Personally I really can't say what the right answer for you is though I can identify with your situation. I got curious about taking it as a bottom some years ago and though successful, I still feel like I have a ways to go.

I find when you get past the drug suggestions and the slut advice (do I really need a bag of dildos lying around--I don't think so), it starts to boil down to the real issues of giving yourself up to another guy. How it makes you feel about your own manhood: and most of all--who really wants to fuck around with shit?!

The answers for me where many,

A). It really takes the right guy to even get started. I am not the type to give it up to anyone. But I wanted to for "this guy" I really did and it worked out. Of course after that I kind of got a lot more successful with other guys, but that is another story.

B). It takes time to work out the misconceptions others have about bottoming that you may have rattling around in your own head; even in the heart of the gay community the feedback isn't necessarily positive. But I do think that a lot of resistance for many of us comes from not wanting to be grouped into the over-active total bottom stereotype.

C). Let's get practical!

1. Most guys seem to have a fairly clean colon for the first few inches. So spontaneous sex is not out of the question. But practicing giving yourself enemas wouldn't hurt. you only really need to clean out the colon, not the entire dietary track.

2. A dildo would only help you explore your own ass and what works for you. doesn't really help you take it better, but the experience in exploration might. Though a real cock is so much more effective.

3. Surprisingly, the best advice I ever got about taking it up the ass was from a good friend with an exclusively top boyfriend--with a big cock, take a hot bath or shower (as hot as you can stand it) just before sex if possible. For some reason it relaxes the colon and your internal muscles without getting everything loose.

All in all, the real goal is to build confidence so that you have some control over what you are getting yourself into...or in this case what you are letting get into you. :) The more confident you are about what is going on the more enjoyable and successful you will be.