"What do you guys think? Should I go ahead and ask him?"

Transference is not a negative. It allows us to work through old relationship wounds in a safe, supportive, new, therapeutic relationship. So, I'm not sure if you're referring to erotic transference, and you're afraid he would not trust your motives, which would be sad, but I encourage you to ask for the hug. I hope, worst case scenario, that he's willing to be supportive and comforting in some way, even if he says no to the hug itself. But... it is possible he'll say yes. I hope so! Good luck!