My girlfriend is the relationship type. She's been in relationships before and has had sex before. Overall, she comes off as the type of girl that has sex with a boyfriend to enhance the relationship. (Like many girls)

None of her ex bfs get to me so I feel pretty normal in that regard.

However, one of her sexual partners was a guy that told her the plan was to be friends with benefits. In fact, he told her that his plan was to date someone else, and the basis of their hookup was knowing that beforehand. I have the most difficult time picturing her saying yes to it even once, let alone on multiple occasions. This makes me jealous because I often feel like she never would have done that with me, making me sexually inferior. To make things worse, there was a long period where she described him as a gentlemen. Keep in mind, she never had intention of dating him.

In fact, when we started falling in love, he asked her if she could paint him something (she was an art major) that meant a lot to him. She agreed to do it, but ended up not doing it. Even though she didn't do it, it bothers me that when she was falling in love with me, she even considered the possibility of taking an entire day, painting him something. It makes me feel like I wasn't very moving.

She describes the whole experience as something she was trying to convince herself was respectable. I really want to believe her, but my insecure inner self struggles with it. My insecurities make me feel like the whole reason why she struggled to view him as an asshole was because she got something out of it (i.e. an ugly guy would have gotten a slap in the face, but a hot guy gets called a gentlemen because his attractiveness makes the whole experience feel more like a fair trade).

A bit about myself: I was bullied in high school for my looks. I don't want to go into it, but just know that it was fairly harsh. This is my first relationship and sexual partner.

How do I learn to get past the whole painting? I try telling myself that she decided not to do it, but it bothers me that I look back on the root of our relationship and picture her telling an old hookup that she would paint him something. I know with 100% certainty, I would not have responded positive to any other girl.

Please realize that I am here for help. If I seem very insecure, it's mostly because my past experiences with women have never made me feel hot. My gf and I have talked about this whole thing, and to anyone who thinks I am some as$hole projecting my insecurities onto her, know that I have talked about this with her in a way that focuses on my personal insecurity issues.

I would appreciate any advice. Thanks in advance.