Let's look at John's fantasies.

John has all of the time in the world to find his 'soul mate' but right now John could use just a little bit of fun. He spent almost all of his teenage years doing nothing but working on me. He didn't get to have the fun that most people his age had. No fun parties, no horrible dates, not even a single moment where he could brag. Maybe the best choice is to let him go a little wild first. John already has the money, why not let him cross a few fantasies off his bucket list first? Let's see what gets John's motor running. To the porn folder we go!

Wow...there's a lot of choices here. Luckily, it's mostly simple stuff. Different races and a little BDSM mostly. Then again, the Taboo stuff seems to be a little...harder but I definitely have an in with the people who could make this happen. The wild sister Jenny McCullen would probably be willing to do some of this (if only to cross some things off her own bucket list). A nudge in the right direction and this black haired beauty would be willing to do anything...hopefully.

Of course, there's still a lot of options to choose from.