I don't think I've ever experience a good sex life (Sorry TMI)

[NowIsMyTime]

And I am just realizing that now. Aged 44yo....

I only have had 2 sexual partners.
With the first one, sex was nice but I never got to the point of orgasm.
Second one is my now DH. He is completely unadventurous, always has been. To start with I did take the initiative, nudge him into trying other positions that 2 'regular' ones.
Add to that 10 years with various problems incl my health and nearly getting divorced, I am getting better. My libido is back and I want more.
I want proper sex when we will both get an orgasm and have fun and it feels nice.
I want him to take the initiative so that I get an orgasm too (Not just me going on top and rubbing myself so I get it iyswim).

And I am at loss as to what to do about it....

So what do you think he would do if you had a chat about it?
If you used non accusatory language and just said you felt stuck in a rut and you'd like to do this this and this?
Does your dh know you're frustrated?
What did he do wwhen you last took the initiative.
Lots of people are happy with a sexual routine and that's fine, but if you want to change things I think talking (with some alcohol would be my method!) has to be the first thing.

He doesn't necessarily have to be 'adventurous' for both of you to achieve orgasm. What's usually required IME is relaxation, time, attention, sensitivity and what I call 'sexual generosity' i.e. being more concerned with making sure you're satisfied than himself. The rest is just window dressing...

Was 'nearly getting divorced' fairly recent? Do you think he doesn't care if you orgasm?

Very few women have PIV orgasms. You might be chasing the unobtainable. Provided you have an orgasm, does it matter how?

take time to enjoy each other with whatever feels right, with no inhibitions- its fun.

Well I would be happy with any orgasm that isn't induced by myself... Never had orgasm with PIV so can't say it's my aim tbh.

I would be happy with someone who will take a bit of time for my pleasure and will succeed.

Communication on that subject... has always been .... very limited.... It's not always good in less emotional charges subject but I know any comment about it will be taken the wrong way (He is the one who said he thought we had a good sex life at a time when I thought it was pretty bad....)

You're going to have to risk it being taken the wrong way or you're destined to a very unsatisfactory love life ad infinitum. If he doesn't care about you enough to talk about it, he is unlikely to care enough to do something about it.