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It's hard to know, because everybody's different, and that includes each butthole-fingerer's individual skill. The whole point of anal play is to keep it simple before working your way up.
"So many women have bad first-time experiences and never want to do it again. "To prepare a bottom for sex play, start with fingers, tongue, or a very small sex toy designed for butt play," says clinical sexologoist Dr. "An option is to purchase a Butt Plug Kit that uses several plugs, of graduating sizes, just for this training." 3.
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While some women only need butt play à la carte, most women can't come from anal stimulation alone. It adds to the overall experience," says Ian Kerner, sex expert, researcher, and author of . "Baby wipes should be mandatory on every nightstand," says Morse. If you try it a few times and hate it, don't keep trying it because you think it'll eventually be tolerable.
(Incidentally, women who have had anal sex report more frequent orgasms than those who haven't.) That being said ... Make sure your partner doesn't use the same butt finger in your vagina afterward. "Assuming you have a considerate lover who's invested in you feeling good, I think you'd know within the first five times whether you like it or not," says Kerner, explaining that this depends on a variety of factors.
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