The Saga of Middleton

Back at Middleton High, Principal DuPree had discovered that, powerful as he was, there were a few very desirable asses that he hadn't been able to get his hands on.

One of them had been brought to his attention by his friend Dan Jacobs. Dan's next-door neighbor had an 18-year-old son at Middleton High -- named Matthew Cooper. Dan had tried every thing short of forcible abduction to get a look at this kid's body, but he was unbelievably shy and a total prude when it came to his body.

DuPree looked into the kid's records -- he was an exemplary student -- belonged to several academic organizations. In fact, he was currently student body president -- DuPree was amazed that he wasn't aware of him.

Checking him out, he discovered why -- the kid was a walking, talking prototype for the concept of "nerd." The thing is, now that Dan mentioned him, DuPree found himself taking a closer look. Actually, the kid looked to have a very hot body. While DuPree was observing him in the hallway, Matt dropped a pencil. When he bent over to pick it up, DuPree suddenly became a fan -- Christ, what an ass on this one!

And a closer look at the face indicated that behind the thick-lensed glasses and the lame haircut, Matthew Cooper was damned good-looking -- regular features, perfect nose, sensuous lips, long eyelashes. DuPree was amazed -- here was a treasure ripe for the plucking.

The principal decided to make use of his network of informants around the school. He decided on Spike. He was a good little actor and owed him a couple of favors.

And that's why, a few days later, during lunch period there was a sudden commotion in Principal DuPree's secretary's office. The principal heard it and smiled. Right on time.

A couple of minutes later, the door to his office opened and Miss Timmons entered, followed by two students -- Matthew and Spike. "Principal DuPree -- there was some kind of fight going on between these two in the lunchroom. Miss Grundy sent them in so you could sort it out."

DuPree smiled at her. "Thank you, Miss Timmons. That's fine. I'll handle it. Please hold my calls."

She turned and left the room, glaring at the two miscreants as she closed the door.

"Well, Matthew, I haven't seen you in here before. How about you giving me your side of things."

Matthew, who was clearly pretty pissed off, said, "Well, I was just sitting there, eating my lunch, when this... when Spike, here, just walked up to me and dumped a bowl of soup in my lap. Then he laughed and shoved my chair, so it tipped over backwards. I got soup all over. By the time I got up, Miss Grundy was there already and sent us up here. That's it."

Spike jumped in. "That's a lie! He came up to me when I was walking over to my table with a bowl of soup. He started calling me names and shoving me -- I don't know what his problem was -- he never said. He just kept yelling and shoving. Finally he knocked the soup out of my hands and it flew all over him. Then he slipped in it and ended up on the floor. I didn't do anything, and I still don't know what he was thinking about."

Matthew looked shocked. "But that's all lies! I didn't do anything like that!..."

The principal broke in, "OK, OK. Looks like there's a difference of opinion here about what happened. I'll get to the bottom of this.

"You, Spike. Get back to your classes. I'll talk to you later. Come back here at 4 and I'll deal with you then."

Spike smirked and walked out.

"And you, Cooper, I'm ashamed of you -- acting like a hooligan. What do you have to say for yourself?"

Matthew stammered -- he'd never been in this position before -- he almost felt guilty. "But, but sir. I really didn't do anything. It was all Spike. Really."

"There's no way of knowing now. I'm going to have to punish you both. Get those clothes off, now!"

Matthew looked shocked.

"Look, the rule book says I have to spank you bare-ass. Besides, your clothes are all soaked in soup. I'm going to have Miss Timmons take them over to home ec to get them washed and dried while you're being punished. Understand?"

Matthew nodded, still horrified.

"Now, strip, or I'll start adding spanks for every minute you take."

Matthew quickly pulled his sweater over his head and started on his shoes and socks.

DuPree beamed. At last! Some progress!

Every time he slowed down, DuPree threatened him with more, until finally he had the kid naked.

He looked great -- Dan was right. The kid had great legs -- muscular thighs setting off a great ass. Big dick, big pecs. DuPree couldn't believe he'd overlooked this one.

"Remove your glasses, too -- I don't want them falling off and breaking."

The boy almost protested at that, but finally took them off as well. Another hunch confirmed -- my God -- he was gorgeous.

DuPree rang for Miss Timmons, who entered almost immediately. He could see that even she -- old wooden-face, as they called her -- was impressed by what she saw.

Matt blushed deeply as he clasped his hands over his crotch.

"Matt! Pick up those clothes and hand them to Miss Timmons. Dorothy -- could you take Mr. Cooper's clothes to the home ec department and get them cleaned and back here as quickly as possible? They're all soaked with soup."

Matthew bobbed up and down, picking everything up, and gingerly brought it over to the lady, his big dick swinging as he moved. Miss Timmons sniffed in irritation and marched out of the office.

"OK, Cooper, get over here. Let's get this spanking out of the way, so I can get back to work."

He sat in the straight-backed spanking chair and motioned Matthew over his knee. He spent some time getting the teenager into position, moving him around, changing the position of his legs, getting his ass as high in the air as he could. Finally the kid's big cock and balls were pressed firmly into DuPree's right thigh and the principal's right hand started roaming over the smooth expanse of the kid's untouched asscheeks.

Suddenly -- Whacckk!! -- he landed a hard smack on Matthew's right cheek. The kid bounced and yelped in pain. It was quickly followed by another -- Smack!! And another -- Smack!! The pain was incredible. Matthew had had no idea a simple hand-spanking could hurt so much.

By the time he'd had 10 whacks, Matthew was begging. By 20, he was sobbing and squirming wildly over the principal's knee.

At this point, DuPree was having so much fun, it occurred to him to regret that Dan wasn't here to enjoy it, too. And just as he reached the halfway point -- 25 swats -- he had a bright idea.

He stopped, his hand clasping one of Matt's gorgeous young cheeks. He slid his open palm over the kid's sore, pink bare ass.

"Well, Matt, I'm going to have to stop for now. I've got a meeting I have to go to."

The teenager looked up at him, his bleary tear-filled eyes hopeful.

"But this spanking isn't finished, by a long shot. I know you're hurting," he squeezed the kid's cheeks again, "so we'll defer the rest of the spanking until tomorrow. Give you a little breathing space."

He roughly hauled the kid to his feet and grabbed him by the hips, pulling him over between his knees, facing the principal at a distance of less than a foot. DuPree was amused to see that the kid's cock was arching out, bringing it within a few inches of the principal's face.

He spoke directly to the head of the kid's cock. "OK, Cooper, you'll return here tomorrow at exactly 3:35 p. m. and receive the remainder of your punishment."

Matthew was embarrassed -- he couldn't see very well, but it almost looked like the principal was staring right at his half-erect cock! Oh, God, what would Mr. DuPree think of him -- he was practically hard.

"OK, you can wait here until Miss Timmons brings your clothes back. I'd have you wait out in her office, but I realize that it might embarrass you to have people see how red your ass is."

He got up to go, deliberately brushing the kid's arching cock with the front of his woolen suit. He noticed that the cock jerked and bounced, arching out even more than before.

"I'll just leave a note for Miss Timmons to bring your clothes right in when she gets back." Matt looked horror-struck. "See you tomorrow."

He left a note, asking his secretary to stay with Mr. Cooper and watch while he got dressed, just to make sure he didn't run off with anything.

That night, DuPree called his friend Dan. "Hey, Dan, how about if I make a wish of yours come true? What would you offer me?"

Dan had some inkling that the principal was talking about his neighbor kid -- that was the last time he remembered talking about anything that might be construed as a "wish."

"Five bucks!"

DuPree laughed. "Oh, no, no, no. It's gonna cost you a lot more than that."

By the end of the conversation, they had settled on a price of $50 -- and Dan would show up in DuPree's office the next day at 3:30 to pay and collect.

The next day, when Matthew arrived at 3:35 sharp, he was immediately ushered into Mr. DuPree's office. He was surprised to see his neighbor, Mr. Jacobs sitting there, talking to the principal.

"Glad to see you're punctual, Matthew! I think you know my friend, Dan Jacobs?"

Matthew nodded and said hello.

Mr. DuPree looked at him expectantly, "Well, Mr. Cooper, what are you waiting for? Strip! Let's get this over with."

"But... but..." the kid stuttered.

"Come on, come on! You dropped your pants quick enough yesterday! What's the problem?"

Matthew glanced shyly at the neighbor man.

"Oh... shy in front of Dan, are you? Well, he's our official witness. Yesterday, I was in a hurry, but proper procedure requires a witness. Mr. Jacobs was here and I asked him to stick around to witness. I figured you'd prefer that to having Miss Timmons in here, right?"

Matt's eyes widened. When you looked at it like that... "Uh, OK, then." And he started pulling off his shoes and socks. He stripped right on down like the good little nerd he was. Even took off his glasses without being asked.

Dan was blown away. The kid was even more gorgeous than he'd imagined -- and hung like a fucking horse! When he turned away to put down the glasses, Dan could not take his eyes off the way his slender teenage waist flared out into the hottest ass he'd ever seen. And all over those big white cheeks were traces of DuPree's right hand.

DuPree wiggled his eyebrows at Dan. Worth more than fifty bucks already, huh?

"And Matt, since you've been so obedient and cooperative, I'm going to give you a break. I'll give you a choice -- either I finish off the spanking myself -- and that means 25 hard ones, or you can take the rest of your punishment from Mr. Jacobs here. I always think it's a good idea for the people who live in this community to get more involved in the lives of our young people. And just to show you how strongly I believe this, I'd be willing to let you off with -- oh, say just 15 more swats from Mr. Jacobs instead of 25 from me. What do you think?"

Matt was obviously in a quandary. He didn't want yet another man to take him across his knee -- one was bad enough. On the other hand, he remembered how bad it hurt yesterday -- he doubted that Mr. Jacobs would hit so hard. And it wasn't like he was a stranger, really...

"Uh..." Matt blushed. "I think I'd rather just have 15 from Mr. Jacobs." He smiled hopefully (albeit myopically) at the neighbor man. He couldn't really see his face very well (without his glasses), but he hoped he was softening him up. Maybe he'd have pity. He must know what a good boy Matthew was.

It was just as well Matthew couldn't see Dan's face. The man was ecstatic -- DuPree hadn't even hinted at anything like this...

"Well, Dan, he's made his choice. Have you ever given a spanking before?"

"Uh... not really."

"Well, here... I'll help you. Sit over here on this straight-backed chair. OK, now Matthew -- well, you know what to do, right? You get yourself in position over Mr. Jacobs' knee."

Dan couldn't believe it when the nearsighted stud came over and stood next to his right thigh. My God! That gorgeous dick of his was swinging around right in front of his nose, practically.

"Uh, here, Mr. Jacobs. I'll just get over your knees." And then he slowly leaned forward and began pressing his big cock and balls against the side of Dan's thigh -- at least that's what it felt like to Dan.

As far as the kid was concerned, he was just getting himself into position. By angling in from the side, he ended up with his cock and balls kind of shoved back between his thighs -- in full view of the overwhelmed man over whose lap he was going.

The principal decided to guide things a little. "OK, Matthew, hold it right there -- you might want to spread your legs a little. You'll be a little more comfortable -- a little less squished if you know what I mean." He chuckled as Matt blushed bright pink again.

Matt knew what he was talking about, but Mr. DuPree was right -- it was more comfortable when he spread his thighs apart.

"And there's one difference in the last half of the punishment. For the first half, I spanked the outsides of Mr. Cooper's asscheeks. For the last 15, you will be spanking the insides. It's a little tricky, Dan, but Matt and I will help you. Right, Matt?"

A little squeak came from the vicinity of the teenager's head. "Yes, sir."

Mr. DuPree choreographed the action -- Matthew was to keep his legs spread and his ass up in the air; the principal himself would hold Matt's right cheek to one side to expose the teenagers deep crack. Dan would hold Matt in place with his left hand, while spanking along the inner sides of his asscrack with his right.

Smacckk!!! "Yeow!" Matt was amazed by how much more this hurt than yesterday. He jumped and bounced. But good boy that he was, he kept his legs well-spread.

Smack!!! Smack!!! Smack!!! It just kept getting worse. By the fifth swat, Matt was already whimpering and wriggling continuously around.

With some cues from DuPree, Dan began to spank deep in the teenager's crack -- directly on his cute little asshole. After each swat, he began "rubbing it in" -- pressing his palm hard against the boy's little hole and twisting it from side to side.

Matt was horrified to realize that he was getting hard -- whatever his neighbor was doing between swats, it felt incredible. And he noticed that as soon as Mr. Jacobs had added this new element to the spanking, the swats were not nearly as painful. He just hoped the men didn't notice that his cock had grown to its full size, and that it was now rubbing up and down against the outside of Mr. Jacobs' thigh every time he squirmed.

God, he couldn't stop. The confused teenager found himself involuntarily pressing his asshole back against the man's sweaty palm and slowly humping his hips up and down in rhythm with the spanking.

Oh, my God! If he doesn't stop, I'm gonna... I'm gonna... My God, that must be 15 by now. Oh, please God let him stop. Oh! Oh! Oh! He was moaning.

Finally (after about 35 swats, by DuPree's count), the kid started bucking harder and harder and groaning out loud. Then, just as Dan smacked his tiny asshole one more time, he exploded. Moaning -- almost yelling -- he began cumming all over Dan's wash pants. Dan ran one sweaty fingertip over and over the boy's asshole as the boy humped his thigh.

Finally, after producing an almost unbelievable quantity of cum, he let out one long deep sigh and sagged over the man's lap, totally spent. Dan quietly stroked the boy's full, soft cheeks as he waited for him to get his breath back.

Within minutes, Dan could feel the hot body of the naked teenager begin tensing up. The kid started wriggling around, trying to get up.

"Oh, god, I'm so sorry. I'm so sorry. I didn't mean to..."

"That's OK, Matt, don't worry about it. Happens to the best of us. Everybody gets a little turned in the last stages of a spanking. It's perfectly normal." Mr. DuPree sounded hearty and avuncular.

"But I messed up Mr. Jacobs' pants."

Dan laughed. "Like the principal said, Matt, don't worry about it. It wasn't entirely your fault." He winked. "Maybe you could make up for it by doing some yard work for me or something."

By now Matt was on his feet, his cock still swollen from the hardon, swinging from side to side and dripping cum all over the place. "Oh, gosh. I'm really messing up your office."

"Here, Matt," Dan pulled out a handkerchief and grabbed the teenager's cock, wiping off the excess liquid. "That should do it. Here," he pressed the handkerchief against the end of Matt's cock, then took Matt's hand and placed it over the handkerchief, "just hold it there."

After a few minutes, once the kid's cock stopped leaking, they got him dressed. Mr. Jacobs suggested that he stuff the handkerchief down the front of his briefs for the time being, just so he wouldn't accidentally leak through his pants.

Mr. DuPree gave him a brief lecture and told him he hoped never to have to see him in these circumstances again.

Since the school day was over, Dan offered the kid a ride home. Matt quickly accepted -- actually felt sort of a bond with the man. He'd never really talked to him before, but he seemed like a nice guy and all.

When they got home, Dan suggested the disheveled-looking teenager might want to clean up at his house before going home. No point in Mr. Cooper finding out what had happened.

Matt was relieved -- he'd been sure Dan was going to tell his father all about it.

As soon as they got inside, Dan said he'd need his handkerchief back now - he was going to wash everything. He walked up to Matt, opened the front of his pants and jerked them down to the teenager's ankles. While Matt was trying to figure out how to react, Dan reached down inside his briefs and casually unwrapped the handkerchief from around the kid's big cock. Then, with Matt still gasping at the sensation of Dan's hands groping around inside his underpants, Dan held up the cum-soaked rag.

"While I'm at it, maybe you should get out of the rest of those clothes and I'll toss them in, too - they're kind of wrecked."

Somehow, the whole thing seemed so natural that Matt hardly thought twice about it. He started methodically stripping down, just as he had done in the principal's'office. Dan also stripped off the rest of his clothes, including the cum-covered pants, and took them, together with the handkerchief and Matt's things, and threw them all in the washer.

Dan was careful to keep Matt relaxed about it all, letting Matt take a shower first, providing towels and shampoo. Then he took his turn. The two of them shared a Coke and talked as they waited, naked, for the laundry to finish.

Over the next several months, Dan had occasion to discipline his neighbor's kid more than a few times -- once at the kid's own request. They became quite close.

Dan thought about doing a makeover on Matt -- turning him into a more popular type -- but at heart, the kid really was a nerd -- he was happy with himself just as he was. And it suited Dan just fine to keep that incredible face and body a secret from the rest of the world.