I have seen it, and I am concerned!

You should go very slow, make you feel comfortable, not push or insert his penis all the way.

First times suck anyway...Maybe you should do a bit of foreplaying before actual penetration took place and you should make sure there is enough lubrication, either your natural that shows upon excitement or you should get some water-based lube to make things more comfortable.

You should not overdo it with lube. Take it slow and enjoy! Good luck!

Okay- now for a more detailed question: Is it possible that he won't fit? This is humiliating... but I was so worried that he wouldn't fit that I tried putting plastic wrap around a banana, putting lotion on it, and fitting it into my vagina. It didn't work. I tried, but couldn't get the darn thing in there. The sad part about this experiment is that the banana is the same size, if not smaller, than my boyfriend's penis is in diameter. Now... people have said, "Well a baby can fit through it--" but seriously. Having a baby HURTS. Will sex with this man ever be pleasant for me, or will it just ridiculously hurt the first couple of times that we have sex?

I can't say....you won't know until you try. It may hurt at first but get used to it later.