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How should one evil villain go about wooing another evil villainess?
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How should one evil villain go about wooing another evil villainess?

>Show her your strength, challenge her and her army to a battle and be victorious
>Swear your body and soul to her, pledge your army to hers
>Recommend that uniting your forces as one would make you unstoppable
>Offer her the heroes head or the good kingdom on a plate
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>>45879250
Same way Rita Repulsa and Lord Zed got together.

A make over and date rape drugs.
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>>45879250

Beat her armies, destroy her villainous lair, undo her plans and hatefuck her. She's BOUND to become your deranged evil love-interest after that.
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>>45879250
Have a shared goal; if she wants to rule the Kingdom, you want the current King dead. Her taking over is a matter of no consequence.

Work towards your goal. Don't work for her, don't even actively work with her. Just accomplish your goal that coincidentally serves to hasten her own success. She will come to you.

And that's when you decide yeah, you don't mind loaning her some troops, sharing some info and taking out the occasional VIP. But you never bend the knee. You just carry on carrying on, and generally don't cause her problems.

Eventually this constant string of being totally on her side but neither beneath her nor competing for her will drive her crazy. She'll either be driven to an insatiable need to kill you or a similar need to fuck you. It is possible she might have both.

If she decides she *only* wants you dead, have your sleeper agents in her army fuck her forces over and then leave the country for a few years. When you come back she'll be ready for another go and you can see if anything's changed.
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>>45879250
Flowers, idiot.

Poisonous flowers.
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>>45879250
Using the most unholy and abominable methods:
A simple romantic date and walk on the beach with a rape after in a slow and loving missionary position
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>>45879335
>>45879379
These.
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>>45879250
Give her the D
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>>45879424
You forgot [spoilers] while holding hands [/spoilers]
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>>45879250
I don't know... What about asking her out on a date?

Second date, you get her flowers.

Third date, you empty out the local tavern by force. Just you, her and catering.

Then you take her out on strolls through the battlefield.

When you've got the PCs on the gallows, you propose.

Nothing says wedding like a noose around their necks and a ring on her finger.
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>>45879630
Just remember: don't leave her hanging.

*rattle rattle rattle*
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>>45879250

>"Want to go get a bite to eat?"
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>>45879335
>Beat her armies, destroy her villainous lair, undo her plans and hatefuck her. She's BOUND to become your deranged evil love-interest after that.
This. Women don't respond well to weakness. They're attracted to power like flies to shit. I cannot possibly imagine that a villainous woman would be any other way.

Professing your life or swearing yourself to her or trying to prove yourself would only open up yourself for exploitation.
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>>45879747

Forgot pic
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>>45879747
this. take her someplace nice.

Hell, if you've got the money, take her out to sigil. you're both busy people, so i'd suggest getting a pair of simulacrums made before you go, so your legions of doom don't know that you've left.

thing is, she's a sorceress so she can go to sigil any time she wants. You have to break into the basement of a church to the lady of pain on the material plane which just split in half like a great paring knife rent it in twain. There's a key with a planeshifting enchantment. It takes you a while to get used to.

after defeating the unicorn mounted elvish virgin attempted bacchanal, you ask the dread sorceress if she wants to have dinner. You can't see her eyes behind the black helm of ts'za, but her dark blue lips quirk in a grin. You intentionally fail a series of will saves as she casts half a dozen divination spells, her immense will moving through your body to your dark soul.

"sounds good. You've prepared simacrulums i see. And the gate?"

you swallow, and turn the key in midair.

The thing you didn't really realize about plane shift, it often sends you quite far away from your intended destination. she realizes that you're lost, and grabs your hand, teleporting you across sigil's ring to the dryad's cafe.

dinner starts awkward. She's a powerful sorceress, and you failed out of wizard school and became a bandit. Sure, you can use magical devices, but it's definitely not the same. She's talking about wielding forces that you're having trouble comprehending, because she's using these obscure metaphors from plays you haven't seen. you mention that you failed out of wizard school, and she asks which one. Turns out you failed out of the same wizard school, she's just a few years older than you and had more raw magical talent. She offers to show you some things... sometime.

[cont'd]
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>>45879250

well there once was this short story about a Dark Eldar Lord. I think it was from the Book "Fear the Xenos" and it as called A Present for Lady Baeda".
Book had only two good storys though, this wa sone of them.

In this short-story this old dark eldar lord tries to woe this lady (Baeda) but everyone tries. first he kills all his Rivals and brings her their faces. She is mildly impressed. Then he tries to give her a whhole world of the Imperium but she dos not want to see him. then he goes to a necron krypt and wants to remove a stone to make aring out of it. The most precious material...
But by doing so his whole cabal dies, even his 'beloved' daughter.
So he goes to his Lady, in a rage and kills her guards only to stand before her and cry for he has tried to give her everything and has lost all he had. And she... kisses him. She loves him now because the pain he feels, and thus the pain she enjoys is the most wunderfull thin imaginable for her. So together they form a new alliance.

Hopefully this gives you insight OP
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>>45879976
she leans over the table and puts one of her boiling hot hands on yours, whispering a crude joke about salamander's and their polearms. You're trying to meet her eyes, when the helmet becomes transparent. You can still see the outlines and the structure of the helmet, but now you can see her face as well. Her mouth is an unfeeling line, but her eyes are locked on yours and have a glint which might be more actual fire than mysterious mischief.

she leans back as the coffee arrives. Blue flames jump from the black drink. the dryad waitress places a bucket of potions of fire resistance on the table. the dread sorceress' eyes are actually burning red now, and her eyebrows quirk. She takes a sip, some of the blue fire dances along her cheek.

You didn't get to be the lieutenant of the sorceress' army by not taking risks. Carefully, you peel open one of the potions of fire resistance, and pour the white, milky liquid into the coffee. You smile as you take the sip.

At first, it feels exactly like your face is being melted by dragonfire. you died that way once. not too fun. But after barely a moment of nearly screaming in agony, you feel the warm flutter which fire becomes when it doesn't hurt anymore.

You hold the coffee and drink in the aroma. The sorceress catches your eye, and mimics rubbing her eyebrow. you reach for it, and your whole eyebrow is gone. You start laughing. She draws you a new eyebrow with arcane mark.

"Glows in the dark too, when i want it too. Hey, potions of fire resistance last for thirty minutes, want to get out of here?"

You're taken aback, but you don't think she cares that you're pretending to play it cool. She opens a gate into her mystical mansion.

The entire building is constructed magically, but it pretends to be constructed by the honest work of a toiling laborer. She leads you down the hallway, when you hear the commotion from ahead.
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>>45880169
>>45880169

as a human you don't have low light vision, but you've stacked your listen check. You hear something from up ahead. She barely has any ranks in her perception skills and would have missed it if you hadn't stopped her. You lead the way towards the bedroom, and she's casting buffs like bulls strength, cat's grace, bears endurance, ironskin, invisibility. The door is cracked open, so you creep in while the dread sorceress waits behind.

On the bed are two figures. Your simacrulums. She is riding him. Her head is arced back, but when she lowers it and opens her eyes, her eyes are glowing that same red, and they lock on you. she whispers some words, and within seconds she has you dominated, a puppet to her whim.

You try to shout a warning to the dread sorceress, but you're fucking her simulacrums mouth too hard to say anything. Her mouth is like sticking your fire resistant dick in a campfire. You hear a whisper from behind you, and suddenly you're choking the clone. the copy of you stands and tries to hit you, but he has zero buffs and you're in your fancy-dress adventuring garb and made of iron. It takes ten rounds for the clone sorceress to choke to death, at which time she immediately melts into a puddle of snow. You feel the mental control snap as she dies, and suddenly you're free to have your own will again. The sorceress runs her nails over your iron pecs.

"She dominated you, so i dominated her. I made her order you to choke her to death."

you cup her cheek and whisper "that is so fucked up" as you kiss her.

Soon, she's set up a psychic network between you and your clone, so that anything he feels you feel too, and vice versa. She's on her knees with your iron cock in her pussy and her pussy feels like a blast furnace on your fire resistant cock. and she's sucking off your clone while your iron fingers trace her back, and she didn't cast fire resistance on him, so he's turning to slush as he cums.
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>>45880328
She cums, and your clone cums. you feel his absolute bliss as his mind slips into the void, but with your bears endurance and iron skin are still hard as iron. You keep fucking her, pushing her head into the blankets.

Right as she was cumming the second time, when all the buff spells wore off at once. Your dick burned off even as you came inside her. She got someone to cast regenerate, but it was way worse than the dragon burning your face off.

Now, it's three months later, and she's had to build another simulacrum. This time bound to her will directly. Not just because we wanted a vacation, but because she's worried that high levels of transmutation might have on her. her and the baby.
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>>45879250
Its already been mentioned, but read "Mistress Baeda's Gift".

Evil powerful villain tries giving his love-interest villainess EVERYTHING. Outlandish gift, after gift. It all fails.

Finally he expends everything he has trying to woo her. His soldiers, his daughter (who was the heir), money, wealth, planets, slaves etc.

Then as he is on his knees in front of her waiting for death, she kisses him. And says she yields to him fully.

She says " You've given me the greatest gift imaginable: Your suffering".

She literally undresses him then and there, in front of her guards, and "cements their partnership in a torrent of public love-making"
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>>45880530
Fucking Dark Eldar, man.
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>>45879312
>>45879335
These in one combination or another.

Just smack a hoe up.
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>>45879250

Remind her that she is also a flesh and blood (Insert Race) women and she has needs. Be sweet, but a bit of a dick too, can't look like a pansy. Give her something she likes, be it wine, some kind of food or flowers... That or join her in some friendly act of evil, take a day off from the evil plan and just go pillaging, like the good ol' days when you were both still just minor nuisances instead of Conquering Evils.

Then maybe end the date with a bonfire... a village sized bonfire, but a bonfire. See if you can get her to lower her guard enough that you can hold her hand without thinking your gonna stab her. Also gotta keep your own blade within reach, never know man. See if you can get that kiss and work from their. Maybe you might not be able to get into a full relationship with all that's going on in your respective domains, but maybe you can have something more if you both ever decided to team up and conquer the world together.

Oh also pledge to avenge her Death if by some chance she is defeated by adventures. Take out their families and friends and then pick em off one by one while dealing with the one who did the killing blow last.

Then ENDLESS torture.

Cause you might also be in constant pain now... So yeah that's what I'd do.
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>>45879250
Find out what she likes and sing her a power ballad.
https://www.youtube.com/watch?v=FJG3UEkjwlU
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