I know this may be an old post and things may have changed since then.
But let me share with you an exp:
I had almost the same issue, a very close friend who would let me massage him and who would even massage me (he didn't always ask to be massaged, sometimes I used to offer and even insist)
We were sober all the times, and I noticed after a while that he is getting hard.
He used to stay quiet and sometimes even act as if he was sleeping. I upped it up a notch just out of curiosity until one day he got so bothered that it almost ruined our friendship.
We stopped the massage issue for a long while and got back to it recently.
He would massage my back and I would do the same. He very rarely asks for it because he doesn't want to be the one who initiates it but when I offer him a massage he gladly accepts.
He still has a boner on many occasions but I just don't go there anymore.
I gained our friendship back and I am not willing to lose it.
In case he would like to take things further then it's his call and i'll just wait.
I know it might sound different but trust me it began the same way as yours. but i'm not saying that the outcome might be the same.
you have one of two options:
1- Come out to him when you are all dressed up, not in a bedroom and the time feels right and see what he says.(this is the lowest risk option)
2- Try to touch his pubes, apologize if he's not exited and see his reaction or just joke about him having a boner and also see his reaction
It depends how much it's burning you on the inside and how much risk you want to take.
Just don't stay in that grey area for too long. for both of you and for your friendship
is it normal to be gay and massage your straight best friend?
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I know this may be an old post and things may have changed since then.
But let me share with you an exp:
I had almost the same issue, a very close friend who would let me massage him and who would even massage me (he didn't always ask to be massaged, sometimes I used to offer and even insist)
We were sober all the times, and I noticed after a while that he is getting hard.
He used to stay quiet and sometimes even act as if he was sleeping. I upped it up a notch just out of curiosity until one day he got so bothered that it almost ruined our friendship.
We stopped the massage issue for a long while and got back to it recently.
He would massage my back and I would do the same. He very rarely asks for it because he doesn't want to be the one who initiates it but when I offer him a massage he gladly accepts.
He still has a boner on many occasions but I just don't go there anymore.
I gained our friendship back and I am not willing to lose it.
In case he would like to take things further then it's his call and i'll just wait.
I know it might sound different but trust me it began the same way as yours. but i'm not saying that the outcome might be the same.
you have one of two options:
1- Come out to him when you are all dressed up, not in a bedroom and the time feels right and see what he says.(this is the lowest risk option)
2- Try to touch his pubes, apologize if he's not exited and see his reaction or just joke about him having a boner and also see his reaction
It depends how much it's burning you on the inside and how much risk you want to take.
Just don't stay in that grey area for too long. for both of you and for your friendship
Best of luck