Well instead of TALKING about doing it, how about some action instead?
Since you like him so much, I can understand that nerves can be a huge factor. Would a little wine help?
The next time you are both alone at his or your place, snuggle up to him + while kissing, try moving your hand down and stroking his manhood.
Then let things progress organically from there.
In other words, let nature take its course.
Try not to overthink anything and also not to strategize anything either. This can be catastrophic when it comes to sex.
Good luck and have fun tonight!
