Therein lies the problem. You know that you have issues to deal with yourself, but what I don't think you realize is that they are not hers to bear at all. You come with the disclaimer that you know that these demons in your head need to be dealt with but in the next moment you are back to focusing on how you can "help" her with her problem. Here's what I see. you say that you are trying to help her but what's the motivation in that? YOUR satisfaction and soothing of your insecurities. How is this about her having a challenge in life? It isn't. Is she coming to you, saying "I want to have sex now, but can't because of _______, please help me!" ? no. You are thinking of your need for sex from her and this is the motivation behind it. You are trying to "help" her to help YOU. What does she get out of it? You may say sex but have you asked her if that's what she wants right now? Because if she doesn't and you haven't asked, you're no better than her previous bf who coerced her. Just in a more roundabout way that's a bit deceitful.

i realize you're not overtly being deceitful to us or to her, don't get me wrong, I think in essence, you are deceiving yourself, fooling yourself into thinking you're trying to be a help to her.. but I'm telling you the source is that YOU get something out of it. It leaves her out of the equation and tries to fix her problem so you can have sex with her. I don't hear your concern about her needs whatsoever and this concerns me.

Who friggin cares? 99% chance any woman you meet at your age has has previous sexual experiences. How can you be jealous of her experience when it happened before you existed in her life? Why be jealous of guys that had her sexually before you did while you had no sex? it's not a FRIGGIN COMPETITION. The one that gets any particular girl FIRST is not a winner of any kind, and no one gets a trophy for that. The one that takes care of the girl, makes her happy and loves her wins, and unfortunately we lack trophies for that all the same.

You simply must break free from this monster of jealousy and trust me I know what it's like but it's just not going to make you a good bf. Forget about her issues. Forget about what she may have done in the past. Please just take care of your insecurities and jealousy and from there, things will go much smoother.

I understand, but sorry is a good start. DO SOMETHING about it. Get a counselor, talk about it to them and work on YOU. don't sit around pitying yourself or even her for the problems. If you love this girl you should want to be a better man.