MRW I star in a DnD Villain's campaign, and I win at being most evil.
Well, it was actually Pathfinder, but whatever. A friend had a marvelous idea of starting a new campaign with us all as villains instead of heroes, serving in the army under a tyrannical empire ruled by a crazy orc. We often play with a Horrible min/max gamer, and from the start they were trouble as an Antipaladin. After learning about their backstory - having been raped and tortured in their youth, a common theme with this particular player (yeuck) - I set my evil plans in motion.
I was a Dhampir Monk. Lawful evil, naturally, specializing in Crane style. Not a fucking thing could hit me once we got into magical items. And so, along with a party of other diverse powerful lunatics, we were tasked with being the tip of the spear against a goody-good theocracy of Abadar that thought invading us was a good idea. We fucked a lot of things up, for sure.
Ah, but that Antipaladin caused us a world of grief and unusual setbacks. She was undoubtedly going to betray us (I mean, we were all going to betray each other eventually, but we all knew they'd foul our plans before we got the chance). With a sizeable bribe, the other monk in our party used their abilities, while the Antipaladin was asleep, to remove a majority of their defensive powers without their knowing, with rolls and notes handed to the DM. Then, I offered them some wine we recovered from burning down one of the enemy forts. It was actually a very powerful love potion, and they failed their save.
So now this antipaladin was in love in that sadomasochist way with my character, and we rolled with it. Eventually near the end of the campaign we decided to overthrow that crazy Orc emperor and institute ourselves as the ruling body of the empire.
On the eve before the final battle, I revealed to this character that mine was the one that raped and tortured her, in my dhampir's youth before taking their monkly vows. It was spun to embolden the antipaladin, saying that I was the one that forged her into such a great warrior, but it really just added insult to injury how she was now a thrall. It was a shocking revelation and dialogue, and the DM allowed the guy to make one more save roll against the love-potions effects. He succeeded, but did nothing.
Once the final battle was done with and we killed the emperor, this fine antipaladin finally turned on me and tried to kill my horrible dhampir. She could not hit me once. And man, the guy rolled his best to try to kill me. I swear there were a couple of fudged rolls, but it wasn't good enough. Eventually they called on a devil that had been our benefactor for a while to end this and kill me, in return they would serve this devil. I convinced the devil behind-scenes much earlier in the game that I would sell my soul if I became Emperor myself, and negotiated a proper contract. Hah! So instead, the devil erased the antipaladin's memory, effectively 'killing' me in her mind, and proceeded to make her his slave. I became Emperor while the rest of the party started their own cults and/or rebellions elsewhere.
TL;DR~ I toyed with one of the players from start to finish, and betrayed the rest of the party well before they got the chance to betray me. Evil Overlord bucket-list achieved.