Jenna....listen to an older guy who has lived this. You two are not going to solve your relationship world over night. These things take time but I like that both of you are getting things out and working on them. Don't take these sitches as losses or fails...they're good for you both.
And BTW he had big ones to tell you what happened. My hats off to him. Its not easy to bring that up and admit because most chicks can't handle strip club safaris. Take it from me, he really didn't want to go (believe it or not a lot of guys find strip clubs as low life... and no that doesn't mean they're gay or wimps) and if he bailed on his buds then he would get derided.
As far as trust Jenna, and you need to think this thru...if you and him need to have this fifty page guide book of what is and isn't over the line...then you probably haven't learned to trust in a R. You have to let each other decide who and what sex people you befriend and trust each other to live up to the commitment. Trust me, my W could not trust ever, and had no reason from me to feel that way, and its costing her her H and children. You're a really top notch woman, but there always room for growth in all of us.