imo @ 5:00 he realizes he cant pull his cock out if he was a successful busness
Assuming that's not a tranny (have to be careful on GB, and those feet seemed biggish) if he was massaging her feet @ :50 he would have said fuck it and gone for it.
Love the ass-slapping veiled as a massage technique around 7:15
I didn't realize while watching PornHub that "Massage Creep" actually had a legit side biz.