Did you enjoy it the first time?
I had to try a couple times before I managed to get anything in... first time was a tampon (I kid you not) I think I was about 12, it didn't want to go in and I barely managed the tip if at all.

the second time was with my first vibrating dildo and wow did it hurt! I didn't use lube got maybe 1/2 an inch in and then pulled out and it throbbed! I finally succeeded after sucking on it a bit to get it wet and carefully get it in while curled up with my legs tucked up... that's when I learned that anal is all about the angle at least for me.

Do you enjoy it now?

I love anal! although the though of anal sex before we're actually doing it makes me sqeemish, as usual for me, I need a little lube and just the tip in and about 20 seconds or so for that little inner sphincter to relax, then it's all good ^_^

Not a lot of lube though... because too much lube makes it slide in a little too easy and a little too fast, then it just hurts because I don't get time to adjust

my Master says that my ass is opens up easier than my pussy and I'm inclined to agree... He's longer than I'm deep so getting the end of my vaginal canal smashed isn't very pleasant DX