Betting on Monopoly


by Bakerboy <Bakerboy17@hotmail.com>

Jeff and I had been best friends since he moved across the street at the beginning of third grade. We spent most of our free time together during the school year and almost all of our summer vacations. Of course we played all of the normal sports. Baseball, football, soccer, and basketball, when we could scare up a group of the neighbors for a pick up game. But, most of our activities revolved around the two skateboards we drug around with us. The skateboards eventually led us to the most exciting and frightening episode of our short fourteen years.

My 120 pounds fit nicely over my 5-foot 6 inch frame which would come in handy later when I tried out for the high school swim team. I guess I was tall and thin for my age. Even though he was a full two inches shorter than me, Jeff outweighed me by at least 10 pounds. He'd get really mad when I'd tell him that I was the brain of our dynamic duo and he was the brawn.

I discovered the secret ways a boy could pleasure himself when I was eleven and practically wore the _d_a_m_n_ed thing out over the next few years. During my sessions I fantasized a lot about Jeff or another of my male friends but I never dreamed that I might be gay. Of course, I didn't really know what that was either. By the time I got to the eleventh grade I had accepted my _s_e_x_uality and was trying to score with every guy in school. Still, at eleven, I wasn't about to tell anyone about what I did by myself.

Right before my thirteenth birthday, Jeff was staying over night at my house and told me that he "did it." After much prodding on his part, I finally admitted that I did "it" too and he promptly suggested that we do "it" together. At first I was really scared about it but from then on, he and I did "it" together every chance we had.

I don't remember when exactly it was that I started fantasizing about us spanking each other. But, I developed an intense interest in anything to do with corporal punishment. Now, I was never spanked at home and never saw anyone get a spanking but it would sure charge my motor when I thought about it. Over time I began to think that Jeff was also into it. After all, he was always saying some sports team "spanked" the other team and I finally decided to gently probe and see if I was right.

One day Jeff and I were at his house watching a basketball game on television. Since I'm not really into sports, I couldn't tell you who the two teams were. But, one of the teams was badly losing by twenty points and Jeff started saying that they were getting spanked. When the game was over, he suggested that we play monopoly. While setting up the game, he started saying that he was going to beat me and that I didn't have a chance of winning. Needless to say I bantered back and announced that I was going to "spank" him at monopoly.

Suddenly, he looked at me and said, "We'll see who gets spanked."

That was a curious statement, but I wasn't about to let it go without a retort. "Want to bet on it?"

"What do you want to bet?" he asked.

"How about the looser pays the winner five bucks?" I suggested, knowing that neither of us had more than twenty-five cents to our names.

"You don't have any money," he said.

"OK," I said. "What do you suggest we bet?"

"Well," he started. "There is one thing we could bet, if you're not too chicken."

"I'm not chicken," I insisted. "I can bet anything you can come up with."

"How about the winner spanks the looser?" he asked, pausing long enough from the game to look up at me.

"What do you mean?" I asked, wanting to make certain I'd heard him correctly.

"Whoever loses the game has to lay across the winners knees and take a spanking on the bare bottom," he explained.

"Are you serious?" I said, not believing what he was saying.

"Absolutely," he replied. "I'll do it if you will."

"I don't know, Jeff," I said. "How many swats would we bet?"

"Let's make it interesting," he said with a grin. "How about one hundred."

"A hundred swats!" I gasped, my mouth falling open.

"Are you too chicken?" he asked.

"I'm not chicken," I again insisted. "How would we do it?"

"The winner decides everything," he said. "You in?"

"A hundred swats, on the bare bottom, anyway the winner wants to do it?" I asked, to clarify the terms of the bet.

"That's right," he said. "We'll play one hour and whoever has the most money left at that time will win the game and the looser has to take the spanking right then."

I hesitated for a moment not knowing what to say. If I lost, I knew Jeff would really spank me hard. He wasn't the type to do anything half way. Of course, if I won, I'd get to play out one of my fantasies and the idea of having Jeff across my knee was very exciting. The odds of my winning were pretty even, I thought, so, I said, "You're on."

This evil little grin spread across Jeff's face. "Good," he said. "It's a bet."

We shook hands and finished setting up the game.

Both of us took the game seriously. Neither of us wanted to be on the losing end and have to take the spanking. But, I must admit that I was aroused by the prospect of spanking Jeff and I struggled to keep my hard _c_o_c_k_ hidden from his view as we played. Several times I thought I saw a distinct bulge in his baggy jeans as he rolled the dice and I wondered if he was as excited as I was. This was going to be fun!

I knew the game was going to be close. They were every time we played. But, as the clock wore on, my excitement grew. I started getting this hollow feeling in the pit of my stomach and my bottom started tingling. My palms were sweaty and my heart raced in my chest. Somehow, deep down inside, I realized that I really didn't want to win. I wanted to be the one across Jeff's knees feeling his hand on my bare skin. My excitement overcame my fear of the spanking itself and I started teasing Jeff about "beating his butt."

Once Jeff landed on my property and had to pay rent with two houses on it, his demeanor changed. He started to get worried that he might lose the game. I knew that he had no intention of letting me spank him, even if he lost, I'd bet with him before. Predictably, he started trying to wiggle his way out of the bet.

"Want to call off the bet?" he suggested, trying to make it sound like he was doing it for my benefit.

"Nah," I answered. "It's OK." There was no way I was going to let him squirm out of it so soon. If he lost, I'd let him off, of course. But I wanted him to sweat first.

"Are you sure?" he probed. "That spanking is really going to hurt."

"It'll hurt you just as much," I said, giving him my evil little smile.

Things were starting to wind down with the game and it looked like I was going to win. Jeff only had a small amount of money left and he still had all my expensive properties coming up. Watching his reaction to the situation was actually a lot of fun. At one point he even started to chew on his finger nails, something that he usually only did when he was under extreme stress. What really got me about it was that he never paid off his bets anyway, so I didn't understand all the nervousness. He wouldn't go through with the spanking and both of us knew it. Normally, he would win and I'd have to pay the bet. Which I always did. It was a matter of honor with me and something I'd been brought up to do. Still, it was fun watching him squirm.

With only five minutes left in the game, he really started whining about the bet. Almost pleading with me to change it. But I was having fun and had no intention of letting him out of it before he actually lost the game. I suppose, looking back on it, that I shouldn't have been so _c_o_c_k_y about it. My teasing got a little out of hand and I almost had him in tears by the time the game ended. Unfortunately, with my last turn I rolled a twelve and landed on Park Place. Jeff had built hotels on it and I had a very large rent bill to pay. When we counted the money we had left, I was $114 short. He beat me on the last role of the dice.

Now the situation was reversed and he was in a state of euphoria. For some strange reason, I'd secretly wanted to lose. But, with the spanking staring me in the face, my desire waned considerably and I suddenly wanted out of the bet. Jeff just laughed when I suggested he take pity on me and cancel the wager.

"No way," he insisted. "You lost fair and square."

"Come on, Jeff," I pleaded. "I'd have let you off the hook."

"Bull," he said. "When it looked like I was going to lose you were singing a different tune."

"I was just giving you a hard time," I explained. "You know I'd let you off."

"Sure, sure," he said. The evil little grin returning to his face. "I'll just bet you would."

"I would have, honest I would," I whined, trying to convince him.

"Too bad," he said. "You're getting a spanking anyway." "Come over here."

Here is where my upbringing causes me problems. I've been taught that weaseling on a bet was the worst thing a guy could do. There was no alternative, I had to honor the bet. Slowly, I stood and faced him. All at the same time I was scared and excited. In one way I was looking forward to the next few minutes and in another I loathed what was going to happen. The best thing, I thought, was to just get it over with as soon as possible. Sheepishly, I asked, "What do you want me to do?"

"Take the pants all the way off," he ordered, motioning with his finger for added emphasis.

I silently complied. Within seconds I was standing there dressed only in my socks, briefs, and T-shirt.

"The shirt, too," he demanded firmly.

Once my shirt was laying on the floor, I just looked down at him and waited silently for further instructions. A feeling of panic came over me and I had this irresistible urge to touch my butt, which had started tingling slightly in anticipation of the event. Only the feeling that had developed in the pit of my stomach and the urgent need to suppress a sensation of sudden illness kept me from actually rubbing it.

"OK," he said, firmly. "Let's get this over with." "Come here."

Without having to be told, I lowered myself across his outstretched legs and tried to get comfortable. My hands were actually shaking as I put them on the floor to support myself. Without warning Jeff slipped his hands under the elastic of my briefs and slid them down to my knee's leaving me totally bare.

"One hundred swats," he announced. "Anyway I want to do it."

"Take it easy on me, Jeff," I pleaded, knowing that he wouldn't.

Reaching down, he picked up his rubber soled gym shoe and gave me a few little taps on the butt, and said, "I'll bet this will really hurt, huh?"

"Of course it will hurt," I agreed, shifting uneasily on his lap.

"Are you ready?" he asked.

"I guess," I managed to say, bracing myself for what was to come.

WHACK, SMACK, SLAP

They came so fast that I didn't have time to react to the first swat before the next one landed. The explosion of pain surged through my body and found my brain a millisecond later.

"Ahhhhhh!"

SMACK, SMACK, WHACK

"Noooooo!"

Jeff wasn't playing around. He was making this the real thing and I suddenly started to panic. There was no way I could take one hundred of these.

SMACK

"Stop Jeff," I yelled.

WHACK

"I can't take it,"

SMACK

"NO MORE!"

Jeff simply ignored my screaming and continued to bring that shoe down onto my bare ass. I tried and tried to wriggle away from him. But, he held me tight. There was no way I was getting away from him. Again and again that shoe made contact with my bare skin. I yelled and screamed at him to stop. Finally, I collapsed and laid across his knee's and just sobbed, taking what ever he was going to give me. I hadn't bothered to keep count.

He stopped suddenly and let me lay there to cry it out. After a few moments, he gently started to massage my red, burning butt cheeks. "There, there," he cooed. "It's all over and you took it very well."

In some strange way It felt wonderful to be across his knee and having him caress my sore butt. It was like he was in control of me and I felt so safe that I almost didn't want to get up. An overwhelming feeling, or need, to please him and make him proud of me streamed through my brain. This new emotion confused me. I'd never experienced anything like it before and wasn't certain how to handle it. Still, I knew it was right for me to feel this way, no, I needed to feel this way. Right then, right there, I knew I'd be across Jeff's knee again taking whatever he thought I needed.

I was still sniffling when Jeff finally helped me to my feet.

"Did it really hurt that bad?" he asked, in a caring and concerned voice.

"It was bad," I answered, choking back more tears.

"Look what you did," he said, pointing to his jeans.

There on the front of his pant leg was a big wet spot, the remnants of an orgasm. At some point during the spanking I'd cum without being aware of it. Neither of us really understood what had happened, but, we knew it would again!


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