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Always withdraw slowly, either with muscular outward thrusts, or by pulling it out, or both, gently stroking the sensitive walls of the passage as you do so.
The most important piece of advice I can give to anyone with concerns about bottoming is to be relaxed.
Hold out your butt as far as you can, and hold the lubricated tip against your butt hole, at the correct angle, rubbing or poking as gently as you can.
The tips in this slideshow progress from beginner bottoms to more.
You can always try again later.
Start with a carrot more slender than a penis, and gradually work your way to ones of proper thickness.
But they can only reach so far.
I prefer a fetal or spooning position.
Looking for a lover, all the details in correspondence.