@Vin I can relate to a lot of what you had posted.
I've had crushes on guys all the way back to middle school, just as I had crushes on girls too.
I was the same way, and I was kind of shy around both boys or girls whom I had thought were cute and had 'crushes' on. I was usually able to get past my shyness with the boys more easily though I think because I found the girls more attractive, and a bit more mysterious.
My crushes on boys when I was high school age were mainly on smaller more 'effeminate' boys, such as myself. I was more attracted to 'cute' girls as opposed to 'sexy' girls. I had a 'type' that I liked regardless of either sex.
Although I 'liked' more effeminate boys, my main fantasy always was taking it in the bottom from them. I could see myself or imagine myself being on top too, but primarily I fantasized about being penetrated. With girls I fantasized about vaginal sex and mostly about making out - the hugging kissing, heavy petting parts that I really didn't fantasize as much about with boys.
So far, my only play with another guy has been in a fetish situation that has happened a few times with the same guy, and that's been quite some time ago. For going on a long time now I have been more and more receptive to the idea of bottoming for anal sex, to the point of craving it. Unfortunately though I have been having more health problems having had started later last year. My latest - a hemorrhoid that bled recently that I had to get checked out because I am on blood thinners. My PCP nurse practitioner says it should be fine but she's scheduling me for a colonoscopy. In short, I wonder if my fantasies involving anal sex will ever play out.