ROFLMAO -- Noboby just "wakes up" with a CB-?000 chastity device on unless he was drugged. But jacking off with it on was clever of his Mistress to suggest. Now that she knows he CAN, this naughty boy's Mistress needs to correct the fit on his chastity device to prevent a repeat.
Normally I live seeing men cum, but I would have loved it if you hadn't been able to pump that cock out. How long, I wonder , have you gone wihtout orgasm?