I bet that it wasnt even Jesses idea to stuff himself. But Zenyatta‘s fingers just kind of wormed their way into his hole and it felt really really good; and McCree def isnt a man that has problems with masculinity/showing he‘s a big toughie; so he def lets Zen stuff a plug into him
OR EVEN AN ORB. Would look nice to see his hole bloom open and give a glimpse of glittery gold inside