My sub has been locked in chastity for over 2 weeks, and I decide it's time to free him of his cage so I can wind him up before sending him away locked up again. I've already pegged him, so I want to use his other hole too by sounding him. His legs are bound while I stretch him out, with a wand placed on his balls for extra stimulation. I stroke and sound him, before giving him a chance to cum before losing his freedom again. I count him down... do you think he'll get to orgasm?