The Pretty Boy Sleep System

by Kevin's Path

11 Jan 2016 2601 readers Score 6.1 (24 votes) PDF Mobi ePub Txt


Previously: Bobby, an aspiring underwear model, got a job sleeping naked chained to a mattress in the display window of a high-end bed and bath store. An unscrupulous salesmen sold Bobby as a bedding accessory. His new owners then got buyer's remorse and consider returning him. Being resold as secondhand goods would be a fate worse than death for Bobby; so, he goes all out to make them happy.


“Hi Sir,” Bobby came to attention when he saw Terrance come in the room.

Terrance said, “From now on, you will call me Massa,” which sounded all rather Darth Vadery to Bobby, but he was more than eager to comply.

“OK Master … owww!” 

Hey! Terrance was armed with a fly swatter, and it stung! He’d picked it up off a dresser table.

“You didn’t listen. ‘Massa.’ The ‘t’ is silent. And you are not OK. A free man is OK. A slave is either good or bad, and that’s it. Got it?”

“Got it … Massa.”

“Here, take this pussy boy. I’m giving you a present.” He kicked off his dress shoes and handed to him shoe polish, a dauber brush, and a buffing cloth.

“Figure out how to use this without making a mess.”

Bobby thought he was supposed to smear the polish out of the can with a finger and immediately made a mess of that, which prompted another smack at him with the fly swatter.

“I thought I just told you not to make a mess. You use the brush to put the polish on, not your fingers.”

Bobby held onto the sole of the shoe and started to do a tentative, spotty job of applying polish all around the heel and the uppers using the brush. Terrance observed unmoving, neither expressing approval nor disapproval, up to the point where he smacked Bobby square on the front of his cock with no warning, which really hurt.

Bobby put his hands with the shoe in them in front of his cock and said, “Massa … look, I’m really sorry. I want to learn, but I just don’t know how to do it.”

Terrance said, “I know, and I’m teaching you.”

Terrance’s preferred method of teaching was to present you with a task, tell you little or nothing about how to do it, but give you clues along the way that you’re doing it wrong in the form of stinging, precision strikes on your unit. Bobby now understood that the teaching could not continue until he lifted up his hands away from the area where instruction is delivered. He lifted up his hands with the shoe and started to polish again, which prompted another well aimed strike.

“Owwwah!”

“Could I have a clue?” He got another smack.

Massa was going to stand there silent and keep hitting him until he changed something, but what?

“Shoe laces? I’m supposed to take the laces out, maybe?”

Bobby unlaced the shoe and put the lace over his shoulder, and he warily started to polish again, staring at Massa, looking for some sign.... He didn’t hit Bobby, so he was on the right track.

Proceeding further along in this way, Bobby thus learned an entire procedure for shining Massa’s shoes by trial and error, receiving lots of instruction via his cock and balls.

Bobby in his good-natured way also wanted to share some constructive feedback. “Massa, just so you know for your information in the future… my balls are really, really sensitive; so, you don’t actually need to hit them that hard.”

Massa smiled. “Really? Why thank you Mattress for giving me that FYI.”

“Mattress, this is what I like to call a teachable moment. Now, you were given to me as a present. You were purchased from a store as a gift. That makes you property. I don’t really want you, but it makes you my slave for now. And, I feel as though I would be derelict in my responsibilities as the master of a slave if I didn’t teach you how to talk and behave right. So now, would you please do me a big, big favor and just grab hold of your dick and yank it way up high so that it’s not hanging down in front of your balls in my strike path?”

Bobby pulled up his cock up with some understandable level of wariness and concern, given the way Massa was holding that fly swatter.

“Second of all,…” Terrance made that fly swatter whistle through the air. “Hguuu!”

Bobby’s balls ricocheted, and he felt dizzy. He abruptly sat down.

“… I do not want to hear about how sensitive you are. This is not sensitivity training here. Come on now, get up.”

“Now, ‘sensitive’ is a very big word, Mattress. It has three syllables. Slaves do not use big words, and slaves are not sensitive. From now on, Mattress, everything is either going to be painin you or else it’s not painin you yet. Understand?”

“Yes Massa.”

“So, tell me again about your balls, Mattress.”

“My … balls are paining me.”

Massa hit Bobby again. He made no sound but started to double over. Bobby complained, “Aahhh, what did I say wrong now?”

“Stand up straight when I am instructing you, Mattress. Now, repeat after me: ‘is painin.’

Bobby repeated “is paining…” but again Terrance walloped him. He’d switched his grip and did a kind of a backhand this time.

Terrance said, “Do not flinch away from me, Mattress. The ‘g’ is silent. Again.”

“My balls … is painin me.”

“Now, what did you say to me right after that?”

“I said…” Whack! Terrance hit him again.

Terrance said, “Pull your dick up higher and get up on the tips of your toes, Mattress. You need to pay attention to the tense of the verb:

I say; I’s gwine say; I don said; I bin gwine say.”

“You pay attention and learn how to talk right. You and me, we are going to be having lots of conversations like this.”

Bobby tried again. “I don said, ‘What I say … bad … now?’” Bobby braced himself for another hit, but Massa said that he was making progress.

“Now, how do you thank Massa when he teaches you new things, Mattress?”

Bobby took a deep breath. This was a whole new mine field now.

“I say…, thank you?…(ouch!)" Talking with Terrance just hurt like a mother-fucker.

Terrance said, “No. Repeat: ‘I is grayful…’

Bobby said, “I is greatful…(aahah!) ... grayful … to (ouwww!)”

Jesus Christ! What could possibly be wrong with “to?”

Terrance said, “Your pronunciation is off: ‘ta.’”

Bobby summed up, “I is grayful ta ya fo teaching me…(nnggeh!)” 

Massa whipped him again, this time more on his left-side ball, which had been getting less attention.

Terrance said, “No. Wrong again in so many ways. I am teaching you, but you are not being taught: you is lernin.”

Bobby tried one more time, “I is grayful ta ya fo lernin me … ta … talk ... good?”

Terrance frowned slightly disappointed to find no fault with that. The kid was a quick learner.

Massa said, “That’s enough for now. Mattress, do me another big favor? When you see me and come to attention, just automatically yank your dick up out of the way from now on. That way we can save time and get right to business.”

Downstairs at the dinner table, Alvin asked, “Terrance, why in the world are making the boy talk stupid like that?”

“I just think if he is going to be here in this house for a while – and believe me, it won’t be more than just a while – he ought to get a little history lesson and learn something about how to talk and act properly like a real slave. That’s all.”

As an English professor, Terrance was very familiar with the historical context and the construction of pidgin language. A pidgin is a stripped-down lite version of a language that is sufficient only for communicating in a very direct and basic way. A pidgin language is a grammatically simplified means of communication that develops between two groups of people that otherwise have no language in common, such as between masters and their slave property. West African Pidgin English was the only language that slaves could use to talk to their masters on plantations in the pre-war American South. Pidgin English has a small vocabulary and a simple sentence structure. Pidgin worked in the interest of slave owners, because it constrained freedom of thought. Language is thought. There were simply not enough words available to speak or think complicated thoughts in pidgin English.

Mattress would be trained from now on to only speak pidgin to his Massa.

Alvin thought this development was all a little weird, but it encouraged him to see that Terrance was somehow engaged and making a project out of the boy. Maybe, they could keep him after all.

Daddy said, “I’m going to have to spank you now, Mattress. I’m going to have to spank you hard, and I’m going to have to spank you with extreme prejudice.”

Bobby shuddered and tried to prepare himself. Wasn’t that how the CIA finally broke down Khalid Sheikh Mohammed? 

Bobby bent over his Daddy’s knee in position for the spanking with prejudice.

Whack … whack ... whack … whack …

Daddy was a slow methodical spanker who focused intently on the goal of a building inexorable glow that accumulated with each successive stroke until it finally exploded into ass cheeks on fire. And once it reached that point, all he had to do was keep fanning the flames.

Whack ... whack ... whack … whack …

There was no drama. There was no counting. It just continued, on and on and on like the slow beat of a powerful drum.

Spanking has fallen out of favor in recent times, but Daddy was old-school in his approach to discipline. Spanking was a completely new experience for Bobby, because he was post-millennial generation. His parents sent him to time-out when he was a bad child; so, he’d missed that whole character-building experience of being turned over a knee and spanked until his face was as red as his behind. But, he was learning all about that now.

Daddy paused and rubbed his hands all over Bobby’s butt as if he was warming his hands over smoldering coals. “OK. Tell Daddy what you did now. Why are you getting a spanking, boy?”

Bobby sniffled. No. He wasn’t crying, but his head was bent down over Daddy’s knee, and his nose just got a little runny is all.

“I ... sniff … I’m being spanked because … sniff … I played with myself when nobody was home,” which was true.

Bobby had a lot of time alone to himself during afternoons when Paulina was done straightening up and Daddy and Massa were at work. He was on the floor chained to a bed, and it was boring. He didn’t see any harm in entertaining himself as best he could. He would lie down on the floor a few feet away from the bed and masturbate until he shot his cum onto his chest and stomach. He was careful not to spray on the bed, because he knew they’d object to that. Some of it did get onto the wood floor, and he was pretty sure they wouldn’t want that either. He didn’t have access to anything he could use to wipe up with; so, he could only cover his tracks by licking the floor clean in those spots. There was a lot of it, and some usually dripped down into his balls.

He figured out how to lick his own hand like a cat would do and then use it to wash himself clean everywhere until he got himself cum-free, no evidence. Really, he must have known or suspected it was wrong, because he made every effort to hide it. He’d just assumed he was alone in private and could go on pretending forever that it was not happening.

“How many times, Mattress?”

“Umm … I think … eight? … ten times.”

“Wow. You’ve been busy. So, that means we will need to have at least nine more spanking sessions like this one – one for every time, isn’t that right, boy?”

“Yes. Daddy.”

It is not completely true that that Bobby had nothing at all to wipe up with. He did have the buffing cloth that Massa had given him to shine shoes. Massa had started to keep his shoes lined up at the foot of the bed within range where Bobby could reach them. The shine cloth was by now mottled with black scuff marks as a result of his continuing daily efforts to improve.

He was being rather slowly and painfully taught how to do a proper spit shine. He often spit on the cloth. The point is that a cum stain here or there on it would not stand out obviously noticeable. He’d actually thought about using it, but it was sort of a gift and one of the only possessions he was allowed to have. It didn’t seem right to use it that way.

“And what are you NOT going to do from now on?”

“I’s not gwine ta … sorry … I’m not going to play with myself anymore home alone.”

“And what’s the new rule?”

“I ... will always ask my Daddy for permission and never do it alone … unsupervised.”

“And remind me, what’s our other rule?”

“–that I’m gonna try harder not to squirt on the new bed sheets when Daddy is fucking me.”

Alvin rubbed Bobby’s pretty red butt more and said, “good boy.”

He also played with Bobby’s cock, which was hanging down over the side of one leg. It really was a thing to be proud of. It was thick, veiny, and thumped on his leg when he lifted and let go of it. It even had freckles.

“Hey, Daddy, are you playing with my cock because you want me to cum for you now?” Bobby asked.

“No. I’m just admiring,” Daddy said. “Daddy understands you are a growing boy and will always want to play with this, but you have to be closely supervised. We’ll discuss that more after we’re done with all the other spankings you’ve got coming.”

“Thank you for taking care of me Daddy.”

Bobby wiggled his butt under Daddy’s hand, because he knew Daddy would like that. It was so important to Bobby that he maintain a good relationship with Daddy, because Massa was just fuckin’ scary, and there was no pleasing him.

Bobby still didn’t see how they knew what he was doing alone here in the bedroom, but he realized that he was somehow monitored even when he thought he was alone. They could probably see every time he scratched his butt and picked his nose if they wanted to, and he had nothing private that they couldn’t oversee.

As if reading Bobby’s mind Daddy said, “Paulina’s been giving me reports that you’re always a very good and well-mannered boy with her when she comes in mornings. She says you are very neat and clean when she gives you the potty chair, and you never splash. She also says you do a very good job washing yourself and cleaning out your anus when you’re done. I’m very proud of you. You’re doing a very good job.”

“Thank you, Daddy.”

Bobby was reluctant to discuss the potty chair. But, there was something he did want to ask.

“Daddy, may I please shave?”

Bobby’s beard was growing out. His chest was getting prickly. His ass crack and balls were getting fuzzy. He was accustomed to grooming himself much more thoroughly. His head hair was all over the place, because he didn’t have any mousse. A fashion model would never be seen looking so scruffy.

Daddy said, “It doesn’t really matter that much to me, you being hairy or smooth. I think you’re pretty either way. But if it is bothering you a lot, then I will ask Paulina to let you use a disposable razor.”

Poor Mattress didn’t have any idea what he’d done now to make Massa so angry with him. Whatever it was, he was more than eager to apologize abjectly and abase himself in any way and every way. Unfortunately, even that was another mistake.

“Massa, I apologize fo…ouuww! Goddammit!”

“Mattress, how many syllables in ‘apologize’?”

“Four”

“Try again.”

“Massa I … sorry … fo … fo … painin you?”

“Yes. You are sorry, Mattress.”

Massa had decided to hang Mattress upside down from a coat rack and torture his balls that way, because he was inspired by the performance of Jamie Foxx in the movie “Django Unchained.”

Bobby’s feet were up in the air with the chain on his one ankle trailing all the way down behind his back to the attachment point on the bed. The coat rack was put right up against the side of the bed. In this orientation Bobby’s cock hung down on his stomach and his balls flopped forward over it in excellent position. The top of Bobby’s head was less than an inch above the floor, and he had a clear view of Massa’s shoes and the cuffs of his pant legs, but Bobby couldn’t see Massa’s face at all way up where his feet were. Bobby’s wrists were bound behind his back, because his hands weren’t needed to hold his cock out of the way anymore. Incidentally, Bobby’s theft protection device also stuck out clearly visible in this orientation, pointing up between his legs near the base of his sack like an antenna.

“What exactly are you sorry for Mattress? What did you do that’s painin me?”

“No sabi, Massa.”

Massa had changed things up a little. Today, along with the fly swatter he also came armed with a foam rubber coated nerf bat. He now took a swing with the nerf bat to make a solid deep resounding thud on Mattress’s ball bag.

Mattress groaned, “Massa please, really, no sabi!”

Massa had promised Mattress that his balls would start to toughen up and he would get used to this type of punishment, but he was being really rough today. The only practical reason for a slave to have balls is as a means to provide motivation and discipline, and Massa was never letting them go to waste.

“No idea at all, Mattress? Can’t think of a thing? Really? What happened to your neck and your chin and your baby smooth balls that I’m looking over up here?”

“I … I shaved Massa.”

“Where’d you get the razor?”

“From Daddy, Massa.”

“Oh really? Please be so kind as to explain this to me, Mattress. Why are you going around behind my back asking your Daddy for special favors?”

“…”

“Go on now. Explain. There must be some good reason why you would do that. I’m very eager to know.”

“I …, I ….” There was no good way to answer this.

“–because, you know that you were my present, and therefore you belong to me first. Don’t you?”

Mattress agreed, “Yes, Massa. I is yours firs. I is yours firs las … ever way.”

“So I repeat myself, Mattress. Why did you ask your Daddy for special favors before you asked me?”

“I asked Daddy because ... (ooohwoooh!)”

“Try that again.”

Mattress attempted once more, “I … don aks Daddy … cus … whenever (yeaaaow … hha ... ha!)”

“How many syllables, Mattress?

“… Three.”

“Let me help you. The slave word you are looking for is ‘iffn.’”

Mattress tried again. “I don aks Daddy cus iffn….”

This is what Bobby so hated about being made to speak pidgin. If he could just say it the way he wanted to, he could finesse it. He could try to qualify it and cut the tension with some flattery or humor. He could be clever. But now, all he could do was come out and say this outright, nakedly, with no defense at all.

“I don aks Daddy cus iffn I aks you I know you qwine say no.” Bobby braced himself.

Terrance had to leave the room for a minute so that Bobby wouldn’t hear him stifle a laugh. After a fair amount of work he’d gotten Mattress to finally say exactly what he wanted him to say, and when it finally came out in words, it was just so damn funny.

When Terrance came back to the bedroom, he said, “Mattress, you are a fucking genius debater. There is no way I can argue with you. You are absolutely right. I probably would say no.”

Massa stuck the head of his fly swatter underneath of Bobby’s cock and lifted it up. “Mattress, have I ever told you how disgusting your dick is? I notice it even more now it’s up here in my face.”

“Yes Massa. You say dat offn.”

“It smells funny too. I want you to clean your dick better from now on, Mattress, because I don’t want have to smell that up here. Understand?”

Mattress said “I sorry Massa. I pay mo attention…(noooo!),” which resulted in three swats in rapid succession on his nutsack again.

When Bobby’s head cleared, Massa said, “From now on, Mattress I’m just going to give you a little tap for every syllable, because telling you repeatedly grows tedious. What was that now?”

“… I gwine pay mo … mind ta washin my dick so’s it don smell bad.”

Terrance was gently tapping on the head of Bobby’s cock with his fly swatter ready to pounce if he said it wrong. And, of all the wrong times for it to happen, Bobby’s cock got hard when he just kept tapping on it.

“Mattress, I can’t believe this. Are you … are you … deliberately trying to provoke me?”

“No Massa. I never wants ta provoke you.”

“Yes, you are! I think you are getting your filthy, stinking dick hard on purpose just so you can poke it in my face!”

This was some kind of mental cross-wiring Bobby hadn’t known he had. Massa continued tapping on the head of Bobby’s cock with his fly swatter and went on and on about Bobby’s disgusting smell and his pale speckled cock and how offensive it was to have to look at this floppy thing. Bobby’s penis kept expanding, thus becoming ever more offensive to Massa as he kept piling on more ridicule of it.

Girls and guys worshiped Bobby’s cock. Nobody had ever talked to Bobby like this, and he could not make sense of his own reaction to it. When Massa kept on and on complaining how his dick was obscene, disgusting, and smelled, it would start to make him more and more hot.

“I’m in a quandary here, Mattress. I just don’t know what to do. Can I fix this problem by hitting it more, or is that going make it even worse?”

He continued tapping on it. Then he said, “Come to think of it, why am I doing all the work?”

He told Mattress to arch his back reaching his bound hands all the way up behind him in the crack of his own ass until he could get hold of the free end of his mattress tag. “Hold onto that tag and buck your hips forward toward me.”

Massa stood there and made him swing and thrust his hips out to push the head of his stiff cock into the fly swatter himself.

“I think if I had any more time with you I’d figure out a way to tame this monstrosity.”

Terrance, sadly, realized that he was going to have to leave this scene without being completely fulfilled by it. Even though Bobby felt overwhelmed by what he was doing to him, Terrance would have been prepared to go much further. But, the logic of how Terrance’s mind worked was that he could only permit himself to torture a boy to the extent that he actually deserved it.

Terrance knew all about the masturbation issue, which was already being dealt with. He’d really sincerely hoped that the boy would have been dumb enough to use his shine cloth as a cum rag. Terrance had lain awake at night imagining the truly epic punishment he could have given him for that, if only the boy could have just learned to be more stupid and worthy of torment. It was such a regrettable missed opportunity, and it profoundly annoyed him.

“Mattress, I’ve decided that it is time for you to go now. I’m going to call the store in the morning and arrange for them to take you back. We’ve decided to trade you in for a water bed.”

Bobby was completely taken by surprise. He understood now that he’d screwed up a little and pissed off Massa, but he didn’t think it was irreparable. He was really trying to fit in here, and he definitely didn’t want to be resold.

“No. No. No. Massa, please. I wants to stay. Don’t trade me fo no water bed, please, please!”

Terrance said, “I’m not going to argue with you about it. Maybe, you should go and beg your Daddy and wiggle your ass at him to see if you can get a different answer. You’re really good at that.”

“No. No Masa. I qwine aks you firs ever time.”

“Actually, why even wait until tomorrow? I think there’s still time that I can contact your store today. The sooner we get you out of here, the better. I’ve got to go look for that customer service number.”

Terrance just left Bobby hanging there upside down. Hot tears began to stream upward into his chestnut hair. Suddenly this was all over, and there was nothing he could do. He’d tried his best to please them but totally fucked it up. He was going to be secondhand goods and go to ruin. After he had hung there alone for some time he was able to finally make peace.

“I surrender. I’ll accept whatever is meant to be. And, I’ll try to be brave about it when they come to take me away.”

Downstairs at the dinner table, Alvin asked, “Terrance, please level me. After all this…, you don’t really mean to trade the boy in for a water bed, do you?”

“Oh hell no,” said Terrance. “We will not be trading him, just yet. I am somewhat perplexed. But, I sense he still has lots of potential to fuck up and be tormented for it in the future.”

“But, Alvin, don’t you go letting him know that. I mean it – not an inkling. I am looking forward to months, maybe years, of him all the time, hop to attention – yes Massa, no Massa, sorry Massa – worrying about us trading him in. Don’t you screw it up. Remember he is my present, not yours.”

Alvin said, “Terrance, sometimes I just can’t even comprehend how you can get to be so evil. But, it’s part of what I love about you, baby.”

“I know you do,” said Terrance.

Although he would never be allowed to know it, Mattress won out. He had succeeded in delighting both of his owners so that they would not want to let him go. He would not be unchained, but neither would he be resold as secondhand goods. He would never end up hitched to a vibrating bed in a pay-by-the-hour motel in Vegas. Despite obstacles and challenges, he achieved for himself a favorable outcome. He was a lucky boy.

It’s true that some things were painin him. But looking on the bright side, many other things still weren’t painin him – yet.