Hole lotta pain
I am 18 years old and still a virgin. I realize there are a lot of people older then me who are still virgins, but it is still quite hard for me to handle the pressure. I do believe I am ready; I am just mostly scared of the pain.
That's because it hurts me to even put a tampon in. Is there anything I can do to prepare myself? Or at least make it hurt less when the time comes? I also have never had an orgasm, so I wonder if there's something weird about that. I often engage in other sexual activities, but never the real thing, and I usually get bored after a while because it never feels that great. Could you please tell me what is wrong with me?
The first thing I would suggest you do is to get yourself a gynecologist with whom you feel comfortable discussing your sexuality. I have found that free sexual health clinics are best equipped to deal with these matters, since part of their mandate is, of course, offering unbiased advice on sexual health concerns. A pelvic exam will reveal some possible issues, one of which may be a robust hymen. In the meantime, you might want to research something called vaginismus, a word for painful intercourse, including the inability to insert tampons without pain.
First-time sex does hurt for some (it did for me) and can continue to be painful until your vaginal canal becomes more receptive. This is not unusual. Some women who experience painful intercourse will prepare themselves with dilators, also known as stents. This is a course also followed by post-op transsexual women. You can read about it at Zen And The Art Of Post-Operative Maintenance.
As for tampon insertion, perhaps it's a simple matter of lubrication. Try greasing it up with a little water-based lube before insertion and see if that helps.
There is nothing weird about not having an orgasm yet. I was 18 before I had my first orgasm during partner sex, and I'd been having penetrative sex since I was 16 and had been fooling around with people since I was 14. There's so much going on when you first begin these kinds of adventures (am I doing it right? how do I look? is this going to hurt? why am I thinking about Catherine Bach while I'm sucking your cock? etc, etc) that it's a wonder you can relax at all.
If you haven't been masturbating, I would certainly recommend giving it a go. When I first began, I found using my hand a little intense, so I used the faucet in the bathtub. A nice steady stream of warm water can sure conjure up some agreeable feelings, let me tell you.
Or try purchasing a vibrator. A few websites that give good descriptions and reviews are venusenvy.ca, comeasyouare.com, goodforher.com and goodvibes.com. I would also recommend Heather Corinna's book S.E.X.: The All-You-Need-To-Know Progressive Sexuality Guide To Get You Through High School And College (De Capo).