Gaming vs. Femboy Ch. 04

Cass finally left the church full of cum, and slightly dizzy. Adora had cleaned him up properly before sending him off, so anyone at a glance wouldn't see what he'd just been up to. His clothes were all free of cum-stains, most importantly.

His tummy however, should anyone be able to see inside it, was cozily full of cum again, and Cass imagined just the slightest outward bulge in it, as though he'd eaten an overly large meal. His femboy body was, it had to be said, quite a bit slimmer than Cass was used to being, so in some ways it was hard to say what his capacity was.

He made his way through the streets of the city, constantly reminded how smol he was as he passed other people, the vast majority of whom were larger than him, sometimes by a ridiculous margin.

Quite a few passers by spared him a glance, often with a bit of a smile to go along with it, or an interested look in their eye. Cass wasn't used to attention like that out in public, and was torn halfway between reveling in it, or shyly trying to cover up. His outfit was quite exposing, after all, with his short skirt and crop top style breastplate. That plus his thigh highs and elbow gloves suggested more confidence in his body than he really had.

It was like he was getting away with something. Like maybe most people around him mistook him for a cute girl rather than a cute boy. And in any case, he was being allowed to appear in public in a much sexier outfit than he could have gotten away with in reality.

Judging by what some of his fellow players were wearing, he actually wasn't alone in that, though. A majority were wearing perfectly serviceable suits of armour, or robes, or sometimes what appeared to be just functional clothing. However there was a noticeable contingent who, like Cass, were wearing skimpier outfits than really seemed appropriate for adventuring purposes. Gauzy dresses, loincloths, partial nudity, and even some actual instances of chainmail bikinis, or the rough equivalent thereof.

The latter outfits, along with the sheer variety in races, colours, hairstyles, and gaudy clothing, made Cass feel a bit more comfortable about how he was presenting to the game world at large. He might be getting more attention than he was used to, but he didn't actually stick out like a sore thumb by any means.

He also appreciated some of the slutty outfits around, and people seemingly entirely happy to show off for those around them. He had to be careful though because he was already pretty horny again, and only the pleats of his skirt stood between him and a very obvious display of his erection. A lack of panties and a fairly large butt plug that made itself known with every step he took really weren't helping anything.

"Cass!"

Cass jumped and nearly lost his balance, only staying upright as a pair of hands steadied him. He continued to panic until realizing the voice and hands both belonged to Vanya.

"Jeez, don't scare me like that," Cass complained.

"Hehe, sorry," Vanya said, without sounding like she meant it even slightly.

She reached down and helped tug Cass's skirt back into place. He probably had briefly been flashing everyone around them, but he didn't want to think about that too hard.

Vanya was wearing a new dress from when Cass had last seen her. It was elegantly sexy on her pink tiefling body, showing off the curves of her form and a good hint of cleavage. It appeared less ready for action than her previous choice, but it might not be meant for that. There was no particular reason one had to only have a single, all-purpose outfit, Cass supposed, despite that being a usual trope of video games.

"Just came to see if you were ready to go shopping," Vanya said. "Since I saw you were online and all, and the group's got nothing planned at the moment."

"Shopping?"

"For new panties."

Cass blushed. "Oh right. You're really not gonna give that pair back that you stole, huh?"

"Nope," Vanya said cheerily.

"Do I want to know what you do with them?"

"Probably not." Vanya took Cass's arm and led him down the street. "Don't worry. I'll buy you lots more to make up for it."

"... are you going to steal them as well?"

"Not all of them, certainly."

"Oh. Good." Cass gave Vanya a curious, sidelong glance. "Are you a total perv or what?"

"Bit of an impolite question," Vanya chided without actually seeming the least bit put off by it. "But to be fair, I do think everyone's a little bit of a perv in here," she said, tapping her chest.

"In your booby?"

"Hehe, see? It's fun."

"I know you meant your heart."

"But it's more fun to say booby. I get it. Or titties. I'm fond of titties."

"Who isn't?" Cass asked absently.

They arrived at a storefront. Cass hesitated a moment, but Vanya kept pulling him onward and into the shop.

There were a few people inside the spacious store--a larger area inside than it had appeared from outside, as per game logic--some of whom appeared to be browsing clothing in a normal manner, and some who were standing totally unmoving, and presumably were simply browsing menus judging by how one customer in particular kept switching outfits every few seconds.

"The tailor here is really good," Vanya said. "They're an NPC, so there's a limit to customization, but still."

"A tailor?" Cass asked. "Don't clothes just fit?"

"Technically yes. But they can fit better than default settings, trust me."

"Um... ok."

Cass stood nervously near to the back counter of the shop while Vanya summoned the tailor. A kindly looking older man stepped out, looking like the stereotypical classic tailor, complete with measuring tape around his shoulders and pins sticking out of his mouth.

"Underwear, eh?" the man said. "Well, let's see what we're working with then."

Vanya turned expectantly toward Cass. "He means the skirt needs to go."

Cass nodded. "I thought he might. But, uh...."

"Hehe, of course, not your type, huh?"

Vanya turned back to the tailor, moved her hand around, then nodded in satisfaction as the older man turned into a woman. The tailor now had a sexy librarian vibe to her, with glasses and her hair pinned back, as well as just the slightest hint of no-nonsense severity about her.

"There you go," Vanya said, still smirking a bit.

"That's great," Cass said. "But isn't there like a back room or something?"

"Why?"

Cass looked around at the other shoppers. "You know, because of privacy and such?"

"Oh. Well--"

The tailor made Vanya's answer moot when she simply knelt down in front of Cass and yanked down his skirt. She started taking measurements while Cass was frozen and uncertain what to do next. Showing off his penis, ass, and butt plug to every other person in the store was exactly what Cass had been trying to avoid.

"Oh god, is everyone staring?" he hissed to Vanya, desperately trying not to look around the room.

"No," Vanya said.

"Really?"

"Yeah." Vanya pointed her finger. "That guy hasn't noticed yet."

"Goddammit, Vanya."

Vanya beamed, showing off the pointed teeth in her mouth which could have been considered threatening, but on her just made her seem happy and a bit goofy. "Don't be shy. You look good."

"Not the point." Cass hesitated. "But I do, though, don't I?"

"Mmhm!"

"That's still so weird to me."

"Well get used to it baby boi."

The tailor was impassively carrying on her task of taking measurements, which involved quite a bit of touching. Some of it made Cass twitch or jump a little, and the woman kneeling before him kept gently but firmly yanking him back into place and making tsking noises.

"I shall need sir to stay still, please," the tailor said.

"I'm trying," Cass said, blushing as his balls were handled in the most coldly calculating way they ever had been.

"And if sir could not have an erection for a few moments, I could take the measurements for when sir is soft as well."

"That's a good idea," Vanya said. "Want to know what the capacity of the panties either way is going to be. They'll need to, aheh, stretch a bit sometimes."

"Very funny," Cass said. "Vanya, you know I can't just stop being hard on a whim."

"Well not with that attitude, certainly."

A redheaded and freckled girl slipped up next to Vanya and gave her a gentle nudge.

"Hey, Vanya."

"Oh, hey, Molly. I didn't see you there. You shopping too?"

"I was, yes. Who's your, uh, friend?" Molly asked.

"Cute, isn't he?" Vanya said gleefully. "This is Cass, he's new to the game. I'm helping him buy new undies, since he lost his."

"You literally stole them from me," Cass grumbled, unsure what to do about the new girl standing so close and clearly checking him out.

Vanya waved her hand airily. "Details."

Molly bit her lip and hugged her arms around herself a bit shyly. "So you probably need to be soft for measuring though, huh?"

Cass blushed. "I believe so."

"... want some help with that?"

Cass looked from Molly to Vanya, who just smiled and nodded encouragement.

"Really?" Cass asked. "I'm... I'm a total stranger."

"You know Vanya," Molly said, blushing too and turned her head away slightly. "And she's cool."

"I am," Vanya agreed seriously. "Also Molly kinda likes blowjobs, but she's kinda shy usually and--"

"Vanya!" Molly said. "Shush!"

"But you do like to give blowjobs," Vanya said.

"You don't need to tell people that!"

"You literally just came over and asked Cass if you could help with his erection," Vanya said. "Why is this my fault now?"

"It's... you're not...."

The tailor knelt on the floor adjusted her glasses while Vanya and Molly bickered. "If sir could accept a blowjob, it would make the measuring easier," she said.

"Yeah, that... I know that," Cass said. "I'm not totally sure what's happening though."

"There's nothing wrong with practicing the occasional blowjob," Molly said, clearly quite flustered by now. "It's pretty consequence free in game."

"And you liiike doing it," Vanya teased.

"Shush I said!"

"And you think Cass is super cuuute."

"Oh my god, Vanya," Cass said, putting a hand over his face.

"He... he kind of is," Molly said. "And I just mean 'cause, like, cute boys are less intimidating sometimes."

"Mmhm. I'm sure that's all it is," Vanya said. She tapped Cass on the head. "What about it, Cassie, want a nice li'l blowjob?"

Cass shyly glanced at Vanya, at Molly, at the tailor, then at the room at large. He would have preferred privacy, but there was a certain excitement and pleasant feeling about a cute girl he didn't even know being interested in him this way, even if her motives were not the clearest at the moment.

"I could probably go for one," Cass mumbled. "If it's being offered anyway."

He was already bottomless, erect, and plugged. It wasn't like things were going to get more embarrassing for him.

The sight of a cute girl--a perfect stranger no less--sinking to her knees in front of him was really, really nice, Cass had to admit. The way she looked up at him with her shy, nervous enthusiasm provided a feedback loop with his own very similar emotions.

Molly was so tentative about touching his cock with her fingers, and let out a soft giggle as it twitched in her hand. She seemed genuinely entranced by Cass's erection, and just kind of played with it for a bit before apparently remembering what she was supposed to be doing.

For some reason, Molly got a lot more confident as soon as she got Cass's cock in her mouth. There was no playing around anymore, and she took him fully inside, savouring the process just for a second or two before bobbing back and forth on him. She made some small moaning noises that soon became mixed with sloppy blowjob sounds as an accumulation of spit and precum built up.

Cass rocked a little unsteadily at the eager assault on his cock, finding that he could have used something to brace himself on. Unlike Adora's calm, professional, and effective technique, Molly was far more forceful and undisciplined about sucking him off.

Vanya hummed to herself while hopping on a nearby counter, then carefully flipped back the skirt of her dress and started playing with herself while watching.

"Seriously?" Cass asked.

"What? It's hot," Vanya said. "Very public, you know."

"I-- what? Of course I know. I was the one who wanted privacy."

Vanya shrugged. "Well that didn't really work out for you, huh?"

"You're enjoying this, aren't you?"

Vanya stuck her tongue out playfully and rubbed her pussy a little faster. "What gave it away?"

Cass shook his head at Vanya's wantonness, but also secretly enjoyed being able to watch her masturbate. She was fun and hot, and maybe just a bit slutty, and she seemed to like him. Cass wasn't used to girls like that hanging around him, let alone openly masturbating as well.

Molly was still slurping away on him too, and when Cass looked down at her he realized she was occasionally staring up at him with big puppy eyes like she was waiting for something from him. His cum, presumably.

Cass assayed a couple headpats, in case Molly was seeking some encouraging feedback in the meantime. She responded well to them, moaning happily and choking herself harder on Cass's cock.

He groaned and came in her mouth, spurting hot cum all over her tongue. She whimpered and swallowed quickly, still losing some in the process and making a small mess down her chin.

Molly seemed quite pleased with herself as she sat back on her heels, still looking up at Cass. She swiped at her chin with the back of her arm to wipe away the traces of cum she'd missed. Cass thought she looked even cuter now, despite panting and being somewhat flushed in the cheeks, though fresh off getting a blowjob from her he was probably biased.

"Much better, sir," the tailor said. "I shall be able to proceed now."

The efficient woman carried on taking measurements around Cass's now flaccid penis as though nothing out of the ordinary had occurred. It was a slight emotional whiplash for Cass transitioning back to her professional, uninvolved touch, though there was still something alluring about being handled so intimately by someone who didn't seem the least bit interested in him beyond his physical dimensions.

Perhaps it was the fact that he was still half-naked in a fairly public area. That might well have leant some interesting lack of professionalism to the affair. Vanya was still rubbing herself, and a quick look about confirmed that Cass himself still had a bit of an audience, even if he wasn't the centre of a room full of staring faces, as he'd somewhat feared.

"That was kind of fun," Molly said, rising to her feet.

"Hehe, yeah," Vanya said. "Cass is a fun boi."

"You just gonna keep masturbating or what?"

"Planning on it. We're gonna get to see Cass in panties now."

Molly only hesitated for a second before hopping up on the counter to take a seat with Vanya. "Sold!"

Cass rolled his eyes, but didn't have time to get particularly exasperated with the girls before the tailor was slipping a pair of underwear up his legs. She was scarily good at maneuvering him just so without him really being aware how she was pulling it off.

"These are just a very basic model," the tailor said. "You--"

"Boo, no," Vanya said. "Something sexy, por favor."

"Very good, ma'am."

Cass found himself modeling a variety of cute and sexy panties for Vanya and Molly, who unabashedly played with themselves the whole time. Once again in this game, he found himself in a weird position of being quite embarrassed, but excited enough to counteract the feelings of shame and inappropriateness. The sense of pleasure that came from being physically desirable in a way that he hadn't really experienced in real life was nice too. Like being one of those hot girls who could command a room just by existing, only doing it as a boy. Mostly.

"Unf, those shape your butt so good," Vanya said.

"Definitely. Get those," Molly agreed.

"Um... ok, but the last pair were super comfy," Cass said. "And I think--"

"So get both," Vanya said. "I'm paying. We'll get as many pairs as you need. I owe you."

"Oh, so nothing to do with wanting to keep watching me try panties on?" Cass asked.

"Maybe a smidgeon," Vanya admitted cheekily. "How about something really high cut next?"

Molly nodded her agreement while continuing to finger herself.

Cass acted mildly annoyed with their insistence, but was getting more and more into this. He kept surprising himself at how every sexy move he tried while showing off the underwear kept getting pleased reactions from the girls. How showing off his ass in scanty panties really seemed to turn them on. He could seriously get addicted to being a cute femboy at this rate, and having a butt that could hypnotize a room with a calculated pose.

Another interesting thing was how well the panties fit when Cass started getting hard again. Showing off so lewdly, butt plug still included, made an erection basically inevitable. Those previous measurements appeared to be paying off, as every pair of panties seemed perfectly designed to sit flatteringly on his body, whether he was hard or soft.

Vanya and Molly smiled wider every time he modeled a new pair with a prominent tent sticking out at them. Sometimes his cock was basically unrestrained and stretched the material straight out from his body, sometimes the panties snuggled his penis more tactically while still very clearly leaving a bulge visible. Cass suspected he'd want something more the latter when trying to be discreet, particularly when his skirt left him somewhat exposed even at the best of times.

"Ooh, hell with it," Vanya moaned. "We'll buy every pair. Might as well have options."

"Good choice," Molly panted.

Both girls were getting very close, Cass could tell. They were frantically rubbing their pussies and whimpering with need. Rather boldly, he turned away and slowly, sexily pulled down the panties he was wearing, making a show of gradually exposing his ass and butt plug to them. He bent over at the waist, keeping his legs straight as he took the underwear all the way down to his ankles and daintily stepped out of them.

As he'd hoped, and as was bizarrely satisfying to him, he made both girls cum just by being naughty and provocative. When he turned around, it was just in time to catch Vanya squirting wantonly onto the floor. Without thinking about it, Cass dived between her legs and latched his mouth to her pussy. If his spells were all powered by cum now, maybe hers would count the same as cum from cocks.

"Ooh, good boy," Vanya cooed, patting Cass's head.

He blushed and kept sucking the last of her juices, enjoying his lips on her soft, very warm skin, as well as the taste of her. He had to quickly move to Molly though as she started squirting too, and he caught even more of her cum in his mouth. He didn't dare look up at her, as technically sucking on a near-stranger's pussy without asking was probably a bit of a consent faux pas. The cute redhead didn't seem to mind one bit, luckily enough.

The girls' cum did seem to add to the liquid supply of power in Cass's tummy, as far as he was able to sense that kind of thing.

He got more headpats from the girls, and really leaned into them. It was like getting double or triple rewarded for every sexual act, between the horniness, power ups, and physical affection.

Vanya and Molly got themselves sorted out and presentable again. Cass tried to do the same, but was denied as he tried to slip on one of the more comfy pairs of panties Vanya was buying for him.

"No no no, not that pair," Vanya said. "These ones."

"But those ones are way too skimpy for adventuring and are gonna show off too much if my skirt flips up in any...." Cass paused. "That's exactly the point, isn't it?"

"Maaayyybe."

"I second that pair," Molly added unhelpfully.