Wearing chastity cage on a first date?

I know it's already past and likely just as well you chose not to but...
Boy does this fuel the 'ol
"what is that?!" She exclaims
You reply "It's a cock cage and my ex has the key"
"What?"
"Yeah, she says just because we broke up doesn't mean I'm giving up the key. You introduce me to your new girlfriend, when you get one, and if she's serious I'll pass it along to her"
"Really?" She says, looking reflective, then raises her eyebrow. "When can I meet her?".

Bam

 

I would make sure "nothing happens" for a good many dates yet.
Everyone is in such a hurry these days. it takes time to make something special.

 

First dates that end up in bed have generally for me been not quite disastrous but usually involve alcohol and the sex is never optimal and doesn't make a good first impression. I prefer to work up to it over several dates so we're both better prepared, thus for the last couple I've worn a belt so I'm not tempted to rush things. I'm not worried about it being discovered as the dates were via OkCupid so we both knew the other was pretty kinky and it would probably have been a positive thing possibly leading to keyholding, in fact I was once tempted to let her know. Sadly neither came to anything but next time who knows.

 

I've learned the hard way that just showing the cage to a partner is the most unsuitable way to introduce her into this thing. Go uncaged, if things happen between you, talk first.

 

If you haven’t met your date through a kink related way, then I’d say no, don’t wear it.