Stay Like This (Caleb x reader)
"Would it help the pain?"
summary: friends with benefits care about each other more than they realise
tags: friends with benefits, mutual pining, emotional hurt/comfort, implied sexual content, emotional vulnerability, crying, first kiss, mention of general grief/sadness
wc: 1.6k
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You knew it was wrong when you stepped out into the cold night at the beep of Caleb’s car. It was wrong to go and meet him tonight, and you weren’t going to at first. But then he said he didn’t have a good day either. Do two wrongs make one right?
You try to walk slowly so your skirt doesn’t completely ride up your thighs, even though in an hour it would be discarded anyway, lost in the darkness or below Caleb’s leather seats.
He smiles at you with a tip of his head when you get in and you smile back, genuinely so glad to see him. Caleb didn’t know about your pain, and you didn’t know about his. Only that when you were together like this, it didn’t matter. And you didn’t ask. You happily slip into the performance.
“Bad day too?” He starts, reversing out the driveway.
“Yeah, just the usual. You?”
“Something like that. But I’m here to make it better”.
You glance between his lips and his eyes, that were already turned to the road. He slips a hand onto your thigh like he usually does and turns onto the highway. Where was he going tonight? You wanted to ask but the words died in your throat as you start to drown in your thoughts. Your grief.
“You okay?” Caleb asks, worried. “You’re quiet.”
Don’t ask me that, you wanted to say. Don’t ask me that or I’ll spill everything and… I can’t do that to anyone. A further part of your mind thinks, that if you had to tell anyone, it would be Caleb. You knew he didn’t judge, that’s why you did this in the first place - you trusted one another.
You put your hand over his own and nod, “I’m fine.”
Caleb watches your response and doesn’t reply. You knew he didn’t buy it, but you’re pleased he didn’t press for details. Instead, he winds down the windows and turns the music louder. The air blows in on your faces and you look to him beside you. There is something so carefree about how his dark hair flickers in the wind, a sparkle in his eyes.
There was nowhere better Caleb wanted to be right now.
A little after ten, the car turned into a dark car park off the highway, hidden. Caleb cuts the light in the car but doesn’t move.
“You wanna get in the back?” He asks quietly.
You feel your eyes widen. Why was he asking like he cared? Why was he looking at me like that?
“Yeah, let’s go.”
When you get in the back, Caleb just hold his hands out.
“What are you doing?” You instinctively draw back.
“You’re not okay,” he states, voice breaking.
“No Caleb I’m not okay,” your voice raises, and you try to continue but nothing else can come out.
He just sits back, defeated, and you watch him carefully. He lets you touch his chest, drifting lower. He helps you undo his belt, fingers brushing over yours. His eyes never leave yours. Why was he not… he was more reserved tonight. He’s waiting for you to make the moves. You figure he just wants you to take the lead.
You undo his belt and encourage him to take off his pants. Caleb tries to cup your face, but you just look up at him. As soon as you see his relaxed expression and a nod, you move closer.
He runs a finger along your bottom lip and lets out a relaxed sigh as he brings your mouth up to him slowly.
You relax as he places a careful hand on the back of your head, gently running a hand through it, massaging your scalp. It only makes you like Caleb more.
He says your name, not in pleasure. And you stop immediately and look up at him.
“Can you come sit on my lap?”
He helps you up and you straddle him, pants half way down his legs. You can feel him against your tights under your skirt and you feel him get more excited. Caleb wraps his arms around you and pulls you against him. You rock forward, and his breath hitches into your ear. Cute. You hold onto his shoulders.
Suddenly, this all felt too much. The feeling of Caleb hugging you. This whole night had been really slow, it didn’t have that same thirst as the times before.
He tugs your hips flush against his so you stop squirming. You can hear his breathing as he brings his hands up to your face and kisses your hair. It was only until he kept going, kissing your temple, that you realised something was different.
“Caleb…” you swallow. “What are you doing?”
“I can’t do anything if you’re in pain… I won’t,” he replies firmly.
You don’t know how to respond, but Caleb just draws back and looks into your eyes. You look away. We shouldn’t even be doing this, why was he watching me like that.
He calls your name again, and it’s softer. He gives you time, waits for you to turn before looking at you.
Caleb unflinchingly looks into your eyes, flecked with pain. You don’t have anything to say.
“Well aren't you gonna kiss me?” He asks quietly.
A smile forms in the corner of your mouth. “Would you like that?”
“Would it help the pain?” He says desperately.
You take a breath. “Yes.”
“It would help with mine too.” Caleb rests his forehead against yours.
“Are you sure?”
There was so many things you did with Caleb. So many crazy things, but a kiss had to be the thing that somehow felt like taking a big step. More like a leap off a cliff.
“I’m sure,” he whispers, bringing a hand up to the side of your face. “I’m so sure.”
He watches you and leans back slightly. He watches you as your lips follow his and press a light kiss. You don’t need to draw back fully to see his reaction as he wraps you in his arms and kisses you back. Caleb’s kiss is strong and steady, just like his arms, and you can’t help but melt into him in a rush of emotion.
You don’t know when it started, but you’re suddenly crying, and trying to focus on kissing him back. Caleb draws back, sinking lower into the backseat and takes you with him. His eyes look so soft, and when he kisses you again, it’s slow and reassuring.
When he draws back again you try to stop your tears by biting your lip. Caleb is still looking up at you from beneath, like you’re a god, completely unfazed by your tear streaked face.
He pulls you into his chest and you collapse completely into him.
“You can let it all out with me. I won’t judge, I promise.” He brings his hand up to your head, and strokes it, holding you against him.
You bite your lip and shut your eyes. Caleb shouldn’t be able to support me like this. Even though he was the only one to quiet the pain.
“I promise, I promise,” is all Caleb whispers over and over again.
“I’m sorry… you shouldn’t see me like this.” You say, trying to come to your senses.
“I know you only want to show me your good sides. But I don’t want you to act with me.” Caleb says. “Let’s just… stay like this and then I’ll drive you back home.”
You only relax into his arms and nod, bringing a hand up to his chest. You hold onto the fabric as he lets you cry everything out.
All Caleb can think about is how much pain you must be in, and he finds himself wanting to protect you. He wanted nothing more than to ask why you were in this much sadness.
Hours later, you find the strength the get up off Caleb and all your cells scream for him. You didn’t want to leave.
He drove you home, his hand resting on the back of your headrest. He wanted to comfort you still.
He fixes your clothes once again, even though he fixed your shirt multiple times, smoothed your skirt out, since you got up from being entangled. You watch his eyes on you, as he seems to find more and more things to adjust. He was drawing this out. Why?
“If you need a shoulder to cry on…”
Your eyes rise to his, "I’m really sorry Caleb-"
"No. I’ll be here for you."
He wasn’t mad. He didn’t think you were silly.
"I already make you feel good," he winks, trying to lighten the air. "The least I can do is help you feel better."
You nod, before leaving him and heading inside.
You keep thinking that he doesn’t owe that to you. That’s not what you call each other for when you’re insanely touch starved and horny at god knows what hour.
You weren’t wrong to want to see Caleb tonight. That’s all you can think as you slip into bed, not bothering to shower. You could still smell Caleb on your skin and you relax into the sheets. You don’t cry for the rest of the night, you let it all out with Caleb.
You just relax into his smell and you’re asleep in minutes.
Caleb on the other hand, laid looking at his phone on his nightstand before rolling over. He held a pillow to his chest, pretending it was you.
There was so much he wanted to say to you, he just hoped that tonight had been comforting for you. As much as he usually gets you out of your thoughts, he hoped he hadn’t made it worse.
He’d ring you in the morning. He had to know if you were okay. But… he’d give it the night. Just to make sure that when he wakes up, what you did willingly wasn’t a dream. That kiss wasn’t a dream.
But above all, to make sure you were okay.
© xavibloom 2026
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