This one-shot as well as 9 others will be based on these mini-headcanons. Thank you seacoloredeyes (on Tumblr) for that wonderful ask - as a result they are all dedicated to you ;-)
1. who wakes the other one up with kisses: Oliver wakes Felicity up with kisses because that's the only way she deserves to be awakened (in Oliver's opinion)
Oliver laid awake in his bed.
It's the wee hours of the night where everyone is sleeping. Everyone save for him. He used to dread that part of his day. It's not that he didn't need the rest - because boy, did he! - he simply couldn't fall asleep. Some nights he just tossed and turned for hours - usually when he'd had a bad Arrow-related day, while others he consciously prevented himself from falling asleep for fear of revisiting his night terrors. He'd much rather pass out from pure exhaustion rather than relive his father's death, Yao Fei and Shado's demises, the Slade debacle, Tommy's death and the years away from home, in his dreams.
His daily routine was so busy that it rarely left him time to think - which is just the way he liked it. QC job from nine to five (sometimes seven if things weren't going well), a quick stop at Big Belly Burger for burgers and a much needed coffee, and then it was time to don the green hood and get out to the streets. On a good night they were done by 1AM, on a bad one it could stretch till 4.
Oliver dreaded those few hours of "free time" between his two "jobs". There was very little he could do to fill his time, being as tired as he usually was. That left him with time to think, remember and regret.
But then, one day, Felicity Smoak happened.
She came crashing into his life and little by little as the years progressed and they got closer, she chipped at his walls, unknowingly to either of them, until her existence was embedded into Oliver's heart.
He couldn't tell you the exact moment when he realized that Felicity was more than just his friend. It wasn't some big moment or a near death experience that made him open his eyes. They were both in perfect physical condition. The tensions between them weren't high - with the years he'd learned to pick his battles with her - a fact Digg was very happy with.
It had been a normal day - or as normal as the days of Team Arrow get (yes he'd caved on that one) - they were both in his office at Verdant. Felicity was updating the security systems and he'd brought some lunch from that little bistro he knew she loved but didn't have time to frequent. They were eating and talking about something insignificant when Oliver felt the urge to lean over the leather armchair she was sitting on and kiss her. But that hadn't been the first time that urge rose within him. Oliver had learned to push those particular desires aside with time - especially in the early days of their relationship where he still believed he had a choice in the matter.
Yet when he'd looked at her wave her hands animatedly at whatever it was she'd been talking about he realized that there was no choice to make. This brilliant woman had managed to worm herself into every aspect of his life to such extent where Oliver couldn't fathom the idea of her one day not being by his side. This, coupled with the desire to kiss her, made him realize that his life was filled with enough regrets already - he didn't want her to be another one.
So he'd kissed her.
Since then he no longer dreaded the nights between his Arrow job and CEO job. They didn't even have to do anything. He was perfectly content to just hold her as they - more often just she - slept.
Even in this very moment, despite being tired by both of his jobs and his and Felicity's "extra curricular activities", his entire focus was on the way her chest moved when she breathed, or how her legs were entwined with his own - making it difficult to see where one begun and the other ended, or how her hair was sprawled against his chest, or how her eyes fluttered slightly behind her eye lids. He knew she was a vivid dreamer - and he was also curious to know what she was dreaming about. The endless possibilities of Felicity's dreams could entertain him for hours on some nights.
Some nights he still had trouble believing that she was with him; on certain nights, especially ones that ended on a good note, he was still afraid that maybe he'd dreamed it all up - that it was just in his head, just a dream; on bad nights,he failed to see what she saw in him, but fact remains that Oliver is a selfish being - especially when it came to Felicity - so letting her go was not an option he was willing to consider.
Gazing at her now as she slept in his arms, Oliver was once again swept by the strong desire to kiss her. Rationally, he knew he should let her sleep and that by waking her he risked having the digital alarm clock to be aimed at his head for interrupting her rest (again), but like previously stated Oliver was selfish.
He was never good with resisting temptation and he had not an ounce of resistance - or a desire for it - when it came to Felicity. So he swept the few locks of hair away from her face.
The first place his lips touched was the top of her head, then he slowly traveled down to her forehead, breathing in the scent of her shampoo as he did. He trailed kisses over the right (and visible) side of her face. Slow, unhurried, gentle pecks that trailed down to her temple, over her eyelid and all over her cute nose.
Felicity shifted next to him then and Oliver knew that she was a blink away - no pun intended - from waking up, yet he couldn't bring himself to stop. He moved to her soft cheek and then down towards her chin.
"Mmm," Felicity's soft, still sleepy, moan of appreciation let him know that she was awake.
"Mornin'?" she mumbled, burying her face into his chest.
"No," he whispered just as softly between kisses that he now peppered her shoulder with.
"I love you," he told her quietly.
That got her to open her eyes a little and the smile she gave him filled him with a sense of contentment and peace that only she could give him.
"Lov'uo too," Felicity breathed before her eyes closed shut on their own accord again.
"Sweet dreams." Oliver pressed one last kiss against her head.
Tightening his hold on her, Oliver decided to give sleep another try.
Imagine his surprise when the next time he opened his eyes his vision was filled with a happy Felicity pressing kisses against his face, with her blond hair surrounding them, and wishing him and good almost-noon (because they've apparently slept through the morning).