Ok so I wore pretty much the same outfit in this thread:
Finally first outing!
but wore a black sweater instead, but my coat was on both times so you couldn't really notice the shirt...
ANyway this time I did take notice a couple curious glances but no remarks or awkward stares, just like oh hey he's wearing heels no big deal...
Oh and tonight I went to the same place with my friend and she and I wore pretty much the same boots only her heels don't taper and are an inch taller overall... I want her boots and we are the same size so she said one day we could trade...
Anyway back on topic! Overall I felt much more calm about the situation like you all said and more natural... I hope that after enough outings with her I can do it on my own as well as go to school!
Goodnight everyone and thanks again for all the previous comments and support!
Jeff