The BootBlack

"Good job, boy. VERY good job. I think I've found my boot black. Actually, maybe more."

Charlie leaned forward and wrapped his arms around Foster's waist, leaning his warm, flushed cheek against Charlie. He could feel Foster's semi-hard cock against his face and he nuzzled it. Charlie spoke quietly.

"Thank you, Sir. I would very much like to be yours."

"I see you enjoy blacking, and I don't want to deny you that pleasure. You may keep your business, and any earnings you make from it. But you will become my personal assistant. You will move in with me and travel with me. I will not have many tasks for you. You will service my shoes and boots, and you will service me. Beyond that, your time and your life will be yours. Your needs will be taken care of in every way. You will be provided a generous stipend, of which you may spend or save as you choose. Is this a satisfactory arrangement for you?"

Charlie blushed hard, and his whole body was warm and tingling, his face as red as an apple. The last thing he expected to ever hear was something like this. He looked down, his voice wavering.

"Yes, Sir. I would very much like to be in service to you."

"Good. When you are done today, meet me in room 1138 upstairs. Bring your kit. I have several other pairs up in my office that require your skills."

Foster unlocked the door and walked out, leaving Charlie in a daze, imagining what might lie in store for him. The plug kept Foster's cum in his ass, where he wanted it to be. He would keep it there until the next time Foster could fill it for him.

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The day dragged on insufferably long. For both Foster and Charlie. Charlie usually had three "rush hour" periods: morning, lunchtime, and around the end of business hours. The morning slot, as people were arriving for work, generated most of the clientele. A quick touch up was what most sought around lunch or when departing for the day, usually because there was a lunch meeting or happy hour to attend. Some clients dropped off their shoes and boots, and if they lived in the building Charlie would deliver to some of them.

Although he had waves of customers throughout the day, it still seemed to drag on. He couldn't wait to finish up, so he could head up to meet Foster. He was excited and yet nervous, unsure exactly what his new life would involve. He loved the way Foster had taken control. While he issued orders, it was almost as if he didn't need to. Charlie willingly desired to please him. There was a magnetism. Perhaps too early to be called "love at first sight", but he had never felt this way before.

He was also concerned. He was more than what Foster saw, much more. And different. He was not just a "shoeshine boy". Nor was he just a boy. Not all the time. When Foster said he looked like a girl, Charlie had reason to worry. He worked hard to present himself as a boy. She may have initially been raised as Charlotte, but she was only Charlotte sometimes. At work, and much of the time, he was Charlie. Sometimes he was somewhere in between. Bootblacking reinforced the "Charlie" in him, an identity and gender that felt right. Not that the others didn't. He was ultimately gender "fluid", and his identity would morph to match situations, moods, company. Hence the dresses, and other things, for those times when she was Charlotte.

When he was with Foster, he very much felt the older gentleman/younger man bond. He was worried that Foster would not understand the duality of Charlie's gender, that he would be upset, and not want him anymore. Or maybe Foster was only attracted to men, and wouldn't want to be with someone missing male anatomy. If Foster wanted Charlie all the time, he could be Charlie for him. Most of all, he just wanted to please and serve, and to be used.

He wasn't sure how he should dress, or prepare himself to meet Foster. Should she go up there as Charlotte, just to get the truth out there in the open? That way, she'd know right away whether this relationship with Foster would work. No, he thought. I'm a bootblack, and he wants me to work his other shoes, so that's how I'll go. I'll have to explain later. Or maybe I don't have to explain at all....

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Foster's day progressed no faster. He did not yet have an administrative assistant, so the more mundane tasks were his. Most of his meetings were held via video conference. He had established a secure dedicated satellite link for all of his communications, including internet and cell phone. He was pretty much "off the grid", which made it possible to work on certain projects for certain clients. He could offer them direct links to him and his resources, without the possibility of being hacked. He could direct remote operations, both with human and unmanned assets, whether for surveillance or more direct intervention missions. Counterespionage, target neutralization, there was little he couldn't do from his office. For those other meetings and missions that required his personal presence, he had private aircraft, ships, and other global methods of transportation at his disposal.

He was also able to do research on Charlie. For all his access and talent, he was surprised to find little on the boy. No mention of his business registered anywhere, just a few emails some businessmen and attorney's had sent back and forth, looking for recommendations for shoe shining. Facial recognition software matched him to someone named "Charlotte Stewart", in some Child Protective Services records, but he knew sometimes those databases were inaccurate. His gut, which he trusted a lot, didn't get a bad or uneasy feeling from Charlie. Quite the opposite; he felt a strong bond with him, and certainly an attraction for him.

Foster remembered watching him work. He kept quiet while working and didn't discuss other customers, despite his clients discussing what was obviously confidential information, which meant to Foster that Charlie knew how to keep his mouth shut. And with Foster's line of work, that was critical. It meant that he would hopefully not have to take certain steps around him to protect his business and clients. Still, there was something about Charlie that Foster couldn't put his finger on. Like there was something in his past he was covering up. It was more of a mystery, rather than feeling like a warning. Well, he would find out for sure when Charlie came up later.

Which reminded him, he had to cancel a date scheduled for later in the afternoon. There was a Marine, a Warrant Officer and an aide to a certain high ranking Pentagon official who was in town for a meeting at the U.N. She liked Foster to do certain things to her, things that her girlfriend either wouldn't or couldn't do. It involved hypnosis, which Foster had learned from a foreign asset. It helped, because Foster could induce hypnosis after he did a scene with her and manipulate her mind into believing she hadn't done some of the things they did, some of which certainly would have caused her to fail a polygraph if certain questions about sexual "deviancy" were asked.

A few hours later and the doorbell rang. Foster saw from the surveillance camera he had placed and the thumbprint scanner which was disguised as a doorbell button that it was Charlie. He buzzed him into the outer office waiting area. It was a fairly simple and plain office. Basic furniture, a few non-descript framed images. Charlie was dressed in clothes similar to what he had worn earlier, and carried a simple wooden case. Foster spoke over the intercom.

"Welcome Charlie. Proceed through the door on the right."

Foster pushed a button on his smartphone, an app he had custom designed to control all of the security apparatus in his office, and a door on the right opened. Charlie walked through the door into a longer, narrow hallway. The door closed behind him, and Foster's voice spoke.

"Walk down the hall."

A little nervous, Charlie followed the instructions. What he didn't realize was that he was passing through scanners that could reveal not only what was under his clothing and inside the box, but could also take air samples to reveal what chemical elements were in the ingredients in his supplies. Foster poured through the data that appeared on his terminal. The chemical scan revealed only components to make polishes and waterproofing. There were no weapons. But it was what was under Charlie's garments that peaked Foster's interest. And likely answered the nagging questions he had.

A bra. Pert little breasts, constrained and flattened inside. And a bare, shaved pussy, with no sign of a penis. The butt plug Charlie had inserted earlier was still in place.

So Charlie was transgendered. So much made sense now. Why Charlotte appeared instead of Charlie on the background search.

"Wait there a moment, Charlie, I'll be right with you" said Foster.

Charlie stopped, the nerves building in him. What was going on? Had Foster changed his mind? Had he found out she was Charlotte? Was he in danger?

Foster quickly punched the info into a search engine and confirmed that Charlie was indeed Charlotte Stewart. The story Charlie told checked out. She was placed into foster care at age 10 when both parents were arrested for a number of charges, including multiple types of fraud, drug trafficking, endangering a minor, the list went on. Charlotte was bounced around multiple foster families, and then just disappeared one day, when she turned 12. She essentially disappeared.

Foster figured she went underground, changed her identity, and must have been pretty intelligent and resourceful to not only stay off the grid for 6 years but to create and operate a business without attracting attention. He had a few questions for her, but overall, Foster thought she'd be a perfect fit for his needs. Someone to service his physical desires, to handle some of his personal chores. And perhaps, if she demonstrated the right potential, some professional tasks. She was reminding Foster of Natalie Portman's character Mathilda in the movie "The Professional." Of legal age, of course. But she had that independent, driven spirit to have made something of herself.

Foster spoke over the intercom again.

"Come in, boy."

He remotely opened the door to the lounge area where he kept a second office, when he wanted to relax but still have access to work. There was a large brown leather sofa that doubled for a bed when he needed a nap. Another desk with a laptop on it. A large TV, refrigerator, microwave oven, sink, and a door that led to a full bathroom. Should Foster need to spend the night, or a few days, he could do so comfortably.

He moved from the desk to recline on the sofa. He had changed shoes to a pair of boots. Black 6 inch tactical boots that had sustained a few scuffs. Enough to provide Charlie some work, and a chance for Foster to observe him.

Without saying a word, Charlie went straight to Foster and knelt before him, opening his wooden box. He removed his supplies and set them out in an orderly fashion on a cloth, to protect the lush oriental carpet that covered the hardwood floor. He began, as before, soaping the boots clean. Foster began asking a series of casual questions.

"So, Charlie, the terms of my offer are still acceptable?"

"Yes Sir," Charlie replied quietly. "Very much so."

"Do you have any questions for me?"

"Not really," he said, focusing on his work.

"Not really? That implies you DO have questions."

Foster pressed his boot into Charlie's thigh to emphasize the word 'do'. Charlie tried to stifle a gasp. The pressure of the boot on his thigh made him feel warm, and surprisingly aroused.

"DO you have questions, boy?" Foster asked again, looking intently at Charlie and his reaction, as he again pressed down in emphasis. Charlie's eyes fluttered and he gripped onto the boot to avoid swooning.

"N-n-no...I mean...yes, Sir. I-I have a few."

"Good. Because I have a few of my own as well."

Charlie mustered strength to control himself, took a deep breath, and finished wiping the soap off. He reached for the polish and began applying it.

Foster decided to put a little pressure on the boy, to see how he handled it.

"I do not take kindly to lies or deception. In fact, they are the worst sin you can commit in my eyes. And there are repercussions for doing so. So I will ask you one more time: what questions do you have?"

Charlie focused intently on his work and spoke, not looking up.

"What...umm...how...how will I be servicing you, Sir?"

"In whatever way I choose, whenever I choose. I will ensure you will not be injured. I have some rather...unconventional preferences, sexually and otherwise. You will learn them in due time. Have you heard of BDSM, boy?"

"Yes...yes, I have, Sir."

"So you are familiar with the wide range of activities and fetishes that exist?"

"Yes, Sir..."

"Good. If you are in service to me, then you are submitting to me. You will obey my orders without question. We will have protocols, instructions you are to follow without me having to tell you each time. For example, when you greet me behind closed doors, you are to be kneeling as you do now. I will stand in front of you and you will rest your face on my cock, as a reminder of your place."

"While initially I will give you a safeword, if you are to remain in my service eventually that safeword will disappear. It will do so after you have experienced each of the fetishes or examples of service I have for you."

"I may eventually have other tasks for you, tasks not related to your submission or your bootblacking. You might assist me with activities related to my business. That is, if your service in all other areas proves satisfactory. Does that answer your question?"

"Yes, Sir," Charlie quietly responded. His eyes, although focused on his work, went wide at the mention of BDSM. It was the one area he felt made sense to him. He felt like it was his place to serve and submit, and BDSM provided a framework for it. He had craved being controlled and of experiencing challenging situations, and when he first learned of BDSM several years ago, he felt like he found the solution to healing from the emotional and sometimes physical trauma he had experienced growing up. He had experimented with a few partners, other boys and girls, but hadn't found anyone who could provide even a fraction of what he sought. Now, Foster was offering a chance to experience at least some of what he craved, of what he needed. There were still a great many unknowns, but Charlie's gut told him that Foster was the right place to start.

"What other questions do you have?"

"What...what if you don't like me? What happens then?"

"Well, I prefer to think of it as if we were not a good match for each other. I would end our arrangement. However, I would provide you with enough resources that you would not have to worry about work or a place to live for a long time."

"Oh. Okay, Sir."

Charlie finished applying the polish and began buffing the boots with a soft brush. Foster decided to up the pressure, and to test Charlie, mentally and physically.

"Now, I have a few questions of my own. As I discussed, honesty and integrity are of upmost importance to me. My life, my work depends on it. So I am going to ask you a series of questions, and put you to a series of tests. If I am satisfied with your responses, consider our arrangement formalized, legally and otherwise. I am as good as my word. I have a security system installed here that is programmed to call 911 and trigger a rapid response if anyone yells the word "help". If the word 'red' is said three times in a row, a red light on the ceiling will turn on and start recording what is occurring in here for the police to use if necessary. Now, I want you to trigger the recording, so you can see that I am telling the truth. Say 'red' three times."

Charlie said, "Red, red, red."

A red light on the ceiling illuminated.

"Just as I said," said Foster. "Do you believe me, with everything I've said?"

"Yes, Sir."

"Good, now, what is your name?"

Charlie tried to act normal, when inside the questions he was dreading seemed to be coming his way.

"Charlie, Sir."

Foster sat up and slapped Charlie across the face. Not hard, but enough to catch Charlie off guard. He was surprised, a little turned on by the impact that stung his cheek, but also started to become a little concerned.

"Bullshit!" said Foster. "Your name, the one you were born with."

"It's...it's Charlie, Sir! Charlie Stewart!"

Foster slapped Charlie again, twice this time and a little harder. He lifted his boot and placed it against Charlie's chest, pushing him to the floor. He followed Charlie down, mashing his boot against Charlie's stomach, then ground it against his crotch before dropping to a knee next to Charlie's side, with the other knee across Charlie's pelvis, pinning him down. His hands went to the front of Charlie's button down shirt and tore it open, the buttons breaking loose, exposing a simple white bra. He closed one hand around Charlie's neck, squeezing lightly, just enough to hold him in place. His other hand went to the front of the bra and pulled it up, exposing small, barely handful sized breasts capped with pink nipples.

"Your...REAL...Name."

Foster's hand struck his cheeks on each word, for emphasis.

"Sir...I..." Charlie blabbered.

Foster reached down and gripped a tit, then firmly pinched and slightly twisted a nipple.

"Charlotte!" she squealed, "Charlotte Stewart, Sir!"

In an instant, she transformed from Charlie to Charlotte. Foster had been able to do that to her, to direct her sense of herself.

"Why did you lie to me, Charlotte?" Foster said, looking directly and intensely into her eyes. She found she could not tear herself away from them.

"I didn't, Sir...I...I...unnhhnnnn!!!"

Foster slapped the other tit, then squeezed it cruelly at the same moment he tightly gripped her throat.

"Explain yourself, young lady!"

Foster then released her tit and neck. He tore the cap from her head, releasing Charlotte's long thick red hair. She gasped and then groaned as he grabbed her by the hair and stood up, pulling Charlotte to her knees. He sat back down on the sofa, pulling her over to him, making her knee walk over. He still towered over her as he sat there, legs spread, Charlotte kneeling in between them. He yanked on her hair, pulling her head back so she had to face him. Charlotte's story came tumbling out.

"I'm both, Sir! I'm Charlotte and...and Charlie! It's...it's complicated...."

Charlotte's eyes began watering.

"I've always been this way. A boy and a girl. I mean, I'm a girl, but sometimes I feel like a boy. My parents didn't understand. They hated it when I wanted to be a boy. They said I was confused, and they punished me. They locked me in my room, sometimes for days, until I apologized. So I had to hide him, hide Charlie. And when they went to jail, I had to go live with other families. They didn't understand either. One of them, a preacher and his wife, tried to do an exorcism on me, saying I was possessed by the devil. That's when I ran away."

A tear rolled down Charlotte's face, as she continued to tell her story, her voice wavering and a little higher in pitch. Foster's grip relaxed, and he began stroking her hair.

"When I got away from them, I was finally free. I could be Charlie when I wanted. I used to hide out in the library. I found storage rooms and little places I could hide when the library was closed, so that's where I stayed. I learned how not to get caught. I got to read lots of books, and learned about how some people have different genders, both male and female. And that seemed like me. I'm not always Charlie. Sometimes I'm Charlotte. And sometimes I'm somewhere in between. It's hard to explain. Most people don't understand, so I keep to myself."