Can anyone help me help his confidence?! Long post!

Joelle
I've been seeing this guy for a month now, we've finally had sex, we waited three weeks before anything. The first two times were short lived and the foreplay was harsh, fumbly, awkward in every way, lots of directions were being given and not completely understood, and it sort of hurt because pressure was off... Then the sex, again short lived, only did me on top (the first time) and then him on top (the second time) and it was sort of painful and completely lacked experience from his end. The most recent time was tonight (2 days after the first time) this time there was no foreplay except maybe 5 minutes of kissing, him on top, and then I still never came. I did tell him as much as I loved sensual I really prefer a little more motion and friction and he gladly obliged but still i couldn't get out of my head with trying to figure out ways to make it better for me. He is such a sweet heart, kind, never expects me to want him, shy and lacks any confidence in the bedroom. It's a turn off! I love spending time with him, holding hands, kissing, watching movies, shopping but our bedroom time is hampered by his lack of experience and confidence! 
PS a little background, I've had my fair share of sexual partners and have been told I'm pretty good in bed, he was with his ex for 9.5 years, she was his first, he said it was fun when they first started having sex, then she asked to stop due to religious reasons (this was a year before they wed) after their marriage they started up again only for it to be "boring" *his words* and dwindled quickly only for him to catch her cheating a year and a half later. His confidence had obviously been dwindling quickly along with his marriage's chances. 
They are divorced and he still lacks this confidence and has told me that he was nervous that I wouldn't like our sex. Well he's not wrong but I want to like our sex and I want to help him. I don't want to sound too bossy or make him feel inadequate and I don't really want to be the most dominant in the bedroom either. He doesn't watch porn or even masturbate on his own free time. I just don't know how to deal with such inexperience and low confidence and I don't really want to leave him either. Please if anyone has similar experiences and or can help I would be so so grateful