Measure diameter of largest object (cucumber?
), you can insert into asshole. Find object (dildo, cucumber, eggplant etc) thicker for 0.2-0.5 inches. You have one day to insert it and next 3 days insert it in asshole at least for 30 min.
If you cant insert in first day, keep trying next day. But in that case here is punishment: repeat the tasks with "peebottle", but for now fill the bottle with vomit.