Aren't you a sweetie. This is what works for me (in order):
Lots of anal rimming (where you lick her ass and stick your tongue in there a little at a time). Get her ass hole really wet and as loose as possible.
Stick your pinkie finger or the tip of your index finget in...work it in and out, lick some more, alternate based on her reactions. Do this for a while.
Lube your cock up really well, glide it up and down her ass, inserting it just a lil each time you pass her ass hole.
Proceed based on her reaction.
Also helps to reach around and stimulate her clit as you enter her....feels really good that way.
Oh! Ask her to be verbal with you - "Mmm baby, that feels good. Yeah, don't stop, go futher". OR "Oh, ouch, try licking me a little longer baby".
Just
TAKE YOUR TIME. Anal sex isn't something you rush into, or it can be painful.
Have fun, and let us know how it goes :wink: .
My girlfreind and i are interested in trying anal. However we have both tried it once with different partners in the past and she found it really unenjoyable and the girl i was with said it hurt. I do not have a big cock really just an average one. Any suggestions on how to do it so it is an enjoyable experience for the both of us, particuallry her as i do not want to her to be in any pain or discomfort. thanks