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Matthew Thomas wiped the sweat off of his brow with his damp t-shirt, pushing his dark brown hair to the side as he fumbled for his keys to his mailbox. Matthew had just gotten back from his Saturday morning run along the West Side Highway. His strong, hair-covered legs that were responsible for this 6’1 frame were still tanned from a long summer spent on the beach. His tight stomach showed a delicate trail of hair that teasingly disappeared into the waistband of his running shorts as he wiped away the five miles of sweat. Matthew located his keys as he reached his mailbox in the new apartment in Chelsea, Manhattan. He’d moved in in August after having graduated from university in May. Luckily, he landed a cushy job at a bank a few months before graduating which not only allowed him to take the summer to backpack across Southern Europe but also afford a studio apartment in his favorite neighborhood. Matthew inserted the small mail key into the box to reveal a wad of envelopes and leaflets. He’d been so busy at the office the last week, he hadn’t had time to check his mail. As closed the box and made his way up to the third floor of his building. As he walked slowly up the steps, he quickly thumbed through junk mail until a bright red mailer caught his eye. “You’re invited!” It clearly read at the top of the page. It was from his high school, St. John’s Academy for Boys. He could barely believe that so much time had already passed and he was being invited to his five-year high school reunion. As he entered his apartment he threw down his keys along with the other pieces of junk mail but continued to read the invitation. He flipped it over to find a message and picture from the principal of the school: James Redding. Principal Redding was named to his position when Matthew was a Junior. The youngest principal of St. John’s Academy at 43, Principal Reddington was a scholar and incredibly handsome. Matthew was closeted in high school but he could remember being completely obvious about his lust the first time he saw Principal Redding. Standing at 6’3, his strong jaw and well-manicured beard stood out proudly in front of his broad shoulders and firm, mountainous chest. As he walked down the halls, his muscular legs and round butt would press tightly against his fitted slacks, teasing to be let out. On the rare days when students didn’t have to wear uniforms, the Principal would forgo his tie to reveal a dusting of curly, dark brown hair that Matthew hoped extended down his firm torso. With his sleeves rolled up, he display strong hairy forearms and wide hands with meaty fingers. Now, 48, Principal Reddington looked as good as ever, Matthew thought, his kind green eyes and full lips were framed by a now salt and pepper beard and a smile that sent an electric shock through Matthew straight to his tightening shorts. Matthew was pulled from his daydreaming as he felt the precum ooze out of his increasingly hard, uncut cock. All 10 inches of his veiny member throbbed as he stripped his shirt and shorts. He walked toward the bathroom as he playfully teased his cock with one hand, and held Principal Redding’s picture in the other. He set down the photo as he turned on the shower and entered under the warm embrace of the water. He leaned his entire body against the cold tile as he manipulated his engorged cock with both hands. As he stroked, he imagined Principal Redding’s lips encircling his cock, pushing it to the back of his hot, moist throat. Matthews hips thrusted forward and backward as he fucked his hands. He moaned softly fully knowing that he was getting close to blowing his load. Just then, one final thrust of his pelvis sent him over the edge ropes of thick, white cum shot across the shower as he moaned “Fuckkkk” under his breath. He hadn’t cum like that in a while and it left him panting. He caught his breath and concluded to himself “I need to go to that reunion.” Later that day, Matthew flipped open his laptop to RSVP. With thoughts of Principal Redding still running through his mind, he thought “why don’t I send him a note… to check-in?” He typed in his email address and simply wrote “checking in” on the subject line. “Dear Principal Redding -- I know it’s been a while so I’m not sure if you remember me but I wanted to check-in. I received my invitation to the five year reunion in the mail and am really looking forward to attending. I hope to see you then so we can catch up more in person. Sincerely, Matthew Thomas” “Sent,” Matthew said out loud. He quickly shut his computer and tried not to think about what he had just done. Later that night, Matthew stumbled back into his apartment after a few drinks with some work friends. He opened his laptop to binge something on Netflix when he released his email was still open. He has several unread messages, mostly spam or coupons, but one stuck out “re: checking in.” Nervously, Matthew clicked the email open: “Matthew -- It has been a while and of course I remember you… fondly. I am looking forward to seeing you at the reunion. -Jim”
“Jim.” The informality did something to Matthew and immediately his cock sprang to life from his drunken haze. He fell into bed with his hand in his pants, wrapped tightly around his dick. He pumped with one hand as he replied with the other. He scrawled a quick and simple message and it send: “Great! See you then  ” He shut his computer to finish what the email had started. Gobs of hot cum coated Matthew’s abs and chest as he dozed off to sleep. He would have no memory of his response… or the wink. A few weeks later, Matthew was on a plane to his native Cinncinati. As he sat in the cramped economy seat, he couldn’t help but think about seeing his principal again. He dozed off a few times only to wake up with a pool of precum forming a small wet spot on his jeans. After he graduated, Matthew’s parents had moved for his mom’s job so once he landed, his best friend from high school, Paul, picked him up. The reunion was later that night so they went straight to Paul’s apartment to get ready for the night ahead. “I can’t believe you’re dragging me to this stupid reunion,” Paul said buttoning up his shirt. “I haven’t thought about half of these douchebags since we graduated. “Oh, come on! Don’t you think it’ll be fun to see how fat everyone’s gotten?” Matthew said jokingly with a smirk. Paul just rolled his eyes as he fastened the buttons on his sleeves. “Plus, it’ll be good to see some of our old teachers. I heard Principal Redding is going to be there,” Matthew notes while tying his shoes. “I guess he’s cool. Whatever, there’s free booze so I’ll be happy. You want one?” Paul questioned as he motioned to Matthew with a beer. “I’m good. I want to be on my A-game going into this thing,” Matthew retorted. “Suit yourself,” Paul said with a chug. “Uber will be here in 5, get your shoes on.” Paul and Matthew hopped out of the Uber and onto campus for the first time in five years. The large, grey stone buildings framed with vines of ivy looked more like a university in New England than a prep school in the Midwest. They entered the main hall of St. John’s and followed the tasteful, yet effective signage to the reception room, The Rutberg Library, so named for the school’s founding principal Fr. Herman Rutberg. The room was full of young men dressed in smart, business casual clothes. Pressed white shirts and fitted blue blazers were scattered across the room. Matthew gingerly entered the room, scanning it from left to right. He sighed as he didn’t see the one he had hoped for. Maybe he couldn’t make it. Disappointed, Matthew made his way to the bar with Paul. Paul ordered a shot of tequila and a beer while Matthew opted for his standard vodka soda. They both made half-hearted small talk with their former classmates. Matthew started to feel foolish for investing so much thought… and cum… in this fantasy when out of the corner of his eye he saw him, Principal Redding. As gazed intently as him across the room. The principal looked up from his glass of whiskey on the rocks to finally make eye contact with Matthew. When their eyes met, jolts of electricity shot through Matthew’s body he felt himself blush as he noticed the principal make his way over to him. Matthew took a sip of courage when he felt a tap on his shoulder. “Matteo! Como estas?” It was his Spanish teacher, Señor Juarez. A lovely man under any other circumstances but the fact that he interrupted his big moment made him a nuisance. “Bien bien. Muchas gracias. Y tu?” Matthew distractedly made small talk with his former teacher, quickly calmed by the man’s cheerful disposition. He almost forgot how annoyed he was with him. “Ding ding ding.” Someone hit the rim of their glass with a knife. The group of 60 or so men all turned to the front of the room to face the Vice Principal who stood stoically. “On behalf of the leadership of St. John’s, we wanted to welcome the class of 2014 back home. We are so honored to have you as graduates and are so proud of everything you’ve accomplished thus far,” he espoused. “I know you didn’t come here to hear us talk but your host for the evening wanted to say a few words. Principal James Redding,” he said gesturing to the back of the room. Matthew twisted his neck to see the principal make his way to the front of the room. His presence filled the space as he nodded and waved to the graduates amid a chorus of applause. As he passed Matthew, he placed his hand on his shoulder, giving it a tight squeeze as he stepped to the front. Matthew looked down and readjusted his belt for fear that his hard on was visible. Principal Redding spoke briefly but eloquently thanking everyone for attending and reminding them of the annual fund they can donate to. After he finished, he was swarmed by a few brown nosers who wanted to make their presence known to the principal. Matthew didn’t mind because he was so distracted by the rod in his pants being seen. Every time Principal Redding made eye contact with him another stream of blood filled his shaft, making it harder and harder. He looked down and tried to figure out a way for it not to be seen. “Do you need some help with that?” Matthew didn’t need to look up to know that deep masculine voice belonged to Principal Redding. He raised his eyes to gaze upon the smiling man. “Umm…,” Matthew uttered nervously. Had he been caught? “Your drink. It looks like you’re in need of another,” Principal Redding suggested. “Ha... I guess I am,” Matthew laughed. “Shall we?,” the principal motioned toward the bar. They walked over. “I wanted to thank you for your note, Matthew. It was nice surprise to hear from you.” “No problem, Principal Redding, I figured it would be nice to check in and see how everything is.” “Please, call me Jim,” he offered. “You’re a graduate now, we can do away with those formalities,” he said with a wink. They spoke for a good 30-minutes about life after high school and college. Matthew held onto every word that passed through his principal’s lips. Jim was still a confirmed bachelor, living in a house not far from campus. He’d been traveling a lot between semesters and doing triathlons and other races to stay in shape. They both laughed as they shared stories and sipped their cocktails. As they sat in the small seating area toward the back of the library, Jim put his hand on Matthew’s thigh and gave it a tight squeeze, with the same force and grip as he did on his shoulder earlier in the evening. Matthew’s cock visibly pulsed in his pants. Surely Jim saw it. From across the room, the Vice Principal called Jim over. “Looks like I’ve got to go say some ‘goodbyes’. Don’t go anywhere. I still want to hear more about your ideas for the alumni association,” Jim commanded. As he got up Paul hobbled over and slumped into the maroon leather chair. “Man, I gotta go home. I’m so drunk,” Paul stuttered. “LOL are you okay? Do you want me to call you an Uber? Or your mom?” Matthew laughed. “Nahhhh, I’m good but I need to leave now,” he said fumbling with his phone. “You gonna stay? You good to get home?” “Yeah, bud. I’ll be alright. Get home safe.” “Aye aye captain. I’ll leave the door unlocked for you. Be safe!” Paul mumbled blowing his friend a sloppy kiss. As Paul left, he passed Jim on his way out the door, offering him a high-five that was hesitantly reciprocated. “Is Paul going to be okay?” Jim questioned to Matthew pointing to his friend stumbling to the chair. “Oh yeah. He’s a trooper. Most annoying part about the whole thing is that he doesn’t get hangovers. 8am tomorrow, it’ll be like this never happened,” Matthew said. “To be young again…” Jim mused. “Come on… you look great and you know it. Those races are working out for you,” Matthew smiled, shocked by his own forwardness. “You’re too sweet,” Jim said grabbing Matthew’s thigh again. “Say, when was the last time you were on campus? Have you seen the new offices since the renovation?” “No, I haven’t seen. Only in photos,” Matthew noted. “Come on, I’ll give you a tour,” Jim hopped up and motioned Matthew to join him. They walked down the dark halls into the executive suite. Jim pulled a collection of keys out of his back pocket and thumbed through them to find the right one. “Perks of being the principal is that I get a key to everything… Downside is that I never remember which one is which… Ah! Here it is.” He turned the knob to pop open the door. The lights turned on with their movement to show a beautifully designed modern space that radically contrasted with the rest of the antique hall. “Wow! I love it,” Matthew awed. “Isn’t it great?” Jim remarked. “Here, let me show you around.” They walked through the space as Jim pointed out the various points of interest. Matthew looked adoringly at his sexy tour guide. “And now, Matthew, I want to show you my favorite part: my office,” he smirked. Jim moved forward opening the pair of double doors into a large bluish grey room with a large wooden desk in the center and two leather chairs placed in front of it. The walls were full of art and bookshelves stacked high with books. Matthew entered the room and looked around as he heard the door shut behind him. “Pretty great, isn’t it?” Jim questioned. “It’s beautiful. The kind of office you deserve,” Matthew suggested Matthew looked intensely at the books on the shelves as Jim made his way to the large leather chair behind his desk. “Why don’t you give the principal’s chair a try. I promise it’s the most comfortable chair you’ve ever sat in.” Matthew smiled as we walked over to the chair to have a seat. “Wow! This is really comfy,” Matthew remarked. Sinking deeper into the chair Matthew closed his eyes. As he fell into a state of relaxation in the silent room he felt the warm touch of Jim’s hands on his shoulders. The only thing audible were their increasingly labored breaths as Jim’s worked his large hands into Matthews tight muscular frame. Matthew let out a soft moan, unable to deny the pleasure he was feeling from the impromptu massage his former principal was giving him. Upon hearing the moan, Jim turned the chair around to face him and pulled a dazed Matthew to his feet. His hands tightly gripping Matthew’s tense arms he leaned down and kissed the boy he once called his student. The touch of Jim’s lips on his sent a shock wave between their bodies, causing Jim to pull Matthew in closer. Matthew’s tongue tenderly pried apart the principal’s lips, meeting his tongue in a sensual dance. Matthew’s hands ran up and down Jim’s wide back as their kiss and embrace continued. After what seemed like a lifetime, they pulled apart in unison, breaking their kiss. “I’ve wanted to do that all night…” Jim admitted. “Me too,” said Matthew, still warm in Jim’s embrace. “Before tonight I was worried that you might not be interested, but I figured the wink face you sent me in your reply to my email was a good enough guess to go off of…” Jim smirked. “Wink face? What… Oh no… I didn’t…” Matthew was embarrassed. “You replied to my email with a wink. You don’t remember?”“I don’t… I had been out that night and was a little buzzed when I responded… ugh…” He moaned. “What are you complaining about?” Jim questioned. “It brought us here,” he said with a wink. “Now, where were we?” Jim lifted Matthew onto his desk with one swift motion, never breaking their kiss. He tongued and kissed Matthew’s neck as he fumbled with the buttons of his white shirt. With each button, Jim explored a new area of Matthew’s hairless body. Once his shirt was open, Jim laid Matthew on his back on the desk. He teased and twisted his sensitive nipples as he nuzzled his furry face into Matthew swollen bulge. “Uhhh take off your shirt,” Matthew commanded as he pushed Jim’s head out of his crotch and began to quickly undo his belt. Jim ripped each button as fast as he could to reveal two large pecks covered in a crop of the curly dark brown hair that had teased Matthew all those years ago. His large nipples stood proudly erect. Jim placed each one between his thumb and forefinger as he watched his former student undo his belt and pull down his pants, revealing an even more impressive bulge that had soaked his black briefs through with precum. Matthew began to slide down his underwear when Jim grabbed his wrists. “Allow me,” he instructed. Jim fell to his knees and slowly pulled the boy’s waistband down. With each inch, Matthew’s cock was closer to being unleashed. Suddenly his thick and throbbing 10-inch member sprang out of his shorts, slapping onto his tight abs with the release. Jim moaned in ecstasy. Without skipping a beat, he pulled Matthew’s foreskin down to expose the glistening head of his cock and engulfed the shaft halfway to the hilt. Matthew snapped his head back and grabbed on Jim’s arms, digging his nails deep into his hairy skin, as his principal bobbed up and down on his hung meat. Jim was a pro. He swallowed the cock deep to the back of his throat in a repeated motion, easing up on the shaft to give individual attention to the base and head. He grasped Matthew’s balls. He rolled them in his large hands like marbles and teasingly tugging on his full sack. Matthew was in God Place and could barely maintain a steady breath. Just as he was getting closer Jim let go of his cock and balls, and pulled Matthew to stand and switched positions with him in front of the desk. Confused, Matthew sat silently as Jim kissed his neck and nibbled his ear. “I want you to fuck me,” Jim whispered into Matthew’s ear between nibbles. “Now.” Jim pulled down his slacks and briefs in one motion to reveal a seven inch thick cock standing straight out of his two well-muscled hairy legs. He turned around and lowered his stomach onto his desk to display his perfectly formed, round ass covered in the same hair that landscaped his chest. Anxiously he waited for the boy’s large cock to penetrate him. “I want you to use your spit but you’re really big so if you need lube there is some lube in the top… uhhhhhhh,” he loaded moaned unable to finish his sentence. Matthew had buried his face and tongue deep into his principal’s tight pink hole. He gnawed on his hair, muscled cheeks and punched his hole with his aggressive tongue, loosening it with every thrust. “You said you wanted me to use spit, didn’t you?” Matthew laughed before going back to his meal. Jim could only respond with a moan and buried his face into his folded forearms. Matthew devoured Jim’s ass for at least 15 minutes. The sensations were incredible but Jim had had enough. He needed to be fucked. “Pleeeeasseeee. Fuck me. Don’t make me beg.” “What was that?” Matthew joked. “I didn’t hear you.” “Fuck me, Matthew.” Smirking Matthew teased Principal Redding primed hole with his massive cock. He spit into his hand and smeared it across his rod as he slowly pushed the head into Jim’s eager hole. “Easy, easy,” Jim begged. He uncrossed his arms and rested on his forearms like he was going to do a plank. He arched his back so his ass was at a perfect angle to be penetrated. With each slow inch, Jim moaned deeper and louder. When he could feel Matthew’s cock pressing against his second hole he wasn’t sure he could take it anymore. “Alright, I’m all the way in.” Matthew exclaimed. “Man, you’re big. Okay. Give me a second.” Jim pushed back on Matthew’s cock and began to slowly fuck himself on the boy’s impressive rod. Matthew threw his hands behind his head as he watched his principal impale himself on his throbbing cock. Between moans and deep breaths, Jim spoke, “alright, you can fuck me now.” Matthew didn’t need anymore permission than this. He began to deeply and deliberately thrust far into Jim’s tight hole. Sweat poured off of his brow and chest, and pooled on the small of Jim’s back Both men moaned in unison, never wanting the fucking to end. “Flip over,” Matthew directed. He wanted to see the firm hairy chest of his principal as he fucked. Matthew grabbed Jim’s ankles and held them high to reveal a pulsing and tired pink hole. Matthew reentered his principal with an effective thrust, causing him to almost yelp. Matthew leaned down to kiss his principal because they both knew that neither could last every longer. “I… I can’t hold off much longer,” Jim panted. “Me too... Cum together?” he winked. “Yeah... I’m… I’m cummminngggg.” Jim let out a final moan as rockets of cum shot out everywhere from his raw shaft. Seeing this, Matthew quickly pulled out of Jim and jerked his cock one quick pull before exploding. Six volleys of thick, hot cum coated Jim’s hairy chest. The last volley made it to his beard which he quickly lapped up with his eager tongue. Exhausted, Matthew collapsed right on top of his principal. Jim kissed the boy’s forehead as their cum mixed together on their naked bodies. After a few minutes of silence Matthew rolled onto his back to dangle on the desk next to his principal. “I’m really glad I came to the reunion,” Matthew sighed. “I hope that doesn’t mean we’ll have to wait to do this again until your 10 year?” Jim asked. “You said you live close to school right?” “Yeah about 10 minutes, why?” “Can you wait 10 minutes?” Matthew winked and kissed his principal on the cheek.
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