Reginald Bartholamew Winchester (the 3rd)

You are the third (as it turns out) Reginald Bartholomew Winchester in the Winchester family, of rifle and pistol fame.

Ever since World War I your family has been cursed with wealth. How would that be a curse you ask? Kidnappings, seductions with the purpose of getting a baby to collect child-support on, false marriages for alimony, frivolous lawsuits, scams, fake friends, the list goes on. All the problems of having a great fortune are your family's to bear effectively constantly, but it comes with a powerful but strange luck and talent for making money and also surviving these events unscathed. The theory of how this works is that your family bears the ****-curse of everyone ever killed with a "Winchester" brand weapon, but also has the power of binding their ghosts to serve them through those curses. And your Great Grandfather developed a plan to fix it through thaumaturgical magic that is still being used for the family. Whenever a baby is born to the main branch of the Winchesters they are born in a massive Olympic Swimming Pool sized birthing basin in the sub-sub-basement of your grandfather's mansion: one inscribed with various runes and symbols in carved glazed tile. That basin places one of the Winchester ghosts into their body as their soul. You were not so bound, but you still have Winchester blood, so are still affected by the family's mixed-curse, and can be part of fixing it. You also have been kidnapped a dozen times already in your life, have the fake friends, and all of that.

Your father was "merely" upper middle class, working as a financial advisor. You've realized, however, that he was doing his utmost to sabotage his clients so he wouldn't wind up on some kind of "Best financial advisors of our age!" list from Forbes or something. Now that you are back with the main Winchester clan, you have begun trading stocks, bonds, and futures like some expert with 20 years experience but only drawing on the notes you were able to crib from your dad over the years before he died. Your personal fortune is already heading into "Late-1800s Robber Barron" territory, and stopping isn't on the agenda just yet.

You've always wanted to have kids, impregnation is a big fetish of yours, but you also wanted to be responsible and wait till you were 25 or so with a stable portfolio and such. Now with the vast family estates seeing to the children's welfare, you are somewhat apprehensive, but nerving yourself up to start: you already have a specific target in mind, in fact. With your generously endowed member and sexual skills garnered from training in yoga and porn film actor's courses, you have little doubt that you can satisfy her once you're in bed. The real question is; can you seduce her in the first place...?