Tom Brown's School Days

Tom Brown's School Days

Chapter 4

Michael Adler approached Tom the next day.

"Tom, I was serious with my offer. I want to take you to bed and make love to you, just once."

Michael was a senior and looked even older than his eighteen years.

"I think I would like that Michael. How do you want to play this?"

"I will give you $1,000 and that will give me free use of your body for up to two hours. You may not then object to, or renege on our agreement."

Tom couldn't see any harm in that.

"Ok Michael, when?"

"Tomorrow after supper, and you come to my room."

Tom was looking forward to this macho guy making love to him, forgetting how big he thought the cock was. That state of affairs lasted about five minutes after he arrived at Michael's room the next night.

"Undress me Tom, then I'll do the same for you and take you for a shower, but first you are going to have several douches. I'll manage them and stop when I am satisfied."

Tom thought the douches were a good idea so no argument. He undressed Michael and by the time he was naked Tom sat back on his haunches and mouth agape, eyes nearly popping out of his head, his brain told him he was in serious trouble. The hard cock presented to him was enormous. Tom had seen and played with Brian's, that was very impressive but this one was even longer and fatter. It wasn't an ugly cock, it just looked as though it would have looked more normal on a ten foot tall man.

"I will be as gentle as I can Tom but I intend to bury every inch of my baby in your cute butt."

Tom was actually frightened by what he could see.

"I will open you up with my fingers and then move to dildos until you are taking one only a little smaller than mine. You will be able to watch it all because of my mirrored ceiling."

Tom looked up then and realised that Michael had hung a six foot square mirror above his bed.

"On the bed, Tom, on your back. I'm going to secure your legs in the position I want. You will be comfortable then instead of having to keep the position yourself."

Michael took two padded ankle restraints, fixed them to Tom's ankles and pulled them back one at a time securing them to the corners of the bed. The result was Tom spread as wide as he could tolerate. His knees were bent, lowered so that they were almost on the bed at the side of his shoulders. Although his arms were free he was in effect helpless. When Michael produced a camera and took a load of pictures, Tom couldn't do anything about it.

"I want a record of this Tom, you are just so bloody sexy."

Tom watched as Michael set up a camcorder at the end of the bed, but at an angle so that it would have an unobstructed view as Michael started fingering him. Obviously playing to the camera, Michael spread Tom's anus with his fingers before releasing the cheeks and continued to finger him. Watching the action in the overhead mirror was embarrassing and then he noticed the screen off to his left as it came alive and the picture being taken by the camcorder was being shown live. That started to fascinate Tom as Michael increased the number of fingers until he had all five inside him rotating them and fucking him with them. Michael stopped then and moved the camcorder round to the side more and raised it on its tripod so that it was looking down at Tom from just a little back from his ass. Then Michael started tonguing Tom's anus. It felt amazing and was such an erotic turn on watching the camcorder recording. His cock and balls had never looked so hard or so big. The sensations being felt all through his body soon made Tom forget his embarrassment. This was sex like he had never imagined. Michael didn't slacken his erotic attack on Tom for what seemed hours. The next piece of action was quite humiliating for Tom, but still looked amazing as Michael picked up, and lubed the first dildo. It was about seven inches long and six inches round. It entered him and Michael let it go all the way in because Tom didn't flinch. He was fucked with that for a few minutes and Michael was able to use his free hand to move the camcorder round showing the fucking from different angles. He did the same with two more dildos, each one bigger than the last so that when he thought it was time for a real cock the difference in size was not all that much. Tom had several orgasms during this period because the dildos were striking his prostate every time they entered him. Michael then lubed himself and positioned to enter Tom. He moved the camcorder round so that it would see the penetration unobstructed. Knowing that Tom would feel considerable pain as he entered him, Michael fell forward onto his arms and kissed Tom as he pushed his glans over Tom's sphincter. Tom did scream but it was completely muffled by the kiss. When he felt Tom begin to relax he knelt back up and told Tom what he was going to do.

"I know it will hurt again Tom, but I'm going to pull out completely and enter again so that the camcorder can pick up the actual entry, but the same as this time I will hold still until I feel you relax."

Tom didn't like the idea, but what could he do. Breathing deeply to help him relax he was able to take the second penetration without screaming but the pain was still quite acute. Michael remained still for a long time just stroking Tom's cock to bring it back to an erection, and then he played with the balls as well before starting the slide deeper into Tom's bowels. When he felt the second barrier he just placed his hand over Tom's mouth and spoke to him as he entered the intestine.

"I'm sorry, I know this is hurting, but I promise it will get easier each time I do it."

Michael then started what for him was the most amazing fuck he had ever given. No other lover had taken all of him, the entry to the intestine just being too much pain. But Tom had been taking quite a few cocks where the intestine had been entered so he guessed that although it would be painful it would be possible, particularly as the dildos had been long enough to do the job as well. Summoning all the control he could, Michael lasted for ages before speeding up for a massive orgasm. He wasn't worried about Tom because he could see he had cum. His prostate had taken so much punishment from Michael's massive cock that he had orgasmed several times.

When Michael had calmed down a little, he pulled out of Tom and immediately picked up the cam to record directly on to Tom's anus, catching it before it closed up. Michael thought he would be able to orgasm every time he watched this bit of the DVD that would come out of it.

"I'm going to punish you now Tom, just for the benefit of the recording. I won't hurt you much, but I want to see a red butt. No bruising. It rounds off the film very nicely I reckon."

He released Tom's legs and told him to turn over and rest on his knees, well spread and with his shoulders on the bed. Michael was so turned on looking at Tom's butt in that position that he added dialogue as he spanked him, intending to go again for a second fuck.

"You were not very good Slut, so I'm going to spank you and fuck you again."

Tom felt the slaps more than he liked, they were quite hard and then Michael climbed up onto the bed and entered him again.

"Now work your muscles to massage my love stick or you will get ten more."

This second fuck brought tears to Michael's eyes. He couldn't believe how good it was after the first one. All finished and Michael rolled Tom over, lay down beside him and cuddled him.

"That was bloody marvellous Tom. I know you don't really need the money, but if I offered you another thousand, could I do this again some time."

Tom looked into the eyes of this new lover and saw the lust, plus a little of what he saw in Adie's eyes all the time.

"I would love to Michael, but do you think that's a good idea? I love Adrian and I don't see that changing."

Michael wasn't stupid and dropped his eyes before replying.

"Probably not, but I would still like to do it again. I'll have to learn to live with the fact that you are just going to be a friend with benefits."

Tom laughed at that.

"I'll be that happily without the thousand dollars, but understand it will not be very often."

"Oh thanks Tom, I reckon I can live with that. Let me take you for a shower again now and then it will be time for bed I reckon." Tom nodded and thought about going back to his room and spending the night wrapped in Adrian's arms.

********** Adrian looked worried as Tom entered his room until he saw the smile on his face.

"I assume from the look that Michael was good to you."

"Oh yes, but Adie, you would never believe his cock. It makes Brian's monster look quite small. I have never seen anything like it. I was really frightened, particularly once he had restrained me so that I couldn't get away."

"He tied you up?"

Adrian's eyes were out on organ stops at that disclosure.

"Yes, but it was comfortable and he took ages opening me up with bigger and bigger dildos until when I took him the pain was only there for a few moments, then he slowly penetrated me until I was taking all of him. He was more than a foot long and incredibly thick. He recorded it all on camcorder so I am going to try to get him to burn a copy for me and then you will be able to see that I'm telling you the truth."

Too much for Adrian, he pulled Tom into bed and made love to him. Well, to be honest, he kissed him a few times before lubing them both and sliding into Tom for the quickest fuck he ever had. Tom thought it was funny.

"I must tell you raunchy stories every time I want a quick fuck. I loved that Adie."

Adrian blushed, he felt guilty having almost raped Tom it was so fast.

************* The next day, Tom asked Michael for a copy of the action of the previous night.

"Adrian doesn't believe what a huge cock you have so I could show him. Also I bet it is so erotic watching it from what must look like an out of body experience."

Michael laughed at that, and then had another thought.

"I'll burn you a copy, but you have to watch it with Adrian and me present, and then have a threesome after it finishes with me in control."

Michael was grinning and Tom joined him.

"I'll have to ask Adie, but I love that idea. I could be spit roasted then by two gorgeous men."

***************************** Tom should have spent more of the next day concentrating on his schooling instead of thinking about sex, then he might have avoided falling foul of a teacher meaning a trip to the principal's office.

******************* "Mr. Brown, I thought we had made a deep enough impression on you at the time of your induction that I would only see you again to wish you good luck and goodbye. Now I am going to have to consider something special to make sure I don't see you for a third time for punishment. While I think, you may disrobe for me and return to where you are now at display."

Tom resigned himself to more punishment and humiliation. He just hoped he would avoid the clinic. Naked as ordered, he watched the principal as he walked round his desk and then walked round Tom.

"Ah yes. I have heard stories about your amazing bottom. They are definitely well founded Brown. I shall take great pleasure in seeing that used and abused for this punishment. I will have to give some thought to the participants for this session. While I do that you may play with yourself so that I can look at an erect penis while I think."

Tom felt acutely embarrassed playing with himself in front of the principal but still managed a good erection quickly. While he was playing he heard the principal talking to someone on the phone.

"Bring in the special bench and see if you can find my son and the new physical trainer."

Tom was both curious and apprehensive about the special bench, and the additional two men. When it came he looked in terror at it. There were way too many gadgets on it for his liking, none of them good.

"Get up on the bench Brown, you can see where to place your legs."

Tom did as asked and waited. The principal walked round his desk and alongside the bench.

"Now slide down about another six inches."

Tom knew his arse was hanging over the end now. The principal then strapped him at the waist, quite tight, and with a narrow strap, strapped his calves into the stirrups and his hands into restraint at the side of his arse. His head rest was adjusted so that his head was at an angle of about 45 degrees to the horizontal, making it easy for him to suck cock he guessed. The principal opened a cupboard under the bench and withdrew a dildo.

"This is a cast of Michael Adler's penis, Brown. You will be very familiar with it by the time you leave here today."

He also laid out on his desk several chastisers, none of which appealed to Tom. Fortunately there were also a couple of tubes of KY so at least he was going to be lubricated.

The door opened again and three females walked in. Tom gasped at this further trio of either participants or witnesses. He recognised Ms. Watkins, Mrs. Morgan, and he gulped at the third one, it was the pretty young receptionist he saw on arrival.

"Isabel, I have invited you this time so that if you wish you can explore Brown's body, find out what a man feels like before you indulge with a boyfriend."

"Thank you, Dad, I'm sure I'll enjoy this."

The other two ladies chose easy chairs and moved them to best see Tom until the action started when Ms. Watkins stood up and moving round Tom. He noticed she was using a small handheld camcorder.

The last people to arrive were the new sports master and a boy about the same age as Tom.

"Dwight, you can start. You have ten minutes to explore this boy's body. You can strip now or later, whatever suits you."

"Thanks, Dad I'll remain clothed for now."

So the father was going to allow his son and daughter to administer punishment and humiliation. Tom looked at him and scoped him out. About 5 feet 9 inches, Tom guessed, slim, nice looking guy. He was dressed in shorts and T shirt only, and Tom could clearly see the outline of a cut cock with a substantial head. `That should feel good if it doesn't get too enormous', was Tom's thought.

Dwight picked up a controller and used it to get the stirrups well spread and Tom's legs pulled quite a long way back, just raising his ass off the bench. His calves were horizontal and his knees were level with his eyes, spread wider than his shoulders.

"Suck my fingers, Boy."

Tom did, and knowing what they were going to be used for he made them very wet.

With no preamble, Dwight slid a finger into Tom's arse. Isabel was stood next to the bench watching and switching her eyes from Tom's groin to his eyes, watching him blush scarlet as he got an erection. He realised that Dwight was no novice, he was hitting Tom's prostate every time, it felt good despite the embarrassment. An extra finger, and a hand started playing with him. He raised his head to watch and saw a smile on Dwight's face. It just kept getting better as Dwight added two more fingers and used his free hand to stroke and caress Tom's body. Isabel got in on the act then pulling Tom's ball sac further up his body thereby exposing his anus more with fingers sliding in and out.

"Is that as thrilling for him as us women doing it in our vagina, Dwight?"

"Mmm, I guess, but not having a vagina I can't be sure."

Brother and sister laughed before Dwight continued. He played with Tom's balls when his sister relinquished them and jacked his cock as well. It all felt so good, but terribly humiliating.

"Enough you two. He is here for punishment, not pleasure."

"Miles, I think ten with the paddle should do to start with. Remember he will be due some more at the end so keep them reasonably light for a start."

The new sports master grabbed a paddle and stripped off his shirt. Stood in just athletic shorts and trainers he looked incredible. Tom could see his semi hard cock sliding up his left side, it looked awesome. The strokes came in an easy flowing motion with the master moving back and forth so that Tom actually only took five on each cheek. He was pleased because they weren't soft. He looked at each of the women as they were administered and realised they all thought it was good.

"I think Dwight may well have opened him up enough, Miles, why don't you let him excite you for a few minutes and then you can have the first fuck."

Tom was rendered speechless by that comment. The man was patently carrying a huge cock between his legs and three women were going to watch it reaming out his ass. He started crying then. The shame was overpowering just at the thought.

Miles slipped off his shorts and came round to Tom's head and let his cockhead rest on his lips.

"I'm going in until I hit the back of your throat, then I'm going to fuck your mouth with that amount for a few minutes before entering your throat and getting you to swallow all of it. Learn to control your gag reflex and breath as I come clear of your throat each time."

Tom took it all in, but was still terrified once he had seen the erect penis in front of him. It was another monster, only about ten inches long, but so fat. Before moving round to his ass, Miles let his cock rest on Tom's lips for a minute.

"Just lick it gently Boy."

Everyone watched, fascinated as Tom licked the huge head. A few minutes of licking and Miles started to bury more of it in Tom's mouth. He gagged as it hit the back of his throat and then thought he was going to die as it buried itself in his throat. It was choking him but pulled out before he passed out. It got easier each time he swallowed it, but it was very uncomfortable and quite painful. Eventually, Miles pulled out. Round to his rear end and Tom felt the head at the entrance to his anus. The women and Dwight all moved round to watch the actual penetration. It felt amazing and despite the shame and humiliation, Tom's cock had to react to it, coming to full erection quickly. Miles then slid all the way in making Tom gasp as it went over the second barrier, the pain brought more tears to his eyes but he only moaned at it. A long slow fuck ensued with Isabel and Dwight taking turns to play with his cock and balls. The principal stopped the action before Miles could orgasm.

"Get Brown off the bench Miles and lower it a few inches. You can take Brown's place then and Brown will fuck himself on your cock."

Tom did fuck himself for a few minutes until Dwight moved in and lifted his legs so that he fell back onto Miles torso. Spreading Tom's legs very wide and pushing them back he realised what Dwight was going to do. He felt the pressure and then screamed as a second cock entered his ass. The pain was unbelievable and remained for some time as Dwight fucked him slowly. It did eventually disappear to be replaced by the most incredible feelings, his prostate took so much punishment that before he felt both men orgasm in his anus he had three quite violent ones.

Once again Tom found himself strapped down on the bench but now he had the dildo of Michael's cock in his ass. It felt good until Miles re-appeared with the paddle and standing at the end of the bench with Dwight at the side started to plaster Tom's cheeks with hard strokes, alternating cheeks but keeping clear of Dwight's hand that he was using to fuck Tom with the dildo. The sensuality of the fuck and pain of the paddling took Tom over the top for another orgasm before he passed out. When he recovered consciousness, Tom watched the head master strip. He looked round and realised that Dwight and Miles were the only ones left in the room now.

Dwight looked very embarrassed but Tom could see that he was frightened of his father. `I wonder if his whole participation has been at his father's behest,' was Tom's thought.

Tom watched as the man approached him and made him suck on his cock for a little while, gradually feeding him all of it. Once again Tom was having to take cock down his throat and control gag reflex and breathing.

"You are probably a little slack for me now Brown, but I might as well try that ass as well. You can lube my cock Son. Feel what a real man is like."

Tom took his time scoping out the principal realising that he looked quite young to be Dwight's father. (It would be some time before Tom found out that the principal was, in fact, only his step father and his mother had married a much younger man before she too had died, like his birth father). He carried about seven or eight inches of cock which Tom knew wouldn't hurt unless he was brutal. Brutal he was making Tom pass out with the pain. By the time he came to the man had finished. With Tom conscious again he had to lick the man clean, almost throwing up it was so disgusting.

"Another ten Miles, I think and then that will be punishment complete."

"Please Dad, I'm sure you'll damage him if you beat him anymore."

"In that case you'll be able to practice your wimpy skills on him."

Tom was terrified now as Miles picked up a cane. He had every right to be as the first one landed and he passed out. He was in and out of consciousness for some time. He heard Dwight screaming at his father to stop before finally sinking into a deep state of unconsciousness.