All good, ticklish ideas! And yes, he was clearly enjoying himself...there was no hiding that with his rock hard cock pointing straight up. To answer your question about how long/safety, first...as you probably know very well since I know you're a big fan of this site, everything I do has "safely first!" in mind. I think some may even occasionally get slightly annoyed at how every Tutorial Tuesday post starts out with a Safety section before getting to "the good stuff"...not to mention the animated yellow bar that I have bounce up from the bottom of the page just as another reminder to make sure you read the Safety section first. ;-) That being said, the same applies with more intense predicament bondage like this one. Not only do I not leave the room and watch the situation and the sub's reactions very closely, but I even go as far as to feel his hands and feet occasionally (often after a smartass comment about how I'm not getting romantic with him, haha), just to make sure any added stress there isn't cutting off circulation, leaving hands/feet cold (or tied balls, in some cases). As for this predicament, after just now reviewing the time stamps on the photos and video I took of this one...he was in it for around 26 minutes. Probably a bit more, since that's the time from the first pic, to the last (and only) video being saved. I've had other subs in something like this...for literally 30 seconds. Not every sub is built for stress positions like this, and sometimes that's difficult to judge just by looking at a sub. I've had a muscle bound gym rat that couldn't handle this one for even 1 minute, so he was released pretty quickly as I could see him wavering a bit trying to get his bearings. In any case, it's case by case...and there are normally signs that it's becoming too much for a particular sub...but I wouldn't leave him in it TOO long regardless, for the same reasons that you pointed out. Does that help to answer your question?