How comfortable do you feel talking about chastity to someone you are attracted to?

I've always wondered if broaching the subject of chastity is as difficult for women as it seems to be for men.

I haven't ever had much trouble talking about it. I usually feel more excited at the prospect than awkward. Although my experience is limited to discussing my fascination with five women and it went good each time.

So for me it's always led to a fun and interesting conversation. The difficulty I've had has been that no one I've discussed it with has been as fascinated with chastity as I am.

Right now I've got a friend who has been kind enough to decide how long I go in between O's. She's been deciding for around a year and a half now but she doesn't have a passion for it. Even after all this time I haven't felt comfortable really opening up and sharing the struggle with her so I don't know.

I might look into getting involved in someone locktober challenge this year. 

So how comfortable are you introducing someone to chastity? Have you had any spectacular failures or talked to anyone who loved the idea and ran with it?