SnozzberryBlu, I think that considering his initial feelings and upbringing that he's doing fantastically well! Just look at how far he's come from there.
If you're both willing to continue, I think that future experiences, especially with the same people, will only get better because he'll be more relaxed the next time.
People tend to think that the male sexual response is fairly simple. In reality, it's pretty complex and it takes the right combination of arousal
and relaxation to make things work properly.
Best of luck and happy swinging!
-B