For purely selfish reasons I like the concept of the woman being in charge of the pace and overall conclusion of the evening, or events.
My scenario goes like this: "I will reluctantly agree to help you experience your foolish cuckold fantasy husband of mine, but on my terms and not yours. First off, you will purchase the smallest chastity device that you can fit into, and after locking it on you will give me the keys to prove your sincerity in this adventure."
"In exchange for this first step of yours I will take one of my own and find a man, or men, that I fancy and flirt and chat them up to test the proverbial waters. I won't tell you who they are, could be your boss, my boss, one of your friends who always has a secret smile for me, really anybody I choose."
"In exchange for that we will go out shopping for some sexy going out on the town outfits, which you, husband of mine, will buy knowing it will be for the express viewing pleasure of a man other than you."
"If you get over that hurdle, I then knowing for sure that you can't possibly be using all this as nothing more than masturbation material, I will consent to allow the man of my choice to take me out in that sexy outfit you bought us. Not to sleep with, yet, just for dinner and possibly dancing as I love to dance and you obviously don't. If by then you haven't changed your mind on this little game, but more importantly assuming I haven't either, (and of course assuming the man I have chosen excites me), I may choose to allow things to go further."
"In exchange for that my cuckold wannabe, knowing men as I do, and studying enforced male chastity as I have, you will be quite submissive by then and willing to do almost anything I demand. You will be doing all of the housework, not because I have demanded it though, but because I wish it. This will also leave me time at night to be going out with any new potential lovers, and also serve as a necessary distraction for your unanswered sexual release."
"If you behave yourself I may actually then cuckold you, but you won't be in the same room because I don't find that exciting at all, and by this point if you haven't figured out that this is all about what I want and not you, too bad for you. If however you've been truly extraordinary on this journey of mine, I may allow you to book hotel rooms next to each other with you handcuffed to the bed in one while my lover and I consummate your cuckoldry in the other, I promising to make as much noise as humanly possible for your vicarious entertainment."
"If we get that far, cuckold, I will then give my chastity keys to my new lover so that he can decide how best to use you in the future, I'm thinking slave, or domestic servant, but by that point it won't be up to me..."
Just something that excites me, hope you like it, Jackie.