I am a 20 year old female. I have been sexually active since I was 17. Every time I have sex whether I was in a relationship with them or not having sex hurt. When we first start to have sex it feels good, but after a few minutes it starts to hurt, feeling like the penis is hitting a wall. I can't last for more than around 5 minutes or the sex feels like intense pain. Also I have never has an orgasm while having sex, I just do not feel aroused in the same way while having sex, like I do when my clit is being played with. People tell me I just do not have sex often enough so I am not "stretched out" or "used to it" but it does not feel good to me at all, except for the first minute or 2. I don't understand why I don't enjoy sex like the rest of the human population.

My early childhood consisted of Legos and Hot Wheels. In junior high, I listened to more metal than pop, wore hoodies and Vans shoes, black nail polish and eyeliner. Nowadays, I've been getting more interested in piercings and tattoos. I've never felt like a girl for the most part, but I've never considered getting some sort of sex change or anything either. I've only been attracted to guys, as friends and romantically. Because of my hardcore tomboyishness, guys never ask me out/respond favorably when I flirt. In high school, everyone assumed I was a lesbian. I said no, since I don't like girls.

Since I feel more like a guy, but like guys, would that make me transgendered somehow?

So there is this guy that I really really like. I don't know how to get to him without having to put myself out there. He says he cares but then when we are with our friends he won't even talk to me. When we are alone he is always by me but wants to do anything other than talk, it seems like he only wants sex. We messed around once but I don't know what to do now. Am I stupid for falling in love with him and pretty much doing anything so that he will stay closer to me?