Ok - OP here.
I saw him last night. Although not the porn scene I was hoping for - it was a little “different” massage than before.
If I thought we got close to the line but never crossed it before - well we got closer.
We started with some small talk. The other day I realized I don’t think I have ever out right said I was gay - I am sure he know it. So this time I made sure to make it clear in the conversation.
The roomset up was more of an area than a room. He said he was working on a screen but, I could still see him when getting naked. I tried to see if he stole a look, but I couldn’t tell.
The massage was amazing as always. Same accidental brushing as before, but with him wearing loose basketball shorts with obviously no underwear vs scrubs - I could feel his cock as he would drag it along my arm, leg, top of head. I thought I noticed him getting hard, but that might have been wishful thinking. I was too chicken to touch it. But, It was so fucking hot. I was hard from the minute I got on the table. I made more noise that usuall, especially when his dick was resting on my thigh. Ha. I am sure he knew I liked it.
He has always been casual with the sheet, but he was even more so this time - If it goes the same next time I will try and make some joke about “just getting rid of it”
I guess all in all it was the same great massage - a little freer. I feel I could push the boundaries a little bit more.
Thanks for all the help guys.
What do you think for next time? Push things or just relax and see?