This is what happened when a chastity-locked boy questioned me without thinking first.

He had asked me to help him build up more muscle.  I had his dick locked in a Jail House chastity cage as you can see here, as a tool to help me get him where he wanted to be.  That meant that any lazy and unmotivated days would translate to additional days before I allowed him access to his dick again. Sometimes I even made him do things to increase his horniness level a few notches.  He does have to learn that being lazy won’t get him anywhere.

Speaking of laziness, that’s what got him into this situation…

He was to do his push-ups for the night on cam over Skype, while I watched him.  He told me he had done a workout before we talked that night.  I asked him what he had done unsupervised, he told me, and I wasn’t all that impressed.  So I decided to make him do a few more push-ups while I watched.  Instead of the “Yes Sir” attitude I had expected from the boy, he questioned if I got his message about his workout that night.  It sounded like whining to me, and when a chastity-locked boy whines, he gets punished.

I told him to get on Skype immediately, where I made him do 25 push-ups.  I could tell he was really struggling by the time he got to 10.  I guess he shouldn’t have questioned me.  If he hadn’t, he might be done after doing just 10 push-ups. But now I wanted 25.  He struggled to get 2 more push-ups in, then he collapsed.  He just couldn’t crank out any more.

But accepting that without any other punishment would only tell the boy that he could get away with it in the future, and thus not meet his goal.  So I told him that he was going to be writing some lines before he went to bed that night.

Me:  “You’re going to write the line, ‘I will not question my Master’…

13 times, once for each push-up that you didn’t complete…

in black marker…

written on your own chest.

It must be legible and written so I can read it from left to right in the photo that you’ll be sending me tonight.  If any of these rules are not followed, you’ll be wiping it off and starting over.  You have until midnight to get the photo to me, or I’ll start adding days to your chastity sentence.  One day will be added for every hour past midnight that I don’t have that photo in my Inbox, up to a total of 13 additional days…one day for each push-up that you failed to complete.

Understood, boy?”

Boy:  “Yes Sir.”

He began very carefully writing on his chest, “I will not question my Master”, a total of 13 times as ordered.  He ran out of room on his chest after writing the line 11 times.  So he had to get creative, no matter how much more difficult it was, and hope that I’d accept it.  So he turned to his ass to write the last two lines.  This proved to be very difficult.  He actually had to wash off the left side and start over several times, but his locked cock made him push through and get it done to satisfy my requirements.