The Jockstrap
Chapter 2
When Jake arrived at Jeremy’s office it was almost 5:30 and his secretary had left for the day. The door was closed. Jake sheepishly knocked on the door.
“One moment please,” the voice of Jeremy called through the door. Jake hoped that he had not interrupted his boss. He just wanted to make sure that he was on time. A few minutes later the door opened and Jeremy motioned Jake into the office. “Please have a seat.” Paul was already sitting in the office. Jake took a seat and Jeremy closed the door. “So, Jake, have you enjoyed your time so far here at The Harper Group?”
“Oh, yes Sir. The work is very interesting and everyone has been so nice to me.”
“I’m glad to hear that. As Paul has probably told you, we are like one big happy family. I know it’s a bit intimidating as a new employee, but once you learn what is expected of you, you will settle in nicely. Oh, and by the way ‘good boys obey.’ Instantly, Jake’s head dropped to his chest and he slumped in his seat. Paul was beginning to undress and was soon standing in his jockstrap and socks.
“Now, Jake, do you hear me?”
“Yes, Sir. I hear.”
“Good boy. I think you would be much more comfortable if you removed your clothing. You may leave your jockstrap and socks on.” Jake immediately began to unbutton his shirt and then slipped out of his pants. Soon he was standing in only his new jockstrap and his white socks. “Good boy Jake. Very good boy.”
“Thank you Sir.”
“One of the things we pride ourselves on here Jake is good training. We want our new employees to be thoroughly trained and to understand what is expected of them. We want you to be comfortable doing what is expected of you even if some of the things we ask you to do are things you have never done before. For example, I might ask you to give me a blowjob or to allow me to fuck you. I want you to be comfortable or even enthusiastic about performing those functions even though they are new to you. Have you ever had sex with another man, Jake?”
“No, Sir. I am straight.” Jeremy smiled.
“That sounds exactly like what Paul told me a year ago. And yet, with the proper training, Paul has become a wonderful cocksucker. Isn’t that right Paul?”
“Yes, Sir. I love to suck cock.”
“And you thought you were straight too, didn’t you?”
“Yes, Sir. I had been marries about two years when I came to the firm. Once I learned what was expected of me, it became clear that I was actually gay and there was no longer any reason to pretend. My wife agreed to a divorce and now I live with my boyfriend, Carl. We hope to get married soon.” Jeremy nodded.
“So working at the firm has made some wonderful changes in your life, true?”
“Yes, Sir. I am grateful to you and the firm for training me properly.”
“Good boy. And do you think that Jake would benefit from the same training?”
“Absolutely Sir.” Jeremy removed his shirt and his pants.
“Jake, I want you to watch Paul as he gives me a blowjob. Learn from him because in the next couple of days, I will expect you to give me a blowjob as well. Is that clear?
“Yes Sir.” With that Paul stood and walked over to Jeremy. He got down on his knees and pulled down Jeremy’s jockstrap. He then began to lick his balls and his shaft. Eventually, he worked his way up to lick the head and then to take the head in his mouth. As he began to suck. Jeremy moaned with pleasure. Paul continued his ministrations. Finally, Jeremy exploded into his mouth and Paul swallowed.
“Good boy, Paul. Now, see how easy that was Jake. Boys like you and Paul need as much cum as they can get. It makes you more submissive and obedient. Now, Jake, please stand and place your arms at your sides.” Jake did as he was told. Jeremy walked from behind his desk. His cock was still hard and covered in a layer of cum. He stood next to Jake and pulled down his jockstrap. Jake’s penis sprung out. “I’m glad to see that watching other men have sex arouses you. He then grabbed Jake’s balls and gave them a squeeze. Jake grimaced, but did not say a word. In his mind, he knew that it was Jeremy’s right to inspect him and to touch him as needed to satisfy himself that Jake was a good boy. “Jake, please place your hands on my desk and bend forward.” Again, Jake did as he was told. He could hear that Jeremy had squirted some lube on his hand. He then worked one finger inside of Jake’s hole, then another and then a third. Jake could feel incredible pressure and then Jeremy found his prostate. As he massaged it, waves of pleasure ran through Jake. He began to leak precum.
“That feels good, doesn’t it Jake?”
“Oh, yes Sir. It feels wonderful. Please don’t stop Sir.” Jeremy smiled.
“You see. Learning new things can be fun. Can you imagine how nice it will feel to have my cock fuck you? I remember the first time I fucked Paul. Once you have had a real man’s dick inside you, there is no going back.” Paul nodded. Jeremy reached into his desk and pulled out a 10″ dildo. “When you wake up Jake, you will have a strong urge to practice your oral and anal skills. I want you to use this dildo to do that. Is that understood?”
“Yes, Sir.”
“Good boy. You may put your clothes back on.” Jake did as he was instructed. Paul also put his clothes back on and they both took their seats. “I am going to count down from 5 to 0. When I reach 0, you will be alert and awake and feel totally refreshed. You will not remember what happened in trace, but you will start to question your sexual orientation. Sex with other men will become increasingly attractive to you and sex with women will begin to become repulsive. Do you understand, Jake?”
“Yes, Sir.”
“Good boy. Now waking in 5-4-3-2-1 and 0. Wide awake.” Jake’s eyes fluttered open and he took a deep breath. “Jake I am so delighted to hear that your time here has been rewarding. You are a smart boy and I know you will fit in well.” Jeremy stood and escorted Paul and Jake to the door. “I hope both of you have a nice evening and I will see you tomorrow.” Jake followed Paul down the hall.
“It’s so nice working for someone like Jeremy,” Jake said. “He seems to really care about training us and helping us to become comfortable here at the firm.”
“Yes, he is a wonderful boss and I hope you enjoy working for him as much as I have. Good night, Jake.”
“Good night, Paul.” Jake headed back to his office. At that point he noticed that he had a dildo in his hand. This struck him as perfectly normal and he promised himself that he would spend some time using it. It was nice to know that Jeremy had so much faith in him as a new employee. He did not want to do anything that would disappoint Jeremy or Paul. He stayed another hour and finished a small project and then headed home. When he got home Monica had gotten Chinese including his favorite, Kung Pao Chicken. Strangely, he wasn’t really hungry. When he changed out of his dress clothes, he noticed that he was getting a bit of a gut. That was the last thing he wanted. He thought to himself—good boys need to be physically fit. He needed to get back into going to the gym regularly and he made a mental note to ask Paul about a local gym. As he stood naked, except for his jockstrap and socks, he was amazed at how comfortable he felt. The jockstrap still caressed his penis and balls and provided wonderful support. He slipped on a pair of shorts and a t-shirt hating to cover up the jockstrap. He then went over to his underwear drawer and cleaned out all of his boxers. From now on, it was jockstraps or nothing. The jockstrap seem to reward him for the decision by massaging his penis to full hardness. God I love jockstraps, he thought to himself and wondered why he had ever opted for boxer shorts.
He wandered into the kitchen and sat down. He picked at his food. Eating Chinese food was not very conducive to getting in better shape. “What’s wrong babe,” Monica asked, “you usually devour Kung Pao?”
“Just stress from work,” he said. She got up from her chair and put her arms around him.
“I think I can help with that. How ’bout we spend a little quality time in bed?” She reached down and brushed his penis. Normally, this would have caused a spontaneous erection, but this time….nothing. Jake’s dick remained flaccid. In Jake’s mind, the thought of making love to a woman was now really off putting, almost nauseating. What had he ever seen in Monica. Needless to say, the lovemaking was short-lived and unenthusiastic. Monica just could not get Jake hard and finally gave up and rolled over and turned out the light. Jake began to stroke his cock through his jockstrap and instantly became hard. The rest of the night, he had erotic dreams of sucking off other men and having them penetrate him. He desperately wanted to stroke his cock, but decided that Monica might take exception to that given his poor performance. He decided that watching some gay porn might be just the thing.
When Paul stopped by his office, he asked about a local gym that he recommended. “You need to sign up at the gym two blocks down called ‘Gym Boys.’ It’s nice because it’s all male and they have coaches that will really push you. Just be prepared to devote time to your workouts. The coaches will not tolerate slackers. I have been a member since I came to work here and I can sponsor you. Jeremy was my sponsor and also sponsored Tim.”
“I’d like that. How do we get started?”
“Why don’t you meet me at the gym tomorrow morning? I start early, so you would have to be there at 5:30am.” Jake sighed internally. He usually slept until 6:30 or 7:00. But he knew that this was a change that he needed to make. Working out would improve his body and make him more physically fit.
“Sounds good. I will be there. What should I bring?”
“Just bring yourself and a change of clothes. The gym provides everything else you will need. At your first visit, you will need to attend an orientation session with one of the trainers. After that, you will be scheduled for workouts with an assigned trainer. Just remember, the trainers are not there to be your friend, they are there to push you hard to be a better boy.” Jake nodded. He knew that you could not achieve goals in life without hard work. He hoped that beginning to work out would impress Jeremy. The rest of the day was pretty unremarkable. Jake had to resist the temptation to use his computer to look at porn. His jockstrap continued to massage his penis and balls and kept him erect or semi erect most of the day. Finally, when Rest Time came around, he could not resist any longer. He closed his door and undressed to his jockstrap and socks. A quick Google search produced some porn for him to look at and he masturbated for most of the hour finally shooting his load. Something inside him told him that cum should never be wasted and he captured it with his hand and swallowed it. Although he could not recall the source, he remembered that cum was good for him. He managed to clean up and get dressed before Rest Time ended.
When he arrived back at the apartment, Monica was in a bad mood. “Babe, I don’t know what has gotten into you but you weren’t worth shit last night. I hope that whatever it is, you snap out of it.” Jake looked down.
“Sorry. It’s just the pressure at the firm. They keep adding assignments to my work load. I decided to go back to the gym starting tomorrow morning to see if I can get rid of some of my stress. Paul is sponsoring me at a gym close to the office. Only problem is that I have to be there at 5:30am. I’d better turn in early. I don’t want to be tired in the morning.”
“I hope it works. I want the old Jake back. The one that used to fuck my brains out.” Jake nodded. “By the way, Martha just texted me and she wants me to join her and Becky for a late movie. You don’t mind do you?”
“Nope. You guys have fun. I am gonna eat something and crash early.” Monica grabbed her purse and headed out the door. Jake looked at his watch. It was only 7:30pm and he figured that it would be at least 10:00pm before Monica got back. Jake headed back to the bedroom and dug into his underwear drawer and quickly found the dildo that Jeremy had given to him. This needed to be inside him. Jake rifled through the night stand and found some lube. He stripped down to his jockstrap and socks and generously lubed the dildo and his asshole. The dildo had a suction cup on the back end which allowed him to fix it to the bathroom wall. Once it was in place, he spread his ass cheeks and pushed slowly back on the dildo, allowing it to penetrate his hole. The pressure gradually gave way to pleasure and a fullness he had never experienced. It felt really good and he began to push it in and out feeling waves of pleasure. Finally, he came and used his hand to capture his cum. So this was what it was like to be a good boy. He showered and hid the dildo back in his underwear drawer under his jockstraps. He climbed into bed and drifted off to a wonderful sleep.