3 Judgement's Day

The floor GURPS was standing on begins moving as sharp spikes start appearing, he jumps and moves around the spikes but gets nicked by one of those mystical looking chains Judgement sent out.

He recovers quickly without any real harm done as he begins dodging those chains as if he was in the Matrix, eventually the machine stops for a bit and GURPS see's some larger chains attached to the machine. 

GURPS: "Video Game logic tells me those are important" 

He takes out his Saw Cleaver and slashes both chains breaking them as Judgement leaps down onto a platform a bit above him. 

Judgement: "HOW DO YOU LIKE THE SIN MACHINE TRESPASSER? SURRENDER AND LET IT CONSUME YOU!" 

From the "stands" the other girls along with Helltaker are watching the confrontation

 Cerberus: "No wait! Don't give up! you need to help get us out of here!"

Pandemonica: "And I'm still looking forward to my coffee..."

Helltaker: "You got this GURPS! keep going! also please don't die both cause your my friend but also cause she'll come after me next if you die here!"

Judgement: "Leave hope! his fate is sealed and yours will be too!"

Lucifer: "Judgement dear, they may not know it yet but both these men currently belong to me, could you please not damage either of them?"

Judgement: "BE SILENT! REAL WORK IS ABOUT TO BEGIN!" 

The machine starts up again as it picks up speed and more spikes appear, GURPS avoids those as well as dodging more chains as he tries to wait them out again.

This time however Judgement herself tries to attack him directly as she leaps onto the battle field to engage him, they trade attacks with GURPS mostly on the defensive since he doesn't currently want to kill her. 

He is impressed though, if he had to compare her skill in combat to someone then he'd actually compare Judgement to Lady Maria who he fought back at the Astral Clocktower.

Though instead of being as elegant and sharp with her attacks like Maria, Judgement is more brutal and fierce but still skilled in her strikes. 

The machine stops again and seeing his chance GURPS does a trick of turning his left eye into an Amygdala-like eye for just 5 seconds as he blasts a beam of arcane eldritch energy from it that catches Judgement off guard and knocks her back.

GURPS then cuts down the next bigger chains breaking them as Judgement gets back up and smirks as she is able to tie some chains around his arms. 

Judgement: "Those chains that bind you are made of the things that brought you here. Your ego, your greed, your lust... some bloodlust too. You are your own torturer!" 

Lucifer: "ENOUGH! High Prosecutor I order you to stand down at once!" 

Judgement: "NO AUTHORITY STAND ABOVE PUNISHMENT!" 

Justice actually starts clapping 

Justice: "Keep going Judgement. you are on the roll!"

Helltaker: "Seriously?!" 

Justice: "Hey she's doing great at her job, I'm so proud of her"

The angel is busy writing in her notepad 

Azazel: "Yes please continue. this is A+ Material so far!" 

Lucifer seems to actually get red in the face and looks like a mix of angry and embarrassed.

Lucifer: "I'm suppose to be the goddamn Queen of Hell! Why is nobody ever listening to me?!" 

Helltaker just pats her shoulder in a "There there" way as the battle below continues. 

GURPS: "Sorry but I've had my fill of chains on me to last multiple lifetimes!"

Flexing more of his power GURPS is able to break the chains around his arms off which surprises Judgement briefly but she gets back into it as the machine moves again while she tries to attack GURPS more. 

They both pick up the speed and actually end up creating a few shock waves from their blows as they attack. GURPS uses his Saw Cleaver to block one of Judgement's clawed gauntlets and copies a move he once could use with an Augur of Ebrietas.

His arm temporarily turns into strong black eldritch tendrils for 3 seconds and he pushes Judgement back almost sending her over the side of the machine with the move. 

Judgement: "You definitely are not human... what are you?"

GURPS: "Stop the machine and I'll let you know"

Judgement: "THE PUNISHMENT WILL NOT STOP!" 

They clash some more as GURPS uses another older move he used back at the Bloodborne world as he uses his own version of "A Call Beyond" to summon multiple smaller balls of celestial energy and blast Judgement with them.

She blocks some but gets hit by the rest and yet doesn't seem tired at all despite that, she's quite resilient. 

The machine stops once again and GURPS quickly breaks more of the larger chains once more. 

Judgement: "You truly think you can break free of those shackles? You should know that hope leads to disappointment and disappointment to despair!" 

She then summons a few chains around herself and... squeezes herself a bit with them. 

Judgement: "CHAINS OF DESPAIR ARE THE MOST DELIGHTFUL!" 

The chains squeezing around her body really made her... assets stick out more

GURPS: "Did I just get a new kink?"

Meanwhile at the "stands" of the arena 

Zdrada: "You must be cursed Malinka. You just found a fellow nerd and he already may be done for."

Malina: "Knowing my luck he plays Necropolis anyways... still I don't think he's done for."

Modeus: "Maybe I should have kept him for myself after all?"

Helltaker: "Don't underestimate GURPS, I haven't seen him fight before now but I know him well enough to know he's got this handled" 

Judgement: "YES! REGRET EVERYTHING YOU'VE EVER DONE!" 

GURPS thinks to himself and after using some Insight to check something he decides to try a different approach this time. 

GURPS: "I love how you did your hair" 

Judgement: "LIEEEEEEEEEEES!! THEY WON'T SAVE YOU FROM YOUR FATE!" 

GURPS: "I also really like the claws, very cool design!"

Judgement does look almost a bit flustered now 

Judgement: "Is that so? In that case thank you! ...I guess?" 

She then leaps in the air and creates some magic looking symbol 

Judgement: "NOW LET'S GET BACK TO THE SUFFERING!" 

The machine kicks into top speed as Judgement fires a barrage of chains and this time even throws hellfire attacks into the mix, GURPS seems to be weave nation certified though as he weaves and avoids all of them while using his Saw Cleaver to deflect a few as well. 

GURPS: "I'll finish the fight with this next move"

He charges at her as she keeps trying to hit him but isn't able too, she gets annoyed at his evasiveness and fires everything she has blindly.

GURPS dodges most of them and lets a few weaker attacks hit but he keeps charging as he runs up some chains before infusing his Saw Cleaver with some arcane power and then slashing a blade of energy that cuts the remaining big chains. 

He then leaps right over Judgement and takes a page from dark souls. He channels his Arcane energy into the magic spell "Lightning Spear" and holds two yellow spears of lightning in his hands as he strikes them at Judgement and sends her crashing back into the ground, the impact even breaks the machine a little he thinks. 

Judgement gets back up breathing a bit heavy but still looking ready to go as she wipes a bit of blood from her mouth. 

Judgement: "You're quite the fighter... but I'm not done yet! NOW ANY LAST WORDS BEFORE THE REAL PAIN BEGINS?!" 

GURPS: "Only thing i regent is not seeing you sooner, those eyes you got are beautiful as well, also sweet outfit." 

Judgement: "QUIT YOUR CHEAP FLATTERIES! YOU MAKE MY JOB DIFFICULT!" 

GURPS: "Hey I'm just being honest, also sweet hips"

She actually sighs with a faint blush on her face 

Judgement: "Look I really don't want to do this but the pack has been sealed. Nothing will prevent your damnation"

She then begins to think as she looks back at GRUPS 

Judgement: "However... I could postpone your torment for now if you and your friend leave and never disturb Hell again"

GURPS: "Ehh I've already been thought a form of hell before, I got use to it."

Judgement: "Regardless of... whatever you are. Our fates are now one, I will kill you and you will suffer but it does not have to be today... so consider yourself lucky and get out of my sight!"

GURPS just stands there in silence though and does nothing yet 

Judgement: "...I SAID YOU ARE FREE TO GO! BEGONE!"

GURPS: "Wanna come with?"

Judgement: "WHAT?! YOU WANNA INVITE ME TO YOUR HAREM? DON'T BE RIDICULOUS!" 

She breathes and calms down a bit. 

Judgement: "You'd share a roof with an immortal avatar of pain blood-sworn to murder you though torture?" 

GURPS: "Oh I've dealt with worse believe me... I can't really die anyways anymore so it's all good. But even if I could still die... I wouldn't have it any other way"

Judgement: "Wait... you are serious?"

She blushes a brighter red than before 

*GLORIOUS SUCCESS* 

Judgement: "Well... seeing how far off the ritual we are already, I might as well give this a shot"

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Helltaker and GURPS were finally able to leave Hell as they arrived back in earth with their new demon girls, however something remained to discuss. 

Lucifer: "By the way... you guys never specified how this Harem thing would work, did you both want to share us as in we'd all be both of your girlfriends? Or did you want separate Harem's to yourselves?" 

The two dudes both look at each other and then get an uneasy expression on their faces. 

Helltaker: "Yeah I meant we'd share in the sense that we could both get demon girls from this trip... honestly I wanted to decide the details after because I just really wanted to get going at the time, I'd rather us both not share the exact same girls though." 

GURPS: "Yeah yeah... your like my Bro to me so if it's all the same to you I'd rather not share every girl in the sexual way... I mean we could still be friends with them all or maybe we could still be flirty and stuff with all of them even, but as far as sexual and possibly romantic related stuff we should have our own harems"

Helltaker: "Right, and no homo?"

GURPS: "No homo"

They chuckle and shake hands, that was a little inside joke they had. 

GURPS: "So like... how are we gonna do this?"

Helltaker: "let's go off either who got what girl to join or just who they want I guess?" 

In the end the Harem's became as followed:

Helltaker's Harem: Lucifer, Pandemonica, Cerberus, Zdrada(much to his pain) and Justice

GURPS Harem: Modeus, Malina, Azazel(sort of?) and Judgement

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And that's how The Helltaker and The Neo Great One took demon women from Hell. On the way back home Helltaker remembers something. 

Helltaker: "Hey GURPS? So from what I saw back in Hell you defiantly aren't human... can you tell me what you are?" 

Judgement: "Oh yeah I never got that answer from you, so what even are you GURPS? You look human but definitely are not."

GURPS: "Ahhh you all wish to know my secret?"

Everyone nods, Azazel especially seems curious and has her notepad out and ready. 

GURPS: "Ok ok, well for starters... does this world have works written by someone named H.P Lovecraft that anyone knows about? It would make this easier to explain" 

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*To be Continued*