Well it was the time. Every good thing has an ending. It was back to school time. Simon always despised this time. His school was in a wealthy neighborhood. And he was the charity case. A quota kid, like the kids from the center were called, as the school was paying for everything as per the law required as a quota. They were always dressed like charity cases in the middle of high fashion dressed kids.
But this time he would look different. And show up not the same. The weekend prior, Jim took him to the shopping mall and Simon had an almost unlimited budget to buy clothes, accessories and school supplies. The big guy was supervising and they were also able to squeeze a quick blowjob in a booth. Simon got a load of new clothing, new phone and computer and an electric scooter! Simon was still in awe after getting all that and it made coming back to school way more interesting.
As he was locking his scooter on the rack near the school entrance, he took his sweet time, knowing he had a free period anyway to get ready. He was wearing designer jeans and a t-shirt over his slender but firm body. His backpack lazily thrown over his shoulder, the big earphones and his fluffy hairs made him look like literally the young adult he was. By his arrival, his cooler demeanor and his look, he knew he was the talk of his circle. At the top of the stairs he was climbing while the ring stop, he noticed the principal at the top. He was always there on the first day to welcome new students. He was a big man. Well dressed, intimidating… until his smiles appeared on his face. As Simon was passing by him, their eyes locked for a good second. And they realized probably at the same time that they had met previously. At the creek in the park last summer. Simon had given him a blowjob near the creek.
Being pressed by other late students Simon went back to the present moment but could not believe he had sucked the school principal! As he was organizing his stuff, the principal’s secretary told him Mr Watley wanted to see him regarding his subsidies for the year. Simon followed but was confused. Those subsidies were supposed to be discontinued because Simon reached 18 last summer. Then he remembered. It was the principal’s name. He followed her to a place he never been before. The principal’s office was basically a 2 room thing. One for the secretary and storage and one for him, with a closing door. As she guided him to the office, the principal was behind his desk. Serious looking but a big bulge between his legs. « Simon, nice to meet you. Everyone noticed you look different now. » Simon smiled at him. « Yes I found myself. I am living with an uncle of my late mother. He has a good influence on me I think. I really found myself this summer. Got in shape, lot of running and bathing in creeks! »
That broke every tension in the room. The principal stood, closed the blinds behind the windows and sat on the corner of his desk. « So it was you? ». Simon reached to run his cocks over his pants and nod. It came to life, springing instantly, making a tent. « I have a meeting in 10 minutes » blurted out the man. Simon’s answer was to take the man’s meat out and sucking it frantically. Squeezing his lips tight around it. Vacuuming it. In less than 2 minutes the principal came in his willing mouth. He swallowed everything, licked the cock clean, put it back in the pants and zips everything closed. « There you are… you are still early for the meeting! » The principal seemed in awe. « You are a pro. My secretary leaves at 3PM. Come back then, we’ll speak. They left the office, Simon waving the secretary who probably had been oblivious to what happened.
His first day had been his best school day ever. He was now feeling accepted, not the weird kid. His teachers were cool. But moreover, he would have fun with the principal. He waited to see the secretary leave and almost everyone as well. He texted Jim he’d be late. He answered quickly that it was ok but don’t be too late. Simon knew he had Father Gabriel visit tonight. And then entered the office. All the blinds were closed and the lights shut like everyone had left. As soon as he entered, the principal grabbed him, positioned him on the wall, spread his legs and pull down pants and boxers. All Simon’s was hearing is the heavy breathing of the guy. He arched his back, smiling. Without a word, a well lubbed cock was pressing hi little star. Simon relaxed himself and felt the cock penetrating him softly. Followed by big grunts, thrusts and slap on the cheeks. Simon was holding on the wall while being used hard. After a while, the principal found his rythm and Simon was enjoying every second of it. The guy knew to fuck an ass. Jim was better but that was it. The principal cock’s had a major upward bend and a nice girth to it. Simon was feeling each it of it and suddenly the principal made a move that reached his prostate a couple of time and Simon squirted cum everywhere on the floor. He was glad it was on the little tiled pathway instead of the carpet. Almost simultaneously the principal shot chords of cum in his butt. They stayed that way a while. Until Simon’s arm started to shake. « I’m gonna fall sir! » The principal pulled out. « You can call me Bruce when we are alone kid. I dreamed of that since this summer at the creek! » he said as he was wiping his cock on the soft skin of Simon’s crack.
They sat there, immobile a while. Bruce smiling at Simon. « I hope I get to see you often this year, Simon. I must say it’s the best ass I fucked ever and one of the best blowjob I received. I knew you were one of a kind! » « Thank you si… Bruce. I was not going to come back, my uncle almost forced me! I am happy now. I’ll come as often as you want. I just don’t want to be discovered by my fellow students! » The principal nodded pensively. « I understand… I have a wife and 2 kids. But what about your uncle? » Simon smiled. « He won’t mind, believe me. »
They left after that, Bruce rubbing Simon’s head. As he was going back home, he could not believe what was happening. As he arrived, Jim was already grilling steaks, whistling through his lips, just wearing a short. Simon kissed him. « You are so beautiful. Simon pulled down the shorts and hidden only by the grill, he gave Jim a quick blowjob. They sat outside as Simon swallowed the last drop of cum and ate their steaks. « You seemed way happier than this morning. Good day at school? » Simon laughs. « The best but not for the school thing. No Jim. I just fucked the Principal. … more he just fucked me! »
As Simon recounts the events of the day, Jim marvels how his little boy is becoming a good slut and an even better bottom. He said once that he preferred to cum with a cock in his ass instead of someone touching his cock. His attention refocused on Simon after he finished describing that Bruce had wife and kids. « Are you talking about Bruce Watley? » Simon nod affirmatively. « I never knew he was a Principal now. Damn we were going to the sauna together to find fresh asses! That’s so funny! If he is still the same, I bet his sex life with his wife is… limited! » Jim seemed genuinely happy and they made plans to organize a meeting.
Shortly afterwards Simon was pleasuring Father Gabriel. He knew what the preferences of the old priest were. He loved being sucked slowly but with a finger in his butt. Then he take Simon on missionary looking at his small cock going hard under his pounding. Then on doggy. His large cock was always stretching the hole to his max. Father Gabriel cocks was the last one hurting him a little bit when he entered his little hole. Then he proceed to fuck him with deliberate long thrusts, pushing his big cock the deepest he could. He would then grunt and cum in his butt. And Father Gabriel was always finishing by pissing on him. Simon was surprised and a little bit disgusted the first time but he now enjoyed the moment. He drink as much piss he could, letting it drip all over him afterward, enjoying the hot sensation. Father Gabriel then gives him a towel to pat himself dry then readjust his clothes. Today he was in his priest regalia. And made a cross sign. Simon enjoyed being fucked by a guy wearing a cassock.
Often after he goes chatting with Jim and Gabriel but tonight Jim waived him and sent him back to his room since there is school the next day. Simon obey because he was conditioned to, but he was sad. His last cock of the day should be Jim’s. It was the rule. Later, has he was sleeping and dreaming of the Principal cock, Gabriel piss or Jim fucking him, he awakens with the sensation of Jim pushing to enter him. His hand pushing him on his bed, his beautiful cock disappeared in Simon’s ass. With a few thrusts, Jim came in the small butt. He whispered in Simon’s ear. « I will never forget, baby » then proceed to fuck him hard until his cum join those of a Principal and a Priest.
