Update: Links to video of this session included below.
In short, yep, this boy was truly fucked...but not in the ass, more like a good throat fucking.
First, I got him pretty well restrained to the bondage stool, which I had previously added the dildo jack to...with a big dildo protruding right through the hole in the seat. I got his hands cuffed to the D-rings at the base of the stool, then used some ratcheting ropes to secure the D-rings on either side of his collar down to the stool, and ratcheted them down just enough to make sure he wouldn't be able to pull his mouth off of the dildo that I had forced it onto. But did he have any idea what was about to happen to him? For all he knew, this was just a stationary dildo designed to force him into a fairly humiliating position for a while.
He quickly realized that if he got lazy and rested his head down lower, it would result in him gagging on the dildo that was sticking up a few inches higher than that would allow. So he was forced to hold his head up...constantly!
Then suddenly as I held up the fucking machine remote in my hand, with a very evil grin on my face, he heard a "CLICK"...as the dildo started forcing itself deeper into his mouth and threatening to violate his throat. So he pulled his head up even higher in a desperate attempt to avoid this inevitable outcome, only to realize I had severely restricted his head's movement in that direction. UP, DOWN, UP, DOWN, UP, DOWN...the fucking machine never gets "tired". ;-) Now all he could do is try to focus on allowing the dildo to invade his mouth, welcomed or not, and try to sustain his energy to keep his head up. If not, GAG-GAG-GAGGING was inevitable.
Sorry guys, some of you have been asking me for the video of this session...so I'm updating this post to include them.
But how long was I going to keep this deepthroat training punishment going for? Until I felt he had learned how to deepthroat my cock properly? Maybe a bit longer to ensure it sinks in, and that he never slacks off again in the future?