This is a work of fiction and any similarities to people, living or dead, is purely coincidental. It will contain references to gay sex amongst teenagers. If this offends you, or is not permitted in your location, please leave. The story is copyrighted by the author, who maintains exclusive rights to the story other than those permissions required for publication on the Nifty archive.
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JAMES COMES OF AGE
CHAPTER 44 - Prelude - Phillip
Author's Note - This is one of a series of chapters where there will be additional stories about some of the characters encountered in the main series. They will be chronologically related to a main story, with preludes giving background to characters that we have met, interludes between main stories, and postludes containing the story after the character has left the main story.
This prelude is the background to a character introduced in chapter 10.
The second half of the autumn term brought Phillip Wilson's favourite activity for P.E. Swimming meant that he got to ogle his classmates at least semi naked, and they had to get their cock's out to change into their swimming trunks. It did also mean that Phillip could show off a bit as well. He had a big cock, and he knew it. It was about five inches long and thick when flaccid, extending to eight-and-a-half erect. The other boys may not be looking at him in the way that he looked back at them, but at least there was respect there.
This year, P.E. had other compensations as well. It was taught by a newly qualified teacher who must have been around 23, to Philip's 16 years (he had had his birthday a couple of weeks previously). Mr Wood lived up to his name, at least when Phillip saw him. He was very good looking and had a tendency to wear shorts that were just a little too tight. This accentuated his ass from one side and, occasionally, his cock from the other. His well-fitting sports top meant that Phillip was not just breathing heavily from exertion after a P.E. lesson.
It turned out that this half term of P.E. would not just be swimming, rather it would be water polo. This more than alright with Phillip as it would allow him to get up close to his almost naked classmates. There were enough boys in the class for three teams, leaving a third of the class sitting observing at any one time. Whilst he tried to keep his eyes on the game, Phillip also glanced over at his teammates and, when he was close by, at Mr Wood. Somehow, he managed to keep his erection in check in the pool area, especially since one of his classmates had been mercilessly teased the previous year for popping a boner in his trunks.
During the last match, there was a tussle for the ball involving Phillip, two other members of his team, and two of the opposition that Mr Wood thought was getting a bit out of hand. He blew his whistle and instructed the four boys involved to remain after he dismissed everyone else. The match concluded, with Phillip's team losing by one goal. As the other boys gathered the caps and ball up and put them back in their storage boxes, which were then put into the drying room, Mr Wood scolded the five boys. Phillip tried complaining about the telling off as he hadn't really been involved.
"Mr Wilson, if you are going to talk back like that, you will need to stay behind."
"But sir..." Phillip began.
"No, that's enough Phillip. Please wait in the office."
Phillip walked along the side of the pool and stood in the pool manager's office, which was currently unoccupied as it was the last lesson of the day, and the pool manager had headed home early. Through the windows that looked out over the pool, he could see Mr Wood finishing the telling off, dismissing the other four boys, and walk towards the office.
"Now Phillip," the teacher said, sternly, "we need to have a talk about a couple of things. One of the boys said you may have touched him whilst in that little fracas earlier."
"Well, yes sir, we were near each other in the pool, fighting for the ball, I may have knocked someone slightly."
"Not like that. Deliberate touching. Somewhere more intimate."
"No sir!" Phillip exclaimed. This was mainly because he would never do that as he could imagine what the repercussions for him may be.
"But you like looking at them don't you," prompted Mr Wood.
Phillip stayed silent.
"If you do, I'm not going to say anything to anyone. If you want to tell people, that's up to you, but I am asking you to tell me."
"Yes, sir," said Phillp, dejectedly.
"Do you want to know how I know."
"I think I'd better. Then I can know how not to get caught again."
"I've seen you looking," said Mr Wood. "It's been more obvious the past couple of weeks whilst we've been in the pool. But that's not all you've been looking at is it, Phillip?"
"No, sir."
"I've caught you looking at me as well. Am I right?"
"Yes, sir."
"Do you know why it was a good thing that you told me you like looking at your classmates Phillip?"
"No, sir."
"Because I am like you. I caught you looking because I was looking as well. I noticed you in particular always seem to be in a state of excitement at the pool."
Phillip couldn't believe his ears. His teacher had been checking him out at the same time. Not only that, but Mr Wood thought that Phillip's flaccid cock was an erection!
"Why do you think I singled you out this afternoon even though I could see you were on the periphery of that incident?"
"I... I don't know, sir."
The teacher spread a towel over the office desk and drew the blinds over the poolside windows.
"Bend over that desk and hold on tight to the other side," the teacher instructed.
Phillip complied, instantly knowing his vulnerability as his ass was presented by the position, he now found himself in."
"One last question. You want me to fuck you don't you."
"Yes, sir!" said Phillip, with the most enthusiasm of any of his answers in the office. It was finally going to happen. He was finally going to get sex, and not with one of his classmates, but with a hot teacher.
"Well, let's get too it then."
Phillip turned to his head from against the wall. He could see Mr Wood removing his T-shirt. His body was just as good looking as Phillip had hoped - totally smooth, with a decent six-pack. A small bottle of Vaseline was removed from a zipped pocket of the shorts, opened, and placed on a chair. Phillp was breathing very hard now.
Inserting a thumb into either side of the waistband of his shorts, Mr Wood pushed down, leaving the shorts around his thighs. The teacher must have been commando under those short shorts. Phillip would never be able to get away with that. The only disappointment about the teacher was the size of his cock. Erect, he must have been only just longer than Phillip was when soft. He took the Vaseline and began to apply it to himself. Phillip's view of the preparation was interrupted a moment later when the teacher shuffled forward and bent down.
The boy could feel the material of his Speedo being pulled away, then a breeze on his exposed crack. Now there was a sensation of touch. Fuck! The teacher must be licking his ass.
"What are you doing sir?" Phillip asked.
"Oh, I always start and finish like this. It's almost the best bit for me."
It did feel good, Phillip had to admit. This went on for a bit, before Mr Wood stepped back and began to work at Phillip's ring with a slick finger. The rimming had loosened the boy up a bit already, so the first finger, then a second slipped in without too much difficulty.
"Ready?" asked Mr Wood.
"I think so sir," replied Phillip.
The teacher repositioned himself, and this time, instead of a finger at his back entrance, Phillip could feel Mr Wood's hard cock. With a grunt on both sides, it slipped inside. It turned out that Mr Wood was as good a teacher of sex as he was of PE. He entered slowly and made sure that Phillip was comfortable all the time.
Phillip was not sure how long he was going to last. The situation he found himself in was so hot - The teacher fucking him, the chance that someone would walk into the office, his cock rubbing against the soft material of his Speedo. Every time Mr Wood thrusted, Phillip's cock would rub against the Speedo, the towel and his stomach. Never mind what was happening to his prostate every time there was a penetration, Phillip was effectively wanking himself with no hands.
He could feel Mr Wood's hands on his hips, using the boy for leverage as he fucked. All the time there was reassurance. Other than the risk of someone walking in, Phillip felt safe with his teacher, even as the speed of the fucking picked up.
More pleasure flowed through Phillip's body as his prostate was stimulated. He could feel the orgasm building deep within him as Mr Wood's breath shortened. The pain of losing his cherry now replaced by sheer pleasure each time the teacher slid in or out of his ass. He started to try to clench his sphincter to give more pleasure to the man teaching him the ways of the flesh.
The teacher was really slamming into his pupil now, their flesh slapping together as he thrust. Phillip could hear him murmuring to himself, seemingly psyching himself up. Suddenly, there was a warmth inside Phillip as his teacher shot his load into the boy's ass. This sensation was too much for Phillip, especially as his own cock had been rubbing the towel underneath him through the tight silky material of his Speedo. He could feel his cum jetting out and soaking into the fabric.
Behind Phillip, the pressure was released as Mr Woods pulled out. Phillip could hear the teacher's shorts being pulled back up. The sex was not over however, with the Mr Wood resuming his position knelt behind Phillip, now licking the seed he had so recently deposited from the boy's still stretched hole. With a satisfied sigh, the teacher let Phillip's Speedo cover his crack again.
"Thank you, Wilson," he said, "you may go and get changed now."
Phillip stood, the remains of his cum that the towel had not rubbed off still soaking his Speedo. He hoped that no-one would see him going to the changing room like this. There was no-one else. He showered in peace, dried, dressed himself and made for home. There was just a nod from Mr Wood as he left the sports centre.
Next week, another excuse was made for Phillip to stay behind after P.E. He knew what was going to happen now and had made plans. When Mr Wood asked him to bend over the desk, Phillip stayed put.
"Are you not going to do as I ask?"
"Not this time, sir," Phillip replied. "I think after last time I'd like a go doing what you did to me last week."
The situation, and the nerve of what he was doing was making him erect. He could see his teacher's eyes glued to his crotch.
"How big do you get?" Mr Wood asked nervously.
"About eight-and-a-half, sir," said Phillip.
"I thought you were hard before. I've never had one that big and thick."
"You did me last time sir, and I'd never had one at all. I really think you should let me do this."
Mr Wood gulped.
"I'll see how much I can take then. Use plenty of lube and don't forget to use your fingers first."
Phillip had been practicing on his own ass for the past week, so when his teacher was in position, he got the lube and started to gently play with his teacher's sphincter. It was quite tight, almost as tight as his own - it must have been all the exercise Mr Wood got.
As he worked on the muscle, Phillip could feel it getting looser as more fingers got inserted. There was more lube, and each time, Phillip compared his fingers to his cock to see if he was ready to slide in. When he thought the fingers gave roughly the same girth as his penis, he applied yet more lube to his cock and the hole he was about to penetrate and lined up for entry.
The teacher gasped as his pupil's thick cock pushed inexorably past his sphincter. Phillip was breathing hard with the tightness around hi shaft - so much better than his hand had ever been. He kept pushing until the teacher shouted out.
"Enough! Enough. No deeper."
Phillip stopped pushing and began to withdraw. He had almost pulled all the way out before more instructions came.
"You can keep going, just stop about where you did."
Reversing direction again, Phillip pushed in, attempting to judge the stopping point. The more he tried, the better at judging he got. He knew he'd got too deep if Mr Wood yelped. The tightness was not going to let him go for too long before he had to cum. He could feel the orgasm building very quickly.
Phillip began to whimper. He placed a hand on his teacher's back as he kept thrusting, not wanting to go too deep. With a grunt, he emptied his balls inside the older man. He could feel his teacher's body shaking as he too reached orgasm, the size of Phillip's cock helping his speed. This tightened the grip on Phillip's cock, milking even more seed from it.
The boy waited until his orgasm had subsided and his cock had begun to wilt - this time only reducing to a semi - before he pulled out.
"Don't forget how to finish off," he was instructed.
This was the bit he had not been looking forward too. He had managed to avoid it before penetration, but the teacher seemed to want it afterwards. Somewhat reluctantly, he dropped to his knees and began to lap at the cum that was dripping from his teacher's ravaged hole. It was not as bad as he had been expecting. As any gay boy had done, he had tasted his own cum on more than one occasion and was familiar with the taste of it. There was a hint of the teacher's taint, though he clearly showered regularly. The main other taste, not really something Phillip liked, was the lube. He carried on until the taste was mainly that of his teacher's body, then stood up.
"Thank you for that, sir," he said, as he left to shower.
For the rest of the year, Phillip would get to have sex with his teacher every few weeks. Mr Wood had said that they could not make it look regular, but occasionally after lessons, Phillip would be asked to stay behind for some tasks, depending on what the sport had been, and there would be sex. Sometimes he would be fucked, and sometimes he would fuck his teacher.
Unfortunately, Mr Wood would be leaving at the end of the school year, so Phillip went into the holiday a bit despondent as he didn't know where he would get sex. Then he was on holiday and saw two other boys sucking each other off through a bedroom window. Then he smiled, as he knew what he was going to do next.