Haha I wish, unfortunately I'm currently with family for the next 2 months so I dun have the chance to 
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Either you are or you are not.
Usually if it doesn't do something for you, you are not. If it does something for you then you are.
Pleasure is not a very defining quality of top/bottom roles as there are a vast number of different pleasures that can possibly be felt.
Prostate massage can be pleasurable, however it may not be indicative of a bottom's pleasure of being filled by their man and other emotional undercurrents that being 'on the bottom' bring with it.
Sex is not simple yes/no or black/white answers. There are so many other emotions tied into the sensations, ones that go beyond mere lust/pleasure.
Understand a bottom typically wants to feel their man inside of them. It is a rather indescribable sensation. This is more than just the pleasure of having the prostate massaged and often extends well after the rough and ready action of sex is over.
It is these side emotions, these undercurrents like this that determined 'top/bottom' roles.
An anal orgasm is a product of prostate massage. This has nothing to do with top/bottom roles it has everything to do with manipulating the prostate. Just like jacking off has nothing to do with your being gay or straight, its what you think about, want/desire/need in a person you copulate with that determines your sexuality.
Hitting the prostate just right with a dick ain't easy. And its not hitting its rubbing. So yeah, your partner has to know how to use his dick and know enough anatomy to find your prostate in order to rub his cock 'just right' with sufficient pressure - no pounding the prostate doesn't do it, if anything it can cause more pain.
I can't stress this enough - that is prostate massage, and has nothing to do with top/bottom roles.
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I'll second a few things here. Lots of lube and lots of foreplay. Also, position has a huge effect on the amount of discomfort/pain the bottom feels. I like straddling my partner from on top of him, or lying on my side. But lying on my back almost always causes discomfort, if not pain. I imagine people's bodies are different here, and the shape of your partner's equipment most certainly comes into play, too.
And again, some people really do just prefer one role over the other. I don't enjoy topping, but love bottoming. That's that for me and I'm fine with it.
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I regret that we have come to a point where we have come to a point that requires, or seems to, that we have to self-identify as a top or a bottom. Over fifty years ago when I was being tutored in sex, I was told that just as I wanted to mount a man, I had to understand what he was feeling, how to increase his pleasure. Unless, unfortunately, you're with the sort of person who only thinks of themselves when it comes to sex (and probably everything else) it's a good thing to have some knowledge of how things work, how to make them feel good for them as for you. I've seen men "doing it" in all manner of strange positions, many requiring one to have been, at least, a gymnast and I cannot think their really enjoying themselves. Maybe they are but....I doubt it.
It's not just for one man that you learn, it's for the whole skein of men over the course of your sexual life that these skills and understanding are necessary. There comes a time beyond the giggling "we did it" sort of fuck, that you discover the mellower, better long lasting kind and if you're not prepared, your partner will know it and either have the sense to help you learn or will leave you. It's called, "I don't know, the sex just wasn't there." It may sound awkward or nasty but you've got yourself 24/7 to practice on. I'm not suggesting you grab the long end of the family mop or hump a door knob, but I am suggesting a reasonable dildo (not one that seems to have been copied from a Cape Buffalo) and work with it. To this day I regularly have something up my ass as I go through the day. Nothing big, just something that plays "Tag, you're it" with my prostate depending on my attitude.
Get a book called "Bend Over" a terrific book (available at Amazon.com) about anal sex and sex in general. It's wonderfully written, informative, illustrated with pictures not stick figures, and you'll come away from reading enhanced in all sort of good ways. Save for the prudery factor that is rampant in the land, everyone should read it.
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I'm a total bottom. I need cock inside me. It's very much a mental thing, I think, when guys really lean toward top or bottom. And I know from friends that a lot of guys are versatile. I would say what do you FEEL, what do you CRAVE? My first time getting fucked hurt, but I totally got off on being taken and dominated. What do you like? What do you want? I think those are the big questions. Good luck!
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The first time i were fucked in the good way the fellow must have really known his stuff because it was pain free and fun. Spit is a fun lube. Can i say that here?
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I consider myself vers till Ive rly tried bottoming :p, but I believe I lean more to being a top
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My advice, buy a small toy, ideally some type of beginners prostate massager. There are plenty out there as far as I know and some of my friends (recovering tops) swear by them.
On friend in particular used to be, in kind terms, rather obnoxiously proud of his status of a top. His boyfriend, who he is still with, was truly versatile and got him one of these devices. It took work, time, and patience, but my friend actually couldn't believe how much he'd been missing out on in terms of the sexual pleasure available to him.
My point is basically get something that is designed to stimulate your prostate optimally. Figuring that area out on your own without knowing what your doing is literally like taking shots in the dark. Having something specifically intended for prostate stimulation should remove at least some of the confusion and help you learn what makes you respond favourably to anal stimulation.
Lastly, I really wouldn't recommend exploring this side of your sexuality with someone who doesn't know what they're doing. Try to get something a bit more long-term going (friends with benefits?) with someone with whom you have some degree of connection, and who is good at using their equipment.
Good luck!
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Going bottom
