Open to suggestions and refinements on my background ideas. I'd like to lay this out and see what people think.

Pardon the possibly cliche romance (sub)plot.

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I've DM'ed D&D since I was a small kid. I introduced my roommates to old 2nd Edition and we have been slogging through the Temple of Elemental Evil for months.

But we should finish soon and it looks like we'll be doing 5th Edition and I'll get to play a character for probably the first time ever!

We are encouraged by the new DM to come up with character back stories and he seems open to morphing the world around the characters. He's stated that his campaign will likely be short and then we can see where our characters and the growing plot take us from there.

Our location will be an island (some pirate stuff here) with 2 factions controlling the northern and southern cities, but there is room for us to have come from any manner of other land beyond. The time period is wide open pre-renaissance.

Our party will all be various Evil alignments. We will have a Battle Master with a glaive (I'm envisioning a Guan Yu type character), a turned-evil Oathbreaker Paladin (who starts the campaign before breaking their oath), a Dragonborn (black dragon, acid) Monk of the Four Elements, and one other undetermined character.

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My Character

Bard
Half Elf probably for Cha bonus, otherwise Human
Chaotic Evil
College of Valor
Charlatan
Instruments: (Electric) Lute?, Kazoo?/Harmonica?, Miniature Harpsichord?, Bagpipes?

The character did not start out with an Evil alignment, but grew to it over time as his story unfolded. Evil in this case will probably mostly mean the character will do anything to accomplish their goals. This need not be kill, maim and mutilate, but for this character will likely more often be manipulate, swindle and con.

Origin

Regardless of his original place of birth the character found himself trying to be an entertainer in a great city reminiscent of ancient Babylon crossed with the Islamic Golden Age of learning.
One day he saw a vision of loveliness (and riches) who, after much struggle, he was able to visit, charm, and who in time became his patron. This was an incredible time (true love and money and all that), but alas was not to continue.

The city and other cities in the area were conquered by a demon worshipping group from nearby lands led by Cambions (half-breed spawn of humans and fiends). This new empire I envisioned as a variation on the Assyrian empire and their worship of Ashur. One of or the King of these people was a greater demon from the Abyss who demanded the most beautiful women of the city be brought to him to be taken back to the Abyss as slaves.

As my patron was brought before the fiend she managed to use some sort of family heirloom, a magic item of some kind, to encase herself (and perhaps others?) in a crystaline cocoon. Enraged, the fiend struck the crystal, but it was seemingly unharmed. She was taken to the Abyss. My character was the only one who noticed a tiny shard of crystal that had cracked off the cocoon when it was struck. He pocketed it and managed to flee the further pillaging and destruction of the city.

Months later as he stroked the surface of the crystal in dark grief he thought he heard a soft voice in his mind. The crystal somehow had created a mental link to his patron that allowed a tenuous mental connection to exist. This connection seems to be stronger in some places and weaker in others.

So he travels to seek out the places it is strongest in hopes there is a creature or gate that can lead him to the Abyss. He also looks to integrate himself into a powerful group that might be able to weather the horrors of the Abyss. He realizes that he was helpless alone and needs support of likely some powerful, possibly brutal "friends" to accomplish his goals.

Unfortunately, the mental connection to his lover, who is frozen in a moment of terror and surrounded by the essence of the Abyss is slowly driving him a bit mad. He is terrified that the crystal will fail or the small mar in its surface will be noted. He can sometimes be seen stroking the crystal or whispering to it by any party members, but is quick to hide it away and pretend a cheery demeanor if confronted.

The character acts somewhat erratically depending on the tenor and strength of these mental messages. He has turned to being a con man, a cheat, or a charmer. Whatever it takes to make enough money to keep on the move or make progress in finding a way into the Abyss. He is willing to try different things, such as blood rituals or demon summoning and if all else fails perhaps even send his soul to the Abyss upon his death. Thus far however, his chase has been fruitless.

The character prays to a variety of gods as serve his purposes to various lengths of sincerity. Mostly these are Chaotic Evil gods of war (when singing in combat), or gods of trickery or monetary gain (when not in combat).

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I'm stuck between wanting to be serious and doing amusing things, like having my Soothing Song (for helping party members rest) be played on my Kazoo. Or whipping out a miniature (child's) Harpsichord or Bagpipes in the midst of combat.