You ask if it's OK to wish to be a pretty girl, but you write:
*** Now, 7 years later, I continue to try to make Sherry MORE attractive, erotic, and feminine appearing TO ME!***
First, it's OK to wish... But, wish for something within reason.
In this instance, if you wanted to look like a pretty girl and you were an average crossdresser, you'd shoot for doing the best you could while using the same tools most women use: clothing, hair, and makeup. If you were TS or TG, you'd go a lot further to alter your appearance, but you'd keep working with the basics, or, to the basics.
Now, ask the right question for your activity:
"Is it OK to wish to be a pretty girl and do all this - fixed masks and so forth - just to get my rocks off at my reflection?"
Sir/Madam, those are your rocks. Do what works for you. Just don't confuse your sexual fantasies with everyday reality - that would be unhealthy for you. Do what you need to do, put the stuff back where it goes, continue with your day.
So long as you can do that, no harm done to anyone. In fact, from what you say, it rather energies you as a person. That's probably a good thing...
You mention that you're on this forum a lot. You seem to be well received. I would suggest you do what you like at home, and, when out, present as any older woman normally would.
As grandma used to say, "I'm not much, but I'm all I got."
We loved her anyway.
