How bad does Anal sex really hurt the first few time, exspecially the first?

My fiancee said it hurt the first few times. Then we bought a few cool toys like smaller dildos and stuff and she uses them before anal sex as part of our foreplay.

You should practice with your fingers and stuff before you go try it.

It does, so a receiver should exercise with objects beforehand. Especially right before the action.

I've tried it a couple of times.Tell him to use his finger first to get you moist and stimulated.Then when u feel like you are comfortable, tell him to ease a litle in at a time.It feels sooo good.But the first time hurt a little.I was nervous and my body tightened up.Thats where the pain came in.

It doesn't need to hurt at all. In fact if it does, you are doing something wrong. Read on: http://mflife.wordpress.com/2006/10/12/anal-sex-101/

Nope I have had Anal sex on numerous occasions and can honestly say it has only been pleasurable. Not the slightest discomfort. May I suggest you use plenty of lube take it slow and enjoy. Of course if you are doing the receiving...I have no idea ..but would hazard a guess from all the screaming and tears and blood that it might be a little nippy, but HEY! HO!

My first time it hurt like a bad paper cut. I enjoyed it but it hurt like hell. Now it doesn't, i suppose i got used to it.