“I was wondering if you could give me a little advice. When i have sex with my boyfriend, it feels great at first, but it quickly starts to hurt. We have tried different styles, different condoms, and even lube. I feel horrible because he never gets a chance to come because im too sore before long and we have to stop. I dont know if size is the problem. Is there something we are doing wrong, or should i just go see a doctor? Thanks in advance for taking the time to at least read this.“
I guess what might really give you a clue as to what the problem could be is the kind of soreness you’re experiencing: if you’re feeling chafed I would suggest more lube, if you’re feeling bruised I would suggest you being on top to control how rough things get. The problem shouldn’t lie in the size differences because you’re stretchy (see THIS post), but to be stretchy you also need to feel relaxed. Perhaps you just need more time or more foreplay before you two start the actual penetration part of the sexing.
If you’re feeling bad about you two not being able to orgasm while having sex, there IS something you can do about that at least. When sex starts to feel uncomfortable, stop and switch to something else: oral sex or manual (mutual masturbation). This way things won’t have to end with either of you feeling too disappointed because you can still finish each other off and have a sensual experience.