One of my closest friends has seen pretty much every inch of mine and in return I've seen pictures and videos of pretty much every one of his partners. He's going to marry the woman he's with now, so our sharing has pretty much stopped.
I had started to build a similar kind of 'relationship' with another close friend, but the pandemic has put that firmly on hold. Looking forward to tactfully trying to pick up where it left off when the opportunity arises.
Funnily enough, it stemmed from him wanting to see a picture of my dick
He's straight, but he'd heard the rumors over the years and straight up asked me about it one evening when we were out having drinks and the conversation had turned to his current lack of sex. I asked him if he was absolutely sure he wanted to see it (there's no going back from that hahaha) and he said he wasn't sure but he just wanted to see it and know for sure
The most recent picture in my camera roll was of my wife giving me a handjob with both her hands together at the base and the rest of my dick coming out of the top. Btw, I'm not like massive by porn standards, I can manage 8 inches on a very good day and my wife has small hands
So after his initial compliments he said she has a great figure. That was my cue! I agreed and immediately started swiping back to show him more. He got to see a few of her fully nude and posing for me, along with a short video of me taking her from behind and shooting a big load up her back. Unfortunately we were in a busy restaurant and it wasn't really the place to be doing this, with people constantly walking past the table, so it ended there - him with a look of shock on his face!
This was shortly before the pandemic, so I'm hoping that it happens again once things open up.