Personally, I'd be more concerned with STDS.
Unless you've both been tested, she is on the pill, and takes it at the same time every day, using a condom isn't even a thought.
You just wear one.
If you *have* both been tested, and you want to forgo the rubber, you might want to try another method of protection from pregnancy:
- VCF: Vaginal Contraceptive Film; it's a small piece of film, that the girl folds in quarters, and inserts into her vagina up to 4 hours before sex. It's very effective, esp. when paired with the pill. (Note: Girls who are allergic to spermicide may not be able to use this)
- Sponge: Again, the female inserts into her vagina. A barrier method.
- Spermicide: Foam (most often) that can be used as a double-measure to protect against knocking her up.
- Depo-Provera / Norplant Capsules: These are for more LTR, or for girls who want to ensure no possibility of pregnancy for at least 6 months. Depo-Provera is a shot, you recieve every 6 months, and Norplant are small capsules implanted under your skin. I've heard good things, and bad things about both of these, so it's basically up to the girl if she wants to try this.
I'd recommend the VCF if you want to go without a condom, and you're both clean, and trust each other not to cheat.
But a condom is one of the few ways to protect yourself from most STD's with a reasonable level of confidence. Though it *will not* protect from Herpes, genital warts, crabs, or any other topical-skin-transferred afflictions.