Talking to a straight school friend online and I am starting to think he may be interested...

My friend Sexyman [we will call him sexyman] used to go to school with me till he dropped out and got his GED. While in school he would say, "You are the only boy I would call cute" he would also sometimes call me pet names. And this one time he lowered my head into his lap and pet me gently. I was blushing a lot... We were also in the library. I don't think he is shy about people thinking he is gay, is that good? Fast forward to my junior year, he dropped out, has a job, and we still talk on Skype. First off let me tell you he is hot... Like tall nice defined muscles. He constantly sends me photos of his muscles. Then one day he sends me a cute picture of a femboy in chastity [He knows I want to be a femboy] and asks him if I like it and I say yeah. A few times we talked about fucking and me sucking him off in cute girls clothing. Though he seems like he constantly goes back and forth between wanting to mess around and telling me is straight. I think he is super sweet and wants me to cuddle me... Oh I want him badly. Though the only thing I dislike about is his weed use and dropping out. But don't be fooled he is speaks and argues very intelligibly which I love. All I want to know is this. Should we meet up again and try? Also one more thing I am a virgin while he has slept with I think a lot of girls.