The enjoyment was clear to the seasoned dom that wondered just how much punishment this really was. Then again if Caden did something truly bad and needed to be put in his place he had plenty of creatives ways that he would hate. Even a caning that could be fun warmed up on a high would feel terrible out of the blue and cold though normally he didn’t resort to such levels an he doubted Caden would be the sort of bratty sub that would earn such treatment from him.<br/><br/>So instead he got lost in the sound of the flesh being smacked and the noises that poured out for Caden like his own personal symphony that Charles was drinking in. He gave himself a pause to admire the even coating of marks criss-crossing over the presented rear end before he spoke. “Now we are going to take it up a notch.” He warned letting Caden observe for now as he moved to his bag of tricks and extracted a plug not much different than the ones that Caden had been stretched with today but slightly bigger as it seemed Charles was training him to take quite the large objects at this desire.<br/><br/>The dom poured some cool lube between the heated cheeks as he worked his digits along Caden’s hole not waiting for permission to as he worked a digit inside to see if the boy was still loose. He showed patience and stretching him again but not giving too much pleasure and more focused on the act to be able to accommodate the toy which he lathered generously and started working inside of Caden at whatever pace he was comfortable with. “Breath...” He teased the rubber thing with quite a bit of weight to it now inside till it was fully seated and looked quite satisfied with the resulting display. “Now... we being again.” He stood to extend the crop once more striking it but this time hitting the large base of the toy sending a shock through it with the force.