This roulette game sounds fun and I would happily play. The question, "Did Jake get a poz load during the game?" remains unanswered due to the helper's unknown status (since the helper disclosed that he had never topped, we can reasonably assume that he is a bottom and a well-experienced one given the hotel's event, so putting together this info, it's a good chance that Jake received another poz load.), but we know that Jake enjoys cocks in his ass and has even thought that he could be a cumdump. Jake is slowly dismissing the standards he once held for sex. His body is telling him the pleasure is too much to disregard. (His fear of STIs is disappearing, and his want/need for pleasure and sexual satisfaction is growing.) What's next for Jake? Only time and the next chapter(s) know...Looking forward to it!