The Education of Scott: Trilogy

After Scott's intense three way with Tom and Ben, he walked around with a constant erection which could barely be contained by his khakis and boxers. Memorial Day weekend had been particularly rough for him, as his wife was out of town visiting her relatives and wouldn't be back until Wednesday. When he reported to school on Tuesday morning, Scott was more than ready for some hot action!

As it worked out, an unexpected opportunity presented itself almost immediately. Kevin Mooney, the very handsome 22 year old gym instructor had forgotten to pickup his paycheck on Friday and Scott decided to deliver it to him in person. As he walked to Kevin's narrow office in the back of the gymnasium, soft moans could be heard coming from inside. Scott's cock lurched in his pants at the thought of what Kevin might be doing all by himself early in the morning, before his students came in. Fortunately, the door was only partially closed, so Scott was slowly able to push it in, until he had a perfect view of the mouth watering sight greeting him.

There was Kevin slouched on a bench, leaning backwards against a locker. His sweat pants were down around his ankles, and a very stiff cut dick and heavy balls protruded from striped boxer shorts. Kevin's eyes were tightly shut, and his right hand flew over his well lubed cock. The principal's prick went nuts in his own boxers, as he jacked off every day in the same way, with his cock and balls spilling out of his shorts.

Scott watched Kevin masturbate for a good minute before deciding to surprise the devil out of him. "Good morning!" Scott grinned as the horrified gym instructor opened his eyes. "Jesus!!" Kevin got up and tried to pull his sweat pants back on. But Scott was too quick for him, and stepped on the black fabric which had bunched on the floor.

"No need to stop Kevin, I was just going to join you!"

With that Scott unbuckled his trousers and let them drop to his ankles. His impressive prick and cute balls immediately spread the wide fly slit of his white boxer shorts. Scott grabbed the bottle of lube that was on Kevin's desk and coated his thick member until the sensations were too much for him. Then he slowly jacked off, to the surprise of the lanky gym teacher, whose eyes were still popping out.

"I can't believe you are going to do this with me." Kevin started jacking himself again, a little slower than Scott's frantic pace.

"Why not, guys should do this together more often, right?"

"Well, yeah..but," Kevin hesitated. "You're the principal!"

"And we have 5 minutes before the bell rings, let's make the most of it!"

The two men watched each other jack off for a good minute before Scott had an idea.

"Let's switch dicks."

"Uhhh sure, I guess."

Kevin slowly wrapped his hand around Scott's impressive prick and jacked the head vigorously. Scott let out a loud moan and in return, stroked Kevin's dick backwards, squeezing his cockhead on each upstroke.

"Oh, man!" Kevin muttered. "I'm almost there!"

"So am I!" Scott croaked "Let's cum together!"

"YESSSSSS!! This is it! ARGGGGGHHH!"

Kevin's prick started spewing cum everywhere, as his intense orgasm set Scott off.

"SWEET JESUS!! THAR SHE BLOWS!!!"

Scott's cock squirted with such force he let out a loud bellow which could be heard for a city block. The two men grunted and groaned as their collective equipment shot off 15 creamy spurts. When their dicks were finally drained, Kevin lay in Scott's arms in an ecstatic afterglow. Just at that moment, the late bell rang.

"Shit! Gotta go!" Scott hastily tucked his equipment back in his boxers and pulled up his dress pants.

"See you tomorrow, same time, same place!"

Kevin was so spent all he could do was wink at the horny principal in return. Then, he pulled his sweats back up and reluctanly prepared for his first class, wiping up 15 blobs of cum in the process!

****************************************

Jerking off with Kevin had been great, but Scott was still horny by noon. He had promised he would help carry some new equipment to the photography room on the third floor. As Scott hustled to meet Mark Moriarity, the Photography teacher, he wondered if his new intern would be starting today. Mark was only 23 and had just joined the faculty. His intern, David Koots, was supposedly in his third year of college.

By the time he had reached the remote photography center, Scott was sweating like a bull. The room was always beastly hot and today it must have been 95 degrees! Scott was a bit surprised that nobody was around, as he was a bit late. Just at that moment, Mark and David emerged from the nearby darkroom. The 20 year old intern was drop dead gorgeous, with short black hair and wire frame glasses. He was easily six foot four inches tall and had washboard abs to die for.

"Hi Scott," Mark smiled and looked over at David. "This is David Koots, my new intern!"

"Nice to meet you." Scott shook David's hand vigorously. "Welcome aboard!"

"T-thanks." David responded nervously. He was extremely shy, and still a virgin.

Mark showed the other two men what equipment needed to be moved, and for a while they worked together in silence. Then, Scott decided it was time to make his move.

"It's hotter than hell in here, I'm going to get more comfortable!"

With that, Scott kicked off his shoes and quickly removed his jacket and shirt. Then he opened his pants and stepped out of them.

"WHAT ARE YOU DOING???" David was incredulous.

"I told, you, I'm getting comfortable!"

At that point Scott was naked except for his white boxer shorts, which were obscenely tented with his endowment.

"Aren't you going to join me Mark?" Scott gestured to the photography teacher, who couldn't keep his eyes off the hunky principal.

"Uhhh..sure." Mark awkwardly unbuttoned his shirt, and lowered his pleated pants. He wore a sleeveless undershirt and red plaid boxer shorts.

"I can't fucking believe you guys are doing this!" David was turning beet red, trying not to look at the two men in their underwear.

"Why aren't you stripping?" Scott glared sternly at David. "Are you wearing pink panties today?"

"N-n-n-ooo," David turned seven shades of crimson. "It's just that..."

"Oh, I see..." Scott nodded. "Seems like you have a little problem here!"

The principal placed the palm of his hand over the jutting bulge in David's slacks. Almost instantaneously, the virginal intern let out a loud moan.

"Oh, excuse me," Scott corrected himself. "I mean a BIG problem." He continued to manipulate the swelling bulge, delighting in the feel of David's turgid cock insistently pressing against his khakis.

"Mark, take care of his shirt, I'll lower his pants." Scott gave a wicked grin to the photography teacher, who winked back.

"NOOOOOOOOOOO!" David tried to hold up his hands, but that just made Mark's job easier. He quickly lifted the intern's jersey over his head as Scott removed his loafers and hastily lowered his dress pants. David wore a crew neck t-shirt and baby blue boxer shorts. Scott expertly manipulated his thin 9 inch cock out of the boxer fly and slowly started to jack it.

"MY FUCKING GOD!" David screamed what are you doing?"

"Just relax!" Scott smiled at him. "You ain't seen nothing yet!"

With that Scott opened his mouth and took in David's mushroom prickhead in one gulp. The intern let out such a loud groan Mark thought he had been hurt. He quickly realized the handsome intern was getting his very first blowjob. He got on his knees as well, watching Scott gradually deep throat David's cock until he could easily take in 6 inches in one gulp. David was grunting and screaming in complete abandon, trying to hold back a massive load. Scott gestured to Mark at one point, who gladly sucked on David's balls like a madman, sticking his tongue back as far as it would go. David started to screech in complete ecstasy, as the two men alternated sucking his stiff bone and sensitive balls. Then suddenly, as Scott thrust a good eight inches of the intern's prick into his mouth, David lost his load.

"FUCKING BITCH!!!" David started squirting cum in Scott's mouth with such force it dribbled down the principal's cheeks and neck. Scott swallowed what he could, then spit out enough cum to fill a small bowl. David had spasmed seven times, and was completely spent. He collapsed on the floor, panting as his sweat dripped onto the new rug.

"Pretty good welcome, huh?" Scott had cum all over the place as well, though not as heavily as the young intern.

David could barely talk. "Y-y-y-eah...I can't believe what just happened!"

"Believe it man!" Mark grinned. "Just wait until tomorrow!"

"T-t-t-t-omorrow?" David's eyes practically popped out of his head.

"Yeah, tomorrow," Scott was now fully dressed and turned to leave. "Carry on, gentlemen!"

David's jaw lowered as the principal closed the door. He was too confused to process anything yet, only that he had just gotten the tube job of a lifetime....

**********************************************

Scott was sexually satisfied for a few hours after giving David his first blowjob, but around dismissal time felt the familiar twinge in his loins. His last meeting of the day was going to be a difficult one. Mark Thunem, the 19 year old senior class thug, had tried to destroy the final project of two 18 year old Eagle Scouts, Earl Reid and Matt Jonessy. They had built some new choral risers which were stacked against the wall in the chorus room. Mark tried to stuff some newspapers soaked with lighter fluid around the risers and actually started a small fire at one point. Fortunately, a student walking in the hallway noticed the smoke right away and the new risers only sustained very minor damage.

Scott decided to meet with all three men in his office after the rest of the staff had left. Earl and Matt were extremely geeky, although quite handsome in their own way. Earl was a big man, having short blond hair and well developed pecs. Matt was the proverbial 90 pound weakling, and as he walked his baggy jeans could barely cling to his small frame. Mark looked like the typical gangsta senior class boy....covered with piercings and tattoos, with pants that sagged so low 6 inches of his striped boxers stuck out. Scott decided not to expel Mark, even though that was a definite option. The skater dude had the tightest butt Scott had ever seen, and he was determined to explore every nook and cranny of it before the day was up!

Earl and Matt were a bit scared to be in the same room as Mark, but Scott finally talked everyone into meeting in his office. As the three men entered the room, no one talked or looked at each other. Scott was the first to speak, and his stentorian voice echoed in the spacious room.

"Mark, you are very lucky that fire didn't spread. I could have arranged for you to miss graduation, awards night, and the senior prom. You aren't even going to be expelled!"

"I'm not?" Mark couldn't believe what he was hearing.

"Of course, you have to make this up to Earl and Matt," Scott continued in mock seriousness. "So, one of the first things you need to do is strip to your underwear."

Mark looked like he was going to be sick as Earl and Matt grinned. "W-w-w-hat are you going to do to me?" The gangsta boy was trembling inside, but he tried not to show it.

"You'll find out," Scott glowered. "Now strip!"

With shaking hands, Mark took off his shirt and kicked off his shoes. He then turned away from Scott and let his very baggy pants fall in a heap at his ankles. Stepping out of his white socks, Mark kicked his trousers away. He had a lion tattoo on his chest, nipple piercings, and was clad in nothing save for a pair of red and white striped boxer shorts.

"Ok, now Earl and Matt need to strip to their underwear as well!"

The two eagle scouts were totally shocked. They hesitated, as Earl finally got enough courage to speak.

"But, Mr. Morrison, we didn't do anything. We shouldn't have to strip down!"

Scott was adamant. "Don't worry, I think you'll understand what is going to happen very shortly. Now, all I want to see are shorts and t-shirts."

The two eagle scouts were quite shy and took a long time removing their uniforms. Earl wore a v-neck white t-shirt and blue plaid boxers, while Matt sported a crew neck t-shirt and green plaid trim boxers with cute little slits in the side.

"Ok, I think we are ready," Scott smiled in anticipatory glee. "Mark, have you ever given another guy a blow job?"

"W-w-w-hhhattt?" Mark couldn't believe what Mr. Morrison had just said. "N-n-n-oooo, I don't know how..I can't do that!"

"You can, and you will, or I will see to it you will not graduate!"

"Oh, come on!!" Mark was feeling trapped. "I have to fuckin' graduate...my old man promised me a car!"

"Aw too bad!" Scott just stared harshly at him. Now I want to get on your knees and take turns sucking Earl and Matt's cocks until they cum in your mouth."

"Fuck you!" Mark tried to run out of the room, but Scott quickly stopped him. Realizing it was futile to fight, Mark decided to just quickly get it over with. He got on his knees in front of Earl, who was practically hyperventilating at this point. The big man's eyes popped as Mark reached into his boxers and pulled out a fat seven inch cut cock. He tentatively licked the head with his tongue, then opened his mouth and swallowed Earl's cockhead in one gulp. Earl let out a loud moan, then started bucking his hips to try to get more of his prickslab in Mark's mouth. Gradually, the thoroughly humiliated skater boy got about 4 inches of Earl's hard-on his mouth and started deep throating him, hoping he would cum right away. Scott realized what Mark was doing, and quickly guided his head to Matt's basket. Mark sucked Matt's bone through the material of his trim boxers, then reached into the fly and hauled his 6 inch prick and small balls into the open. Matt squealed like a girl as Mark easily got most of his relatively small boner into his mouth. Scott let Mark deep throat Matt for a good minute before easing his mouth off the eagle scout's cock. The very aroused principal by that time was naked except for his white boxers, which tented with his massive erection.

"Pretty good cocksucking Mark, now it's time for you to be cornholed." Scott grinned at the hapless gangsta skater dude in his most evil way.

"C-c-c-ornholed??" Mark was totally shocked. "But I never did that, I can't do it!" He was practically crying as he looked up at Scott pleading for mercy.

"Don't worry, you won't be able to walk for a while, but you'll survive!"

"NOooooooo.....Please, I can't do that!!"

Mark tried to run out of the room, but Earl and Matt blocked his exit. Scott, in turn bent Mark over his desk and quickly removed his boxer shorts. Mark's butt was sparsely hairy and looked as tight as a drum. Scott inserted a couple of fingers into Mark's behind and frigged him slowly. The gangsta boy let out a loud moan which was a mixture of pleasure and pain.

"THAT HURTS! THAT FUCKIN' BURNS!"

Scott laughed. "It's just a fucking finger or two Mark, just wait until I get all 8 inches up there!"

"EIGHT INCHES! THAT'S GOING TO SPLIT ME IN TWO!!" Mark was bellowing louder and louder, but it wasn't doing any good.

"That's the idea, man!" Scott chuckled again and put the head of his engorged shaft against the gaping entrance to Mark's butt. Then, he shoved forward suddenly, burying about 3 inches of stiff cock up Mark's bunghole.

"FFFUUCCKK!!! I CAN'T TAKE ITT"

Mark screamed as Scott continued the relentless onslaught on his tender behind. The sex crazed principal felt an electric shock travel throughout his body as inch after inch of his hard cock disappeared into Mark's butt. After 2 minutes of sweating and grunting, Scott was in Mark so deeply the skater dude could feel the material of his boxer shorts pressing against his ass. At that point, Scott withdrew for the first time, causing Mark to sigh contentedly. Then he thrust forward nearly to the hilt, delighting in all the noise Mark was making.

"FUCCKINGGG BIITTCHH!! I CAN'T TAKE IT! TAKE IT OUT!! I CAN'T FUCKKING DO IT!!!!"

Earl and Matt were so excited watching Mr. Morrison take Mark's cherry butt their own dicks once more swelled to full hardness. Earl spontaneously stuck his stiff dick into the fly of Matt's boxers, and delighted in the feel of his friend's erection entering his own underpants. The two eagle scouts started to thrust their dicks in and out of each others' boxers, groaning and moaning as their sensitive cocks mashed against each other inside the constricting fabric. Scott, in the meantime was having a very hard time holding back. Mark's butt was even tighter than Ben's and the sensations he was experiencing as he took the skater boy's cherry butt were unbelievable. After a particularly deep thrust Scott knew he was at the point of no return.

"I'm there, I'm going to POP!"

"FFFFUUCCCCKKK"

Mark screamed loud enough to wake the dead as Scott exploded in his behind. At the same time, Earl and Matt went over the brink, squirting in each others' boxers until they were soaked with cum. Scott came a good nine full spurts before finally pulling his cock out of Mark's ass with a loud plop. The skater dude had cum a bucket as well, all over Scott's desk and discipline folders.

The four men were so fucked out it was a while before anyone spoke. Finally, Scott managed to clear his throat and managed a muffled croak.

"You can graduate with the rest of the class Mark. I'll pretend nothing happened." With that, he took Mark's cum stained discipline folder and threw it in the garbage.

"AWWWW SHHITTT! I CAN'T MOVE! MY BUTT FEELS LIKE IT'S ON FIRE!"

"Cut the crap, Mark!" Scott was getting his wind back. "We all know you flunked out of Drama Club!" Earl and Matt laughed as they got dressed, enjoying the sight of the lowly skater dude Mark covered with cum and sobbing softly. It had been a day to remember, especially for Scott who now was thoroughly comfortable with man-to-man sex. But...could tomorrow top today's sexcapades?

to be continued...