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This is a congenital condition meaning that you are born with it that is fairly common in men. So, doing any sexual activity you choose slowly and with intention can help you avoid injury, as can communicating what you're feeling, needing, and wanting to your partner. If that's the case, or even if you do feel like you're familiar, I'd suggest taking some time to get to know them, or know them better. Our bodies are designed to tell us what they need and want by how something feels to us, and what they don't need and want, so you really can trust your gut on this one, and go with what is comfortable, not-painful, pleasurable or all three for you. An Anatomy Lesson A person with a vulva actually has three "holes" or what I prefer to call openings per their genitals: If you felt pressure in or around your anus, that doesn't necessarily mean that your boyfriend's penis entered there. Give his penis a hand. So, how do you make sure your boyfriend's penis doesn't end up where you don't want it?