THIS IS LONG AF BUT PLS HELP IM IN A TRICKY SITUATION IT WOULD REALLY HELP

I broke up with my boyfriend a few months ago to take time for myself and explore my sexuality. One thing I was hoping to experiment with was hooking up with people. My best friend has been known to hookup with people but she's far more confident than I am. I find it very empowering for women to take control of their bodies and their sexuality and I want to experience that. Since I'm so insecure about my body, I thought it would be better to ease into hooking up with someone I already know. However, my guy friends consist of my ex, my other best friend, who is gay, the person who will be important in a minute, for these purposes let's call him Derek, and my friends that Im not super close to, more like casual friends. So pretty much my top choice is Derek, as we're calling him (not his real name but this is anon anyways but oh well). Things in the past have been a bit complex, I've had feelings for him before, and Im strongly attracted to him, but I have no clue what his opinion of me is. Ive been trying to talk to him more in hopes to work my way up to hooking up with him, since he's single and wants to have a sexual relationship with someone. He and my best friend are pretty close, and he has tried to flirt with her, but shes now in a comitted relationship, however they both still openly talk about sexual things, including how hes attracted to her. I dont currently have feelings for him but I cant help but feel weird that they lowkey almost hooked up, since she knows the feelings Ive had for him in the past. I really want to pursue a sexual relationship with him, sort of friends with benefits, but I dont know how and talking to one person about it doesnt exactly give the best perspective. How do I tell him I want to hook up? Should I let my bff be my wingman and let him on to the idea that Im interested ib him? SOS I NEED ADVICE HOW DO I CONFIDENCE