't thought about what I was doing, other than trying to do what I thought would feel could so that I could get him off as quickly as possible.

It was at this point that I realized that I wanted to go further. I wanted to see if I could deep throat him all the way to the base. I took a breath and plunged. When the head hit the back of my throat, I had a little bit of a gag reflex but I pushed it past anyway. John let out a passionate, "Ohhh, yeah!"

When I brought my mouth back up to the head of his nice cock, I noticed it was coated with a thicker, more sticky saliva from the back of my throat. I licked and sucked at it to clean it off and plunged down on his shaft, picking up a fast, steady pace, about the same rhythm that I would jack off to or that one would fuck with. Each time I pulled up I made sure to drag my tongue along the underside of the shaft, creating enough pressure to heighten the sensation. I could tell it was working for John with all the moans he was making. By now he was bucking his hips into me, pushing his cock in my mouth and down my throat without much work on my part. He put his hands on the back of my head, pushing me down on his cock and said, "Do it! Suck it! Take it all!"

As I continued deep throating on every stroke I found his cock passed easily into my throat without any gagging sensation. I continued sucking with a frenzy a little longer when he moaned, "Oh, yeah, that's it. Make me come. I'm gonna come."

I hadn't thought about this part before, but realizing it now, I decided I didn't want him to come in my mouth. I started to pull my mouth off his cock, but he pushed me back onto it and said, "I'm gonna come in your mouth. Suck it good. Make me come!"

With that he started pumping my mouth in short, fast strokes like it was a willing pussy. With his hands holding my head down, all I could do was take it. In what seemed like almost no time at all he suddenly said, "Oh yeah, here I come!"

Almost simultaneously I felt his cock pulse between my lips, followed by the first burst of warm come in my mouth and on my tongue. "Ahhhh, ahhhh, ahhhh," he grunted with each shot of come he released in my mouth. Instinctively, I began swallowing it as it filled my mouth. I got a little taste of it and actually didn't mind it. I could hardly believe I had just given my first blow job and tasted come for the first time.

He relaxed and collapsed his hips back down to the bed. I pulled my mouth off his softening cock, giving a final suck to get any remaining come out of his dick and off his shaft. "That was real nice," he said. "I'm going to enjoy this repayment plan."

"I didn't know you were going to come in my mouth," I said.

"What's a blow job if you don't come?" he replied. "I'll see you tomorrow, same time."

I left, replaying the events in my head over and over as I walked home. I decided that I was probably going to enjoy the repayment plan as much as John was.