In years past, I’ve written that I have tried chastity, but it’s extremely difficult for me comfortably because my balls are extremely high and tight. Either a device is loose and just slips off, or it so tight it causes pinching. So I haven’t had much success with it.
That said, every once in a while, I still get the urge to try it again. First up is a device is kind reader sent me years ago. It usually has a steel belt around the waist, but I changed that out for a more comfortable elastic one (let’s face it… I’m doing this self-imposed, so I’m not exactly going to cheat and cut it off).
It looks great, and it’s actually pretty comfortable. But the down sides for me is that the tube is pretty large, and not super comfortable underneath clothing. And, uh, I did manage to slip out of it after a few hours. :/
Next up, I tried out a new and pretty cruel device from The Stockroom… the Penis Prison with pin prick lining. It goes around the entire cock and ball area, and its pretty comfortable… well, until your cock or ball rubs against the pin prick lining, which is the entire point.
Close up of the pin prick lining. 
While super hot to hear (especially, ahem, when further tortured with a Hitachi Magic Wand over it), there absolutely no hiding this under clothing. Also, no piss slit options, so this is a short term wear sort of thing. That said, I think it’d be the perfect thing for some slaves to wear in future meets.
So while there are some successes here and there, I’m still in search of something I can wear more long term comfortably and under clothing, without slipping out.
