The Romance of Chastisement

The Romance of Chastisement

Friday, June 29, 2012

The Great Cheerleader Bet Pt 1

By the time you get to your 10th high school reunion, the memory of those days is so clouded with nostalgia that you forget just how hard being an adolescent was. Was high school really all that great? Parts of it were, but other parts were downright painful and humiliating. But even here memory begins to play tricks. We relive the glories and discount the losses. And then there are those things that might have been----those are the worst, I think. The lost opportunities. But you know, sometimes, just sometimes, life tosses you a second chance.


When I walked into our 10th, to my great surprise there was Lynne Todd. Lynne "the bod" Todd, as we called her in those days. She of the beautiful eyes, lightly freckled face, long blonde streaked hair and that voluptuous, but ever so firm, body. Lynne had featured prominently the testosterone fueled fantasies of many a teenage boy in the late '90's. Only Lynne didn't go to Bedford, my school. She went to our neighboring rival school, Glenview. Both schools were in the same part of town and lots of kids in both high schools knew each other from grade schools. Lynne had been a cheerleader at Glenview and everyone knew her. And boy did she still look great. Ten years later and she still had all those fabulous curves.

So what was she doing at a Bedford reunion? My answer was supplied by Mandy Hollister, a fellow former cheerleader on the Bedford squad. That's right, I was a cheerleader. Me, a guy. You don't think it takes athletic ability to be a cheerleader? Let me tell you, the tumbling, the pyramid stunts, the running flips---you are a gymnast really. I was no jock in the football sense, and not tall enough to play basketball, but gymnastics I could do. And so I became a cheerleader. Both squads had guys as part of the rally team.

Mandy saw me and waved excitedly, motioning for me to come over.
"Danny, look who I brought to crash the reunion," she chirped.

"Hello, Danny," said Lynne, batting those famous eyelashes. "Long time."

"Yeah, Lynne, long time. How have you been?" Everybody had wondered. Here's what I knew about Lynne. She had graduated, gone to college somewhere out of state, and had married. That was it.

"I'm back in town now. Tom and I divorced. So I'm just here again and well...that's about it. I work in real estate now. Sales. How are you?"

Divorced already. Interesting. "Good. Fine. I, uh, never married. I'm partnered with a couple of guys now-we developed this software. It's a long boring story you don't want to hear."

She smiled warmly and touched my arm. "Oh, but I do."

"Well then, wait here and I'll get us some drinks." I sallied forth in search of the bar.


It gave me time to think. Lynne Todd. Wow. We had some history, Lynne and I. Not what you think, but interesting. Her touch brought back memories. As I said, we were both cheerleaders, but on the squads of rival teams. And the rivalry was fierce. Our senior year we had been butting heads with Glenview in everything. The football teams played for the city championship. We won. That got Glenview riled up. Then basketball season started. We were both contenders for the state title and on a collision course. It was coming to a head in those last few days of the state tournament.
Of course, we each fiercely wanted to win, and the rivalry escalated. Wherever kids congregated, the insults and taunts would fly. The cheer squads were involved too. We even had our own competitions.

It was at one of these meets that Anita Worthington, Glenview's captain proposed The Bet. She was one ego driven supercilious bitch as far as I was concerned, and part of the reason we agreed to The Bet was to see her taken down a peg or two. A regal princess, she was living large on daddy's money and completely stuck on herself.

 The idea was simple. We each wagered that our team would win the state basketball championship. The entire losers' cheerleading squad would pay a forfeit. After the game both cheer squads along with a few friends agreed to meet at Long Lake, a popular hangout. We'd have a bonfire and the guys would score some beer. During the after-game party the winners would collect on the bet, ---unless the losers chickened out.

I remember that encounter like it was yesterday. We were back in the waiting room after our routine. The Glenview squad strolled in. We stared daggers at each other for a while, then miss bitch herself, Anita said, "We're going to kick your asses at state." To which several kids replied, "Bullshit!" After several minutes of heated debate, Anita said, "Care to put your money where your mouth is?" And we said sure, what's the bet?

Anita smirked and said boldly, " A paddling. Losers bend over and take swats. Standard school paddle. Two swats for every point you lose by."

We were just dumbfounded for a minute. What? Paddle swats?

Anita took our confusion for reluctance, I'm sure. "What's the matter? Chicken?" All the time with this arrogant smirk. She turned to her squad. "See? I told you. No guts at all."

Then I think it was Nicki Leeds on our team, a real red-haired fireball who said, "Chicken are we? Bring it on!" She made a beckoning gesture with her arm. Our heads were nodding. Then Nicki said, upping the ante, "Let's make it really interesting. The swats will be bare butt." She let that sit for a moment. There was dead silence. "Well? Now who's going to be chicken?"

And that, my friends, is how these things escalate.

 So in the end it was agreed. The bet was that losers would take swats with a standard school paddle, two swats for every point that was the margin of victory. Bare butt. We'd put names in a hat for a blind draw. The only stipulation was that paddle wielding would be by girls only. The girls thought the guys were much too strong and it was therefore "unfair". Whatever. At least I would get to watch that conceited princess get her bare ass smacked. I didn't relish the idea of watching guys paddle guys anyway. So we made The Bet.

The night of the big game came and, believe me, we were wired with nervous energy-about the game, about the after game festivities, about the bet. The mood was electric. The game was close. The lead changed several times. Our hopes rose and fell. We screamed and did our thing but it wasn't enough. At the end of the game Bedford had lost, 55-49. We all looked at each other at the final buzzer completely chagrinned, and I know we all had the same sinking feeling. We did the math. It meant 12 swats with a wooden paddle on our bare butts.

Still, we vowed not to chicken out. We'd have never lived it down. School honor was at stake. So later we made our way to Long Lake. It had been an afternoon game in another city and so several of us on both squads had to sneak off the team bus catch rides, which made for an interesting side story, but more about that later.


We were a pretty sullen crew when we showed up at Long Lake. The fire was going, the beer was flowing and the Glenview squad was whooping it up. They had mostly girls on the squad, only two guys, so two of theirs would do double duty. We stood around and drank. We poured down the beer and somebody had some whiskey so we drank that too.  Dutch courage, I guess. All of this was accompanied by much jocularity from Glenview. The kidding was non-stop. Things like: "I wouldn't stand with my back to the fire if I were you. Pretty soon those buns will be toasty enough." And, "Hope you brought a soft pillow for the ride home." That kind of stuff.

But I decided to make the best of a bad situation. I started to chat up Lynne. I'd known Lynne in elementary school and we'd been classmates. We'd even done the boyfriend-girlfriend thing. An eighth grade romance. Dance parties in the basement with the lights off, couples clinching tightly, spin the bottle---that kind of stuff. She hadn't been beautiful then, that had come later. And when she had bloomed into a raving beauty, she'd been at Glenview and had been immediately snatched up by the jock du jour. So I had lost track of her except when our teams played each other.

To my delight, I found I still liked her, and I think she liked me too. That old spark was still there. She had dumped the current jock, but it didn't matter, we were all about to graduate soon. Then she started kidding me. "I hope I draw you, Danny. You always had such cute little buns, I'd love to just smack them." To which I said, peering around at her luscious backside, "You're not so bad yourself, Lynne. And you could probably use a good spanking." And she could. Couple that playfully teasing personality of hers with the most prominent, roundest ass that ever wiggled, and you might as well have an engraved invitation. To see her in tight jeans would give you a boner that wouldn't quit. Her tiny waist flared into curvy hips and those two luscious perfectly rounded bottom cheeks.

She giggled that I would not get that chance tonight.

Well it went on for a while and then their captain, Anita Worthington, announced, "All right, kids. Forfeit time. Time to pay up on our little bet." It was all in that smarmy sing-song voice. I wanted to strangle her. She pulled out a sheet of paper and tore it into strips. We all wrote our names on the paper and put them into a hat. Then one by one the members of the cheerleading squad, twelve in all, came up and drew names. They were all looking over at us and giggling and laughing as they drew the names.

It was going to be one at a time. I think it was Mandy Hollister who went first. Her "spanker" was Jenny Carlton. They knew each other too. Jenny was grinning from ear to ear as Mandy came forward. She had the paddle in her hand and was gleefully practicing, swooshing it around. Somebody had borrowed one from an older sister who had been in a sorority. Everybody formed a big circle next to the bonfire. All the chatter stopped.

Mandy is a cute compact little pony-tailed pixie. Jenny told her to slip down her panties and "bend over, girl". Well this was the moment of truth. Up to now it had been all bravado. Mandy nervously slipped her hands under her cheerleader skirt (we were all still in uniform) and the next thing we saw were Mandy's panties at her ankles. She bent over with her hands on her knees and pushed her bottom out cutely. There was a hushed silence as Jenny raised the little cheerleader skirt. The unveiling revealed two deliciously rounded globes that stuck out pertly. She posed as if requesting application of the paddle. Well, Jenny was going to oblige. "What was the score, Mandy?" she teased.

 Mandy huffed, "You know very well what the score was."

Jenny might have teased her some more, but instead she just pressed the paddle to Mandy's bottom, marking the spot. She drew back and brought her arm around in a wide arc. The paddle landed with a sharp whack! Mandy yelled "ouch!" Jenny drew back again. Smack! The swat rang out in the still night. Mandy yelped. Ten more times Jenny spanked Mandy's bottom with that paddle. Mandy tried to maintain her position and not yelp too loudly. Every smack made Mandy's tight little bottom cheeks dance. Now this was creating a problem I had not anticipated. I was sporting a raging boner. I had to watch several of my very attractive teammates come forward and get their bare bottoms swatted by the Glenview cheerleaders, so you can imagine.

There was Allison, a cute slender blonde with straight hair. She slipped her panties to mid thigh and bent over, proudly sticking her curvaceous ass out. Her very prominent bottom wobbled with the impact of the paddle swats planted there by Cathy Regen, one of the taller, more athletic Glenview cheerleaders. It looked like Xena paddling Gabrielle.

Michele Harris a medium height brunette was the most vocal. Each swat provoked a loud "Yow!" ---much to the delight of the Glenview squad.

Nicki, our red haired, wisecracking dynamo got her paddling from Anita herself who laid them on slowly, milking it for every last bit of drama. Nicki did her best to endure the paddling bravely. With each paddle smack, Nicki's knees buckled or she half straightened, only to be reminded by Anita to bend back over and stick out her cute little bottom for the next lick. That cute bottom did quite a dance under Anita's paddle and by the time she was finished Nicki was struggling to hold back tears.

Finally it was my turn. I looked over to see who my paddler would be. And holding the paddle and beckoning me to step forward was none other than Lynne Todd. Lynne said, "Ok Danny, take 'em down. Let's see what you got, you bad boy." All the girls giggled. I was blushing like crazy, but you couldn't see it. It was dark and the only light was the bonfire. Still, I tried to scrunch down and hide my erection. Excited giggling told me I was less than successful.

Lynne lined up that paddle on my backside and tapped it a couple of times. "Ready?" she said. I just nodded. She reared back and the next thing I felt was the shock of a hard swat and the burn that it generated. And I thought, yow! That really stings. But then came another. And another. Each time the sting got hotter and hotter. It was more of an ordeal than I had imagined. I was hissing through my teeth. The swats kept coming . Crack!....pause. Tap..tap...crack!....pause. Just like that. It was burning ferociously. And I remember thinking, good God that girl can hit hard. My sweet, deliciously hot friend, Lynne. She was paddling me just as hard as the vice principal in a bad temper. I was struggling not to yelp like a baby. Maybe that was ok for the girls, but not for me.

But I got through it. All twelve searing swats. I think I was blinking back tears as I pulled my pants back up. I had to go get a beer. I was nursing my blazing ass and glugging down beer when to my surprise Lynne sidled up to me. Was I ok? She asked. I told her she hit pretty damn hard and she said she was sorry. She said we could go somewhere if I wanted. She had a blanket. Now I had to wonder what this was about, but I wasn't going to look a gift horse in the mouth, so off we went. The forfeit swats were done by now and everybody was back to drinking, or in many cases, drifting off in pairs. I mean it had been quite sexy to watch pretty girls get their bare asses paddled, so it wasn't surprising that a few couples were pretty randy.

So Lynne and I parked the blanket somewhere secluded and I managed to sit down, wincing all the while. She cooed and apologized and said she got a little carried away and could I forgive her? Well one thing led to another and before you know it, I was making out with Lynne. We were pressed up against each other lying on our sides. It was going hot and heavy. I got my hand under her sweater and I was feeling those wondrously large and firm breasts. I was pinching her nipples and with another hand I was feeling her jouncy ass cheeks. I slipped my hand under her panties and found her sex wet and slippery. She moaned softly as I stroked her there. I think we were about to go all the way when somebody shouted "cops are coming!" and put an abrupt end to our make-out session.

We all scattered, jumping in our cars and peeling out of the Long Lake campground. In all the confusion I lost Lynne. We never connected again for various reasons, having mainly to do with a boyfriend reconciliation, conflicting schedules and this and that. By summer she was gone. All the college years and beyond, I hadn't seen her. Until now.

To be continued.....


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