A/N: This happens between Season 1 and 2, while Roy was infiltrated in the League of Shadows. And it's kind of based on Red Arrow's journals.
He had been undercover, working for the Shadows for a while now. Roy never really understood why Cheshire helped him join the Shadows and he was most certain she suspected he might be an infiltrated, but the truth was he never really understood most of her actions anyway.
She was always close. Too close. She already knew his identity, his problems with the League… He didn't want to tell her anything, he didn't even want her close, but for some reason she always managed to get what she wanted. And of course, she always flirting with him. That was also a problem, for he didn't know whether she was just playing with him or if she would ever try something more. And even though he always told himself he would never allowed himself to do anything – not only they worked together now, but also she was a supervillain –, a part of him was afraid he wouldn't be able to stop her. To be fair, to stop himself. Luckily, they were often really busy. So his mind would be occupied, which helped him ignore her.
They were in a mission in the Middle East that time, only the two of them. They were told to would be something simple, just to chaperon an important shipment to this small city in the middle of nowhere. However, when they got there, things got more complicated. Many looters. A big fight. And they were alone. In the end, Cheshire had to take down most of the guys alone, so Roy could deliver the shipment safely. It was hard, but they had done it.
Later that night they went to a small abandoned apartment they would crash at until morning. Roy felt frustrated. He thought something about Speedy would come up this time, but again he found nothing. He felt cursed. He thought joining the Shadows would make things easier, but he was getting nowhere. Literally. He looked at the place he was with disdain. If things weren't bad enough, he would have to spend the night with Jade. Oh yeah, he called her by her real name now.
It wasn't the first time they traveled together in a situation like this. But the more time he spent around her, the more complicated things get. He knew stuff about her now, how she raised, how she felt about her father… And she knew… Well, he wasn't sure what she knew, but sometimes he caught himself talking to her about his frustration with the League and how it felt to be brainwashed. He never knew whether she felt guilty about being part of it or not, it was hard to read her. But she always listened.
His train of thoughts was interrupted when he heard the woman groaned. The room was dark, so it took him a few seconds to find her. When he finally was able to see her, he almost gapped. She was untying her green kimono. He frowned, very confused, he knew Jade didn't have boundaries or anything, but he never thought she would simply take her clothes off and- Oh. Suddenly he realized what she was doing. A cut. Quite deep. On her left side.
She groaned again, walking near the window, where the moonlight was enlightening the room a bit more, so she could look better at the injure. "Bastards…" She mumbled.
Roy found himself approaching her carefully. "Are you hurt?" He asked straightly, suddenly feeling anxious for some reason he wasn't sure why.
She lifted her head to look up at him, who was now a few inches of distance. Jade smirked amusingly. "Careful, lover-boy, or I will think you actually care about me." She said in a teasing voice, as she tied her kimono up again.
Roy held her arm quickly, stopping her. He saw her eyes widened in surprise. "I'm serious, Chesh. I saw the blood." He hated how he was already used to call her by that stupid alias nickname.
Jade smirked again. "Don't worry, Red. It's just a scratch. I have had worse than that. Believe me."
"I think I have an aid kit here somewhere here…" He commented, ignoring her, and turning around to look for the kit inside the stuff they had left on the apartment's floor.
"Seriously, Roy? You, playing the caring gentle guy?" She joked, crossing her arms.
"This is my fault. You should have delivered the shipment and I should have taken care of those bastards." He said, sounding angrier than he expected.
For some reason knowing she was hurt let him madder than he already was.
"Oh sure…" When he turned around, he gapped. She was in front of him, one of her swords was pointed to his throat and the other to his stomach. Her eyes fiercely on him, that grin on lips. "Because you are so much better than me…"
Roy groaned impatiently, why does everything have to be fight with her? "That's not what I meant, Jade." He said, pushing her arms down carefully.
She took a step closer, looking at him carefully. He hated when she did that. It always seemed she was trying to read his mind, it always seemed she knew something about him not even he himself knew. But she was probably just playing with him again, which seemed to give her some kind of twisted pleasure. And for some reason, he never really stopped her.
"Then what did you mean?" Jade asked.
Roy thought about her question for a while. What did he actually mean? Was he actually concerned about her? She was one of the most dangerous people in the world, she knew how to take care of herself… Better than him, for sure. Why would he even care if she was hurt or not? He made an effort to push these thoughts away. The last thing he wanted now was to self-psychoanalyze his own actions. All he wanted now was to make sure she would be okay. Because he might need a backup later, of course.
"Come," He finally spoke, pulling her by the arm and completely ignoring her question. "You're bleeding."
Roy sat her on the dusty bed in the center of the room. He thought she would protest or at least make a comment teasing him, but she didn't do anything but observe him. If he didn't know her, he would say she felt awkward. He opened her clothes a little again, just to reveal the wound, and started cleaning it. She was right, it wasn't that bad. And suddenly he felt really stupid.
He was taking care of her? As though she was… something to him, and not the psychopath who help the people who brainwashed him. He didn't stop what he was doing though. And she sat there still and quiet.
For some reason, the constant turmoil inside his mind got better when he was near to her. Probably because other kind of thoughts took over his mind. Thoughts he mostly certainly shouldn't have about an enemy. They might have been working together but she was still an enemy.
He felt his hands sweating, as he finished bandaging the cut and finally looked at her face again. His heart was pounding hard against his chest. And he hated himself for that. It was as if he was still being controlled by someone. And worst was, a part of him enjoyed it. That's why he couldn't simply ignore her. Roy swallowed hard, noticing her inquisitive eyes on him. She remained in silence, just staring at him for a few of seconds, and he felt even more tensed.
When he was finally starting to move away from her, she spoke, "So aren't you going to explain me?"
"What?" He tried to sound causal.
She stood up and started walking around him, gracefully. She often reminded him of a cat.
"That." She raised one eyebrow. "I know you like to play the hero. But we aren't exactly friends, are we?"
"I just wanted to help, Chesh, let it be." He groaned, impatiently.
"But why? I mean, obviously you like my company…" She teased him, smirking. "But you aren't here only because you like me… not even because of the money, right? So, you don't need to be nice to me…"
Again. She was playing with him. She only wanted to get under his skin. God, he hated that woman.
"No!" He shouted. "I don't know what you are talking about. I was just returning a favor. After all, I wouldn't have this job if it wasn't for you." He paused for moment, and then he stepped closer to her. "Now, why did you do that? Why did help me get into the League of Shadows anyway? I mean, besides the obvious delight you take by torturing me."
Cheshire laughed and got even closer, her eyes going from his eyes to his lips. He didn't step back though.
"You have your secrets. I have mines. Also, you should be thanking me."
"So should you."
"Fine…" She smiled and leaned in, giving him a quick kiss.
"Wait." He grabbed her by the arm, staring at her. That was what he hated the most about her. Something loosened inside him every time she did something like this. His focus, his goals, his obsession… It all faded away. All that lasted was his angriness and that stupid desire.
He saw her hand going to her swords, as always she was ready for a fight. But he was sick of fighting. For now. He leaned in and kissed her again. He wasn't sure why, a strange urge made him do it. And now that he did it, he wanted more.
He realized he shocked her, but he didn't care. She had kissed him without permission before. He kissed her deeper, losing control completely. Why did he always lose control around her anyway?
Maybe if he did that this one time, this strange need would go away and he would be able to ignore her once for all. He heard her gasping when he pushed her against the wall, kissing her neck.
"Roy?" She asked in a whisper, sounding out of breath.
"Hm?" He looked at her impatiently. His eyes directly on her, both of them were without masks now.
"You know that's a very stupid decision, right?"
Roy swallowed. She was right. Whatever that was, it wouldn't go away. It was just going to get worse. And it was probably going to be his doom.
He felt her breathe against his face, and her eyes impatiently demanding an answer or a reaction.
What the hell. He was doomed anyway.
"Yeah…" He mumbled as he kissed her and leaded her to bed.