Jordan had broken the School's strict rules by sneaking into town without permission, but he didn't care. His chances of getting caught were slim: he knew his roommate would cover for him. Anyway, the Dean for Student Affairs, Mr. Twaddle, had given his notice two weeks ago, and the boys were pretty much unsupervised, at least until the new dean arrived, which wouldn't be for another week, at least. No, he was home free, even if he had missed the last bus, and had to hitchhike back.
It was never hard for Jordan to get a ride: some lecherous old dude always stopped, sooner or later. Seventeen year-old Jordan was quite a dish, after all: tall and slender with soft brown hair that fell to his shoulders and a cute, boyish face. He was wearing his tightest chinos that showed off his bubble-butt perfectly. He hadn't had to buy a drink all night at the Jockey Club, the small New England town's only gay bar (heavily frequented by the more daring brats from Whittlefields Academy ), even if he had had his cute little ass pinched and fondled a few times. Well, it had been worth it!
It was chilly, though. The winter wind cut right through the thin khaki and tickled his balls. He jammed his hands into the pockets of his bomber jacket and trudged in the direction of the school. Cars passed, infrequently, and he stuck out his thumb, but none of them stopped. He tried to give each driver his best little-boy-lost look, but to no avail. _d_a_m_n_! Bed check was only a half-hour away! Daniel would cover for him as best he could, but if that little prick Hastings, the floor monitor, suspected anything, he'd tattle for sure! Bryan Hastings delighted in getting the other boys in trouble: one day the skinny little ass-kisser was going to get his!
A light snow was starting to dust his light brown hair when a Cherokee braked in front of him. Breathing a sigh of relief, Jordan sprinted for the open door.
"Thanks, man!" he said to the driver as he got in. "You really saved my butt!"
"Did I?" The driver said, coolly. Jordan looked over and jumped, involuntarily: the driver had an eye patch over his right eye. Not that it looked grotesque, quite the contrary. The fortyish, well-dressed man, with close-cut salt and pepper hair looked, well, kind of dashing, like he would imagine a secret agent would look.
"Wow!" Jordan exclaimed, involuntarily, as the car pulled back onto the roadway. The driver laughed.
"Oh, this," he said, tapping the eye patch. Nothing, really. Hardly think about it any more, old boy. Now, where exactly are you headed on this inhospitable night?"
"Uh. to Whittlefields. It's just up the road a bit. Hey, thanks. I would be in big trouble if I got back after bed check."
"Ah, yes! I just happen to be passing right by there. Sort of a strict school, eh?"
"Nah, not really," Jordan began warming to the man's company. "They think it's tough, I mean, but I got ways of getting around the rules, if you know what I mean."
"Ah, clever lad! That's the spirit. What they don't know can't hurt you, eh?"
"You got it, dude! I sneak out whenever I want. Haven't been caught yet. We gave old man Twaddle such a hard time, he quit!" They both laughed. The Cherokee slowed and pulled in the gate. "Uh, better let me out here. Don't want anybody seeing me."
"Righto. Well, cheerio, then!" Jordan shut the door and the car headed around the circular drive. Jordan sprinted for the dormitory.
He got back at ten minutes 'till eleven, just time enough to slip out of his jacket and wet shoes and get nice and casual before the monitor's nightly visit.
"Had a blast, dude!" he was saying to his roommate Daniel, when the knock came on the door. "We're here, Bryan!" they chorused, as that little weasel, Bryan Hastings, entered with his stupid clipboard. He had a nasty grin on his face.
"You're in deep doo-doo, Jordan," the little ass-kisser sniggered.
"What for? I've been here all night, studying!"
"Yeah. Go snitch on someone else, _d_i_c_k_less," Daniel said. Good old Daniel!
"Well, the new Dean is here, and he said both of you are to be in his office in fifteen minutes," the skinny little blond replied, gloatingly. "I hear he's real tough, too!" Bryan made a mark in his stupid clipboard and left, giggling.
"Oh, _s_h_i_t_!" Jordan said, with a sinking feeling in the pit of his stomach. "He wasn't supposed to be here until next week!"
"Oh, man! Jordan! What the hell did you do? Now it's my ass, too, and I didn't do anything! Oh, great! You're always getting me into it!"
"C'mon, Danny! Get real! Nobody saw me. He can't prove a thing. He probably just wants to lay down the law, is all. Twaddle probably told him we were, like, real troublemakers or something." Daniel ran a hand through his close-cropped brown hair, like he always did when he was nervous. "Lighten up, dude!"
Still, Jordan had a distinct feeling of discomfort as they knocked on the door to the Dean's Office, at precisely eleven-fifteen.
"Come in!" Both boys entered, closing the door behind them. The Dean's high backed leather chair was swiveled away from them, towards the window. The man had a deep voice: it sounded strangely familiar.
"Well, boys," the voice came from the swivel chair. "I'm going to give you a chance to own up. I have a report that Jordan was off campus tonight. Is that true?"
"Uh, no sir! I was in my room, studying!"
"Yes sir! He was! Studying I mean. Sir." Daniel stammered.
"Is that the truth? Both of you? Think carefully." Jordan didn't like this at all. Something wasn't right. Daniel gulped and glanced over at him. He decided to buff his way out of it.
"Yes sir. That's the truth!"
"Absolutely, uh, sir," Daniel said, haltingly.
"I'm sorry you said that," came the cool reply, and then the chair swiveled around to face them, and Jordan was even sorrier, for there sat the driver of the Cherokee, who had given him a ride back from town!
"Oh, god ... we're doomed," Jordan murmured, in a weak little voice. The man stood up. He was much taller and more well-built than he had looked in the car. Jordan glanced over at Daniel: he was white as a sheet, and his mouth hung open.
"I cannot tolerate lying, above all. Had you boys but told me the truth, I should have given you a mere ten strokes each, but now I am afraid that I will have to 'put the fear of God in you', so as to speak. Jordan: lock the door." Jordan complied, numbly. He was really in for it, now.
"Uh, sir? Sir. Uh, I didn't do anything. I don't see why I should get licks, too."
"Well, Daniel. Standing up for a friend is an admirable thing indeed, but one should be prepared to take the consequences for one's actions, nonetheless." From a drawer, he produced a wicked-looking, short wooden paddle, with large wooden holes in it. Danny looked like he was about to cry. He certainly regretted wearing only a jock strap and warmups. "That table there will do fine. You can place the objects from it and from your pockets on my desk." He tested the paddle with a couple of quick swishes through the air. It whistled. Daniel and Jordan cleared the small table, and Jordan dropped his wallet on the desk.
"Please, sir," he looked into the stern face imploringly. "Don't whip Danny. He did it for me ..."
"Enough of that, now. I have explained already. I am sure you are fine boys, but I have my duty to do. Now, Jordan, you stand by the desk. Danny: bend over that table. I want you to grip the opposite edge tightly. That's right."
Daniel looked like he was about to cry. He bent across the table, obediently. It was lower than his waist, and his round, muscular butt stuck up invitingly. The outline of his straps showed through the tight gray cotton. Stepping behind him, the Dean swung the paddle with practiced form, as though it were a cricket bat. Jordan could see Daniel's butt tense in anticipation. He felt his _c_o_c_k_ beginning to harden. This was strangely erotic, seeing his roommate like this, helpless and humiliated. The paddle swung high and then lit with a loud KAPOW! Danny's breath hissed between his teeth, and his eyes squinted with the pain.
KAPOW! KAPOW! KAPOW! KAPOW! By the fifth one, Danny was yelping out loud. By the tenth, he was bawling like a ten year-old. Hot tears spilled down his cheeks, onto the table top. After twenty-five licks, the Dean set the paddle down. He rolled up his sleeves. Danny was sobbing so his shoulders shook. Jordan's boner was obvious under tight khaki. The dean picked up a second implement: a riding crop! Jordan's balls shrank in his Calvin Kleins! If Daniel was getting it this bad, what must he be in for? Somehow, the expectation only aroused him more.
"Now Danny: be a man. It's almost over." The dean stepped behind Daniel and gripped the waistband of his warmups. He tugged them down to the boy's knees, exposing his naked buttocks, protected only by the scanty straps of his jock. Danny's butt glowed a bright pink: it must be burning, Jordan thought. He could feel a wet spot in his briefs.
"Please, sir! I'll never lie again!" Danny sobbed. "PLEASE! Not my bare ass! I've been punished enough! Don't ... YEEEEOOOWWW!"
The crop slashed across Daniel's bare bottom, leaving a dark red streak in its wake, across both buttocks. Again and again the thin leather implement branded Danny's smarting backside, eliciting howls of pain and tortured squirming from the helpless boy, reducing him to blubbering submission.
"All right, boy. Stand up." Danny did, rubbing his unfortunate nates. His eyes were red and his handsome face was red with the crying. His round, athletic ass was bright pink, crisscrossed with dark red stripes. Jordan was shocked to notice that his roommate's ample _c_o_c_k_ was hard as a rock in his jockstrap. The Dean instructed Daniel to stand, pants down, where he would be able to observe Jordan's punishment. Now it was Jordan's turn. He didn't know whether he felt more afraid or humiliated or turned on, or whether the fear and humiliation turned him on even more. Obediently, he took his place, bent over the table. The edge of the table pressed against his throbbing hard-on, exciting him even more. He clenched his teeth, and waited for the first lick. That would be the hardest one, he reasoned. He was very, very wrong.
Standing behind him, the Dean pulled Jordan's shirt tail out, and tugged the waistband of his chinos until the material was as tight as he could pull it across the boy's hard well-rounded ass. Both boys had such luscious young asses, he mused to himself, just perfect for beating. In all his years of disciplining teenaged boys, he had been fair, if strict, but he had always enjoyed this aspect of the job the most. And he had beaten some of the most beautiful bottoms! Surveying Jordan's trim little rump, he had to admit that he would enjoy this one. He considered it a perk of an otherwise mundane job. He pulled the paddle back and aimed for the faint outline of the boy's briefs.
KAPOW! Jordan's rear end just started to burn when the second one hit: KAPOW! And the third. KAPOW! KAPOW! KAPOW! His ass was on fire! He bit his lip and tears came to his eyes as each blow seared his bottom-cheeks, rocking him forwards so that his throbbing erection rubbed against the table top. KAPOW! KAPOW! He started to sniffle, then to cry.
Looking on, Daniel felt somewhat gratified. It was all Jordan's fault: he deserved a licking, if anyone did! Watching his roommate sob, as he had done, seemed to wash away some of his own shame. His throbbing boner strained at his jock strap, hidden behind his clasped hands. He began to slowly rub the head with his thumb, surreptitiously. The combination of his own burning behind and the spectacle of his friend's humiliation were almost all that he could bear. Just as soon as they were cut loose from here and back in their room, he was gonna beat his meat like he'd never beat it before!
Poor Jordan's ass stung like a thousand bees had stung it! Each crack of the paddle elicited another howl of pain from the hapless youth. Just when he could stand no more, it stopped."
"You may stand up, Jordan, and drop your trousers," the Dean picked up the crop. "Smartly, boy, or it will be the worse for you!" Fearfully, Jordan obliged, unbuckling his belt and pushing his pants to his knees. His erection stood straight out in the crotch of his white cotton briefs. "Now: assume the position!"
Jordan yelped as the crop cut across the tender flesh of his burning bottom. As stinging, red-hot fire crisscrossed his butt, he squirmed and sobbed out loud, just as Daniel had done. He felt so ashamed and humiliated, and it hurt so much! Jordan had only received a few spankings as a child, and never such a thoroughly painful one as now! He begged and pleaded for mercy through his tears, but none came. Finally, it was over. He stood up and began to pull up his pants.
"Not so fast, Jordan!" the Dean barked. He had pulled a stool to the center of the room. "Get over here!" To Jordan's horror, he held in his hand a large, flat wooden hairbrush! "Oh, please!" Jordan sobbed, falling to his knees. "Please don't! I'll do anything you say! Please ! Not the hairbrush! I'll be a good boy from now on! I promise not to be bad any more!"
"Get over here!" the dean barked. He sat down on the stool, then pulled Jordan across his lap. "You had your fun, young man, and now you must pay the piper!"
"Please!" Jordan sobbed, as he felt his briefs being tugged down to bare his bottom. "Oh, please, sir! Not my bare ass! Please!" A strong arm gripped him around the waist. Jordan's young ass was a deep red now, from the crease of his thigh to the dimples at the small of his back. The Dean took aim with skill born of long practice.
"WHAP! WHAP! WHAP! WHAP!" The stinging blows fell thick and fast, on the tenderest parts of Jordan's tortured rear end. He howled and writhed as the stinging blows seared his flesh and his throbbing _c_o_c_k_, trapped in the pouch of his briefs, rubbed against the muscular legs beneath him.
Watching, Daniel lost control of himself. The sight of Jordan across the Dean's lap was too much for him: he had rubbed his _c_o_c_k_ through his bulging jock harder and harder until he suddenly realized he had gone too far:
"Uh oh ..." Danny mumbled, then: "Oh ...OOOHHHH!!!" as his _c_o_c_k_ jumped spasmodically, pumping his jock full of hot, pungent boy-cream. Exhausted, he slumped against the wall, frantically tugging his warmups up to hide his crime. Goo dripped down his legs in milky streams.
Sobbing with pain, Jordan went limp, surrendering at last to his punishment. Each stinging blow rocked him forwards across the Dean's lap, rubbing his own rock-hard _c_o_c_k_ until, just when the pain reached its greatest, stinging intensity, he felt his crotch explode in the most awesome orgasm he had experienced in five years of intensive masturbation. He seemed to shoot forever, each contraction timed with another searing blow to his poor, tortured bottom.
Finally, it was over. The Dean instructed both youths to straighten up their clothing and stand at his desk. As he sat down, he noticed large wet spots at each boy's crotch: he had done it again! Well, he knew these young men would never forget this lesson, that was certain: a boy well beaten is a boy well behaved.
"Now," he addressed the two, Jordan still sniffling. "I hope you two have learned you lesson well."
"Yes sir!" they said, in unison.
"I was easy on you this time. Now, go on to bed."
Back in their room, both boys lay in bed (on their stomachs, of course!).
"Did you ...?"
"Yah. You too?"
"Yeah. Man. Easy on us, my ass!"
"Yah. Mine too. I won't b able to sit down for a week!"
"A month!"
"Yah." Then Jordan said, Mischievously: "I'll just have to be more careful, next time!"
"NEXT TIME???" Danny said, and, groaning, turned out the light.