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. Yes, some people do bleed the first time , and that bleeding is usually caused by the stretching of your hymen —a thin, delicate piece of tissue located just a couple inches inside the vagina. Need some guidance to get you started? The only way to find out is to ask them: Do they like oral sex, or would they rather leave that off the menu? Comfort with a new partner often takes time and communication, and that goes for both men and women. Whether it's your first or fiftieth time having sex, the worst thing you can do is go into it with the assumption that you know everything about what your partner wants.
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