Warning: Adult content, but probably the bigger warning is the fact this is my first attempt in this particular category, so fingers crossed.

First Time

Feeling Chloe break the kiss to take a much-needed breath, Oliver rested his chin on her forehead. He closed his eyes, not caring what changed her mind, or the range of other emotions she had made him feel over the past hour. All that mattered was that Chloe was wrapped in his arms voluntarily, and doing nothing to back herself away.

Tucking a strand of hair behind her ear, Oliver stared at Chloe with an odd sense of relief. "For a second... I thought I was going to lose you again."

Chloe pursed her lips momentarily, knowing everything she must have put him through, but as she found her words, she was also reminded of something else Oliver said. "I thought you weren't going to give up on me."

"Never will," Oliver replied almost immediately, figuring that point was coming up, "I'm just glad you came back."

With a smile escaping her lips, Chloe leaned up and whispered, "Me too."

From there, Oliver enclosed the space between them, relishing this feeling as long as he could. Even though he was practically groping her with his hands, Chloe showed no insecurities towards his advances, so Oliver continued to kiss her, knowing she wasn't going anywhere.

But then he felt a twinge of guilt. He was more than aware of her romantic past and even though he wanted nothing more than to sweep her up into his arms and carry her away, he didn't want to overstep, especially not now.

Noticing the flicker of worry in his eyes, Chloe brought her hand up to rest on his cheek. "Something wrong?"

His hand still lingering in her hair, Oliver found himself retracting slightly. "It's just that...I don't want to push you." As he stutter-stepped back, Oliver felt Chloe's grip around his waist tighten, so he looked back at her, watching her take in a breath before finding his eyes in her stare.

Sure, part of her was scared, but the same time, Chloe knew that if she'd walk away right now, she'd just run back to him. And as much as what was happening scared her, not ever letting it happening scared her more. "I don't think I can be more ready for this... just... bear with me."

"I'll go slow, I'll –"

His words were cut off as Chloe's finger went over his mouth. "I don't want this to be a big deal."

Oliver narrowed his eyes as he brought his head closer. "It kind of is."

"Then show me... by acting naturally."

This time, she closed the distance in order to kiss him, because she didn't want to talk anymore. Talking usually meant that Chloe would find a way out and she wanted Oliver too much to make up an excuse for herself. Even the inch he had created when he stepped back created more space between them than what Chloe wanted.

They had spent enough time apart, putting wedges between each other, even pushing the other away, that this closeness felt long overdue, and with each touch, she felt herself further melting into his arms. Even the way she felt his hair skim past the skin of her cheek sparked something within her, not to mention the real reason he was there.

It was no secret he was essentially marking his territory, but Chloe did nothing to stop it, nor did she stop Oliver from taking off her jacket. After the muffled thud it made on the floor, Chloe felt her breath hitch at the feeling of Oliver's hands on her bare skin as he slipped them under her shirt. Her chest muscles further clenched as he worked up her body, but seconds from the lining of her bra, he moved his hands behind her back, pulling her closer.

Unfortunately, that movement caused Chloe's neck to be strained further, one of the consequences of their height difference. But once their lips met again, she wasn't about ready to let it stop, so Chloe desperately lifted her leg to get her an extra inch or two, but Oliver took over, cupping his hands under her ass, lifting her up in the air.

She understandingly yelped, as she hadn't been anticipating that manoeuvre, but she reacted appropriately, wrapping her legs around his waist as Oliver helped her regain her balance. But it was then that Chloe realized that she had no idea what to expect because she wasn't exactly an expert in this category. Heck, she couldn't even call herself an amateur. Yet here she was, with a guy who knew it all, and she had nothing, she knew absolutely nothing.

Backing away, she tried to maintain a decent poker face, but Oliver saw right through it, so he leaned his forehead against hers and through his panting, whispered, "Trust me."

Two words. They were simple, short, and in a way, a cliché, but in that moment, all she needed. "Always," she replied, and upon seeing the smile that lit up his face, it was like all of her worries flew away, and all that was left was them.

In fact, she was so caught up in him that she never realized the distance they travelled as she noticed Oliver was letting her go. The soft mattress set in the reality of the moment, they were really doing this. Chloe's eyes momentarily looked back at the pillows to be sure, an action Oliver had misunderstood for a waver in her confidence.

"We don't have to do this."

"No, we don't have to," Chloe replied staring at his still-clothed chest, only to wrap an arm around his back as Oliver was about to stand back up. Meeting his eyes, she said slowly, "But I want to."

Message more than received, Oliver met her lips again, pushing her back slowly on the bed, him atop of her. When they were both firmly on, his hands found the base of her shirt, and he broke the kiss looking for a final sign of hesitance, only there wasn't any to be found.

Within seconds, he had taken care of the buttons of her shirt, throwing it across the room before looking back at her. Chloe was normally terrified about her body, knowing it wasn't toned like Lois's or Evie's, nor was it skinny like Lana's, but Oliver had always made her feel sexy, so she had no concerns, no seconds thoughts as his eyes trailed her almost-naked upper body, admiring her god-given curves.

"Your turn," Chloe whispered, ready to finally have that shirt off his body, but it appeared her words weren't completely true.

As she leaned forward to trail her fingers under the shirt, Oliver had snuck his fingers under her bra and undone the clasp. Giving him a playful glare as she shook the straps down her shoulders, Chloe watched as his eyes found her breasts, distracting him as she flipped her hands over to drag her nails up and down his chest.

"Geez Chloe," he hissed out, leaning his head back, so Chloe took the opportunity to lift the shirt. Half-way up, Oliver caught on and took over, tossing it behind him, which allowed for enough distance between him and Chloe for her to truly have her turn.

She bit her lip hard, because even though she knew how in-shape he was, seeing his muscles up close like this, ignoring the scratch marks she had left behind, almostrendered her thoughtless. There was one word that crossed her mind.

Damn.

Looking back up, Chloe took notice of Oliver's grin, and not wanting to completely give in to him, she just quirked an eyebrow, which only resulted in him letting out a silent chuckle.

He took her mouth once more, but it was short-lived as he left it, tongue grazing down her chin, her neck, settling in-between her breasts. Initially, it felt like a twisted game of eeny-meeny-miny-mo as it swept from side to side, causing Chloe to take matters into her own hands, grabbing Oliver's head and settling it over her right breast.

From there, it didn't matter what he touched nor how he touched it, as there was almost a disconnect between conscious thought and Chloe, as moans or cries were the only sounds to come from her lips, which Oliver seemed to enjoy as he took his time pleasuring her. Gasping as his teeth played with her nipple, Chloe arched her back hard, bringing her high enough that she momentarily felt his hardness through his pants.

"I want..." she managed, wanting him inside of her, but unable to actually complete the thought. However, it was enough for Oliver to end the foreplay with her breasts, as he gave her a quick smirk before popping open the button of her jeans.

Sliding them slowly down her legs, he quickly threw them aside as he took in the spectacle of her body before him. But he quickly moved on, as his hands seemed to work every muscle of her lower body, starting with her toes, then as he worked her legs apart, he massaged them, listening to the short giggle as he tickled behind her knee.

Finally, he noticed the short gasp as he worked his way further up her thighs, her pleasure becoming more apparent as he felt her wet panties between his fingers, the tips playing with her clit. She bucked her hips unconsciously, wanting more from him, but Oliver insisted on teasing her further.

"Oliver... please..." she managed, barely holding her control before he straightened a finger into her. She cried out when he added a finger, working them up and down inside of her, loosening her up, only to bring a whimper from Chloe when he withdrew them and soon felt her panties ripped from her in a single motion.

She watched him lick his fingers, moan at the delight of her taste, but he wasn't about to deprive her either. Coming back down on her, his lips found her mouth again, so Chloe wrapped her arms around his head, nails gripping into him as Oliver pulled her up to a sitting position, her nipples digging into his chest.

Oliver inched his head away enough to part their lips, but only to say, "You're so beautiful," before he claimed them again. He pushed her closer, and Chloe could sense his erection on her again and she felt her hips working, her body wanting more.

Seconds later, she felt him leave her lips again, this time to back away further, but after a considerable amount of time had ticked by, Chloe opened her eyes, confused at the sudden draft she felt against her body in comparison to the heat she had grown accustomed to. Initially, she figured he was second-guessing her again, but when noticed his hand pulling a familiar foil package from his bedside drawer... she knew that wasn't the case.

"Hold on," she said, suddenly feeling a surge of confidence throughout her that pushed Chloe to lean in his direction, snatching the condom from his hands. "Allow me."

As she returned to her sitting position, waiting for him, Oliver stood up to simultaneously shrug off his pants and boxers before turning around to face her again.

Holy... crap, was her first thought. Even thought it was no secret that Oliver was comfortable with his body, it didn't stop Chloe from taking another appreciative glance.

"See something you like?" he teased her once more.

"Maybe," Chloe replied, her real answer lying as her tongue swept her bottom lip, "but I'll never tell."

"Famous last words, Sullivan," was all Oliver said before he was back on the bed, pushing her back against the mattress and holding her close to him again as they laughed. For a second, they stayed there, bare in front of each other, unable to stare anywhere else as green eyes met brown. Chloe noticed the smile that broke out of Oliver and after taking a breath, she smiled back.

But after a moment's hesitation, she surprised Oliver as she grabbed a hold of him, stroking his length with both her hands, watching as his head titled back, murmuring her name. Chloe had to admit, she enjoyed the moment of control, the way he seemed to be putty in her hands for once.

"You keep that up... I may not make it."

"If you insist," Chloe said, blindly searching for the package she had dropped on the sheets, but upon finding it, she ripped it open and slowly slid the condom on, in her mind, making up for the ecstatic torture he had put her through only seconds earlier.

Only it appeared it wasn't over for Chloe, not by a long-shot. His hands continued worked her body, prepping her for what was to come, but Oliver could sense that her patience was running thin, not that he could blame her.

So he manoeuvred to a kneeling position, carefully adjusting her legs so he was straddling her, but never once did his stare leave her eyes. He knew she was ready, but she was just so damned beautiful that he didn't care about looking anywhere else. Chloe, meanwhile, felt a smile come across her face again as he continued to stare, and that seemed to get him back on track.

She noticed Oliver shift his position slightly and with that, his cock grazed her thighs, causes her to plead with him once more. It had been a long wait, everything had been such a long wait that she just wanted him to be inside of her.

This time, the wait wasn't long. Instead of sliding slowly into her, Oliver sensed her impatience, and well, she wanted him to act naturally, so he thrust hard inside of her, listening to Chloe cry out in response.

Feeling her back leave the comfort of the mattress, she was surprised at the sound of her own voice as she worked her hips with Oliver inside of her, feeling a hint of satisfaction as he delivered his own reaction. He pulled back slightly and Chloe whined, not wanting him to pull out completely, but Oliver quickly pushed back, hearing his name slipping from her lips soon after. She was tight, which wasn't a shock to either party, but she almost seemed to fit Oliver perfectly, a fact that seemed to apply to them, no matter what.

Sensing an opportunity, Oliver snuck his arms around her back, and pulled her closer and took her lips again, but pulled back quickly to lay her back down when he saw something in her eyes. He wasn't sure what it was, so he kissed her again, hoping it would loosen her lips per say, and sure enough, it was Chloe who backed away and momentarily stopped his progress.

Bringing a hand up to his cheek, Chloe opened her mouth, but only managed to say, "I..."

Chloe wanted to say the other words, but between the lack of control she held in her breathing and the feeling of Oliver inside of her, she couldn't say anything.

But that was all she had to say, as "I know," was Oliver's response, warming her heart along with the rest of her body, and with another thrust, she felt herself come, her back soon relaxing back on the sheets.

It didn't take Oliver long to follow suit, leaning his head down as he watched Chloe's reaction. It was true that Oliver Queen had been in bed with many women, but there was something different about this time. For once, he loved the women he was sharing his body with, and it brought a form of satisfaction that he hadn't felt before, and hearing the way Chloe responded to him only turned him on further.

After shifting inside of her unconsciously, Oliver heard a different noise come from her, so he stopped to find her eyes. It was then Oliver saw how hard Chloe was fighting to keep them open, but it looked like it was becoming a losing battle. Pulling himself fully out of her, Oliver heard a muffled moan from her, but he didn't give in, knowing she hadn't been sleeping recently.

Lying down next to her, he turned Chloe so her back faced his chest, a quiet hum escaping as Oliver slipped an arm both under her neck and around her waist.

"Sorry," she said honestly, "my stamina isn't exactly up to par yet."

"Don't care," Oliver replied, kissing her cheek before pushing her closer to him.

Reaching up, Chloe grabbed his hand in both of hers, squeezing it tightly as she closed her eyes. Everything, it felt right, and for that reason, she knew she had to say it in its entirety, even if Oliver already knew it. Turning her head as much as she could in her position, Chloe looked for his eyes in the dark, knowing that she wanted to say this to his face.

When she found Oliver staring at her, she finally whispered, "For the record... I love you Ollie, so much."

Kissing her one last time, he whispered back, "I know, I love you too."

With that, Chloe placed her head back on her pillow, sneaking a smile as she closed her eyes, allowing herself to sleep for the first time in plenty of nights.

~End~