I don't see that you have a problem.
Your short hair is not a permanent condition. You are just growing your hair out so stay in the wigs for another TWO years(gives you elbow room) and then take off the wigs. Have your real hair shaped and styled differently so he won't think it looks so much different than the wig.
He'll never know any different and White guys are not hung up on wigs/weaves. You don't know why he said short hair was ugly though.. could have thought that other was ugly in short hair or just running his mouth ..
I would not sweat this comment.
(If your hair was permanently short .. that would be different. Some how you would have to tell him .. and if he leaves F him. He would be shallow then and who wants to marrya guy like that?))
As far as the wig not coming off .. I've been wearing lace wigs for years now and it has never even gotten loose when I had sex. I let guys play with it too, They don't know.
I don't have any hair pullers though .. that would be a turn off if I was even wearing my own hair!!