I'd put money on anal being a terrible experience for Kev and whoever decides to take that health risk, but think it's 50/50 he'll admit it wasn't great. Gotta keep up appearances. It's not just the prep involved, but you also don't just pound away and hope for the best. Double that with the weird soft wedge dick his girl daddy has, it's going to do nothing for him. I'm sure they'll try toys but with MtF SRS there's a very real risk of rupturing internal walls, although it sounds like Kev's developed a nice padding of keloid armor.