OK, update.... I called my friend with the female who has already had a litter, and miracle of all miracles, she is in heat right now. We talked to the vet and he said it would be fine to try to breed her again as it has been 8 months since she had her last litter. She brought her over last night and within 15 minutes my little boy became a man!!
She is bringing her by again tonite for one more go round. I did think that this might perk his interest in Libby, but it hasn't. He does sniff her and lick her and then he goes and gets his rope toy and brings it to her to play.... So this is what I am thinking for her next heat cycle, when she comes into heat I will take her to my mom's house for the first 6 or 7 days and then when she seems receptive bring her home for a couple hours and then take her away again. I am thinking that maybe they are just to familiar with each other or something so if I remove her for a few days then he might be more excited when he sees her. I will also look around for a back-up stud just in case but I really don't want to use one if I don't have to. I guess there is still a chance they will hook up before her cycle is done, but I don't have my hopes up. I am actually THRILLED that he figured it out on the other female, at least I know he's not gay