Matt,
What do you have to lose? Honestly.. Instead, consider what you stand to gain.
Why not move her and Josh in at around the same time? You can then cozy up with the two of them, give them some wine to drink, possibly watch one of Goodrum's sensual selections and then, when everyone gets tired and sluggish, start having a 3-some (you don't need to touch Josh, don't go that far, but have your way with her). Both can penetrate from opposite ends and in a show of absolute class and grace consider high five-ing each other while "on the inside". Consider having Everybody Wants To Live Forever by Michael Small playing in the background. Also, make sure to film this masterpiece and post it on GetBig (at the "More Explicit Sex BoardTM"). This would involve the 3 of you becoming one, a most unholy of trinities, but indeed a GetBig classic.
You do this and you stand to become part of the GetBig elite. This act would never be forgotten, nor would the heroes who take part in it. Will your actions echo across the centuries or will you simply cower away in the corner sulking and aggressively pounding your meat while Josh devastates this woman with his Sasquatchewan ways?
Your move chief..
"1"