Painfull anal penetration

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We checked in with some experts and asked them to take the mystery out of anal sex, and they schooled us on some positions that can help ease you into your first time to actually make it an enjoyable experience. In the traditional cowgirl position, your partner lies down while you mount on top — yeehaw! As the partner on top, you can ease into anal penetration by moving up or down as needed. Remember to go at an easy pace and stay relaxed. It helps to have had an orgasm already and be highly aroused.
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Painful intercourse (dyspareunia) - Symptoms and causes - Mayo Clinic

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