Virtuous Thief

Naomi led Morgan into a basement parlor and gestured him behind some modesty curtains. As she had him undress fully, she turned away and slid out of her sundress before gathering up her measurement tools. Morgan had spent enough time in the public baths of the church to not be embarrassed by stripping down, even in front of a strange woman, but there was still an amount of reservation as he shed his way down to just his chastity cage and stood on a raised dais.

"I hope you bathed well before this, because if I'm smelling you the whole time and you reek, I might just spritz you with flea bath and let you sit for an hour or two before I come back."

Morgan sniffed himself self-consciously before Naomi turned around with her needles and tape measures. She looked him up and down before whistling.

"Geez kid, those street clothes did you no favors." She circled him casually, "I had hips and a waist like that, I might be in a different line of work."

"The church put a great emphasis on exercises of the lower body," Morgan explained professionally.

"Guess I gotta get religious." The scrawny elf whistled, "That explains the johnny lockup too."

"Yes..." Morgan felt a slight flush of shame he didn't expect, "I'm hoping to make enough money to buy a replacement key or get an artificer to remove it. The owner of my contract destroyed the only means of removing it."

"That's too bad," She prodded his cage once disinterestedly, "Though you seem like you got off light. Some of the church people had devices like whole belts or sets of undergarments."

"Yes," Morgan replied, "Those were for acolytes who especially struggled with libidinal urges."

"And you didn't?" Naomi asked with a hint of teasing.

"I did, just not very badly, not in the way of trying to stuff things inside of myself."

"Oh," Naomi tittered, "I see. You might regret that."

"Why would I?"

She pinched his ass, "A thief's back pocket can be their best friend. I'm not saying you need to be able to hide a whole crown up there, but being able to store a couple of jewels..."

"Doesn't that... hurt?" Morgan could stop from blushing slightly.

"Not with the proper training and preparation. For some people, it's even more fun than the other stuff. Even leaving aside all the other applications." Naomi made it sound like the most normal thing in the world.

"Is it really that common to do that?"

"Oh sure. Depends on the job of course. Certain magical scanners can penetrate burlap but not muscle. You can strip down and not reveal what you've got. Girls obviously have a second compartment, but even for them, it's not usually as spacious as even a decently-trained ass can be."

Morgan made quiet note of Naomi's seeming attempt to distance herself from being a girl but said nothing. She started measuring him casually, moving his body without a care of where her hands touched.

"So, why a thief?" She asked plainly. "I mean, you're not built like a warrior, but..."

"I suppose I've always been very good at it." Morgan answered honestly, "Almost magically so."

"And what makes you a good thief? It can't be fitting in and out of vents."

"I have this sort of gift..." Morgan started to answer honestly but decided to hold back somewhat. "I've always known what others are thinking. Not true mind reading, more sort of the shape of their thoughts."

"I thought I felt you poking around earlier," She sounded nonplussed, almost bored, "What did you see from me?"

"Nothing really. I didn't have long enough, plus it isn't really telepathy." He lied slightly, "It's not like if somebody has a lockbox, I know where the key is and what's inside. It's more that I can tell which drawers they'd prefer I don't check, what kind of things they're worried about losing."

"Sounds handy for a thief," She made a note on a small handbook and then folded it closed. She looked him in the eye with an almost uncomfortable scrutiny. "So what sort of shape do you get from me?"

Morgan reached out and immediately blushed a little deeper, "You're just thinking about my ass."

"Damn right I am," She made another note in her book, "Seems like it's pretty easy to trick."

"Yes," Morgan admitted, "But nobody other than you and my chapter mother have ever purposefully tried to trick it."

"Seems like if anybody is feeling any one thing intensely enough, it isn't very useful."

"Right, but most people aren't feeling anything very strongly at any given moment."

"Fair enough," She tucked the notebook into her waistband, "I guess if I just keep thinking about your ass, I don't have to worry about you finding all the gems I have hidden in this room."

"I wouldn't steal them anyway, Gordy said not to mess with the other people in the guild."

"Correction," She wrapped the measuring tape around his hips, "He said not to fuck with the other people in the guild."

"Sure," Morgan gulped as Naomi's hand brushed his caged cock, "He probably phrased it more like that."

"Goddess bless him but I think he might be more anxiety than man at this point. I don't know how his stomach hasn't fallen right out of his body from worry."

"Is he..." Morgan tried to find the right way to phrase it, "Do any of the guild members actually want to..."

"Are you kidding? Not in a million years. He's got his rough edges but nobody to hold the chair has done it better and there's a chance nobody ever will. Even ignoring that, why would you ever risk being the person who gets appointed as his replacement?"

Morgan offered a weak "ah" in response as Naomi finished measuring his legs and butt before pinching his ass again and making a few final notes in her book.

"So, your suit is going to be fairly easy to make. We basically just need to take a female fit and pad out the crotch for your cage while tightening the chest."

"I see," Morgan replied plainly. Naomi gave him a look like she had expected him to be embarrassed by this or take offense to it, but female-fitted clothes had become the norm for him a while ago. And the teasing for being as bottom-heavy as he was had ended shortly after it began.

"You have a very androgynous body for the most part, not sure if anybody has ever told you that. You ever think about cutting your hair or not shaving your beard if you want to look more manly?"

Morgan fingered his cheek-length ginger hair nervously, "I've never shaved before."

"Not anywhere?"

"No?"

"And now I'm jealous about two things," Naomi sighed.

"It's not like I don't have hair, it just comes in so light..." Morgan picked at the wispy pale hairs on his stomach to demonstrate, but it didn't seem to do anything to convince Naomi.

"You must have been popular at your church."

"We all took the same vow of chastity, if that's what you're implying." He sounded a little more indignant than he'd meant to.

"Yeah yeah," Naomi went over to one of her cabinets and fished out a box full of metal balls of varying sizes.

"Are we done measuring?" Morgan gestured at his clothing sitting on the ground.

"I mean, technically, we are." Naomi shrugged, "But Gordy is probably going to put you on the artificer job, so it might be best if we get you used to using your rear pocket."

Morgan suddenly flushed intensely, "What makes you say that?"

"You wanna make money fast right?" Naomi also pulled a tall phial of something clear from the cabinet. "The artificer is almost blind and completely feeble, so he should be a pushover, and the payout is potentially huge."

"If the payout is potentially so big, why send a newbie?"

"Think of it like this. If you fail, the artificer might make you sweep the floors or try out one of his new devices, but he's a partner of ours so he won't kill you or report you. The fail state is that you don't come back with any money. The potential payout is huge, but even coming back with anything is a win. So the boss is gonna judge you based on how much you can come back with."

"Wait, we're stealing from our partners?"

Naomi looked at him incredulously, "Didn't Gordy give you the whole speech? We're a guild, buddy. Nobody gets mad at us, especially if we're on good terms, it's all about the people hiring us. Now are you going to do this or are you going to keep asking obvious questions."

"Okay, just..." Morgan realized that he was nervously stalling for time to a certain extent, "One more question, how do we know that the "back pocket" is the key to a good payout here?"

"That's a good question, actually." Naomi put her hands on her hips, "Even though the boss will probably explain this better. If you're stealing from an artificer, you're going to be stealing magical artifacts. That thing I said about scanners going through a burlap sack but not muscles? That wasn't an accident."

"And these artifacts are going..."

"Okay, don't tell the boss I told you this, but we've been sitting on this request for a bit and I know more about it than I'm supposed to." Naomi looked around conspiratorially, "The stuff you're stealing is a bunch of magical orbs he's been hoarding. You can probably fit one in each fist or your mouth to get it past the scanners, but any more than that, any amount that gives a real payout?"

"I see," Morgan winced, "What are they like?"

"Perfectly smooth and harmless," Naomi said reassuringly as she fished in the box and pulled out two balls, one about the size of a big toe, the other slightly larger around than a clenched fist. "They're magical storage stones, so they might tickle but that's it. Largest one we know of is about the size of this bigger one."

"There's no way..." Morgan gulped as he looked at it, but Naomi chuckled.

"At least check and see before you claim you know for sure."

Morgan assented nervously and Naomi gestured for him to bend over a table near the dais and spread his legs. He craned his neck to watch her anxiously as she grabbed both the tall phial and the box and set them down behind him. Kneeling between his legs, she spread his ass gently and poked his hole softly with one finger. It was the first time anybody but him had ever touched back there or below the belt. He waited for her to start trying to force her finger in, but she circled his ring and then flicked her finger against his balls before dipping it into the tall phial. It came out covered in thick, oozing slime which she brought back up to his back door and started to rub in gently. It was wet and slick, and it made the skin where she left it tingle slightly. Morgan found his breaths to be coming a little faster than before, the sensation neither good nor bad so much as... strange and stimulating.

Naomi very gently pushed her finger against his hole and it slid in almost without even being noticeable. It was so slick with slime and so soft and slow that Morgan only noticed it was even in when she began to flex and turn it, rubbing against the inside walls of his ass tenderly. There was no pain, and in a moment he understood why so many of his brothers in the order had potentially risked punishment doing things like this. Though the idea of something larger and less gentle than Naomi's finger still seemed unpleasant and unrealistic. As her fingers moved, they stroked over a particularly sensitive spot inside of him that made Morgan jump slightly and made his cock twitch inside of his cage.

"Ah, there it is."

"There's what?" He asked with a shaky voice.

"Boys have a little pleasure spot inside of them right here, called a prostate," She rubbed her finger back and forth across it as a demonstration, "That's what makes using the back door feel good to them."

"It's... strange..." Morgan whimpered honestly.

"You'll get used to it." She pulled her finger back out and then prodded a pair of them against his back door, "And the more used to it you get, the better it will feel. Some boys can even cum just from having it played with, or from having something hitting it during sex."

"Even in a cage?"

"Even in a cage," Naomi's voice was a little shaky itself.

Two fingers was a lot more noticeable, though it still wasn't anywhere close to painful. The feeling of being spread open was a very different one to just being penetrated, and it made his whole lower body tighten down like it was trying to force Naomi's fingers out of him, even as the pair circled and found his prostate again.

"Relax, take a deep breath, try to unclench your muscles," Naomi sounded like she was getting winded, "If you tighten up so much, it might hurt."

Morgan let his head hang down and tried to relax his entire body, feeling Naomi slip another finger in as he did. Now with three fingers, it was starting to feel more uncomfortable, like he was trying to take something that was actually too large. But as he continued to breathe deeply, it slowly got easier. Naomi's breath was only getting faster. He glanced at her under the table and saw that she was rubbing and stroking the outline of a bulge in her leather catsuit crotch. Morgan cleared his throat meekly and looked away. A second later, Naomi withdrew her fingers and cleared her own throat.

"Now that you're warmed up, let's start with the objects." She said breathily.

"S-sure," Morgan agreed.

A thin, wet trail was dripping from the head of his cock like he'd been having dirty dreams, and he was painfully aware of his inability to touch himself in the kind of way that he experienced only rarely. He was so used to his cage that he often forgot it was even there, what it was like to really strain against it, and why he wanted it removed.

Naomi fed the smallest of a set of twelve balls into his ass almost without any resistance. It sat inside of him dully, neither pleasant nor unpleasant, just a lump that wouldn't go away.

"Good... very good... You may want to push it out, but hold it inside until you have all of them and you've walked around a bit..."

Morgan made a noise of soft agreement and Naomi started feeding the second ball into him. He felt it more, but it still went in with very little resistance and joined the other lump inside of him. He heard leather shifting and Naomi politely coughed to try to cover it. As she was feeding the third ball into him, he glanced back between his legs and could see that she had let her cock out of her pants and was stroking it softly with her free hand.

"You're doing good... don't tense up..." She mumbled as she jerked herself slowly.

The third ball popped inside of him, large enough to be more noticeable and intense, but still not unpleasant. More and more it felt like his back door was slowly being stuffed with stuff, like he was using it as an actual back pocket. Naomi's cock was a dark olive length with a dark brown head which had already started drooling at the tip. It was hard for Morgan to be sure if she was bigger or smaller than normal, having only ever seen caged cocks since reaching adulthood, her hand wrapped completely around it and covered the length of it in quick little strokes. Either way, while he was still caged, it was bigger than his. All that really mattered was that the way stroking it made Naomi pant and shiver just made him wish he could play with himself more and more.

Naomi's fourth and fifth ball went in one after the other almost without him noticing. Even if it didn't hurt, Morgan was starting to feel stuffed enough that he was certain his stomach would be swelling or something like that, but when he looked back, nothing of the sort was happening. The idea that he wasn't even half way was astounding, but the fact that it still didn't hurt was most surprising of all.

"That's... impressive..." Naomi panted, "I didn't think you'd get six... let alone all twelve... Are you sure it doesn't hurt...?"

"N-not really," Morgan was struggling with his words, the feeling of being stuffed was so intense.

"And you swear... you've never done anything with your ass before?"

"N-never..."

Naomi muttered to herself and pushed the sixth ball in without the easing and fanfare the previous ones had gotten. It pinched slightly, and it only made his guts feel heavier, but Morgan gritted his teeth and let it happen.

"Just... even I couldn't do all twelve with practice... so let me know when you want to stop and we'll stop."

Morgan started to respond, but yelped as Naomi stuffed the seventh ball in forcefully, then the eighth before he even had a chance to recover. His guts were turning at the feeling of being so clogged and full, but there was something headily intoxicating about the feeling. His knees tried to knock together as he felt more and more precum leaking slowly from the inside of his cage, cock straining desperately against it. Naomi let out a soft noise between a giggle and a moan as she started feeding another ball in.

This one stretched his asshole wider even than three fingers had, and Morgan was certain it wouldn't go in as it slowly split him open more and more. The moment of passing the widest point was a brief second of intense bliss as his body sucked the rest of it inside of him and it came to rest with the others heavily in his guts. Morgan grumbled without forming real words, his brain feeling almost scrambled by the aching soreness of his ass and the giant mass of metal stuffing his guts. He let out a slightly girly squeak as Naomi leaned forward and kissed his balls.

"Home stretch rookie... do you think you can take it? I don't think you can..."

"I... I can..." Morgan mumbled.

"O...kay..." Naomi hummed, pressing another orb against his ass.

It slowly stretched him out to three fingers width and then kept going. For the first time, Morgan could really feel the stretch of the toys as if they were pushing him to the absolute limit, but he gripped the edge of the table and forced his lower half to relax as much as possible until the ball finally slipped in and he let out a whining whimper. There was a strange, intense sensation building between his legs as the metal shifted and moved inside of him, trying to find the arrangement that relieved the pressure it was putting on him. His cock was leaking a stream through the tip of his cage, but it felt like there was even yet more to come. As Naomi pressed the penultimate ball against his ass, Morgan almost without noticing started to push backward towards her hand, forcing the largest ball yet inside of himself with relative ease.

"Shit," Naomi was breathing like she might cum at any second and she took her hands away from her cock to cover the final, fist-sized ball with oil, "Last one, are you gonna back out now?"

Morgan groaned and wiggled his ass toward her suggestively. She took a deep breath and started to press it into him. Morgan almost balked at the size of it, finally feeling a shred of overwhelming discomfort as it spread him wider than he thought possible for a human, let alone himself. Even pushing back into her, relaxing his body, it didn't help. Nothing he did made the feeling less intense or less scarily overwhelming. And then, right at the very second he was certain it was impossible and he would need to beg Naomi to stop, his ass closed around it with a pop and it lodged inside of him like a massive cork holding all of the other balls in. Morgan let out a groan like a contented pig. All he could think about was the massive metal load in his ass and stomach, pressing against his prostate and shifting inside of him.

"Oh my goddess," Naomi breathed, kissing his asshole tenderly, "I didn't think it was possible."

Morgan tried to straighten and stand up but his knees nearly gave in. Naomi helped him stand, not even trying to hide her dribbling, twitching erection. The first few steps were almost doubled over, trying to handle the feeling of the massive weight inside of him and how it shifted constantly, but after a few moments of adjusting, Morgan could walk from one end of the room to the other without issue. He could almost think straight again too.