We've been friends with benefits, off and on, for almost 3 years and have both dated other people in this time. We liked each other and hooked up when we first met so we've always had a "flirty" friendship. We've done everything together except have sex. He's jokingly brought it up a few times but he's never tried to pressure me into it. Recently, we had a talk about actually sleeping together and he was kind of surprised that I chose him to be my first. He seemed a little hesitant but he said he doesn't mind as long as I'm 100% sure that I'm ready. He was my first for giving/recieving oral so he knows I'm cautious about who I'm physical with.
Do you think that might have scared him off? I've mentioned a few times in the past that I wanted it to be special and with someone I'm dating or seeing, I wasn't suggesting him in particular, it was just a general statement.
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Well if he's also your friend i think it's not weird for him to think of your future. Like he might be worried you'd regret it years down the line and he'd feel bad0