#oc.caleb

cw: choking mention (this is an older writing post. pls don't send me asks involving choking, thank u!), death mention, noncon mention

"You... You said I was gross, right? I know I am- I, I-" Caleb's breathing so fast he needs to take a moment to calm down. A laugh, closer to a giggle, leaves his mouth. "I'm glad you agree! But you said that- That you wanted me to stop following you around...? T-that I can't just keep trying to smell you...? I- I won't stop if you don't do anything. Definitely not."

His hand is wrapped around yours in a crushing grip, pressing your fingers down against the bottom of his throat. The flesh pulsates in time with his racing heart. He's shaking, not even crossing his legs to hide his arousal or keep himself from smiling as he stares straight into your eyes. You take a step back. In return, he takes three steps closer. Pressing your nails into his skin, you shudder as you feel him swallowing.

"Punish me. You want to make sure I never go near you again, so-! P-please... You're angry. You have to be, I'm disgusting and I've been stalking you and stealing your things, s-so... Take it out all on me! I'll-" Momentarily, he bursts into breathy laugher again. "I'll be your punching bag... Choke me, beat me into a pulp, insult me, 'r-rape' me..." His voice climbs higher and higher as he lists them. He's drooling, moving your hand up and down so you're clawing his neck raw.

:’)!! pls feel free to send another ask about his most extreme fantasies cuz this got looong already!! i kinda wrote a similar post to this before but i feel like the way im writing him keeps changing little bits LMAO

notes: implied dubcon, implied abuse, incredibly unhealthy coping mechanisms, suicidal ideation (kind of,, more like just a general death wish)

Abuse is what Caleb wants, but it’s not what he needs.

You're right, he'd be at a complete loss.

Caleb's scared of getting too attached. He fucks around with people and has them do weird shit to him, sure, but it's never anything more than that. If that's the only time he sees them, then that's something he can live with. It's okay. He knows what kind of game he's playing. As long as he no one tries and actually gets to know him, he won't get his feelings trampled on. Won't expect too much out of what is ultimately shallow.

But you're... You're being nice. You invite him over and he's expecting to get his ass wrecked but you're all dressed up and roses in hand. (He's wearing like sweatpants and a gross hoodie. Save him.) Offering to take him out for a nice night. It's okay if he doesn't have the money, you didn't tell him beforehand, so you'll pay. He's usually such a chatterbox, but you've left him completely tonguetied. Kicking his feet underneath the table and nervous about every question he answers. Every honest answer is going to show how far away from dating material he is. (and he shouldn't care. he shouldn't even be considering it. but the truth is, he really is just so fucking lonely.)

He knows he's falling way too hard for you when he stumbles out of your bed, rope marks still on his skin, shuffling off to get his clothes. But you reach out and pull him back by the wrist. Where does he think he's going? You're not done yet. And he's just like. Oh, wow. He's not sure he could cum again, but he's not going to miss out on a chance to get touched more. Then you pull out the cream and ask him where it hurts. He's taken so off guard he just sputters, so unable to speak he points to the spots instead. When you press a kiss to his cheek and have him be the little spoon, you won't see he's tearing up.

How he would react? Creams his pants if you hurt him, gets very horny if you simply yell at him. This is exactly the response he wanted. You're usually so adorable, quiet like a mouse, but you've got a completely different side to you! One that he's managed to bring to the surface!! He's just so overwhelmed by this development that he can't latch onto you like he wants to. Caleb doesn't want to interrupt you out of fear of snapping you out of your anger. Insult him more, push him around more...! Make his ears ring with how you're screaming in his face!! But it's easy to misinterpret how much he's shaking, how he's burying his face in his hands not to hide tears but how red his face his. If any place is leaking, it's his dick.

It’d be great for him, at first, when he’s still chasing after strangers fucking him up. There’s no shortage of lewd perverts and rapists in town after all!

But he has a soft heart under all of that. He’s not in it to cause you pain, unlike some other LIs. Living in town would break his heart in the long run if he got to know you, date you and love you, only to see everything else that happens to you.

I guess in a way, he can rationalize bad things happening to him since he thinks so lowly of himself, but if he softens up and does his best AND you still get the short end of the stick?? That’ll probably shroud him in helplessness. You’ll end up having to reassure him you love him nearly every day, he gets lost in his own bad thoughts so easily :(

(Yes, greasy, creepy sex offender boy can get his heart easily hurt is a favorite headcanon.)

cw: implied noncon

It's all good until he finds someone he cares about! (And someone who cares about him in return.) Caleb doesn't care if he ends up getting the shit beat out of him and left alone in some alleyway, he was asking for it. He always is. The cum drying on the inside of his underwear is enough of a testament for how fucked up he is. He's a literal cockroach, no matter how many times he's stepped on, he always comes back. That's one of the ways he sees himself, at least.

But he can't do that when someone is out there worrying for him. It'll still happen from the reputation he's built, however, he doesn't go looking for it anymore. (It's his own fault for being like this.) Knowing the town's nature leaves him restless. He sees you as a better person than himself, as most of the people there, and it kills him inside to know the things you're going through. Have gone through, before meeting him. Caleb's a freak yes, but you're right, he never sets out to scare anyone. Doesn't move with the intention of hurting anyone but himself.

Sounds like he deserves a reward. How about waking up to a nice CNC roleplay as a treat? He can be the pretty thing you saw on the street and just had to have for yourself. Break character just long enough to kiss his forehead and remind him of the safewords you two have. But you’ll push your own limits to see how far you can push him to the limit he’s always begged for. He doesn’t even have to worry about being broken, because you always take the time to lovingly put him back together afterwards.

But then you’re shoving his face in the bed and breaking him in with your thick, ribbed strap til he screams. It’ll get him nice and warmed up for the next activity you have planned. You’ve always wondered how much he can actually take in him. What he can take in him. You got creative with the objects you plan on squeezing in him and you look forward to taking pictures of his flushed, teary face while he’s all stuffed up and bound. You’ll give him the album as a present afterwards.

He doesn’t know this, but you’ve bribed a few cops to look the other way when you give Caleb one of his gifts: getting his insides rearranged in a dirty, grimy alley. Paid a few people to walk by and gather around while you break your little cocksleeve. By this point he’s so sensitive and overstimulated after a whole day of being brought to the brink and back, but you’re still slamming in him as if you’d just started.

It’s all for your sweet, darling boyfriend who took you to a restaurant in his suit and did his best to make you happy. When you’re done with him, you take his red and blotchy face and pepper kisses all over, telling him how much you love him. Happy anniversary.

ANON???!!!??/ THIS IS . SO GOOD. THIS IS ACTUALLY TOP TIER THANK U??? FOR BLESSING MY BLOG WITH THIS?? GENUINELY U WROTE THIS SO WELL I CAN'T ADD MUCH

Other people watching him has him warm all over. But he can barely focus on them. All he can think about is you, you, you- How you're splitting him open, how you're rubbing his back raw by dragging him across the floor. He's wailing so loud the entire neighbourhood must know what's up, his cock shedding tears just like his eyes are. When his orgasm slams into him, it's a sharp pain rather than pleasure. But he loves that too. It's all too much, way too fucking much... His brain overloaded with a fucked up cocktail of chemicals. He still manages to get a fucked out, hazy smile on his face. Just for you. What a whore.

He's so in love with you for having fucked him up so badly. Says that he loves you too in a whisper, which is all that's left of his voice after having screamed so loud. So clingy during aftercare that you have trouble getting him to let go of you long enough to help him wash up. Caleb's crying a lot, unsure as to why. It's just... All overwhelming. He feels tangled up inside. He's yearning for praise and comfort more than anything else, still shaking all over as he comes down from his adrenaline high. In the end, he only manages to fall asleep to the sound of your voice and your fingers playing with his hair.

notes: CONSENSUAL SN-FF FILM (CONSENSUAL MURDER) ROLEPLAY(? with caleb as the victim, obv <3) humiliation, implied unhealthy relationship