Just as the title states but idk how to bring it up to him and the like.

Make it real obvious you want to jack off, when your checking out a magazine or show some phone porn. The more obvious you are you will get a feeling for his reaction. If he agrees about something being sexy or hot, start grabbing your dick on the outside of your clothes and say something like you can't last much longer without handling business. Maybe he will slip right in and both of you can jerk off for the first time together. Once the first time happens I'm sure it will cum easier next after next. Or be up front and just ask him. I would prefer a buddy being up front about jerking off with me, on the DL

Being upfront is kinda risky if you ask me. What if he says no and tells someone about it?

I had a friend in my teens, that would come right out and ask you, "Do you like to jackoff?" I can't recall ANYONE ever telling him "No"........
I can remember him asking ME that when I was a sophomore in HS. It happened about 15 minutes after we had first met and MY immediate reply was "FUCK YES" ! ! ! !
We remained jackoff buddies (and fuckbuddies) for the next 7 years.
Earl

I have a co-worker for whom I have the fking Hots!
Even to JO with him would be a dream come true.
But for now I can only just drop him a few subtle hints
and wait until the time, the trust, the discretion,
the guaranteed uninterrupted privacy, and the convo
are all the right cards in place... AFTER letting
a friendship develop and take its course...
...the next time he offers me a ride home from work
I will certainly say "YES!"