This is has way more of a background, a much longer and more complicated story than what I'm presenting but wanted to get a little off my chest (sorry if it's long):
My first and only three some occurred with my best friend and one of my exs, but we'll get there.
Our friendship goes way back but we always have had sexual undertones. The first time I saw him naked was in hs and another friend and I walked in on him jerking. We all joked about it later and throughout the rest of hs I 'accidentally' walked in on him changing or getting ready to shower – those type of things several times. I've shown off my cock to girls in front of him. Other then that, we never jerked together though it was always something of interest to me. Sex topics were something we always talked about often, but other than the mild and wild escapades, we never had contact or were naked at length together without girls present.