The Saga of Middleton Pt. 01

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Jim Grogan quickly made it clear to his new stepson that he had no intention of taking his father’s place. He told Tom that if he wanted, he could call him Jim, rather than Dad.

But he also made it clear that he was going to be a father to Tom — not a buddy. That he would expect obedience and respect.

Tom, always an easy-going kid, thought this was fine. He told his jock buddies that his new stepfather was OK. Jim was a lot younger than Tom’s mother, but after being a widow for 10 years, Tom thought it was good for her to have a life. He didn’t remember his dad very well any more, anyway — he was only 7 when he died. Now, at age 18 (almost 19), Tom was a good-looking, athletic stud in Middleton High School, popular with students and faculty alike — only a fair student, but with a face and body to make any parent proud.

Jim was a successful young lawyer who had lived in Middleton all his life. He was aware of Tom’s family, but had never really paid much attention until one high school football game less than a year before. In that game, Tom, who was substitute quarterbacking after an injury (he had only just turned 18), had been tackled late — the ball had already been passed. He hit the ground on his back and skidded a few yards in the mud. When he stood up, his football pants had somehow split down the back on the left side and Jim was struck by the perfection of the naked young asscheek that was suddenly completely visible — thrusting out of the torn and muddy pants, it was smooth, white, round — meaty and a little jiggly.

It took a few minutes for the coach to notice it. In that time, Jim was completely overwhelmed by the boy. His helmet had been removed to see if he was OK, and the perfection of his face, with his blond hair and puppy dog brown eyes resonated with something deep in Jim’s psyche. He wanted one of those.

With his systematic lawyerly background and exclusively heterosexual experience, once Jim found out that Tom’s mother was a widow, it was just a matter of time. Although Jim was only 28 and Martha, Tom’s mother, was 36, they hit it off from the beginning, and less than a year later, they were married.

The new rules of the household were pretty much like the old — Tom was relieved. There was one exception — Jim strongly disapproved of hip-hop styles. He refused to allow Tom to wear his low-hanging, baggy pants.

One Saturday afternoon, Tom came home for lunch to find that his closet had been cleaned out, pretty much. When he went to Jim, his stepfather announced that they were going on a shopping trip to get him some more appropriate jeans and shirts. Tom wasn’t too happy, but he thought, what the hell — his mother liked the guy, so this wasn’t all that big a deal.

Down at the mall, Tom followed Jim into a place he’d never been in before. The clothes were mostly preppy, but they had a lot of jock-type clothes, too. Jim led him over to the prewashed denims. A good-looking young salesguy came over, disdainfully eyeing Tom’s one remaining pair of baggies.

Jim asked the guy to show them some “decent-fitting” denims, preferably pre-worn. After looking over a few possibilities, Jim and the salesguy picked out a couple of pairs of very pale jeans that looked like they’d been worn A LOT. Jim sent Tom back to try them on.

They fit perfectly. They followed every curve of Tom’s voluptuous lower body. His big, perfect asscheeks were snugly cupped and displayed. The only flaw was the somewhat rumpled look around the crotch and thighs that resulted from the bunching of Tom’s boxers.

“While we’re at it, what kind of briefs do you have? Those boxers will have to go,” Jim declared. Tom looked thoroughly dismayed — he loved the freedom of his boxers. Besides which, he felt almost naked in these close-fitting jeans — he’d never worn anything but baggies.

The salesman grinned, “I’ve got some jock briefs that would be perfect with those pants. Hold on.”

He came back with a box of briefs styled as jock straps — cotton, but backless, the pouch held to the waistband by straps that cupped the asscheeks in back, just like a jock. He pulled one out of the box and handed it to Jim, “What do you think?”

Jim nodded. “They look fine. Try on a pair with the jeans, Tom, and let’s see.”

Tom was taken aback. His face reddened as he watched Jim fingering the cotton crotch of the briefs. Jim looked up and caught his stepson’s eye. He grinned slightly. “They look to be about the right size. Here you go, son.” He handed them over and Tom slunk back to the changing room.

A few minutes kocaeli escort later he was back, his face still a little red. Clearly, the briefs fit perfectly. The jeans conformed snugly to the pouch in front, highlighting its thrust and bulk.

“Turn around.”

He did, and even the salesguy gasped. With the jock-style of underwear, it was a lot clearer how thin the jeans were. They could see the whiteness of the straps of the jock where they ran under Tom’s asscheeks and up to the waistband. By contrast, the expanse of the pale jeans that covered the boy’s thrusting asscheeks appeared to be slightly tinged with pink, displaying just how thin the denim was and how there was nothing underneath but bare ass. Fortunately for Tom, he couldn’t see this angle — he was just concerned about the way his crotch mound seemed to be over-emphasized in front.

But he had no say, really, and Jim ended up buying half a dozen pairs of the jeans and a dozen pairs of underwear. He was obviously intending to refill Tom’s underwear drawer as well as his closet. He also bought the boy a number of tanktops — some more conservative “for school,” others cut deep with thin straps “for sports or fooling around.” He had Tom try on one of the latter type — more as a thank-you to the sales guy than because he felt it necessary.

Tom’s well-tanned pecs looked great in it — the thin straps couldn’t cover his big dark nipples — they kept slipping out on one side or the other. The snug fit also showed off his perfect 6-pack and v-shaped torso. They were thin enough that the nipples showed through, even when they were covered.

That weekend, when Tom hung out with his buddies, there was a major sea-change in their relationship. They teased him a little, but there was no denying the boy looked like some kind of wet dream. They couldn’t stop staring at the pink asscheeks, practically visible as they thrust out the thin denim in back. The dark shadow that was visible between those asscheeks suggested ideas these jocks had never before considered.

The hide-and-seek game his oversized nipples played with the straps of his tanktop kept drawing their eyes as well. The sexiness of nipples was an old story to them, from their many experiences with cheerleaders in many back seats. Especially nipples on big thrusting tits. Like Tom’s. They were turned on and freaked out at the same time.

But it was on Monday in his first class that Tom began sending out waves that would seriously affect his future — and the future of every other boy in the school, as well. Mr. DuPree, the principal of the school, also taught senior social studies. At 8:58 a. m. that Monday, he was seated at his desk in front of his usual classroom. He heard the sound of a book falling to the floor and looked up — and there, not five feet from him, was Tom — facing away from the front of the room, bent over and sliding his backpack under his desk.

Now Mr. DuPree had always secretly enjoyed looking at Tom’s body — what he could see of it. On those few occasions when he’d had the opportunity to be in the boys’ locker room when Tom was changing, he’d gotten a few quick glimpses of his naked charms.

But now here, in his own homeroom, he was faced with Tom’s big, round asscheeks, barely covered by a pair of pale, paper-thin jeans. As he stared, unwillingly but helplessly, he began to register what Tom’s buddies had seen on the weekend. He could see the white straps of the jock under the jeans, and by contrast therefore, everywhere else he was seeing the pink expanse of Tom’s naked asscheeks under the thin denim. And given the way the denim was clinging to the contours of his cheeks and asscrack, if it weren’t for that damn jeans seam running through his crotch and up his crack, he’d probably be able to see the boy’s hot little butthole.

Mr. DuPree managed to get his mind under control, and made it through the class without visible distress. But afterwards, when he was sitting in his office, debating as principal the merits of the current school board proposal that a modified corporal punishment rule be revived, he smiled and imagined the discipline young Tom would receive under the new guidelines. Still smiling, he quickly signed the form, checked off the “yes” box and sent it back to the board for processing. He leaned back and started planning the next few days.

The next week when Jim received the announcement from the school, he realized immediately that Tom’s new wardrobe was starting to have an effect. He knew enough about Mr. DuPree to know that getting kocaeli escort bayan his hands on Tom’s ass was probably the chief motivating factor here. On the form that was enclosed, he checked off “Yes, with parental notification and involvement.” He did, however, put some restrictions on the specifics of the punishment.

That night, he explained to Tom what he had done, saying he supported the school’s efforts to cut down on bad behavior among the students. He trusted that Tom would keep that in mind and stick to the straight and narrow here, because it was now his ass — literally — that was on the line.

Not surprisingly, 3 days later, Jim got a call at his office — Tom had been disrespectful to a teacher and was due to be punished. Would Jim like to be present?

Jim would. He was at the school half an hour later, and went straight to the Principal’s office. There, in the secretary’s office, he saw Tom, waiting for his punishment. Tom looked up, looking worried and a little scared.

Jim looked at him sternly. “What’s this all about? What happened?”

Before Tom could answer, Mr. DuPree opened the door to his inner office and invited the two of them in. Jim was seated in a comfortable leather chair to one side, while Tom remained standing in front of Mr. DuPree’s desk. He was wearing his standard gear — in the principal’s small office, his body dominated the room, his half-revealed tits and ass looking big and ready for action.

Mr. DuPree began, “Look, we all know why we’re here. Tom, you’ve been bad and are going to be punished for it. I will be spanking you as per the corporal punishment guidelines. Strip down to your briefs.”

Tom just stared at him, dumfounded. He’d never heard anything about stripping!

“C’mon, Tom. Time’s a wasting,” Jim chimed in. “I’ve got to get back to the office.”

Slowly, Tom bent over and pulled off his shoes and socks. More to delay than anything else. Then, blushing and looking out of the corner of his eye at the principal, he pulled off his tank top.

Mr. DuPree sighed. The boy’s upper body was as perfect as it had looked in the quick glances he’d had in the locker room. And now he could take it in close-up and at his leisure. Tom’s big dark nipples jutted out from the boy’s full, smooth pecs.

Blushing ever darker, Tom unfastened his belt and slowly undid the snap and pulled his zipper down. The slower he moved, the more erotic the moment. The two men were fixated on his hot muscular ass. This was the first time that either of them had had the opportunity to take a good long look at the kid’s smooth bare cheeks. Jim, of course, had known that the ass would be bare — for Mr. DuPree, it was just glorious serendipity and he drank in the sight.

“Our school has opted to spank, rather than paddle, Tom. For which you should be grateful. I am going to spank you over my knee, after which your father will do the same.”

Tom stared, wide-eyed at Jim. Jim smiled, “I know we agreed with your mother that there would be no corporal punishment in our home, but this is part of the school’s requirement. I agreed to abide by the school’s policies and I will stand by that agreement.”

After a few minutes, Tom didn’t feel so lucky. It took a while to get the position right — finally, Mr. DuPree was ready, with Tom’s bare ass high in the air over the principal’s raised knee and Tom’s big cock and balls pressed firmly into the man’s thigh.

And the principal had such a weird way of spanking! He began by swatting one cheek, leaving his spread hand pressed against the cheek for several seconds. Then he squeezed the cheek slightly, raised his hand up and swatted the other cheek. Again, he pressed his palm against Tom’s asscheek and gave it a firm squeeze before continuing with the next swat.

At first, Tom was mainly embarrassed by the way his bare ass was getting so thoroughly felt up — and by his principal, yet! But after a dozen spanks, the burning of the swats themselves started dominating his thinking. It didn’t take long before Tom was making little noises and grunting each time a spank landed.

But then things got even worse! Mr. DuPree reached over with his left hand and spread Tom’s cheeks slightly, so that he could spank deeper into the boy’s crack. He spanked up and down the teenager’s deep crack for several minutes. Finally, Tom’s ass was spread wide open — Mr. DuPree had his cheeks spread wide enough to expose everything — even his tight little pink asshole. And right in front of his stepfather!

Around escort kocaeli the 40th swat, he started spanking directly on the sensitive asshole itself. Instead of squeezing, he rubbed his sweaty palm across the young man’s tight little hole. Every time he did that, Tom felt an electric tingle in his big dick. To his enormous embarrassment, he felt his cock starting to grow. By the time the principal stopped — after about 50 spanks — Tom was hard as a rock, and there was no possibility that Mr. DuPree was unaware of it.

After the last spank, Mr. DuPree paused for a few minutes. He kept Tom’s cheeks spread, his palm pressed against his asshole in the deepest part of his asscrack. Tom was grateful that the pause gave him a chance to pull himself together. By sheer willpower, he managed to soften up his cock at least halfway back to normal. The pain was bad, but it would have been even worse to have to stand up with a full hardon for both men to see.

When Mr. DuPree finally released Tom’s asscheeks and gave him one last little swat to tell him to stand up, Tom was relieved that his oversized cock was no longer rigid. While his big basket bounced around in front of him, his cock arched out only slightly more than usual.

While Tom rubbed his sore pink asscheeks, the two men changed positions. All too quickly for Tom’s liking, Jim called him over for the second half of his punishment. As he stood in front of his stepfather, he was horrified when Jim reached out, curled his fingers into the boy’s waistband and in one quick motion stripped the briefs down to Tom’s ankles.

Without the briefs to hold it back, Tom’s cock arched out quite a bit more than it had been, nearly slapping Jim in the face as he leaned forward to pull down the briefs.

“OK, Tom. Step out of them. The official requirement is that spanking be done on the bare ass. Your principal was nice enough to let you get away with wearing your briefs, since your ass was bare. But I believe in doing things the way the book intended.”

Blushing even more strongly, if such a thing were possible, Tom stepped out of the briefs, his big dick arching out and swaying as he moved. His oversized balls were on display, too, and he could see that both men were smiling and enjoying his humiliation.

Jim positioned Tom next to his right knee, then bent him over it. By the time he had him in place, his ass was high in the air, thighs spread, with his half-erect cock and balls pressed back so that they were fully visible between them. Mr. DuPree had an inspiring view of his student’s beautifully formed genitals and ass just an arm’s length away from where he was sitting.

Jim imitated the principal’s spanking form — he would never have dared to be so touchy-feely himself, but with the technique already established, he guessed that Tom wouldn’t think anything of it. This was the culmination of his long campaign — at last he was getting his hands on that hot ass he’d fallen in love with so long ago. For a good 15 to 20 minutes, he spanked, stroked, squeezed and felt every inch of the teenager’s smooth, muscular butt. And with the principal’s example before him, again, he even got to spend a while pressing and stroking the kid’s hot little asshole.

By the time Jim was done with his half of the spanking, Tom was yelping and squirming big time. After the last swat, Jim paused about half a minute to let it sink in, then stood up, simultaneously pulling Tom to his feet.

While Tom hopped around, rubbing his sore ass, the teen’s stepfather and principal watched, smiling broadly, as the kid’s now-rigid cock bounced and swayed — protruding at least 8 inches in front of him.

Finally, Jim announced that he had to get back to his office. He hoped Tom had learned his lesson, and he thanked Mr. DuPree for helping him keep his son in line.

The door closed and a naked and sniveling Tom was alone with the principal. Mr. DuPree demanded that Tom come over and stand in front of him while he recited in detail his misbehavior, its possible consequences, and the importance of punishing such behavior immediately and firmly. He spoke at great length, allowing his eyes to roam freely over the teenager’s naked body, with long pauses on his still rigidly erect cock and nipples.

Finally, he had Tom turn around so he could inspect his ass and make sure no damage had been done. In the process, he had the teenager bend over while he spread his cheeks and checked out the deepest reaches of his asscrack, especially right around the asshole.

“Looks fine to me,” he declared finally and released the young man’s asscheeks. “Better get dressed and get back to class now.”

As the teenager finally turned and left the principal’s office, the man was pleased to see that the pinkness of his ass, where it showed through the thin jeans, was much brighter now and more obvious — almost a cherry red.

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