The BootBlack

This story was inspired and requested by a gender-fluid friend, who happens to be a talented bootblack. The bootblack character is based in great deal upon her/him, and her/his requests for what would be in a story. Certain specific language used ("cunt", sissy, faggot, for example), is by her/his request, to more closely mirror how s/he likes to be treated. No disrespect is meant by the use of such terms. Both my friend and I are also bisexual and while we recognize that some might be offended by some of the more derogatory terms, we embrace their use in certain contexts by those who are fellow members of the LGTBQ community. Please be open-minded when reading this story. Gender is explored and interchanged between one of the characters in particular, and the way it is written is intentional. Some may find this confusing. Also, all characters are age 18 or above.

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Charlie was one of the finest bootblacks in the city. At 18, Charlie excelled in the art of bootblacking. He had been practicing for about 5 years, but had already amassed incredible skill and a regular group of clients: successful attorneys and entrepreneurs who viewed the hand care of their footwear as a barometer of affluence, to afford to have a "like new" pair of shoes or boots every day for work. Charlie viewed his craft as a calling. In this day and age of disposability, of consumerism, his was a lost art. He worked hard to become proficient and master the skill, much harder than anyone realized. His trade was traditionally male, almost exclusively a "boy's club."

Like barbers and tailors, the masters of bootblacking were virtually all old enough to collect social security. Charlie was truly unique in this inner, elite circle, being so young and so...different. The "elders" had mixed feelings about him. Theirs was a dying art, and there were few who were young enough to keep it alive. They welcomed him for his passion, his dedication, and for taking it so seriously. Charlie adhered to the traditions and was strictly "old school", in that he modeled his technique as such. No electric buffers, new lacquers, or synthetic fibers. In fact, he even mixed and created his own polishes. However, his talent meant competition, and Charlie certainly gave the elders a run for their money, no pun intended.

As such, Charlie was polite and respectful to them, and vica versa, but generally kept to himself. His workspace was not in the most ideal location for "foot traffic", but his reputation ensured his customers were regulars, and would take a slightly longer route to the office in order to benefit from his service. His space was located inside one of the larger, older office buildings in downtown Brooklyn. Most of the tenants were attorneys, but there were a few entrepreneurs who occupied spaces that were vacated by firms who moved into the new, state of the art skyscraper next door.

He literally took on the persona of a 19th century bootblack. Pristine brown leather lace up boots. Black wool trousers, held up by suspenders. A white button-down, long sleeved shirt, buttoned almost to the top. His skills meant that the white shirt generally remained spotless, not an easy feat. A driving cap hid his long ginger hair. For a boy, he was both beautiful and handsome. Short and slender in build. Piercing blue eyes and fair skinned, which would turn red when he blushed, which came frequently, especially when complimentary comments were bestowed on him or his work. He had somewhat of an androgynous quality to him, which lent itself to his mysteriousness. Both men and women, especially straight men and women, were drawn to him, for reasons they couldn't explain.

Foster ran a consulting firm in the building in which Charlie worked. He sought out the space for a number of reasons. The rent was cheap, he had few neighbors on his floor, and he could remain fairly anonymous. His clients were primarily governments who sought discretion for covert activities that bordered on questionable legality. From the hallway, his office appeared to be just another private law practice, handling contracts, wills and estates. That cover worked well.

Foster had done well for himself. A 22 year career in the military in Special Operations gave him the contacts he needed to jumpstart his business, both domestically and internationally. While his tours of duty took him around the world, since being injured on a covert mission he finished his time out as a "behind the scenes" guy. He knew how to get certain things done. He had a knack for innovation and thinking "outside the box". He had made connections the world over, so it made facilitating the sensitive needs of his clients easy. It also made him extremely wealthy, in part because of how he managed his affairs. He did not live ostentatiously. While he dressed and lived well, he did not wear his wealth on his sleeve, and overtly advertise his economic status.

While he didn't have the physique he once had at the height of his deployments, he did his best with his disability to be relatively in decent shape. At six feet, with dark hair and blue-grey eyes, he wasn't a giant but his quiet strength made him tower over others. With his career and current job, a family was impractical, so he had a few "friends with benefits". He didn't choose his partners by their plumbing, so he would sleep with women...men...with whomever there seemed to be a mutual attraction.

Foster discovered Charlie by accident. As was his way, Foster had done a recon on the building prior to signing the lease. He made sure he knew all of the access and egress points, storage rooms, utility controls, stairwells, and roof access. He learned a long time ago it's important to know not only how to get in, but how to get out of a place, and to have multiple backup options. During his survey, he found Charlie at his spot, doing what he does best. There were several gentlemen waiting in line for their turn, a sign that whatever the bootblack was doing, it was worth the wait.

He was immediately taken by Charlie. He could have sworn by his quick, professional technique and attention to detail that Charlie had done time in the service, but he appeared far too young. There was something else about the boy that Foster was drawn to. It wasn't just that Charlie was attractive. There was something about his energy he couldn't quite put his finger on. It was enough that he stopped to watch for a short while. He asked one of the men waiting about Charlie.

"Yeah, he's the best," said an older one. "In all my years, I've never had my shoes done so well. And he's not bad on the eyes either. Very pretty, for a little fella. Hell, if I was gay, I'd marry him!"

His last comment drew chuckles from the other men assembled, and the blush that was Charlie's cheeks became bright red, as he tried to ignore the comments and focus on his task at hand.

Foster eventually continued on his way, but his mind over the next several weeks kept coming back to Charlie. He finally decided to get his shoes shined. He stopped by Charlie's stand, just as his last customer was getting up. He took his place and sat down on a padded chair. Charlie took his place at Foster's feet, kneeling down in front of him.

"Good morning, Sir," Charlie said in a quiet voice.

"Good morning. I'm guessing your name's Charlie?" Foster asked, gesturing to the sign on the stand behind him that said "Boot Black Charlie"

"That's right, Sir," Charlie replied, as he began lathering Foster's shoes with a soapy paste, lathered on a brush.

"You're quite young. How long have you been a bootblack?"

"I started when I was ten. But I've been professional for five."

"Wow. You ARE young. Shouldn't you be in school?" Foster asked.

"I prefer to be here, Sir."

Charlie wiped the foam from Foster's shoes with a clean white cloth. They already looked better.

"Don't your parents, or the school know?"

"I don't have any parents anymore. They're both in jail and I don't like my foster family. So I'm on my own."

He placed one of Foster's feet on his thigh and began applying black polish from a silver tin, applying small amounts in circles with his fingertips. He held Foster's calf to steady his leg with a gentle grip in his other small hand. His hand felt soft, but it was almost as if a small amount of electricity was flowing between them.

"Are you old enough to be on your own?"

Charlie blushed. "I think so"

"So where do you stay?"

Satisfied with work on Foster's right foot, he switched and placed his left foot on his other thigh, this time a little higher up and towards his crotch. He began polishing Foster's other shoe.

"I have a small room behind that wall," he gestured behind Foster, eyes quickly glancing at Foster, then darting away.

Foster could have sworn he felt Charlie start to massage his left calf. He said nothing, hoping Charlie would continue. Charlie lifted Foster's leg, so he could inspect his shoe more closely. He could have sworn he saw Charlie glancing at his crotch several times. He was definitely working his fingers over Foster's calf, stroking ever so gently. Foster was tingling, and he felt himself growing hard. He tried shifting in his chair, but Charlie held onto his leg, and he knew that only served to pull his trousers tighter against his crotch, a fact not unnoticed by Charlie.

Charlie placed Foster's foot down on the floor and turned around, still on his knees. He reached over to take another tin of polish down from a shelf next to them. In doing so, he was on his hands and knees, his dark trousers pulled tight against his ass, outlining it and the crevice between. Foster could not avoid looking, nor did he want to. Lustful feelings arose in him. This boy had curves and hips like a girl. Despite being young enough to be his son, Foster desired Charlie.

Charlie turned back, catching Foster staring and blushed. He shuffled closer to Foster, placing his foot even higher up on his thigh, practically pressing into his crotch, which also caused Foster's legs and thighs to spread apart a little. He began applying the next layer of polish, a sealant which would keep moisture out and the color in. The scent wafted up into Foster's nose and was intoxicating.

Charlie was also aroused, his face flushed. He had always had an attraction for older men, balancing his desire for women closer to his age. He sensed that Foster felt something for him, that he wasn't just another heterosexual male. Maybe Foster wanted more than just his services as a bootblack. Rarely did Charlie pursue anything with a customer. One time he had, and regretted it. He thought the gentleman would be okay with it. At first, he seemed to enjoy how Charlie serviced him, taking him deep into his mouth. But then he abruptly stopped him, almost in a panic and fled. Charlie never saw him again. He lost a regular customer that day.

But Foster was different. As Charlie took a brush to his shoes, he could feel Foster's eyes burning into him. He tried to concentrate on buffing the shoes, but he fumbled and dropped the brush. He picked it up and realized that he had placed his hand on Foster's knee to steady himself. Looking up, Foster's eyes locked with his and Charlie was paralyzed for a moment. He managed to break his gaze away, and as his eyes traveled down to focus on his shoes, he saw the clear outline of Foster's hard cock in his pants. He tried to stifle a gasp and quickly returned to his work, buffing the other shoe while his own epicenter of pleasure between his legs throbbed.

Finished with the brush, he got up on his knees and tried to reach across Foster to grab another folded towel from a rack behind to the chair. He lost his balance and fell forward. He unsuccessfully tried to brace his fall with a hand on Foster's upper leg. The rest of him landed between Foster's thighs, his face coming to rest in his crotch. He felt the hard shaft against his cheek and forehead, separated only by a few thin layers of cloth.

They were only in that position for microseconds, but felt like an eternity. Foster felt Charlie's soft face and warm breath on him and he groaned. Charlie could feel Foster throb. He tried to pull back, but Foster's hand had gone to the back of his head and held him firmly and commandingly in place. His other hand pinned Charlie's hand against his leg, gripping his wrist tightly. Charlie moaned, the feeling of not being in control awakened the nymph in him. They remained like that for several moments, both breathing heavy. Foster was the first to speak.

"Take me to your little room, boy."

He released the hold on Charlie, who slowly rose to his feet, as did Foster. He looked up, Foster towering over him by a good foot. The look in Foster's eyes was all business. Charlie knew what he wanted, and he was going to provide it, willingly.

He took Foster by the hand, his somewhat dwarfed in Foster's, and led him back behind the sign. He opened a small door in wall and led Foster inside. The room was small, dimly lit. Foster could just barely make out a small bed and dresser. A clothes rack held a selection of button down shirts and trousers, all neatly pressed. He couldn't quite see, but he thought he also saw a number of...dresses?

Charlie closed the door and locked it. He turned to look up at Foster, just able to see the outline of his face as he took Foster's hands in his tiny ones. They stood there for a moment. Without a word, Charlie lowered himself down to his knees, releasing Foster's hands so he could unbuckle his belt and lower the zipper on his trousers. He slid Foster's pants down to his ankles. Reaching into the waistband of his boxers, Charlie slid them down as well, releasing Foster's cock. He slid his hands up his thighs, causing Foster to tremble.

They finally came to rest on his cock, which jumped slightly at the touch. Charlie wrapped both hands around it, gently squeezing it once, feeling the heat and strength, then with a light touch stroking it. Foster moaned, marveling at how soft the boy's hands were, as if they belonged to a young woman. He lowered his mouth, extending his tongue and licking the tip of his cock. He swirled his tongue around the cap before engulfing it in his mouth. He slid his mouth down as far as he could, the end pressing against the back of his throat. Withdrawing with a slight amount of suction, he then plunged down again, this time trying to take it deeper while fighting his gag reflex.

Foster's eyes had rolled back in his head, shivering at the sensations Charlie was creating. Not only was he a skilled bootblack, he was phenomenal at sucking cock. Charlie began stroking Foster as he sucked, creating a long tunnel to mimic another tight, warm part of Charlie's anatomy. Again, Foster's hands went to Charlie's head, gripping it through the driving cap, guiding Charlie's actions. Charlie gurgled, enjoying the feeling of being used as he was facefucked.

Occasionally, Foster would stop and hold Charlie in place, deep in his mouth, pressing further, trying to enter his throat. Charlie would gag, squirming, but did not try to pull away. He'd then resume thrusting in and out of Charlie's mouth. Charlie's right hand slid down lower, between Foster's legs. His thumb massaged the spot between his balls and his ass. Foster gritted his teeth and groaned loudly, his cock throbbing harder. How did Charlie know how sensitive he was in that area?

"Fuck, you're a naughty boy, aren't you? Goddamn, that feels good!"

The intensity grew, and Charlie rightly knew Foster was close to cumming. He slowed his efforts, not wanting him to cum...not quite yet...and not quite there.

"Dammit, I was this close!" said Foster, panting.

He felt the hand between his legs leave him and heard Charlie fumbling around, then reaching into a box that was on the table next to his bed. His mouth left Foster's cock but Charlie kept his hand on it. He moved onto his hand and knees on the bed, turning away from Foster, hand still gripping his cock. Foster could see that Charlie had pulled down his trousers and pulled up his shirt. Just enough that he was exposed and naked from his lower back to just below his ass. Just enough to reveal his tiny pink hole, glistening with lubricant, masking anything else from view.

The curves Foster noticed when Charlie bent down earlier, when he was blacking his shoes, were even more pronounced now and perfectly framed by his trousers and shirt. Foster had never seen an ass more perfect. If he didn't know better, he would have thought it belonged to a girl, which only lent to Charlie's androgynous beauty for a boy. And to the lust Foster felt for him.

Charlie directed the head of Foster's cock to his asshole and held it there a moment before pressing back against it. The tiny hole relaxed and the head slipped in. Charlie gasped and paused a moment. Foster's hands went to his narrow waist, just above where his hips flared out to the side. Charlie relinquished control and released Foster's cock, placing both hands on the bed, ready for what would come next. Foster pulled Charlie back, and slowly his cock slid inside Charlie's tight ass. Charlie whined, dropping his head down. Foster groaned, marveling at how easily he entered the boy. He looked down, and in the dim light his lust grew. While Foster was of average size, compared to Charlie's small frame, his cock made Charlie's ass looked tiny. Foster bottomed out in the boy.

"Oh fuck!" Charlie gasped. "Please fuck me, Sir."

"Yessssss" Foster growled.

He gripped Charlie hard and held him in place. He started slowly fucking Charlie's ass, like it was a pussy. It had been a long time since Foster felt anything this good. He was going to enjoy using him.

Charlie's breathing deepened in time with Foster's thrusts. He began sighing, the pitch of his voice increasing. Foster's more aggressive nature came out.

"You like getting fucked in the ass, don't you boy?"

"Yes...Sir..." Charlie panted.

"You've got a pretty little ass, for a boy. You look just like a girl, bent over like this."

"I...I do...Sir?" Charlie managed to squeak out.

Foster noticed a tinge of what might have been panic. But that did not deter him from owning this boy's ass. Instead of holding Charlie still, he started pulling him back and forth onto his cock.

"Yes. And I'm going to treat your sissy ass like a cunt"

"Oh...Sir...yes...please!" Charlie cried.

Charlie started to fuck Foster back, which only helped to turn both of them on even more. His little ass cheeks quivered as Foster's pelvis mashed up against them each time he bottomed out in the boy. He wasn't going to last long at this rate.

"Oh...god...Sir...I'm gonna....." Charlie panted.

"Going to what, boy?" Foster yelled.

"C-c-cum...Sir...oh god...cumming Sir!!" Charlie wailed

Charlie's body bucked, Foster gripped on tighter, so close himself. He rammed Charlie back against him several more times, then exploded with a roar. Charlie could feel the ropes of Foster's cum squirt against the walls of his bowels and he shuddered, his orgasm extended. Foster held Charlie tight against him for awhile, occasionally drawing back and pulling Charlie hard and tight against him again.

They both struggled to catch their breath and stayed in that position for awhile. Eventually, Charlie felt Foster start to soften and shrink. He reached over and grabbed what Foster recognized as a small silver butt plug from a drawer in a nightstand next to the bed. He slowly pulled off of Foster and quickly turned around to face him, his hand reaching behind him for a moment to insert the plug. He took a washcloth, applied some sort of lotion from the drawer and cleaned Foster off. It felt slightly cool on his cock, but not uncomfortable.

When Charlie was done, he leaned forward and sucked Foster into his mouth once more, bobbing his head up and down a few more times before reluctantly pulling his mouth off of it. He kneeled down before Foster and slid his boxers and trousers back up, zipping up the pants and fixing his belt. Foster stroked the side of Charlie's face as he worked. When he was done, he looked up into Foster's eyes, who was staring down at him fondly. He slapped Charlie's face several times, then caressed the cheek with his hand. The energy between them filled the room, and all seemed right in the world, for the first time in a long time for both.