The BootBlack

Foster was pleased with the response he was getting, and felt like his intuitions about the young one in front of him were correct. He pushed further.

"Don't you have a boyfriend? Or is it you have a girlfriend?"

"Not now," Charlotte replied. "I mean, I've had boyfriends and girlfriends before. But they usually break up with me when they find out about Charlie...or Charlotte. The only one I had that liked me, all of me, she moved. She was born a boy but wanted to be a girl. Her parents, when they found out about us, they moved to another state and put Sienna into a institution. I tried to find out where, so I could go rescue her. But I couldn't find her."

"So you have no one now?"

"No, Sir."

Another tear rolled down her face and she looked away. Foster slid his thumb across the cheek he had turned red with his palm and wiped it away, gently caressing her face.

"Is there anything else you have to tell me, young lady?"

"No...Sir...it's just...I mean...I'm sorry...I didn't mean to screw up...it's just...I thought you'd only want me if I was Charlie...only Charlie...."

Foster smiled. She...he...was the one.

"You'll find that I too, have a gender that is somewhat...fluid. The man you see, or think you see, does have other tendencies. They don't come out often, but in the right circumstance, with the right person, they do.

"You are...they do?" Charlotte asked, looking up at him.

But let's talk about your concern. Charlotte...Charlie...the offer still stands."

"It does?"

"Yes, it does. However, I cannot let the fact that you were not initially forthcoming with me go unaddressed. There are punishments and consequences that must be meted out."

"Yes...Sir..." Charlotte looked down, ashamed but accepting.

Foster stood up, gripping her hair once again, pulling her up against the sofa and bending her over it. He decided to play out the punishment against both of them, Charlotte and Charlie.

"Are you willing to accept what's coming to you, young man?

Charlie took over from Charlotte.

"Yes, Sir."

Foster placed his hand on Charlie's back, between his shoulder blades, holding him down. His other hand reached under Charlie and unbuckled his belt, unbuttoned and unzipped his trousers, then pulled them down to his knees. Charlie had a lace thong on that accentuated his curves. The butt plug remained in place. He took Charlie's belt off, grabbed his wrists and brought them behind his back. Holding them together, he looped the belt around them and cinched them tight.

"Well, look at this," said Foster. "You're quite the sissy, aren't you?"

"Yes Sir," Charlie meekly replied.

"A boy who wants to be a girl. A faggoty little girl."

Foster spanked him, making Charlie jump. Not just from the stinging impact, but because part of Foster's hand made contact with the butt plug, pressing it into him. Foster did that intentionally.

"Yes, Sir."

Whack.

"Say it, boy. 'I'm a sissy'."

Another handprint marked Charlie's ass.

"Uhhnnn...I'm a sissy, Sir!" Charlie whined.

"'I like cocks in my ass.' Say it!"

"I...like...OOOOH...YOUR cock in my ass, Sir!"

Foster smiled, remembering how good it felt to sodomize the young man. He landed a few more blows, massaging his cheeks after each one, before peeling the thong down. Foster could smell Charlotte's scent and see her moisture in the crotch of the thong. He grasped the butt plug and played with it.

"Why do you have this plug in your ass, boy?"

"To [whack]...remind me [whack] ... of you [whack] ... Sir [whack] ...to keep your cum inside, Sir."

Foster released his hand from Charlie's back and with both hands spread his reddened, warmed ass cheeks, pulling them apart and up, revealing Charlotte's bare and wet pussy, the lips just barely parting.

"And what do we have here? A cunt!"

Foster left one hand spreading Charlotte's cheeks and with the other spread apart her lips, revealing a small wet pink hole and further up, a hard nub of a clit. He played Charlie back into Charlotte.

"A cunt. And why is it so wet, young lady?"

"Be-because...you make me wet, Sir!"

Foster fingered her cunt, sliding one, then two fingers inside to stroke her G-spot, then up to rub her clit, and alternated back and forth, causing moans and gasps as Charlotte writhed bent over the sofa.

"And do you know what happens to wet cunts?"

"Wh-what, Sir?" she panted.

"They get hard cocks inside them, filling them with cum."

He pulled his fingers abruptly out of Charlotte, causing a protesting whine. He yanked her up by her hair so she was leaning on her palms, causing her ass to jut out. He reached around and forced his soaking wet fingers into her mouth. Charlotte willingly took them in, moaning as she sucked on them, tonguing her juices off of his fingers.

"You like the taste of pussy, don't you, cunt?"

Charlotte moaned around his fingers. He withdrew them to slap her face, leaving traces of her secretions on her cheek.

"I couldn't understand you!"

"God...yes Sir...I do," she moaned.

"Excellent," said Foster. "I'll be able to put that to use later."

He pushed her back onto the floor and sat back onto the sofa, his boots extended in front of him.

"Now, seeing as how you love boots, I am going to watch you polish mine. With your cunt. Rub your cunt on my boots!"

Charlotte struggled to get to her knees, wrists still bound behind her back. She shuffled over to his feet, looking at his boots, trying to figure out how to accomplish the task. She spread her knees wider and hobbled forward, straddling one boot. She then spread her knees wider so she lowered down, until her pussy made contact with the toe that she had just recently finished polishing.

"Rub." Foster ordered.

Charlotte began rotating her hips, keeping her cunt in contact with the toe. She sighed and moaned, the cool leather massaging her lips and clit. Her juices lubricated it well, and she thrust herself on it, riding it, masturbating herself on his boot. She was surprised at how much it turned her on, and little mewing sounds emanated from her. She looked up at Foster and he was wide eyed, obviously turned on by her actions. She closed her eyes and continued to ride, trying hard to keep her balance as her hands and arms were restrained.

"Enough," Foster barked, breaking her concentration. "Switch!"

Reluctantly, she stopped, raised herself up and shuffled off of it over onto the other boot. She lowered herself down and continued riding, getting wetter. Foster shifted his foot around, increasing the pressure and sensation on her cunt. She gasped and moaned, feeling herself get wetter, her clit harder. It was humiliating, but that served to arouse her even more. She wanted to cum this way and focused on it. To her disappointment, Foster stopped her.

"Very good. But you are not permitted to cum yet, young lady. Clean up my boots."

Charlotte once again pulled off of him and sat back on her heels, arms and wrists still useless. She tried to figure out how she was going to accomplish this next challenge.

"Lick them clean, cunt."

Charlotte bent over, shuffling slightly, and began lapping quickly at his boots, just barely dabbing them with her tongue.

"Slower. I want to watch," Foster ordered. He wanted to enjoy the visual.

Charlotte tossed her head to the side, so he could see her face. She leaned back down again and slowly ran her tongue over the curves of the newly polished boots. She made a show of it for him. The taste was of her pussy, which she did not mind, and the scent of polish made for a heady, almost swooning experience. A new one for her, but she decided she liked it. As she did when she blacked them, she made meticulous work of the task in front of her, cleaning every spot she had soaked with her cunt. When she was finished, she sat back on her heels and looked at Foster.

"Are you satisfied with my work, Sir?"

Foster said nothing, but pulled her up onto the sofa by her hair and laid her prone. He marveled at what lay before him. With the men's shirt on, even with the curvy ass and long tresses of red hair, the slender body before him could have belonged to a boy. But the scent and pussy lips peeking from between her legs turned that ass into one of a young woman. Either way, he wanted her...and him.

He released Charlotte's wrists from the bondage of the belt and flipped her over. He pulled the shirt from her body, and ran his eyes up and down the young woman's frame, salivating at her curves. He straddled her hips and cupped her breasts in his hands. His fingers and thumbs expertly manipulated her nipples, gently rubbing/flicking them back and forth with his fingers and thumbs. She sighed and moaned at his efforts.

"Your nipples are sensitive. I like that. Mine are too. And you will service them for me, exactly how I am doing it to you. Treat them like one of your baby dyke girlfriends."

Foster then leaned down and took a breast and nipple into his mouth, his tongue and fingers mirroring each others' efforts, then switched back and forth between each breast. Charlotte's back arched slightly at his efforts. He knew how to stimulate them effectively. He stopped and stood up in front of the sofa, in front of her. She got up onto her knees in front of him. She unbuttoned his shirt and slid it off his shoulders and arms, placing it carefully over the back of the sofa. She then leaned forward and did her best to mimic his efforts on her tits, her mouth and hands and fingers at work. Foster groaned and gripped her by the hair, holding her to him, looking down at her.

"Yessssss....fuck, you're a natural, you little slut. I'll bet you turned on all your little dyke girlfriends, didn't you, whore?"

Charlotte whimpered at his verbal humiliation.

Foster moved her head to his other nipple, which she greedily took in her mouth to pleasure him. She loved how it made her feel, to take care of him, to give him pleasure. She felt the energy in him change somewhat. He was still in charge, but the feminine side of him was a little more apparent.

He abruptly stopped her and pushed her down to sit on her knees. She looked up at him.

"Take off my pants and boots, young lady."

She bent over and reached down to unzip his boots. With her ass upturned, he took the opportunity to take a four foot section of quarter inch bamboo rod from the shelf above the sofa and lay some streaks across her ass. She yelped at each stripe, then unbuckled his belt and unzipped and dropped his pants. He dropped the cane and reached down to grip an ass cheek in each hand, firmly. She gasped and moaned.

He then grabbed her hair and pulled her up to push her down onto her back. He grasped her upper legs and yanked her to the edge of the bed. His cock stood upright and was rock hard. He pushed her legs back until her thighs touched her tits. It also served to completely expose her pussy and butt plug. He held her legs back with one hand and with the other grabbed his cock. He directed the head at her pussy and then began to rub the head up and down, from her clit through the lips to the bottom of it, and the opening into her vagina. She moaned at his efforts. He then slapped her pussy several times with his cock.

"What's this called, nymph?" he demanded.

"M-my...cunt," she replied.

"Yes, your cunt. And what did I say goes in there?"

"Cocks, Sir. And cum. Cocks and cum."

"And what is going in there, right now?"

"Your cock, Sir. In my cunt."

He directed the head to the opening, making circles around it, lubricating it with her juices. He then pressed forward, drawing sighs and moans from her. Her cunt was tight; it had been awhile since anyone (or anything) had filled it. Foster liked a snug fit, and she did not disappoint. He slid into her relatively easy, her slick hot tunnel welcoming his shaft.

"Mmmmmmmm...," she moaned.

"Fuck, that's good. You're so wet, and tight."

He could feel the butt plug through the thin membrane separating her pussy from her ass. He pressed his pelvis up against her, until he bottomed out. He could also just barely sense her cervix, the head brushing up against it. He held her tight against him for a few moments, savoring the pleasure, before beginning a thrusting motion, in and out. She lay there, taking it, letting him use her body.

"Rub your clit, young lady," he ordered.

She reached down with both hands and placed them on the top of her cunt, one hand spreading the lips the other began rubbing her clit. She began moaning and panting as he fucked her. It had been awhile, and she reveled in the sensations. He knew that their efforts would bring her to orgasm soon.

"You are not allowed to cum without permission, understand?"

She nodded fervently as her body was rocked back and forth on the sofa.

"When you are close and ready to cum, you will say the following: "Permission to cum, Sir?" If I am feeling generous and you have performed satisfactorily, I will grant your request. When you start cumming, you will tell me, out loud, over and over, "I'm cumming, Sir."

"Yes...Sir."

"When I take you as Charlie, your ass will become your boy "cunt", so if you are Charlie and I refer to your "cunt," know that I am talking about your asshole. Understand?"

"Sir...yes...Sir..." Charlotte moaned.

He continued fucking Charlotte, leaning over her, his frame outsizing hers. He constantly alternated techniques on her, reaching down and tugging on the butt plug...reaching between them and playing with her tits...occasionally tweaking a nipple to generate a squeak out of her...choking her...slapping her face...gripping her by the hair...all designed to maximize sensations.

"Sir...Sir...permission to cum, please!" Charlotte gasped.

Foster continued his assault on her body.

"Not yet, cunt. I'm not ready for you to."

Charlotte whined and moaned, as Foster increased the severity of his efforts.

"Please, Sir, PLEASE!" Charlotte begged. Foster loved it when his partners begged, when the desperation set in.

"Please, Sir, WHAT, young lady?"

"Oh god, PLEASE! Permission to CUM!!!!" she wailed in desperation. Foster felt her pussy swelling, getting wetter, like a damn ready to break, and the warmth of her glove increased.

"NOW!!!!" Foster growled.

Charlotte exploded.

"CUMMING, SIR!!!!" she cried, as she thrashed about underneath him. Foster's own orgasm was approaching, and he kept pounding away.

"Fuck, YES!" Foster bellowed, and he came, hard, his cum filling her pussy, mixing with her slickness. He thrust over and over as she convulsed under him, both of them breathing heavily. He lowered himself down on top of her, supporting himself on his elbows, and her head and face were against his chest, her arms wrapping around his torso and legs around his hips. She clung to him tightly, refusing to let go. He let his face rest into her red mane, strewn around above her head.

Eventually, he lifted himself up and pulled up off and out of her to sit back on the sofa, next to her. She nestled up against him, both sweating, their breathing starting to return to normal.

"Clean me up, young lady." Foster said.

Charlotte sat up and slid down onto the floor between his legs. She reached for one of the towels from her wooden box, but Foster stopped her.

"No, use your mouth and tongue."

She knelt down between his legs and took his cock into her mouth. She sucked on it, like a pacifier, letting her head slide down until his semi-hard cock bottomed out in the back of her throat. She alternated, sucking on him and then pulling her mouth off so she could run her tongue down the shaft, licking his inner thighs, his balls, anywhere a sign of their juices had intermingled on his skin. She was thorough, and ensured no spot was left untouched, until she was certain she got every glistening drop. She then leaned her head against his thigh, eyes closed, wrapping her hands around his other leg to hold him tightly.

"Are you sure you're done?" Foster asked.

"Yes, Sir," Charlotte replied, "I got every drop," confident and satisfied with her work.

Foster smiled and stroked her head, sharing her sentiment. They lay like that for awhile, Sir and his servant. Charlotte was the first to speak.

"Thank you, Sir," she said quietly.

"For what, Charlotte?"

"For trusting me, Sir. For forgiving me. For not getting rid of me."

Foster smiled.

"You're welcome. But you're not done yet. I am not satisfied that Charlie has learned his lesson."

"Yes, Sir," said Charlie.

"Assume the position when I fingered Charlotte's cunt, boy." Foster ordered.

Charlie knelt again against the sofa, leaning onto it with his elbows, which caused his back to arch slightly, thrusting his feminine ass out. Foster loved his ass, and considered his good fortune that it was his now to own. He reached once again for the bamboo rod. He stood behind Charlie. Holding the end of the cane in one hand, he brought it down right next to Charlie's ass. His other hand took the tip and pulled back slightly, enough to put some tension on it.

"Count, boy." Foster ordered, and released the tip, the bamboo thwacking lightly against Charlie's left cheek. Charlie jumped slightly and yelped.

"One, Sir."

Foster repositioned the cane slightly lower and parallel to the red streak he just left, and repeated what he had just done.

"Two, Sir!" said Charlie.

Again.

"Three, Sir," Charlie moaned.

Whack. Whack.

"Four, Sir. Five, Sir!" Charlie gasped.

Foster switched to the other side and repeated the impacts, making a matching ladder down his ass cheeks.

"Six, Sir! Seven, Sir! Eight, Sir! NINE, Sir, TEN SIR!!!!" Charlie gasped.

Foster paused, then positioned the cane so it would leave vertical marks, creating a crisscross pattern on each cheek. Charlie struggled not to move, shuddering with each strike and voice beginning to waver as Foster finished.

"How many, boy?" Foster asked.

"I...I don't know, Sir."

Foster's hand came down hard, one time on each cheek, cupping it to make full impact.

"TWENTY, SIR!" Charlie yelped.

"And how many strikes with the cane?"

"Eighteen, Sir!"

"That's correct. Eighteen, for the number of years you have been alive. And two spankings, one for being Charlie and one for being Charlotte."

Foster massaged Charlie's warm ass, complete with beautiful red welts.

"Now, how many more do you deserve, boy?"

Charlie's voice wavered.

"As...as many as you think I do, Sir."

"Good boy. But I have another use for your ass right now," Foster said as he slowly pulled the plug from Charlie's ass. Charlie groaned, disappointed that the full feeling was gone, but realizing that Foster was going to fill it again, hopefully with his cock, he did not complain more than that.

"Onto the sofa, boy. Lay prone, legs together."

Charlie followed Foster's orders and positioned himself on the sofa, awaiting him. Foster reached into a cabinet next to the sofa and pulled out a small bottle of lubricant, a towel, and several cleaning wipes. He joined Charlie on the sofa, straddling his thighs. He laid the towel and wipes out next to them, opened the bottle of lube and applied it to his cock. He closed the bottle and set it aside. He still had lube on his fingers, so he reached down and stroked them up and down the crack of Charlie's ass. Charlie moaned in response, unconsciously moving his hips slightly up and down. Foster's fingers found Charlie's asshole, and began massaging it. It opened easily to his fingers, relaxed by the plug that had occupied that space. He slid one, then two inside, fingerfucking his ass, causing Charlie to try to thrust back against Foster's hand. Foster removed his fingers, causing a sigh of disappointment, and wiped his hand dry.

"Hands on your clit, boy," Foster ordered.

Charlie slid his hands underneath him, fingers on his cunt lips and clit, which were both wet.