Gaming vs. Femboy Ch. 07

"So we really only came away with a paltry sum of gold, and some fairly mediocre magic items that will in turn probably be sold for yet another paltry sum of gold," Ash summarized.

"It's not about treasure," Vanya argued. "It's about the cums we had along the way."

Cass, leading the way down the winding mountain path, let his new wings stretch out to either side and flutter a bit in the soft breeze. They were another source of sensuality for him now, just the right level of sensitive to truly enjoy the wind's tender caress. Much like experiencing the perfect riffle of air through his hair on a hot summer's day.

"I'm happy with what I got," Cass said.

"Well of course you are, Cassie," Vanya laughed. "As if we needed you to be even cuter and sluttier."

She brushed her hands against Cass's wings, making him shiver in wonderful ways.

"What do you mean sluttier?" Cass demanded.

Vanya's hand moved to the bare skin at the small of Cass's back. "Well your current dress is preeettty open back here. Just saying."

"That's only so my wings fit," Cass insisted.

He rather liked how the dress looked on him, short and open-backed though it may be.

"It's open almost all the way to your butt," Vanya teased.

"My wings mostly cover that," Cass mumbled, folding his wings back up shyly.

"I think you look good," Scar said.

Cass tossed her an appreciative smile over his shoulder. "Thank you."

"Well so I," Vanya said. "Never said I didn't."

"Only because you like slutty boys though," Scar said.

"I like cute boys," Vanya pouted. "Slutty is only a nice perk on top. You're the one who really goes for sluttiness."

"You two are arguing like you're not both walking behind me on purpose," Cass said. "Pervs the lot of you."

There was silence for a moment, and Cass didn't quite dare look back at any of his party. He knew he was right though. At least going down the mountain they didn't all have the chance to peek up his dress from behind anymore.

"It's a hell of a view, is all," Scar finally said.

Cass nodded. Whether she referring to him or not was purposefully unclear. The stunning vista as they descended was well worth the hike all on its own. A broad, artistic landscape dotted with idealized clouds and birdsong, and even an improbable but beautiful rainbow off to one side.

Cass allowed said view to entice him as they came to a bend in the path that coincidentally--or rather by deliberate design, most like--featured a small, cozy resting place with grass and some shady trees. They'd earned a break, he felt, and it was such a lovely view after all.

"We should stop for a bit," Cass decided aloud.

"Tired already?" Scar asked.

Cass shrugged. "Well, you know, I am only a smol boi, and it is ever such a big mountain."

Vanya laughed and flopped down on the grass. "You get better and better at abusing your cuteness every day," she said. "Not that I'm complaining."

Cass glanced at her, and was pretty sure she had her eyes locked on the hem of his dress, particularly when the wind whipped it about from time to time. He let her have her fun. He had panties on, and he was pretty sure his dress wasn't blowing up all that much anyway. Not like his skirt earlier in the day. This was more of a tease than anything.

"He does at that," Scar agreed, sitting down against one of the handy trees.

Ash was already lounging in the shade, and Cass honestly had no idea when they'd done so. They just seemed to have gone from marching to skulking without any intervening motion.

Since he now had tacit unanimous agreement, Cass settled himself down as well. He opted to curl up next to Scar and let her pet him like a puppy, alternately stroking his hair and his wings. It was incredibly soothing and relaxing, and in the coziness of the area and company, he could have just fallen asleep right there.

"Cass," Vanya called after a while.

Cass murmured something and ignored her.

"Caaasss. Cass!"

Cass cracked an eye open. "What? I'm relaxing."

"I know," Vanya said. "I can see that. Only I saved a lot of cum for you, and it would be reeeaaally nice to get it emptied out before we carry on."

Pouting a bit at having to so much as raise his head from Scar's lap, Cass examined Vanya. She'd apparently opted to remove all her clothes entirely, and was currently stretched out on the soft grass, partly covered by shade so that sunlight only dappled across her smooth, pink skin. She would have made an artistic and erotic sight ordinarily, but she was currently stuffed with enough cum to appear heavily pregnant, and that detail left her appearing downright lewd in her current state.

"That is a lot of cum," Cass said thoughtfully.

He'd been just as stuffed already that day and wasn't ready for another dose of the same just yet. But helping clean Vanya out wasn't the same as getting pumped full of cum, and he was admittedly kind of horny again. Arousal tended to happen one way or another in this game, and with this group in particular. Having his wings petted turned out to be as good as foreplay to him, which only made things more interesting.

Cass lazily stretched and sat up in Scar's lap to kiss her. "Gonna go play," he said.

"Mmhm," Scar said, patting his bum fondly. "Probably just as well. Vanya's actually a bit off-putting, all bulging and sloshing like that."

"I am not!" Vanya said.

"You are," Scar said. "And if we're speaking about slutty again...."

Vanya frowned. "And what if it was your cum in me? Would that be gross too?"

Scar considered the proposition. "That'd be pretty hot in that case, I think. Yeah, definitely hot."

"Rather hypocritical of you then, isn't it?" Vanya said.

"I dunno," Scar argued airily. "I think it just makes sense to enjoy my cum filling someone up more than I enjoy someone else's cum doing the same."

"I kinda get it," Cass said. "I mean, I like it either way. But when I came in Azrael before and made his tummy stretch a little, it was pretty hot that I did that."

"You don't cum that much, sweet thing," Scar said. "And none of us have met this alleged angel boi you keep mentioning."

"I cum more now," Cass said a tad sulkily. "You just haven't had a chance to appreciate what my new powers do."

"You haven't told us what they do," Scar said.

"Well... I don't know how to find out what they are," Cass said. "But I have wings and I cum more than before. So there's that."

"A solid upgrade," Vanya said cheerfully. She stretched out her hands and made grasping motions. "Now come here, licky boi. Time for treats."

"Damn, I can't say no to treats," Cass said. "Alright then."

He wriggled out of Scar's lap and her embrace, and chose to leave his dress behind when she teasingly held on to it. He crawled across the grass in just his panties and thigh highs, well aware of what he must look like while doing so. That was the thing about being horny. The hornier he was, the less concern he had with looking slutty in front of other people, especially if they were already friends.

Sensing the attention on him, Cass gave his booty some extra wiggle during his brief crawl. He slipped himself between Vanya's legs, nestling mostly naked next to her pussy, and started kissing her sensitive areas. She squealed happily and tried to grab his hair, but her own cummy tummy got in the way.

"Damn it," Vanya whined. "I can't even see you down there."

"Perils of being a cum balloon," Scar laughed without a trace of sympathy.

"Don't worry," Cass said. "I'll take care of it."

He stuck his tongue up Vanya's snatch, finding and scooping out a tasty mouthful of cum. She purred in contentment and allowed the luxurious treatment, though continued to try reaching for him.

"Be hotter if I could see it, is all," Vanya said. "Might have get some screenshots, I guess."

"Never fear," Scar said. "Already on it."

Cass bit his lip at the reminder of proof of his sexy activities. Vanya had told him she had some from when they'd been tentacle-fucked together, and apparently there would be more from him cleaning her back out from that very same escapade.

Thinking about it didn't stop him for long. He'd already decided he was curious to see these kinds of pics afterward, and it wasn't exactly surprising that his friends would be saving memories this way. They were pervier than he was, if anything. Or so he told himself anyway.

Cass decided to ignore his few lingering doubts about whether he truly wanted to see himself from the outside while face-deep in cummy pussy, or stuffed full of tentacles. They were only small, self-conscious fears. Even if it was weird to watch himself, it was still kind of hot to think about, and he could always focus on Vanya if he wanted to. She was easy to appreciate, even when she wasn't naked and lewd.

There was a never-ending supply of cum meeting his tongue as he licked. Like he couldn't swallow it fast enough to meet demand, and despite his best efforts some of it spilled down his chin from time to time. It was addicting and fun, and he kept trying his very best. Slowly but inevitably he felt his own tummy fill up at nearly the same rate as he was emptying Vanya out.

Without giving it much thought, Cass pulled out his Flask of Much Liquid and tugged his panties aside so he could stick it up his bum. He let the cum inside him drain back to a manageable level while he kept greedily sucking down more.

"That's kind of cheating, you know," Vanya said.

"Thought you couldn't see me around your huge tummy," Cass teased.

"Still mostly can't. But you're bringing it down some."

Indeed, Vanya was already noticeably smaller than before.

"You think I should be the size you were for the rest of the walk?" Cass asked.

"Well...."

Cass shook his head. "Pff, no thanks. I'll save it for later, thank you very much."

"Save it for what?" Scar asked. "Seeing as how you gave away your magic butt plug that let you make use of excess cum."

Cass blushed, acknowledging that it was a very good point, as well as that he intended to hang on to all this wonderful cum even if he didn't technically have a good reason. He blushed even harder when he looked at Scar and noted that she had her pants off, and was lazily stroking her cock while she watched him and Vanya.

Scar's orc character was a dominating muscle-mommy anyway, let alone in comparison to his smol stature. Cass didn't usually see her playing with herself when she could be trying to shove her huge cock in someone else. It was kind of scary when he realized how big she looked in comparison to her own hand, never mind how her erection compared to his whole body. Still, he'd technically taken her before, if only down his throat with the aid of magical chokers. He could do it.

"Just... just saving it," Cass mumbled.

Scar grinned, noting his eyeline. "Getting horny over there, baby boi?"

Cass buried his face back in Vanya's messy snatch to avoid answering.

"Bet he is," Vanya cooed, managing to pat Cass's head affectionately as her tummy got just enough out of her way. "You should help him out."

"Was thinking the same thing," Scar said.

"No! No, you will not fit," Cass said firmly. "You all know this."

"Actually," Ash said.

Cass glared at them, feeling betrayed by the person he most regarded as being sensible and competent in the group. Ash had already left him to the mercies of a tentacle-woman today, and now refused to save him from Scar's femboy-destroying cock.

"Et tu, Ash?" Cass asked.

Ash smirked and continued to feign nonchalance, despite clearly watching the whole of the proceedings. "Actually, angelic as well as demonic prestige races are rather famed for having better sexual capacity by default. There's a pretty good chance Scar will fit now, even without magical help."

Cass processed the information, trying to decide if he still felt betrayed, or whether this news was interesting and worth investigating. It could be both, sure, but Cass was horny enough he couldn't do a very good job of pretending he wasn't intrigued by the possibilities. Slutty as it may be, he had rather enjoyed Scar stuffing his face full, and throat-fucking wasn't even nearly as pleasurable as anal play on a physical level.

Still, he couldn't help swallowing nervously at the thought of Scar's orc cock somehow entering his tight little bum. It just didn't seem physically possible. But at least physical impossibility wasn't really relevant to how this world worked.

Cass licked some more cum out of Vanya while he thought. He wasn't really getting anywhere with his internal decision making, but he really felt like he should be able to come with something other than the same few points over and over.

It was a slutty thing to do, which was fine because he was horny and feeling slutty. It might not work and might hurt, which were valid concerns. But also he did need to find out the limits of his new body. But what good was that if he died in the attempt? It probably wouldn't come to that. But what if it did? But....

"You ok there, Cassie?" Vanya asked, ruffling his hair. "You're feeling awfully mechanical all of a sudden."

"Sorry," Cass said, kissing her pussy by way of apology. "Just thinking."

Scar hadn't moved, hadn't done anything other than to regard him curiously and continue stroking herself.

"You wanna see if she can fit in you, huh?" Vanya said.

Cass lifted his head. He could meet Vanya's eyes fairly easily now. He'd eaten more cum from her than he'd realized.

"Maybe," he said.

"Well there's only one way to really know."

Cass stuck his lip out poutily. "You're biased. You want to see it too."

"True," Vanya said. "Doesn't mean I'm wrong."

Cass turned to Scar. "What about you? You have non-biased advice?"

Scar grinned. "Oh baby boi, I'm getting in that ass sooner or later, even if it's not today. But you already knew that, didn't you? You being an angel just makes it more tempting. Never pounded an angel before."

Cass shook his head but felt happy little butterflies inside. He remained nervous, but he couldn't deny it was an exciting prospect. Especially knowing that the others were eager for it as well. Scar wanting to be inside him was a very nice feeling, even if it was no surprise at all.

"Ash?" Cass asked, looking either for a way out, or perhaps unanimous approval.

Ash was gone. Cass frowned and wasn't sure what to make of that. His confusion only lasted a moment before he felt soft, sneaky hands on his booty.

"You'll need lubed up," Ash said from behind him.

Cass gasped. "Don't sneak up on me like that."

"Can't help it. I'm sneaky," Ash said, as though that explained anything.

"They're right," Vanya said. "You do need lubed up."

"I never said I was gonna do it yet," Cass said.

Vanya rolled her eyes. "Bruh."

"I'm capable of thinking horny thoughts but not doing anything about them, you know," Cass said.

"So that's what we're doing today?" Scar asked, standing and stretching, which was quite the sight. "We're just telling lies?"

Cass swallowed hard as his eyes traveled the length of Scar's body. Her remaining clothes disappeared even as he scanned her, making her even harder to look away from. Just the sheer expanse of toned, muscled, sexily scarred green flesh on display made her near-impossible to resist.

The complex feelings he had for her were a whole other thing. He'd done well so far separating her in game character from his best friend in real life, even though they were still kind of mostly the same person. He carried on in that tradition, enjoying the sexual nature of their game relationship and the possibilities she represented. He wanted her and she wanted him, and the fact that it was so mutual only made him want her more. Real life consequences be damned, this was fun.

At some point Cass realized that he was more concerned with how his and Scarlett's relationship might be affected in the real world than he was about whether he could actually handle Scar's cock right now. It was potentially a sign of oddly placed priorities, or it could be that his priorities were right where they should be, depending on how he looked at it.

In any case, his thoughts were interrupted by his panties being removed and Ash's highly distracting fingers wiggling up his bum. Ash was a lithe and nimble sort anyway, but Cass hadn't previously appreciated quite what that could mean when getting fingered by them. It was a sudden, sensuous experience that made Cass gasp and freeze up, though he soon arched his back and tacitly begged for more once he had a chance to process what he wanted.

"Naturally lubed, nice," Ash murmured, long elven fingers working in and out of Cass's bottom. "Still probably want some extra for Scar. She's massive, after all."

Cass moaned as he got fingered and more lube got added, slowly being worked all over his asshole and as deep inside as Ash could reach, which was surprisingly far. Cass slowly relaxed into it and let himself melt into a happy, horny boi.

He let his face sink down to the ground while leaving his butt up in the air, wiggling it occasionally to encourage more fingering. He would have kept sinking toward the ground as his body succumbed to total anal relaxation, except that Scar slowly approached and brought her massive erection with her. She quite literally blocked out the sun from where she stood, and her erection appeared even more intimidating that usual from Cass's current angle.

"So this is how I die," Cass gurgled, still enjoying being prepped.

"You big drama princess," Scar snorted. "I don't have to fuck you if it's too scary."

"It is scary!" Cass insisted. "But we should, you know, probably try it anyway. For science."

"Right, for science. Not at all because you're a horny, slutty little thing and desperately need mommy's dick."

Cass tried to act shocked at such an accusation, but the truth was just the words alone were enough to make him all warm and tingly, and even though he was still nervous he was getting to stupidly excited for this. He looked up at Scar from the ground with his biggest, most adorable puppy boi eyes.

"Pwease be gentle with me. I am smol and delicate."

Scar rolled her eyes and shook her head in disbelief at his acting, but he also noted how her cock twitched as he spoke.

Ash, rather obviously amused, nevertheless remained focused and business-like. They swapped over to lubing up Scar's cock, which took some time regardless of how efficiently she was handled.

Cass pushed himself back up on his hands and wiggled his booty some more, enticing Scar while she was prepared. He grinned as he watched precum slowly leak from her cock. Knowing she was as excited as he was and wanted it just as badly was almost as hot to him as the imagined physical sensations of what was to come. Combined, he was already struggling to remember why he'd had to think about it in the first place instead of just diving in.

Once Scar moved behind him and slapped the full weight of her cock down on his ass and lower back, following the line of his spine, Cass remembered why it was still kind of scary. She was so heavy, so long, so thick. Her cock was sexy and thrilling to conceivably have inside of him, but worrisome too.

"Don't tense up, Cass," Scar said.

"Wasn't on purpose," Cass said. "And you very well know it."

Scar dragged her cock slowly back along his butt, then slid forward. Her grinding on his ass was very nice, though didn't actually help his relaxing that much.

"Do you want this?" Scar asked.

Cass hesitated, then nodded. "Yes."

She smacked his booty. "That wasn't very convincing."

Cass gasped and rocked forward, then pressed back more eagerly against her cock. "Yes!"

Scar spanked him again, which for some reason was really working for him. He encouraged a few more smacks, pressing back more eagerly with every one and letting himself sink into the moment, totally glossing over his nerves.