A/N: Ok, here's the next kiss in the lineup. Our boy's all grown up and losing his virginity. Of course, he does it in total Dean style. Hope you enjoy!

Special thanks as always for my girl, Mali Bear's Buddy. The premise for this one was her idea, so I hope I did it justice! She's got a whole great bunch of stories up for all sorts of tastes, so please go read and show her some review love!

Disclaimer: Nope, sorry, don't own Supernatural. Just like to borrow Dean on occasion...

Cindy

He spots her on her way to her car. Cindy Sampson. Blonde. Hot. Head cheerleader. A senior. Recently broken up with the star quarterback. Catnip to Dean Winchester.

Straightening up from the hood of his car, he swaggers over to Cindy and her little VW Cabriolet. "Hey, Cindy," he calls as he checks out her tight cheerleader body clothed in snug jeans and an even more snug t-shirt.

She turns, a bit of a smile turning up the corners of her mouth. Dean Winchester. She's heard all the rumors. He's quite the chick magnet. Especially for a sophomore.

"Hey, Dean," she says, trying to keep it casual. "What's up?"

He shrugs and tosses her a quick smile. "Not much. Just wondered if you were busy tonight. Thought you might want to go out." Out to the backseat of my car, anyway, he thinks.

She looks him up and down with an appraising eye. Maybe the hot as hell bad boy was just what she needed to forget that jerk Donny.

"I could be available," she says coyly. "Pick me up at 8?"

He grins and gives her a salute. "You betcha."

~~~SPN~~~

My God, Cindy thinks from her spot beneath Dean in the backseat of his Impala, those rumors don't even hold a candle to the real thing.

Dean Winchester is even better than advertised. That beautiful mouth of his, currently making its way down her neck, is absolutely scorching. Totally what she needs to ease the sting of Donny's rejection. Bonus: Dean would only be in town a short time, so he couldn't cause trouble when she and Donny inevitably got back together.

He slides his hands under her t-shirt, seeking the clasp of her bra. It'd been even easier than he'd hoped to get her in her current position. He can already tell she's going to let him go all the way, probably to get back at that stupid jock. And he's fine with that. Better than fine, actually, because he's going to lose his virginity to the head cheerleader of Walter Mondale High.

Clothes disappear with surprising speed. There are no words between them other than panted yeses and whispered names.

Dean fishes a condom from his jeans pocket and slides it on. He settles between her soft thighs and looks down at her. She nods.

His mouth finds hers in a heated kiss as he joins them. He moans against her lips. She feels even better than he imagined. Hot and tight around him. He starts to move slowly, feeling her arch beneath him.

He bites his lip, trying to maintain control. He doesn't want her to know this is his first time and losing it now would definitely tip her off.

He kisses her again, tongue sliding against hers. He feels her fingernails on his back and shudders.

It's not too long before she's quivering beneath him and the feel of her body tightening around his is more than he can stand. With a rough groan, he collapses on her.

After a few moments of heavy breathing, he moves away. Another quick kiss and clothes are being replaced almost as quickly as they were removed.

He drops her off back at her parent's house a short time later. She starts to get out of the car, but he grabs her arm and pulls her back. Tangling his fingers in her hair, he kisses her long and deep.

Releasing her, he gives her a heart melting grin. "Thanks," he says simply.

She smiles back. "No," she murmurs as she hops out of the car. "Thank you."

He watches the sway of her hips as she walks to the door, but doesn't wait for her to get inside. Popping his favorite cassette in the tape deck, he turns up the volume and drives away, still grinning.

***You'll recognize our next contestant: Lisa! Stay tuned!