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How do I know if it hurts too much or if I should push through any weird feelings? Anal stimulation can feel a lot different than vaginal stimulation, and can have a greater potential for pain, so it's important to know what to look out for. How can I work my way up to having anal sex for the first time if all I've ever had in there is a finger? Ask your partner to stay still on their knees, and allow you to push up against them. More and more people are experimenting with anal play. Over the course of several sessions, play around with inserting the finger deeper, and starting to move it in and out.

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