Once again: lube is your new BFF. Tammelleo says this is especially important the first time you have sex with a new partner. Simple questions like, "How does that feel? No amount of slumber party gossip about blow jobs and giving massive hickeys can prepare you for what your partner is actually gonna be into. Another benefit of using a water - or silicone-based lube with a condom avoid oil-based lube, which can degrade latex is that less friction means the condom is less likely to tear. Tammelleo adds that "hundreds of women" have told her that, when they had penetrative sex for the first time, it felt like their partner was "hitting a brick wall. No new partner deserves a full report of your sexual history. Need some guidance to get you started? But more than 50 percent of people don't bleed their first time, because the hymen can be stretched during regular, non-sex activities like jumping on a trampoline, riding a bike, or running around.