Young Jimmy Ch. 01

Story Info
Assistant Jimmy assists in the bedroom too.
7.2k words
115.1k
19
0

Part 1 of the 3 part series

Updated 09/22/2022
Created 12/14/2004
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Mr. Michaels was a lonely bachelor that was quite wealthy. His job as the CEO for DigiTech, Inc. kept his wallet full but his heart empty. At 30 he had never had a serious relationship. He was too good of judge of character and knew that people just wanted to get close because of his money. Even if people came from other countries they had to know of him because of his high profile. But, he was a charitable person. His favorite charity was the orphanage he grew up. He was 5 when his parents were killed in an airplane crash and had no other relatives. He was a very bright child and did so well academically that he was noticed by a college recruiter. He managed to obtain a full scholarship and studied Business Management and became a skilled accountant. His education and risk taking helped him to become the CEO of DigiTech, Inc. Even after becoming successful he never forgot about the orphanage that treated him so well and supported his dreams. The Nuns at the orphanage tried many times to convince him to adopt but he thought his life would be too busy to adequately tend to a child. The children all loved him. He spent a lot of time and money at the orphanage. He loved to read stories to the children.

One day as he was reading he saw an older boy standing in the corner alone looking quite depressed. Mr. Michaels thought this boy looked too old to be at the orphanage. So, he decided to inquire about him. After story time he spoke with one of the Nuns about the older boy. He said, "Who was that older boy who stood by himself in the corner? He looked much too old to be here."

Sister Carry said, "Oh that is Jimmy. He just turned 18. He knows at 18 he has to leave. But we have agreed to let him stay here for a few more months. We are going to give him a nice going away party. Unfortunately there is not much of a future for him. He is not looking forward to leaving here and we worry about him."

Mr. Michaels sighed, "Does he have any talents? Any interests?"

She smiled proudly, "Yes! He is a wonderful helper. He helps us sisters with organizing, paper work and even with the children. He has been here with us for about 2 years but has always seemed to be busy helping us when you are around. He has a very high understanding of Mathematics. I feel had we of gotten him sooner we could have made something of him. He could have possibly even followed in your footsteps."

Mr. Michaels laughed, "Come now, there can only be one as special to you as me." They shared a laugh and then he asked, "How did he come to be a resident of the orphanage?"

She sighed, "His parents were scoundrels who were raising him to be one. A deal went bad and they were killed as he hid in a closet. He had just turned 16 when he came to us. We knew there was no chance of adoption but just couldn't turn him away. He has paid his way by working so diligently for us. He is a hard worker."

Mr. Michaels smiled, "I would like to meet this boy. Please, say nothing to the others but I may offer him a job after I spend some time with him. I want you to schedule every Friday at 7:00pm a meeting between him and me. With as much money and time I spend here I am sure the Sisters will not deny me this small request without them knowing why. I know I can not ask you to lie, but do what you must to not tell them, please." She happily agreed.

On the first meeting Jimmy had an attitude. He was not overtly disrespectful; he just kept a mean look on his face and answered with short almost snappy answers. It was obvious that he harbored a lot of pain inside. Mr. Michaels was very forgiving and remained calm. He asked Jimmy, "What do you plan to do when you leave here?"

He huffed, "Probably be a crook like my parents. It's all I know. It's not like I am going to own a company and get rich or anything."

Mr. Michaels chuckled because he knew Jimmy knew who he was. He then asked, "Well, Jimmy, did you know I grew up here?"

Jimmy's face softened a bit, "No. I didn't know that. How old were you when you came here?"

Mr. Michaels answered, "Five. I went onto college and became the successful man seated before you."

Jimmy sighed, "I came to a place with caring people too late. It is too late for me. But, I do know how to survive. I will survive."

Mr. Michaels was considerably larger than Jimmy in height and muscle bulk. As he sat before him he towered over Jimmy and for a moment enjoyed the feeling his size dominating over Jimmy. He had never before felt such an emotion and quickly shrugged it off. Jimmy exhaled, "So, why the interest in future criminal such as myself?"

Mr. Michaels sat back in his chair and took in the striking handsome yet youthful face of Jimmy. With a smile he said, "I don't think it is too late. You have the potential of becoming someone too. I just want to see if I can help you in the little time you have left here."

Jimmy rolled his eyes, "Another charity act for you?"

Mr. Michaels frowned, "I don't like your tone, kid. I just want to help you. You don't have to be so nasty. I mean you no harm. I am no threat."

Jimmy sighed and slouched, "What ever. Maybe if you return next week I will start to believe you a little more. I have to go now." He stood and Mr. Michaels stood and walked around the table to stand close to Jimmy.

He rested a hand on his slim shoulder and looked down into his blue eyes, "You are special. I can see it in you. Don't give up on yourself just yet."

Jimmy shifted his weight a bit and it was obvious he was nervous under the weight of Mr. Michael's strong hand. So, he removed his hand and watched as Jimmy walked away. He took in the slender shape of Jimmy and thought to himself. "Why do I find this kid attractive?"

Mr. Michaels might have been a busy man but he was lonely and had sexual desires. When sitting home alone he enjoyed watching Porno. He found he gravitated to Gay Porn and often thought perhaps he was gay and that was why he found no one he wanted to spend his life with. But, this night as he stroked his long and thick manhood he thought of Jimmy. He envisioned his handsome face, soft lips, blue eyes and his slim build. He then knew that he was indeed gay and wanted Jimmy. But, he decided it best to wait until he was out of the orphanage and he would have to play his cards just right. He knew when that happened he'd have to find away to be alone with him.

The meetings took place every week as planned and the two became very good friends. Mr. Michaels happily attended Michael's going away party at the orphanage. During the party when it came time for Jimmy to open the presents Mr. Michael's gift was saved for last. There was a box the size of a shoe box. Jimmy un-wrapped the gift and found two envelopes inside and a key. He looked confused as he lifted the first envelope full of money. Mr. Michaels said, "Jimmy, I am offering you a job as my personal assistant. That money is just a taste of what you can earn with me. You can keep the money even if you turn down my offer. The money is a late birthday gift. But, don't answer me until you have looked in the next envelope.

In the second envelope was a business card for a local tailor and gift certificates to use with the tailor. Mr. Michaels said, "That is my tailor and those are gift certificates for custom suits. You will need them to work for me. If you do not want to work for me, accept them as a late birthday gift. You will also see there is a key in the box. That key is to your own hotel room at the prestigious Khala Hotel. I have paid the room up for 3 months including room service of three meals a day. This too is yours even if you turn down my offer."

Jimmy and the Nuns all had tears in their eyes and seemed too stunned to speak. Jimmy finally asked in a squeaky voice, "How could I turn down your offer? Yes, I accept!"

One of the Nuns sitting next to him embraced him in a warm hug and said, "You have been blessed. I knew you were something special and Mr. Michaels saw it too. You be a good boy and work hard for him."

Jimmy said, "I will."

Mr. Michaels said, "Perhaps you ladies will let him stay the night and I will send a car in the morning to pick him up and take him to his Hotel Room." They agreed happily and Mr. Michaels thought to himself, "He will soon be my play thing. He will work hard in deed."

In the morning a limo came outside the orphanage and the Nuns saw him off. He was still in shock and awe as he sat in the limo. When he stepped into his Hotel Room he stood in shock as the Bell Boy looked at him and giggled. He looked at his clothing and knew he was unaccustomed to such a place. The Bell Boy said, "This place is wonderful. You will like staying here." He patted his should and nudged him forward, "Go on, this is your place for the next few months. You are in the right place."

Jimmy smiled and turned to him, "Thank you. It is wonderful."

The Bell Boy said, "Dinner is served from 4pm until 7pm. Should I schedule you for Dinner room service?"

Jimmy nodded his head yes, "5pm will be fine. What is on the menu?"

The Bell Boy smiled at his innocence, "There is a menu on the dresser. Look at it and call the kitchen when you decide what you want. Just make sure you call by 3pm. They stop taking meal orders one hour before that meal time begins. I'll be going now. You need to be left alone in here for awhile." Jimmy smiled as the Bell Boy left.

That evening after eating steak and fries for dinner, Jimmy's telephone rang. The person on the other end was Mr. Michaels and the conversation went like this:

Jimmy: "Hello?"

Mr. Michaels (MM): "Are you settled in, young Jimmy?"

Jimmy: "Oh yes, thank you Mr. Michaels! This room is amazing. I feel like a King in here. I don't even want to leave the room."

MM: "Well, you don't have to tonight. Just settle in and watch some television. Today is Thursday. I won't start you working until Tuesday. You have an appointment at 1pm with the tailor. He will get your measurements to make 10 suits for you. After the measurements he will help you in picking out the material. He should have at least one of them ready Monday. You will wear that suit to work Tuesday. I will have a limo sent to pick you up at 12:30. You got all that?"

Jimmy: "Yes, Mr. Michaels. I got it. I guess I'll see you Tuesday then?"

MM: "Yes. Oh and there is casual clothing store beside the hotel. You should spend a little of that grand to buy a few casual outfits and pajamas. And in the hotel there is an indoor swimming pool. If you want to use it, you should buy some swimming trunks as well."

Jimmy: "Ok. I will, Mr. Michaels. Thanks again for everything. I'll see you Tuesday."

MM: "Ok, young Jimmy. See you then."

Jimmy hung up the phone in disbelief of the apparent wealth he seemed to be living in. Mr. Michaels felt his own heart race as he imagined Jimmy in swimming trunks. He decided that one day next week he would come to the Hotel and go swimming with him just to see Jimmy in swimming trunks.

Jimmy took a nice long bath and crawled into bed. He retrieved the remote control from the night stand and turned the TV on. He soon came across a Porno channel. Jimmy did not know it but, such channels had to be paid for. This meant Mr. Michaels purposefully paid for porno channels. His motive was to hopefully fill young Jimmy's mind with thoughts of pleasure. And oddly enough, all but one of the channels was Gay porn. This was a subtle way of preparing him for his real purpose, Boy Toy. Jimmy was too uncomfortable to look and changed the channel.

The next day the fitting went well and Jimmy picked out many nice patterns. Mr. Michaels had a desk brought into his office and another telephone jack put in. He then had a nice phone hooked up, put notepads on the desk and filled a drawer with pens and pencils. This would be all his personal assistant would need to start off with. Mr. Michaels wanted his desk in his office so that when the day comes when he conquers Jimmy he can have sex with him in his office when ever he wanted.

That night Mr. Michaels masturbated while watching gay porn and thinking of Jimmy. The poor guy in the video was drugged by his boss and tied up on a bed. His boss had his way with the objecting young lad. By the end the submissive young man enjoyed the pleasure. Mr. Michaels was sure it could happen that way with Jimmy as his manhood exploded with cum all over his hand.

Jimmy was curious and found himself watching the porno. He had never seen any kind of sex and to see Gay sex was something very odd to him. He could not understand how anal sex could be pleasing for the person receiving. Even as both men moaned in pleasure he did not understand it. Yet the sounds of flesh slapping against flesh and the sounds of pleasure aroused him. He laid back and rubbed his hardened manhood. He found that the tighter and faster he stroked, the better it felt. Within a few minutes his first masturbation erupted in thick and hot cum like a cannon and then oozing on his hand. He panted and held his manhood as he felt it pulsating. He turned the movie off and then took a shower.

When Tuesday came Jimmy dressed himself and went to the lobby. He then hurried to the limo. The Limo took him to a black stone building with large silver letters about mid way up the 20 story building that read, "Digi-Tech, Inc.". He chuckled to himself, "I guess this is the place." The limo stopped and the driver came around to open a car door for Jimmy. He stepped out and thanked the driver. He looked up to the building as the driver closed the door and went around and got back in the driver seat and drove away.

As he stood there looking handsome in his dark blue suit with silver pinstripes Mr. Michaels walked out. He greeted Jimmy warmly, "Jimmy! I am glad to see you young Jimmy."

Jimmy smiled and said, "This is an impressive looking building."

Mr. Michaels chuckled as he put his hands in his pocket, "Yes it is. I remember when this company was nothing more than a small rented office space. It has grown. And you are a part of it now."

He pulled one hand out of his pocket and put it on Jimmy's shoulder and said, "Come. Let us get started. You are my first meeting of the day. We will be sharing an office. Since you are my personal assistant I want you to always be within arms reach. We will go to our office now." Jimmy nodded and Mr. Michaels led him into the building to the main desk. He said to the secretary there, "This is my personal assistant, Jimmy. I want a picture ID made for him today at 3:00. Call security and tell them I said to do this."

She smiled sweetly, "Yes, Mr. Michaels. I will put the call in now." She turned her attention to Jimmy and smiled as if she was truly happy for him, "Congratulations, Jimmy. You will love it here. Mr. Michaels runs a tight ship but he is a very good person to work for." Jimmy smiled and nodded to the pretty young woman.

Mr. Michaels smiled, "Good day, Miss. Smithwell." She nodded as the two walked away.

They approached the elevator and Jimmy gasped, "Wow. The doors to that elevator are beautiful!" He admired the golden doors with forest scene carved into them.

Mr. Michaels said, "Yes. I find them quite attractive as well. We paid an artist to make the carvings. He did an excellent job. I have never liked how most elevator doors look like slabs of steel." The doors opened and they stepped inside with plush royal green carpeting under their feet.

Mr. Michaels said, "Our office is on the 18th floor. The 19th floor is home to the two Vice Presidents of the company. My home is the 20th floor."

Jimmy looked puzzled, "The whole floor?" Mr. Michaels chuckled, "Yes, the whole floor. I'll give you a tour of it later if we have time." He then held out a key, "You will be given one of these keys. When you use it here-" He pointed to the keyhole on the panel above the numbers panel, "and turn, you will override the doors so that you can go straight to where you want to go without it stopping for others. Only I, the Vice Presidents and you will have such keys." He then used the key and pressed the number 18, "Just make sure you use the key before pressing any floor numbers." He then pulled the key out and waited for the elevator to go to the 18th floor.

Once there, they stepped out and the elevator doors closed behind them. Jimmy was led down a hall to a door with the number "1805". When the wonderfully carved oak doors were opened Jimmy saw an older woman sitting behind a desk. She was answering a telephone call and smiled when she looked up. As they approached Jimmy smiled at her as well. Mr. Michaels said, "This is my secretary, Mrs. Johnson. She has been working for me for 8 years now. She will be a lot of help to you."

Mrs. Johnson ended the call and looked up to the two before her and in cheery voice said, "Hello, Mr. Michaels. Who is this handsome young man with you?"

Jimmy felt himself blush and looked down at his feet. Mr. Michaels said, "This is the personal assistant I told you about, Jimmy. Jimmy, meet Mrs. Johnson." She extended her hand to him and Jimmy shook hands with her.

Jimmy politely said, "It is a pleasure to meet you, Mrs. Johnson."

She smiled as she pulled her hand back, "And it is a pleasure to meet you as well. Please, let me know if there is ever anything I can do for you." He nodded and Mr. Michaels led Jimmy to the door leading into his office just behind Mr. Johnson to the left.

He closed the door as they entered and waved his hand over to Jimmy's desk, "That is your desk. I will have a computer for you tomorrow."

Jimmy looked around, "This is a really nice office, Mr. Michaels."

Mr. Michaels sat in his leather covered executive chair and said, "Thank you, Jimmy. Please, have a seat here in front of my desk so that we can get started." Jimmy sat down in a simple leather chair in front of Mr. Michaels. Mr. Michaels cleared his throat and exhaled. He smiled and then said, "Jimmy, I am glad you accepted my offer. I have a good feeling about this and I can see the potential in you. I believe you are capable of pleasing me in your duties. Now, we have to discuss your duties. It is your job to ensure that I get all of my messages, you will be returning most of the calls for me, and you will ensure I have fresh coffee every morning. Mrs. Johnson usually handles that. But, get her to show you where everything is and how to do it so that when she is on vacation or out sick you can make sure I still get my coffee. You will run errands for me like picking up my dry cleaning or suits from the tailor. There will be all sorts of errands for you to run. You will also attend my meetings with me and take notes. Most of the people I deal with do not like recording devices but don't mind someone taking notes. You, Jimmy, will be instrumental in ensuring I have everything I need to stay organized and at the top. You must also be willing to do what ever it takes to keep me happy so that I can do a good job here. You will also do what ever it takes to help me out professionally when I need you to. Do you understand all this? Do you agree to do what ever it takes to keep me happy, organized and on top?"

Jimmy did not know that Mr. Michaels meant much more by "do what ever it takes to keep me happy" than he thought. He was so excited to have such a prestigious job that he excitedly nodded his head and said, "Yes, anything! I am so grateful to work for you, Mr. Michaels. I will do anything you need me to."

Mr. Michaels leaned in a bit with a serious look on his face, "Good, Jimmy. I'd hate to fire you and put you out on the streets because you falter in your duties. I am happy to have you aboard and see much potential in you. However, I will not tolerate failure or being questioned. I know this sounds rather brash, but I need to make sure you understand. Do as you are told and expected without question or risk losing your job."

12