No. Full stop. Pain is your body’s way of saying "slow down." The anus is surrounded by sensitive nerve endings, but it is not self-lubricating like a vagina. Discomfort happens when you rush or skip lube.
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During foreplay, use a lubed thumb or finger to massage the external sphincter. No penetration. Just pressure. Do this while giving oral or a handjob. The goal is to associate anal touch with orgasm. lustery anal