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Even after a couple months of this treatment, Edwin still couldn't help but whimper at the uncompromising demands he consistently received from the hands of his captors. He didn't know why these people captured him all those weeks ago, and he was never offered anything in the way of an explanation. But he could think of a few possibilities. Maybe this is someone's revenge against his father or his family, a well-known wolf clan with wealth and influence, and he's to ransomed as a high-value hostage. Certainly this couldn't have happened due to anything Edwin had done himself -- after all, he was only nineteen.

Blindfolded heavily, Edwin had no idea where he was or even whether or not the room was even lit. They'd recently moved him what felt like a long distance by truck to this new place, resulting in him having no clue where it was or what it looked like, as they hadn't removed his blindfold since he got here. He was extremely glad to leave the "Training Facility", as his Trainers called it, but at the same time he was very nervous about this new development. After all, different doesn't necessarily mean better.

Worse yet, they might decide to take him back there. Edwin shuddered at the memories of what they made him do at the facility. He figured out their ultimate training goal fairly quickly: He was to do whatever was asked of him, without question. At first, meeting his Trainers' expectations was simple enough. Crawl from one end of the room to another. Lick someone's palm. Whine if he needed to use the bathroom. But things quickly went downhill from there. By the end of his stay at the facility he felt confident that at one point or another he had enthusiastically sucked the cock of every trainer in the all-male facility. Early on they taught him that providing service with a degree of eagerness ensured there would be fewer, and less severe, "corrections", so they didn't have too much trouble in getting him to 'volunteer' his muzzle as a warm home for yet another phallus.

He blushed as he recalled his final day at the facility, still fresh in his memory. Standing fully naked with his hands clasped behind his head, he shouted out his sincere-sounding thanks to a room filled with what he believed to be the majority of the facility's Trainers as he pumped his cock into the fist of his primary handler, a rabbit who went by the name of "Trainer Tom". Looking back, Edwin supposed it was some kind of graduation ceremony, but not like one he had ever heard of before. Yelling out his gratitude at being tormented and abused while spewing his load in front of over thirty pairs of eyes, all focused on him, was something he would never forget. That was probably the whole point, he realized.

Now, just a couple days later, here he was. And as much as the wolf didn't want to admit it, he almost wished Trainer Tom was here. At least he always knew what he was suppose to do while under the bunny's guidance. Just as Edwin was getting angry at himself for even thinking about missing his primary keeper, he heard a door open a few feet behind him, followed by footsteps to his left and what sounded like someone taking a seat nearby in front of him.

He heard pages flipped through -- some kind of a report? Perhaps documentation on his training? He was young, but he was old enough to realize these people were serious. And serious people tended to keep good records.

The silence lasted so long that Edwin was startled when he finally heard the man speak. "I'd like to talk to you for a little bit, Edwin. Can you be a good boy for me and listen without interrupting? Just a nod will be sufficient." Edwin quickly nodded up and down a couple times. He hoped keenness to obey was rewarded here as well as it was a the facility.

"Good. Should you be given the chance to speak later, you may call me Master Aric. I don't believe in telling boys more than they need to know, but your case is somewhat special, so I'm going to shed a little light on your immediate future. Please listen carefully. In a few moments you are going to meet with three different men, one at a time. These meetings will last thirty minutes each and no longer, and will be timed by an hourglass which is already present here on the table. The purpose of these three meetings is to decide who your new Master will be, now that your basic training is complete."

Edwin leaned forward, ears fully upright in interest. This is the first he'd heard about any of these people's plans for him. He wished he could see so as to gauge the man's facial expressions and body language, but by this point he was used to not getting what he wanted.

"This decision will be based on a choice -- your choice. For thirty minutes you will be allowed to ask the Master you are currently speaking with any question you wish, and you will receive an honest answer. That's not to say that the Masters will be compelled to provide an exhaustive or detailed response to your inquiries. Only that they must provide you with a verbal reply and that reply can not contain any intentional falsehoods. If you feel that a particular Master is being evasive or purposely misleading with their answers, you should factor that into your choice."

Edwin couldn't believe what he was hearing. He was going to get to choose which of these Masters would own him? For how long? Forever? He had a hundred questions on the tip of his tongue, but he knew better than to ask even one out loud.

"I have one piece of advice for you. Be mindful of how much time you have left. Once the sand runs out, the Master is no longer compelled to address your queries and the meeting is concluded. Also, be polite. One of the men will own you before the day is through."

With that, the man walked out of the room and silence settled in once again. Conflicted feelings rose up within Edwin. He was angry at the situation and at these people who felt they had the right to force him to do these degrading things, but at the same time, he was thrilled to have the least bit of control over his future. Maybe one of these men wouldn't be so bad? Or was slow witted, so he'd have a better chance to escape. He'd have to be careful to ask good questions.

But before he had any further chance to get his thoughts in order, the door behind him open and closed once again. Unlike the last time, the wolf's blindfold was pulled off. Edwin blinked his eyes a few times to get use to the light as the first Master sat down across the table in front of him. A large red dragon, extraordinarily muscular with a stern expression. Edwin couldn't tell how old the dragon was, but he was clearly in his prime.

The dragon stared back at the wolf intently and reached out and wordlessly turned the hourglass upside down. Thirty seconds passed before Edwin realized with a shock that he was wasting precious time.

"What's your name!" Edwin practically yelled.

"Master Bultrek. Stupid question." the dragon stated, as if both were self-evident facts. Edwin gulped. Thinking about it, the master's name really didn't give him any insight into what kind of person the man was, but the question was already out of his mouth before he realized it. Looking at the hourglass, the wolf could already see a small mound of sand forming at the bottom. He'd have to do better.

"What do you require your slaves to do?" was Edwin's second question.

"Whatever I want or that needs doing. Cleaning, errands, cooking." said Master Bultrek, eyes never leaving his potential future slave's. Edwin considered this answer, and realized the Master had a slight smirk. Finally Edwin pieced it together. Bultrek was going to make him ask embarrassingly specific questions by not volunteering any additional information.

"Would you want me to service you sexually, and if so, provide some examples."

The Master replied with a succinct "Yes."

Surprised, the wolf asked "Why didn't you answer my second question? I thought silence was against the rules?"

Obviously irritated, the dragon responded "You only asked one question. The second part was a command. You are the slave here, and you shouldn't allow this ridiculous charade to make you forget that fact."

Realizing his error, Edwin added "What are some examples of how you would want me to serve you?" Then quickly added "In a sexual context, I mean. And not just want, but you know, actually make me do." This was proving to be much harder than Edwin would have thought, and tried once more to actually ask the question that he was trying to express. "Actually, my question is, what are some examples on how you plan to have me serve you sexually?" Edwin sighed, relieved that he finally got the awkward question out correctly. He hoped correctly, at least.

After a brief moment to consider the question the dragon replied "You would be available to serve both me and my guests at any time of day. Both your ass and your mouth would see frequent use, and occasionally both at the same time. You will be under orders to wake me up each morning with a gentle genital slit tonguing, until I become fully aroused, at which point you will mount my cock and ride on it until I orgasm. Afterwards, while I'm still hard, you will clean me with your tongue, wish me good morning, thank me for allowing you to serve me, and finally ask me how else you might provide me with service. If I require it, you will then perform as my urinal."

Edwin blushed furiously at the lewd description, but tried to stay focused. What did the answer tell him about this Master? What should his next question be?

"How do you punish mistakes and disobedience?"

"Harshly. Any slave of mine will eventually behave absolutely perfectly at all times."

"What are some examples of how you punish mistakes and disobedience"

"I do not distinguish between the two, as my slaves are under orders to be perfect at all times. To make a mistake is to be disobedient. For punishment, I use a variety of methods, depending on mood. Clips, needles, wax, electricity, paddles, breathe denial, large enemas, fisting."

Already it sounded unlikely that this Master would be his top choice. Edwin didn't have a high pain tolerance, which is one of the reasons he gave in so quickly to Master Tom's lessons. A single ball paddling was enough to convince him to no longer balk when he was ordered to perform a rim job. Still, he had a handful of minutes left, so he might as well make use of it.

"Have you ever killed a slave?"

"Yes, but only once, and not on purpose. He was having difficulty learning to deep throat me, so I used a harness to strap his head to my groin. However, there was not enough slack immediately available, and so when his breath was cut off, he was unable to pull back far enough to remove my cock from his throat. When I realized he was in genuine distress I attempted to adjust the straps, but it had become too taut from his attempts to pull away. I stood up and dragged him to a closet where I kept a pair of shears, but by the time I cut off the harness it was too late."

Edwin felt a chill come over him, and despite being appalled at the explanation, he couldn't help his curiosity. "Did you still manage to cum while this was happening?"

"Yes. The desperate expression on his face and the frantic convulsions of his throat brought me to climax."

"Have you used that or a similar harness since the accident?"

"I have, but I now take additional precautions."

As Edwin thought about what he had just heard, the last of the sand found its way into the bottom of the hour glass. Noticing this, Master Bultrek stood up and left the room without another word. The wolf realized he probably should have spent this time coming up with good questions for the next Master, but he couldn't get the mental image the slave boy out of his head. The dragon hadn't specified a species, and so in Edwin's imagination it was a wolf that was living out his last painful moments strapped to a dragon's cock.

These grim thoughts were interrupted by the next Master to enter the room. A bear who was even larger than the dragon had been, but not nearly as well defined. He obviously was in the habit of eating well, as he had a bit of a larger belly too. Despite this, he was clearly still very strong.

Unlike the other Master, as the bear sat down he immediately said "Hello pet. My name is Master Daon, but you can call me Daddy." and then proceeded to turn the hourglass.

Edwin remembered what Master Aric said about being polite, so he replied with "Thank you, Daddy. Could you provide some examples on how you punish your... pets... who misbehave or are disobedient?"

The bear looked up towards the ceiling as if pondering the question. "Well, let's see. I don't have any pets right now, and I only plan on having one for the time being. But I guess I would take away their toys and sometimes send them to bed without any dinner. They would also have to finish up their chores before they were allowed outside to play. Usually they'd just need to have them done before evening, and could do them throughout the day as they chose."

Wow, Edwin thought. This is already night-and-day compared to the last asshole. If the third Master doesn't pan out, this guy could be a good fall back. Though the words "pet" and "daddy" made him a little nervous.

"Do you plan on having me service you or others in a sexual way? If so, could you go into detail on what that would entail?"

"Oh, I'm so pleased you asked! I have a fully staffed estate, and while your main concern would be for keeping your Daddy's needs satisfied , I would also allow the cooks, cleaners, servants, etc to use you for release, when you aren't otherwise occupied. It's actually going to work out really well, since my staff is all male and I don't allow them to bring their girlfriends or boyfriends into the household. So you would be the only girl, and as such it would be your duty to take care of the men around you.

Edwin could only blink at that for a few moments. "I'm sorry, but you must be misinformed. I'm a boy."

"Well, that's all changing the moment I officially become your Daddy. I already have a wonderful dress picked out for you, waiting in the car, and I can't wait to see you in it. Just wait until you feel the panties I purchased for you, too! Very expensive, but they feel so amazing it's worth it. I won't be able to keep my hands out from under your skirt." the bear said, clearly getting excited as he reached under the table to adjust himself.

"But I have a penis!" Edwin blurted out, panicking. "Surely you'd want a umm, natural female to be your pet?"

"Well, ideally yes, but I've already been on the waiting list for a pet for over two years, after paying all that money in advance. But when I saw your picture and read your description, I knew you'd be perfect. Don't worry about the penis, either! I've got just the thing to lock that naughty thing away." the Master said with a gleaming smile, and then reached into his pocket before setting a small clear plastic device on the table.

"What is that?"

"That, my beautiful pet, is a chastity device. It goes over your sheathe to keep your panties from getting stretched out from any erections. Then I just use a couple small locks and, well, you know what they say: Out of sight, out of mind!"

"How long would I have to wear it!"

"Oh you pretty thing, what I'm trying to say is that once that goes on, it will only ever come off for cleaning, which will be handled quickly and professionally by one of the servants. Neither of us will ever see your bothersome little boy cock erect again. Me because I'll be in a different room while you're being cleaned, and you because you'll be blindfolded."

"Will I get to cum while I'm being cleaned?"

"Erections, jerking off, and spewing cum are things that boys do. If you go home with me, your last orgasm, as you understand them, was THE last. Understand, missy?"

Almost not believing that he was actually hearing this, Edwin thought about what that would mean if his last orgasm ended up being that mortifyingly shameful cumshot he performed in front of all those people. He'd much rather take the dragon over this loon. But just then, he realized that he never asked the Dragon about how and when he'd be allowed to cum. Shit! It simply hadn't occurred to him that would be something you needed to ask about. Of course no one would be so cruel as to lock away your cock for the rest of your life. But clearly no one ever told this Master that. And he had no idea how the dragon felt about the subject of slaves earning release.

Edwin sat in silence for a couple minutes, absorbing and coming to terms with what he just heard, when suddenly the bear volunteered "Well, since you don't appear to have any more questions and we have a few minutes left, I might as well let you look at what you'll be serving for the next many years."

Master Daon stood up and Edwin couldn't help but notice the huge pant's bulge the bear was displaying. In a move almost too swift to follow, "Daddy's" pants and underwear were thrown to the floor. In their place was a massive ten inch cock, which the Master was clearly proud of. Grabbing it with his right hand, Daon bobbed it gently up and down in direction of the pet he so very much desired.

Seeing an astonished expression on the wolf's face, he attempted to reassure him. "Don't worry, little lass. I'll be careful and take my time as I get your mouth and cunt comfortable with this. We can even use the car ride home to spend some time getting you use to the taste. I haven't cum since I was handed your file a few days ago, so your Daddy very much needs release. Men need to cum regularly so they don't feel backed-up and horny all day long, which is why you are so very needed on the estate."

That he had just explained to the young wolf that the slave would be spending the rest of his life backed-up and desperately sexually frustrated didn't even seem to occur to the bear.

The bear started slowly jacking off, oozing the occasional drop of pre-cum on to the floor. "Yes, you're the perfect little girl, and you'll fit in wonderfully at my manor. And once you're settled in, I'll love showing you off in public even more."

Edwin wordlessly watched as the clearly mad Master jerked his hugely thick meat at this fantasy. A dark fantasy that Daddy was going to try and pull Edwin into. Well, not if he had any say in it. And thankfully, he did.

The rest of the time ran out as he continued to watch Daddy stroke himself while looking at the slave in an expression that Edwin could only describe as "ravenous". He expected the Master to cum, but instead he simply used his underwear and pants to contain the gigantic beast again. Edwin felt queasy as he realized that the bear expected to soon be depositing the contents of his proportionally-large balls into the young wolf's mouth and stomach.

After he left the room, Edwin let out a huge breathe in relief. He knew that he would take the dragon over the bear, if it came to it, so at least he'd never have to see Daddy again. Unless the dragon invited him over, he supposed. But that wasn't worth thinking about now.

Moments later, the third and final Master entered the room. A modestly sized boar, smaller than the other two Masters, with tusks sticking out of either side of his mouth. The new Master took a moment to look at Edwin, and then flipped the hourglass.

Edwin knew he had to make this one count. He couldn't afford any more guess-work than he'd already left for himself. He had to be sure. This was potentially the rest of his life he was talking about, if he couldn't find a way to escape.

"Do you currently own any slaves?"

"A couple yes, but I'm going to be selling them if you end up going home with me."

"Would you sell me one day too?"

"Perhaps, but I'd make sure you went to a good home, just like I'm doing for my current slaves."

"What's your definition of good?"

"Hah. You're smarter than your file gives you credit for. I'd be looking for a home that wouldn't permanently damage you, and took care of you in a way that was consistent with what I felt your needs were."

"What do you consider to be your biggest turn on?"

"Interesting question. I've been told to be completely honest, so I'll just come outright and say it. Humiliating slaves."

"How do you humiliate them?"

"Well that depends on the slave, doesn't it? If you hated public exposure, I'd jerk you off on a stage in front of a thousand people. If you cared a great deal about your appearance, I might put absurdly large piecing all over your body and force you to be erect at all times."

"How far would you go? What if you decided that I would be humiliated by blowing a feral wolf? Would you make me do that?"

As soon as Edwin saw the boars face, he knew he made a terrible mistake. "Would I? Oh yes. In fact, if you react then like you're reacting now, I'll buy a whole kennel of feral males and then record you servicing the entire pack. We'll have to try it out, won't we? It doesn't matter that watching you get knotted by a big feral wolf doesn't particular turn me on. Your shame and embarrassment is sure to get my rocks off in a big way."

It was an answer that made Edwin dread the future. He could no longer pretend there would a benign option. No matter which choice he made, intense shame and humiliation were waiting for him.

"What about allowing me to get off?" Edwin didn't want to any more specific than he had to now, afraid of giving the boar any more ideas.

"That's the carrot. If you don't make me drag you up to that stage, or make me bind you so that those wolves can have their way with you, I'll let you have your release. Of course, I'll also probably make you cum in a bowl and then watch you lick up your own spunk. There will be a great amount of trial and error to see what makes you blush the hardest, or squirm the most."

He hated to admit it, but this was starting to sound like the least offensive of the three Masters. After all, he didn't have any clue how often the dragon would let him cum. He could even have castration in mind for the wolf. Edwin just didn't know.

Before time ran out, Edwin having made his choice, decided to try a different tactic.

"Master, may I see you in the nude and erect? I'm strongly considering making you my choice."

Edwin wasn't sure what reaction he expected from the boar, but his future Master almost seemed a little put out. Maybe that wasn't humiliating enough to get his juices flowing?

"Very well. But if I do, you have to tell me which Master was your last choice, and why. And then you must blow me."

The boar was already stripping with the expectation of obedience from the wolf. Edwin supposed if he was going to spend years being this Master's slave, getting started now couldn't exactly make things worse.

"My last choice was Master Daon, the bear, or Daddy and he liked to be called. He was going to dress me up like a girl, lock my cock away into some device for the rest of my life, and make me relieve an entire estate's sexual needs."

The boar merely nodded and he walked up to Edwin, pushing the wolf to his knees. His keen nose was inches from the Master's aroused eight inch tool, which was starting to press gently but firmly against his lips.

"Master, I forgot to ask you your name?"

"It doesn't matter at this point." he said matter-of-factly, and cut off any possible further questions by jamming almost the entire length of his cock into Edwin's muzzle in a single thrust. While he was glad that unnamed Master had obviously washed not long ago, he couldn't help but notice that the taste was still strong. He could only guess at what it would taste like if he had sucked the boar off right before he had showered. Though, Edwin supposed that in the days ahead he'd get an regrettably specific answer to that question.

The boars hips quickly picked up speed, and the slave realized that the Master was probably trying to beat the clock. He probably had to leave the room within moments of the sand running out. Edwin looked up to see his Master was also looking at the remaining time, and noticed that his expression changed as he seemingly arrived at some decision.

The boar pulled his saliva coated cock out of the wolf's mouth, made him stand up and then turned him around, before pulled Edwin's hips towards him. Rather than penetrating him, though, he simply let his cock nuzzle up against the wolf's cheeks before turning them both around to face the table.

Edwin suddenly felt the Master's hand firmly massaging his partially unsheathed cock. His time at the Training Facility had prepared him for satisfying any unannounced whims of his betters, and since it had been a couple days since he last came he was already fairly close to cumming himself.

The boar who wouldn't give his name picked up on this quickly, and into the wolf's ear he whispered "In just moments I'm going to have to leave this room. Beg me to make you spew your load, and while you're coming, shout 'Daddy, your pet is coming!' as loudly as you can.

It seemed like an odd request, but Trainer Tom spent weeks drilling the need to obey any and all commands into the wolf, so he immediately complied with "Master, please let this unworthy pet spew his load for you! Please, sir!"

"Cum as hard as you can pet, and do your best to remember how being jacked off with my hand felt"

Edwin felt the Master's left hand come up to squeeze his knot, while his other hand became a blur over the wolf's six inch cock. As he began to shoot his load in repeated strings across the table and floor, he made sure to scream "Daddy, your pet is coming!!" to what felt like the entire building.

A few moments later, the door opened and a cheetah he could only assume was Master Aric entered the room. Confirming this suspicion with the sound of his voice, the cheetah asked the boar "Can we assume that the slave has made his choice?"

"Yes, Aric. The pet is to be Master Daon's."

"No! Wait! You said I'd be able to make a choice! My choice is the boar. Not Master Daon!"

Master Aric, calm in the face of the youth's outburst, replied "Correct, I did say you had a choice to make. And you've made it. I also said our decision would be made based upon that choice. It is our decision to grant you to the Master you least desire. I'm sure you're curious as to why we would do such a thing, but as I told you already, I'm not interested in telling boys more than they need to know."

Edwin tried protesting further, but the boar quickly muzzled him with a gag he had produced from somewhere.

"Thank you Master Mason. You may leave us."

Before taking his leave, the boar he now knew to be called Master Mason leaned into Edwin's ear, and while rubbing his still hard cock against the wolf's backside, whispered "Having a slave beg me for his last orgasm, and then scream his thanks to his new Daddy while cumming, the same bear who is taking this pleasure away for the rest of his life, will be a memory I treasure forever. I hope that you come to feel the same way."

A few seconds after Mason left the room, Daddy entered. Edwin fervently shook his head 'no', mumbling objections through his gagged muzzle, while backing away from the smiling bear. In Master Doan's right hand was a bright pink dress on a coat hanger, and in left was a small chastity device. Edwin wasn't sure which scared him most, until he noticed the impossible to miss cock, pressed against the fabric of Daddy's pants. The cock that Edwin was destined to serve. Men have needs, after all.