Message: The Rougher The Better, But Initial Anal Penetration Is Still Hard
Anonymous: I enjoy having anal with my fiancé and I’ve discovered that the harder, faster, and deeper he goes the more pleasurable it is. But I have a hard time getting over the initial insertion. Maybe I’m not training well enough or using enough lube. Any suggestions? Because I really want to get to the point where I can just throw my ass in the air and let him do whatever he wants with my butt without any pain.
If it feels fine once the initial penetration is over, it probably isn’t lube-related. Train more regularly (no less than 3 days a week, and daily if and when possible) and work up slowly to larger sizes. Occasionally wear a butt plug around the house or while sleeping for as long as it’s comfortable. Always train your ass whenever masturbating.
The more often you masturbate anally and have anal sex, the easier it gets. This is part of why going anal only is so effective—once you’re doing it all the time, it’s just all pleasure all the time.