Greed's Best Oysters

(Second story I ever wrote and posted, don't know how to describe it so I'll tag simply.
Helluva Boss, Millie, Crimson, Castration)

Millie looked out the window of the I.M.P van, parked in an alley outside of Crimson's estate. She was trying to go over the layout in her mind, trying to remember all the corridors and rooms.

“You sure about this Mills? We could get in a lot of shit for killing a boss like him.” Blitzo commented from the driver seat, more nervous about the little mission than his companion.

“I'm not gonna kill him, just… tame him?” Millie turned around and reached into the back seat of the van, gathering a small bag of tools that she could bring in.

“Tame him how? Offer him this ass and he's gonna be begging for more.” Blitzo gave Millie's rear a squeeze as she dug around in the back, earning a little whip from her tail.

“No! I'm not fucking that piece of shit. I think making some Wrath style oysters will be more effective.” Millie returned to her seat, slipping the bag onto her back and hopping out of the car.

“What kind of bumpkin shit are you talking about? There are no oceans or shit in Wrath.” Blitzo said with a bit of annoyance.

“Nope, but when we have a couple too many male hell hoglets at my family's farm, we have oysters for dinner~” Millie paused at the door and spread her legs a bit, motioning scissors cutting against her groin while explaining. Blitzo squinted while listening, taking a while to understand before crossing his legs and covering his crotch.

“Don't you ever tell me about your weird country fetishes again!” Blitzo yelled, actually a bit scared as Millie just giggled and shut the door. Even if he wasn't scared of getting a similar fate, he couldn't argue with the logic. Not many demons announce they've been snipped in any way, so why would a boss like Crimson do so?

Millie snuck away, down the street and around the perimeter of the estate. She watched them long with to know their patrol patterns, if they decided to do them instead of slacking off. Getting over the fence was easy, as well as getting to the building. Once inside she found an air vent and crawled inside, using her old solo. Methods to get deep in an area without being noticed. It was also a lot easier with these fish, since they couldn't smell or hear as good as hounds.

Eventually the imp found her way to the master bedroom, pushing the vent off the hinges just enough to slip into the room. There the boss laid on his bed, sprawled across the whole of the mattress in Little more than his boxers and tank top. Millie had to pause for a moment when she walked up, just a little jealous of the fact that Moxxie didn't have as wide hips as his dad. But the thick thighs and stellar waist was definitely inherited, making her regret not bringing her strap.

But she was here in a mission, so she took the bag from her back and got some rope. The similar proportions did make it all easier, quietly tying Crimson's legs to the bottom posts before braiding his forearms together and tying it to one of the top posts. Millie had used the position a couple times a month to tease and edge Moxxie all night, so she knew it would be secure for his father.

As she checked her knots she could see something stir, his boxers starting to surge and grow in his pants. A giggle escaped Millie as she watched the little boss stand at attention, actually adorable with how much smaller it was than his sons. The imp sized tent did give her some joy though, since the rest of his otherwise impressive bulge was all delicacy.

His eyes started to lightly flutter, pulling mindlessly on the ropes and stretching against them. A raspy growl escaped him with a groan, reminiscent to his son as he pushed his hips out against his boxers.

“The fuck is this?” Crimson barked in a groggy voice, starting to realize how position. “Alessio before not fine me like-” he growled while looking at the ropes, lost until he saw another pair of yellow eyes in the darkness. It was a scenario he definitely didn't pay for, so those eyes weren't gonna be friendly to him.

“Good evening Mister Crimson, remember me?” Millie was leaned over the foot of the bed, dimly lit room allowing her eyes to just barely light up her cleavage. It was a haunting but enticing thing to wake up to, something Moxxie loved and it looked like his pa followed that excitement, his cock pushing harder than below.

“Millie… What do you want? Money? Territory? A new in-law?” He gave her a sly smile, trying his best to lighten the situation. But he continued to squirm, testing the ropes and nothing to properly push against. Millie gave an adorable giggle at his offer, an oddly humiliating reaction for the captured Mob Boss.

“No no, I'm more here to do some good. After Blitz did do a little damage to your operation, I wanted to clip those bad ties before they worsen.” Millie hopped up onto the bed, landing on her knees between his legs and placing her bag next to his waist. He growled once again at her approach, more like a trapped animal than a man.

“The fuck does that mean? You gonna spank me doing some other gay shit you do with my son?” A light glow appeared behind his cheeks, red of his face getting a warm glow while the scars started to glow behind him. He was blushing, but it was closest she'll get to an admission of his enjoyment. Millie dug around in her bag and did pull out a couple small tools, a kind of stapler, a jar a black pearl like thing a bit bigger than her palm.

“No, maybe if you didn't try to marry my husband off and kidnap my boss I’d go easy on you. But you kinda remind me of my home, a litte… well more just the hogs. The fat ass does do a bit, but it’s more the attitude.” She unscrewed the jar and placed the lid in her pocket, buying a bit of time before pulling out her knife. Crimson just looked confused at the imp between his legs, unable to really hate it with how much cleavage she offered in her black crop top.

“We don’t need all the male we got, but sometimes the one we decide to keep gets too aggressive. Often they are not fully grown so culling would be a waste, so we… you know” Millie waved her jagged bodied knife at Crimson’s crotch, set up enough to grab the black pearl and giving it a soft squeeze. A purple sclera eye opened on the thing, tendrils quickly growing from its dark body. Crimson picked up on the implications immediately, having made similar threats in the past and fully scared of a woman he knows will go through with it.

“You crazy bitch! Don’t you-!” His voice was cut off as the pearl was tossed at his face, the black limbs wrapping around his face and shoving a few into his mouth. It was a fun sight, watching the gag dance around his face, wrapping his arms around horns and his neck to keep him from just shaking it off. Next was a set of extra tendrils, wrapping around each other and pushing against his tongue and down his throat, causing his head to fall back to allow them to bulge his throat. It was a strong thing, making both her and Moxxie gag the first time it was used on either of them, but Millie could tell Crimson was a little more experienced with the depth than either of them.

“There we go, nice and quiet. Now you just relax and enjoy that little thing in your mouth, I know Moxxie does whenever I get to use it on him~” Mille pushed his shirt up as she spoke, letting the pearl work its magic and loosen his throat in its supernatural manner. His white hair crawled up to his belly button, a soft as down patch of fur that he took exceptional care of. She pulled his boxers down next, the patch stretching down to above his cocklete, a truly adorable thing that she could fully hide in a closed fist with no peaking. But her focus wasn’t to adore his size and stature, but instead to the fat gonads dropping down to barely lay against the mattress below him.

Millie snaked her hands under the fat pair, pulling them up to rest on the taught fabric of his boxers. They throbbed and pulled back a bit, his cock ready to burst with just the use of the pearl and the soft touch. Normally hogs didn’t have such loose sacks, but they also weren’t this protected from the elements.

She pinched the bottom of his red sack and pulled it up a bit from their platform, letting his balls roll back against his body one last time before she brought her knife up. A quick slice removed a 2 inch circle of skin from the bottom of his jewel bag, drawing a jolt and muffled whimper from the boss. Millie giggled and gave Crimson a moment to groan and adapt to the pain, settling quickly as the only breathes he got were shallow around the pearls tendrils. She eventually reached back up and pinched his left gonad, prodding and fishing the plump organ from its compromised pouch and push it into the dim light of the room. The teste escaped with a with a wet pop from its home, opaque white flesh was wrapped in a webbing of black veins, all drawing back and anchoring to the thick cord and artery on the back of it. She repeated the pull and squeeze process on the second, both resting neatly against each other on their platform. They almost put a hell hog to shame with its size, the small pouch holding the pure sperm on the back of his testicle full to a surprising degree.

“Damn, don’t got the time to just jerk off every other day?” Millie asked with a little giggle, sounding more and more sadistic to the trapped imp. The ropes dug into his legs with how he fought, stomach churned and readied to empty. His sack was sore and ached endlessly with the big patch missing from it, each of his balls screaming in every way. They burned as they rested on the boxer fabric, small moisture quickly drying into the threads and tearing away with every roll back and forth thanks to his worthless fighting. Open air sapped the heat of each organ, contrasting the burning sensation with a rapidly growing cold. But despite all the pain, all the humiliation from being caught and castrated like a pig, he was still as hard as his little cock could manage.

Millie had an idea of the pain he was in, only a few seconds having passed since she made the cut and Crimson was already crying and begging to the best of his ability. So she took his cords into her hand, bringing the knife and let the ropes of flesh rest between barbs on her blade. His eyes finally drifted back down to Millie, silently begging one last time despite the fruitlessness. Then with a simple swipe they were free, Crimson's back arching and cock giving a final spasm and a few clear wild spurts cum. The fat orbs rolled a bit more, black blood dripping with a near glowing white sperm, but neither mixing.

Millie could only grin for a moment, putting her knife away and quickly taking the stapler. With two painful placed clicks and the bleeding stopped. She shoved his fat cords back into their that now flabby sack and continued stapling, closing the now slowly swelling pouch and physically ended the torment for the night. Crimson finally started to calm down, dicklet losing its rigidity and falling limp into his bush. It was cuter than a hogs corkscrew, and far more satisfying to watch fade away for one last time. Millie whistled as she turned her attention back to the freshly harvested testicles, staining the boxers they rested on.

“Jeez these are big, you sure Moxxie is your only kid? These are bull sized, with a not as fitting package~.” She gave her own sly smile to the half awake mob boss, picking up what once was his left jewel and dropping it on the jar. But the thing was big enough to get stuck in the rim, forcing Millie to push and squish the things down into the container.

“You know, I some hot sauce would go great with this, but they are always best fresh~” Millie picked up the second severed nad from it's makeshift platform, raising it up to her face and opening wide. Crimson could only watch in tired horror as his daughter in-law sunk her teeth into his manhood, teeth piercing the gleaming teste and causing a spurt of juice to escape before she placed her lips around it. She sucked as she bit through the organ, treating it like a fabulously juicy fruit and not wasting a drop of its nectar. He eventually laid back fully and gave up, only hearing her chew on the flesh. A gleeful squeal eventually escaped Millie, bouncing a little on the bed before she could swallow.

“Satan it's been so long, I missed the old Oysters back home. But I'm thinking now, that Greed has the best ever… or at least had~” She dropped the sampled gonads in the jar, the two occupying the whole of its space thanks to the immense size. Millie packed up the rest of her small equipment, untying Crimson from the posts and letting him rest. He didn't fight back, too exhausted to do anything but pull his limbs back from her and roll where she needed him. The last thing was the pearl, Millie reaching out and gently closing its eye, causing its to slowly retract into itself once again before she put it into her bag as well. She hopped off the bed and put her bag on the ground before walking around, pulling Crimson's boxes back up and tucking him back into bed, earning a adorable whine from him.

“You rest up and make sure not to let anything heavy, those staples can hold up to a lot but it'll take time to heal. And I hope this solves all the problems between us, as well as that anger issue of yours.” Millie leaned in and kissed Crimson on the forehead, a sweet gesture to the Boss before he passed out again. She picked up her things and snuck right back out the same way she came in, effortlessly evading the goons and getting back to the car in only a couple minutes. Blitzo was busy texting when Millie opened the door, causing the larger imp to jump and throw his phone around the car trying to catch it.

“Fuck Mills! Ever heard about warning? Did you get in or-?” Blitzo managed to catch his phone and look back at Millie, just in time for a mason jar to be thrown at his face. He managed to catch the thing and look at it, confused about the still hot black and white stuff inside.

“Turns out Moxxie takes more after his Mom's side.” Millie said with a proud smile, tossing the bag into the back again and buckling up. Blitzo took a while of looking back and forth between the jar and the Impess before it clicked, causing him to wretch and toss the thing back at her.

“Fucking gross, don't you ever show off anymore kinky trophies to me again. I swear, you and Moxxie's are the weirdest imps in bed.” Blitzo said before speeding off, not wanting the details of the mission. His phone buzzed again, a text from Loona telling him that Moxxie got a bit hurt during his solo mission but could be patched up pretty easily.