Yeah, it hurts me a lot. There's only one person I've ever bottomed for, and I was in love with him, so there was a lot of passion and emotion that blurred the pain. Even then, I mostly topped because 1. I prefer it, 2. the initial pain is awful.
I read an article recently on the Andrew Christian blog not too long ago about gay myths, and I think you should give it a quick read through. (NSFW link) Especially #2 and 5. You mention that you don't feel oral can be as intimate as penetration, but it definitely can be. You can throw other stuff into it too, you just need to find what it is that gets you going and what you can confidently give a partner. Don't feel compelled to penetrate, regardless if you are a top or bottom.
Like everyone else has said, when you do decide to bottom with a partner, try to get plenty of foreplay in there and really get your mind and body into the mood. When you really want it, the pain flushes away relatively quickly. You may be like me though, where you can only bottom for people that you feel an emotional connection with (not hookups) which is totally acceptable!
