Work Text:
You’re upset with him over the whole incident in Skyhaven? Fiiine. You can stew and ignore him all you want. But that doesn’t mean he can’t keep an eye on you to make sure you’re safe! At least that’s what he’s telling himself.
‘I’m just.. keeping you safe. Who knows if some creep’ll break in while you’re defenseless like this? I need to watch. For your safety.’ Caleb thinks to himself as he palms his cock through his uniform slacks. He’s in his office, eyes glued to his monitor. On screen, there’s a video feed of your bedroom. He watches as you grab and pinch at your tits through your thin pajama shirt. It’s extremely unprofessional, what he’s doing in his office right now. But that doesn’t matter right now. What’s important is that he has eyes on you. Eyes that keep wandering up and down your body as you touch yourself, as you touch what’s his.
He sucks in a breath as you push the shirt up, revealing your perfect breasts as you pinch at your nipples, huffing quietly at the sensation. He’s thinking about the pretty noises you’d make if he were there to wrap one of your nipples between his lips and suck as he used one of his hands to grab and tease the other.
‘God, you’re so beautiful’, he thinks. He really should stop watching now, but how could he when you were putting on such a cute little show for him? It’s all for him, right? It’d be rude of him to not appreciate it.
His cock is out now, his hand wrapped around the shaft, pumping it gently as he watches you slip off your panties and rub your fingers up and down your slit. He groans and jerks himself faster as you slide a finger inside of your folds. Your moans are getting louder now, and all he can think about is how he should be there to take care of you. It should be his hands all over you, grabbing a handful of your ass as his thick fingers pump in and out of your pussy. He just knows he’d make you feel so good.
You need him there, he knows your fingers aren’t enough to get you off how you want. You need him there to help you. Only he’d be able to give you what you need, he knows it. Why did you have to be so stubborn? Caleb knows he’s all you need, why can’t you see that? If you’d just stayed in Skyhaven, he could give you everything you wanted-
His train of thought is interrupted when he hears you let out a particularly loud cry. His eyes flick back up to the screen as he watches you finger yourself a bit more intensely, hips bucking up a bit each time your fingers slide back in. Oh, you’re close. He is too, his cock head leaking precum. Honestly, he could cum this second just looking at you. But he wants to be good, he wants to cum with you. You’re putting on such a pretty show for him, it’d be rude if he didn’t last for the full thing. But his thoughts distract him again.
Where would he cum, if he were there? On your pretty face? Or should he paint your soft tits? Or… No, he knows exactly where it should go. He’d grab your wrist and pull your hand away from your cunt, push your legs up and back as far as they’d go and slide his thick cock into you. You’d be ready for him at that point. You’d feel perfect around him, whining so prettily at how he stretches you out as he pumps into you, fast and rough, chasing his end.
He wouldn’t last long inside of you, either. A few deep, nasty strokes later and he’s spilling inside of you, groaning at how you clamp down and milk him. That is where his cum belongs, he thinks as he fists his cock faster. His eyes are closed now, distracted by the thoughts of how he needs to mark you, he needs to let that pretty pussy know who it belongs to, let you know who you belong to-
“Fuck!” He hisses as his own orgasm surprises him, ropes of cum shooting onto his desk. Huffing as he tries to catch his breath, his eyes finally blink open and he looks at the screen. He frowns when he sees that you’re already up and heading to the bathroom to clean up. He missed seeing your cute face as you came. :(
He supposes he just has to keep this video feed going, to catch you like this again, so he can appreciate the full show.