I always make sure my ass is very clean. I usually do 2 or 3 enemas before sex. Having a clean hole relieves me of the worry of a messy accident. Also, being clean makes you very smooth inside, and you don't feel debris tearing you up.

I always lube up with a lot of vaseline or food grade coconut oil. Vaseline is thicker and takes less. Coconut oil is thinner, but clean up is easy, as it absorbs into your skin.

Entry is done by pressing the cock against my hole, and releasing. Press, release, press release. Take your time and it will eventually go in without effort. Subsequent fuck sessions get easier. Soon, your ass is trained to relax and the cock slides in the first try.

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