The Assistant Chapter 2
If a sexual scene involving male-to-male relationships offends you, then you should not read this story. You must be of legal age in your area to read this. This story will contain sexual acts between adults. As the story progresses it will include elements of domination, humiliation, forced sex, kink etc. Hopefully all the stuff that turns you on :) all rights are protected and the story cannot be reproduced without permission.
I arrived in the morning to find Tim already there looking like he had not slept all night. He came into my office and I instructed him to close the door. I told him how his actions had put me in a bad position and how it would be best for me and the company to make an example of him. I explained that turning him over to the police and making sure he was prosecuted and ended up in jail was in our best interest as a deterrent to future employee theft. He started to tear up again his blue eyes becoming moist pools. I went on to say how disappointed in him I was, how he had betrayed my trust and needed to be punished. I looked up to watch him crying. I asked him if he knew what happened to young cute boys like him in jail. How he was sure to be gang raped and abused over and over. That he would suffer unspeakable atrocities and humiliation and that many such boys ended up with AIDS or dead. I put on a documentary for him to watch about prison life. In it a new prisoner was gang raped by a group and forced to dress up as a woman. He was made into a drug addict and a whore, sold over and over again by his masters for cigarettes. The documentary showed him becoming a Prison Prang, a pussyboi having to shave his body and wear makeup. Serving a group of Black prisoners who beat him and whored him out. The story went on to show the boy in the prison hospital disfigured by his harsh treatment and dying of AIDS. Timmy could no longer control himself and was openly sobbing now. He again started begging me to help him. Saying he would do anything if only I showed him some mercy.
I told him that I had no desire to see him meet a horrible end or to bear any responsibility for his death. That said if he was not sent to jail it would become my responsibility to make sure he was punished in much the same manner but ensuring his safety and that no permanent harm came to him. I would take on the responsibility of seeing that he was treated much like he would be in jail so that he had this deterrent. If he agreed to do everything I told him without question he would need to sign a full confession and agree to follow all my instructions. He would in effect become my personal slave for the next five years. If at any time he did not do as I instructed I would have no choice but to turn over the tapes and his confession and make sure he suffered his fate. With a tremor in his voice he told me he would do as I say. That is not what I want to hear, what I want you to do is beg me to be your Master and tell me how you will do exactly as I order. With a tremor in his voice he said "Sir will you please be my Master and let me serve you in any way you see fit" I smiled to myself and thought this will be a lovely 5 years.
After Timmy had signed the confession and papers I gave him, I looked at him and ordered, "drop your pants and show your self to me". Timmy looked ashen but began to open his belt moving slowly as if to bide time and figure a way out of this dilemma. Get a move on I barked as he dropped his pants and stood there. Now the boxers I said, he lowered them with one hand using the other hand to shield his cock from my gaze. Move the hand away slave or the deal is off. He dropped his hand revealing his blond bush and his cut cock, which looked kind of shrivelled. "What a poor excuse for a cock" I noted it is barely more than a clit. How do you satisfy your pretty wife with that little thing." Now turn and bend and spread boi show me your hole. I watched him bite his lip as waves of humiliation and despair rolled over his face. Non-the less he turned and spread his cute hairless ass showing me a pink pucker with a few hairs. I grabbed a pair of tweezers I had brought and walked over ordering him to stand still and not make a sound. I began to pull out the hairs one by one as he cried both from the humiliation as well as the pain. "I like my boi as hairless as possible" I said but we have time to get into the details later. Now I want you to lie over my leather couch with your ass over the arm and your feet nicely spread on the floor. We are going to begin your punishment. I began with my hand smacking each of his cheeks five times. When I saw that was not having as much of an effect as I desired and was in fact stinging my hand I decided to use my belt. I wore a nice wide black leather belt on purpose that morning. Removing it from my belt loops I doubled it in half and administered the first spank delighted to hear his little cry of pain. I informed Timmy this morning we are going to give you 10 nice strokes with the belt on each cheek. You will count each stroke then thank me after each blow. If you forget to do so I will start all over from the beginning. Through his tears I heard Timmy quietly say: "One, Thank you Sir" I increased the force and my pace and let myself get into it as Timmy continued to count first crying out then thanking me as ordered after each blow. As I approached the end of the beating I was pleased to see how red his creamy white ass was becoming and how welts were starting to rise in the skin surface. After the last blow I ordered him to stop his blubbering and to go to his office. I instructed him to search on google for lessons in cocksucking and to practise what he read using a carrot or popsicle over lunch and his breaks and report back to me at 5:15 when I would be evaluating his skills as my cocksucker. "I am going to have to suck you?" he said with a tremor in his voice. Of course I replied I will take you through the experiences I anticipate you would experience in prison. You better please me boi or the deal is off." The boy's cute face looked humiliated, wet with tears as he said "Yes Sir" I watched him walk away gingerly and knew he would have trouble sitting on his sore ass all day, waiting for 5:15 to come around.
If you enjoyed this story you may wish to check out my earlier story on nifty Training My Jr. High Slut March 28, 2008. If you want me to continue this story email me with your comments or suggestions. If emailing it's nice to know your stats, where you are from and if you are a top or a bottom; pictures are also fun to get. My email is jam186200222@hotmail.com please put The assistant as the subject line. I do accept select sluts for training preferably in person but occasionally by cam. If you want to apply include a picture of yourself and describe your experience and fantasies.
Copyright 2008 James Marks This story may not be sold, nor made part of any collection without prior written permission, by the author.