-1A/N: Alright, so I've had this idea floating in my head for awhile, and I need to get it out on paper, or it will never go away. Takes place during late third season, Jess and Rory have been dating awhile, and Jess gets a visitor from his past.

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Jess and Rory were sitting alone in Rory's living room watching a movie, when Rory got the urge to ask Jess a question. Lately the sex issue had been on Rory's mind a lot, and she had decided a few days ago that she needed to know a bit about Jess' past sex life before they began theirs.

She lowered the volume to almost nothing and turned to Jess.

"What?" Jess asked.

"Are you a virgin?"

"What?" Jess asked shocked and completely turned to Rory.

"Are you a virgin?" She repeated slower.

"Are you serious?"

"Yes."

"No."

"No you're not a virgin?" Rory clarified.

"Yes."

"Yes, you're a virgin?" She was confused.

"No! I'm not."

"Oh." Rory looked down to her fiddling hands.

"Is that all?" Jess said a bit annoyed. He'd never liked getting into personal stuff. Why would he want to suddenly do it now?

"When did you lose it?"

"Why are you asking me this?"

Rory doesn't look up from her hands. "Because, I've been thinking about, you know, it. And I decided that I want to know a little more about you before we go into that."

"Oh." Jess said completely shocked. He hadn't known why she was asking him, but he sure as hell didn't expect her reason to be that.

"So?"

Jess looked back to the T.V. and replied numbly, "Twelve."

"Twelve years old? Wow." Rory couldn't even remember having a crush at twelve, much less lose her virginity then.

"Yup."

"Do you regret it?" She glanced up at him.

Jess looked directly at Rory. "No."

"You don't?" She's shocked.

"No. I had a girlfriend. She was curious, I was curious." Jess shrugged. "It just worked out that way."

"Oh." Rory looked down at her hands again.

"I should go. I have to open the Diner tomorrow." Jess needed an excuse to get out of this conversation. "You'll stop by?"

"Yeah." Rory looked up to a now standing Jess. "I need coffee, and where else would I get it?" She tried to lighten up the mood.

"How flattering." Jess leant down and kissed Rory's lips briefly before stuffing his hands in his pockets and walking to the diner thinking about the girl he lost his virginity to. Cassie.

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A/N: Okay, so this was a short chapter, I know. And sorry it kind of sucked ass. It will get better, I promise. And it's a lit so don't fret my little readers. I just wanted to write a little about Jess' past and why he actually got sent to Stars Hollow. I know that why he was sent to Stars Hollow has been done before, but I doubt that this will be the same.