We'd have to see him made up to see if he'd be passable...some people just don't have it, no matter how much you doll them up.
That being said, there are many smaller companies that shoot amateur crossdressers - they are pretty easy to find, but traveling will always be an issue.
Honestly, if he's willing to work...start up a little paysite with him - assuming you know what your doing in the online adult business, it's not terribly hard...drive your own traffic to it (unless you have none in this niche, then it'll take some work to build new traffic and/or buy traffic), and your not paying anything for content...so the only thing to lose is time/energy, which is better than most paysite startups! Give it a year...if it works, it works...then toss it in an affiliate program and rinse/repeat - if it doesn't...well at least you didn't break the bank!
