I was fifteen and the other kid was about 13. I don't even remember his name but he looked much like the kid in the movie "The Slingshot," in which the leading boy receives a bare-bottomed beating with a ruler for making slingshots out of condoms (which there and then were against the law). This boy had light-brown hair and green eyes. He had a little baby fat left but he carried it well and no one would have teased him for being fat. He was white but had a good tan. We were playing pool and were the only ones in the room at the time.
He fancied himself to be a pretty good player. This wasn't a hustle; myself, I was just an average player. If the truth be known, the bet could have gone either way. This was the only boy who really had the opportunity to spank me under less than controlled circumstances, but it just seems to be my destiny that I should be the spanker.
Anyway, I can't remember whether we played a game or not before I decided to make him a wager, but I decided that I would challenge him.
"Hey, want to make a bet," I probed.
"I can't," the boy said, "I haven't got any money."
To which I replied, "That's okay. Money isn't the only thing for which we can bet."
"What else is there?" the boy asked quizically.
As if I was thinking out loud (when I was really plotting my strategy), "Well, we could bet for push-ups [but neither of us was very athletic] or slugs in the arm."
"No," he said, "I don't want to do that."
"Yeah," sounding somewhat disappointed I responded, "Me, neither."
Then, as if a great idea had just come to me, "Hey! I know: we can put our butts on the line like they do at fraternities. We'll play for swats! What about that? If you win, you get to give me 25 swats on your own terms; if I win, I get to do the same to you."
Looking really unsure of himself, but he was kicking it around, "Well...."
"Come on.... Sure, the licks will hurt, but we both have a fair chance at winning. Let's do that!" I prodded enthusiastically.
Now, who knows what makes a kid except such a stupid bet, but "okay" is what he said, and the bet was on.
I don't remember how the games went, so I won't waste your time with annoying scenery. I do seem to remember that he had just about won the first game (which had my mind in an uproar), but he scratched on the eight ball, and so I won.
"Okay," I said, "You can take the 25 licks now, or we can play for double or nothing."
There was no slowness in his response time, "Double or nothing," he quickly said.
He lost that game, too, and was now at 50 licks. I was fast becoming aroused. As we had been playing, I would carefully follow him around and watch his backside as he bent over in all those different positions to take his shots. By this time, I had a good idea of what his butt looked like under those cords he was wearing: He didn't have what I would call a bubble butt, but the definition was there. I could see where the back stopped, legs started, and where his bottom was in the middle. It was about 7x6", and my hand span was about 5 1/2 at the time, so it would be a nice fit. He was still young enough and I could tell from the rest of his appearance that there would be no hair present, only a semi-firmly rounded bottom with a nice tan line at top and bottom. Yes, I was getting very excited.
I don't remember exactly how the next deal came about but I think we played another two games. He lost the first three but won the last and, at this point, I was at an advantage enough to knock off 25 of his and spare myself. It was now time for the boy to learn his fate.
The boy was looking rather despondent but he knew what was coming. He made a bet and he was going all the way.
"Okay," with firmness I began, "That's 75 licks. We agreed the licks would be on my terms if I won, remember?"
"Yes," but just go easy, okay?" He pleaded.
Making it clear I was in control now, "No. Licks are intended to hurt. You will receive 75 licks with your pants down..."
At this his eyes shot up and he was looking scared, but I continued.
"With your pants AND underwear down, on your bare bottom, with a paddle of some sort," I finished adding, "Is that clear?"
It was clear the boy objected and he was still kicking the idea around when I said, "Or, I can just kick your ass now. You made a bet and you will keep it one way or another, is that clear?"
Clearly defeated and overpowered he mumbled, "Yes."
"Let's go, then. I can't give you the licks here: people will hear. The gas station on the corner has a detached restroom, we will go in there, and find our paddle along the way." I further assumed the lead by approaching the boy and just kind of playfully wrapping my arm around his shoulder, and with an element of fun in my voice and tousling his hair, "Come on," and I led him out of the Y.
The walk wasn't very long. I told him to keep an eye out for an object we could use as a paddle. Amazingly, he did just that!
"Here," he said, and he handed me a piece of wood someone had discarded in the alley behind the station. The board was slightly more than 1/4" thick and about 3 1/2 - 4' long and was well sanded; it's thinness gave it just the right strength for good swats and yet it was still flexible enough that it could be popped much like a switch. It was perfect!
"Are you sure this is what you want?" I asked. Then, I added frankly, "You know it's going to sting."
"I don't care," he said, "Let's just get this over with."
That was good enough for me. For the rest of the way we walked in silence, and he perhaps a little slower, which was fine because along the way I was practice swinging which I am sure was adding to his discomfort. Finally, we arrived and finding the restroom unoccupied, we went inside and locked the one person stall.
I didn't waste any time, the moment we were inside and the door was secure (I let him go in first), "Okay, drop trou," I commanded. Slowly, which was fine with me, the boy did as he was told {even if it was with a look of disbelief in his eyes).
As is expected, when the boy looked me again in the eye to indicate his readiness, his pants and briefs were just barely down and still covering half his bottom. His shirt covered the rest.
"No," I said, "I am going to sit down and I want you to stand in front of me facing away." Grudgingly, the boy complied. Now, I could see if I had estimated correctly. Slowly, I raised the shirt and stared briefly. Then, without hesitation, I gently lowered his pants the rest of the way and, finally, his briefs.
The boy was really quite lithe. He had good firm legs and his butt was nice and firm also.
"Okay," I said, "You will now bend over and place your hands on the wall in front, and I mean BEND over. I want that butt sticking out."
Quietly, the boy bent over. I raised his shirt, and was liking his butt more every minute. The definition and padding was definitely there. I stood to the left of the boy and raised his shirt, fully exposing his bottom. The boy was very submissive indeed.
I gave my final instructions, "I don't expect you to count, but you must stand still. Any lack of cooperation will result in the paddling stopping long enough for me to lay you across my knee, blister you with my hand, and stand you up again for the paddling to begin all over again."
Not waiting for an answer, I brought the paddle back sufficiently enough to give it a good flick... SMACK! It landed dead center and its marking was clear: a nice red stripe developed. "SSSSSS," the boy breathed in, shifted his feet and braced himself for the next lick. SMACK! This time there was no movement on his part, the boy just stood his ground, but his bottom began to swell for the lick had landed in the same place.
CRACK! CRACK! Over and over again the board fell. The boy was taking it far better than his bottom indicated he should; I concluded he was not a stranger to harsh discipline. I thought I would have liked for us to become friends if I had not just been there for a visit. SMACK! The paddle was leaving angry red marks but still very safe. Every now and then the boy would brace himself again and show faint reaction, but no tears. Finally, it was over.
"Okay, that's it for the paddle," I said.
***The boy really took all 100 swats and never cried. The rest is pure fiction; it is the way I would have liked the story to end.***
The boy was reaching but before he could pull up his pants, "Wait a minute," I said. The boy froze and came to a standing position, looking me in the eye with almost a loathing...waiting.
"Now, you took your swats very well," I continued, "But there was movement against which I warned you. I know the middle of your bottom is quite sore, but as punishment for your movement I will now spank the rest of your bottom. Stand your ground."
Clearly he was not happy, but his show of bravado would certainly be diminished if he were to resist now. Without any further instruction the boy turned and faced the wall. Repositioning himself, he bent over, and with the other hand raised his shirt for me. That was good enough for me.
If he was determined to be silent, there would be no show of mercy. I wrapped my left arm around his face and made him bend over more, almost lifting him off the floor. Then, with my right hand, I began: SMACK! SMACK!
Spanking all the places the paddle hadn't touched. Reddening the top right, then the left, the bottom left, then right. SMACK! SMACK! SMACK! The right side: SMACK! Left: SMACK! Back and forth, up and down. The boy, noticeably sore, began to fidget.
By this time, his bottom was completely covered in red. Quietly, at first, the boy began to tremble and then to cry. I continued spanking him and now his bottom was bluing in the places where my hand overlapped the paddle weals. SMACK!
Though stammering, "I-I'm s-ss-s-sorrr-ry. I don't know what I did to deserve this , bb-b-ut plpleease stop."
Unheeding, I continued smacking his bottom for a few seconds. The boy was thoroughly broken and had gone limp, excepting every swat gracefully, but crying.
Finally, I let go of his waist, but the boy just stood there crying.
I sat down again and watched him shiver with cries. His reddened bottom trembling. Gently, I pulled up his briefs, and watched his reddened bottom become engulfed in white. Turning him to me, I raised up his jeans, which he fastened. He stood there crying, and I gently sat him on my lap and held him. He hugged me in return. I couldn't believe it.
"Are you okay?" I asked.
Wiping the tears away and with humility he nodded his head, and then asked, "Why did you spank me so hard though?"
"You made the bet," was my only answer.
***Back to reality***
I never saw the boy again. We each went our separate ways, but he has rarely left my mind since.