AN: Hey, This is the continuation from More Than an Arrangement, Playing with Fire and So Far Gone (In that order) So I would recommend reading those first, if you have not! If you have welcome back! ;D

These are just random snap shots, of them getting older etc... I'll let you know how old they are at the start. Each Chapter will be diff little story. (More will be revealed about Jimmy later in case you where wondering)

Dean and Cas are 20... Sam is 16

Mary and John had decided to take a little vacation, just to get away from it all over the summer. They left Sam in Dean and Cas's charge, but the two had decided to stay the week at the Winchester's residence. The heat of the summer was becoming unbearable since Dean had yet to fix the air conditioning unit in their apartment, plus the house staying at the house meant full use of the pool.

Sam had invited Jess over and the two teens where splashing around in the water, Dean had jumped in to cool off for a bit; while Cas lounged, dozing in the sun with his shades on. After a quick dip, Dean pulled himself out of the pool and sat dripping next to the sleeping form. He was starting to worry that Cas was going to burn laying out the way he was.

A cursory glance confirmed that Cas was in fact sleeping, he checked to make sure that the other two weren't paying attention at the other end of the pool. A mischievous smirk spread across his features as he lightly brushed his fingers over Cas's pierced nipple, moving the bar slightly. The dark haired man arching slightly in his sleep and sighing softly, but the action wasn't enough to wake him.

Dean looked up again to make sure Sam and Jess hadn't swam closer as he thumb's Cas's nipple again, producing the same effect.

"You are a pervert," Cas grumbles as he keeps his eyes closed unmoving, his voice deeper with sleep as Dean jumps a little startled.

"I dunno what you're talking about."

"You, trying to turn me on, in front of your brother and his girlfriend," He deadpans.

"I was trying to wake you up," Dean explains, "You need to put suntan lotion on, or you're gunna be a lobster."

"I believe you are quite capable of aiding me without my being awake."

"Dude, not your bitch!" Dean informs him.

"Evidence proves otherwise," Cas smirks up at him.

"What evidence?" He shoots back.

"Last night… Shall I quote you?" he smirks again, propping himself up on his elbows as he opens his mouth to do so and looks at Dean over the top of his shades.

Dean quickly claps his hand over Cas's mouth to stop him, "Who's the perv now?"

Cas pushes Dean's had away, "Still you," he lays back down, "Please…" Castiel pouts and stretches out his arm, whapping Dean in the chest lightly.

Dean glares at him for a beat before conceding, "Fine, but I totally won this!"

"Hmm," Cas hums to placate him as Dean grabs the sunscreen and gets to work rubbing it onto Cas's skin.

"You're lucky I care," Dean grumbles, as he moves from one arm to the other.

"You just want to touch me," he mumbles trying to get back to sleep.

Dean smirks pressing a kiss to Cas lips as he sets out to do his tattooed chest, "Like I need an excuse."

"In my experience you never need one to be a pervert."

"Real funny, babe," he pinches Cas's side, "But what's that say about you?"

"I believe we already established that I'm a male cougar."

"It's manther," Dean corrects.

"Oh, of course," he replies flatly.

From the other end of the pool, Jess was somewhat watching the exchange at the other end; Sam splashing her playfully as they swam around.

"Your brother and his boyfriend are cute," she smiles.

"You're cute," Sam tells her lamely hiding his blush below the water, in an attempt to drown himself of embarrassment.

"That's not what I meant," Jess blushes sweetly, splashing Sam. "They're just like one of those cute older couples, that just…"

"Finish each other's sentences?" He offers.

"No, those couples are creepy."

"Right!" Sam agrees, smiling as they both laugh.

"They just complement each other, ya know?" Jess asks blinking at him.

"What do you mean?" he creases his brow.

She thinks for a moment, idly splashing as she treads water. "I guess it's like when you go to a restaurant and you don't have to change what's on it because whatever you don't like the other person will eat… it that makes sense."

Sam nods as he contemplates what she said before answering, "Ya, I get it."

"I'd like to have that someday," she admits, blushing at her own admission in front of Sam.

"You will!" He blurts, his cheeks coloring worse than hers as his mind quickly back peddles, "I'm mean, um…"

"You're sweet," Jess informs him as she pecks him on the cheek.

Sam's small victory is short lived, however, by Dean whistling annoying as he cat calls at them.

"That side of the pool better be PG…" Dean shouts before adding, "Don't do anything I wouldn't, Sammy."

"Don't call me that," Sam pouts.

"That would make the pool NC-17, Dean," Cas's voice carries over.

Sam slowly sinking under the water wishing he could just die from embarrassment already, as Jess just giggled next to him.

:)REVIEW(: Please! Also PLEASE feel free to suggest different things you'd like to see them do and at what ages! Etc... (Just not them getting Married, because while cute I don't seem them doing that) Any way let me know!