Hey, Archubbycub, the more you do it, the better you get at it and the better it gets... The body kind of has muscle memory and learns to relax quicker, that is if you keep doing it quite regularly... If you go some time without it, remember to take it slowly again the next time you try. Your body will have unlearnt some of its former passive behaviour.
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Bottoming feels good, but you just have to, like everyone else has said; relax. (oh and lube up).
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I have to agree with ceez that once you find the prostate the sensation is amazing. I know what you mean about the after-feeling, but I still prefer bottoming. With my first guy, it did hurt initially because he would just jam it in there, but it was still worth it. If you're worried about the pain, I would recommend choosing a position where you can control the tempo and speed.
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If done correctly it's amazing. Also just putting my two cents out there I feel you have to bottom a few times to be a good top....
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