So I've known this boy since before I came out as trans. I think he expected it, though. I met him at school at 12, he was a flamboyant, troublesome transfer boy and I was a anxiety-engulfed loner. I was a scared to take risks and he took to many, he spoke his mind and I kept my mouth shut. We brought out the best in each other, though we both weren't perfect. He ended up kicked out at the end of grade 7 for smoking and fighting on school property, but we still made contact after this. He was always a ladies man, but I was never a lady. I was just another guy just happened to have tits and a cunt. We walked the Appalachian streets and smoked flavored cigarettes and played video games and talked about guy stuff, like how your boxers got bunched up when you ran or how you had to act "different" around girls. It wasn't an act for me, it was honest conversation.
I came out to him over a spliff on his back porch last year. He'd noticed me dressing more masculine lately, and he'd noticed my chest being much less apparent. To say he wasn't surprised was an understatement. I had chest length dreads at the time, and that same day he helped me take them out and cut my hair into more of a manly-type style. He'd never acted so genuinely caring in his life, I knew it was in there, it just never really showed. He took some money out and bought me an actual binder offline that day, too. A great friend.
So we went on as guy friends for a year. We did our usual shenanigans while I tried to balance partying and sleepovers with school and my straightedge friends. I'd never thought of him as anything but straight until last Saturday. His mom is essentially a closeted drunk, so she never really gave a shit about what we did. She was passed out in the kitchen and we were [...] in his bedroom, watching Rick and Morty on his TV. He slung his arm around my shoulder and told me he liked me, a lot. I said the same thing back. We kind of knew what we wanted at this point- physic-type shit it was. We just kind of started feeling each other up, and while I was expecting him to be super rough, he wasn't. He was very nice to me and made sure that I was OK with what he was doing. I let him get me completely nude, as well as himself. He used protection and everything, and asked if I had ever done this before, how I wanted to do it, etc. [...] it didn't hurt much more than the couple dozen hickeys he left on me, and actually started feeling really good. Like, my head was in the stars and I was making all these noises, throwing my head back and grabbing his hair. He threw in some oral as well. Long story short I lost my virginity and it was great.
Until the morning after. I woke up remembering everything, and feeling absolutely shit about having somebody see my body like that. It's not like I regretted it, though. I enjoyed it, he enjoyed it, we had a good time. But I felt just so, so dysphoric. I shook A awake and told him how I felt. Though groggy, He said he would never judge me for what my body looks like. He understood how I would feel dysphoric, but he still saw me as a man no matter what. He got dressed and got me some makeup for my bites and some coffee, and after a few hours I was driven home.
I still feel somehow guilty for enjoying penetration in context. I feel that, as a boy, I shouldn't get turned on by that sort of shit. What the hell do I make of this? I know I'm 14, and I know it's not a good idea to smoke/party/have sex at that age, but what happened happened. I don't know how to feel.