As someone who has very little experience with anal, it can be a bit tough for me to handle at times. When the mood strikes me though, it does end up getting me going pretty damned well. I honestly can't say if it's as frustrating as being edged to high hell or if it's worse, but it'll definitely get you pleading for release. To make it an even more frustrating time for the boy, daily plug requirements can work wonders. It also works great as a prerequisite to release from chastity; getting more submissive and desperate with each subsequent fuck until he's been fucked enough to be let out.