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Jack isn’t really sure what he’s doing here.
Obviously, he knows his motivations for plucking up the courage to finally enter the gay club he’s been circling for weeks, but now he’s inside, he’s not sure what to do.
It’s dark and loud, with flashes of neon illuminating the crowded room. There’s barely enough space to sit comfortably at the bar he’s parked himself at, nursing some mixed drink he let the bartender pick for him.
He looks out at the dance floor. It’s too intimidating for him to actually consider joining, but maybe one day, when he’s gathered more confidence and is dressed more appropriately. Jack tugs at the loose sleeves of his sweater. Everyone else is wearing something extremely tight or see-through, but he’s in the same clothes he wore to class earlier. He turns back to the bar and focuses on his drink.
A man squeezes in next to him. “Another one, please,” he asks the bartender. He’s facing away from Jack, giving him a full view of his thin waist, accentuated by the flowing hem of his cropper shirt. Between his shoulder blades, a blue caduceus is stamped on the fabric.
“I like your shirt,” Jack says.
The guy turns around. His face is just as pretty as his waist. “What?”
“Um.” Jack swallows, his ears are burning, and as much as he wants to hide in shame, he’s too enchanted by the man in front of him to look away. “I- I like your shirt. The caduceus.” He juts a thumb over his shoulder.
Pretty boy smirks and tilts his head; a gold earring flashes in the light. “Here I was thinking you meant the half that’s missing.”
Jack’s cheeks flush. On instinct, his eyes dart downward to get a quick look at the exposed, smooth stomach decorated with a thin, happy trail leading into tight jeans.
“Uh, well, that—“ Jack clutches his drink like a lifeline. “You look nice. Yeah.”
The man coos. “You’re so cute,” he says, pinching Jack’s cheeks. “You’ve never been here before.”
It’s not a question, but Jack answers anyway with a soft, “No.”
The man released Jack’s cheeks in favor of cradling his chin, tilting it upward as he leans in close. “Have you ever done anything like this before?”
“No,” Jack repeats, even weaker than the first one.
The man’s free hand cups the back of Jack’s head and plays with his curls. “Do you want to try it?”
Jack can’t speak anymore. He’s too engrossed by the beauty in front of him, touching him. An enthusiastic nod is his only answer.
The bartender arrives with a shot, and the man slams it down in one go. “Close me out, Ben.” After he passes his card over the counter, he presses closer until he’s practically sitting in Jack’s lap.
Jack prays his growing erection isn’t too obvious, but the way the man’s smug expression deepens tells him it is.
“Quick chemistry test.”
“Wha—“ Jack’s words are left in his throat as soft lips push against his. He lets his tongue be pushed around and enjoys the buzzing pleasure spreading through him.
It takes the bartender shoving pretty boy’s shoulders to break them apart. He hands back the card. “Have fun, be safe,” he says with a wink.
“Always,” the man says. “Come on.” He grabs Jack’s hand and leads him to the exit. Standing, it’s incredibly obvious how embarrassingly affected Jack is by a little kissing.
“The name’s Robby by the way.”
“Jack.”
Robby’s eyes shine. He takes Jack’s hand in his own, “Nice to meet you.”
They decide on Jack’s place since it’s closer, and Robby holds his hand the whole walk there. Jack’s heart thuds like drums in his ears, and they’ve only had one kiss; he’s worried he’ll explode the second Robby starts to strip.
“This is it,” Jack says, presenting the tiny apartment.
“Very nice.”
It’s really not. The paint is chipping, and Jack’s laundry is strewn across the couch. His face becomes impossibly hotter; if there was ever a reason to get more strict about his house chores, hot guys unexpectedly inviting themselves over is it.
Jack’s really not sure what to do now. “So…”
“This your bedroom?” Robby points to a door that Jack didn’t bother closing all the way.
“Uh, yeah.” Jack hurries inside and begins to gather a pile of textbooks and loose notes scattered over the bedding. “Sorry,” he chokes. “Wasn’t expecting company.”
“That’s okay,” Robby says. “My place looked similar when I was still in school.”
“How long ago was that?”
“Not that long.”
“No, sorry,” Jack rushes out. “I didn’t mean it like that. You look great. Beautiful.”
“Beautiful?” Robby teases. “That’s very nice of you.” He traces his fingers under the hem of Jack’s cable knit sweater. “You look hot in this.”
“Oh, no,” Jack shakes his head. “I was thinking you must be freezing.”
“Didn’t mean temperature.”
Jack lets out a humiliating squeak.
“So,” Robby says. His hands trail farther across Jack’s pudgy skin. “When you say you’ve never done this before, do you mean, like, pick someone up from a bar?”
“Uh.” Jack desperately tries to keep his voice from stuttering. “I’ve given a handjob before.”
Robby’s mouth twists like he’s suppressing a laugh. “Okay. How old are you?”
Jack shrinks. “24.”
“That’s fine,” Robby assures. “We all start somewhere; I just didn’t want to be cradle robbing.”
“I want to do more, though,” Jack says. “And I’m a fast learner.”
A warm smile stretches across Robby’s face. “How about a blowjob?”
Jack swallows. “I— Yeah, I can do that.”
“Oh, no.” Robby pushes him onto the bed. “I’m doing that. But it’s sweet of you to offer.”
He yanks Jack’s jeans down and mouths at the wet spot peaking at the tent in his boxers.
Jack gasps. His hands fly to Robby’s hair, he rips them away and digs his nails into his knees, only for Robby to put them back.
“Pull on it,” he says, eyes dark. “It’ll make me hard.”
Robby grins at Jack’s shuddering breath and lowers his mouth back to Jack’s clothed dick. He teases him with his tongue through the cotton, and Jack thanks his lucky stars he isn’t cumming from the sight alone.
“You’re really— You’re really beautiful.”
Robby’s shining, brown eyes are addictive.
“I can’t, I can’t believe someone like you would go home with someone like me.”
Robby pulls away, his large hands massaging Jack’s thighs. “Not bad yourself. Cutie like you, I’m surprised no one snatched you up sooner.” He tugs at the elastic waistband. “Can I?”
Jack nods furiously. Robby slowly pulls down his underwear, exposing himself inch by inch until his cock springs upward. When it does, Robby’s mouth drops open, and his dark eyes become even more focused.
After what feels like an eternity of silence, Jack begins to fidget under the attention. “Um, sorry. I—“
“Don’t be sorry,” Robby says, still staring. “You’re bigger than I thought.” Without another word, he swallows Jack down to the hilt.
“Fuck,” Jack gasps. His fingers pull at Robby’s hair in a way that should be painful, but Robby’s answering moan sends a sinful vibration through him. “Oh, my God.”
Robby pulls off, dragging his tongue along the underside until he reaches the head. He kisses the tip and says, “Tell me when you’re close.”
“I’m close,” Jack admits.
Robby chuckles. “When you’re actually close. I want you to be able to fuck me.”
Jack’s face twists, and his hands claw deeper in Robby’s hair. “That’s not helping.”
A pretty hum rings from Robby’s throat. He licks at the head, taking every bead of pre-cum before kissing along Jack’s length.
“I’m close,” Jack says. It’s embarrassingly quick, but it’s the truth.
Robby wraps one firm hand around the base of his cock and grips tightly. “Give me a little longer.” He takes Jack back in his mouth, moving up and down, sucking deliciously around him, and only stopping when his lips meet the firm hand holding back Jack’s orgasm. Jack’s thighs quiver at the feeling of his tip gliding down Robby’s throat. His fingers are wound so snug in Robby’s hair, Jack has to remind himself not to rip any out. Finally, after what could’ve been a minute or an hour, Robby releases him with a gasp.
“Good job,” he says, breathless. “You didn’t come. I’m impressed.”
Jack flops back onto the bed, stars in his vision, and leaking cock dribbling over his stomach. “Thank you.”
“I’m not done yet. Got any lube?”
The haze in Jack’s mind isn’t enough to stop the image of what Robby could look like, wet and open. Jack drags himself to the bedside table and pulls out a half-used bottle.
“Very good,” Robby says. He strips without any hesitation. Leaving his cropped shirt and cruelly tight jeans in a heap on the floor. Jack’s eyes go straight to Robby’s dick. It’s long, slender, and pretty like the rest of him. “Might want to take your sweater off.”
“Huh? Oh, yeah.” Despite his most private area already being exposed, there’s something about being totally nude that makes Jack want to hide. Not that Robby gives him the chance.
“Alright, cutie,” he says. “Time for you to do some work.” He crawls to the top of the head and settles on his hands and knees.
Jack swears his heart stops.
Shiny metal is nestled between Robby’s cheeks. Calling Jack like a beacon. “I— Can I—“
“It’s been in all night,” Robby whines. “And it’s so tricky from this angle.” He looks over his shoulder with a fake pout, though it strikes Jack all the same. “Help me?”
Jack reaches out and tentatively rubs the base, wiggling the plug inside Robby.
A sharp moan erupts from Robby. “Pull it out,” he pants. “Need more lube.”
Jack draws the plug out carefully. It’s wider than he thought; he can’t believe Robby’s had this inside him for so long. Once it’s fully out, Robby’s hole winks at him, and the few drops of blood remaining in Jack’s brain flow south. His cock drools on the sheets below.
“Okay,” Robby’s breathing gets heavier. “Put more lube on, and put it back in.”
Jack does as he’s told, admiring the way Robby’s body sucks the plug back inside, clenching around the widest part, then shrinking before the base. He maneuvers it in and out of Robby at a steady pace, twisting his wrist and trying new angles that make Robby shudder and moan in a way that’s better than any porn Jack’s ever seen.
“Jack,” Robby pants. His voice is muffled from where his arms have given way and landed his face in the pillow below. “Get the condom out my pocket,” he says, pushing himself back up.
It’s not easy convincing himself to let go of the plug, but when he realizes what Robby is really asking for, Jack stumbles over to the discarded jeans in record time. By the time he’s back on the bed, Robby has taken the plug out.
He grabs Jack by the shoulders and pushes him on his back against the mattress. Robby rips the foil open and rolls the condom onto Jack’s bright red cock.
“I’m going to ride you,” he says as he spreads a generous amount of lube over the latex.
“Please,” Jack manages.
Robby smirks and lines himself over Jack. “Ready, cutie?”
There’s no way Jack could ever be ready for someone like Robby, but he nods anyway.
The tight heat of Robby around him is better than he ever could have imagined. He throws his head back and almost howls at the feeling.
“So good.” Robby’s jaw hangs low. “So fucking big. Fuck, cutie, who would’ve thought?”
He links his fingers between Jack’s and uses the leverage from Jack’s elbows pressed into the bedding to start his rhythm.
“You feel so good,” Robby babbles. His dick smacks Jack’s belly with every bounce. “So good, baby. You’re so big, so perfect. Fuck.”
Jack can’t speak. He wants to. There’s a desperate need in him to tell Robby how beautiful he is, and how unreal the pleasure he’s providing is, but the words won’t come out. They tangle in his throat and escape as broken moans.
Robby clenches around him as his rhythm starts to unravel.
Jack whimpers. “I’m gonna come. I can’t stop it.”
Robby shakes his head. He speeds up until he’s slamming down on Jack’s hips with each jump. “Don’t hold back. Give it to me. I want to feel it. I want to feel you come.”
That does it. The hot coil in Jack’s gut snaps and flows out of him in thick spurts, filling the condom. Robby rides him through it, keeping up with the wonderful squeezing on Jack’s cock as he milks him dry.
“So good,” he sighs.
Without thinking, Jack untangles one of his hands and begins to pump Robby’s cock, rewarding him with a sharp gasp.
“You do have experience with this,” Robby laughs. He circles his hips, Jack’s soft dick still inside him. “Shit, that’s good.”
Jack’s chest swells with pride, and he works his hand over Robby’s dick until he releases onto Jack’s stomach.
“Shit,” Robby pants. His chest rising and falling like he’s run a marathon. “You were right; you’re a fast learner.”
Mercifully, the sweat and flushed skin from their activities hide Jack’s newest blush. “Thank you.”
“No problem.” Robby removes himself with a gentle pop and stands on shaky legs. “Got a washcloth?”
“Oh, yeah. Let me…” Jack scurries off to the bathroom. When he returns, with a freshly cleaned stomach, Robby pulls his shirt back on. “Oh, uh—“
“Thanks,” he says. He cleans his crotch and moves to pull his underwear back on.
“You could stay,” Jack tumbles over himself to say. “You, if you want. Obviously. I, um.” He looks at his feet; his nude lower half greets him with vulnerability. “I could make you breakfast.”
He looks up to see Robby studying him. After a moment, he smiles. “How could I say no to that?”
A weight relieves itself from Jack.
Back in bed, Robby snuggles against Jack like it’s second nature. Tucking his nose into his neck, and curling an arm over his chest. Just as Jack’s eyes start to droop, Robby whispers, “I’ve got more to teach you anyway.”