Friends with benefits? More?

*If you’re judgmental, don’t read this* (:

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Okay, Y’all. As a senior in high school, a friend of mine whom we’ll call B, and I decided that we were going to try a friends with benefits deal. The two of us had always been close and kind of flirtatious. We’ve got a long history dated all the way back to daycare. We did our deeds occasionally over the summer using the pill, condoms, and pull out method combined just to be safe. Anyways, since then, he’s been stalking my instagram. He and I don’t even follow each other anymore, but he views a story I post occasionally, or he’ll “accidentally” like one of my posts. I mentioned it the other day over a DM, and he just went “🤷🏽‍♀️😁”. We have been planning to do some more things (😉😉) when the both of us are home from freshman year. He told me I should consider being a little. I’m thinking this is signifying something closer to a relationship. It almost requires a level of comfort and a sense of stability between us. Do y’all think he will possibly bring up the idea of pursuing a relationship? I mean, after all, we did take each others V cards, and we’ve always been flirtatious. Should I ask him about the possibilities or wait for him to bring it up?