She said I gave her the impression of being organised and in control so I used that as my chance to mention my chastity cage.
Well done bravely taking advantage of the entry point she gave you! Few do it as well as you did.
She burst out laughing at that and said she could “just see me in one of those things”. So I told her she would be in control of the keys, she asked if I was wearing it right there and the answer was no, obviously. “Shame” she said. She’s curious about it, not a definite yes or no, and we arranged a third date and I think she’ll be disappointed if she doesn’t see my cage. So next date looks like decision time.
It's wonderful that she treated it both with humour and interest.
She won't have a definite view of whether or not she wants to enjoy your chastity until she knows more and has a taste. And remember that with a normal date she will also be wondering how far she will go with you sexually - and with this she wouldn't have been sure either.
I wouldn't have said that "She would be in control" because that's jumping to a conclusion that you will be in a relationship. I would have said "I would like to give my next partner control over when I wear it" which if she is interested she will read as "give me control" but if she is unsure you are not specifying her.
For example, at this date if you loved giving oral sex you might say "I love to give oral sex so I hope I find someone who likes receiving it". You would never say "I will give you oral sex".
It certainly sounds like she would like you to wear the cage to the next date. Rather than just move ahead casually I recommend that you get her to confirm her wish so that she is in real control.
Send her a message saying something like:
"With a date it is important for me to do as my date wishes, so please tell me whether you wish me to wear my cage next time we meet or whether you prefer I don't. Your wish is my command."
If she makes it clear she wants you to wear the cage then you both know and feel that the cage is on because it's her wish. That adds to the dynamic.
Of course if she wants to see you in your cage next date that will be amazing! And you are then at the stage where sexual possibility can be discussed.
Let her know that if she wishes she can have you keep the cage on and you can go to bed for a cuddle and more. That you like the idea of her having as many orgasms as she wishes and you having to wait until another time. Makes this about her enjoying new pleasures and not about you wearing the cage.
My gut feel is that she may very much like the idea of you only being erect when you are with her and she allows. And you only every having your erection touched when she plays with it or allows you to do so. This isn't about you enjoying denial. It's about you making your sexual pleasure something extra special that is only enjoyed with her.
If you go somewhere private start by offering her a foot massage. If she accepts sit at her feet and do this. This is a great way to talk whilst giving her a sensual pleasure. The position also has her feel that you are serving her. This is when I would tell may dates that with what I do I fulfil all their sensual and sexual wishes. So if she ever wishes for a massage then I'm happy to do this. I also say that if she wants to get a feel of how this works she can have me undress. You can add "you know that it won't go any further than you want as I'm wearing the cage".
Given her interest it's very likely that you will eventually be naked except for the cage and sitting at feet giving her a foot massage. She will be fully dressed. So it's while you are at her feet that you can talk about going to bed and just her having an orgasm.
Remember during the foot massage to also talk about other things. The idea is to make it feel normal for you to be doing this, and not wearing much, whilst having a conversation.
If naked wearing the cage you can say that you hope that one day she will have you take the cage of so you can enjoy being hard with her. Add that you are only allowed to play with yourself if she says, and that just because you are naked and aroused doesn't mean she has to touch you. She can enjoy just looking.
If she does have you take the cage off then with nerves it can be difficult to get hard. I tell my date "If you want to see me hard you can say Display and I'll stand up next to you and gently play with myself for your viewing pleasure. You don't have to touch me, and it's powerful the first time if you decide to just look. And asking me to Display isn't really using your control as I think it would be fun to do this. Your real control is at the end if you say "thank-you, sit back down and continue with the foot massage'.
I think of this all as drawing out a map of next steps. It's totally up to her if she wants to take any steps and which direction she goes.
The other thing is she can go off script. This is great if it still fits the dynamic you want.
For example, if a date wanted me to cum I would say that I prefer not to cum until the relationship develops. Then I will only cum when she wishes.
All of this can take an hour or more. It's an amazing way to get to know someone.
And though you could show her the cage as a bit of fun, that doesn't get her feeling that you really are giving her control and that her control is real.
To get an idea of how this all works (but without the cage aspect) the true story of my first date with Princess Ada is
HERE.
Just remember not to focus on the cage but to focus on how what you do can make things wonderful for you both.
I REALLY look forward to hearing about your next date.