Actually, it's a great idea for all sex-having people. 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. And don't worry, you don't have to bring up this convo the moment you match with someone on Tinder, but you should bring it up before you take that trip to pound town, says Engle. Tammelleo says this is especially important the first time you have sex with a new partner. TL;DR: Everyone has pre-sex jitters no matter how much chill they seem to have, and honestly, you should totally embrace the awkwardness. Not only does asking questions show your partner that you care, but it may also encourage them to do the same—making the whole experience better for everyone. How to Have Multiple Orgasms. 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.