Checking in again - certainly do things when they feel right for you, no need to lay down a strict boundary if that's not where you're at. I just saw some dissonance in your posts - you said you wanted honesty/fidelity and didn't feel comfortable with a 3rd person involved in your M, but I didn't see what exactly you were doing to set that boundary. It's important to remember that YOU have needs, too, and that you're not doing all of this at your own expense of what you are comfortable and OK with. Another way to think of this - what are changes you can make for yourself that don't involve around reacting to or interacting with him? I was stuck early on too about trying to make all my changes about how I could be more appreciative, more caring, more loving, etc... it didn't really make a difference, for a variety of reasons. Instead I'm now trying to focus on myself and what I can improve in general, irrespective of my interactions with H.
What's up exactly with the sending the sexy women pictures?? Why does he send them and what's the point? I'm glad that you said how you really felt about them in this instance. And in a way your H acknowledged that but it was like one of those "I'm sorry, but.." apologies... "I don't want you to feel that way BUT I'm just trying to have fun, lighten up here!" sort of thing. Has it made you feel inadequate or uncomfortable in the past but instead you forced the flirty/sexy talk? Did you do things you were uncomfortable with at the expense of your own boundaries and feelings to try to please him?
My personal opinion: when your H suggested the class and said he was a wise man... I don't think you need to pander to his ego any more at that point. That was a bit over-the-top. Your H may have his own issues to work on regarding getting applause and appreciation from others instead of genuinely being happy about himself. I'm not saying your H is in any way similar to mine, but in my situation my H SAID he wanted more appreciation/compliments/etc. When I tried to do that more, he just deflected them, and later when we had a discussion about it, he said "I feel like I need the compliments and appreciation to feel better about myself... but what people can give me is never enough.. I feel like I always need more and more because I never quite believe it when people say it so it doesn't make me happy like I think it will." It's possible that no matter how much you do it really won't make your H happy, because he needs to figure out how to be happy with himself and his own accomplishments, even if there's no one there to notice them. There's a balance to strike between speaking someone's love language of words of appreciation/admiration, and being the sole source of their esteem and "happiness."
Me:30 H:29, no kids T:12, M:4 (when D was final) 12/13: "Don't think I want to be M anymore" 6/14: Separated (I move) 1/15: H filed for D 5/15: D final