Hi Chloe, well if he knows that you cross dress, and seems to enjoy your company, by all means go out as his girl /friend, rather than his actual girlfriend .
I just wonder what his actual sexual orientation is.!!!.
Does he think it’s a fun idea as a friend, or secretly is he drawn to you sexually.
This my concern since he wants to be alone with you.
I think I would play the part of a girlfriend with him, with in a group of you going out together for a night.
The key I would be looking for is his sexual orientation, thats part that keeps popping up the red flag, is he looking for an experience, as you are, but at a different level?.
Sorry don’t mean to be negative, just doesn’t sit right, somehow. Lol Amanda X
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