This all started a few years ago when Princess Alex and Mistress May convinced him to try chastity in "Lured Into Chastity by Devious Dommes", with him thinking this is only going to be a fun little trial run. Days turned into weeks and then months. To where he's really desperate and seeks the key back from Alex in "Chastity Release Appeal". Naturally Alex just seduced him into staying locked then and tormented him even further.
So now it's been a few years and he's desperate as ever. Alex introduces Goddess Sydnie to Her sub and there's all kinds of implying They might let him out, but also threats of months and years longer. Alex and Sydnie bounce Their asses into his face, vibe his chastity cage with a Hitachi and taunt him with Their pussies right in front of his face as his mind gets weaker and weaker.
The same theme continues on. Alex and Sydnie leave him tied up, a helpless and orgasm denied puddle of a man whose orgasms will stay under Their control. You can tell by Alex's dismissive attitude towards Her sub just how little She cares about his pleasure!