tagRomanceRoommate Romance

Roommate Romance


This story begins the way most stories do. With a girl and a boy. My name is Katie and I am that girl, though it took me a while to figure out who the boy was. You see, I had been seeing this guy off and on through college and it never really had a definition. We sort of dated other people, but somehow always ended up in bed together. And it was fun and familiar and incredibly unhealthy. Jake stressed me out beyond anything else in my life. Midterms, finals, graduating, job hunting, and life in general all fell within the realm of controllable. But him... he was chaos. He kept me on baited breath, waiting and hoping for something more.

"Well don't you look stunning tonight." Dan smirked at me from the couch of our living room.


"Hot date?"

"Yeah, I'm meeting Jake."

Dan's eyes narrowed for the tiniest, fraction of a second. I knew he didn't really approve. But he knew how I felt and kept his opinion at bay. You see, Dan was one of my best friends. From the moment I met him at my cousin's house warming party, I knew he was special. Tall, funny, and confident, he was everything I wasn't. Now I'm not saying I'm not happy with who I am. I'm very content being the quieter, mousy girl with her nose in a book, but whenever you're around him you can't help but feel... more.

Stacy, my cousin, met Dan her third year of college and everyone, including me, thought for sure they would get together. They seemed perfect for each other and everyone in our family secretly thought they were hiding a relationship from the rest of us. But after a couple of parties and plutonic coffee dates it became obvious nothing could be farther from the truth. They were, truly, just best friends. Something I respected them both for, because there had definitely been opportunities where their relationship could have taken a more physical turn. Especially with all the encouragement and goading our group of friends laid on at every chance.

Anyway, Dan moved around a lot after school but when he finally finished his work abroad and moved home he needed a roommate, and so did I. And for the last several months, he's become one of my dearest friends. Even listening to me go on and on about Jake, and how I want more, and how he was hesitant and indecisive about our relationship, and how he avoided and dodged any real conversations about our future. But despite everything, I still wanted him. Still needed him. And I could tell how much it frustrated Dan.

Now many of you are probably thinking that Dan is in the friend zone. But this couldn't be farther from the truth. We just didn't see each other like that. Not that we hadn't thought about it. It just, didn't seem smart. We were just too different to be romantically capable... right?

"Well, you should knock him dead in that dress."

"That's the idea." Dan turned away, and went back to his laptop. Usually he was going out or watching a game or playing some new game on his Xbox, but once in a while he'd sit down and write. And when he'd write, he'd go at it for hours. It was amazing and also a little unnerving to watch the normally boisterous and loud guy I knew so well, sit in silence for hours with a look of deepest concentration on his face. I liked to read when he was in one of his writing moods. Almost as though his thoughts supercharged the air of the room. It made reading that much more intense for me. And I loved it.

"Got any plans tonight?" I asked.

He took a moment to answer me. I could see his eyes darting back and forth across the screen. The tapping stopped and a moment later he looked up.


"Plans? You doing anything tonight?"

"Oh... Nah. I'm grabbing coffee with Stacy tomorrow morning, so I'll probably go to bed early." He forced a smile and asked, "How about you? Where are you and Jake going?"

"I dunno yet. He's taking me to dinner in the Mission."

""That should be fun. You coming home tonight or you going back to his place?"

I couldn't help but chuckle slightly. "Depends how good dinner is." I told Dan everything about Jake and me, including our love life. I'd never really done this with anyone before, but he was so uninhibited about sex and stuff that I didn't feel weird talking about it.

Knock, knock, knock.

Jake was here. Dan gave me a final, fleeting smile and went back to his computer. I walked to the door, knowing full well I'd probably be venting some new frustration about Jake to Dan tomorrow and already feeling guilty about it. You see, Dan never really dated. Despite his confidence and charm, he had very little with anyone romantically. Not to say he was celibate. I came home once and heard a very noisy bout between him and some young lady I never did meet. I teased him for days about it, but he'd just laugh with me... more proud than anything else. Still, such nights were few and far between for Dan. He just didn't go looking for it. Just let it find him once and a while.

And then there was Jake. I opened the door to see his familiar pale face. He and Dan were so different. Where Dan was almost six foot four, Jake was only five ten which still towered over me at a petite five feet. David was athletic and Jake was scrawny and skinny. And Jake's eyes were dark. So very dark. I'd lose myself in them wondering what was looking back at me. While Dan's were the faintest blue grey and seemed to twinkle whenever he laughed.

"You ready?" He said with the same half smile that had made me bite my lower lip all those years ago.

"Yeah. Let me just get my coat." Walking to the closet, I glanced quickly at Dan hoping for a reassuring smile or nod, but he was staring at the screen; his eyes weren't moving.

"See you later!"

"See you."

I knew what he was thinking. And I secretly knew it too. That tonight wouldn't be different. That I'd come home feeling the same uncertainty and emptiness that always followed an evening with Jake. But I had to hope. I needed there to be a chance that tonight could be different. That tonight we could move forward. Because, if we didn't it meant I'd been used. It would mean that I'd fallen for the same play again. And the cycle would keep repeating itself. I needed that hope; Unwarranted and blind hope that the scrawny, dark haired boy smiling that smile really did care for me. And that I wasn't the dumb girl who was there when he needed someone to console him, or someone to fuck.

The car ride felt odd. Normally Jake talks a lot, about himself or his music, but tonight he seemed distracted. He had the look of someone running a conversation through his head over and over. That look of concentration people get when they're stealing themselves to do or say something important. It gave me goose bumps, seeing him with that look. Because I started doing the same thing. Picturing him telling me how he felt and where he wanted this, by which I mean "us", to go. I looked down and stared at my hands, nervously rubbing them together. And then his hands, bony and strong, were there too. He took my hand, and I took his, and I looked up. There is was. The smile that made me forget everything except for how his body felt against mine and how his hair smelled when I held it firmly against my chest, lost in the pleasure that he gave me.

"We're here."

I snapped out of my memories and saw a quaint little restaurant I'd never been to. The trees outside twinkled with lights and the windows were fogged slightly.

"Where are we?"

"Little place I found after a gig a few weeks ago." He took my hand and led me inside. "Let's get our table. There something I want to talk to you about."

The inside was warm and comforting, like a ski lodge. And it reminded me of when I used to go to Tahoe with my family while growing up.

"Anything to drink?" I hadn't even noticed the waitress come over.

"Rum and coke." He always had rum and coke.

"And for you?"

"Um…" I was still thinking about the Christmases in the Sierras so I figured what the hell. "Do you have hot chocolate?"

"Yeah, want a cup?" She asked with a smile.


Everything here seemed magical and surreal. Like a town inside a snow globe. Even the hard wood architecture seemed whimsical in a way.

"Katie?" His hand on mine snapped me back.


"You okay?" He seemed slightly concerned.

"Yeah. This place just reminds me of…"

"Listen, I wanted to talk to you about something." His hand left mine. "Remember how I told you I found this place after my last gig?"

I nodded, not entirely sure where this was going but happy that he was being direct for once.

"Well, a producer heard us there and is really interested in us."

My mouth dropped. "You did it. You did it! Oh my God, congratulations!"

A prideful smile stretched across his face. "Thanks"

"So what does this mean? Are you going to make an album or…"

"We're going on tour."

"Oh!" His smile faltered "… where?"


"Europe? Well, that'll be fun but… how long is it?"

"Six months." The smile on his face faded completely. "We're supposed to leave at the end of the month."

"Well, six months. That's, that's not too bad."

"Katie… I know it's a long time but if you're willing to wait for me..." he said.

"Of course I will. You don't have to worry. I'll be right here when you get back."

"Thanks Katie." There it was. That smile. "I was so worried you'd want to break up."

I took his hand and tried to give him the most reassuring look I could muster. "How could you think that? I'm in this."

"Yeah, me too."

We waited there, looking into each other. But after a moment, seeing he wasn't going to push on to what had to be said, I made the next move. "So, are we boyfriend and girlfriend now?"

"I guess we are."

My stomach turned over. I finally knew. I knew where we stood and how he felt.

"I'm going to use the bathroom real quick before they take our order."


He got up and moved down the back hallway, leaving me melting into my chair. I literally felt warmer, almost feverish, with excitement. At which point I realized I was sweating profusely. It always happens when I'm nervous. I glanced up and saw the waitress busy with a family a couple tables away, so I got up knowing she'd be occupied for a few minutes.

The cool water felt great on the back of my neck and I pressed the damp paper towel against my skin. As I looked back at myself in the bathroom mirror I couldn't even suppress the wide smile spreading from ear to ear if I'd wanted to. I couldn't wait to tell Dan about tonight. Not to rub it in his face, but just because I knew he'd enjoy the change of tone. Most our conversations about Jake were not the most cheerful.

Figuring Jake would be wondering where I went I made to leave the bathroom, but as I opened the door I heard John's voice. I was about to go to him when something about the tone made me stop. It was harsh, almost cruel. Something I hadn't heard before.

"Yeah man, she totally bought it. While we're living like rock stars she'll be waiting here for me to come home. Dude, I know. She's so easy. Had to make sure I'd have a little pussy waiting for me when I got home, you know. Yeah, I'm still coming over later. See if Jennifer will come. She's always got an entourage of hot sluts with her. Peace."

He moved past the door, his hard sole shoes clomping on the hardwood. And I couldn't move. I couldn't even feel. It felt as though the walls were coming in and crushing the air out of me, making everything go dark.

I don't know how long I was in there; A minute, maybe ten. But the waitress knocked on the door after what felt like only moments and asked if I was doing alright.

"Yeah…" I mumbled weakly, "I'll be right out."

I wiped the tears from my cheeks and unlatched the door.

"Everything okay?" she asked with her same cheery smile.

She took one look at me and knew instantly everything was about as far from okay as it could be.

"Is there a back door I can leave out of?"

"Through here."

She led me further down the corridor and through a door marked "Staff Only."

I managed a feeble "Thanks." She hugged me. I don't know why, but it made me uncomfortable. She'd just helped me, but it reminded me of being back in the bathroom and the walls crushing me. Someone yelled something from back inside the restaurant and she scurried off, leaving me in the no longer magical twinkle lit tress. I started walking.


Oh no. Please no. Just get away from me. I never want to talk to you again.

"Katie!" Jake caught up.

"What's up?"

"Leave me alone." I pushed past him and kept walking. He followed behind me.

"Did you not like the restaurant? We can go somewhere else."

"I never want to go anywhere with you again. I never want to see you again."

He had a bemused look on his face and asked innocently, "What are you talking about?"

"I am not your at home pussy." His face fell. Silence. "Yeah, I heard that."

"Katie, you don't…"

"Don't ever come near me again. Don't call me again."

He was stammering now, grasping at anything. "Look, that was nothing. I'll come by tomorrow when you've calmed down and we can talk about…"

"I guarantee if you come by our house ever again, Dan will beat the shit out of you."

His eyes became stony, a look that mirrored the tone I'd heard from the bathroom. "Fine. Forget it. You weren't a great lay anyway."

"Fuck you!"

He turned and flipped me the bird over his shoulder. I watched to make sure he left. He turned the corner, and he was gone. I screamed out into the night, collapsing against the wall of a building. I started beating my fist against it until it was numb.

Tears began to fall into my lap where my hands were rubbing over themselves. I thought back to the car ride here, and how everything had changed since then. My hand hurt from slamming the wall. There'd be a bruise there tomorrow and I'd regret having done it. Then I did the only thing I could do. I got up and walked. Walked home. I wanted the time and seclusion before facing Dan.


It took me over an hour to get home. The walk had given me time to cool off, literally. I'd left my jacket at the restaurant and a chill wind had picked up about halfway home. I entered the dark house and thought for a moment of going to bed and trying to sleep. But I knew I wouldn't be able to. I walked down the hall to Dan's room, already feeling guilty about waking him in a few moments. His door always creaked, and as I edged into the room he stirred slightly.

"Dan?" My voice was a little hoarse from screaming.

It took a moment for him to come out of his dream, but he looked up a few seconds later. "Katie?"

"Sorry, I know you're… can I come in?"

Still half asleep, he raised the covers on his bed with his long arm, inviting me to join him.

"Hurry, before you let the warm out." I pulled off my jeans and socks, and crawled into bed next to him. This wasn't really that odd for us. We often cuddled while watching movies and having been roommates for a few months now, seeing each other in our underwear wasn't exactly news. "Jesus, you're freezing."

"Yeah. I walked home."

"What? Why didn't you call me?"

"It's fine. Well no, but I needed some time to process." He already knew what I was going to tell him. I could sense it. I put his arms around me and held me against him. "Jake, he…"

"I know. I'm sorry."

I started crying again. I knew Dan could feel my tears running down onto his arm. He didn't say anything, but just squeezed me a little harder. I didn't mind this. It didn't remind me at all of the bathroom walls. More of a favorite blanket you wrap up in against the cold.

I woke up a few hours later. It was still dark and Dan's arms were still around me. I shifted slightly to get more comfortable when I felt it. Hard and erect, pressed firmly against my butt. My cheeks flushed, and I felt the same embarrassment as the time I'd walked in on him masturbating.

"Dan?" He continued to breathe heavily, completely out. I tried to shift away slightly but Dan's arms pulled me in closer, pressing his body firmly against mine. And with that, his tented boxers moved slid further between my legs.

A shiver ran down my spine and the smallest gasp escaped my mouth as his hardness tickled me. My eyes rolled back and slowly my hand met Dan's and I began to brush his fingers. And then I hit me whose hand it was. Who I was lying beside, and what the consequences of this would be.

I reached behind me and slid a hand between our bodies. I finally reached what was intruding between my legs and pushed it down, hoping I could pin it back in his waistband. As I took hold of it, the memory of it being in his hands flashed through my head again and I remembered what it looked like. Not monstrous, but a bit above average if the quick glimpse I caught had been accurate. Now with it in my hands I could feel that I'd guessed about right. With a sneer and a moment of bitterness I thought to myself, "Well, you're bigger than Jake." Then realized how stupid I was being; Objectifying one of my best friends.

I tried to maneuver his prick from my crack, but Dan began to stir again. I froze. "God, don't wake up!" I pleaded in my head. The last thing I needed was for him the wake up with my hands wrapped around his junk. Dan's grip on me loosened slightly and I took my window. I pulled him out and up, and trapped it in the waist band. Unfortunately the top inch or two was poking out of the top, but at least it was contained. And he'd never know that I had to…

He moved again. This time further down the bed, but his underwear didn't shift with him. And now I was in the same predicament but without the barrier of boxers between us. "Was he awake? Or did he always move around this much in his sleep?"

I tried to see if Dan was still out, but his face was obscured in darkness. I thought about just leaving for a second, but I knew that would wake him up and he'd feel terrible if he woke up to me leaving i, his underwear off. Maybe if I just…" I slowly turned over to face him and could now clearly see he was still asleep. I closed my eyes again, now with a little space between us and tried to get back to sleep.

Maybe 10 minutes passed when I resigned that I wasn't tired. That between Jake and what had just happened, I was too riled up to sleep. I contented myself by watching Dan sleep. Whatever he was dreaming must have been good, because he was smiling slightly. His hair had fallen into his face, so I brushed it off his eyelids. And at my touch, his arms pulled me in again. And now his prick slid right between my legs, resting against my own soft patch.

I moaned, as silently as I could. His naked shaft had rubbed against my clit as it pushed between my legs, momentarily making me see stars. I reached down to move it. It was so warm and hard, yet soft. On top of everything else I'd been feeling and gone through that night, I was also beyond aroused and frustrated. For days I hadn't had the chance to deal with the growing agitation I'd felt and thought It would have been dealt with after dinner with Jake. Yet common sense prevailed and I began to push it down again with my fingertips.

I noticed that the top of the shaft was wet. Not from him, but from me. And as I pushed harder down, my fingers slipped off to the side and it slapped back up against me. I had to shove my knuckles into my mouth to keep from yelling out. God, it felt so good. And whether it was his dream or instinct, he pulled his hips back slightly and then thrust forward again.

I was powerless. I was in heaven. Whether it was a vindictive pleasure or just pure bliss, I didn't care. All that mattered in that moment was the cock pressed up against my pussy, and how good it made me feel. But after a few thrusts his motions stopped, and his face nuzzled back into his pillow.

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byCrippledWing© 10 comments/ 20431 views/ 18 favorites

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