Update: Visited buddy and shared some new content. My wife has stopped being shy and is happy to pose for me when I take pictures, so I got to share some incredible pictures. My buddy literally took my phone and unzipped his pants to start stroking his girthy half chub to my wife.
I took my pants off to show me wearing a set of her used panties then started stroking his girth while he reciprocated stroking with me. After some size comparisons, frotting, and rubbing cock heads, he brought out a double-sided fleshlight
He was so thick that I had to guide his cock and push him in the toy before stroking him with it. He guided me in on the other side and I started stroking for the both of us.
This whole time he's enjoying pictures of my wife and I felt his cum on my side of the toy. I quickly switched sides with the toy and slipped into his load as he stroked the toy on me while going through my wife's pics.
My little cuck cock was rock hard in his side of the toy, pulling his cum out on my shaft and under my cock head while I needed my whole hand to hold and stroke his girth. I came hard in the toy imagining the size I was holding and stroking was stretching and filling my wife deep.
He ended up cumming in the toy twice after before cleaning the toy out