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Well, okay . . . . I've only had gay three-ways so take this for what it's worth, but the single tool I've always found the most useful when dealing with a new player is simply asking in a friendly, non-threatening or non-aggressive way what he thinks he'd like to do. It's funny that communication seems harder than actually being physically intimate with someone, but it's a common problem. He might be nervous about voicing what he finds hot, but he'll probably also sense you're new to this and that might help. Your girlfriend might be able to help in this area as well. I don't know if after you get into it with her that she telling you guys to play is the best approach . . . he might feel a little on the spot in that situation.
Going with the flow is great, but it's nice to at least have an idea of the other person's boundries.
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