Dylan O'Brien Short Stories

Dylan || • angst/smut

You don't know why you didn't listen to your gut when you fell into this. But you also couldn't help it either. Dylan was someone that you have been in love with for nearly five years. He was someone you'd grown close to after meeting a few times through mutual friends. You two clicked and you both formed a bond that seemed to grow stronger every time you were together. You watched proudly as he scored more and more roles. You provided a shoulder when he went through his break-up with Britt.

But what you never expected was a night of bar hopping and drinking to result in you waking up next to him - naked. It took about four seconds after waking up and the soreness between your legs to realize what happened the night before. You had a few minutes of panic thinking you'd just ruined the friendship you held so dearly. But instead, the opposite seemed to happen...at least at first.

"I don't regret it, y/n," Dylan spoke as he looked towards you, his hand gently grabbing yours as he felt the panic slowly settle in. "Just 'cause we were drinking doesn't mean I wasn't aware of what was going on."

You looked towards him confused, "What?"

Dylan shrugged his shoulders, "Why don't we keep doing this?"

"You mean like friends with benefits?" You asked, feeling your heartbeat spike up a little.

Dylan looked towards you before nodding his head, "We're both single. Last night was fun...why not keep each other company in the meantime?"

In your gut, you knew that you should've said 'No'. But instead, the opposite came from your lips.

At first, things were fine. It was like nothing changed between the two of you. You hung out, talked, and acted like normal but sometimes the two of you had sex and hooked up. And it was a benefit indeed. No one had made you feel the way that Dylan did. None of your ex's or other hookups came even close.

Hearing him in your ear moaning and telling you how good your pussy felt was your new favorite sound. Second to the deep, gravely, the animalistic sound of him cumming deep inside of you. You also learned that Dylan had a bit of a praise kink and his favorite form of foreplay was sitting between your thighs and making you cum till your legs were shaking.

And it was fun for the first couple of months, but then the feelings you'd been harboring became more complicated. It took a night out with the rest of your friends that forced you to face your feelings.

You all were at one of the bars that you all frequented the most. You slipped on your favorite pair of jeans that hugged along your ass perfectly along with a lower cut top. When you walked up to the table that everyone was sitting at, you were welcomed in with excited hellos and a few hugs.

Everything was going perfectly. Everyone was drinking, dancing, and talking together. Even a few other regulars of the bar that you knew joined. You were at the back part of the bar with Sarah and Tonya playing pool with a few others. You'd just gotten done taking a shot when your eyes were drawn to the other side of the bar.

A heat fell over your body as you saw Dylan standing at the bar beside another girl. They were both leaning into each other talking. Your heart hammered in your chest as you watched him lightly touch her arm and smile towards her. You knew when Dylan was flirty with someone else. His body language made it obvious. And adding drinks into it only made him more of a flirt. It was a known fact among all your friends that Dylan was a flirty, borderline horny, drunk.

Pretty sure that's how we ended up in bed together, you thought to yourself.

You tried to ignore it for the rest of the night but it seemed that as the night grew so did your irritation.