My boyfriend and I have been dating for almost seven months tomorrow... Even though it's not a super important "anniversary" we've been through a lot and I wanted to do something special for him... But we're both broke college students so for as long as we've been dating he's told me he loves anal and wishes that we could do it... Well it's always hurt so bad and I never end up doing it for him. He's never pressured be about it too much he just occasionally ask if we can try but it never works out. I'd really like to be able to do it for him tomorrow. Do y'all have my tips to make it feel better? I know a lot of women actually like it but it always hurts me. Is there a solution?