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Concerning your question about #2.. I use a set of five plastic dilators as opposed to seven glass dilators, but I hope you’ll still consider my thoughts on this one!
I would consider not being able to use a larger dilator without insertion of smaller dilators beforehand as normal, and just another STEP on the journey to being able to use a larger dilator by itself. For example, if I were to start with size 3 in my set of five plastic dilators, the step-by-step journey would look something like this:
Step 1: Insertion of size 3 by itself
Step 2: Insertion of size 3, then insertion of size 4
Step 3: Insertion of size 4 by itself
Step 4: Insertion of size 4, then insertion of size 5
Step 5: Insertion of size 5 by itself
Speaking here as someone on step 4, it may be disheartening to think about how I can’t insert size 5 by itself without it hurting more than if I inserted size 4 beforehand. So instead, I think of it this way – There once was a time when inserting size 3 by itself hurt. There once was a time when inserting size 4 by itself hurt. I’ve progressed past those points, though!
ALSO, my doctors told me a very helpful thing: In terms of having to use smaller sizes before insertion of a larger size, it’s not like you’re going to have nothing to “prepare” you when you have sex, either. Sex should have 15 to 20 minutes of foreplay beforehand. In a way, you can think, “smaller dilators before larger dilator = foreplay before sex”. Whenever you feel disheartened by not being able to insert glass 7 right away, just think about how it’s unrealistic to have penetrative intercourse without any foreplay/preparation beforehand!