AN: This story is inspired by the song 'The First Five Times' by Stars. The idea is that each chapter will detail the first five times Oliver and Felicity have sex, and how each time changes their relationship. I hope you all enjoy this story, it will be very smutty but hopefully the emotion behind the smuttiness will come through. Another warning, this is definitely not fluffy smut. It'll be an angsty ride. I feel like there's no other way to do with Olicity though, given the person Oliver is and the dynamics of he and Felicity's relationship. I just feel like there will be lots of angst while they're in the process of falling in love so I can't help but write them that way. Well this authors note is getting long, thanks for reading and please let me know what you think!

The First Five Times

I.

The first time they fuck is after her first date with Paul Whitman.

Paul is a business man. He worked on a deal with Oliver and since she's Oliver's Executive Assistant (which, ok, 10 months later and she's still not as honored by that job title as she pretends to be) she spent a fair amount of time with him.

He asked her out on his last day working with Oliver.

Her first instinct was to say no because, well…he's a business man. And his name is Paul. She never really pictured herself dating a Paul.

But on the other hand, he's so damn nice she swears birds dress him in his Armani every morning. He has a great smile. He's smart.

He likes her (and he's not afraid to admit it, to her or to himself, and isn't that a novel idea).

Honestly he's kind of an amazing guy and she had a kind of amazing time with him.

Oliver doesn't find the situation quite so amazing.

When Felicity shows up at the lair after midnight, planning on checking in on some surveillance she had set up earlier that day then getting the hell home, she's met with Oliver's glare-y, sullen face in her computer chair.

'How was your date?' He spits the word 'date' out with so much venom she actually stops in her tracks and looks at him quizzically.

'um, it was very…date-like. Why exactly are you in my chair? Shouldn't you be throwing sticks around or hanging from the ceiling or something' the smile he gives her has to be the least genuine smile in the history of smiling.

'Aw come on Felicity. Give me all the details. I'm dying to know, really' He's standing up now and she's momentarily distracted by the way he's standing. He's tense all over, muscles in his arms and chest clearly showing through his thin grey pullover. The veins in his neck and forehead are bulging and she's glad his bow is nowhere in sight. She's seen him like this before, many times actually. But his looks and scathing tone have never, not once, been directed at her.

'ooooook…look, Oliver, I'm not sure exactly what happened tonight and I'm really sorry if I missed something big. I'm just gonna take my tablet and check everything out from home. You seem like you need…some time alone. And maybe a nice bubble bath?' he doesn't crack a smile. 'no? Bubble baths are like the single most relaxing thing ever so…your loss. Suit yourself…enjoy your…whatever it is you're doing' she shrugs, not wanting to let whatever it is that Oliver is stewing about ruin the first date she's had in…months.

She's halfway out the door when her path is blocked by the door shutting right in front of her face. When she turns around she's blocked in by 6 + feet of Oliver Queen.

His right arm is stretched out, holding the door to the lair closed. His left is above her head and god damnit.

'Felicity…' the tension in his body is still very much there but his voice is soft and as close to an apology as she'll get.

'Oliver' she deadpans.

'don't worry about it. You need to be alone, I get it. I should have checked with you or Digg before just showing up, hey where's Digg anyway - '

He grabs her shoulders and she's so shocked by the sudden contact she forgets what she was saying and why she was saying it.

'please…don't. You don't need to apologize for anything. I don't know what the fuck's wrong with me…'

His hands skate down her arms as he's speaking. He's holding her wrists now and she's pretty sure she hasn't breathed since he first touched her and that really sucks because she's been working on that. She had made it her number one priority to always breathe around Oliver Queen, especially when in physical contact with him. Or when he was working out. Shirtless. Or when they made eye contact. Anyway she had been doing so good lately and look at her now.

'Did you kiss him?'

The question lingers for several moments. He's not even looking at her, but when he does raise his head to look at her, his whole demeanor has changed. He is unreadable and she can't stand when he does that.

'No'. As soon as she says it she mentally kicks herself. That's not how she was supposed to respond. She was supposed to go off on him about how it was none of his business and maybe she did what's it to him?

But honestly she's never been one to play those games. And she's not stupid. She's gathered over the last few minutes that Oliver is dealing with some type of jealousy over her date with Paul. She's not going to pretend she hasn't had moments exactly like this whenever Oliver is fucking some girl. She's not in over her head enough to mistake Oliver's jealousy for real romantic feelings though. She gets it. They've developed an odd, probably unhealthy, attachment and it gets confusing when other people get involved.

The thought flickers through her mind that she knew exactly what she was doing coming here after her date, that she knew exactly what would happen, and she did it anyway. She can't be mad at him for doing exactly what she knew he would do.

She's still leaning against the door, and Oliver is still holding her wrists. It should be odd, but it's not. He has a thing about her pulse. She guesses she's had enough close calls by now that he gets some type of comfort from it. Regardless, she's used to it enough to be able to function (she'll never really be used to it)

When he lifts her wrist to his lips, though…that, she is not even half way used to or prepared for. That one action sends a volt through her that she's experienced maybe once before(that first time he pushed her hair away from her face…she was blushing for days).

She finds herself stepping away from the door and towards him and no no bad what are you doing.

His body is buzzing with something and she's not so far gone that she assumes it's because of her.

'Oliver…what happened tonight?'

He drops her wrist and turns around at that and she hates that she already misses his touch.

He's silent for about a full minute and she can tell he's debating whether he really wants to tell her.

'I was too late. Digg got the intel as fast as he could but by the time I got there…it wasn't fast enough'

It was starting to come together. She had no doubt she could have gotten the information he needed in time for him to do whatever it was he needed to do. The reason she had chosen that night for her date was precisely because she knew their mission that night only required her to do things she could have done in her sleep. So she let Digg take over her computer and told the boys she'd see them later. It never occurred to her that a routine mission would fail just because she wasn't there.

Apparently she was wrong.

'Did anyone…' it was still hard for her to acknowledge the life and death matter of most of their missions.

'Yes'

'Oh my god…Oliver, I'm so sorry, you should have called me, I would have left…why didn't Digg call me?'

'Because I shouldn't need you this much Felicity!' His voice was deeper than she'd heard it before, dangerously close to his disguised 'Hood' voice.

'Goddamnit! I used to do this alone, I didn't need anyone! Then you…happened. And now I can't even do a simple drop-in without your help'.

She had been walking towards him as he was speaking and when he was done she put a hand on his shoulder. He turned around to face her.

'Oliver. That's not true. Tonight…was a fluke. You and Digg were unprepared, but I know it's not because you were incompetent. It's like you told me before, this is the thing about what we do. Sometimes we don't win'

At that moment she noticed the small black spot underneath his right eye. He hadn't worn the eye makeup since Barry had given him the mask…that was months ago.

'Oliver…you have makeup under your eyes…why didn't you wear the mask?'

She lifted her hand to his face and began to brush the makeup off with her thumb. He once again grabbed her wrist, rubbing circles around the spot where her pulse was beating (and getting quicker by the second).

'You weren't here to put it on'

And she stops breathing.

He really does need her. And it scares her to death.

It's like he can hear her thoughts. She hopes she didn't say it out loud (wouldn't be the first time she put into words something meant only for her head).

Suddenly his arms are around her waist and she's being lifted up and she's sitting on her desk, dress rucked up around her waist and Oliver, huge, imposing (gorgeous) Oliver is standing between her legs. His fingers find her wrists again, except this time he crosses one over the other, holding them down behind her on the desk. The position they're in is…precarious. With her arms being held down behind her back, her chest is pushed out more than usual and her dress is more low-cut than usual, because, oh yea she just got back from a date. A date with someone most definitely not the huge, imposing, gorgeous man currently standing inches away from her…everything.

The hand that's not holding her wrists behind her back traces from her neck down to the apex of her thighs and oh my god she's not sure she'll make it through this if just a simple touch affects her like she's currently being…affected.

'You're fucking wet' he growls in a suspiciously accusatory voice.

'yea well whose fault is that!' she snaps immediately. That brings a smile to his face…if his earlier smile was the least genuine smile in the history of smiling then this one is the most…lascivious smile in the history of smiling.

They don't talk again for the next 20 minutes (well not in full sentences anyways).

It's intense. Oliver is intense.

She can't even count how many fantasies she's had about what he'd be like…sexually. She always imagined he'd be intense. thing is, she never had a fantasy about actually being with Oliver. Her fantasies are always of Oliver with a faceless girl. So to actually experience it…definitely lived up to everything she'd ever imagined sex could be, every dirty novel she's ever read.

Felicity's not unexperienced with sex, per say, she's just never had sex like this before.

No one has ever taken control like Oliver. It makes sense that Oliver is…dominant, considering his personality and control issues. She never thought she'd be into that type of thing but…

She liked it.

A lot.

She liked it when he held her wrists behind her back as he touched her all over and then eventually got on his knees in front of her and feasted on her like he hadn't eaten for months.

She liked how he told her what he wanted her to do ('look at me' 'turn around' 'tell me what you want' that last one was her favorite. He did everything she said she wanted).

She liked it when he stood back and unbuckled his belt, staring her down head to toe.

She liked it when he told her to touch herself, make herself cum, told her he wasn't going to fuck her until she did.

She liked watching him lean against the back wall of the lair casually jerking himself off as he watched her touch herself for him.

But she really liked the way he slowly walked back over to her after she had made herself cum, the way he so confidently and deliberately pulled her hips to the edge of the desk, the way he slowly eased himself in her as if he was savoring every moment (she sure as hell was).

The way his fingers dug into her hips right before he started thrusting.

The way he kept eye contact with her the entire time he was inside her (at one point she closed her eyes and her head lulled back. He instantly grabbed her by the hair, forcing her eyes back to his. After that he pulled her even closer and thrust inside her so deep she couldn't tell where her body stopped and his began, staying there for what seemed like minutes but was probably only a few seconds. 'I want to see you, all of you, every second I'm inside you. Don't look away from me again, understand?'. All she could do was nod).

She liked the way he didn't miss a beat when she came around his cock. Sweat ran down his face as he kept thrusting in and out while she spasmed around him. 'it's too much, omigodoliverican't' she had chanted over and over. He simply dug his fingers into her hips again, put his forehead against hers and whispered 'Fuck me you're beautiful'.

Not 5 seconds later he was coming. She had a mini internal freak out because he was still inside her, but then she didn't feel anything and realized he must have at some point put a condom on without her noticing.

'Oh my god THANK YOU for the whole condom thing, wow you must think I'm a huge slut I mean I didn't even ask you to put a condom on! I mean I guess the fact that I just let you do unspeakable things to my body could also be a sign of the whole huge slut thing…but I think not even remembering a condom is more slutty. But on the other hand…' she was rambling. There was a huge neon 'STOP' sign flashing in her head but in typical Felicity Smoak fashion she .talking.

Then he kissed her for the first time.

It was a surprisingly sweet kiss. She has a vague thought about how backwards this all is, the kissing after the sex, the fact that Oliver didn't give any indication he was interested in her until after she finally met someone else who wanted her…

But those things weren't what she wanted to think about when Oliver was kissing her.

So instead she thought about how his lips were chapped.

She thought about how as sweet as the kiss was there was still something about how Oliver was holding her neck, how his other hand traveled down her body like he owned it.

She thought about how much she liked that.

And then his hand found her wrist again and his thumb started rubbing the familiar circles around her pulse.

She's not sure she'll ever forget that moment (and she can just see her future self desperately trying to forget). In that moment she realized how in over her head she really was here. She had just had the most intense, crazy, amazing sexual experience of her life with this gorgeous, rich, crime fighting, damaged, beautiful disaster of a man. He had saved her life more than once and she had saved his too.

Things like this didn't happen in anyone's real life, much less Felicity Smaok's.

But here she was.

Naked, arms around naked Oliver Queen, his thumb feeling the pulse on her wrist and his lips kissing the pulse on her neck.

It's too much. What she's feeling…it's too much. This could go so wrong in so many ways that she doesn't care to think about right now.

So she decides to take it for what it is. Oliver is perfect for her, sexually. He knows just what to do to make her go insane with pleasure, but he never took it too far. She's never been with someone who could take her to the places Oliver just did. So she'll focus on that. Just sex.

Oliver's lips still and he drops her wrist.

'What was that?' he asks gruffly.

Oh shit. She said that last part out loud.

'Oh um, you weren't supposed to hear that. But you did. So I will now explain. I guess that's my only option here'. He just stared at her, as he had done so many times before, waiting patiently for her to get to her point.

'Just sex, right? I mean I assume that's what you want this to be too. But even if you don't I think…I think it's the best option. I mean we have a lot going on….here. What with the secretary thing and the Hood thing and just…there's no reason to make this more complicated than it has to be, right?' His brow raises quizzically at that.

'Explain' she blushes at the command. Now that she knows how…commanding he is naked she's not sure she'll ever be able to disassociate that from his general commanding personality as her boss.

'Well I mean the sex was…really good. Clearly we're sexually compatible. There's no reason to pretend that's not true. But other than that…oh god I totally just made a huge assumption, I mean the sex was awesome for me but maybe you hated it, and that's totally ok I mean it would suck because I've never felt anything like that before but if you never want to do it again I'm totally cool with that…'

'Felicity. I didn't hate it. It was…I didn't hate it.'

Ok then.

Not exactly a glowing review.

He must have been able to see the disappointment on her face.

'What I mean is, you're right. We're very…compatible. Sexually. I feel like I should tell you…I'm not usually like that. I mean I am, but I normally hold back with the uh, the forcefulness and…such'.

She's kind of shocked he's actually talking to her about it. She fully expected him to pull his strong and silent routine and walk away without her knowing anything about what was going on in his head.

'I apologize if anything I did was too much. I didn't back off because, well, it seemed like you were enjoying…everything' he smiles slightly to himself and she can almost see the images floating around in his head.

'Oliver…you have nothing to apologize for. You were…perfect' she sighs and she doesn't even care how pathetic she sounds. It was an experience she'll never forget and she thinks he deserves to know that.

She can tell she's made him uncomfortable so she gives him a small smile and turns to find her clothes cause oh yea she's still naked as the day she was born.

Before she can pull her dress over her head Oliver is standing very close to her and grabbing her wrists (and what the fuck is this obsession with her wrists?), pulling them and the dress down to her sides.

'Wait…I want to look at you. Once more'. Well she can't argue with that. She herself was pretty disappointed when he pulled his boxers back on while she was rambling about condoms earlier.

So she stands there and lets Oliver Queen run his eyes and then his hands over her naked body.

He doesn't have the look in his eyes that she'd expect a guy to have when looking at the naked body of the girl he just banged on the desk of a crime fighting lair. The look on his face is…intent. Like he's studying her. It makes her much more uncomfortable than she likes.

Once again he seems to read her mind (which, scary. No one should be exposed to what goes on in there) and reaches down to grab the dress from her hands. He lifts it over her head, turns her around so her back is to him, and does up the zipper.

'thank you' he whispers and she thinks she'll be thinking about the way his lips brush her ear and the way his breath feels on her neck for a long…long time.

After he walks away she puts her hair back in her sensible ponytail.

'So about what we were talking about before…we're on the same page? Chalk it up to hormones and good sex and…all that, right? Just sex?'

He's studying her again and she thinks there's no way he doesn't see right through her and her bullshit 'just sex' thing.

But instead of calling her out he nods his head. 'Absolutely. We are definitely on the same page. I'll see you at the office tomorrow. I have a meeting at 7:30 and I'd prefer if you were there for it. After that we can work on salvaging whatever we can from what happened tonight'.

She's confused for a moment by what exactly he means by 'salvage'…salvage their friendship? She guesses it makes sense, sex can really screw everything up.

It takes her awhile but it finally clicks that he's talking about the failed mission. Back to business then. She's relieved at first but then she's a little disappointed that he can move on so easily from an experience that's sure to rock her for the foreseeable future. In fact she's more than disappointed, she's fucking sad. Which makes no sense cause she's the one who pushed the 'just sex' no strings attached thing, it was only natural for Oliver to agree and then proceed with business as usual.

She still wants to cry, though.

But she doesn't. Instead she says:

'Of course. I'll see you in the morning' and starts walking towards the door.

She stops in her tracks when she remembers her other plans for the next day. Paul had asked her to lunch. She had accepted.

She turns and finds Oliver buckling his belt.

'Oliver…one last thing'. She pauses and Oliver motions for her to get on with it.

'Well um, Paul…Paul asked me to lunch tomorrow. I told him I'd go but that was…well before…you know'

'Before you came back here and we had sex. Yea, I know'. She forgets that he can be honest too sometimes. So much of his life is wrapped up in lies.

'Right. Well I was just wondering…if you don't want me to go. Not that I need your permission. Of course I don't. I just…want to know what you think, I guess'.

Without hesitation he tells her she should go. He also tells her Paul is a good guy and that he's 'glad' they're spending time together. Felicity scoffs internally at that because she cannot remember the last time Oliver Queen was glad about anything (other than your standard 'I'm glad you're ok' after the ever increasing near death experiences she and Digg have had over the last months).

Felicity cries as soon as she gets to her car.

She spends the next few hours listening to The Civil Wars and re-living every second of the-oliver-experience. She gives herself one night to both enjoy and wallow in the fact that she just had mind blowing sex with the guy she's been crushing on (and for the last few months, much more than that) since the day she met him.

The next day she walks into the office at 7 am sharp. She wears a dress with a longer skirt than all her others. Her hair is in a ponytail. Glasses perched on her face.

Oliver is already schmoozing the man he will be meeting with soon and when Felicity walks in she tries not be disappointed that he barely looks her way as she makes her way to her section of office.

'Ms. Smoak?' he stops her before she rounds the corner.

'Yes, Mr. Queen?'

'Would you get a cup of coffee for our guest? And one for myself as well'.

She contemplates making up a bullshit excuse about the coffee maker but then…

'Of course, Mr. Queen. Cream and sugar?'

AN #2: So just a clarification...I am definitely not going for a christian grey/fifty shades thing with the way I'm writing Oliver here. There will be no whips. There will be no chains. There will be no room of pain or whatever. Ever since I first started watching Arrow, even before I started shipping Olicity, I've pictured Oliver the way I'm writing him here. I just think it's very likely that he'd be super intense and kind of dominant in the bedroom. And it's just my opinion that Felicity would be kinda into that. I just wanted to be clear that I'm not trying to re-write fifty shades here lol. I'm simply writing these characters the way they are in my head. Thanks and again hope you all enjoy :) chapter 2 coming soon!