Gaming vs. Femboy Ch. 06

A tentacle prodded and soothingly rubbed Cass's poor, stretched belly.

"You are quite full, 'tis true," Ivy agreed. "I think we can probably do better still."

Cass groaned. "I know I'm stretchy, but I genuinely still have limits."

"Exciting, isn't it? I kind of feel like cum will probably have to start leaking back out of you as fast as it goes in at some point."

Vanya, busily getting fucked and licking Cass's butthole to the best of her ability, nevertheless had the focus to agree excitedly in comms. "Yes yes yes! Tell her yes! That sounds amazing."

Cass sighed. "Heck with you both. What's the point getting cummed in so much it all gets wasted?"

Ivy cocked her head. "All in your definition of 'wasted' I suppose."

"... this is happening, isn't it?"

"Oh most definitely."

The next load of cum pumped inside Cass really made him start to feel overburdened. It was getting to the edge of making all his cum-stretched glory not feel quite so sexy or luxurious. Only being fucked by one tentacle up his butt at a time now, nothing down his throat, did moderate the incoming flow a bit, which was helpful. Even so, the next load after that broke his body's limits.

Cass coughed and choked as cum with nowhere to go came back up his throat, over his tongue from the wrong direction, and ended up spilling and drooling all over his chin, neck, and chest. More kept coming, sometimes launching unpredictably, sometimes spilling almost straight down over his increasingly messy body.

Even his ass wasn't managing to hold on. Cass could feel cum shooting back out around Ivy's tentacle, and he could watch Vanya's face on comms as spurt after spurt of ejected cum splashed on her cute face, turning her into the same sort of slutty mess he felt like.

"Fuck that's hot," Ivy whispered. "As good as I could have hoped."

"Hehe, bet she's screenshotting the heck out of this," Vanya giggled over comms. "Or recording the whole thing, maybe."

"You can do that?" Cass asked.

"Well... technically it takes a fair amount of space to record depending on how you do it. If you know how to use the system, you can pare it down to a regular two-dimension video file shot at a specific framing and angle. Or you can go big and save the whole scene to watch any way you want. Or you can do what I do and just snap some pics here and there. Much easier on storage space."

Cass frowned. "You're doing that now, aren't you?"

"When I have some extra mental ability free, sure. Want to see my pics after?" Vanya asked.

"I want to say no, but... yes, let me see them at some point."

Vanya beamed triumphantly and put some extra effort into tonguing his bum as a reward of sorts. Cass found it hard to believe that at this point people would still be putting effort into corrupting him, yet it certainly seemed to be the case. More worrisome was that it so often worked.

Another gusher of cum flowed into Cass and right back out his messy holes. He came again himself while being decadently overfilled, and the combination left him really quite sexily plastered.

"I just want you to know," Cass sputtered while trying to sound serious, "that another five or six of those and I'm going to be forced to escape your clutches and visit judgement upon you."

Ivy blinked. "You are?"

"Yes."

"How?"

"Haven't got that far yet," Cass admitted. "I'm hoping I'll come up with something."

Ivy examined him. He presumed there was very little bare skin showing at this point, most of it being cum-covered, and his midsection was all ballooned out from how stuffed his insides were. A body really shouldn't be able to take this much punishment, and he fully intended to do something about it if she insisted on cumming in him several more times in a row. He had to put his foot down on that.

"Five or six more times, huh?" Ivy asked.

"I have to set firm boundaries," Cass said. "Otherwise people will just do whatever they want to me."

"Ah, well, I have to respect standing up for yourself," Ivy said with more than a little amusement in her tone.

She stuffed Cass's mouth full with a tentacle again, delving deep down into him and into Vanya's mouth as well via his bum. She fucked him hard from both ends for a while before cumming again, and causing another messy explosion all over him and Vanya. The oral tentacle retracted afterward so he could talk again.

"Truth be told, I probably have to let you go sooner or later," Ivy said. "Eventually your commander is going to stop ignoring this and do something about me."

"Ash is deliberately letting this happen?!" Cass exclaimed. He paused for a moment and thought about it. "Oh right, it's this group. Of course they're letting this happen to me."

"To us," Vanya helpfully chimed in. "I'm here too. But also yeah, pretty great, isn't it? Ash got our back."

"That very much depends on what you think 'having our back' means in this scenario," Cass replied directly to her.

"I think--"

"I know what you think it means. Don't explain." Cass turned back to Ivy. "So we're agreed then? You'll let us be on our way?"

"I didn't say that," Ivy said. "But I'm willing to bargain."

"But... you just gave away all of your leverage by reminding us it's only a matter of time before we win and you have to let us go anyway," Cass said.

"I do have to let you go," Ivy agreed. "But I could, just for instance, let you go right in front of our giant who is still standing. The image of you getting stomped and squirting everywhere like a jelly donut is kind of funny, but would probably be a little more macabre in actuality than I really want to see happen to you."

"Ohhh, threats of violence," Cass said, nodding knowledgeably. "I forgot about those. Well played."

"Thank you. So I'm thinking perhaps a mutually beneficial exchange might be in order," Ivy suggested.

"I'm not sure I have much to exchange," Cass said.

"You have an artifact of great power and particular interest," Ivy said.

"I don't, do I? Wait, no, my butt plug? No, you can't have that."

"Why not."

"It's literally the source of all my power," Cass said. "I feel like I shouldn't have to explain that to you of all people."

Ivy prodded his swollen tummy. "Maybe the real power was inside you all along."

"Well yes, technically my powers have come from within, but only after someone put them there," Cass said. "And possession of my plug is still key to unlocking that power."

Ivy shrugged. "There's a greater power waiting for you ahead in these trials. That's something to consider."

"... is it friendship? Because I swear if it's friendship I shall be very cross."

"Pff, good lord no. I've seen your friends. That power is questionable at best."

"Agreed," Cass said. He mulled over his options. "So... either I give you my most powerful magic and get to go hopefully get something else to replace it but really can't fully trust that it'll be worth the exchange," he said. "Or else I get threatened with a cartoonish death and all this time and effort getting here was probably wasted."

"Not wasted," Vanya chastised. "I've thoroughly enjoyed myself."

"That's about the bargain alright," Ivy said. "Unless you have a better counter-offer?"

"Not really," Cass sighed. "Give me a minute." He switched back to comms. "What do you think, Vanya?"

"Stall as long as possible," Vanya advised.

"Because you think Ash will save us? Or because you just want to get fucked and cummed in more?"

"... I don't have to answer that."

"Right." Cass pulled up Ash on comms. "Hey, Ash. I've got a conundrum here and--"

"Take the deal," Ash said.

"What?"

"Vanya's been filling me in. This sounds like an opportunity for character growth which may well come with more power than ever before. And let's face it, your butt plug is a crutch that's going to hamper your ability to learn your own potential in the long run and...."

Cass let Ash patter on for another few minutes, marveling at how verbose they could be when it came to intricacies and minutiae of the game. He got cummed in again in the meantime, so was a little dazed as he butted back in.

"So it's a good idea?" Cass prompted. "I really just kind of need a simple answer. I still don't understand half this game and how it works."

"Your percentage of understaning is far worse than that," Ash said. "But yes, statistically it's the best option."

"But not definitely?"

"Heck no. Could be a trap."

"Great." Cass refocused on Ivy. "I've been advised to take the deal."

"Fantastic!"

"Am I allowed to put in a caveat that if this goes badly for me, I'm going to hunt you down and take my plug back while also meting out legally questionable but personally satisfying justice?"

"Goes without saying, really," Ivy said. One of her tentacles picked up Cass's plug off the floor. "Transfer the item, please."

Cass blinked. "You're literally holding it already."

"Yes, but it's still attuned to you. I need you to give it to me."

Cass shrugged, or tried to given that his arms were still restrained, and accepted his plug into his hand before symbolically passing it right back to Ivy. He felt a pang of loss seeing it go, but hoped that it was going to a good home.

Ivy then gently carried him over to the edge of the field and set him down safely. On the side he wanted to be on, even, which was promising.

Unfortunately for Cass, he was about twice his usual weight and size, considering all the cum in him, and his outer coating made him extremely slippery. He turtled on his back for a moment, flailing about uselessly until Ivy took pity and picked him up again, setting him on his feet this time and prodding him off with a quick smack on the butt from one of her tentacles.

"Good luck, cute boi," Ivy called.

"Yeah, good luck Cassie," Vanya called. Her mouth was briefly freed so she could speak aloud this time. "I've got her on the ropes. I'll be right behind you."

Ash grunted something vaguely supportive through comms, then went back to what they were doing. Ivy meanwhile gave Vanya a disbelieving look that she could be at all confident in her ability to come out victorious, and unceremoniously shoved her full of tentacles again. Vanya was already about as big around as Cass, having been filled a similar amount, and it looked like Ivy wanted to find out just how much more she could take. Presumably, Vanya was curious about the same thing.

Alone, feeling much more powerless than he was used to, and having to walk very carefully in his condition, Cass padded onward toward a path leading upward and to the next challenge.

****

"Before you are three doors!"

Cass sighed. His trudging had become a little easier as he'd been carefully siphoning cum back out of his structurally stressed body with his Flask of Much Liquid, but he still wasn't in prime shape for long walks.

"There are three guards!"

"Logic puzzles now?" Cass asked aloud. "Is that what we're doing?"

"One guard always tells the truth!"

"One guard always lies?" Cass guessed.

"One guard always lies!"

"Uh huh. What's the third one do?" Cass asked, well aware that there was no one particularly listening to him. He wasn't even totally sure the voice he was hearing was coming from anywhere, really. It just sort of was.

"One guard stabs people who ask tricky questions!"

"Ah. Cunning."

"One door leads to glory! The other two doors lead to doom and peril!"

"Like one leads to doom and one leads to peril? Or do they both lead to a combined doom and peril?" Cass put his flask back to his lips and experienced more of the odd sensation of cum flowing up his throat and alleviating pressure on his body. It still tasted like regular cum going this direction, and it was odd to think about how used to it he was these days. And how much he actually kind of liked it.

"Choose wisely!"

Cass stopped before reaching the three menacing looking guards. They were fully armoured, preventing any facial clues, and well armed as well. He, meanwhile, remained soaked and largely filled with cum, and was clad in only thigh highs and a new pair of panties he'd donned. He technically had more clean clothes available, but he remained messy enough that he wasn't convinced it was worth a full wardrobe revamp just yet.

Unfortunately, this looked like a situation where being smol and cute wouldn't avail him all that well. Nor, he suspected, would any amount of sluttiness. Given that brute force was also out at the moment, he didn't have much left to work with.

"So what if I just go through the middle door?" Cass asked aloud.

"You will find glory!" one guard said at the same time as another assured him, "You will find doom and peril!"

The third guard unsheathed a wicked looking blade, which at least gave away one identity quite neatly.

"That's not a tricky question," Cass insisted promptly. "You can't stab me yet."

The guard hesitated.

"It was a regular question, if anything," Cass continued. "If not a hypothetical musing out loud to myself, which I think should be fair enough under the parameters."

The guard sullenly sheathed his weapon again, but silently managed to give a very good impression of just waiting for Cass to slip up.

"Now then, I could probably ask a tricky and hopefully useful question and just do my best to escape before being murdered," Cass said. "Still not a question, don't glare at me like that."

"Or I could just pick a door," he continued, stepping past the guards who didn't actually seem to have any interest in preventing him from reaching the doors. "Actually, is there anything to prevent me from just peeking through the doors?" He looked over his shoulder at Stabby-Guard. "That's a clarification question, and not a tricksy one."

No one stopped him from putting a hand on one of the doors, but as he touched it the expositional voice rang out again.

"Be ye aware, as ye open a door, so shall ye enter it!"

"Very formal of you," Cass muttered. "Doesn't really let me get a good peek, does it? What if one just has fire and gnashing teeth behind it. That would give me a better shot of not selecting doom and peril."

Cass padded back and forth for a few moments, then gave up and contacted Ash.

"Hey Ash, need some help. You almost done back there?"

Ash's expression went mildly embarrassed. "Um... might have started another round."

"You what? Why?"

Ash shrugged. "Fun."

"Aw jeez. And Vanya?"

"Still with Ivy."

Cass shook his head. "How can she still take more? She was overflowing before I even left."

"They took a break to empty her out first," Ash said.

"Oh good. Well as long as they're being safe," Cass said, only a touch sarcastically.

Scar's face popped into comms. "Hey, Cass."

"Oh hey. Where are you?"

"With Ash and Vanya. Fucked my encounter into submission. It was a good time."

"Oh sure," Cass said. "Any chance you could come help? I'm at one of those three guard type puzzles, and I'm at a pretty good chance of being murdered, doomed, and imperiled as things stand."

"You want me to help with a puzzle?" Scar asked.

"Well, you know, worst case you could swiftly dispatch the guard who wants to stab me. Give us a better chance."

"Alright, let me mow through this chessboard thing and--"

"It's turn-based," Ash said.

"Oh you motherfucker!" Scar swore.

Cass giggled at Scar's sudden realization that she'd have to be patient, but as amusing as it was it didn't really help him at the moment. He left his friends to their activities, and turned back to his task. He really just wanted to pick a door and be done with it. He was a little antsy about surrendering what was by far his best equipment, and wanted to find out if it had been worthwhile. It didn't leave much room for potential satisfaction at being a smarty-pants.

"Hey Stabby," Cass said, switching off comms for now. "Would you mind helping me with this door? I think I'm just gonna pick one and see. I am so smol and helpless and probably a ditz too."

The guard gave the distinct impression of giving a suspicious frown, but after a moment did come over to open Cass's door for him. That gave Cass a hint that maybe it was the wrong door, since there was a chance Stabby-Guard was only helping him make a wrong choice. On the other hand, maybe Stabby was actually a really helpful NPC who just happened to be foisted onto the role of stabbing people. It was tough to say for sure.

"Thank you so mu--" Cass started to say.

As the guard swung the door open, a small inferno mixed with the screams of damned souls engulfed the guard right where he stood. As the door swung shut again, the now empty armour collapsed cartoon-style on the floor.

Cass stared at what could have been his poor little self if he hadn't been careful, the shrugged. "Guess it's not that door." He slowly turned toward another guard and batted his eyes winsomely. "Heyyy, could you please open that door over there for me? I am smol and pitiful and etcetera."

The two remaining guards looked at each other a moment, then one gave the distinct impression of sighing loudly without actually making any noise at all. This one moved to the door that was not the one Cass had indicated and opened it instead. Doom and peril graciously failed to make themselves known.

"Man, I'm bad at picking doors as it turns out," Cass said. He breezed past the guard holding the door for him, stopping to stand on tiptoe and place a kiss toward the cheek area of his armour, as high as he could manage to reach. "Thank yooouuu."

"You know, once you'd determined which guard wanted to stab you for being tricksy, you could have eliminated him then asked one of us what the other would say is the wrong door," the guard said, sounding just a touch hurt at the game not being played properly.

Cass blinked. "Oh? Well, very helpful, thanks. But I genuinely am quite smol and helpless at the moment, and pretty sure I couldn't take any of you in a fair fight."

"... then how did you possibly get this far?"

"My friends are very helpful that way. Sometimes they're even competent. If they come by later could you...." Cass paused. "Actually no, Ash can figure this out. They'll be fine. Thanks again!"

Cass waved cheerfully and carried on his merry way. He waited until the door closed behind him before somewhat awkwardly pulling his panties aside and sticking his flask up his bum, letting some cum drain out of him from that end and decreasing his internal surplus a little more. There might be more danger ahead, and it was probably his best bet to at least be mobile if and when he reached it.

****

Cass didn't empty himself out completely on his walk. He left his tummy rounded out a bit, enough to remain overfilled but still nimble. He was in the process of deciding how to handle the mess still all over his skin, which hadn't dried much or even particularly cooled in all this time. He kind of loved this game's sexy logic and physics at times.

The next room he entered gave him the sense of being near the top of the mountain, and hopefully close to his goal. There were some open air windows carved out of the rock here, giving a view of sunlight and drifting clouds. The room itself was large and decorative, but he couldn't immediately see what the obstacle was meant to be in this case.

Cass padded forward, idly dipping his finger in some of his cum coating from time to time and sucking it clean again. An inefficient cleaning technique, sure, but an entertaining one.

He got a little edgy as he proceeded and didn't take note of anything or anyone trying to stop him. He got even more skittish upon locating a boy near the far doorway who was just kind of sitting moodily against the wall. It could very easily be a trap. Most anything in this game could be if one wasn't careful.

Cass kept his eyes darting about as he carefully approached. He vaguely wished he was dressed a little more appropriately, as trying to sneak up to someone while mostly naked didn't quite give the right vibes.