JerseyguyMC said:
May I ask a question?
... What are we doing wrong?
And, she we even be pursuing it?
So far, everything we’ve done has made sex better.
Is it a mistake to go further?
I know that the obvious answer is that it depends upon our mutual goals.
We aren’t looking for some meaningless aesthetic.
We’re looking for a heightened experience....
Pardon a very late response; I don't know why I haven't seen this before tonight.
In any case, I don't think you are doing anything "wrong".
It's obvious that it may take awhile to accomplish your goals, so I would try what may work best to achieve them.
A speculum may give you 'instant' results, if that is a need. It still remains the best tool for inspecting the inside of a woman's pussy, but they may not be practical for frequent use.
Something else I'd recommend is exploring her g-spot and erogenous zones. Find out what makes her tend to cum with a lot of force, particularly if she also produces an ejaculation (squirting). The idea is to create a deep, hard-throbbing orgasm that naturally makes her pussy open/close with each clench/relax.
Lastly, stretching her pussy will likely be the key to the whole process. By all means, give her everything she can take, and then a bit more. Use dildos and other toys in combinations, including your cock.
If you're not fisting her, you need to start. If she is already taking a fist, then you have to work on getting your other hand inside her pussy at the same time.
Whatever you are able to do, you must do it often enough, for long enough, to break down her pussy muscles. Given rest, they will always 'heal' themselves, and has another benefit of increasing their strength, thus making her pussy grip as hard as it ever has. Maybe more!
Anything you do, whether it's sexually-related or not, that is pleasing and nurturing to the both of you, will never be a mistake.