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"I was wondering when you'd ask about that."

Of all the potential responses Madam Whitecoat may have had, this was the one she expected the least. When Jackie Dickface told the mistress of the brothel that she was planning on leaving and travelling the country for a year, she had expected anger, rage, denial. Acceptance was the least in the long list of emotions.

"You... were?"

"Of course!" she replied. "Jackie, most Jakkai around your age want to travel and see the world. The reason many don't is work and relationships, and seeing as the former makes the latter more difficult for us..."

"People in our line of work tend to go on a journey at my age?"

"Exactly! I mean, I might have gone myself if I hadn't figured out I was aromantic by then."

Silence reigned as Jackie reconsidered the situation.

"So... are you fine with me just going?"

"Absolutely not!"

Jackie's expression spoke volumes.

"Honey, I'm fine with you going on a trip. What I'm not fine with is you 'just going' on one. Have you considered where'd you go, how'd you get there, what'd-"

"Ah, stop! Yes, I've already made some plans. Right now, I'm planning on leaving town with the trading caravan come spring. I'll travel with them until we get to the port, and then... I'm not sure. I might take a boat somewhere, travel along the coast, I haven't really decided."

The Madam took a moment to consider Jackie's plans. "That's not a terrible start. However, since your plan falls apart after one town, it's clearly just that; a start. Besides, you haven't even considered costs yet. Food, water, and somewhere to sleep may end up costing you quite a bit." The older Jakkai paused for a moment as an idea began to form. "For your trip, you'll be best to stick to populated areas, namely the coast. And since you'll need provisions and shelter... Hmm..."

"You have a plan, don't you?"

"The start of one. Give me a few days and I'll get back to you." Whitecoat grabbed her jacket and headed toward the door. "In the meantime, start making plans for yourself. Things you want to do, see, the sorts of people you hope to encounter. Date plans, backup plans, clothing, everything!" The madam's gestures became more extreme as she went. Her hand slammed against the wall with the final word. She quickly clucked the injured limb. "Oops. Keep an eye on the brothel Jackie, I'll be back later."

Before Jackie could reply, the madam was out the door on her mysterious errand. The younger Jakkai would just have to wait and see what the older Jakkai was planning.

---

The wait ended up being two weeks.

Every morning, both Jackie and the Madam would meet in the kitchen for a light breakfast before they set off on their morning rounds. After satisfying a few customers who liked to start their morning with a bang and collecting their dues, the two prostitutes would return to the brothel. There they would freshen up before facing the rest of the day, whether that was running the brothel, running errands, or running down prey... or attempting to, at least. Since the two Jakkai would normally get back at different times, they'd use that morning meal to plan out the day. This morning was a little different; Whitecoat simply told Jackie to wash up and wait for her if she beat the madam back to the brothel.

The prostitute was distracted throughout her morning routine. A few patrons noticed her slight lack of attention, but none of them cared to comment on it. A simple question was nagging the back of her mind: What was the madam planning? In the two weeks after Jackie informed Whitecoat of her plans, not one word on the topic had passed between the two, and thus the topic had fallen from her mind. Even now, it never occurred to her that the two events may be related. Nevertheless, she was a professional, and left behind her a series of satisfied customers.

As the madam had expected, Jackie was the first to return to the brothel. In the time she had before Whitecoat returned, the younger prostitute made herself comfortable. The first thing on her after-work relaxation list was a wash. It was always a little surprising to Jackie just how good it felt to wash the sweat and sex out of her fur. After that, she moved on to the second item on her list and changed her outfit for a clean one. If she had not needed to wait on madam, Jackie might have gone to run errands or moved on the third item on her list and read a book. As it was, the Jakkai just took a seat in the parlor and let her eyes rest.

If the length of Madam Whitecoat's significantly longer client list and Jackie's short little client list was ever compared, the time frame for their morning rounds would seem absurd since, despite the incredibly different list length, the madam always returned to the brothel only a little later than Jackie, if she did not arrive first. Some would chalk up this difference in speed to experience, and they would be half right. Experience certainly played a role in that difference; however, clientele was a much more important factor. While many of Jackie's customers wanted sex, talk, and cuddling, the madam's customers often wanted one or two of those, if they wanted any at all. Many of her clients were older Jakkai, mated with a life-partner; still, the prospect of a morning quickie when their mate was not up for it kept them on her roster. Thus, she could speed through her round, hitting up a greater number of potential customers than Jackie in the same time span. Ironically, this also meant Whitecoat brought in a little less than her apprentice on a regular day.

When the madam returned to the brothel, she quickly found Jackie waiting for her in the parlor. That is, if someone who is asleep can be said to be waiting. She gently shook her younger charge's shoulder, awakening her.

"Already washed up and changed, I see," noted the madam.

Jackie rubbed rubbed the sleep out of her eyes and yawned. "Uh, yeah... Is that okay?"

"I was going to make you if you hadn't already. Give me a moment to clean myself up and we'll head out."

"Okay, but..."

"I'll explain on the way, don't worry. Just take a seat for a few more minutes, and don't fall asleep this time."

Jackie almost seemed dejected as she plopped back down. She had really been hoping for answers to the questions that had been nagging at her all day, but it seemed that she'd have to wait a bit longer. The prostitute pondered what the madam could be planning as she waited.

Fortunately, the wait was short. Whitecoat cleaned herself up with the speed of many years of practice and returned within minutes. Then, both of the sex workers left the brothel and set off for their destination, with the madam in the lead.

"So, Jackie. You still want to travel, right?" the madam asked.

Things finally clicked for Jackie. "Oh! OH! Oh, yeah, I still do."

The madam smiled, knowing what had just happened. "Well then, you're in luck. I spoke to the caravan manager, and we might have resolved the issue of your funds, route, and supplies... If things go well."

"And if they don't?"

"You'll have at least met the caravan manager and let him known you'd like to travel with them come spring," Whitecoat responded, with a shrug at the end. "Either way, you make progress, although I'm quite certain you'd prefer to succeed here."

"Why?"

"Because, if you do, the only cost to you will be your time."

"I... I don't follow."

The madam chuckled. "Then let me put it to you simply: I convinced the caravan manager to consider taking you on as a temporary apprentice."

Jackie almost missed her next step. "You what!? That's incredible! But how?"

"It was pretty simple really. The caravan manager is one of my regular customers, and he normally just wants to cuddle or talk. Evidently, they're normally a few hands short during the caravan. During one of his sessions, I mentioned that my own apprentice was looking to travel with the caravan. He asked a few question, I gave a few answers, and he said he might get back to me with something. A couple days later, he came by the brothel to tell me that he could take you on as a temporary apprentice, if you were up to his standards."

"And those standards include...?"

"He didn't explain. However, you will need to be able to make a sale... But I'm quite sure you can do that."

"... I don't think our method of sales is the same as theirs."

"Ah, but what does it matter so long as it works?"

"I-"

"Oh, we're here!" interrupted the madam, turning to the building on her left.

Jackie followed Whitecoat's gaze. The hanging sign, shaped like a caravan wagon, made her quickly agree with the older Jakkai. As the pair walked in, more evidence asserted itself. The walls were decorated with a variety of well-worn maps and wagon wheels. Most of the maps showed the whole country while a few just illustrated the area around a city or town; however, all of them had the major roads marked down in detail and with precision. On each map was a colored line that always included Edunnam, when it could. The younger Jakkai quickly deduced that the maps showed the caravan's trading routes. The wagon wheels showcased old wheel designs, new wheel designs, and the pounding they took while in use. Some of the wheels included had a little plaque, noting the age and distance of the wheel. A few of those numbers made her jaw drop.

As they approached the counter, Jackie noticed two things. Firstly, that it was unmanned, but secondly that a few documents displayed behind glass underneath it, proudly shown but protected from people. A quick glance revealed why. They were the group charter, trade agreements, and other key documents, things the public should be able to see but were too important to be handled. One document in particular caught her eye, and as the prostitute read out the travel rates the caravan charged, she suddenly became incredibly grateful to her madam.

"Jackie," Whitecoat said softly, drawing her companion's attention away from the potential cost of her trip, "Are you ready to do this?"

The younger Jakkai took a deep breath and slowly let it out. "I am now."

The madam smiled at her charge before she struck the counter's bell.

DING DING

Immediately, there was a commotion from somewhere inside the store. While Jackie could not identify the source immediately, it soon resolved itself into the hurried steps of a Jakkai descending the stairs. A door to the side of the counter suddenly opened and nearly slammed into the other wall as a Jakkai from Jackie's generation hurried into position behind the counter.

"Welcome to the office of the Edunnam Caravan, how may I be of service?" he asked, grinning. With an extra pointy tooth hanging onto his lip, Jackie felt like she should know this Jakkai. After all, he was easily identifiable with his tooth, and the brightness of his fur should have made him hard to miss, yet the young prostitute found herself unable to identify the male with whom she should have grown up. Even his markings were a mystery to her. In the end, she gave in to curiosity.

"Hi there, I'm Jackie Dickface. Have we met before?" she asked, offering the stranger a hand to shake.

A quick glance at Jackie's face markings answered any questions the other Jakkai might have had. "No, I think not. I only came to Edunnam after I became Master Rosebud's apprentice. My name is Shadan Sharptooth," he replied as he shook her hand.

"Ah, well... That explains quite a bit then."

"Shadan, would you mind letting Master Rosebud know that Madam Whitecoat and Jackie are here to see him?" requested the older Jakkai.

"Sure thing! I'll be back in a moment."

As Sharptooth thundered up the stairs, Whitecoat turned to face her apprentice, revealing an enormous grin. "Surprised to meet a Jakkai from outside Edunnam?"

"Well, yeah. I mean, it's not like most apprentices come from a whole other village to learn a craft."

"Hmm, you'd be surprised. To be honest, I'm fairly certain that our village might be one of a small number who do these apprenticeships. Besides that, there's been a few apprentices from places outside Edunnam. They've mostly been for trades that travel a significant amount; after all, that makes it much easier to find an apprentice who fits the bill. And of all the traveling trades, I would expect the caravan master to travel the most."

"I guess that makes sense," Jackie agreed, "But how come I haven't noticed any other Jakkai from outside our village? You said he wasn't the only one."

"Oh, that's easy. It's because-"

A roar of thunder from the stairs silenced Whitecoat before she could finish her sentence. A moment later, Shadan was standing at the bottom of the stairs. "Master Rosebud would be delighted to see both of you now."

"Excellent, Mr. Sharptooth. Would you mind leading Jackie and I to his office?"

"It would be my pleasure Madam."

After swiftly ascending the stairs, Jackie found the second level of the office to be much less organized. Crates and barrels of stored goods took up half the space, while old caravan parts consumed the other. A thin bit of unused space was all the way available to get through. Jackie found herself staying especially close to Shadan as the trio of Jakkai wormed their way through the mess, fearful of what might happen if she got lost. Thankfully, that did not come to pass. After a few minutes of careful travel, a small space opened up, right in front of a door.

"Master Rosebud, here is Madam Whitecoat and Miss... Err, Jackie for you," said Shadan as he opened the door.

The room inside was more organized than Jackie had expected. It seemed that that the chaos and clutter of the other room was excluded from this room... Or perhaps the other room was messy so that this room could be clear. The room was clean and empty, aside from some filing cabinets, a map or two, some curtains covering the window, and a desk with a few chairs around it, one of which was occupied. The prostitute could only assume that this was Master Rosebud.

Master Rosebud was an older Jakkai, easily two generations older than the Madam, and he had the grey fur to prove it. Despite his age, the caravan master was still quite capable; he had already gotten out of his chair to meet them at the doorway. As he drew closer, Jackie noticed the paleness of his fur, which far exceeded the amount she would attribute to age. It took her a moment to realize that the sun may have also bleached the fur of the caravan master. As he reached a paw out to greet them, the young adult also saw the origin of his name; a three-part cheek marking on the left side of his face that resembled a flower, yet to bloom.

He shook the Madam's hand first. "Madam Whitecoat, so good to see you, as always."

"Likewise. Mr. Rosebud, allow me to introduce my apprentice. Jackie, this is Ringo Rosebud, the caravan master. Mr. Rosebud, Jackie."

He did not look away while he shook Jackie's hand. "Ah, so you're the apprentice. Yes, I can see why you'd fit the trade. Please, step inside my office, take a seat, and we can discuss this... proposition."

While Ringo returned to his seat on the far side of the desk, Jackie and the Madam got comfortable in the pair of chairs set out on the opposite side. The older Jakkai pulled a few papers out of the desk before turned to Jackie.

"So, Miss Dickface-"

"Just Jackie please, sir."

"Fine. Miss Jackie, you wish to join the caravan in our annual trade excursion, correct? Additionally, you are willing to take on a short-term apprenticeship under myself, so that you can be of significant help during the trip. Thus, in exchange for housing, food, and water during the journey, you will do whatever I need you to do. Does this sound correct to you?"

"Yes sir."

"Good." The caravan master leaned back in his chair and crossed his arms. "Now, why should I take you on as a temporary apprentice?"

Jackie was too surprised to say anything for far longer than she would have liked. Once she found her tongue again, the young prostitute nearly went to sell herself like she did to clients. Just in time, she realized that a different sort of sale was needed here. Jackie took another moment and reconsidered her advantages. Then, she made her claim.

"... Well, for one thing, I'm a hard worker with a lot of stamina. I'm used to waking up early in the morning, so I won't need to adjust my sleep cycle. I also really want to go on this excursion and see the world, so I'm extremely motivated to do the best I can. Oh, and I can make a sale!"

Rosebud was quiet for a moment while he thought. "Given your trade, I'm going to assume what sort of sales you made, and say that the methods you used there probably won't work for us. In fact, I'm going to say right now to never use them outside of your trade. Aside from that... Well, I've heard worse."

"I'm sorry sir. I didn't really know that you'd be asking that sort of question before you asked it. I would've had a better answer if I had the time to properly prepare an answer."

"Hmm..."

"Oh, come on Ringo," interjected Madam Whitecoat. "You told me that you were rather shorthanded for this whole thing."

"While that might be true, this is still going to be expensive for me. Aside from the food and water, there's the cost of training her for a one-time job. I need to make sure this is worth it." The eldest Jakkai put a hand to his forehead and massaged his temples. "That said... Jackie, can you read and write?"

"Oh, yes! I even write our signs."

"Good. Do you know your numbers?"

"Yes sir! And can do basic arithmetic. We keep track of our own finances."

"Very good. That saves me from teaching you the more difficult skills, IF we take you on... Hmm... Okay, I got two more questions. Firstly, if I took you on, would you be able to refrain from practicing your trade during the excursion?"

"But... Don't you want me to use what you've taught me?"

"Your CURRENT trade. I can't allow the caravan to get a reputation from bringing prostitutes. A few towns might stop trading with us then."

"Oh! Oh... Yes, I can do that."

"Great. Finally... Can you do something about your face markings? I mean, I don't personally have a problem with them, but I'm worried that some more prudish villages might take some sort of offense and... Why are you giggling?"

"Because I already talked to a friend that, and we have a solution ready!"

"Oh! Excellent! Well then..." The older Jakkai rubbed his chin and sat back in the chair.

After a few seconds, the Madam interjected. "Oh, come on Ringo, you've grilled her enough and she's given a satisfactory answer to all your questions. Just take her on already!"

"Well... Ah, alright," he said as a soft smile spreading from his lips. "Jackie, I'd be happy to take you on as a temporary apprentice."

---

Jackie's life soon fell into a steady rhythm. On one day, she would work for Madam Whitecoat. They would both get up early for their morning round, servicing a few regular customers who wanted a little action in the morning. Afterwards, they would return to the brothel for the next part of their day. For the younger prostitute, this meant servicing customers, running errands, working the front room, or having the day off. Come evening, she'd have dinner and possibly service a customer or two who wanted a longer, more in depth session. Once they were satisfied, Jackie would turn in for the night. In other words, these days were practically the same as her days from before meeting Shadan and Master Rosebud.

The following day would be wildly different. After a quick breakfast, Jackie would go over merchant's depot, the place where she had met with Master Rosebud. There she would spend the day either learning how to lead horses, tie knots, or repair caravan wagon parts from Shadan, or learning how to take inventory, record purchases, or maintain a proper stall front from Master Rosebud. Often times, it would be a mix of many of those, and more besides. It was a crash course education in being an apprentice to the caravan master, with the aim of getting Jackie to the point that she could be helpful rather than hurtful during the caravan. To everyone's surprise, it was working, and Jackie was quickly being competent at many of the tasks she might need to perform on the road. Still, each day brought something new to learn, so all three Jakkai kept at it. On those days, when Jackie would finally return to the brothel, it would be a heavy dinner before going straight to bed, exhausted from the day's work.

The day after that would be the same as the first, and thus the cycle repeated, until spring arrived and it was time for the caravan to leave Edunnam. Still, there were a few interesting things that happened between meeting Master Rosebud and leaving Edunnam.

---

It was quite unusual to start a day at the brothel with a customer at the door. It was even more unusual for that customer to come to the back door, so when someone knocked on the brothel door in the early hours of the morning, before Jackie and the Madam set out on their rounds, neither of them knew what to expect. After a hushed debate, Jackie was sent to answer the door. As she slowly opened the door, she was surprised to find a recognizable Jakkai behind it.

"Haretail? What are you doing here at this hour?"

"It's October 19th, isn't it? I rented out the Dungeon for today."

"Oh my gosh, that's right! I'd completely forgotten about that! Although... You're here pretty early in the day."

"I thought I had the room for the whole day?"

"You do, you do! It's just that... well... Not many people come in this early in the day. You might be waiting for a while before anyone arrives." She left out that someone had to stay at the brothel while a room was in use. There was no reason for her to appear petty.

"Oh, don't worry about that! My Master took care of that!"

"... I see. Well then, head around to the front and either I or the Madam will let you in."

"Okay then!"

As Haretail headed around the brothel, Jackie closed the door and rushed back to Whitecoat. "The Dungeon renter is here and his Master should be bringing folks. What do we do?"

It only took a second for the Madam to pick a course of action. "Well, you booked and talked to Haretail, so you get to watch him too. I'll check in on your morning customers during my round and let them know what's going on. Go get him setup and try to have some fun."

"Mmph... Fine." With a plan in place, it was time to act. Jackie headed over to the brothel side of the house and opened the door. As she let Haretail in, the prostitute turned on the red lamp by the door, opening the brothel for the day. When she came back in, her customer was waiting in a seat. "So, Haretail... You said something about your master?"

"Uh, yeah. What about it?"

"Well-"

The front door squealed as it was opened.

"Carson! How's my little pet doing?"

"Draig! I mean, master!"

Jackie was more surprised at the door opening than the identity of the Jakkai walking through it. She knew Draig Firesnout, apprentice to the local dye trader, fairly well, after all. He was one of her best friends. She knew he kept a large circle of people he liked to fool around with, and his prefered position. Honestly, Draig NOT being the Carson Haretail's master would have been the more surprising outcome for her. Still, his arrival was going to be a bit of a problem.

"Nice to see you Draig. I take it you're Carson's master?"

"Yep! Isn't he just the cutest little pet?"

"Oh, he's definitely cute. So, uh... I hate to bring this up, but did either of you bring a copy of your contract?"

Draig was ready for her. "Yep, just let me just get it out of my pocket here... And here you go!"

Jackie quickly scanned the document, looking through the terms of the relationship. "Well, this looks proper... Draig, why don't you go get some stuff set up in the Dungeon? You know the way to it, right?"

"Doorway on the left, middle room?"

After Jackie confirmed Draig's memory, he headed off for the back of the brothel. Once he was out of sight, the sex worker returned her focus to her customer. "So Carson... I still have a few questions for you. Firstly, are you here of your own free will? No threats or anything?"

"Of course not! You have the-"

"I HAVE to ask these questions. They can be a bit stupid, but rules are rules. Second question: Was the idea for this event your own or your master's?"

"My own."

"Was the deposit your own coin, a mix of yours and your master's, or just Draig's?"

"A mix. I put in a third, Draig put in a third, and a few of his other... toys put in the rest."

"I see... Okay then, what do you want from this event?"

"I.. don't follow."

"You asked for males only. However, I've got both sexes, we've got some toys in the back... What do you want to experience?"

"Oh! Well, I, uh... I want for my ass to get used. I want people to drain their cocks in me, use my hole as a place to dump off their cum... And to blow a few loads myself." The Jakkai's face flushed red as he spoke.

"I see... So you'd be fine with me using it. How about toys or ladies using them?"

"That would be... fine, I guess."

"Good, good... That'll help you get some more attention. Give me a minute, I need to get you a few things from behind the counter." Jackie did not wait for a reply. As she looked through the few items kept behind the counter, Draig returned from the Dungeon, looking pleased as punch. He had taken a seat besides his pet by the time Jackie noticed him.

"Oh, Draig, you're back! Cool," she said as she walked back to the customers, a small bag in her hand. "Did you find everything to your liking?"

"Of course I did! You and the Madam take excellent care of your gear."

"Aww, thank you! Now then, Carson, I have a few items here to help you... prepare for today. Why don't you head to the bathroom and use them while your master and I have a little chat."

"But... I already cleaned-"

"Sorry, but it's the rules; you've gotta do it again."

With a defeated sigh, Carson took the bag and went into the men's bathroom. Once the door closed behind him, Jackie turned to face Draig, a scowl creeping across her face. "So, when were you going to tell me about this?"

"Sorry Jackie, it slipped my mind when you came over to get the dye. I trust this isn't putting you out of anything too important, right?"

"I'm alternating days between here and the caravan headquarters, so my clients are going without service for five days. The Madam will take care of some, but not all of them."

"Oh... Sorry."

"... It's fine. So, what are you looking to get out of today's rental?"

"Oh, well, I just want to reward Carson for his good behavior and chastity. Plus, a few of my other playmates have been looking for a hole to use, so... Why not kill two birds with one stone?"

"And for yourself?"

"So long as I get to use his hole a couple of times, I'm happy with whatever happens."

"So the money you put in towards the rental...?"

"Was just to make it more affordable for Carson. I'm making no claims to ownership here. Does that make you happy?"

"Hmmph... A little." With her questions satisfied, Jackie relaxed and waited for the man of day to return. Since Carson was the sole owner of the rental, she just had to focus on making him happy... and with Draig around to help, it would be a breeze. About a minute later the door to the men's bathroom swung open.

"Uh, Jackie? I finished cleaning myself."

"Ah, welcome back Carson!" said Jackie as she hopped out of her seat. "Since all the preparations are now down, I suppose I can take you back to the Dungeon now. Would both of you please follow me?"

Just like Draig had done earlier, Jackie went through the left door in the back of the brothel. The hallway immediately bent back around in a U-turn, leading to a new section of hall with three wide doors. Jackie walked right past the pair of doors that lead to the vanilla hall and to the Dungeon. With Carson right on her tail, she pushed the doors open, revealing the stone interior, along with a sizable collection of chains, cuffs, weapons, and other toys. It seemed Draig had rearranged things a little when he had been in the room earlier, as a pillory had been moved into the middle of the room. The prostitute grinned as she heard Carson's astonished gasp. She turned to face him with a dramatic twirl.

"Welcome to the Dungeon, sir. Everything in here is free for you to use-"

Jackie was cut off as Carson dashed over to the pillory.

"Master, is this what you picked out for today?"

"Hehe, that's right pet. But what did I tell you about cutting people off when they're talking?"

"... Oops, sorry madam."

"It's fine... I assume you'll be using this heavily today?"

"Yep!" confirmed Draig. "Would you mind helping me get my little pet ready and in position?"

"Uh, sure."

While Jackie was quite certain that Draig did not really NEED her help tying up Carson, she was nevertheless happy to be of service. While Draig pulled Carson's pants and smallclothes down, she pulled his shirt up and over his head. Once he was nude, she led him over to the pillory and held him in position while his master locked the top section in place. The prostitute then went to grab Carson's tail pin it to the top of the pillory, and thus out of the way, and was greeted with a clear reminded of why his childhood name had been "Haretail," as a little tuft of fur was all that was there to greet her.

Once Carson was stuck in the pillory, Draig started to dig through the collection of toys on display. He occasionally grabbed something, but it was clear that he was looking for a few very particular items. For a while, Jackie watched him, trying to figure out what his plan was. Before she could come to a conclusion, he finished, and brought the pile of gear back to Carson. A quick glance at the pile, and one item in particular, told Jackie that she needed to step in.

"Uh, Draig, hold on for a moment."

"What's up Jackie?"

"I see a gag in that pile. Are you planning on using that on Carson?"

"Yes, is that a problem?"

"Just a small one," she said as she stepped around the trapped Jakkai so he could see her face. "Carson, are you okay with being gagged?"

"Of course! I don't think he'd have grabbed one if I wasn't."

"Okay then, but... Ah, right. You can knock on the pillory with your hands, right? Good, then knock on it three times if you want something, okay? It'll be your 'safeword,' so to speak. By the way, you two know that he'll have to take a break around lunch, right? For water, at the absolute least."

"Thank you Mother Jackie. Do you have any other rules for us?" sassed Draig.

Jackie just flipped him off.

The first thing Draig put on Carson was a spreader bar, forcing the submissive Jakkai to keep his legs spread and hole available. After that came the contentious gag, followed by a blindfold. The dye maker's apprentice then tied a strip of cloth around Carson's mouth and another over his ears, robbing him of his senses. Finally, Draig pulled a small, double-banded ring out of his pocket, along with an oversized condom. As Jackie watched, he slid the condom over his pet's cock, then locked it in place with the ring, leaving a large empty space. Jackie soon realized that he had created a cum-catcher for his pet.

"I'm sure you'll appreciate that," Draig snerked at Jackie.

"Actually yes, I do. Thank you."

"Don't thank me yet. It could easily make quite the mess we finish. Besides, it's just there to see how much he cums. The easier clean up is just a bonus."

"Well, I'm not going to complain about it. By the way, when should the rest of your guests arrive? And how many?"

"Well, I told five of my pets to be here at seven o'clock sharp, so that I could use Carson once or twice before they arrived, but I didn't expect so much delay in getting set up. In fact, I-"

The ringing of Edunnam's town bell cut Draig off. Both Jakkai that could hear listened as it chimed twice, thrice, four times, five, six... seven.

"They should be arriving... now."

---

By the time Jackie got the front door of the brothel, six Jakkai were already at the front door and waiting. Jackie was doubly surprised to find an extra person at the door and to find them waiting outside. The first question had an obvious answer; the event was open to the public, and a local had decided that he could really blow a load or two. The second took longer to determine, but she understood why they were outside and not in the lobby once she saw that the lock on the door had somehow re-engaged itself. She unlocked the door with an apology and led them back to the Dungeon.

When the group of Jakkai got there, they found Carson's ass facing them, beautifully lubed and ever so slightly gaped, while Draig rested his elbow on the top of the stockade with a cheeky grin. He graciously welcomed his playmates and the guest to the event, and offered them Carson's hole for their use. A quick jab from Jackie about how perhaps he should have her job soon shattered the atmosphere he was building. While the guests chuckled at Draig's expense, he tried to counter the shot at him by claiming that, if he were a prostitute, he would not be able to spend as much time with his partners as he would like prefer. It was not a very effective comeback.

While Jackie and Draig continued their friendly banter, the guests undressed. Pants, shirts, and underwear started to hit the floor as the six new Jakkai got ready to have some fun. Draig broke off the conversation once he saw one of the guests finish undressing.

"Hey Alex, you're on the smaller side. Why don't you take the first crack at that piece of ass?"

The guest evidently named Alex blushed when his master called him out, but the smile on his face told even more. Once he got undressed, he took the first spot in line for Carson's ass. Since his shaft was indeed on the smaller side, he was able to hilt Carson after a just one minute of pushing and pulling. As Alex started to pick up his pace, Jackie took leave of the situation to do a few jobs.

While Jackie supposed to stay in the Dungeon when it was in use and she was the only brothel worker in the building, there were still a few things she had to do to make sure the rest of the day would go smoothly. Plus, with Draig in there to keep an eye on things, she was sure nothing too bad would happen. Probably. With that in mind to hasten her work, Jackie got busy. The first thing on the list was double checking what she had previously done; namely, making sure the lantern out front was lit and the front door was open and unlocked. After that, she moved the sign advertising today's event to hang under the lamp, making it clear that the event was happening today. With the brothel entrance properly prepared, she moved on to the lobby. After a bit of rummaging behind the counter, she found the signs she was looking for. A quick trip to a closet in the house side of the brothel netted her an easily movable table for the signs. Once that was in the middle of the lobby, she set up the signs. One sign told visitors that there was event going on in the Dungeon, and had directions to it. The other said that none of the brothel's workers were currently available, and directed anyone reading it to look at the events. With that pair of signs, the young prostitute was sure than anyone walking into the brothel would end up in the Dungeon. With those problems resolved, Jackie headed outside to check that the exterior was properly set up. Once satisfied that nothing had changed, she headed back to the Dungeon.

When Jackie got back, two of the guests were sitting down with a wet and limp dick hanging between their legs. Another guest was pounding away at Carson's ass, beating out a steady rhythm of smacks. A quick glance at the way the condom between Carson's legs swang and the young prostitute could guess that Carson had come at least once too. Since everything seemed to be going well, she rested a shoulder against the doorframe and started doing her job; watching.

For a while, things were pretty boring for Jackie. Her job was to just watch Carson get his ass fucked, after all. She finally got to do something after the fifth guest blew his load and the bound Jakkai knocked thrice. However, it was just a simple request for a drink, and after downing a canteen of water, it was back to business. After Draig finished his round as the seventh Jakkai to use Carson's hole, he offered Jackie a turn. She politely declined and Round Two started, with Alex again getting the first go.

The second round started off much like the first. The first two Jakkai to fuck Carson took a little longer than they did in the first round, It wasn't a surprise, seeing as they had already blown their load once and the hole they were fucking was looser. While the third Jakkai was going to town, Carson knocked three times, the signal that he needed something. Once the guest was out of Carson's ass, Jackie ungagged him, only to learn that the tied up Jakkai wanted water. After another canteen of water, it was back to fucking.

However, in the time it took Jackie to get that second canteen, the Jakkai who had just finished using Carson decided that he wanted to use the Dungeon's accommodations. When he went to get tied down to a beam, Draig stopped him and had a brief discussion. Draig's pet then moved over to an X-shaped cross and got tied to that instead. Once Jackie saw her friend slide one of their more stimulating plugs up his butt and start to jerk him off, she understood the situation. She deduced that the guest wanted to get off more frequently, so he had moved to take a fuckable position. In order to keep Carson the center of attention, Draig had gotten his pet to accept a different type of stimulation. With his ass plugged, he would leave everyone aroused and available to fuck Carson, while still getting off himself from handjobs. Better yet, the handjobs could just keep coming, and coming, and coming. Jackie made a mental note to give the guy some lube and check for chafing later.

In the meantime, the third Jakkai in the rotation had resumed fucking Carson. Soon enough, he blew his load. After a few seconds, he got out of the way and let the next Jakkai take his place. Near the middle of the fifth Jakkai's turn using Haretail, Madam Whitecoat finally returned from her combined morning route. She was more than happy to take the place of her apprentice and inform her that she would have a customer tonight. She took it as a chance to refill the canteen before it was requested and as a chance to step outside to get some fresh air. When she returned, Draig had just finished using Carson and once again offered her a shot at the ass of the day. This time, she accepted.

By now, Haretail had been fucked fourteen times, and it showed. His rump was flushed pink from people smacking into it while pounding his ass and his hole staying slightly gaped. A thin trickle of fluid was leaking from it, running down his taint to drip off at his sack. Jackie licked a finger and dragged it back along that path. She smiled when Carson shuddered. As the hermaphrodite undressed, she teased his ass, groping and squeezing his cheeks. When the bound Jakkai started to swing his rear from side to side, Jackie knew it was time to fuck him. After a smack on his ass, she lined up her cock and thrust in.

Penetration was incredibly easy. Having taken seven cocks twice already, this was to be expected, but even then Jackie was blown away. It took just two thrusts to hilt him! However, Carson had a trick or two up his sleeve and as soon as her hips hit his ass, he clamped down. Immediately, it became much harder for Jackie to maneuver her cock; harder, but not impossible. She started to slowly pump back and forth in Carson's hole, working herself up. Jackie had to admit, Draig's pet had a great hole. After a few minutes of fucking the ass clenched around her cock, the apprentice could feel her orgasm approaching. She managed to get four hard thrusts at Carson's sweet spot before she came, blowing her load right against the bound Jakkai's most sensitive spot. Jackie grinned when he squirmed underneath her. Quickly grabbing Carson's cock and balls confirmed her suspicion; she made him cum too.

For both of the Jakkai, the next few second were spent enjoying the afterglow of sex. After that, Jackie carefully got her shaft out of Haretail's ass and gave his rump another smack for being a good fuck. As soon as she turned around, Draig was besides her.

"So... What do you think of my pet?"

Jackie snorted. "Well, for one thing, he's got a great hole."

"And?"

"And-"

The town bell derailed any further conversation, as Jackie stopped to count the number of rings. When the count hit twelve, she sighed and returned to stockage. One of the guests asked her what was going on when she started to unbind Carson. Her response was simple.

"Lunch."

Once Haretail was freed and a butt plug firmly planted between his cheeks, Jackie took him back into the home portion of the brothel. She was unsurprised when Draig followed them back. The prostitute gave her friend and his pet some light soup and water for lunch, offered Carson a chance to clean out his hole, and a chance to relieve himself. While he passed on the former, he gratefully accepted the latter. Once he returned from the bathroom, the trio of Jakkai returned to the Dungeon and got Carson back into place.

When Jackie took a look around the room, she was a little surprised to see the number of Jakkai cut in half. Only three guests remained, namely the Jakkai tied to the cross, the Jakkai who was not one of Draig's pets, and Alex. The latter two had evidently decided to stay and jerk off the first. The prostitute was amused to see the growing puddle of cum in front of the poor guy, but it was what he wanted. When she checking in with the madam, Whitecoat confirmed that three guests had left for home. Of them, one of the guests had called it a day, claiming exhaustion, while the other two said they would be back later. Unfortunately, they had not said how much later.

The first few hours of the afternoon were going to be slow, and Jackie and Madam Whitecoat knew it. Since there were only four Jakkai available to fuck Carson's ass, and a fifth was tied to the cross, it was going to be a challenge to keep his hole filled. Still, they made it work, using their arm and a few dildos when no one's cock was up to the task. The Madam even pegged his rear a couple of times.

Around three o'clock, a new Jakkai walked into the Dungeon and the prostitutes visibly relieved. His arrival meant that people were finishing with their work for the day. This, in turn, implied that the workers could come to the brothel and join the event, which would bring more cocks to fill Carson's hole and let the individuals who had been there a chance to rest. By five o'clock, when Haretail was forced to take a second break, there were ten more guests in the Dungeon and each one had left a deposit in Carson's ass.

As evening fell, the Dungeon got more and more crowded. Many Jakkai came by just to blow a load after a hard day's work. Those that wanted more could wait in line for a second use of the cum dump or take advantage of the what other options the Dungeon offered. Jackie knew there was at least one guy hanging from the ceiling and a pair sharing a longer toy when her client for the night arrived. She spent over an hour with the lady, pleasing her and sharing some company. When they seperated, it was past eleven o'clock.

Jackie was unsurprised to find a stream of people leaving the Dungeon when she returned. While the late hour might have drawn a crowd, the room would need to be cleaned and the prostitutes needed to get up early in the morning. Unfortunately for everyone else, in matters of practicality and fun, practicality won at the brothel. Eventually the only people left in the room were the prostitutes, Draig, and Carson. After over fifteen hours of getting fucked, the bound Jakkai's hole was well stretched and leaking cum. Even with the leaking, his belly looked a bit bloated.

While Draig removed his pet's headgear, a stroke of inspiration hit Jackie. After getting permission from Carson, she quickly grabbed one of their larger butt plugs and slide it into the pet's leaking hole, sealing it. Haretail put his arms over both Jackie's and Draig's shoulders, as they helped him walk over to the bathroom. At the moment, he was too sore and shaking from all the sex to get there without help. Once they got him to the shower they sat him down and Jackie removed the plug, letting the cum leak down the drain. Then, Draig got the ring off his pet's cock and held up the condom he'd spent the day filling. She was surprised it was still intact.

"Are you ready for a cum bath, pet?"

Carson's answer was to look up, close his eyes, and open his mouth. When Draig dumped the condom over his face, his face, shoulders, and legs were instantly plastered white, with splatters of cum covering the rest of his body. The stink of semen filled the shower. For a moment, Jackie was worried Carson was hurt. Then, he spoke up.

"Thank you master."

"You're welcome pet. Now, let's clean you off and get you home. Tomorrow is going to be a real pain in the ass for you."

"Hehe, but it was absolutely worth it. I just feel so good right now! I mean, I'm hard now! After getting railed all day!"

"Yes yes, you got absolutely fucked. Now, if Jackie would be nice enough to turn on the water when she leaves, I can try to get some of your spunk out of your fur before you become a matted mess."

"Thank you master!"

"Yeah yeah."

Jackie covered her mouth to hide a chuckle as she left. Yep, Carson was definitely okay, for now. While those two cleaned up, she joined the Madam in cleaning the Dungeon. After an hour of work, the Dungeon was ready for use, although a few of their toys still needed to be cleaned. A half hour after than, Draig came by to thank them for the night and to let them know both he and his pet were leaving. After a stern warning to take care of Carson tomorrow, Whitecoat let him go, and then both she and Jackie turned in for the night. Jackie was asleep as soon as her head hit the pillow.

---

As the first day of Spring drew closer, Madam Whitecoat found much of her time being spent worrying about the future. Spending most of a year without an apprentice prostitute would be difficult, but doable. She'd done it while training Jackie, after all. Still, she had been ten years younger then, plus training an apprentice had bought her some assistance. At least everyone would be less eager, since they were past the midpoint between heats.

Those were only the problems for the upcoming year though. If Jackie found a partner from outside of Edunnam, there was a good chance that the young prostitute would leave town at the end of her apprenticeship, and then the brothel would just have one worker again. There was also the horrible possibility of Jackie never returning... But the Madam forced that from her mind.

While Whitecoat spent a night in her office considering her options, a polite knock on the door interrupted her reverie.

"Come in!" she shouted. The older Jakkai was unsurprised when Jackie opened the door.

"I just finished up with my last customer of the night Madam. I'm going to turn in for the night."

"Ah, I see. Sleep well then Jackie."

The younger prostitute hesitated as she turned to leave. "Madam, I've been thinking... I'm leaving you in a terrible position, aren't I?"

The madam was momentarily stunned as she realized she was not the only one considering the future. "Jackie, I... It's al-"

"It is not 'alright!'" she snapped back. "It's not 'alright' for me to leave you as the sole prostitute in town, it's not 'alright' for me to leave so many people without service, and it's not 'alright' for me to just go like this! ... But I feel like I must do this. I'm sorry Madam."

"Oh Jackie," the older Jakkai consoled as she walked to her apprentice's side, "I'll be fine. The village will be fine, and we'll all be ready and waiting for you to come back. It's okay." She wrapped her arms around her apprentice in a tight hug.

"I, I... thank you," Jackie said, sniffing to hold back the tears in the corner of her eyes. After a moment of hugging the madam back, she added, "I... I also have an idea that might help you."

"Oh?"

"Ye-yeah, it could even take care of two problems at once. See, since we don't have a male worker - Yes, I know I technically fill that role, but we both know there's a few individuals who don't find the idea of fucking a hermaphrodite arousing - maybe the brothel should try to take on a new apprentice or two during the next Apprenticeship Day. I even know of a guy you might be able to recruit."

"Do tell!"

"He's a decent guy, I met him in the fall. Here, let me write his name down for you. He goes by Randy, Randy Earlyrise."