“Tipping-in works much better than trying to insert something at a perpendicular 90-degree angle,” Ligon says. Once you're a little in, gentle swirling or side-to-side, up-and-down motions can help relax you further.” “That way you aren't ramming something against your sphincter and you're able to massage it open more gently. When starting out, keep the toy inserted for roughly five seconds, remove it, and repeat 10 times for three sets. This will help ease your anus into the sensation of penetration at a speed and depth your body is most comfortable with. If penetration isn’t your preferred training method, you can wear a butt plug for an extended period of time to get accustomed to the fullness of penetrative anal sex. However, it won’t exercise your sphincter the same way that active play with a toy does, which is more similar to the sensations of anal sex with a penis. “Just be gradual in everything you do,” Ligon advises. “Some people require less warm up than others, so noticing sensations and relaxing matter a lot more than the specific length of time you play for. The more you do any sex act, the more awareness you'll have over the nuances in sensation.
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