I think you shouldn't put so much pressure on yourself. And don't worry about what is weird or not weird you know? There's always a way to get to the root of why we feel and do the the things that we do. If you don't want to cry anymore after masturbating maybe change your mental approach and just say hey, that felt good, and it's gonna be amazing when someone is here with me. That'll probably make you smile instead of cry.

I'm not sure if this would help at all, but have a teddy bear or some sort of life sized stuffed animal next to you while you... work your magic. Than afterwards you might not feel so alone.

I had issues with self pleasure after leaving an abusive relationship and had the the same issues as you what helped me at the time was looking at it as self care for me and not necessarily an act that a partner needed to be there for. Self pleasure is a normal part of being human and can have alot of positives for your mind and body .. don't put pressure on yourself and if you were to cry afterwards with a partner (I did) I would hope they wouldn't be judgemental otherwise I would see that person as not right for me.