The short headcannon you wrote about Ray using his darlings underwear to... You know 👀 stopped my heart,,, I'd love to read more about how he gets off before kidnapping or what he does/how he acts when his darling is asleep before taking them (I've fallen hard for this boy),,,
Look - Ray might be the sweetest of the bunch, but don't think for a second that means he isn't a disgusting perv.
TW: NSFW, somnophilia, generally Ray being nasty, noncon.
Ray is utterly enamoured with your sleeping form - so cute, so unaware, so... vulnurable. He may have broken in to your home to pick up a few items of your clothing, but seeing you sound asleep is certainly a tempting sight.
God, he feels disgusting. As he hastily removes his belt, he hisses under his breath. He shouldn't be doing this, this is wrong. Ray, however, is not a man of great willpower - he feels his cock throb in anticipation as he carefully approaches you. Seeing you up close, having his painfully erect cock right next to your face, feeling the gentle breeze of your breath - suffice to say, Ray won't last very long.
Sure, he feels guilty exploiting your helpless self, but never embarressed. Being free from your conscious judgement is oddly liberating, encouraging him to be more salacious, more depraved, than ever.
It starts off tame enough, simply pumping his cock right next to your face as your mouth draws deliciously close to his length. He's quick to fall into further depravity, parting your lips with the tip of his dick and quietly groaning your name. He always makes an effort to clean you up afterward, but always leaves a small sample of his cum on your cheek. The mere memory of your sleeping face covered in his hot seed is sufficient jack-off material for weeks.
Of course, taking advantage of your sleeping form isn't the only way he relieves himself pre-kidnapping. Stealing one of your pillows, cutting an adequate hole into it and pounding it until it's dripping with his cum, thrusting ruthlessly with his nose pressed against the fabric. It smells just like you. If he closes his eyes and whispers your name, he can imagine it's you he's fucking.
Then there's his personal hentai collection - pages upon pages of carefully drawn panels, all depicting the various fantasies he dreams about. He particularly adores drawing what he imagines your ahegao face looks like, but he's sure it looks even hotter in person - saliva and cum mixing together as your tongue lulls from your mouth, eyes nearly rolling into the back of your head. Ray never feels like he does you justice, but that doesn't stop him from jacking-off to every single fucked-up drawing he makes of you. Tentacles, pseudo incest, noncon - all his dirty little secrets and desires on display.
Just hope he never decides to enact on any of his fetishes.