Gaming vs. Femboy Ch. 06

Some more fighting carried on around them as Ash continued directing their other units. Cass appreciated that the rest of their army was being used as fodder so that he and Vanya could get by relatively unscathed. Even though the next couple fights he got in used up his cum reserves so that he could destroy opponents before they got to damage his squishy body, it was still going fairly well overall.

Cass almost started to feel good about their chances of winning soon, both armies were thinning out pretty nicely and he and Vanya remained in good shape, but some elite units were still in play. One of said units engaged Vanya, and while Cass was distracted, another sneaked up on him and started combat while he wasn't even ready.

"Aw heck no," Cass said, trying to back away but running into an invisible wall. "I do not have the capacity to deal with another fight right now. Ash? Ash, I cannot fight someone right now. I'm spent, and you know it. Vanya? Anyone?"

The woman approaching was only wearing partial armour, the sort that really wouldn't cover anyone in real combat--and incidentally regarded modesty as an afterthought at best--but in games indicated an elite status. She grinned as she approached, showing off razor sharp teeth and a decided proclivity toward the ferocious and vicious.

Cass in his flimsy armour, if one could even call it that, did not like his chances. He'd burnt up his power supply, had no more cum to drink, and was not built for a fair fight in any capacity.

"Ash?" Cass called, trying vainly to back away from the scary lady. "Assshhh?"

He bumped into an invisible wall that surrounded the individual conflict, preventing him from leaving until the battle had been sorted one way or another. It was very unhelpful at the moment.

"Ash you have a plan for this, yes?"

"Give me a minute," Vanya called from nearby, betwixt the sounds of clanging metal and zapping lightning bolts. "I can help once I take care of this guy. Who should be dead already, thank you very much!"

Cass suspected the latter part of her offer was meant for her opponent rather than him. Vanya did get a bit annoyed when her grand magical powers came off less effective than she felt they should. Which was fair enough really. Much like himself, when magic didn't work there wasn't much else to fall back on.

Something wrapped around Cass's wrist. He blinked slowly, unsure what was happening at first. Another tendril took hold of his opposite wrist. Cass visually followed them back to his opponent, just in time to watch more tentacles sprout from behind her and sinuously lunge for him.

"Ohhh," he said, giving a sigh of relief as he was wrapped from various angles, decreasing his mobility down to nearly nothing. "She's a tentacle monster. Phew."

"You ok?" Ash called. "Sorry, I was busy with something."

"No, all good," Cass called back. "I thought she was gonna fight me, but it's ok, she's just gonna fuck me."

"She can probably do both," Ash said. "I can send reinforcements in a moment if you just--"

"Don't worry about me," Cass said, even as his very short skirt got shredded in a casual move from a couple tentacles. "I thought I was about to get pummeled. This is much more manageable."

"You might still get pummeled," Ash advised.

"Well yeah, but in a sexy way though," Cass said as his panties suffered the same fate at his skirt. He probably should have undressed, but it was kind of hot getting his things torn off like that, and it wasn't like he was short on sugar mommies to buy him new and even more scandalous clothing if need be.

He did pop his breastplate back in his inventory, since he didn't really want to find out what happened when someone tried to forcibly remove it. He was soon left with nothing at all on other than his thigh highs, which felt very deliberate on his captor's part. It did make for a sexier look, after all, if that was part of the objective here.

"So hey, are you an NPC enemy?" Cass asked the tentacle woman. "Or are you actually another player? Because this feels like something a person would do to me."

There was no response from the woman, at least not vocally or regarding her facial expression. Her tentacles were doing all the work, dancing over Cass's nearly naked body, making sure he was pinned tight and just kind of playing with him.

He was surprised at how nice these touches were feeling. These tentacles were so much softer than the last time he'd been tentacle-fucked, and so much more tender in their caresses of his smol body. Which was kind of weird, considering this was supposed to be a combat scenario, but he wasn't about to complain if some tentacle-maiden wanted to treat him to satin-soft embraces.

Cass's tummy tingled as it experienced sensuous tentacle touches, followed by the sensation traveling to his nipples. He gasped lightly as he discovered a subtle suction action, essentially having his nipples sucked on by the ends of certain tendrils.

Cass bit his lip and tried not to be too obvious about making horny eyes at his captor. She was busy studying his body more so than his face at the moment, but that could change.

Some other tentacles were probing around his bum all the while. His butt plug protected his asshole for the moment, but they appeared to be working on that. Two or more tentacles felt like they were working together, playing with the plug in his bum which actually felt quite nice, before one of them managed to wrap itself around the flared base and give it an actual tug.

Cass purred as his plug was gently pulled out a little, then let back in. He was teased that way multiple times, stretching his booty a bit more each attempt until his plug popped free. He missed the feel of it in him almost immediately, but he had other distractions to occupy him. Lots of other distractions, in fact.

A tendril was writhing its way up Cass's shoulders and neck, and was soon twitching back and forth, just barely brushing his lips. He strongly suspected he knew where it was headed, and very nearly tried catching it in his mouth. His group did accuse him of being a slutty little thing sometimes. He wouldn't give in to the title easily, but there were times when he knew it to be absolutely true.

For instance, being restrained the way he was, totally and lewdly exposed, and rather than fighting it was instead seriously contemplating how to get a cock in his mouth. Or the tentacular equivalent thereof, at any rate.

The tentacle slipped in his mouth with surprising deftness once the woman decided to go for it. One second it was still teasing, the next it was halfway down his throat, seemingly ignoring all resistance on its way. Cass choked in surprise and tried to cough, but it didn't work very well. Mostly he just drooled over himself.

"You alright there Cassie?" Vanya called over to him.

Cass rolled his eyes. She would wait until his mouth was full.

Grumbling internally and trying to focus despite the invasion of his mouth and throat, and indeed the tendril now teasing his butthole, Cass worked his menus to bring up his communication HUD.

"Fine, thanks," Cass replied, feeling the odd disconnect of being able to speak while simultaneously still being orally stuff.

"What's going on?" Vanya asked, peering at him intently from a small box to the side of his vision. "Why did you pop comms? Oh. Ohhh. Got something in your mouth, huh?"

"Yeah, kinda do."

"Hehe, I can't take my eyes off you for a moment, can I?"

"Don't worry about me," Cass said. "I can--"

"Oh I wasn't worried," Vanya said airily. "Just think it's funny how quick a cock finds its way into you sometimes."

"Rude."

"True."

"Anyway, as I was saying. If I can get this woman to cum in me a bunch, that refuels me for the rest of the fight."

Vanya nodded seriously. "Good thinking. You think she will?"

"She's about stomach deep in my mouth currently and probably going to pop into my butt any second now," Cass said. "So looking good. And... oh. Oh wow. One of her tentacles is sucking on my cock somehow. That actually feels amazing."

"Pff, lucky," Vanya pouted. "All I got to do was fry a bitch. How come no one's tried to tentacle-fuck me?"

"Just not quite as cute as me, I guess," Cass teased.

"Now who's rude? Maybe I'll just leave you there to your fate, hm? How 'bout that?"

Any cunning retort Cass could have made was cut off by the feel of a large, soft, sinuous cock plunging up his butt, lubricating its own way as it went. It was a curious feeling, as the squirmy tentacle could produce sensations ordinary cocks couldn't, really quite nice ones, and did a lovely job filling his ass as it probed deeper.

"Cass? Cass, you listening?" Vanya sighed. "Oh heck, lost ya for a while, huh?"

"I'm here," Cass answered faintly. "She's up my butt now. It's... damn it's good, actually. I think she's about to meet the one coming down my throat the other way by the feel of it."

"Fuck. Hot."

"Are you... playing with yourself?" Cass asked.

"No."

"Why are you moving weird?"

"No reason."

Cass was able to move his head just enough to catch Vanya in his eyeline, getting a fuller view of her than he got from his communication HUD. She was sitting cross-legged and most definitely had a hand up under her dress.

"You're a liar," he said.

"Well if you'd stop getting fucked all the time I wouldn't have to masturbate to you so often," Vanya said. "So really this is your fault."

"Wait, you masturbate to me a lot?"

"... no."

Cass felt himself blushing, realizing even as it happened that it was weird to blush at the masturbation thing and not the very public tentacle-pounding currently being inflicted upon his delicate body.

The tentacles inside him had definitely passed each other inside him, though they were nimble enough to not get stuck on each other. They were going back and forth in a very erotic rhythm, fucking him from both ends while his cock got suctioned on and his nipples were toyed with. It was a lot all at once, but in the best possible way.

The woman fucking him had been staring curiously and intently right from the start. She seemed vaguely amused at how easily Cass had submitted to her, and the longer she stuffed his holes, the more she almost appeared to be gazing tenderly at him.

Certainly her touch was gentle as she stepped right up in front of him and caressed his cheek with her fingertips. It was a bizarrely intimate gesture under the circumstances.

"So cute," the woman murmured, just barely audible.

Cass forgot for a moment that he couldn't directly respond to her, and just kind of made some sloppy, drooly noises through the tentacle filling his mouth and throat.

"I think I might cum in you," the woman continued. "Would that be ok, do you think?"

Cass did his best to nod eagerly, but again didn't have much range of motion available. It seemed to be sufficient, however.

The woman didn't appear to move or do anything at all, but her tentacles inside Cass seemed to pulse with need while fucking him harder than they had been. The extra pressure, the additional sexual sensations, lasted only moments before she shivered, her tentacles strained, and hot cum blasted into Cass.

Cass's eyes rolled back and he moaned loudly. He couldn't sense the cum flowing into him the way he could with his magic butt plug in place, but he could still very much feel it hitting his insides and making an internal mess of him. His tummy felt like it was catching most of it, and gave him the odd sense of having consumed a meal without any food having passed his lips.

There was a brief stillness afterward, a soft breathing from the woman, a faint, shared tingling between them. Then slowly but inevitably, the tentacles started moving again.

It was expected. Hoped for, even. Tentacle sex wasn't meant to be a one-cum kind of affair. Let alone that Cass himself was all worked up and ready for some release of his own.

"She just cum in you?" Vanya asked. "Looked like a good one."

"It was," Cass confirmed. "Think she's gonna go again."

Vanya bit her lip. "You gonna cum? You have that look."

Cass sighed happily. "Soon, I think. She's fucking me again, and she's doing this neat thing to my cock. It feels quite nice."

Cass let himself go in the moment, just enjoying it. Cumming to a tentacle massaging him was unique from being jerked off in a more usual way, more sensuous and squirmy, while of course having the extra oomph of a stuffed butt at the same time too. These tentacles were a trip.

He got no reprieve, nor did he expect one. Instead he just got cummed in again, this time feeling a bit of that satisfying stretch that started to happen after taking a few excessively large loads.

"Alright," Vanya said. "I'm here to help."

It took Cass a second to realize that she was speaking to him in person, and from almost directly behind him. In fact she was close enough to pat his shoulder comfortingly.

He still had to answer through comms, not having a free vocal tract yet. "What are you doing?"

"Helping. Like I said. We're going to need to free you."

"... are you naked?"

Vanya nodded. "Yep. Part of the plan. My dress was nice, I didn't want it shredded like your outfit."

"Vanya, is your plan just to get tentacle-fucked too? Did you just get horny and jealous?"

"Pff, perish the thought. I'm starting to think you don't appreciate being rescued."

Cass rolled his eyes as Vanya was casually encircled with tendrils and lifted up off the ground. She grinned eagerly as she was restrained and bit her lip in anticipation.

"I really don't think this is a rescue," Cass said.

"Just wait," Vanya said. "She'll get busy enough fucking me that at some point she'll get bored of you. It's foolproof!"

"I don't think that word means what you think it means."

It was no good arguing, of course. Vanya was already trapped, and was clearly horny enough that even if she could have escaped, she most likely wouldn't.

"It is not a foolproof plan," the woman binding them both said simply, without arrogance or pretense. "Also when you speak out loud, I can hear everything you say."

Cass sighed and nodded.

Vanya laughed. "Oopsie."

A tentacle invaded her mouth, cutting off her ability to do any more speaking out loud, which was probably just as well. She cooed happily as another pair rubbed across her pussy and butthole, while still more caressed her pink skin.

For some reason the tentacle in Cass's mouth vacated the area at about the same time. He worked his jaw after having it stretched so much, though in reality his game-body could take loads more abuse than a real body ever could, and he really wasn't in bad shape after such a thorough face-fucking.

"What's the plan now, cutie?" the woman asked.

"Heck if I know," Cass admitted. "I really didn't have much of one to start with."

"So it wasn't, say, let me fill you up with cum, then trick me into putting your butt plug back in so you could overpower me with ease?"

Cass shivered with a mild case of dread. "Is that... likely? Do you think?"

"You've done it before."

With a sudden but well-timed movement, the woman shook her body and hair, and her appearance shifted. Not a total transition, but enough of one. Her hair in particular grew longer and became a bright red.

"Ivy?" Cass asked hesitantly.

"That's me!"

"But... we just arrested you," Cass protested. "I swear we did."

Ivy nodded. "Sure. But I've got more characters."

"Not fair! Totally unfair."

She shrugged. "What can I say, I like playing a baddie, and it would no fun always being murdered or rotting in jail or whatever."

"That's probably true," Cass admitted. "Sooo... fill me up a little more and we both go our merry ways?"

Ivy didn't answer, but her smirk didn't make him super hopeful of being accepted.

Vanya was fully enjoying herself, and by the sound of it had been cummed in at least once. She was brought over closer for reasons Cass didn't immediately recognize, though it was soon made clear to him. The tentacle down Vanya's throat was retracted, giving her breathing room just for a moment before she and Cass were shoved together, face to face, mouth to mouth.

"Well this is odd," Cass said through comms.

"It's nice," Vanya said. "Ivy's a fun girl, even if she's technically villainous and always trussing us up and doing what she wants with our bodies."

"You sure you didn't mean that she's fun 'because' she does that?" Cass asked.

"Maybe I did. Why you think she's trying to get us to make out? I mean I don't mind, but-- oh, I see."

Cass frowned. "What? What is it?"

Vanya only cooed happily, and a moment later Cass felt a tentacle coming from her mouth and into his. It caught him by surprise and took him a moment to realize that it must have gone up either Vanya's pussy or ass, straight through her, and was now squirming down to his tummy. Likewise, and truly stuffing his poor throat, the tentacle up his bum was entering Vanya going the other way.

"Now this is inventive," Vanya said in comms while her in person self just gagged and drooled over both of them. "I could be into this."

"Not sure you have much of a choice," Cass said.

"Yeah. Neat, isn't it?"

It was hot, at any rate. Cass wasn't optimistic about their chances of escape at this point, but the captivity itself was fairly exquisite.

It was more fun getting tentacle-fucked with a friend than alone, after all. And making out with Vanya while simultaneously being face-fucked was rather new and interesting.

When another load of cum was shared out between them, it had to flow all the way through one of them into the other. It was a rather tingly and intimate feeling, though under the circumstances it probably couldn't actually be considered wholesome as such.

Cass made out with Vanya with urgency and need, savouring that connection between them as they were pounded and cummed in. She kissed back just as eagerly, and as firmly as possible given that they couldn't actually lock lips properly.

Ivy pulled them apart again after a while, which was disappointing right up until Cass realized she was just rearranging them. His face was shoved into Vanya's butt, his mouth to her bumhole, and he got to sloppily rim her while a tentacle throbbed up his throat and into her ass.

"It's rather embarrassing that I ever got beat by you, you know," Ivy said conversationally. "Given how frankly easy it is capture you. This is twice now, you know. And you practically asked for it this time."

"Huh uhhmmm?" Cass said, doing well to be as intelligible as that under the circumstances.

"I mean yes, I know, I chose the path of villainy, so getting beat is part of the game," Ivy continued. "And I do so enjoy all the fun along the way." She patted one of her own tentacles that was casually swaying beside her. "Before this game I never knew how much fun tentacles could be. Did you ever think about it? Like having a dozen different cocks all at once, only a hundred times as versatile as the real thing."

"Hmmm uh uunh mmh."

Ivy came in Cass again before swapping him and Vanya so that she was face-first in his butt instead. Ivy actually left his mouth free this time.

"I almost feel a villain-like urge to leave you some hope of escape, just to see what happens," Ivy said. "Weird, isn't it?"

"That would be nice of you," Cass said. "I'm getting awfully full."

Ivy's eyes gleamed as she checked out his cum-swollen tummy. It was very obviously over-full now, bulging visibly. He could still take more, he knew, and it was super hot being cumflated like this, knowing he could go back to normal when given the chance. It would be a little scary if he couldn't, or if he were in danger of being impregnated by her. That would be a little much. Although....