Spoilers: Some mild season 8

Summary: Set around season eight, but this is AU. It's Oliver's birthday, and he wants to play a game.

Author Note: Prompt based - "Truth or Dare". Prompt from Jo_Winchester

All comments and reviews are appreciated. Seriously. They are my drug of choice - do not deprive an addict!

It was late on a Saturday night and Chloe found herself in a private elevator heading to Oliver's penthouse. Most girls her age were out enjoying life - socialising, dancing, drinking, dating, having sex. Chloe couldn't remember the last time when she had done any of those things. In fact, since her divorce from Jimmy she knew she hadn't done any of those things, but God did she want to. If only she could get the nerve to walk out her front door for anything but work.

Her purpose for coming to Oliver's tonight was to drop off files for the League's next mission. It wasn't as if she had anything better to do tonight. He was probably out celebrating his birthday with Lois like normal so at least she knew she wasn't going to walk in on a potentially embarrassing situation. Finding Oliver sexually compromised with the latest debutante on his arm was not her idea of fun.

"I really need to get a life." She muttered to herself as the doors finally opened.

She was surprised to discover that Oliver had left on the lights - he had even left his iPod playing in its dock. "So much for the Emerald Archer going green." She said as she turned it off.

"Heeey Chloe!" Slurred a drunken Oliver Queen. "What's up?"

Chloe felt as if she had jumped ten feet in the air. "Jesus Oliver, what are you doing sitting on the floor?"

He was laying on the floor next to his couch with half a bottle of tequila next to him. "I'm not sure. I'm sure I started off on the couch."

She put the files down on his desk. "I came to drop these by birthday boy, I didn't think you would be home yet. Shouldn't you be out with my cousin, being tossed out of every bar in Metropolis right about now?"

"Nope. She's with Boy Scout on assignment, last minute call."

Chloe walked over towards him and offered him a hand up. She really should have thought it through before helping him to his feet. If her size wasn't enough of a hindrance then her heels certainly didn't make the task any easier. After eventually getting him to his feet she edged him over to the couch. As he dropped heavily onto the seat he used the arm she was supporting to bring her down with him.

"Well, happy birthday anyway Oliver. It certainly looks like you're getting into the spirit of things by yourself." She said leaning forward to pick the bottle from the floor.

" S'not so fun by yourself. But now you're here you can celebrate with me!" He tried to nudge the open bottle towards her lips.

"Oliver I'm not drinking with you."

He leant forward as if he was about to tell her a secret. "You really should humour me. It's my birthday." He told her in a stage whisper.

She sighed before taking a swig from the bottle. "There. Happy?"

"That was pitiful Sullivan. We're supposed to be celebrating my existence, so drink up." He said nudging the bottle towards her again.

"Oliver, I drove here and I have work to do, I can't just take the night off."

"I am your boss. I can give you the night off and I'm sure I can afford to call you a cab. And as your boss I order you to spend time with me on my birthday."

She wanted to make a snaky retort about never actually listening to his orders, but despite his jesting he actually sounded a little bit lonely with that last sentence. She didn't want to feel like another person who had let him down today, she knew how much Lois and Oliver enjoyed their birthday traditions.

"One hour, I can spend one hour here before I have to head back."

"In that case then," he said getting to his feet and staggering over to his bar "It's time to get serious."

"I'm not playing any drinking games with you Oliver." She warned as he grabbed a couple of shot glasses and sat back down next to her. Many a night she had held back Lois' hair while she rode the porcelain pony as a result of their games. Chloe knew that she couldn't even keep up with Lois, let alone Ollie.

He poured them both a shot of tequila. "Fine. But you are going to play at least one party game with me."

"It's a big no to the strip poker too."

He rolled his eyes at her "Give me some credit." He knocked back his drink. "I was thinking more along the lines of Truth or Dare."

Chloe laughed. "Now I know you are kidding."

"You're too guarded. And what better way to understand the enigma that is Chloe Sullivan than by drinking tequila and playing children's games?"

Chloe drank her drink. "I'm not really the Truth or Dare type."

"You're telling me that you've never played it? Not even with Lois?" The disbelief was clear in his voice.

She chewed on her bottom lip. It was the favoured game when the cousins spent some quality 'Chlo-Lo' time together. Surely Lois hadn't told him that?

He took her silence as an affirmative. "Come on. What's the worst that can happen?" He asked.

"Well, you've just cursed yourself right there Ollie. Just remember that this was your idea." With a new determination, she planned to make this game as uncomfortable as possible for Oliver so she could not only turn the tables on him but so she could also go home to the relative quiet of her watchtower.

"Great." he poured them another round of drinks. "And being a gentleman I'll go first."

"Okay. Truth or dare?" Chloe asked.

"Truth." He smirked.

Chloe thought for a second. "Alright. Bart, AC and Clark. Shag, Marry or Cliff?"

"Shag, Marry or Cliff? Sounds like you have been watching one too many Austin Powers movies."

"Come on! Out of Bart, AC or Clark who would you marry, sleep with or push over a cliff?" She smiled "Or are you not comfortable enough with your sexuality to answer the question?"

He looked directly into her eyes. "I have no problems with my sexuality." His voice was slightly deeper and it incited a physical response in Chloe that she did not want to admit to.

She swallowed before picking up her drink, giving herself an opportunity to break eye contact. "Forfeiting already?"

"Fine." Oliver knocked back his shot. "I would cliff Clark without question."

"Because you know that he would survive the fall?" Chloe asked.

The look on Oliver's face clearly said that he hadn't thought of that. "You want the other answers?"

"Carry on!" She encouraged while pouring more drinks.

"I'd have sex with Bart because at least I know it would be over with quickly." Chloe laughed out loud before pushing Oliver's drink towards him.

"And I would marry AC because at least he'd spend most of the time in the ocean and not at my home. That and if I had to be married to the other two I would commit suicide within a week. Could you imagine it?"

Chloe caught herself giggling. The alcohol was starting to have an effect on her giving her a pleasant light headed feeling. "I think I should slow down on the tequila. I never giggle."

"Oh no, you're not getting out of this so easily." Oliver said topping up her glass. "Besides, it's your turn. For all you know you'll need the courage. So which is it - truth or dare?"

She had to think about this. She trusted Oliver while sober, but while he was drunk he was a lot less inhibited and could still think of some pretty embarrassing dares. Then again, he could ask a question that he knew under normal circumstances she would never talk about. Chloe knew she shouldn't have agreed to this, there was a reason she only ever played this game with Lois.

"Come on sidekick, don't tell me you're forfeiting already?" He said throwing her own words back at her.

"Fine. Dare."

Chloe swore she saw a mischievous twinkle in his eyes. "Tell you what, I'll start you off easy. I dare you to give me a neck rub."

"Wow. Your imagination really sucks. I'm disappointed." It wasn't a big deal to Chloe. After many a mission she had given neck rubs to all of the JLA at some point, although Bart always tried for more than his fair share.

Oliver slowly began to unbutton his shirt. "Oliver, what are you doing?"

"As our watchtower I should be more concerned about your lack of observational skills."

"You don't need to take your shirt off for me to rub your neck."

He chuckled. "My dare, my birthday, my rules, and I say the shirt has to come off."

"Typical." She muttered as she began to massage him.

"What was that?"

"Have you noticed that whenever there is a member of the opposite sex in the room you always have to be shirtless?"

"You know most women don't complain when they find me without clothes."

"I was just wondering if it was something you did consciously or if you just have an aversion to clothes."

"Hey, I didn't pick truth."

"I didn't ask."

"So you're cheating? That means another turn Sullivan." Oliver said, trying not to enjoy her hands on him too much. "So truth or Dare?"

"I knew I shouldn't have agreed to this." He turned around and stared at her. "Fine! Truth."

"What colour underwear do you have on?"

"Oliver!" She slapped his shoulder.

"So you're forfeiting?"

"Bit of a personal question, don't you think? How is that question going to 'understand the enigma that is Chloe Sullivan'?" She narrowed her eyes at him.

"If it's that big a deal, I'll show you mine first…" He reached for the button on his pants.

"No! Keep your pants on." She waved her arms in front of her "No need for the show."

"You have to answer or as part of the rules you'll have to show yours to me."

She swore he was making up this up as he went along. "It'd be kinda hard to do that. Unless you're willing to make the trip into Smallville."

He thought for a second. "Are you saying..? Wow, who would have thought you were so kinky?"

She rolled her eyes. "There is just no way you can wear these pants without a visible panty line." She couldn't believe she was justifying her wardrobe choices to him. Taking her drink she swallowed it in one "And now I am suitably embarrassed, I believe that is my cue to call a cab."

She stood but he grabbed her hand pulling her back down. "I'm sorry. I promise that I'll take your secret to the grave."

"You do know that what happens in a game of truth or dare is never spoken of again right? Because I swear if you bring this up at the next meeting…"

"Your secret is safe with me." He said throwing an arm around her.

"It better be." She was very aware that a half naked Oliver Queen currently had his arm around her. She would be lying to herself if she said she didn't find him attractive, and yes, the thought of him naked had popped into her mind while she sometimes comforted herself with her own hand at night. But to be so close to his warm body made her heart beat wildly and her hands shake. She collected her drink from the table hoping to take her mind off of her inappropriate thoughts. "So truth or dare Ollie?"

"Dare."

"Give me a foot rub. I've been on my feet all day working for you so this is my reward." She scooted further away on the couch, thankfully giving her an excuse not to be so close to him. She flicked off her heels before plopping them down into his lap. She smiled as he gently picked up one foot and began to massage it. His gentle touches soon had her regretting picking this dare. Every firm caress of his fingers had her thinking thoughts you should never have about your boss.

"Truth or Dare Chloe?"

"Truth."

"It's been months since your divorce from Jimmy came through. Why are you still hiding yourself away from the world?"

"I haven't done it deliberately."

"You're not ready." He stated rather than asked.

"No. If I'm honest…" Chloe wished he had kept up with the sexually inappropriate questioning. She reached over and knocked back her tequila while Oliver continued her massage.

"Carry on." He prompted.

"I'm scared to, alright?" She pulled her feet from his grasp and tucked her legs under herself, curling into a ball.

"What are you afraid of?"

"I'd rather not go into this Oliver. I've answered your question. Please leave it alone." She found these things hard enough to discuss with Lois. Even her cousin hadn't been brave enough to broach this subject yet.

"I think I really know what all this is about. Olsen really did a number on your self esteem didn't he?"

Chloe just glared at him while grabbing another drink.

"Fine, I'll let it go." The look on his face told Chloe that this was not the last she had heard of this. "So give me a dare."

"I dare for you not to bring up my lack of a social life for the rest of this evening."

He grinned. "That was sneaky." She shrugged her shoulders in response.

She had had more than enough of this game. No matter what, this was the last time. She would be grabbing a cab and heading home before this evening became any worse. This game was a lot more fun with Lois, and being around a drunken Oliver for fifteen minutes had really dampened any happy buzz she had.

"Okay, but this is the last one. I really need to get home. Dare me." She wasn't going to give the man any more opportunities to psychoanalyse her. And if that meant singing from his balcony at the top of her lungs or prank calling Clark, so be it.

He looked at her for a while, Chloe swore she could hear the cogs turning. "Kiss me."

Rolling her eyes Chloe leant forward and kissed Oliver on the cheek. "There you go. Now if you don't mind I'm going to head on home."

"Hold on there professor. That was not a kiss." He told her seriously.

"I'm not sure how much you've had to drink Ollie, but that was a kiss."

Oliver scooted next to her on the couch leaving Chloe feeling uncomfortable with the lack of personal space. "This sidekick, is a kiss." Oliver closed the small distance and cupped her face with his hands. Before she could protest he swiftly brushed his lips against hers before teasing her mouth open with his tongue. Chloe's mind was protesting as her body willingly followed Oliver's lead. It had been so long since she was kissed, and even longer since a kiss had left her whole body tingling.

Her eyes were still closed and her mind was still spinning when Oliver eventually pulled away. "See the difference now?" He asked.

Chloe blinked several times trying to gather her thoughts. "This game has taken a turn for the worse. I think it's a good idea for you to get some sleep while I go home." She rose from the couch, slightly unsteady from the amount of alcohol she had consumed.

"Don't go Chloe." He gently grasped her hand, preventing her from walking away.

"You're drunk. I think it's best I go before you do something else you'll regret in the morning. It's your birthday, you're on your own feeling lonely - believe me I get it. I'll keep that little slip between us and I promise you that this will not get back to Lois."

"I don't care if Lois knows."

"Well I care enough for the both of you to know different. I know you still love her Oliver."

Oliver gently rubbed his thumb along the pulse in her wrist, watching her face as he caressed her skin. "Me and Lois haven't been together for a while. As much as I thought it was, it wasn't love. If I truly loved her, I couldn't have walked away like I did. Just like I know that I would never be able to walk away from you."

She narrowed her eyes "This isn't funny Oliver."

"Who's laughing." He got to his feet and took both of her hands in his. "If you want the truth, I've been thinking about you for longer than I should admit to, and I know you are attracted to me."

She shook her head and looked at her feet. The intensity of his gaze was beginning to make her feel uncomfortable. It was if he could see right into her eyes and find all of her thoughts and feelings there. "You're presuming too much. I told you I'm not ready to be feeling anything for another man."

"No. You said you were scared and that is completely different. I just want you to see that there's nothing to be scared about with me. You have so much to offer any guy you're with. I'd like to able to earn that chance with you."

Her head was still fuzzy and this was so surreal she could hardly believe it. She was tempted to pinch her arm to see if she was dreaming. After all of the tequila she had consumed there was a good chance that this was a dream and that somewhere she was passed out on Oliver's couch while he sang happy birthday to himself.

"So I am daring you Chloe. Take a chance with me, I promise you I won't let you down. " For a guy who had drunk at least double what she had he was strangely eloquent.

Chloe looked into his eyes. He was serious and it surprised her. He wasn't wrong when he had said her self esteem was at an all time low, and hadn't she been lamenting about her lack of social life? She trusted Oliver and physical attraction was not a problem. He knew her secrets and she knew his; there would be no need to hide half of her life to prevent him from being hurt because he was already involved. She just needed to take that leap of faith.

"I have another dare for you Ollie. I dare you to kiss me." Oliver gave her his biggest smile before happily obliging.