angelstar...go with the top position to keep some control and allow your confidence to build...later you can get into the gymnastic stuff if it suits

you're bound still to feel some kind of discomfort at first - and its worth remembering that not everyone finds anal play to be total fun...some people actually find its not for them

still...your sphincters are muscles...so they should be able to be trained...and in a short time learn to accommodate most 'normal' sized thing anyone would want to place there

I think rather than pain the more likely comfort issue will be getting used to having that 'filled' feeling...like you're caught in the middle of a bowel movement

my only comment on condoms and lube...use plenty of wet stuff if you need it...but I also think it can make it harder for the other person to control the penetration...so if you're using lube to ease the entry just take it as a sign of the need for extra caution lest someone just 'slip' and give you the full length all in one go!!! - less of an issue if you're riding high :-)

and yeah...try and relax