Hi SpikesKitten,
I'm sure there's a thread around in the knowledge base that covered this topic before...but I'm not looking for it today.
I recommend starting slowly, get clean with a nice enema,
have him use lube on a finger, and gently "finger f*ck" your anus.
How does that feel?
Do you want him to continue?
If you are practicing on yourself, squat, lube your finger,
put your hand behind your back, reach between your legs and go for it.
When you first do this, it may feel like you need to have a bowel movement as your lower body is trying to push the foreign object out of the way. This can cause you to tighten up and make it painful. Take your time, breath deeply and focus on relaxing.
If you are using toys, start small, but make sure there is something on the end to keep that toy from dissappearing inside of you. Use something flexible that can bend with you, like manflesh would, not some hard plastic toy.
Here is a link to 10 rules of anal sex:
http://www.sexuality.org/authors/morin/analrule.html
Oh! and this site also has a list of recommended positions for Anal. Jackpot!
http://www.sexuality.org/l/incoming/aanal.html
If something ends up working for you that you like,
let us know.
Have fun!
Ruby
PS
Anybody have a favorite position that listed in that article?
One that isn't?
Enquiring minds want to know.