A small groan fell from her lips as she woke. Her head was pounding and trying to wrap around what was going on was not helping her migraine. Forcing her eyes to open, she winced slightly at the sudden invasion of light; blinking rapidly a few times, the blonde managed to open them completely and glance about the room. It was a large office, intricately decorated, simply screaming money. As her blue eyes flickered about the room, the girl suddenly caught sight of a body beside her, a sleeping body, and a very naked body.

Jenny's eyes widened as she realized that it was Chuck Bass lying beside her, snoozing away in his birthday suit. Had it been any other situation, she may have stopped and taken into account the sight of the sleeping boy billionaire; he was so peaceful that it was hard to believe that it was him, especially after everything that had been going on in his life lately. But this was hardly any moment to do such a thing.

Reaching up to tuck a loose strand of hair behind her ear, she noticed that a blue sleeve hung around her arm. Jenny knew that she hadn't been wearing that color not to mention, she didn't wear things that hung so loosely on her body. Further examination told her that it wasn't her shirt, but it was the only thing she was wearing. Her eyes glanced once more towards Chuck and the realization hit her.

Once more her hand went over to her face, but this time it was to push all of the hair away from her face. This seriously couldn't be happening. No. This wasn't right. How did she even get here? The last thing she remembered was going to a brunch for this boy beside her with Eric. And then that Gossip Girl blast about her father and Lily van der Woodsen. She had gone to speak to her brother, but had been intercepted by Blair, asking her if she had seen Chuck. Of course Jenny hadn't, but she promised Blair that she would help and she had started looking around only to hear a gaggle of giggling girls and so she followed it, only to find them in what she presumed had once been Bart Bass' office and one of the girl's in the middle of stepping out of her dress. After that, she really couldn't remember what happened.

As the blonde struggled to remember the details, she choked on a sob; Jenny Humphrey had lost her virginity to Chuck Bass and she couldn't even remember it. She needed to get out of there; she needed to get away from him. Quickly getting up she searched around the room for her things; her dress was bunched on the floor halfway beneath the desk, and her shoes were on two different sides of the room, and she didn't even bother searching for her undergarments. Heading out of the room, the tears started to fall down her cheeks so she didn't realize that she was about to crash headfirst into someone. And the minute she did so, a pair of strong arms reached out and caught her before she could hit the ground.

"Woah, woah," a deep voice said, "normally I wouldn't ask why a beautiful girl was rushing towards me half naked, but when she's crying…"

"I'm s-sorry," Jenny blubbering, wiping furiously at her cheeks, "I j-just…need to…"

She couldn't finish speaking; her cheeks were glowing with bright red embarrassment at being caught in her current predicament.

"Don't apologize," the man said gently, "let's just get you cleaned up before you rush off to wherever you were headed."

He took a light grip on her arm and lead her bathroom where he grabbed some of the complimentary towels (it was Bass Inc. after all) and handed them to her.

"I'm such a mess," Jenny groaned as she accepted the towel and started to wipe at the run of mascara and eyeliner down her cheeks.

"Eh, it's not too bad," he said as started to straighten out her dress for her.

Jenny shot him a look a he chuckled, "I'm Jack by the way," he said handing over her dress and turning his back so that she could have a bit of privacy.

"Jenny," she said back as she peeled out of Chuck's shirt as quickly as she could and pull the dress on from yesterday.

There was a slight pause before Jack decided to speak again, "you mind telling me what a girl like you is doing here so early in the morning and crying?"

The blonde paused as she slipped one shoe on after another, "that's the thing," she said quietly, almost as if she was embarrassed by her answer, "I can't remember."

He looked over his shoulder at her, and then turned around completely, seeing that she was fully dressed, "well I'm sorry about whatever it is. Now…why don't we see about getting you a cab home Jenny?"

Jenny offered him a small smile and nodded as he led the way out of the bathroom, but just as he stepped outside the door, Chuck came out of the office and upon seeing his Uncle walked over.

"Hey Jack," he said, looking rather ragged in his slacks and just the coat from the day before, "have you seen any girl's coming out of here? There was this amazing girl from last night, but for the life of me, I can't remember her face…we were too deep in party favors."

Jenny, hearing his voice had slinked back into the bathroom, not wanting to leave. Jack had looked over his shoulder at her for a split second and realized exactly what happened, and decided to do his bit of charity for the day.

"And by any chance have you seen my shirt," Chuck asked.

"Look, Charles," Jack said, ignoring his last question, "you're my nephew, and I wouldn't be looking out for your best interests if I didn't tell you that this girl is the last thing you need to be worrying out right now. You really screwed things up last night with the members of the Board when you didn't show up to the brunch yesterday. So, I suggest you decide to mend that bridge before gallivanting after some girl that ran out on you."

For a moment there was silence and Chuck nodded slowly, "right; well if you see any girl coming back looking for these," he said, holding up a pair of pink lace panties, "do me a favor and get her name," another pause as he fished something out of his pants pocket, "and this; I know how much she enjoyed it last night."

That seemed to be the end of the conversation because Chuck stalked away and Jack watched after him before he turned and looked at Jenny. He looked down at the thing his nephew had handed him for a moment before walking over to her, "here," he said, handing her the little vial of cocaine out to her, "make of that what you will. …I'll have a cab waiting for you out front when you're ready."

Jenny nodded halfheartedly as she looked down at the small vile filled with white powder inside of it. How much she enjoyed it last night? What did he mean by that? Is this why she couldn't remember what had happened? No. It couldn't be. Jenny would never do something like that…at least she never thought she would. But ever since high school started, it seemed that a lot of things Jenny did were once things she considered things she would never do. Had she really changed so much?

"We're going over to Lily's tonight for dinner."

Her father had told her that after Jenny had told him that she had spent the night with Eric. She knew it was a major lie, but it was one that she could pull off because of everything that had happened. It wouldn't have bothered her so much, what with her dad going off about "family," but then he went and mentioned that Chuck would be joining them as well, seeing as it was the only obligation he was giving the woman.

Jenny, in one word, was terrified. She didn't want to see Chuck again, not so soon at least, but this dinner was non negotiable. So, she got ready for it with a dreading feeling in the pit of her stomach.

The blonde couldn't remember being this nervous in her entire life, but as she sat at the dinner table, her father and Lily recounting the details of their trip to Boston, she couldn't help but play with the corners of her napkin. She had kept her head down through most of the dinner, not wanting to look up, especially towards Chuck, in fear that he would recognize her. But thankfully, he remained quiet, except for the few occasional snips towards everyone. It wasn't until desert that things started to get interesting.

"Hey Jenny," Eric said suddenly, "can I borrow your cell phone? I think I left mine with Jonathon and I wanted to call him to see if he could run it over."

She nodded, "yeah, it's in my purse," she said, nodding towards the bag that she had left on the counter when they arrived.

He excused himself as everyone else continued to eat their desert. It was only a few moments later when Eric reappeared and asked if he could speak to Jenny. She stood from the table and followed him into the hallway.

"What is it Eric," she asked.

"I could ask you the same thing about this," he said, holding up the small vile that Chuck had given Jack to give to her that morning.

Jenny's eyes immediately found the floor and she instantly started to get that nervous feeling in her stomach again.

"I, um, I…" she stuttered, her words covering up Chuck excusing himself for the night, "it isn't what you think Eric."

"Isn't what I think," he asked, getting a bit angry, "Jenny, is this why you called me this morning begging me to cover for you last night?"

At that moment, Chuck had stepped out into the hall and raised his eyebrows, "the littlest Humphrey needed a cover? Has she finally caved into becoming one of Blair's lackeys again?"

Jenny didn't turn to look at him, but Eric held of the vile of coke, "Chuck, you look at this, and you tell me what you think it is, because apparently, it's not what I think it is."

Chuck looked at the vial for a moment before taking it from the boy and examining it for a moment. Jenny bit her lip, praying that he would think that she had just stolen it from his stash if he recognized the bottle.

His eyes flicked up and stared straight into her blue ones, "it was you," he asked quietly.