Erik101 saidPractice with a dildo. If you chicken out from that, then there's no hope!
I respectfully disagree. I tired the dildo route several times; a hunk of latex did NOTHING for me. Dull, painfull, tedious and boring.
I waited a looonnnnggg time unitl I found the right man to deflower me, a skillfull, sensitive top man who took his time earning my confidence, trust and eventually my admiration and my anal virginity. After a long foreplay session with kissing, lube, fingering, rimming and stroking; I was amazed at how easily he slid in me, when we both finally agreed it was time to do it.
It's either him for me....or just my left hand and porno movies.