Dylan O'Brien Imagines

By BriNanny17

1.3M 20.6K 9.1K

Just like the title says. Imagines involving Dylan O'Brien and all his characters. Imagines containing smut a... More

Talking About The New Girl- Dylan O'Brien
Stuck-Caleb Halloway
Patching You Up-Mitch Rapp
Safe Haven-Thomas
Happiness is Everything- Dave Hodgman
Panic Attack-Stiles Stilinski
Forbidden- Mitch Rapp
Missing You-Dylan O'Brien
Please, Don't Hurt Her- Stiles Stilinski
Bad News-Dylan O'Brien
Help Our Mommy-Thomas
Help Our Mommy Part 2-Thomas
Help Our Mommy Part 3-Thomas
Protective Side of You-Stuart
First Kiss-Dylan O'Brien
Kidnapped Part 1-Mitch Rapp
Kidnapped Part 2- Mitch Rapp
Kidnapped Part 3- Mitch Rapp
Kidnapped Part 4-Mitch Rapp
Missing-Caleb Holloway
Stopping You-Stiles Stilinski
The Look-Dylan O'Brien
No Beanie Today?-Stuart
Calm Down Part 1- Thomas
Calm Down Part 2-Thomas
Calm Down Part 3-Thomas
Calm Down Part 4-Thomas
Calm Down Part 5-Thomas
Calm Down Part 6-Thomas
Take A Bullet For You-Mitch Rapp
Prove It-Dylan O'Brien
Faces From The Past- Stuart Twombly
The Crossover- Dylan O'Brien
The Crossover Part 2-Dylan O'Brien
Gotta Stick Together-Caleb Holloway
Eyes on You-Mitch Rapp
Eyes on You Part 2-Mitch Rapp
The Note-Dave Hodgman
In Sickness And In Health-Dylan O'Brien
The New Girl-Stiles Stilinski
Oops-Dylan O'Brien
Oops Part 2-Dylan O'Brien
Oops Part 3-Dylan O'Brien
Confiding in You-VOIDStiles
*First Kiss Part 2-Dylan O'Brien
Secrets Part 1-Thomas
Secrets Part 2- Thomas
Nightmare-Mitch Rapp
Nervous Induced Asthma-Stiles Stilinski
*"Work"-Stuart Twombly
Her-Mitch Rapp
Her Part 2-Mitch Rapp
Her Part 3-Mitch Rapp
Her Part 4-Mitch Rapp
Her Part 5-Mitch Rapp
Screwed Up-Stuart Twombly
*Neighborly Favor-Dave Hodgman
Wrong Place, Wrong Time-Stiles Stilinski
Wrong Place, Wrong Time Part 2-Stiles Stilinski
Abduction Gone Wrong-Mitch Rapp
You Matter to Me-Dylan O'Brien
*First Kiss Part 3-Dylan O'Brien
What's Happening?-Stiles Stilinski
I'll Find You-Stiles Stilinski
I'll Find You Part 2-Stiles Stilinski
It Should've Been Me-Mitch Rapp
Jealousy Brings Out Feelings-Dylan O'Brien
Jealousy Brings Out Feelings Part 2-Dylan O'Brien
Jealousy Brings Out Feelings Part 3-Dylan O'Brien
Giving Up The Fight-Stiles Stilinski
Not So Good With Girls-Stuart Twombly
Hey Bartender-Dylan O'Brien
Hey Bartender Part 2-Dylan O'Brien
Midnight Surprise-Stiles Stilinski
Dinner With My Parents-Dylan O'Brien
*Letting Off Steam- Mitch Rapp
*Letting Off Steam Part 2- Mitch Rapp
*Letting Off Steam Part 3-Mitch Rapp
The Club- Stuart Twombly
Hospitals Suck-Stiles Stilinski
Wounds- Stiles Stilinski
Long-Lost Siblings Part 1-Thomas
Long-Lost Siblings Part 2-Thomas
Long-Lost Sibling Part 3-Thomas
Long-Lost Sibling Part 4-Thomas
Long-Lost Sibling Part 5-Thomas
Wardrobe Guru-Dylan O'Brien
Nightmare Part 2-Mitch Rapp
Nightmare Part 3-Mitch Rapp
*Study Session-Stuart Twombly
A Strong Connection-Stiles Stilinski
Leave A Message After The Beep-Dylan O'Brien
Leave A Message After The Beep Part 2-Dylan O'Brien
War of The Mind-VOIDStiles
I'll Do It-Dylan O'Brien
Too Much-Mitch Rapp
Too Much Part 2-Mitch Rapp
Too Much Part 3-Mitch Rapp
*Too Much Part 4-Mitch Rapp
Your Fault-Stiles Stilinski
Building Confidence-Stuart Twombly
Night Terrors-Thomas
The Girl From The Helicopter-Thomas
*Senior Night-Stiles Stilinski
Live Listening-Dylan O'Brien
Your Fault Part 2-Stiles Stilinski
Survival of The Fittest-Caleb Halloway
Dangerous Woman-Mitch Rapp
New Haven Police Department-Thomas
New Haven Police Department Part 2-Thomas
Dangerous Woman Part 2-Mitch Rapp
Not The Average Girl- Stuart Twombly
*Not The Average Girl Part 2-Stuart Twombly
Our Girl-Stiles Stilinski
Confidence is Sexy-Dave Hodgman
Faces From The Past Part 2-Stuart Twombly
*Rough Starts-Stiles Stilinski
More Than Friends-Dylan O'Brien
The Call-Mitch Rapp
Wedding Freakout Part 1-Dylan O'Brien
Wedding Freakout Part 2-Dylan O'Brien
Safe & Sound-Mitch Rapp
Safe & Sound Part 2-Mitch Rapp
After Evelyn-Sam Taylor
Bring Her Home-Stiles Stilinski
Sneaking Thrills Part 1-Dylan O'Brien
Sneaky Thrills Part 2-Dylan O'Brien
Seeing Right Through You-Stiles Stilinski
*Finally Time To Be Together-Thomas
Saving The Preacher's Daughter-Sam Taylor
The New Greenie-Thomas
Whatever It Takes To Save Him-Stiles Stilinski

*A Second Chance-Dylan O'Brien

16.1K 165 185
By BriNanny17

Warnings: SMUT, fingering, unprotected sex, language, car sex

You should be happy with a little bit of nerves on your wedding day. But I wasn't. I wasn't happy. I was debating whether or not I was making the biggest mistake of my life. All I could think was that this was all happening so fast.

Chase asked me to marry him less than three months ago. We had only been dating 10 months when he asked me. Even when he was on bended knee and said those four words, I had a uneasy feeling in my stomach. I cared for him and I told him I loved him, but in that moment I wasn't 100% certain that he was who I wanted to spend the rest of my life with. And I have one person to blame for that doubt.

Dylan O'Brien.

I stopped pacing my dressing room when his name entered my mind. I'd be lying if I said I haven't thought about him since we broke up. Of course I've thought about him. He was the love of my life. I smiled as I thought about us growing up.

Dylan and I were inseparable as children. We lived across the street from each other and our families hung out all the time. We spent practically every day together.

He was my first boyfriend. "Boyfriend" was kind of a loose term for what he was to me. First of all, we were in first grade when we became "boyfriend" and "girlfriend". We "dated" throughout elementary school and middle school, but stopped in eighth grade when I was asked to the eighth-grade dance by my crush, Henry Jacobs.

Even when Henry asked me to be his girlfriend officially, nothing changed between Dylan and I. We still acted like a couple. We actually acted more like a couple than Henry and I did. Henry and I only went out until halfway through freshman year. The day he broke up with me, Dylan came to my house with pizza, ice cream, and all of my favorite movies.

Sophomore year, Dylan and I were lab partners in chemistry. We were studying for an upcoming test one night when I fell asleep on his shoulder.

I wasn't quite asleep when I felt him lean down and press a kiss to the top of my head. I held my breath as he whispered, "I wish I could say this when you were awake, but. . . I love you."

I went the rest of the school year knowing the truth. We were at a friend's party to kick off the summer when I ended up saying something to him about it.

~•~

I was outside sitting by the pool when I felt someone sit by me. "Hey," Dylan smiled. "You okay?"

I debated about what to say to him. What he said to me the night hasn't left my mind since he whispered it. I took a deep breath before saying, "No, I'm not."

I looked over to see his face drop. "What's wrong? What happened? Did Henry try and talk to you? Did the cheerleaders say something to you again? I swear if they did. . ." He jumped up and started heading inside. I quickly ran after him, grabbing his hand.

"They didn't say anything to me, Dylan," I said as I subconsciously intertwined our fingers.

"Then what's going on? Why aren't you okay?"

I bit my lip as I tried to gather as much courage as I could. "What's going on is. . . You."

"Me?" He asked, his voice getting caught in his throat. "What. . . What did I do? I swear, whatever it was, I didn't mean it. I swear. I never, ever, meant to hurt you. And if I did. . . I usually know right away."

"Dylan," I cut him off. "Breathe."

"What did I do?" He asked softly.

"Nothing intentionally," I said with a small smile that made him let out a sigh of relief. "The truth is, I heard you."

"You heard me?" He asked, tilting his head slightly.

"Do you remember when we were studying for our Chemistry test? And I fell asleep on your shoulder?" He nodded, signaling for me to go on. "Well, I wasn't as asleep as you thought."

I bit my lip, waiting for him to catch on. It took him a few seconds before he put two and two together. "You weren't asleep," he said slowly. I shook my head as he studied me.

I gasped when he stepped forward, grabbed my face between his hands, and pressed his lips to mine. I instantly started kissing him back.

~•~

We started dating that night and continued dating. Until he got his role in Teen Wolf. I was really excited for him, but a little sad. I knew he was going to have to move away and it broke my heart. We even tried to do long-distance, but after about four months of missed calls, unanswered texts, and barely talking we decided it would be best to move on.

I don't think I ever fully moved on. I mean, how do you move on from the boy you pictured spending the rest of your life with?

A few years later, I moved out to LA to go to UCLA and get my law degree. I thought about reaching out to Dylan, but it took me almost a week to send that text. We met up for dinner and I instantly noticed how much we had both changed.

We went back to being friends, not nearly as close as we used to be. We went from talking and hanging out every day as kids to talking, at most, every few weeks as adults.

When I got engaged, I debated for weeks whether or not to send him an announcement. I didn't. My mother did (without me knowing).

I sat on the couch, tears building up as I thought about Dylan. I subconsciously started comparing him to Chase. At this point, I wasn't even sure if I loved Chase. I definitely didn't love him the way I loved Dylan.

I looked down at the ring on my finger and started spinning it. Ever since he slipped it onto my finger, it's weighed me down. I quickly stood up and walked over to the desk. I took out a piece of paper and started writing.

Dear Chase,

I didn't hesitate to write out my feelings. I apologized many times but told him of my concerns.

I ended the letter and carefully folded it up. I wrote his name on the top and placed it on the desk. I stood up and looked at the ring on my finger. I took a deep breath and bit my lip as I pulled my engagement ring off and placed it next to the letter on the desk. For the first time since I put that ring on, it felt like the right thing to do.

I was currently packing what little things I had when I was interrupted. My eyes narrowed when I heard a knock at my door. I fixed my dress before walking over to the door and opening it. The sight on the other side made my breath get caught in my throat.

"Dylan?" I said, his name barely leaving my lips.

"Hey, Y/N."

I held my breath as he slowly looked me up and down. "Wow," he said under his breath. "You look beautiful."

"Thanks," I said, my cheeks burning. I subconsciously smoothed out my dress, neither one of us saying a word.

"Y/N," he started but I cut him off.

"What are you doing here, Dylan?"

He opened and closed his mouth, hesitating to answer my question. I raised my eyebrows, waiting for him to say something.

"Dylan," I sighed. I shut my mouth as he took a step towards me.

"I came to stop you," he said, barely a whisper. My eyes widened when his words registered.

I gasped as he grabbed my waist and slowly pulled me into his chest. The second my chest touched his, he pressed his lips to mine. I didn't hesitate to kiss him back.

I moaned as I felt the familiarity of his lips on mine. He took a few steps forward, walking us into my dressing room. I wrapped my arms around his neck as he kicked the door closed.

His hands ran down my back before cupping my ass. I instantly jumped up, wrapping my legs around his waist as our lips continued to move in sync. I smirked into the kiss as he put me on the dresser.

I moaned as his hands slid down my legs, slipping my shoes off of my feet. Dylan slipped his tongue into my mouth as he moved his hands back up my legs, under my dress.

"Dylan," I moaned loudly as he started sucking on my neck. I gasped when he started kissing down my chest, sucking on my bare skin. "Holy shit, Dylan." I gasped as he bit the edge of my breast that was peaking out of my dress.

I bit back a scream as he slipped his finger into me. "Fuck," he moaned as he pushed his finger further into me. "You're already this wet for me, baby? Glad to know I still have this effect on you."

I leaned back and looked at him. "Are you kidding?" I asked, my voice breaking. "You're the only guy who has ever made me feel like this."

He looked at me softly before quickly smirking at me. "Good," he said huskily. Before I could say anything, he roughly pressed his lips to mine and kissed me desperately.

I moaned into his mouth as he slipped two more fingers into me. "Holy shit. We have to be quiet, Dyl." I moaned loudly. He stopped kissing me and started sucking on my jaw, up to my ear. I let out a moan as he slowly slid his fingers out of me.

"From what I hear, you're the only one making noise," he whispered into my ear, sending chills down my spine. I grabbed his face and aggressively pressed my lips to his. Our lips instantly started moving against each other's as I ran my fingers through his hair. As our tongues fought for dominance, I slowly slid off the dresser.

The second my feet touched the ground, I put my hands on his chest and slowly pushed him away. Without a word, I reached behind me and unzipped my dress. I smirked as my dress fell to the floor, leaving me in my lingerie. I looked up and instantly saw the lust in his eyes.

Dylan quickly tore off his vest and started unbuttoning his shirt. I stepped forward and put my hands on his chest, stopping him. I moved his hands and started unbuttoning his shirt myself.

I slowly slide his shirt off with a playful smirk on my lips. The second his shirt fell to the floor, I pushed him onto the bed. I climbed onto his lap and instantly pressed my lips to his.

It felt familiar as he leaned us back and rolled us over so he was hovering over me. As our lips continued to move in sync, I reached up and started taking off his pants.

I watched as he pulled away and took his pants off. "Holy shit, I need you so bad right now." I moaned.

"Then take that off," he said gesturing towards my lingerie.

I quickly slipped out of my lingerie, throwing it to the side. I instantly clenched my thighs together when I saw how he was looking at me, naked in bed.

"You're still so fucking beautiful," he growled as his eyes scanned every inch of my body. "Just like I remember. Damn, I can't tell you how many nights you kept me up these past few years."

"Well?" I smirked. "Are you going to just stand there and appreciate my body from all the way over there or are you going to take off your boxers and show me your appreciation?"

He let out an animal-like growl and he tore off his boxers and quickly crawled over me. He pressed his lips to mine, hungrily. I reached up and ran my hands through his hair pulling slightly, making him moan.

"I need you inside me, Dyl." I moaned when he started sucking on my hardened nipple.

"Ask," he moaned against my breast.

"Please, daddy," I said, slowly getting louder with each word. "I want you inside me. I need to feel you inside me. Please, daddy! Fuck me!"

As I begged him, he moved to my lips. I gasped as I felt him slip into me. "Holy shit," I moaned as he roughly pushed himself in and out of me. "I don't remember you being this big," I moaned as he moved his hips faster and faster.

"I don't remember you being this tight," he moaned.

I restrained myself from yelling out his name as he pushed into me even harder. I was flooded with pleasure as Dylan looked down at my, small grunts leaving his throat. I tried to ignore the look in his eyes as he watched my reaction to his movements.

"Fuck, baby," I said shakily, making him moan. "I. . . This. . ." I let out a loud moan as I lifted my hips, making him push farther into me.

"Oh, Dylan!" I screamed when I felt him push against my G-spot.

He smirked down at me as he continued to hit that spot. "Fuck, Y/N," he moaned between his soft grunts. "I don't ever think I've made you cum this hard."

"Well then," I gasped. "Don't stop!" A loud moan echoed through the room as he grunted and, somehow, pushed into me deeper. I gripped his back, my nails digging into his skin as he didn't stop.

Dylan was my first kiss and my first time. Before he left, we only had sex a few times but each time was better than the last. This time, after all these years, it felt different. The feeling I got from him was better than any of my other boyfriends I have slept with. It put the few times with Chase to shame.

"Holy fucking shit, babe," I almost screamed as I felt an orgasm building. I almost couldn't handle the feeling of him inside me. No other guy has ever made me feel the kind of pleasure that Dylan was able to make me feel.

"Are you close?" He growled, making my orgasm build even more. I let out a shaky breath as it got harder to try and stop myself from cumming.

"So fucking close, baby." My moans got louder as he pushed harder and harder into me.

"Don't you dare hold back, Y/N." He said, somehow pushing into me harder. "I want to feel you release. Release all over me, baby."

"Holy shit, Dyl," I screamed as I finally gave in.

"Fuck," he moaned when he felt me release. I gasped when I felt him release into me.

I let out a final moan as he pulled out of me and rolled to the side. We sat there, the only sound was us breathing heavily. We laid next to each other for another second before silently getting up and getting dressed. I slipped on my "Bride" bathrobe as Dylan put his clothes back on.

"You can't marry him, Y/N."

I looked over my shoulder to see him sitting on the edge of the bed. I turned around as he looked up at me.

"Dylan," I sighed. My breath got caught in my throat as he quickly stood up and walked over to me. He grabbed my hands and looked down at me.

"Please, Y/N. You can't marry him."

"Why not?" I asked, barely audible.

"Because. . . Because he doesn't love you like I do."

"You still love me?" I asked, tears forming.

"Of course I still love you," he laughed softly as he stepped closer to me. "I didn't come here to say goodbye or sleep with you one last time. I came to fight for you. For us. For what we had. For what we still could be. I never stopped loving you, Y/N. And that's why I can't let you marry someone else. I know I left but. . . He will never treat you the way I could treat you. I love you."

Time seemed to slow as he reached up and cupped my cheek in his hand. "Is there any way that you still love me?" He asked softly.

"Of course I still love you. I never stopped," I said, shaking my head. Dylan smiled as he caught a tear that had escaped with his thumb.

He leaned down and pressed a soft, gentle kiss to my lips. This kiss instantly reminded me of our very first kiss. He pulled away and pressed his forehead to mine.

"Please come with me," he whispered, our foreheads pressed together. He pulled away and looked down at me with soft eyes. " I can't. . . I can't leave you again."

I stood on my tiptoes and softly pressed my lips to his. I pulled away and reached up, cupping his cheek in my hand. "I'm not going to let you leave without me. Not again."

He smiled down at me before pressing his lips to mine. I smiled as our lips continued to move in sync.

"Let's get out of here," I whispered pulling away.

"I've never stolen a bride before." He smirked down at me, making me laugh.

"You're not stealing me," I explained as I slowly took a few steps back and walked over to the desk. I grabbed the ring off the table and the letter. I turned back to Dylan, showing him the ring and handing him the letter.

I watched as he slowly opened the letter and began reading it. Once he got to the bottom, he read the last line out loud. "I can't marry someone when I am still in love with someone else. I'm sorry."

He looked up at me with tears in his eyes. I laughed as he dropped the letter before quickly pulling me into his arms and pressing his lips to mine. Our lips instantly started moving in sync. I pulled away and bit my lip.

"You mind giving me a ride? I wrote the letter, but didn't think of an escape plan."

He laughed as he leaned in and pressed a soft kiss to my lips. When he pulled away, I bent down and picked up the letter. I walked back to the desk and put the letter and ring were someone would see it. I took a deep breath, looking down at the ring.

I smiled when I felt Dylan stand behind me and wrap his arms around me. "You ready?" He asked softly as he kissed my cheek.

I turned around and pressed my lips to his. I pulled away but looked down and laughed. "I umm. . . I should probably put on some clothes."

Dylan laughed as he smirked at me. I quickly threw on the white sundress I had planned to wear on the way to my honeymoon that night.

"Now are you ready to start a new life together?" He smirked. I nodded as he reached and grabbed my hand, instantly intertwining our fingers. I smiled as he quietly led me to his car. He opened the door for me before putting my suitcase in the back. The second he was seated in the driver's seat, I reached over and intertwined our fingers.

As he pulled out of the parking lot and headed down the road, he lifted our intertwined hands to his lips and pressed a soft kiss to the back of my hand.

I laughed as he suddenly pulled into a parking garage. "What are you doing?" I asked as we parked.

"I'm sorry," he smirked as he looked over at me. The look in his eyes made me feel like a teenager in love again. "I can't resist the urge to throw you in the back seat and fuck your brains out."

"Please do," I moaned as I practically jumped onto his lap. He was quick to slip off my underwear, almost as quick as I was to unbutton his pants and slide his boxers to his knees.

He was already hard as I started to grind my hips on his, slipping him into me. He tilted his hips up slightly, giving me better access. I let out a surprised giggle as he hit the lever, making the seat fall back.

"You know something?" He moaned as he switched our positions, him hovering over me as he finished undressing.

"That this is just like the time we ditched senior prom and had sex in the car while it was parked in the school parking lot?" I smirked as I tore off my dress and tossed it on the passenger seat.

"Even better," he smirked as he immediately starting pushing in and out of me.

A little while later, the windows were fogged up and we were wrapped around each other, naked, in the back seat.

"I can't believe I have you back in my life," Dylan said softly as his grip tightened around me and his hands rubbed my bareback.

"I'm never letting you go," I heard him whisper as I felt myself falling asleep. "Never again."

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