Chastity and orgasm denial discussion

I am currently dating a young woman. Everything is great, but soon things might get sexual. I want to tell her about my interest in chastity and about my small penis. She seems vanilla and I don’t think she is ready to be a keyholder. I don’t want our first sexual encounter to be traditional, that is me penetrating her. At the same time I am afraid to scare her. What should I do?

I would have a discussion which gently brings up the subject. Maybe asking her opinion on 50 shades of grey, that should give you a rough idea of where she is on the vanilla to kink scale. Maybe try clarifying what you mean by sexual, it is normally describing penetration, if this is not what you are looking for, you def need to find out whether she is interested.