The Apprentice - Cover

The Apprentice

Copyright© 2021 by Elderly English Schoolboy

Chapter 22: Back at Chatterley Hall

BDSM Sex Story: Chapter 22: Back at Chatterley Hall - A young boy arrives at a prestigious and venerable boarding school for girls to start a new job - little does he know he is to be the school disciplinarian's apprentice!

Caution: This BDSM Sex Story contains strong sexual content, including mt/ft   Ma/mt   Teenagers   Coercion   NonConsensual   Fiction   School   BDSM   Humiliation   Spanking   Teacher/Student  

As I stepped off the minibus and into the Chatterley Entrance Hall - it was quite late and there were few girls about - I had to take off my overalls again. Sue took them and escorted me, naked, through the corridors of the school. I thought I was headed back to my glass cage of a cell, but instead she was leading me towards the Head’s rooms. The Head and Mrs Lodenheim were there - both looking very disapprovingly at my lacerated body. I was glad that I was by now so used to being naked around others that my penis was hanging limp.

“I can see that you have had some of your well-deserved punishments. To be on the safe side we will wait with your punishments here at Chatterley for a week. As it happens, there will be a punishment ceremony for delinquents sent to us from St Cuthbert’s, and it has been decided that you shall join this as if you were one of them - it will make matters more interesting. However, your final and most important punishment will take place some time later, when each girl that you have ever had occasion to punish at this school will have the opportunity to repay you in kind in a private and anonymous setting. The details are yet to be settled and will be explained nearer the time.”

Mrs Lodenheim then called in a trio of girls who were introduced to me as Clarissa, Eloise and Willow. “These girls will be in charge of you for the next few weeks. Clarissa is the Head Girl, you might have met her before, and Eloise and Willow have just been appointed senior prefects. They will now take you to your cell.”

I spent the next week, naked, exposed to the public gaze. However, once the novelty had worn off I was able to go to the toilet unobserved, with fewer and fewer girls bothering to watch me, until, from the second day onwards, hardly any ever did. I was basically in solitary confinement - one of the three girls brought me food, and took me to have a shower every other night. Other than that, I had hardly any contact. Willow was a very attractive girl my own age. Whenever she entered my cell and looked at me with that ironic smile of hers, I couldn’t help but develop an erection. I was still embarrassed by this, even after all that had happened to me. But the worst was the boredom. I wasn’t even allowed a book, let alone TV. Day after day with nothing to do and nobody to talk to. Hell.

So I was almost relieved when the time of the ceremony arrived. I was given a St Cuthbert’s school uniform. Once I had put this on, I was taken to a classroom that already had around eleven or twelve other boys in it. Sue addressed all of us:

“Boys, you are all here for punishment. However, as you know only four of you will be punished naked and severely - one in each age group. The others will get away with a simple public paddling on your underpants. We will determine those who will get the full dose of punishment by way of a number of contests. There are six of you in age group 13-15 and six in 16-18. The two losers in each age group get the full dose. Now, we’ll follow Clarissa onto the stage where you will all be introduced to the girls. The older age group will then take a seat by the side of the stage while we conduct the contests for the 13-15 age group. Any questions?”

I wanted to know what sort of contests she was talking about, but I figured I would find out soon enough. Better not to draw attention to myself.

Clarissa took the lead and the other two brought up the rear, with Willow immediately behind me. This was the first time, I found myself thinking for no good reason, that she was seeing me wearing clothes!

Once on stage, Sue introduced all of us. For each boy, she gave the girls the year he was in and what he had done to merit attendance at the assembly. I do not remember all the details, but what stood out was one 14-year-old boy who had been caught masturbating in class! The others were mainly repeated failure to do homework, being found in possession of pornographic magazines, or being caught smoking cannabis (in more than one case). When my turn came, Sue obviously made the point that I was there because I had abused the trust that the school had placed in me and that now the tables were turned. The audience booed and hissed.

Then us older boys were to sit down at the edge of the stage. The six younger boys were lined up standing next to one another.

“We’ll basically play two rounds”, explained Sue, “with the two winners of each round being reprieved and immediately paddled. We start with a quick-fire maths quiz, followed by a spelling bee. You will each answer a question turn - get one wrong, you lose unless more than one other contestant also gets one wrong, in which case we play another round with the three remaining players. Understood? Ok, let’s go then. You have each five seconds to answer.”

It was basically a times tables quiz, and the boys at first got all questions right. Two rounds in, the second boy in line did not answer ‘8x7’ fast enough and since everybody else answered their questions correctly, he was the first to ‘advance’ to the next round. A second boy had trouble with ‘8x8’ in the next round, and another also got an answer wrong in the same round. The three remaining boys kept going for a couple of rounds - they were good at this! - until one of them did not quite get the answer out in time and was also determined as a loser. The two ‘winners’ got the ‘prizes’ immediately: while the ‘losers’ joined us on chairs next tot he stage, they had to drop their trousers, facing the audience, and then take turns bending over a punishment horse where they were paddled ten times. They took this stoically. Then the next round proceeded along the same lines, just with spelling. The words started off easy but soon the first boy was stumped by ‘chrysanthemum’, the second following soon with ‘chauffeur’. The two remaining boys were, again, paddled on their underpants but allowed to stay otherwise dressed. The boy who did not know his botany then was the first to get fully naked on stage. His erection earned him an immediate escalation, though nobody knew yet what was being escalated.

Sue then announced the punishment: “Rob will receive a whipping on his back with the no. 3 whip, followed by a caning with the no. 5 cane on his buttocks. The usual escalation for developing an erection before punishment is masturbation to climax in front of the discipline officer - in this case, of course, this will mean masturbation before all of you.”

So Rob had to sit on a chair at the edge of the face and masturbate. He was very hesitant at first, but then got into it and climaxed quickly. He was then strapped onto the punishment horse face down, with his legs spread and his bottom facing the audience. His hole and now flaccid penis were exposed for all to see. He was first whipped on his back - this made him scream badly - and then caned on his buttocks - this made him scream even more.

I was painfully aware that I was sporting a very prominent erection myself - masturbating in front of all these girls was not my first choice for how I was going to spend this afternoon, and I very much hoped that I would be able to survive the contests. But I did not have much hope. There was a reason I had left school after my O-levels at 16!

Ken, who was the next young boy to be punished in the nude, did not have an erection and was thus spared the indignity of having to masturbate in front of the audience of pubescent girls. But he did not take the whipping well, nor the paddling, screeching like a piglet being slaughtered.

And then it was crunch-time for me. I am good at my times tables, but for us more mature boys the task was rather more difficult: solving equations with several variables. I did not even know such things existed. The other five were doing their best, however, and the first two to finish submitted to their paddling, leaving the rest of us to battle it out for the remaining two ‘non-nude’ spots.

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