Female led relationships discussion

“First off, a belated Happy Birthday to Mistress Watchful.

I have a friendship with this Lady that is mostly platonic (98%). The ‘more or less’ qualifier exists because we’ve known each other for over two years, yet only had sex once—about three months ago when she was slightly intoxicated. We are both single, and I believe—and am fairly certain—that she still has feelings for her ex-husband, despite him being quite horrid to her (notably dumping her right before their wedding).

We talk frequently on the phone and get along wonderfully. After a couple of glasses of wine, she opens up nicely. The other night, she mentioned going out with a girlfriend later in the week but wasn’t sure how she’d get there or back home. I offered to drive her there and pick her up (likely around 1-2 AM), which delighted her. I suspect she might have brought it up on purpose, knowing me well enough to guess I’d offer.

However, she said, ‘I need to tell you something: don’t try to kiss me’ (though I always want to). ‘If I WANT to kiss you, I will.’ I immediately agreed. This seemed to surprise her a bit; she replied, ‘Okay, that’s good then.’

Here is my dilemma and what I need advice on: I am currently wearing a CB3K with the smallest 40mm A ring and experiencing severe Penile Orbital Indentation (slightly filed down). My last orgasm was on March 18th. Should I keep it on, risking that she might discover my chastity when I pick her up? If she does find out, what should I say if questioned?

She has absolutely no idea about my sexual deviation, though I think she wouldn’t be too shocked. Naturally, I would feel highly embarrassed since, like most people outside this lifestyle, I appear very vanilla in public.

She works full-time and has mentioned on a few occasions that ‘I could do with a slave’ and more recently, ‘I need a maid.’ However, I believe these comments were innocent; she probably doesn’t have much notion of the broader world of FemDom or BDSM. Still, I don’t think it would take much to bring out her dominant side.

Another complication is that she has two daughters (19+) living at home with her, so privacy could be an issue.

Thanks.