I dunno man! It sounds so risky. I would be devastated to lose him as a friend and I don't want him to be weirded out.
I THINK it would end up being ok, even after he shot me down (if he did), but I dunno.
Every time we do it, things get a little progressively farther. But I mean sharing the fleshlight is by far the biggest step.
It started out just being in the same room watching the same porn. Then we'd talk about the porn as we watched it the next time. Then the time before he BLATANTLY started at me for more than just a couple seconds as I jacked off (I noticed out of the corner of my eye he was staring, it's not like we were locking eyes watching each other). Then last time we were sitting 3 feet away from each other taking turns fucking a fleshlight and seeing who could cum the farthest.
I dunno. This has me all messed up in the head!
The fact that you guys even had a contest to see how far you could cum is a bit homoerotic. Don’t get me wrong; I’m jr high/HS, before ever being w a guy, I jerked off w some of my best friends, but there wasn’t anything sexual about. However, it was just about watching porn together and getting off. The fact that you shared a Fleshlight and were making a game of it, and especially, if he was looking at you, there’s something deeper going on.
I did notice this post is a few years old, so I’m very curious as to the ultimate outcome, but it’s more than I’ve done w my gay friends. If he is str8, it would definitely seem like he’s at least curious. With my straight friends, there was absolutely no looking at each other at all. My first time w a guy was my bf, and it started off as jacking off together, and he ended up “dating” me to take over and jack him. So, if he’s paying attention to anything other than the movie and getting off, it would definitely seem like there’s something more going on — even if he doesn’t totally realize it.
It might be worth it to, when you hand it over, to just say, “hold on, let me try something”, and use it on him. If he’s ok with that, after a couple times, ask if he wants to try a real mouth. If he’s not ok w you moving it on him, that would say a lot about him, and all you have to do is play it off like, “I’m so sorry, man; I just thought it would feel better/more real.” If he truly is your friend and you’re already jerking off together (and sharing a Fleshlight), it’s really not much of a leap or risk at all. It’s honestly the next logical progression.