It’s kind of a long story, but here goes. I’ve been friends with a guy for about 6 or 7 years and by now, he’s become my best friend. I’ve always considered myself straight, and so has he, since we both have dated and fucked girls.
For as long as I remember, he’s always been kinda flirty with me. There was a time in which we would mess around witg who got the bigger dick, and he once sent me a snapchat with a mark on a ruler just to prove that he got a bigger deal. That same night, we were talking over the phone and he said that he was getting fit, and without even asking, he sent me a shirtless snap of him. After a few minutes of silence, he hung up, so I guess he kinda felt uncomfortable.
Apart from that, we’ve always been kinda touchy. Our legs have made physical contact several times, we’ve wrestled (and he’s put his crotch over my face), we’ve seen each other in boxers (he once took a pic of me but then deleted it) and so more stuff. Lately he’s been joking about jerkin off together and even sucking each other’s dick. I can’t say that I’m reluctant to do it, since I am a little interested in doing it, ngl. But I feel like it would be super awkward and maybe he is just messing around. Besides, I’ve never kissed or messed around with a guy. What should I do?
He is probably asking the same question you are asking in another forum. Probably he is testing you too to see if you are into more things. I have had several friends over the years with whom I have jerked off, each his own, and some others have touched my dick and I have touched theirs. I would say that in my experience he is dying to try it out and has given you signals but he is as afraid as you to be too forward. I am not of the idea of being too stiff about it saying "I want to experiment with you" in this scenario. I think that is going to backfire, because if he is playing it subtle, then you are going to totally blow it by being too explicit and unnatural. I would say to take it up a notch in the hints department, up to a point where you can abbort mission if you see he feels uncomfortable. If you ask me, there is plenty evidence of two things: 1. That even if he is not actively trying to jerk off with you, he would be totally ok with that if you were to bring it up, or 2. He is as eager to do it as you but as afraid to screw it up as you, that would be why he is taking it slow. In either case, he would jerk off with you. I have had friends in both camps and it's cool to finally make the jump. One of my best friends was on the first scenario. When the opportunity arose, or better said, when I encouraged the opportunity, he was totally cool with it and ended up in us jerking off. We do it semi often.
Some other friends are on the second camp, that I see when talking about sex, they start hinting on me taking out my cock, so I oblige, and then it evolves in a jerk off session. After the fact some have told me that they always wondered how big my cock was, telling me that they were curious ro do it. Whenever they come to my house, they suggest to rub one out.
So, you might be wondering, how do I bring it up? There are some things you can try to test the waters and see how he reacts. You must be a bit bold. If he doesn't take the bait, then you can shrug it off and make like you were just horsing around. One that works for me is saying "dude, you gotta see this". You put on a porn vid that is not fetishy, just normal porn and you make comments like "dude, this vid is freaking hot. It made me rock hard the other day". You put it on and try getting hard. Once you have at least a semi you can say "dude, I am getting hard. Pretty good vid huh" and try to add a little laugh and grab your bulge and show it to him. Like "here's the evidence I am getting a boner". Then you see how he reacts. As long as he doesn't say "dude, wtf" or he looks visibly uncomfortable, then you can proceed. Try rubbing your bulge slowly, like you are enjoying the vid and look confident, like it's a natural extension of the trust between you. In my experience, at this point, most friends would start giving a rub to their bulges as well. It's like they see me do it, then they feel it's ok for them to do it as well. From there you know what to do.
Other thing that has worked for me is playing with the competitive side of a dude. I would say "dude, the other day I was rock hard. It was huge man. I bet way bigger than you". You start the typical teasing with "I bet I am bigger man, You've got nothing on me" and seeing how he reacts. Some outlining of your bulge might help. Sometimes I would toss a bet to sweeten the deal.
Another thing I tried and worked was changing in front of a friend with a semi in my boxer briefs. I made sure he noticed with a comment like "dude, look at this". You can take it from there
Hope this helps. Sorry for the lengthy response
