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As usual, first-timers are prone to bleeding just as they would with first-time vaginal sex. So if he gets too carried away, tell him to slow down or stop. Didn't receive the code? Grab hold of his penis and then slowly guide it inside your anus. If he is using a condom, and takes it off or changes it, then yes.
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We used Vaseline, but my boyfriend later realized that it deadens sensation on the skin, which was obviously helpful for my asshole but bad for his orgasm. All on her first anal date!! Deep kissing, squeezing nipples, rubbing the vulva and having vaginal sex for a few minutes first really helps to relax the anal muscles. You may even be sore from a previous session.
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