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Anal tearing is the largest of these, and can easily be controlled by lubricating the toy, finger, or tongue you are going to use for anal sex. Giving yourself anal male tears in the delicate skin in and around the anus increase the risk of transmission of STIs, including:. Get tested online. This is how anal orgasms work for cisgender women and people assigned female at birth. Start with something smooth and small - about the size and shape of a finger - without sharp edges and let your anus adjust to giving yourself anal male size of the item. Their concern was that their man's interest in trying anal sex is a sign that he's gay or bisexual.