Emily (iluvroadrunner6) wrote,

Dean/Angell - Karmic Payback

Fandom: CSI:NY/Supernatural
Title: Karmic Payback
Author: iluvroadrunner6
Rating: PG-13 // FRT
Characters: Dean Winchester/Jessica Angell
au_developments Prompt: 10. Long Time Ago
Content Warning: N/A
Summary: Dean and Angell run into her old boyfriend from high school in a bar.
Author's Note: For afteriwake and toxic_shadow who I just realized both requested Angell for Virginity Meme. And wow I haven’t written these two in a while.
Disclaimer: I don't own the characters of CSI:NY or Supernatural. They're owned by CBS and the CW. However, all original characters are mine, so please do not borrow them without my permission.

“Winchester, I swear, if you’re laughing you’re getting decked in the face.”

She watched as the shit-eating grin that was on his face two seconds earlier immediately dropped, and Dean’s face sobered like a pro. “Laughing? Me? Please, Jess. Give me a bit of credit for having some sensitivity.” He paused for a minute, before smirking back at her as he slid an arm around her shoulders. “Though, it’s really isn’t all that much.”

Angell flashed him a death glare, and he sobered again, or at least tried. Angell just shook her head before running a frustrated hand through her hair. “Should have just kept my mouth shut.”

“Aww, c’mon, sweetheart,” Dean said with a sigh looking over at her from under his arm. “Everybody’s got embarrassing first time stories.”

“Mmm-hmm,” Angell sighed softly, before leaning in to him, a slight pout on her face. “He looked better in high school.”

“You mean—he actually had hair then?” he teased, giving her a grin as she glared at him again.

“Yes, he had hair,” she sighed, before looking down at the ground. “And abs. And—was generally better looking.”

“Well, not everyone can look as good as they did in high school,” Dean said smugly, and Angell pulled away from him slightly, giving him a skeptical look.

“You do not look as good as you did in high school,” Angell shook her head. “Your genes are not that fantastic.”

“Oh, they are,” he grinned, watching her roll her eyes. They walked in silence for a moment, before he looked back over at her again. “So how’d it happen?”

Angell looked over at him, confused. “How’d what happen?”

“How’d you—” He tilted his head back and forth for a moment, before giving her a grin. “—you know.”

“How’d I lose my virginity?” she asked, raising an eyebrow at him slightly.

“Yeah. That.”

At that she actually laughed, though it wasn’t necessarily a happy one. “Yeah, no.”

“What?” Dean said, giving her a look. One could almost say he was whining. “C’mon, tell me.”

“Are you gonna tell me yours?” she asked, crossing her arms in front of her chest.

“Sweetheart, if I could remember I would tell you,” Dean admitted with a grin. “Spill.” He paused when her look didn’t lessen, and he tried to do his best impression of Sam’s puppy dog eyes. “Please?”

“Dean, it was a long time ago—”

“Color me curious.”

She sighed slightly, looking exasperated, before going in to the story. “It wasn’t the greatest experience in the world. Joey—was never really all that great a guy, but I’d had a crush on him for as long as I could remember and he wanted to go out with me. We dated for a while, I wanted him to stick around so—”

“You put out.”

She gave him another look. “I’m not happy about it, alright? But that’s how it happened. Besides, he did the whole thing where he made me feel loved and wanted and stuff, so—I was okay with it at the time. It wasn’t until afterwards, when he was dumping me for a college girl that I felt like an idiot.”

“Douchebag,” Dean said, shaking his head.

“Oh, like you were any better.”

“Hey, I had a valid excuse!” Dean said, giving her a look. “Longest I ever stayed in school was a month. I was just looking for a bit of quiet comfort in my tumultuous young life.”

Angell stopped right where she was walking, turning to smack him on the shoulder lightly before she continued walking. Dean gave her a grin, before moving to catch up with her and draping an arm around her shoulders again.

“And hey, if you ask me, you got the payback in the end?”

“How’s that?”

“Well, you wound up hot—he’s the one who’s balding and got a beer belly before he’s thirty-five.”

She paused, looking back at him for a minute before snorting slightly. “Yeah. That’s really a win for me.”

“I’m just sayin’,” Dean grinned. “As far as karma goes, it certainly seems like he’s getting his.”

Angell thought on this for a moment, before shrugging slightly and continuing to make her way down the street. “Eh, we were even back then—after I told my four older brothers what the guy had did to me, and they kicked his ass into the middle of next week.”

Dean had been following that for a moment, before his face contorted in a frown, and he looked over at her. “Four older brothers?”


“That doesn’t bode well for me, does it?”

“Nope. Not at all.”

“Great,” Dean said with a sigh as he continued to follow her out of the room, rubbing his eyes lightly as he did. “Just great.”

Tags: crossover}: ship ~ dean/angell, fandom}: csi: ny, fandom}: supernatural, prompts}: au_developments, series}: family ties

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