date challenge

Life in my female led relationship is never boring. My Goddess has given me until the 13th of this month to ask a another girl on a date (something I'm slightly terrified of) i will be in chastity like always. She has upped the stake tho. If i ask a woman and she says no, i get 2 more months locked up with no relief (it's already been 3) if i don't ask anyone, i get 3 more months. I have no idea where to start.
So....... Any sexy Michigan bbc lovers interested in dating a well trained, respectful, chastity boy for a night? E could end it with some cuckolding fun of course!