It must break your poor little sissy heart knowing you're never going to fuck a real girl... not since I locked your little pee-pee is away in chastity. Fucking girls is totally out of the question - as is jerking off in the kinda way most boys would think of doing. Locked-up wimps like you can sissygasm I suppose but even filling your ass with cock can sometimes prove quite the challenge to nudge you over the edge... Your options are limited, sissy, so you could just remain frustrated, limp and denied like a good sissy - kept off-limits to any sexual pleasure - that's really what sissies like you deserve and if I had my way that's exactly how you'd stay forever - unsatisfied, cumless and pleasure-blocked. Unfortunately even sissies need to leak your failure-slime once in a while so I'm gonna allow you an alternative - extra-humiliating way of org-spasming today... by humping a pillow like a girl.
Imagine - pillow-humping is humiliating enough - but grinding a chastity-gasm out on your pillow just like a girl is even more embarrassing... Especially since I'm gonna make you wear your girliest panties over that little caged cock as you try your hardest to rub out an emasculating cage-gasm. I'm going to make you wear a full set of satin lingerie - some satin panties. A matching bra and silky stockings would be perfect! You're going to look so pathetic with your pretty satin panties over your little cock-cage as you hump your pillow for me. Slipping around with that pillow between your legs as you desperately try to find a way to cream your cage. Do you think real men cum like this sissy? Do you think this is how a real man would like to make cummies for me? Haha - no this way is just for little caged sissy failure like you - an extra special method to shame the fuck out of you until you leak for me.
I want you to humping your the pillow as femininely as you can - don't try fucking it like a man would - you're going to arch your back and ride your pillow pushing it between your stocking-clad thighs and grinding your pretty pantied crotch into it. You're going to look so pathetic - so desperate and you rub yourself into that pillow sissy. I want you to make pretty girly noises too - moan like a girl as you feel your satin encased chastity device glide over the pillow. Whimper and squeal as you get closer to making cummies in your cage for me - push your ass out sissy - be extra-cute for your pillow boyfriend - this is the only way you're allowed to cum - just like a girl - Keep going sissy - this is how girls like you cum when there are no boys to help you! This is the only sex-life you deserve now - locked in chastity and made to fuck a pillow in your pretty satin panties.