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Don't worry about disappointing him by wanting to go slow and gently. Finger Penetration When I was comfortable with anal play, then we moved on to inserting just one finger into my anus. Emily Morse advises keeping baby wipes on the nightstand and to "never use the same condom going from vaginal to anal and back again. That said, it also comes with a lot of risk. Really great info can be found on site First, we have the famous doggy style position, in which the receptive partner is on all fours, though this position may cause a bit more discomfort for beginning anal enthusiasts.
So, I decided to write a brief recollection of how to have succesful anal sex experience. So every time I desire anal sex, I usually go through the same steps. Here were the steps I took before engaging in my first anal sex, anal intercourse experience. It actually took a few months before my boyfriend penetrated my ass with his cock. Cleansing usually consists of emptying my bowels, or at least trying.