I imagine this was probably rather early in Jamie's training. A sissy slave like himself needs to be able to stay in the same position without complaining for a long time, they need to grow accostumed to their bondage gear and diapers and they also need to be able to comfortably hold anything inserted into their tailholes for hours. So everything being taught here is really important for the little sissy slave uwu

Commission for JamieKaboom
Art by ZombiNeko