My best friend, whom I will refer to as J, and I have been friends since the beginning of high school. First off, I'm gay, and he's straight. You can imagine the flack he caught for his best friends being gay, but he's proven himself to be one of the most loyal people I have ever met. Guy actually get in a fist fight defending me and who I am. We've been inseparable. Where I would go, he went too. Where he went, I would go too. I couldn't ask for a greater best friend. However, things have recently gotten a little... uncomfortable... for me. We both went off to college at the same school, and though we studied vastly different things, we always managed to meet up to study or just play racket-ball/tennis/basketball/whatever sport we felt like. We've always been there for each other. He knows that there's nothing that I wouldn't do to help him out, and I know he'd do the same. Feel free to skip to here to miss the backstory =) So here's the issue: While we've been the closest friends for a long time, it was always understood that we were only friends. That point had been proven over and over again. Not all of five minutes ago I check my phone and see a message from J. Here's how our convo went: J: "Hey Bashful (name replaced obviously :wink can i ask you something and u not get weirded out?" me: "Yeah sure what?" J: "u think you can look at a picture and gimme your opinion on it?" (This isn't the strange part, to be honest. It's not rare for J to send me a picture of a girl we wants to date to get my approval.) me: "Yeah, I can do that." I open my phone and there sits a picture. The message read: "Think these are too tight? I open the pictures, and there sits a picture of my best friend in not but trunks. Let me just say this. We're close, and we share a lot of things with each other, but with me being gay and him straight, it was always understood that anything sexual, or having to do with that region was just not talked about. I responded the only way I knew how. "I thought you wore boxers." His response was that he wanted to try something new, and wanted someone's opinion on them, and didn't know who else to ask. Yeah, I'm thrilled that he's comfortable enough to ask, but now I'm feeling kinda weirded out. This can't be normal, can it? and What am I supposed to say now? I haven't messaged him back cause I'm feeling kinda awkward. Any suggestions? Sorry for the long post but I really can't shorten it up and get the magnitude of my predicament across. help?!