Heather Corinna replies:
That doesn't mean your boyfriend is lying, he just may not know doesn't know any better, since he probably hasn't been on the receiving end of anal sex or any kind of intercourse before, or may not have performed it on anyone else before either.
Your anal tissue and the anatomy of your anus and rectum, for starters, are very different from your vaginal tissue and your vagina. It can't lubricate itself, and it's more prone to small abrasions and fissures. So, to begin with, you are more susceptible to STIs and infections via anal intercourse, and more likely to experience pain or discomfort, and you certainly DO need a condom. In fact, if he's going on about not needing a condom, that's an arena where I would have an eye out for someone fibbing.
In addition, I don't usually recommend anal intercourse for teens for a myriad of reasons, one of which is that in my experience, I haven't seen that most younger partners have the big-time patience or level of communication skills with their partners that is really required to make it anything less than pretty uncomfortable. Anal penetration by a penis is not a very good way to start, for example. If you want to experiment with anal play, try just one gloved and lubricated finger first -- and not with baby oil, with lubricant like KY Jelly. If you don't like that feeling, or that hurts, a penis is not going to be pleasant either. And any sexual activity should be about feeling good -- not just about avoiding pain. Anal play also involves plenty of communication -- just like other kinds of sex -- where partners ask each other questions, share feedback, and are responsive and gradual. Is your boyfriend up to that? If he's not, then the simple answer is not only that yes, it will probably hurt a good deal -- especially with a whole penis, and probably more than vaginal intercourse will -- and this isn't such a great idea right now.
As far as whether or not you'll still be a virgin, it depends on what you think virginity is. There is no clinical definition of virginity -- it's a cultural idea, not a medical state.
My advice? Stick to the basics for now, and if you want to try some anal play, try it yourself first, with your own two hands. If you like that? Then you can talk about anal play with your partner and work into it gradually, as it feels good at whatever level or type of play works for you. And if the sex you're having is getting to be all about what can be done to avoid practicaing safer sex, nip that in the bud right now: for your health and that of your partners, you want to start your sex life walking in with safer sex practices as a given, not a negotiable.