Paradise Isle, Slave Trade Pt. 02

One aspect she began to understand was that sex, at least for her, now, was becoming mechanical, unemotional. As in, it was just an exercise - a chore to be completed.

And she wasn't pleased by that notion.

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Around the dinner table all they could talk about was the next day's session. They had been warned that day four was anal sex day, and that the first thing they'd all have to suffer through, after breakfast, was an enema, a deep cleaning treatment.

Wyatt and Sutton acknowledged that they'd both suffered through those procedures before. And Wyatt even admitted, embarrassingly, that he'd actually enjoyed the full feeling on occasion. Sutton just said that she found them humiliating when administered by her master.

But none of them were looking forward to a day of taking it up the ass. The prick and pussy lessons hadn't been all that unusual or unpleasant. Those had been familiar activities. The biggest issue they'd all had was aches and pains from the repeated use and abuse of their pussy's, knees and legs.

The next day, after they'd been released from their cages, and eaten breakfast their lessons began with the dreaded enemas. And it was made worse as they were all lined up on their hands and knees, side-by-side, to be filled by four enema bags full of liquids.

And, of course, the process involved several fillings and emptyings, under the close supervision of two stern trainers.

All four of them were embarrassed throughout the process. And, of course, made miserable by the uncomfortable and sometimes painful filling of their bellies.

All of them groaned when they were filled, and sighed when they were allowed to relieve themselves.

They were lectured in the value, and the potential for pleasure, during the process, but none of them seemed to get any enjoyment out of the procedure.

And when that awful phase of their lesson was completed, they began their actual anal sex education.

Only Sutton admitted to having experienced anal entry. And she even acknowledged that she'd enjoyed it, on occasion.

As with their earlier lessons, devices were used to familiarize them with the methods and feelings encountered with fucking and being fucked in the ass.

The first step was for each of them to be fitted with anal plugs, to help stretch their rear holes, and get them used to the feelings of fullness, and the accompanying desire to expel.

One-by-one they were lubed, and had their plugs installed. By one another. Under the trainer's demanding supervision.

The process was difficult for both the recipient and the installer.

Once the plugs were all in place, the class was required to move about, sit, walk, run, stand, crouch, etc. To get used to the feelings emanating from their behinds.

Much to their displeasure, they were also informed, that their current plugs were of the smallest size, with only a 40mm diameter and a thin neck. But every two hours, throughout the day, the things would be swapped out for larger sizes. 50, 60 and finally 70mm plugs, each longer and with thicker necks then the previous size.

"By the time you're finished with today's lesson, your assholes will be able to accept even the largest cock." The head mistress said, happily.

They all groaned at the prospect, particularly Wyatt who had no interested in sex with men. The girls were tired of hearing it...

Next they were introduced to another set of Sybians, designed for anal penetration, and after removing their own plug they were ordered to lower themselves onto their respective mount and 'enjoy' a nice anal fucking.

Michelle was surprised when after she'd gotten over the initial discomfort, and distaste, she began to feel some pleasure from the thing in her ass. Particularly when the vibrations extended to her pussy.

When she took the time to look around, she was amused to see that the others were also deriving some enjoyment out of their ride. Even Wyatt.

The instructors, coaching and encouraging them, explained that guys, through prostate manipulation, could be literally forced to cum, from that stimulation.

"In fact, to add a little fun and motivation to you all, we're going to have a contest. I want all of you to orgasm for us, here and now." Explained the mistress with a cackle. "The one who takes the longest gets three swats on the ass from the crop. The second to the last gets two. The runner-up gets one and the winner gets none."

Again, all of them groaned, but none of them refused or complained, they knew better.

"And, by the way, if we detect any of you trying to fake it, you will be severely punished!" the mistress growled.

Sutton was the first to really begin working it. She began pumping up and down on the dildo in her ass, to add to the vibrations and it seemed to help her along.

Seeing her, Michell began to do the same.

Rather than pump, Gracie reached down with a hand and began twiddling her clit as the thing vibrated within her. Michelle thought that was cheating, so she didn't follow that example.

Wyatt feeling at a distinct disadvantage began shifting his position to get more pressure on his prostate, and when he found the right alignment, he could feel it having the desired effect.

The two trainers stood around watching and cheering them on. But the students didn't seem to appreciate their antics.

Finally, it was Gracie who came first. She moaned, and stiffened, and shuddered to an obvious orgasm.

Surprisingly Wyatt came next, although it wasn't a strong climax, merely a pulsing of cum out from the tip of his cock cage.

Sutton came immediately afterward.

And Michelle was last, several long seconds after Gracie.

Afterwards, they all sat quietly while the vibrators in their asses continued to hum away inside them.

"Gracie is the winner, but I think she cheated, at least in this game. I can't be sure if she came because of her anal stimulation, or if it was because she worked her clit. So, she's disqualified, and will get the three swats. That means that Wyatt, the horny little chastity fucker, is the official winner. See I told you Wyatt men can really enjoy a good ass fucking."

She paused to step over and ruffle his hair. "How did it feel, slave?"

"Not all that good, mistress."

"Better than nothing, though. Right? You did enjoy your ass-fucking, didn't you? And answer me properly."

Wyatt sighed, "Yes mistress, it was better than nothing. I did enjoy my ass-fucking."

Michell could see him blush.

"Good," the mistress said, nodding. "As for you two," she continued, stepping over to stand between Michelle and Sutton. "Nice try, note that you both did get your orgasms from anal sex. Pretty nice, eh?"

When neither of them replied. The mistress got angry. "Sutton, you've had anal sex before, right? It was good, wasn't it?"

"Yes, mistress it was good."

"And slave Michelle? This was your first time. You enjoyed being fucked in the ass, didn't you?"

"Yes, mistress, I enjoyed being fucked in the ass." Michelle responded. She was both embarrassed and surprised to admit it was true. She couldn't deny that she'd climaxed, so she must have enjoyed it.

"Excellent" the head mistress said as she stepped around and turned off all of their Sybians. "Now get off and reinsert your plugs before you stand up. Three of you need to be punished for failure to enjoy yourselves properly."

One-by-one the three miscreants were bent over a stool to receive their swats.

Sutton took her one hit on the ass, stoically.

Michelle groaned on the first one, and cried out on the second. It hurt!

"Michelle, by all rights you deserve another strike for making so much noise," the mistress declared. "I'll let you off, this time, but if you make any noise at all, the next time you're punished, you'll get double. Understand?"

"Yes, mistress. I understand." Michelle replied, subdued. She told her self that there would be no next time. She sure hoped she could keep her promise to herself.

Gracie didn't learn from Michelle's scolding.

She screamed with each strike, and therefore received a fourth, and she wound up crying bitterly afterward. And the Mistress had her stand in a corner with her hands on her head, until she finally stopped.

After that event, it was time to swap their plugs out for larger ones, and that was another chore, especially for those with sore welts on their rears from the whipping.

With the new plugs in place, the trainer put them through a series of calisthenic exercises, in an open area with a wooden floor. Working out on the hard floor, particularly in those positions that required them to sit on their plugs - sit-ups and scrunches, and various Yoga poses, too, was torture!

The four of them constantly felt their assholes being poked and stretched uncomfortably. But it did seem to work. Michell surprisingly found herself getting used to being plugged, and even began to enjoy the feelings - just a little.

Even though it hadn't been two hours, afterwards they were called back into the classroom, and instructed to replace their plugs again, with the next size up.

Accompanied by moans and grunts, they all complied, and just as they were becoming accustomed to their older, smaller plugs, they now found themselves with even larger ones crammed inside their behinds.

They were then taken outside into an open field, for more stretching, and exercising. While there they watched, in the next field over, a number of ponygirls and boys, covered in harnesses, wearing hooves, and with tails sticking out of their asses, being trained. They were prancing and trotting and a couple were even pulling carts. All the while trainers with long pony whips were encouraging them to perform like animals.

Michelle decided that she was happy not to be with them. And she hoped that as she wasn't, her Master wasn't interested in that fetish.

After a while, they broke for lunch, all feeling a little better about their big plugs.

Sitting around the table, on the hard chairs, their asses feeling full, they ate quietly, not enjoying their food, or their seating. They were hungry, though after being so thoroughly emptied by the enemas that morning.

After their meal, at least the food was good, they were introduced to the miserable torture that was the ass-fucking machine.

Four of the things were positioned in the middle of the classroom, and they were strapped in, held on their hands and knees, doggie style.

To make it worse, they were arranged in a circle facing each other. If they lifted their heads and looked across, they could watch the expressions of their fellow slaves.

It was an uncomfortable, bondage position, but at least there were floor pads for their knees.

The terrible part was that the framework included an extension that sat behind them and included a mechanical piston device. When turned on, the thing pushed a rod in and out, and on the end of that rod was a large and long silicone phallus. That big, fat cock was inserted, with a lot of lubricant, into their ass holes.

While they were secured in place on the frame, the mechanism would fuck them in the ass, constantly thrusting in and pulling out, over and over. All they could do was kneel there and take it.

"You need to learn to accept and even enjoy being screwed like this. So, relax, think happy thoughts and get used to anal sex." The head mistress told them before walking out.

The worst part was that they had no idea how long they'd have to endure the screwing.

Of course, Wyatt absolutely hated it, but there was nothing he could do but stew and curse under his beath.

The three girls just did their best to put up with it.

Michelle, resigned after she got over her initial disgust at the situation, actually started to enjoy the feelings, but that only lasted for a short time, before it began to get monotonous and uncomfortable.

When she looked over at Sutton, she wasn't at all surprised to see that the experienced slave actually looked like she was enjoying herself. That girl is a sex maniac, she concluded.

Gracie looked like she was feeling even more wretched than Wyatt. She apparently hated having her ass fucked. Michelle hoped for her sake that her man wasn't into ass fucking.

They never knew how long they were stuck on the machines. But it seemed like hours.

Eventually though the trainer showed up and turned the damned things off pulled the dildos out of their asses and unstrapped them from the framework.

All of them collapsed, moaning onto the floor, stiff and sore, and exhausted.

"Alright, you can rest for a while, but first you have to put in your next larger plugs. Do it now." And he walked around and poked them with his riding crop until they complied. Each of them groaning and crying as they pushed the larger things into their already very sore and well stretched rear ends.

The guy then just left them, lying there on the floor. And there they stayed until an hour later the head mistress, and he returned for the next phase of their training.

They roused the sad crew, and took them over to a corner of the classroom, where on the wall, four big silicone dicks were mounted, sticking out at waist height.

"Alright, this is your final exercise." The mistress announced. And when all four of them sighed, relieved, she scolded them. "Quiet, slaves. Or I might just get the impression that you don't appreciate our little school. And that wouldn't be good for you."

They all shut up.

"You will all remove your plugs, and set them on that table. Then you will lube you ass holes and plug yourselves onto one of the dildos on the wall, bent at the waist, of course. You can rest your hands on your knees for support. Once in place you will fuck yourselves on your dildo. Give it a good ride. A very good ride, until we give you specific permission to stop. This is not a group exercise. The better you, as an individual perform, the sooner we will allow you to stop and call it a day.

"The last one on the wall, will be punished for being lazy. Understand?"

"Yes, Mistress," they all mumbled.

"Good. Get on with it."

Michelle reached behind herself and with considerable difficulty pulled out her plug and placed it on the table. Thank heaven they all had little metal name tags attached to their ends, so she'd be able to identify hers and put it back in when the exercise was over. The thought of winding up with someone else's was sickening.

When she turned toward the wall, Sutton was already backing onto one of the phalluses, but Gracie and Wyatt were still struggling to remove the plugs in their asses.

She stepped over to the one next to Sutton and grabbed a tub of lubricant. She took a big glob out on two fingers and bending over she pushed it into her asshole. She was shocked by how open it was, and how easily her two fingers slid in. Damn! My A-hole so stretched out! She cried to herself.

She applied the rest of the lube onto the dildo and then bent and backed onto the thing. Somehow, it moved up and down on a slide so that it wound up positioned at the right height for her ass.

Once she bottomed out, she looked over at Sutton and saw her pumping the thing in and out by shifting forwards and backwards and forwards again, and she was also shifting her hips side to side as well as twisting slightly, too.

When Michelle followed the other slave's lead, she felt the dildo moving around inside her, and it felt weirdly, excitingly good despite the soreness left behind by the earlier exercises.

I just might be able to get off, on this. She thought, in wonder. But certainly not here and now.

But after a few minutes, her attitude returned to one of dislike and disgust.

Wyatt was the last one to mount the wall, and he only slowly backed onto the big dildo. The mistress grew frustrated with him and stepping in front she pushed on his shoulders, forcing him to take the whole thing in, and causing him to groan, pitifully.

The girls again felt sorry for him. He clearly wasn't into anal sex. Not that they were. Well, Michelle thought, perhaps Sutton was, but no matter.

The instructor continued to browbeat the guy as he began pumping on the thing in his ass.

Eventually, though there was a change in his demeanor.

Noticing, the woman smiled wickedly. "Ah, now you get it don't you, you slut. That thing is feeling good on your silly prostate, isn't it?"

When all he did was pant, and squirm, she slapped him. "You better answer me. Isn't it?"

"Yes mistress," he replied, miserably. But he kept pumping and panting.

She bent down to whisper in hie ear, "good, keep it up. Feel that thing massaging your boy G-spot." Now she sounded more congenial, like she was coaching him - encouraging him. And a few minutes later she stepped back and laughed. The girls still fucking their own asses, looked over to see cum dribbling from his cage.

He had actually climaxed, despite the cage's restriction and the thing up his ass.

"God, I love it when a boy milks himself like that." The mistress said as she continued chuckling.

Poor Wyatt couldn't believe what had just happened. Even his mistress had never milked him like that. It had suddenly begun to feel so good, like the build up with real sex. Even though his cock wasn't involved. But then he felt his cum move inside him, and everything had crashed. The good feelings disappearing as the spunk had just pushed out. It was so mentally and physically disappointing, he actually started to cry.

"Oh, relax you slut. You came, didn't you? With your cage and all, I don't imagine your mistress lets that happen very often. You should be thankful. Now get off that thing."

With shaky knees Wyatt pulled off the wall and stood up, blushing and feeling humiliated.

The staff only gave him a couple of minutes before they ordered the girls to pull off and reinsert their plugs in their tender asses. They all groaned and whined as they pushed the things in past their sphincters.

"Alright slaves. That's the end of your training for today. You will keep those plugs inside you until tomorrow morning. Don't even think about removing them." The mistress ordered.

Giselle, unthinkingly raised her hand for permission to speak.

The mistress sighed before saying "yes?"

"Mistress, but what if we have to relieve ourselves?"

"You shouldn't have to. You need to learn to hold it. But if you feel you must, we'll take you back to the enema station. Do you need an enema?"

"Um. No, Mistress. I'll hold it."

"Good idea." She said, before turning to Wyatt for one last shot.

"Oh, and Wyatt, did that give you a better feel for gay men?" the mistress asked with a chuckle. "Now if your mistress wants, you'll be able to service some guy's big dick to get your rocks off. Won't that be great? You might even enjoy it like you did today."

"Yes, mistress," he mumbled.

"What?"

"Yes, mistress, I'll be able to service some gay guy."

"Very good. That's why you're here, to expand your horizons. Now everyone off to dinner, your day is done."

Gingerly they all sat on the hard benches at their communal table to eat their evening meal. The hard surface pushed their plugs in even further, and they all squirmed unhappily as they ate.

That night, in her cage, Michelle realized that her behind wasn't all that sore any more. It had apparently become used to being stretched by the huge thing jammed in there, and she wondered if her rear hole would ever close. Would it, could it, remain open forever? That was a frightening, and disgusting thought.

She had to admit, though that anal sex wasn't all that bad, but she hoped that her new master wasn't a fan of anal. He, whoever he was, would have full access to her pussy, through her forest of chains, anyway. Why would he need to use her ass. Except perhaps to humiliate her. That's what she always believed anal sex was all about.