Making a boy jerk off while you watch is always fun, and the possibilities are endless. It can be done in person, via webcam, delayed video, etc. And there are so many ways to mix it up. Here are some of my favs:
- Increase the audience. For a shy guy having to masturbate while others watch can be a big mindfuck. Standing in the hallway immediately after walking in and being ordered to strip and jerk off. Inviting a friend or two he's never met over to enjoy the show. Taking video and publishing it to XTube or Tumblr.
- Make it more difficult. If having to jerk off while others watch wasn't embarrassing enough, having trouble doing it is so much worse. A punishment for failing to finish in a set time can add to it too. Holding in an enema? Full bladder? Waiting for an ice cube (cum cube?) to melt in his mouth? From a difficult position, to having to use his non-dominant hand, to
distracting things going on / being done to him, there are so many ways
to make it harder.
- Don't let him finish. Make him edge himself repeatedly until he's horny out of his mind. Only let him cum in the x number of seconds at the top of every minute (but don't let him see the clock, just tell him when the window starts and ends each time). Make him tell you when he's close and ask permission before he blows (and obviously don't give that permission until he's earned it).
- Repeat. As the saying goes, a good punishment is just starting when you're wishing it was over. Maybe the first load wasn't so bad and he got off easy, see how he does the second or third time around. For a lot of guys the eagerness to play the game goes away almost instantly after they've cum, so forcing them to do things afterwards is often a big deal.
Have fun! Be sure to share your comments of things you've tried or things you want done to you.