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first time anal sex – How to get started with anal sex . So how does one go about doing this? Well, it’s quite simple. Begin by relaxing, lubricating your anus and inserting a finger or two into the hole until you feel comfortable enough to move on (the lube is important here). With patience and care, slowly push something in there until it feels good. And remember; It only gets better! While adding another finger should increase pleasure levels even more, if you are still unsure then just hold back for now since you may need some practice before your body gets used to the feeling of having something up its own butt. The last thing that needs mentioning here is safety: This technique should NEVER be done without proper protection against STDs such as condoms or dental dams.