The Jockstrap
Chapter 1
Jake was excited about starting his new job at The Harper Group, a local accounting firm that had recruited him during his final semester in college. Jake had graduated near the top of his class, but the economy was not in great shape and most firms were either not hiring or were actually laying off employees. When The Harper Group approached him, he enthusiastically accepted despite having to relocate from his hometown across the country to San Francisco. His girlfriend, Monica, had come with him in hopes that she could find a job as a teacher. Both Jake and Monica were under considerable student loan debt, so the new job was a blessing. Monica was able to find a position as a teacher’s aide, until a teaching spot opened up at the local elementary school. They found an apartment within their price range, although it was not in the best part of town. By Sunday evening, they were moved in and Jake prepared for his first day on the job by looking over some of his old accounting texts. He had not yet taken the CPA exam, but the firm assured him that they would find something useful for him to do.
He arrived the next morning and was greeted by the recruiting director, Phil Harmon, who took him to his new office. The office was small, but it had a nice desk and a window that looked out over the alley. “You have a meeting with the section head, Jeremy Wallace, at 9:30am and lunch with two other associates, Paul Blake and Tim Martin, who had both started the year before. It struck Jake as a bit odd that the office seemed completely devoid of women. The receptionist was male, the secretaries were male, indeed everyone that he met was male. He dismissed it and figured that there must be some female employees, but that he had not seen them. Jake got settled in his office and unpacked the briefcase that his girlfriend had given him as a present. He put his possessions in the drawers of the desk, but noticed that the bottom drawer was locked. He made a personal note to see about getting a key. He looked at his watch and noticed it was almost 9:30. He did not want to be late for his first meeting. He grabbed a pen and legal pad and walked toward Mr. Wallace’s office.
Jake knocked on the door. It was answered by a man in his early 50’s with graying hair, but still physically fit. “Good morning, you must be Jake. I am Jeremy Wallace, but my friends call me Jerry.” Jake shook the extended hand, which was like a vice grip and followed Jerry into his office. Jerry closed the door behind him. “Please take a seat.” Jake did so. The office was easily twice the size of his with a view looking toward the Bay. As Jake glanced around the office, he noticed two black and white photos depicting two men engaged in BDSM activities. I guess Jerry is queer he thought to himself. “I hope that your first day is going well Jake.”
“Yes, Sir.”
“Please, Jerry is fine. We are not super formal here at the Harper Group. More like a big family. I have a couple of projects I would like you to begin to work on. I know that you have not taken the CPA yet, but no worries, I would still appreciate your analysis of the management of these two accounts.”
“Yes, Ss…Jerry.” Jerry smiled.
“Now you’re talking. I understand you are lunching with Paul and Tim. I have assigned Paul as your mentor. He has been here a little over a year and knows the ropes. Listen to what he has to say and follow his advice. I hope your enjoy lunch. The firm dining room has a pretty good selection and you can get takeout as well. Oh, and by the way, if case no one has told you, we have a pretty strict rule here. Between 2:00 and 3:00pm, everyone stops work and relaxes. We call is ‘Rest Time’. We have found that it allows everyone to destress. It means no phone calls and no work-related activity. Some folks meditate and others simply nap. We have several relaxation files installed on your desktop and I would like you to try those for the next week or so. They should help you relax and feel good.”
“Yes, Jerry.”
“Good boy.” Jake thought it odd that Jerry referred to him as a boy, but figured it was just a turn of phrase. Jake returned to his office and began looking at the files from Jerry. They were substantial and he figured that it would easily take several days to prepare an analysis. About 11:00am, Phil knocked on the door and stuck his head in.
“Settling in okay?”
“Absolutely. Everyone has been really nice.”
“I’m glad. It’s always exciting to have new boys join us.” There was that word again. Jake was in his mid-20’s and hardly a boy.
“Phil, the bottom drawer in my desk is locked. I was going to use it to store some stuff.”
“Let me see if I can find a key and get back to you.”
“Sure, no rush.” With that Phil disappeared down the hall and Jake resumed his reading. About 12:30, there was a knock on the door and Paul and Tim were standing there.
“Hope you’re hungry. Monday is meatloaf at the dining room, although you can get whatever you like. Jake pulled on his coat and followed them up in the elevator to the top floor. Jake was impressed by the dining room’s white table cloths and silver. They took a seat and had a nice lunch. Jake was full of questions and Paul and Tim did their best to advise him. Tim kept looking at his watch.
“Guys, it’s getting close to 2:00pm, we need to get back to our offices for Rest Time.” Paul nodded.
“Just remember Jake, if you are in the office and even if you are out of the office, Rest Time starts at 2:00 and lasts until 3:00. No work is permitted. No phones calls will be connected by the front desk. Rest Time gives all of us a chance to relax. You should use the relaxation files installed on your computer. They will really help you.” Jake was back in his office by 1:58. Two minutes later, he heard the sound of a gong over the intercom. This will followed by the sound of the individual office doors being closed. He closed his door and clinked on the folder entitled “Rest Time Relaxation Files”. The folder contained four files. He put on a set of headphones and clicked on the first file entitled “Relaxation for Good Boys”. He was still uncertain why everyone was referring to men as boys, but what the hell. He clicked on the icon and the file began to play. He could hear soft music and the voice told him to just watch the spiral on the screen and relax. The more Jake relaxed, the sleepier he became. Eventually he drifted off the sleep. When he woke, it was almost 3:00pm. He felt very refreshed and for some reason, a bit aroused. Promptly at 3:00pm, the same gong sounded and the hustle bustle of the office restarted.
The remainder of the week was pretty much the same, although Jake brought his lunch rather than going to the dining room. He and Monica needed to save money and the dining room was not cheap. Jake listened to a new file during each Rest Time and they all had the effect of making him drift off the sleep, only to awake in a state of increased arousal. By Thursday, Jake had to fight the temptation to pull down his pants and stroke his cock. When Paul checked on him on Friday morning, Jake asked him to close the door to his office. Paul obliged. “Is anything wrong?”
“Not really. I am enjoying the work, but I don’t know what is happening to me during Rest Time. Every time I listen to one of those files, I drift off the sleep and my dick gets hard.” Paul smiled.
“Nothing to be worried about. I happened to me too. Just an involuntary response to the file.”
“I don’t understand why I would get aroused and feel like I have to jack off from listening to some relaxation file,” Jake said. Paul shrugged. During Rest Time, Jake clicked on the final file which was entitled “Obedience for Good Boys.” As with the previous files, he dropped into sleep quickly, but this time his hand pulled down his pants and he began to stroke his hard cock. It felt so good. This was what good boys did. When he awoke, he was at peace. Obedience felt really good. When he reached down, he found that the bottom drawer to his desk was now unlocked. In it was a package with his name on it. Upon inspection, he found that it contained six white jockstraps in his size. How odd. And yet, he was beginning to feel aroused again. He was beginning to wonder just what kind of business he had joined. He decided to talk to Paul again.
“I’m sorry to keep pestering you with dumb questions.” Paul smiled.
“That’s why I’m your mentor, so you don’t have to ask dumb questions to other people. What’s bothering you?”
“Well, remember when I said that the bottom drawer on my desk was locked?” Paul nodded. “Well this afternoon it was unlocked and I found a package with a bunch of jockstraps in it.” Paul shrugged.
“So, what’s the problem?”
“I’m sorry, wouldn’t you think it was strange if you found a package of underwear in your desk?” Jake said, trying to mask his sarcasm. Paul smiled.
“It’s a gift from the firm. We all received jockstraps our first week. You see, one of the firm’s big clients manufactures the jockstraps. The firm likes to support its clients and provide its employees with a nice benefit. The jockstraps are super comfortable, you should try one on. When I came to work here, I always wore boxers, but once I tried on one of the jockstraps, I was hooked. They are super comfortable and wearing a jockstrap is much healthier than wearing regular underwear. No big deal. Jake rolled his eyes.
“So the firm is telling us what kind of underwear we should wear?”
“Not exactly. It would be preferred if you wore a jockstrap, but it is not mandatory. Give it a try. If you don’t like them, go back to your regular underwear.” Jake nodded. “By the way, Jeremy would like you to come to my office during Rest Time tomorrow. There is a special file he would like us to watch together.”
“Sounds good.” Jake returned to his office and finished his work for the day. He stuck the package of jockstraps in his coat and headed home. When he got home, Monica had left a note that she was going to the movie with a friend and would be back late. Jake pulled the package of jockstraps from his pocket. Taking Paul’s advice to heart, he decided to try one on. The worst that could happen was that he hated it. He removed his slacks and his boxers. His penis was still semi-erect. When he removed the jockstraps from the package, he noticed that the waistband was embroidered with the words “Good Boy”. He assumed that was the brand name. The jockstrap felt soft but also firm as he stepped into it. He pulled it up and it fit perfectly, cupping his balls and accommodating his penis nicely. The waistband provided nice support. Jake couldn’t remember wearing a jockstrap since high school gym class, but now he wondered why not. This was so comfortable. It even felt as though it was massaging his penis and his balls. The longer he kept it on the better it felt. Monica would not be home for a while, so he decided to leave his pants off and just enjoy the jockstrap. He also removed his shirt and walked around in the apartment in his new jockstrap and socks.
Monica called about 11:00pm and said that she and her girlfriends were going to grab some coffee before she came home. Anticipating a busy day, Jake told her that he was going to turn in. Normally, Jake slept in pajama bottoms or sweats. It seems a shame, however, to remove the jockstrap since it felt so comfortable. Besides, it was stimulating his penis and he was now hard as a rock. He slipped into bed with just the jockstrap and was soon fast asleep. The rest of the night, he had a series of erotic dreams where he was with other young men wearing only jockstraps and playing with each others’ cocks.
By the time that Jake arrived at work, he was a bit sleep deprived due to his dreams. He saw Paul in the lobby and he reminded him that he needed to come to his office during Rest Time. Jake did not mention the fact that he was now wearing one of the jockstraps under his dress pants. It was all he could do to hide his erection. Damn but the jockstrap made him feel good. Jake ate his lunch in his office and about 1:50pm, he walked to Paul’s office. Paul waved him in and had him sit in his chair in front of the computer. Promptly at 2:00pm, the gong sounded and Rest Time began. Paul clicked on a new file on his desktop and it opened revealing a multicolored spiral. “Just watch the spiral Jake, let it relax you.” Jake did as he was told and began to look deeply into the center of the spiral. He found himself relaxing. Paul pulled up a chair next to Jake, but Jake was now completely focused on the spiral. “Good boys obey,” Paul whispered.
“Yes, good boys obey,” Jake said in a monotone. Paul smiled.
“Good boys strip, except for their jockstraps and socks.” Jake stood and removed his shirt and dress pants revealing his new jockstrap. “Good boy,” Paul said. “Just relax. How does your jockstrap feel?”
“It feels wonderful Sir.”
“Good boy.” Paul extended his hand and began to stroke Jake’s erect penis through the material of his jockstrap. He could tell by the sharp intake of breath that it was giving Jake plenty of pleasure. “Just relax and enjoy having your penis stroked. Good boys obey and feel pleasure and you are a good boy.”
“I am a good boy,” Jake repeated.
“Good boys obey and do as they are told and you are a good boy.”
“I am a good boy.” Paul slowly pulled back Jake’s jockstrap, so that he could stroke Jake’s penis. Jake began to moan. “When you cum, you will become a good, obedient boy who does what he is told to do.” Paul increased his pace until he knew that Jake was ready to cum. “Are you ready boy?”
“Yes, Sir. I am ready to become a good, obedient boy.” With a couple more strokes, Jake’s cock erupted spewing cum on his chest.”
“Good boy. Now, I want you to collect all of your cum and eat it. Good, obedient boys love the taste of cum.” Jake used his fingers to collect all of his cum and then licked them clean. To Jake, it tasted like honey. “From now on, whether you are in trance or awake, when you hear me say ‘good boys obey’ you will do exactly as you are told without hesitation. Is that clear Jake?”
“Yes, Sir.”
“Good boy. Waking in 5-4-3-2-1.” Jake’s eyes fluttered open. He took a deep breath.
“Wow,” he said.
“Better get dressed Jake, Rest Time is almost over.” Jake dressed. As he tied his shoes, the gong sounded and Rest Time was over. He headed back to his office. He felt wonderfully relaxed and happy. Paul headed over to Jeremy Wallace’s office and knocked on the door. Jeremy waved him in as he finished a call.
“Is our newest employee a good boy now?”
“Yes, Sir. Jake now belongs to us.”
“Wonderful. Why don’t you bring him by my office around 5:30. It’s been a rough day and a nice blowjob by a set of fresh lips would do wonders for me.”
“Yes, Sir. We will be here at 5:30pm.” Meanwhile, Jake’s new jockstrap continued to pleasure his penis. He wasn’t sure he was going to be able to concentrate on his work. He received an email from Jeremy telling him that he needed to stop by his office at 5:30pm. Wonder what that’s about, Jake thought.