Rich Boys

Tristian’s mansion is more than impressive, but Dean refuses to show even a mild interest. He knows it will only feed the other boy’s ego and Dean has no intention of doing that. Tristian casually leads him upstairs and into his bedroom, shutting the door behind them.

Dean’s eyes scour the room, smirking. “Nice.”

Tristian walks over and his hands reach out to rest on Dean’s hips, pulling at the belt loops gently. “That offer still good?”

His chest tightening with nervousness he’s never felt before, Dean considers chickening out. It’d make his life so much easier. Things were a lot simpler before he had any reasons to question his sexuality.

Tristian quickly picks up on Dean’s reluctance and slides his hands round the other boy’s waist, rubbing against Dean’s jean-clad crotch, emphatically. “Or maybe you’d rather just get some sleep…?”

Dean closes his eyes, relishing that familiar feeling stirring up all over again. “I don’t know how.” He admits, trying to steady his voice as it threatens to fail him completely. He’s slowly hardening under the attention of those attentive fingers and every logical thought is soon lost beneath the arousal clouding his brain.

Tristian carefully unzips Dean’s pants and slides them, and the boxers underneath, past the other boy’s hips and down to the floor, smiling as Dean obediently kicks them away.

Dean takes the hint and pulls his shirt up and over his head, his cheeks flushing as he feels Tristian’s gaze on his back. He’s almost too afraid to turn around.

“It’s really easy…” Tristian explains, his voice not betraying how mesmerised he is at the sight of Dean’s perfect body. “You can just use your hand if you want…?”

“Have you ever had sex before? With a guy, I mean?” Dean asks, awkwardly, casting a quick look at the bed and imagining all the things they could do on it.

Tristian pulls away from Dean and lifts his shirt over his head, casually tossing it aside. “Why? You wanna fuck me?” He asks, amusedly. He’d expected a blowjob, or at least hoped for one…but this? This was unexpected.

Dean turns around to face him, just in time to see Tristian kick off his pants, leaving them both naked and equally aroused. “Uh…” His thoughts die before they can reach his mouth, the sight of naked Tristian affecting him more than Dean wants to admit.

Taking advantage of Dean’s stunned silence, Tristian leans in and kisses him. He isn’t all that surprised when Dean responds with a lot more enthusiasm than before. The kiss deepens as they feed of each other’s growing confidence, spurred on by the unmistakable signs of arousal pressing against each other as their bodies lock together.

Dean finally breaks the kiss as he feels the edge of Tristian’s bed digging into the back of his knees, threatening to knock them both off their feet. Still excruciatingly close, Dean looks nervously at Tristian. “Maybe you could. I don’t know how.”

“You want me to fuck you?” Tristian asks, so horny that the thought of sinking his cock deep into Dean’s ass brings him close to coming there and then.

Dean nods, the slight movement of his head the only kind of admission he can make. He’s not even sure why he trusts this guy, or for that matter why he’s doing any of this. It’s out of character for him and he knows it. Strangely enough, though, it feels good to stop being good old dependable Dean for five minutes. It’s liberating. “Yeah.” He says, finally, the word feeling all kinds of scary as it leaves his lips. His body is practically trembling with excitement.

“You sure changed your tune.” Tristian quips, unable to resist it. “Not that I’m complaining.”

Dean can’t and won’t explain it, he just grabs the blond by the back of his neck and pulls him into a kiss that sends them both over the edge and down onto the mattress, neither breaking away from the embrace. Their bodies have soon heated up and Dean is fascinated with the baby-soft skin pressing up against his own. His fingers trace the outline of Tristian’s chest, carefully circling each nipple, before his lips lay a trail of kisses leading down towards the other boy’s navel.

“Keep going.” Tristian urges, closing his eyes as Dean’s lips get increasingly close to his desperately hard cock.

Dean fights back the thumping fear gripping his chest and gently drags his lips up the stiff shaft, taking the tip into his mouth. At the sound of Tristian’s hitched breathing, Dean lowers his head, feeling the smooth skin slide against his tongue and to the back of his throat. He’s vaguely aware of Tristian’s hand in his hair, gripping just that little bit too tightly, sending shivers across his scalp that quickly spread across his entire body.

“You gotta stop.” Tristian calls out suddenly, his voice strained. “I’m gonna come too soon if you carry on.”

Dean reluctantly withdraws, feeling rather dazed at the thought of what he’s just done and how good it felt to do it. “Do you have protection?”

Tristian crawls over to the other side of the bed and opens a drawer off to the side, quickly returning with a handful of condoms and a half-used tube of lubrication.

Dean blushes at the sight. “Guess you are experienced, then.”

“I’ve never done this before.” Tristian admits. “But I know what I’m doing.”

Nodding hesitantly, Dean watches Tristian slide a rubber over his cock before covering it with lube. He lets the other boy guide him onto his back, spreading his legs as Tristian’s hands gently push against his thighs.

“Just relax.” Tristian warns, sliding a lube-coated finger into Dean’s ass.

Dean grimaces slightly, but the feeling is far better than he thought it would be. Unable to resist any longer, he wraps a hand around his cock and begins sliding his fist up and down the shaft, groaning as Tristian slips in a second and third finger.

“You have no idea how fucking good you look right now.” Tristian drawls, dragging his eyes down every inch of the beautiful body laid out before him, just waiting to be fucked into oblivion.

Blushing once again, Dean bites his lip to hold back a moan as Tristian withdraws the fingers from inside him.

“You sure you wanna do this?” Tristian asks for the last time, not sure he could stop whatever the answer, he needs this so badly.

“You stop and I’ll kick your ass.” Dean threatens playfully, smiling as Tristian moves over him and presses his cock against Dean’s entrance, hesitating briefly before pushing inside slowly but forcefully.

The initial pain is enough to make Dean cry out, prompting Tristian to slow down until he can adjust. Eventually, Dean demands that Tristian continue, especially when Tristian’s hand replaces Dean’s own around his cock, timing each hand movement to Tristian’s thrusts. Overwhelmed by the dual attack, Dean’s fingers clasp at the bed sheets, pulling at them to relieve the intense pleasure invading every inch of his body.

The sensation of being inside Dean like this is no easier for Tristian, who can feel his orgasm coming far sooner than he would have liked. Seeing Dean in such tormented pleasure, losing control beneath him, Tristian can barely contain himself. Feeling Dean’s muscles clamp around his dick as the other boy comes in Tristian’s hand is enough to trigger Tristian’s own climax, emphasised by one last thrust deep into Dean’s ass. Out of breath and more than a little messy, both boys collapse beside each other on the bed, their arms touching as their last form of contact.

“Fuck.” Dean mutters, staring up at the ceiling, still a little delirious.

“If you’re going to freak out, can you at least wait until tomorrow?” Tristian asks, his heart pounding in his chest as he tries to catch his breath.

“Not freaking out.” Dean states, surprised at how calm he feels. Apart from his own laboured breathing and the small amount of pain still remaining, he feels better than he has done in a long time. He looks over at Tristian with something resembling affection in his eyes. He can’t help but feel something other than distain and attraction, not after this. “What are we gonna do tomorrow?”

Tristian has no idea. He hasn’t exactly planned for this. Usually after getting into a girl’s pants, he drops her and moves onto the next, but things are different this time. And not just because Dean is a guy.

“No idea, huh?” Dean smiles. He already knows what Tristian is thinking, can see the same expression on the blond boy’s face that he’s sure he’s wearing at this moment in time.

“How about we deal tomorrow?” Tristian asks, eager to get some sleep.

Dean reluctantly nods and wonders whether he should get off the bed and find somewhere else to sleep. His question is soon answered, however, when Tristian leaves his side to get under the covers, offering the other side of the bed to Dean. They don’t snuggle, but without either of them really meaning to, they end up lying close enough for just a small part of their skin to touch. And before they even realise it, they’re fast asleep.

*~*~*~*

Tristian wakes early the next morning only to find the bed half-empty, with Dean nowhere to be seen. He wipes his eyes and stretches, trying to wake his body up, not sure what to do now he’s been abandoned. Though he knows its likely Dean has freaked out and left to avoid the awkwardness, he’s already planning his next time to Stars Hollow, in the hopes that maybe that’s not the case. A guy can hope after all.


End.

Sorry I took so long! Your reviews really helped me get this done, so thanks! I'm up to season two of GG, so the lack of Tristian in this season didn't help my muse much. However, the arrival of a new hottie could definitely have a positive influence. So, hopefully I'll be back sooner or later with a Dean/Jess.