Jack's come on quite a journey with us over the years, he's always been one of the more easy going and experimental guys, but I wasn't sure we'd ever see him being fucked - well, Tyler is the lucky lad to get to experience taking Jack's anal cherry! The shoot starts with some rough and tumble - the two straight lads are wrestling each other and soon start trying to rip each other's underwear off! It can only lead in one direction - getting hard and getting their mouths around each other's substantial cocks! But there's no putting off Jack being fucked - Tyler lubes him up and slides in, fucking him gently from behind and eventually getting quite forceful, Jack staying rock solid throughout. Jack shoots a really thick heavy load all over his leg, before Tyler pulls out and cums over himself!