A/N: This is one of three GG oneshots I had written (one has already been posted, so this is the second). The oneshots I've been writing lately, they're not sitting right with me. I don't know what it is, but they haven't been up to my usual standard. At least I think so. Anyway, maybe they're a little OOC, just a little. I don't know. These aren't my favorite works by far. This would technically qualify as a future fic not that it matters that much. Well, enjoy. R&R. Thanks. –Mac

Disclaimer: I don't own Gossip Girl, but oh to have one of those boys as my own personal slave…lol.

Once More Won't Hurt

Every time, it was just once more. For it couldn't hurt. The damage was already done; one last time wouldn't change anything. But even as they swore there would be no next time—there always was. Fool's logic, an objective party would say, but in this case there was no objective party to bring them to their senses. There was just them and even when they said they wanted no more, they couldn't get enough.

They blamed the other for turning up at their door, they blamed fate for causing them both to be in the same coffee shop at the same time, they blamed their friends for throwing a party they would both attend and get overly intoxicated at—all situations which would lead them to falling into bed with each other one last time. They would never admit to themselves or each other that maybe they didn't want it to be the last time; maybe they wanted it to be the first time. They weren't built for that though, not for each other anyway.

He would never say he hated the way she could flit back and forth between him and his best friend so easily. She would never say she wished he didn't feel the need to indulge in the hordes of women of the morally lax variety. Instead they remained silent on the matter, never deterring from the system they had established. They let those feelings sit and eat away at them—always remaining unspoken. They could live with it, they told themselves. Besides a person wasn't truly an Upper East Sider until they made a sacrifice for the sake of appearances that systematically corroded their hearts away.

They would uphold the roles they filled in their society—her as the morally virtuous Queen Bee, and he as the embodiment of hedonism and sin. And when it suited their purposes they would come together and just be Blair and Chuck. No titles, no parts to play, just them for the one last that never seemed to stick.

"You and Nathaniel on the outs again?" Chuck asked the question even though he already knew the answer. She only came to him when what Nate offered her became inadequate—which was happening increasingly more frequently. He couldn't count the times the Archibald-Waldorf engagement had been called off.

"Yes." Blair answered simply, sipping at the drink Chuck had offered her at her entrance to his suite. Chuck wasn't sure if she would elaborate further or not—sometimes she did, sometimes she didn't. It looked as if she wasn't going to, but after a few moments of hesitation she continued. "You should see the woman he hired as his assistant. All bottle blonde and long legs. He's started to work late, he's never worked late. It didn't start until he hired her."

Chuck frowned, "Do you believe he is cheating on you?"

"It's a possibility, was a possibility. It was clear he was keeping something from me. I couldn't stay if he wasn't going to be honest with me." Blair responded. "I gave him back the ring."

"That you did." Chuck nodded, taking in her bare ring finger.

"So Chuck, how have you been lately? I haven't seen you since my mother's Christmas party."

That's how it had been since they had all graduated from college. Before, the two met more frequently—in both private and public meetings. It was easier for them to be seen together, even when they had their own respective counterparts. Now that they had their own lives, careers and etcetera, they didn't see each other much outside of their little rendezvous. For the first time in their lives they weren't running in the exact same circles, there was of course some overlap and they happened to see each other at some event, some party. It just wasn't as often—neither would ever say that they wished it was different, that they could see each other more often.

"I've been wonderful. And you, Blair?" Chuck replied in their usual fashion. He could have told her the truth, but they didn't have that kind of relationship. Somehow, Chuck believed that Blair knew the real answer to that question. And she did, she would never acknowledge it though.

"Besides Nate's infidelity, I've been marvelous. My father and Roman will be coming into town in a couple weeks, so I'm making preparations for that. I'm doing well."

"I'm glad." Chuck said. He reached out to touch her cheek gently, drawing her toward him. They were done with idle small talk, it was time to start what she had really come for.

Their lips met softly at first, but it soon turned into an urgent, passionate kiss. Chuck stood from his bar seat and pulled Blair up with him. One hand found her hair, the other her waist. Blair pressed closer to him and they began to move toward his bed. After a few moments stumbling around furniture they reached the foot of the bed. Chuck picked Blair up and placed her on the bed. She crawled backward and he followed.

As he lowered himself on top of her, she looked him in the eyes, "This is the last time."

His only response was to kiss her deeply.

- - - -

Less than a week later, Nate apologized for any suspicions Blair might have been led to believe. He fired the leggy blonde and convinced Blair to take him back. Within a day or so from then, Blair had the Vanderbilt ring in its rightful place: on her finger.

The day it was announced that the engagement was back on, Chuck drowned himself in scotch and took the first willing, attractive woman he found into his bed. Something he repeated nightly for a good two weeks. He knew he should be used to the cycle by now, but it seemed that instead of getting better, it only hurt more each time she returned to Nate. It was never a good feeling, being second. Inadequacy did not bode well Chuck Bass, but there was nothing he could do.

- - - -

The next time Blair appeared in Chuck's doorway, he didn't hesitate to let her in. On a normal day, Blair never left the house looking anything less than perfect. That day, apparently, wasn't a normal day. As she shuffled past him into the room, Chuck took in the tears streaming down her face, how her hair was no longer neatly in place, and how her cheeks were tinged pink most likely from the cold. He couldn't help but feel instantly worried.

"What happened?"

"I walked here."

Chuck took a deep breath, "That's not what I meant."

At the genuine concern in his voice, something broke in Blair and everything came tumbling out at once, "All those times, all those times I thought he was cheating, I never believed that he was. I just said it because it was my way of excusing all the little problems that were tearing us apart. I never though, I didn't think he could, not again. They had started to spend more time together, but I never thought anything of it. I thought anything of it. I thought he had gotten over his silly infatuation back in high school. I never thought she would ever, not with Dan this far away from proposing."

"Serena." Chuck responded, gathering a conclusion from the mad rush of information.

"I went to his office to surprise him for lunch. I thought he would appreciate it considering we were just getting back on track." Blair offered a weak smile, "I guess the real surprise was for me, hmm?"

"Blair, I'm sorry."

"No. Don't apologize for him. That's not what I came for. You know that's not what I came for." Blair met his eyes and held his gaze as she stepped toward him. "Chuck, you know. Once more won't hurt."

Chuck nodded and, taking that as permission Blair closed the distance between them and brought her lips to his. His hands came up to her face to wipe away what remained of her tears. The kiss remained gentle, soothing, as they moved toward the bed for the countless time. Her hands clutched at his shoulders as if she was holding on for dear life.

Then it changed, the heat seeping its way in and consuming them. The clothes were shed and they found themselves under the covers. Afterward, Blair was curled in the crook of Chuck's arm. He was absentmindedly playing with one of her curls when she spoke.

"I want this to be the last time," Blair whispered, and Chuck's heart sank at the genuine finality in her voice. But then she continued, "that I have to leave. Because the next time I come here, I want to stay. I want to stay with you."

"Blair, you don't mean…"

"We've been fools, the two of us. I know, and so do you, that what we've been doing isn't what we really want." Blair said, "Nate doesn't know that I know about him and Serena, he didn't see me come in. When I leave, I am going to end things with him, for good. Then maybe we could…"

Chuck smiled, "We could?"

"Try this once more, for real without Nat and all those girls you parade through here." Blair finished, looking hopeful.

Chuck kissed her lightly, "Once more won't hurt."