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Give it a Whirl, Give it a Try

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“Hey, Jer…?”

 

“Hmm?” Jerry burrowed himself closer into Dean’s side, body thrumming pleasurably from their intense lovemaking. He inhaled deeply. Content. 

 

“S’it really that good? Having me inside you like that?” He snuggled closer to the younger man, absentmindedly playing with his hair - the short strands tickling his palms. 

 

Jerry let out a sound of contemplation. “Yeah, it feels good. When it hits that spot inside you…” He trailed his finger down Dean’s abdomen - stopping at his belly button then back up again. “It feels real good.” 

 

Dean hummed, decidedly satisfied with the answer.

 

“You wanna try?” 

 

That caught Dean off guard. The question, asked innocently enough, cut through the very heart of what he was thinking. He glanced down and saw Jerry eyeing him mischievously, eyes twinkling in the dim lighting of the hotel room. He blinked. 

 

“Yeah…I guess I do.” Maybe he did want to try. 

 

Jerry scooted up the bed and adjusted himself so that he was on top of Dean, elbows on either side of the crooner’s head and stared. He waited with bated breath for a laugh, a chuckle, anything. 

 

“You’re serious.” He whispered, pulling away slightly but not before planting a kiss on the tip of Dean’s nose. 

 

“I am.”

 

“Oh.” Jerry tried to calm his racing heart. Granted, he had thought of being intimate with Dean in that way - yes, thought. Fantasies on lonely nights when his partner was out of town and the bed felt far too big and far too cold. 

 

Hushed, vulnerable. “D’ya think you can help me with that?”

 

Heavens , he’d hang the stars and moon if that was what Dean wanted. 

 

 “Anything you want, Bubbie.” 

 

———————-



Jerry nervously checked the clock on the wall, signing in relief that he still had about ten minutes left before his partner’s arrival. The jitters were getting the better of him, making him reach for his cigarettes. He lit one and inhaled, nicotine warm and soothing.

 

Sure enough, ten minutes later (and about three smokes in), Dean stepped into the room - looking every bit of the bronzed adonis he was. Jerry felt himself falling in love all over again: nineteen and helpless before the man with the camel-hair suit and the twinkle in his eye. 

 

“Paul,” He greeted, taking one last puff before crushing his cig into the ashtray on a nearby dresser. 

 

“Jerm.” There it was, that gorgeous Southern lilt. 

 

Jerry grinned, anxiety forgotten with Dean’s presence. He crossed the room quickly, arms latching onto Dean’s waist, pulling him in for a searing kiss. Dean moaned, soft, as Jerry deepened the kiss, hungry and intense - arms wrapping around the other’s shoulders as he allowed himself to be led. He broke away first- breathless and panting. 

 

“You go around kissing everyone like that, Mister Lewis?”  

 

Jerry chuckled, still holding Dean tight. “Only the ones I like.” 

 

“Ya like meh….?” Dean put on a cheap imitation of Jerry’s oh so familiar high-pitched catchphrase - batting his eyes in the same coquettish way the younger man would on stage. It worked because Jerry doubled over in laughter, much like their audience on nights when their chemistry shown — like lightning in a bottle. 

 

“You silly meatball, come here.” Jerry drew Dean in for another kiss, this time more loving. Their lips moved languidly, each taking the time to savour one another. Jerry let his hands wander, deftly undoing Dean’s tie, wanting to feel more. Before he could go any further, Dean placed his hand on his - stopping him in his tracks. Jerry froze as if struck, terrified that maybe he was too hasty - that Dean had changed his mind. 

 

“Hmmm, you gonna take me here, Jer?” 

 

Oh.

 

Jerry blushed, suddenly feeling like an inexperienced teen who let his hormones get the better of him. 

 

“I got carried away…sorry, Paul.” He stepped back to allow Dean to fully step into the suite. 

 

“S’alright,” Dean mumbled. “It’s cute.” He tweaked Jerry’s nose as he made his way into the bedroom, letting out an impressed whistle at the way the room was set: lamps set to low, red pillows, towels and other essentials placed strategically on the night-stand. There was only one bed. “You got us a honeymoon suite?” 

 

Jerry turned even redder. He was supposed to be the suave one tonight - the leading man. “I pulled some strings….” 

 

Dean’s lips quirked into a smile. It was endearing, really, the way his partner was so earnestly romancing him. So earnest, that he couldn’t leave him floundering on his own like that.

 

“Well, I’m feeling awfully cold here by myself, Mister Louis. Why don’t you - Ooof!”

 

Jerry tackled Dean onto the mattress, both men giggling as the impact nearly launched them off the bed like human pinballs. 

 

He held Dean’s arms to his sides - immobilizing him and bent down, pressing soft kisses on the elder’s temple. 

 

“Please,” Jerry snickered. “Don’t finish that sentence.” 

 

“I wasn’t gonna say nothin’, sweet-cheeks.”

 

“You mean these cheeks?” He teased, smacking Dean’s behind. 

 

Dean’s eyes crinkled in mirth. “You got me there.” 

 

Jerry’s chest nearly burst with love and adoration, before he could even think his hands were moving, cupping Dean’s face with tenderness. His lips trailed feather-light against his forehead, his cheeks, before going lower - mouthing at the underside of his jaw where the other was sensitive. Feeling bold, he nipped at that one spot - relishing in the way Dean choked back a moan. 

 

He trailed further down, undoing Dean’s button up and shrugging it off his shoulders. His mouth watered at the glistening golden chest before him, dusky nipples begging to be teased and played with. He briefly wondered if Dean would like that. 

 

“Paul?”

 

“Hmm?” Dean sank back into the mattress, cotton sheets cool against his flushed skin. 

 

“Comfy yet, old man?” He cackled, dodging a half-hearted kick from the Italian. 

 

“Gimmie a sec.” He made quick work of removing his trousers, handing them to Jerry who tossed them over his shoulder. He cocked his head, smug, as he caught Jerry eyeing his bulge through his shorts. “Like what you see?” Dean crooked a finger, beckoning. And Jerry, like a man possessed, followed - crawling on all fours.

 

Jerry swallowed thickly. “Yeah, you’re gorgeous, Paul.” 

 

“You’re not so bad, yourself.” 

 

He couldn’t help himself, hands moving to caress Dean’s torso with reverence - tanned skin like silk beneath his palms. He thumbed at Dean’s nipples, gleefully noting the way the other man’s breath hitched - nostrils flaring. He did it again with a bit more force, delighted as the other’s mouth fell open - unable to hold back a sharp gasp. Jerry found it adorable really, the way the little nubs hardened and stood fully erect - begging for attention. He happily obliged, mouth closing over it and suckling gently. 

 

Dean slapped a hand over his mouth before it could betray him again, but not fast enough to muffle the shaky moan that leaked out. 

 

“You like that, Paulie?” He released the nipple with an obscene pop - loving how red and puffy it had become. How it contrasted beautifully against Dean’s sun-kissed complexion.  

 

“I ain’t some broad, pal.” 

 

“Maybe not-” Jerry palmed him through his shorts, leering in satisfaction at the little wet spot that had formed.

 

“-but you’re sure leaking like one.” He purred hotly into Dean’s ear, delighting in his soft gasps as he squeezed harder - teasing long forgotten as the older man arched into his touch, seeking more friction. 

 

“Jer…..please..” He moaned, shivering as Jerry’s tongue traced the shell of his ear. 

 

“Please, what Paul?” He leaned back to get a better look, hazel eyes darkening to a warm honey as he took in the sight beneath him. He knew for a fact that Dean was out of his element here - could see it in his flushed cheeks, in the uneven rise and fall of his chest with every shuddering breath. It filled Jerry with some perverted satisfaction, being able to reduce his cool-as-a-cucumber partner to such a state. 

 

Dean felt himself falling apart. His pride like putty in the hands of a kid nine years his junior. 

 

“Touch me…?”

 

Jerry gave Dean a chaste peck on the lips as a reward before yanking off his underwear and tossing it aside. His eyes widened in awe as Dean’s cock sprang free from its confines - already dribbling pearly precum. 

 

“Look at you…” He whispered in adoration before taking it into his mouth in one fluid motion, tongue swirling around his slit, moaning in delight at the taste that was so uniquely Dean’s. Heady and spicy like his signature Woodhue scent - absolutely dizzying. 

 

Dean groaned appreciatively, one hand curing around the back of Jerry’s neck, the other fisting into the bedsheets as Jerry took him in deeper, swallowing around him.

 

“Oh, Jer…you’re doing wonderful…” Dean caressed his partner’s face adoringly as he slowly began to thrust up into his mouth and Jerry - bless his heart, took him like a champ.

 

The kid never had much of a gag reflex anyway. 

 

Drunk on Dean’s scent and the feeling of his cock hitting the back of his throat, Jerry sucked harder; cheeks hollowed as he did his best to accommodate as much as he could - hands stroking what he couldn’t. 

 

Dean’s moans reverberated around the room. Each one an encouragement, spurring him on. He wanted to hear more. 

 

Dean yelped as Jerry firmly grasped his balls, rolling the sensitive flesh between his fingers. That wonderful pressure coupled with the velvety heat of Jerry’s mouth had Dean coming undone - both hands grasping at Jerry’s shoulders. He was close, he was so close. 

 

“Jer….! I’m - wha?” 

 

Jerry, however, had other plans. He held Dean’s length in a vice-like grip until the man was no longer dangling on the precipice. “Why’d ya stop?” Dean slurred, head slamming back against the pillows in frustration. 

 

“It ain’t nice, leavin’ a man high and dry like that.” Dean scolded. 

 

“Well, I know other ways of making you pop, Paulie.” 

 

“That so?” 

 

Jerry began stripping himself and Dean watched, expression turning hungry at the mini strip-tease the kid was giving him. He nearly moaned out loud, seeing that his partner was just as hard as he was. Brown eyes black with desire, he reached for him, greedy for skin-to-skin contact. 

 

Jerry whined, high and breathy, as Dean rolled his pelvis upwards - impatiently rubbing their cocks together. 

 

“No fair!” He squirmed and bucked, but Dean’s arms were like iron bars around his torso - keeping him in place. 

 

Dean guffawed, loud and booming before sealing his lips over Jerry’s, effectively silencing him. The younger man sighed, kisses becoming dirtier - all open mouths and tongues as Dean did something magical with his hips that had him seeing stars. 

 

His hands wandered down Dean’s sides, then further, until he reached the swell of his ass - palming at the soft flesh. Dean gasped, surprised - kiss forgotten as he trembled. 

 

Jerry pinned Dean’s arms over his head with one hand, the other pinching at his backside. Tit for tat. 

 

“Don’t get fresh with me, boy.” He growled, pinching harder. As turned on as he was by his partner manhandling him, tonight was about making love - Joseph Levitch style. Dino Crocetti’s School of Hard and Fast would just have to wait. 

 

“Alright! Alright! I give, ya skinny bastard - just don’t leave me like this.” 

 

Jerry’s heart nearly stopped when Dean spread his legs invitingly - dark eyes gleaming, curls loosened from their gelled hold. Jerry thought he made for a pretty picture: face flushed, mouth parted slightly as he ground his hips up - chasing the residual warmth. 

 

Craving more of his touch. 

 

“You still want this, Paul?” Releasing Dean’s arms, Jerry stroked the inside of his thigh. Eyes searching for any signs of discomfort or apprehension. Instead, he found warm affection and trust overflowing from those deep browns. Dean nodded once and oh, once was all Jerry needed before descending upon him again. 

 

——— 

 

“You still with me, Dino?” 

 

Dean grunted, non-committal. This was too new: Jerry’s hips flush against his, moving in small circles and making a mess of his insides and his head. It felt hot, intense - and with Jerry completely inside him: full. 

 

“You’re doing so good for me, Paul.” Low and hushed, lips at his nape, chest pressed against his back. Again that hand wrapped around his cock - stroking lazily. Then, Jerry snapped his hips forward - no longer teasing. 

 

Something deep inside him was struck, and Dean gasped - back arching, chasing that feeling. 

 

Oh. 

 

Jerry chuckled, breath warm against Dean’s ear. “You feel that?” 

 

Dean clutched at Jerry’s arms, trying to ground himself as Jerry sped up - hitting that spot again. “So this, ah - this is what it’s like?” 

 

“Oh, it gets better, Paulie.”

 

Dean groaned in protest as Jerry pulled out, leaving him empty. But not for long. Impatient hands rolled him onto his back, and Dean grasped at the bedsheets as he was entered again. The hot slide of Jerry’s cock more intense in this new position. His legs wrapped around Jerry’s torso, drawing him closer. Wanting more. 

 

“Better…?”

 

“Mmhmm.” Jerry cooed, gently pushing Dean’s bangs out of his face as he gazed down at him lovingly. 

 

“Show me.” 

 

Jerry took Dean’s hands in his, kissing every knuckle - paying extra attention to the little broken pinky that the older man was so self-conscious about. He kissed it one more time, tenderly, before grabbing a hold of Dean’s hips - thrusting hard. 

 

Dean whimpered, head lolling back as Jerry fucked him senseless - bouncing him up the bed with each stroke. This, this is what he was waiting for. This was what had his little partner screaming for the heavens, that had Dean nearly shouting. He was sure the entire hotel could hear but, curses, he couldn’t bring himself to care. 

 

And when Jerry tugged at his cock, timing it perfectly with the movement of his hips, Dean couldn’t take it - convulsing violently, vision going white as his orgasm shook him to his core. 

 

“Paul….Paul….Paul…” Jerry groaned, head thrown back as Dean clenched impossibly tight around him, milking him dry. He collapsed, exhausted, into Dean’s waiting arms - big hands caressing his back, holding him until the shocks subsided. 

 

Dean broke the silence first, chuckling breathlessly as the last of the fireworks faded away.

 

“Wasn’t that somethin’.” 

 

Jerry giggled, placing soft kisses on Dean’s brow bone as he slowly pulled out - careful not to jostle his partner. He thumbed at Dean’s lip scar before covering it with his lips, sighing blissfully when Dean held his head in place, deepening the kiss. 

 

And when Jerry unfurled himself from Dean’s arms to fetch a towel, Dean laid back - perfectly content to let the younger man fuss over him.

 

“Paul?” 

 

“Yeah, Jerm?”

 

Jerry fidgeted with the towel in his hands. 

 

“Can we maybe do this again? Sometime?” 

 

Dean smiled, eyes crinkling warmly as he pulled Jerry close. He nodded, and Jerry grinned - wide and boyish. 

 

He would definitely do this again.