This does sound like a lawsuit in the making. You think she's repressed and not interested.....so you're going to harass her anonymously in order to make her suddenly fall at your feet?

If you're worried enough about the plan failing so hard that you need to take precautions to try and stop any repercussions, maybe it's better to look at the plan from the start, and start far smaller and far safer. If I knew someone who didn't like skydiving, I wouldn't hire someone to kidnap them and hold them at the door of a flying plane. Likewise, if I knew someone who didn't have an incredible sex life, I wouldn't hire someone to deliver them a highly radical and uninvited sexual gift.

I don't mean to sound overly harsh.....but this plan has a lot of ethical, emotive and practical problems in my view.