There's a huge difference between being ashamed of your sexual preferences and your sex life being nobody else's god damn business.

That being said, I find if laughable that the op considers himself "infosec" savvy but when it came to his sex life made such a glaringly obvious mistake. I'm not saying the woman who extorted him was in the right, but touting yourself as an infosec guy but opening yourself to the oldest trick in the blackmail book is pretty funny