My best, closest guy friend and I would jack off together literally hundreds of times throughout junior high, high school, college, and a little after that. He was straight as an arrow and very athletic - on the high school track and swim team, muscular and with amazingly huge thick feet. It became a very regular thing for us to end up bare-assed naked and jerking off to porn together, really some of the happiest experiences of my younger life. We never touched each other, but otherwise had no secrets - always naked around each other and openly staring at the other jacking it, sharing all of our stories of our sexploits with girls and our raunchiest porno fantasies. It was amazingly intimate. My dick was a lot bigger than his and it really interested him, but he'd gotten vastly more action than I ever did and so always had better dirty stories to tell. We did this from about age 13 to 26 so we got to see each other grow up while doing it.
The furthest it ever went was a few times we'd talk to each other as though one of us was a hot girl in our class - think of it as phone sex but with the other person in the room and only pretending to be a girl, i.e. "(in soft girly voice) Oh did you like that tight shirt I was wearing at school today? Did it show off my big tits? Do you like my big tits" "Oh yeah, Sarah (or other girl's name), I want to suck your big tits, I'm jerking off right now thinking of them, I wish I could fuck you so hard..." "Oh yeah, (my friend's name), my pussy's so wet for you, I want you in my pussy, you're so hot and I'm imagining you fucking me right now..." or, "(hot girl's name), I'm so horny for you, you give me the biggest hardons," "I know, (my name), I can't believe how big your dick is, I'm sure it'd make me feel so good, can you jerk it like I'm giving you a handjob? it's soooo biiig..."
So under the context of pretending to be girls, we each spent a fair amount of time talking about how hot we each were, what great dicks we had, and how much we wanted to suck and fuck each other.
Yes.
And yes, we never physically acted on it, which I regret for its stupidity. At 16 I'm sure beyond a doubt it would have been fine - I think we were each just too chickenshit to push things further.
But I believe I've discovered the cure for Alzheimer's, because I'm certain I will never, ever, ever, ever forget the sight of this 16-year-old straight jock, naked on my parents floor, eyes bulging even more than his dick as he stared at me also jerking off, while girly-voicedly calling me a big-dicked stud and begging me for the hardest fuck I could give.
Once when we were in our early 20s he asked me if I'd fuck his then-girlfriend (now his wife) while he watched. Of course, he didn't say it as straight-out obvious as that, it was all roundabout, and we were both drunk, so I didn't really figure out what he was saying until after I'd lost the opportunity.