Did this for the first time with my buddy a few weeks back. He was a bit hesitant but I made it a condition for sharing new pics of my wife, who he's obsessed with. We were jerking next to each other sharing a fleshlight and I just went for it and reached over to guide him into it after I warmed it up.
Actually feeling his size and girth was incredible and I needed my entire hand to wrap around his shaft. He barely even fit into the toy and constantly pulled it out of the tube. Meanwhile I'm rock hard and put on a used thong to feel like a real sissy cuck while he just used his thumb and finger to stroke my skinny little cuck cock peeking out
From there we frotted and compared cocks before doing a TP roll test when he didn't believe that I would fail. It didn't even fit over his head despite his shaft being even thicker, while I had room to spare. Despite this he told me he was still jealous of me and that my cut cock looked perfect and got to fuck my wife. I responded by telling him I jerk to his thick uncut cock tributes and wanted to worship and swallow him. Sadly he wasn't ready to go that far.
I ended up finishing in the fleshlight we was using on me while I stroked his shaft and imagined him stretching out my wife. I had to leave then, but he eventually admitted he cleaned my cum out of it before finishing second. A couple weeks ago he admitted he still JOs to stroking me and fantasized about cleaning cum off my cut cock and asked for a pic of me hard
Long story short, absolutely amazing experience making new fantasies and next time he'll let me worship and swallow if I let him do the same while sharing pics of me in my wife.
