We are always trying new things...but so far no luck. I just have so much trouble getting hot enough to come...and he is not going to feel better until he can make me come.
Why is orgasm the goal?
Why is you having an orgasm the only thing that makes the Shared Sex "successful" to him?
So odd to me. I tend to think the goal of a good Sex Share is to Share!
If orgasm is the goal I can always roll over and masturbate and get off. Presto! It's not like I need a partner to cum. Sharing sex with a partner is to enjoy being with the partner to me.
He has a low self esteem which just keeps getting worse and then he had no confidence and then I have a lot of trouble being turned on by this...which just perpetuates the problem.
Well, if there's bad self esteem -- what's he plan to do to work on it?
If DH is dependent on your for everything maybe there's the other thing -- it isn't him "sharing" himself so much as you doing all the work? You aren't being gifted his Sex Share in a close intimate time. But more like... clocking time? And who wants that? To feel like you are servicing him rather than enjoying a good Sex Share with partner you desire and are turned on by?
How does HE want to share himself in sex? How does HE want to deal with his self esteem bucket of issues?
I don't see how pulling away from each other will solve anything. Keep trying to come together and share the time, not avoid it due to lack of orgasm!
I know if we spent more time together it would be easier, but his job takes him 6 days a week, all day.
Well, that is a limitation you presently both have to deal with. The limit of the job taking up so much time.
Try to relax and have fun with each other. Give him something new to think about. He's not up for "rough stuff" so perhaps this could honor that for him but could be intense enough for you...
Since you want to explore new things, and you got the lube out already, and he wants to make you cum and you are thinking about kink -- how about exploring "A Hand in the Bush?"
with him? It's slow, intimate edge play of another kind.
Learning to do that together might increase your hotness for him and his self esteem in his sex skills.
I don't know if that floats your boat but if it does? Make a date for Target -- get the gloves, a small mister bottle for water to spray and reactivate the lube and hit the baby aisle for a waterproof bassinet liner to sit on when you are in bed exploring this. Because if you both learn it to where you go and jill, it goes all over. Hello, laundry!
I can't imagine he would not be impressed with the "Wow! I helped her do that!" A nice boost to the esteem and since BF gets you off so many other ways, something you could save as a special thing for just DH.