Interesting and valuable insights and hints, here, guys! I agree, too, that the early tries might be assisted along with kudo451's advice about lying on one's side as the bottom. (Related to this, is the position my urologist puts me in for protate ultrasoundexams/biopsy, etc. using the ultrasound probe which is much like a medium dildo, I guess). The torso is more relaxed as is the rectum, as opposed to the body core muscles having to supporting you upright or even in a doggie position -- it allows things to "intrude" much easier, IMO.
The deepest penetrations are enabled by the bottom being on his back, missionary style, legs up, or riding the cock from above cowboy style, I think. Although with him being on his stomach and the top guy lying on the bottom's back entering from on top is no slouch either
wink
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I'm the top mostly -- although for the right guy I'm ready to flip and go into that zone myself! To do that for me, not a "natural bottom" the secret is, as stated somewhere else on here by another (astute) poster: "with enough time, lube, and lust, anything is possible" -- It's TRUE! Believe me. "Chemistry" is magical, I think. And an orgasm enhanced by rectal stimulation can be IMMENSE!
The other suggestions of fingers, dildos and butt plugs, practice, silicon lube, and so on are all very valid, too. You may not become the complete bottom you visualize, but I'll bet you will get to the point where you bring that bottoming option into the mix and you'll both be having some wild times!:smile: