First of all, congratulations on your sensitivity. It's refreshing to see someone your age so concerned with your partner's comfort to the level you've expressed.
You've covered most of the essentials, except mentioning using a condom. Don't forget. :)
One thing I'm unclear on from your post . . . . have you two been having oral sex and mutual masturbation before now? If not I would suggest starting there. Anal doesn't have to be included right away. Get to know each other's body signals and learn what he enjoys and how he enjoys it.
If you have been doing the above and honestly feel it's time to introduce anal sex, start with slowly entering him with a finger (be absolutely sure your nails are clipped down). It's less of a challenge and helps him acclimate to the feeling. It also allows his sphincter to relax. The first time you might not even get to actual intercourse. That's fine, you've got plenty of time.
His history of sexual abuse can be a real issue, and I hope he's getting some professional help with it. Make sure he's not agreeing to this because he wants to please you or thinks you'll be disappointed if it's not included. Be patient, and if it doesn't come to pass take stock of how important that particular activity is to you . . . . many gay relationships don't even include it because of one or the other partner's dislike of anal. There are plenty of ways to have a satisfying sexual relationship without it. ;)
DVDBear
Posted: 30 Sep 06:27