I like anal sex -- a lot. And I always have, back to the first time I tried it.
While I was a teenager, my submissive fantasies started to venture into the territory of sodomy. I was turned on by the idea of being taken in the ass, but had no idea how it would feel.
I decided to experiment while masturbating. I used my usual makeshift dildo in my pussy, but I also put a slim taper candle up my ass. As I stroked my clit, I gently worked both foreign objects. The orgasm I had was unreal! Nerve endings were exploding in my ass, pussy, and clit, all at the same time, and I was super turned on by my fantasy as well...
Needless to say, I repeated this experience many times.
With all my partners before my ex-husband, though, I was too ashamed and shy to admit I wanted to try anal sex...none of them ever suggested it, and I thought if I brought it up they would think I was perverted.
But a while after I started dating my ex, he just decided to try going in that way one night, and after applying some spit (we didn't have any lube), he entered me. I didn't come that first time, but I did enjoy it.
I really don't understand the whole thing about it feeling like taking a shit backwards; it feels completely different to me.
Anyway, my ex was just a little bit larger than average in size, and all the times we had anal after our first go, we used some kind of lube. He would always have to enter me slowly and gradually so I could relax and adjust to him, and I will admit the entry was painful, but things always got better once I relaxed.
I will say that the indispensable ingredient to make anal sex pleasurable for me, though, is to always stimulate my clit the whole time he is in my ass. If I take my fingers off my clit, the pain becomes more obvious, but if I keep stroking my clit, the pain is almost nil, and is totally eclipsed by pleasure.
I can come easily from anal, but only with accompanying clitoral stimulation.
My present husband is a good deal larger than my ex, so taking him anally has been a bit more daunting. We've done it a few times, and I do manage to adjust eventually to most of his shaft, but he is even thicker than 6" at the base, and getting that part in always hurts. I think his base is about the limit of what I can take anally.
Anyway, we have done it both with me on all fours and face to face with me on my back, and once I relax after a careful, gradual entry with plenty of lube, he is able to pump pretty enthusiastically without really hurting me.
I have never bled from anal sex. I have been sore, but it gets better in a few days, and I don't have anal often enough for chronic soreness to be an issue.
One additional thing I will say is that in my adult life, I have continued to experiment with foreign objects in my ass -- dildos and butt plugs, used both in conjunction with vaginal penetration, or without.
Being fucked in the pussy with a medium-sized butt plug in my ass is very pleasurable for both partners.
I also think having played with butt plugs and dildos has gotten me more used to anal sensations and has made it easier to enjoy anal sex.
Finally, I will mention that if you are (as I am) a little bit embarrassed and squeamish about the state of your rectum preceding sex, you can use an anal douche (with plain water) a few times to clean out any unwanted residue. Once I started doing that, I felt a lot more confident about ass play. You can get an anal douche from an adult store. Do NOT use an enema like you get at the drug store -- these are not plain water and are designed to make you shit, not to clean you out.
Sorry this post is so freakin' long!