How can I feminize by boyfriend?
 

I would really like my boyfriend to be a little more girly, but I don't think he would like that idea. I've hinted at it before and he expressed no interest. So I'm kind of considering a way I could maybe manipulate him into it. I know he'd be ok with it once he got used to it.

Is there any kind of way that I could get him to gradually get used to the idea of being a girl for me? He's generally pretty timid and I usually get my way, so I probably have a shot at forcing him to dress up for me, but it'd be just as well if I could kind of manipulate the situation to make him somehow think it was his idea. His personality is not feminine at all though, so might be kind of hard to convince him it was his idea lol. I really, really want to do something though, I just have no idea where to start and what to do.

Please, no moral judgments, just advise. And I know that "just talk to him about it" is probably the answer I'll get most, but I've already talked to him about it and I don't think he wants it.

If you dont think he wants it, then why are you trying to force him to do it?

You could try making a bet with him, the loser having to do the winners wish. Assuming you make the right bet, and you win, then you could challenge him to dress up. Maybe take it easy and just put him in women's knickers to start with and build up from there.

Of course, if you lose the bet, then it could backfire on you...

I had the same idea as owlart with the starting him out with just weraing the underwear first. That way it's not to public. You could also ease him in by put some makeup on him. But don't make it TOO noticeable, maybe just some blush or a little eye liner. And good luck with feminizing him! :D

You could try to tease him into it. Seem like it draws you closer to him when he does it (which from the sound of your post, it does). He'll (eventually) figure out that connection and will chose to do it of his own will.

u could tell him that u think that u might be turning into a lesbian and u wish that he was just a little more feminine (under your breath of course but loud enough he can hear or he might just ask to watch when ur with a lesbian lol) (im giving advice because it would turn me on so much if my girlfriend was trying to do this to me lol)