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The Bookie Ch. 01

By: tmh10



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.

The Bookie Ch. 02



The next day as I walked to John's house I began to imagine the events that would soon unfold. I had visions of his hard cock thrusting into my mouth as I made every attempt to take it all in. I replayed in my head different techniques that I would try--things I imagined would enjoy having done to me. As I arrived at his door, I realized I had a raging hard-on myself. I had gotten really aroused fantasizing about sucking his cock again.

John answered the door and let me in. I quickly noticed he had a friend over. This was a friend who must have dropped by and didn't realize John had other plans already.

"This is Jeff, my betting connection," John said. Seeing the confused look on my face, he continued, "Jeff wanted to know why I was not able to pay him in full, since I've never been late. I told him the story and he decided he wanted to come and see for himself."

"I thought we were going to keep this just between us," I said.

"Don't worry, Jeff will be cool about it. He just wants to watch. I told him that was cool with me." John paused for a moment to size up my response and then continued, "I'm ready to get started. I've been horny all day, looking forward to this."

With that, he got up and headed toward his room. As he reached me on his way, he grabbed my hand by the wrist and gave me a gentle pull to encourage me to come along. Jeff followed us into the room.

"Lie down on the bed," John commanded. I got on the bed, lying on my back with my head on a couple of pillows. Jeff climbed on the bed and straddled his legs over me, scooting his way up until he was close to my face. "Unzip my pants and take my cock out," he again ordered.

I reached for his jeans and after unbuttoning and unzipping them I pulled them down close to his knees, about as far as they would go since they were stretched by his legs being spread apart. He had no underwear on and his dick was already pretty hard. His pushed his hips forward, moving his cock toward my mouth and said, "Now suck it."

I moved my head forward to meet his arriving cock head and opened my mouth to take in the head. The skin was soft and it was pleasurable to have this nice dick in my mouth. I began stroking my tongue on the underside of his cock, just below the head where it's very sensitive. John moaned and responded by pushing his tool further into my mouth. I reached up with my hands and grabbed his ass cheeks with each one, partly to hold on and partly to encourage him to fuck my mouth.

I began pushing his ass toward my mouth, but it only took a couple of times before John realized what I was signaling. John know began the thrusting, pushing his cock all the way into my mouth, until my lips just about reached the base of his shaft. My throat was a little unprepared to meet the head of his shaft and I had a slight gag reflex, but I instinctively managed to relax and allow his cock all the way in.

John began to pick up his rhythm and started to fuck my mouth rather furiously, like it was his best pussy. I tried to do my part, sucking and tonguing the best I could, but he was in control now.

Then John grabbed the back of my head with his hands and thrust my head forward into his pelvis. He held it there for a second or two and pushed my head back again, only to push me onto his cock again. He began to moan loudly each time he did this. I could tell he was about to come. I pushed my tongue into his cock to tighten the friction as he fucked my face.

This sent him over the top, as he cried out, "Oh, yeah!" and began a series of short, quick half-thrusts into my mouth. I felt his warm cum shoot into my mouth, landing on my tongue and into my throat. With each thrust that followed he unloaded stream after stream of cum, probably about eight or ten shots. I sucked and swallowed as much as I could to keep up, savoring the taste.

John pulled out and climbed off me to lay on the bed next to me. "Oh, yeah, that was great, even better than yesterday," he said, rather exhaustedly.

"That was hot," Jeff said, reminding me that he was there, too. In all my attention that I had given to John's cock, I had just about forgotten he was there. "That got me pretty turned on. Do you think I could get a blowjob, too?" he asked.

Before I could answer, John answered for me. "Go ahead, I don't mind, I'm spent." Truth be told, I might have feigned an objection, but inside I was willing to suck another cock, even if I was starting to become a blowjob slut.

Jeff took his pants off and assumed the same position that John had just minutes before. I started more slowly with his cock, giving good attention to it, licking up and down the shaft to get it nice and lubricated with my saliva. I took just the head into my mouth and worked my tongue up and down the shaft area just around the head. I then alternated by turning my head sideways so that I could run my tongue all the way down his shaft from the head to the base without actually putting his cock in my mouth. 

Jeff's cock responded by hardening to it's full stiffness, probably some seven inches and nearly as thick as a toilet paper tube. His cock was circumcised and quite nice looking as well. I moved back to take his dick into my mouth again and Jeff responded by pushing his hips forward, meeting my thrusts with his own. However, his pace was slow and methodic, as it seemed he wanted to enjoy each penetration into my warm mouth. I responded by paying extra attention with my tongue, swirling it around his thick shaft.

His cock was about all I could take in thickness, as I nearly had to stretch my mouth open wide to fit it in. This was certainly no concern of Jeff as with each thrust he pushed his way further into my mouth, eventually meeting my lips with the base of his shaft. His strokes were such a slow pace that I had to take care to relax my throat not to gag on his large member. He moaned with each push into the warm, moist opening I offered him.

After a bit I noticed he started to pick up the pace. His thrusting became more eager when he said, "Oh, yeah, suck my cock. Make me cum. I want you to take all of my cum!" I moaned at hearing that, my voice acting like a vibrator for his tool pushing and thrusting it's way into my mouth and throat. In a moment, I heard him say, "Oh, yeahhhh," timed simultaneously with the first shot of his man-load into my mouth. I eagerly tasted it to compare with John's.

With each thrust more and more of his load came into my mouth. I'm sure it wasn't that much, but it seemed like a huge load. I had to swallow several times to keep up with the flow he offered. His tasted different than John's, not really better or worse. I liked them both.

Jeff pulled out and fell back on the bed, spent and satisfied. "Man, that was great," he said. "I could go for that every day."

"If it will pay back my debt faster, I don't mind at all," I said. Truth be told, I probably would have been willing to service him anyway.

"I guess we'll both see you tomorrow," Jeff said.