I'll just use a few words to convey my point: A lot of alcohol. Not a lot of foreplay. An extreme lot of awkwardness. A mistake (?) in aim ... Sharp and unhappy pain that went on and on ... Limping for three days, with a nice ache for four more days after that. I'm still not one hundred percent recovered from it ... a week and two days later ... but that's not to say I wouldn't try it again! What I learned: Next time, skip the booze (well, at least cut back on the booze) ... prepare more ... and use lube!
not enough lube, going deep too fast, didn't use a vibrator on my clit so I didn't come learned to do the opposite of the above lol talk about dh being a pain in the ass
Worst: She cried, I stopped. Learned: Giving anal isn't always easy. and All women are not created equil.
My worst experience (like many other peoples') was mostly at the cause of not enough lube and no practice. It was one of the first times I tried anal, long before I discovered that you can't just go sticking a dick up there with no warm-up practice. We were fucking, and he pulled out and tried to fuck my ass. He slid in a little and the pain was pretty bad... He asked if I was okay, and I assumed that the pain would subside momentarily, so I said I was fine and for him to keep going. So, he thrust hard and I yelped and started crying. He pulled out and apologized profusely, but I was so turned off and sore that we just gave up for the night. I learned from my experience though, and haven't had another like it.
my worst was with my high school sweetheart: we both were curious, so i guess he decided to do some research on the internet. Right as we were getting ready, he turned to me and said "act like you're pooping" I was so grossed out by his "by the books" analysis of the situation, i cut it off right there.... my boyfriend and i have some great sex now, but that first time really got me for a while.
HOLY FUCK MAN!!! That ain't cool, the bitch ain't ever suppose to analy fuck the dude! Holy Crap! Oh man, I'm sorry, I didn't get who you were, okay, I would've edited my messege but it wouldn't have been as funny.