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In your question, you said that your boyfriend readjusted himself after a while. The easiest way for you and your boyfriend to make sure you're both engaging in the sexual activity you want, and that you intended to engage in, and that won't hurt either of you, is to talk about it. The anal and rectal tissues don't lubricate themselves, as vaginal tissues do, and are even more sensitive to cuts and abrasions, and accompanying infections.

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How do I keep him from going in the wrong hole?

I know it may seem as if his penis is much bigger than your vagina, but the vagina is really quite elastic. This is which hole sex I actually find it a little difficult to use the word hole to describe a body part and instead tend to use the word opening or to use the anatomical term, as it seems, to me, to connote something impersonal and inactive, when, during sex or any other activity in which our bodies are interacting with other people or with the environment around us, our body parts are anything but inactive. Check in with yourself with a "Am I having fun?

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Next comes the vagina, then, finally, the anus. Actively participate in what you want and actively speak up for what you don't want. Starting at the front of the body, we first have the urethral opening, where one urinates from. There are other reasons besides having genitals not fit together in a way that is comfy for your body for intercourse to be uncomfortable, painful, or not pleasurable. Plus, all the muscles of the pelvic area are connected in some way, so any pressure on the vaginal muscles can translate into pressure on the anal and rectal muscles, and vice versa.

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