First solo/submissive date, do I wear chastity?

sub2femdom

Male
From
PA, US
Hi all,
So I haven't posted here in a long time. I've been wearing chastity more and more as time has gone by. I have a nice steel cage with an internal lock, so there's no padlock banging around and the cage fits snug. It's not the best cage, but it works well and can be worn for extended durations.

So, I've not been playing in the lifestyle much since the pandemic, but a bull reached out to me and wants to meet. I'm already iffy on meeting just guys without a woman present (I'm bi but prefer women be present generally). Usually 99% of the solo men who reach out to me are super aggressive or tick a bunch of red flags in their first two sentences, so it's common for me to decline. All of my play with men so far has been at sex parties with women present, and all of my bi interactions with them have been me giving oral to them.

I liked his approach and laid-back attitude, and agreed to a meet/date on Saturday night, and I'm unsure about the chastity cage.

My profile (on the site we use) I list enjoying being put into chastity, but I leave it ambiguous simply in an effort to not push away anyone who might not be into it. I did mention chastity to him in a chat, but he didn't really comment one way or another on it.

So I'm definitely bringing the chastity cage on the date, but I'm stuck on whether or not to put it on early and show up in chastity, or whether to show up unlocked and then present it as an option. I am open to being 'released' and letting him do whatever he wants with my cock, including orgasm if that's what he wants, but I'm expecting to experience anal, and I really want to be in chastity when it happens. He's indicated to me that he does want to top me.

For me, this is a definitive dive into the sissy side of CD/Chastity and I'm super excited to take this next step.

Any suggestions on how I should approach the chastity cage?

PS - for what it's worth, he does want me to dress up in full sissy outfit if/when we play.