Does a male lone wolf need permission to breed with a pack female?

Yes, any lone wolf requires permission from CMs, as well as any relevant PMs. In the case of wolves from two different packs, all relevant PMs just give permission.

Edited to add this quote from a thread posted in the PM HQ:

Hey PMs, just a reminder:

Lone Wolves may not breed without seeking permission from the admins with a compelling reason

Source: http://wolf-rpg.com/showthread.php?tid=13171

Even if one party belongs to a pack, the loner still needs a green light from the admins. So if you get approached regarding permission for one of your pack wolves + a loner to breed, please verify that they've gotten permission from us before making your own call.

Thank you!