Thank you all for your advice! Each of you, have given me food for thought and certainly have helped to ease my concerns by answering my questions.

I am 100% looking forward to the prospect of experiencing anal pleasure, tho it is the unknown that causes apprehension. I have never been with a partner that ever expressed a desire to introduce me to this.

I am only slightly concerned about the possibility of not enjoying anal sex, as my main concern is that it pleases him. In all aspects of my sexual experiences, I have always been more comfortable giving pleasure than experiencing it myself. That being said, I believe that he also wants me to truly enjoy it and will be patient in teaching me.

I will certainly take Lilith's suggestion and consume a little bit of wine to help relax. Altho, it won't be very much as I don't want to "miss" any of the experience overall.

Again, thanks everyone. If/WHEN this comes to pass, I am sure we will take pics!