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It’s Jack’s fault. Jack, who is all too happy to stand up shots for the table during a rare night out with a mix of day and night shift, and pass one after another to Robby with a wicked glint in his eyes as Robby downs each successive shot. They’re not quite drunk when they say their goodbyes—everyone else at the table glassy-eyed and about ready to order another round—but they’re both feeling loose, their buzz enough to warrant Ubers back to their respective homes.
Robby is only back at his condo for ten minutes, just finishing a second glass of water and two ibuprofen, when his phone buzzes. He glances down and sees the notification from Jack.
can’t hang like I used to. bet those kids will be out for another three hours and then roll in tomorrow morning looking like they got eight hrs of stone-cold sober sleep
Not us anymore, brother, Robby commiserates. Then, before he can think better of it, the edge of his buzz hanging on, adds, Can’t even get myself off the way I used to.
He stares at his phone, at the reckless message he sent, his body heating, watching the dots on his phone pulse as Jack types a response. Robby considers sending a quick follow-up, something to deflect or change the topic, when Jack’s message pops up.
No problem, we can solve this, brother
Robby’s trying to figure out what the hell that means, when another message comes through:
Show me your technique
Immediately, Robby shoots back a series of question marks, certain that Jack can’t be asking for what it sounds like, because what the fuck? The wait for Jack’s next message feels interminable, his stomach flipping, though he’s not sure if it’s from nerves or anticipation.
Record yourself. Send me the video. I’ll fix your problem.
Robby’s not sure what he’s thinking—if he’s thinking this through at all—when he climbs onto his bed, tugging the comforter down, and shimmies out of his clothes, propping himself up on pillows against the headboard and pulling out his phone. He angles his camera down toward his cock and hits “record” before he loses his nerve, and takes himself in hand, a quick spit into his palm to slick the way.
The idea that Jack is going to see this simmers in his skin, squirming arousal and embarrassment turning his face beet red in the reflection of his phone as he strokes himself, hardening in his hand much faster than he’s accustomed to, especially after a few drinks. He watches the phone in his hand as it records, trying to keep his hands steady and the view centered, not quite putting on a show, but still very aware that he’s sending this recording to Jack.
Robby knows the point isn’t to try to get off; Jack wants to see technique. So after a few minutes, when his cock is full and flushed, filling the screen, he ends the recording, swipes back to the text thread with Jack, and with his heart racing, sends the video.
Seconds later, a new text comes through from Jack: Roger. Hang tight while I watch.
For nearly five minutes, Robby sits in silence, his chest tight and his gut twisting, as he questions all of the choices that brought him here: waiting alone in his bed in a near panic, with a flagging erection while Jack watches a recording of him jerking off.
When his phone rings, startlingly loud in the silence of his bedroom, he’s almost afraid to answer.
“What the hell? You’re ignoring your balls, man.” Jack sounds completely unfazed, jumping right in once Robby picks up.
“Did you seriously call me to say that?” Robby says, disbelieving and flushing at the hard proof that Jack had been watching a video of Robby jerking off.
Jack’s so nonchalant in his assessment of Robby’s masturbatory technique that it throws him off guard—so much so that when Jack changes the phone call to video, Robby doesn’t even think about the fact that he's naked on his bed with a spit-slick semi when he taps “accept.”
“Aight, here’s what we’re gonna do, you’re gonna show me that again and we’re gonna workshop it,” Jack tells him, like they’re discussing a new intubation technique. Robby can see the background of Jack’s condo, recognizes his bedroom. He’s in a different shirt now than he was in the bar.
“Workshop it?” Robby asks incredulously, adjusting the phone so only his face is in the frame,
“C’mon, man, prop the phone up on something and go again,” Jack tells him.
Robby hesitates, thinking about the lunacy that is his life right now as he nestles his phone among a pillow and the pile of blankets to his side, looking over his thigh. In for a penny, he thinks, telling himself it’s the last remnants of his buzz giving him the courage to go through with this, that putting the brakes on now would somehow be even more uncomfortable than wrapping his hand around his cock again, and stroking from root to tip while Jack assesses.
“Are you using lube? You didn’t look wet at all.”
“I’m trying to get off, not make a production out of it,” Robby huffs.
“For fuck’s sake. No, literally, for fuck’s sake. Get the lube, what’s the point of doing this halfway?”
“Are you always this bossy?” Robby gripes, trying to ignore how Jack’s voice makes him squirm. He grabs the lube out of his nightstand.
“I am when I’m right. Go on, treat yourself to the basics.”
The intensity of Jack’s eyes on him feels like a touch. His face and shoulders fill up the screen as he watches closely, as focused as if this were a procedure he’s teaching. Robby can tell what’s visible to Jack, the corner of the screen showing him what Jack is seeing: the pale expanse of Robby’s thigh and chest, all the dark hair, and his hardening cock, while he tries not to breathe too hard as he goes back to touching himself.
“Slow down, man, what’s the rush? You gotta tease yourself, really enjoy it. You should enjoy this, what your body can feel.”
Robby shivers at the low rumble of Jack’s voice and slows his hand; Jack’s attention is thrilling, and he’s even harder now as he strokes himself, wet and slick and wanting. It’s all he can do not to react as Jack leans forward toward the camera, like he’s trying to get a better look at what Robby’s doing.
“Enjoying the view?” Robby is going for casual, trying to match Jack’s nonchalance, but he hears the strain in his voice.
“Why do you sound so tense while you have your hand on your dick?” Jack asks, and Robby swallows around a groan.
“If you’re so good at this, put your money where your mouth is and show me how it’s done,” Robby tries to grumble, trying to hide how much performing for Jack is doing it for him.
“Alright,” Jack says, easy as anything, as if that suggestion had been more than Robby getting defensive, like it had been a reasonable request.
But Jack’s already moving, the video wobbling around as Jack moves his phone and sits back, and before Robby can wrap his mind around what’s happening, Jack has stuck his thumbs in the waistband of his sweatpants and pushed the whole lot off, bare from the waist down as he spreads his legs. Robby’s mouth goes dry when he sees how unexpectedly hard Jack’s cock is, thick in Jack’s hand as he holds himself, his other hand reaching somewhere off-screen.
“There we go,” Jack mumbles, slicking himself up with lube, giving himself a slow stroke.
Robby feels insane. “Jack,” he says, shocked, his own cock suddenly throbbing in his hands, “you’ve got your frenulum pierced?”
“Oh, yeah,” Jack says, like this isn’t a revelation, his thumb coming up to play with the silver barbell that sits just under the head of his cock. “Little present to myself.”
“Present?”
“Yup,” the lunatic says, grinning, pulling on the piercing slightly, just enough to shift it under his skin. Robby can’t tell if he’s throbbing in sympathy or in sheer, shocked arousal. It’s the hottest thing he’s ever seen.
“Now, do what I do,” Jack goes on, letting go of the metal and stroking slowly.
“I am not piercing my dick,” Robby says immediately.
“It wasn’t that bad,” Jack laughs. “And it makes me even more sensitive, so definitely worth it.” The way the head of his cock and that goddamn barbell appear and disappear as he touches himself is mesmerizing.
Robby’s jaw goes slack as he watches the movement of Jack’s hand and tries to match his pace. He’s relieved that, unlike Jack, his face isn’t in the video because he’s sure his expression would give away exactly how turned on he is. He’d never let himself fantasize about Jack, putting Jack firmly in a box labeled “friend,” but now that lid is blown open, and Robby wants.
Jack’s legs are spread slightly, and even on the small screen, Robby can see that Jack’s face is slack with pleasure as his hand moves up and down over his cock, slowly enough that the motion is barely more than a tease, toying with the piercing on occasion. When Jack’s free hand slips down below his cock to tug at his balls, Robby does the same, tugging and rolling his balls in his palm, biting his lip to bite back a groan.
“That’s it,” Jack encourages. “Feels good to play with ‘em.” Jack’s voice is rough when he continues. “Could be better, though.”
“How?” Robby asks, before he can stop himself, squeezing his eyes shut as soon as the question leaves his mouth. But he needs Jack to keep taking, needs to hear that voice guiding him.
Jack is silent, and Robby opens his eyes in time to see Jack spread his legs wider. Then he asks, “Have you ever fingered yourself?”
Robby lets out an undignified sound—a cross between a gasp and a moan—that Jack ignores.
“Helps sometimes when I can’t get myself off any other way,” Jack says, letting his hand drift away from his balls and down between his legs. “Sometimes,” he adds with a wicked lilt to his voice, “it’s just fun.”
Any response Robby might have gets caught in his throat, the mental image of Jack fingering himself making him dizzy with lust. He looks at the screen, where Jack’s fingers disappear out of view, and his cock kicks in his hand at the thought that Jack is touching his hole, right now, on the phone with Robby.
Jack smirks, and Robby flushes, caught, but he’d also swear he sees Jack’s eyes heat right before Jack asks, “Need me to show you?”
Robby’s breath stutters, and he has to squeeze the base of his cock to maintain a semblance of control. His heart pounding in his chest, he nods, then remembers Jack can’t see his face and chokes out, “Yeah. Yes,” trying not to stumble over the words or let Jack hear exactly how affected he is.
When Jack leans across the bed to grab the bottle of lube he’d tossed to the side, his phone tips over, and Robby is stuck looking at what must be Jack’s navy blue sheets for a minute, until Jack returns and repositions his phone between his legs, far enough back that Robby can see Jack’s face, but close enough that there will be no mistaking what Jack is doing.
He’s also removed his shirt. Jack is now completely naked, and his chest—which Robby has seen bared on any number of occasions, but he’s never let himself look—is on display. Sparse hair, stupidly toned pecs, pink pebbled nipples, and, if Robby squints, he’s sure he can see the array of freckles that cover Jack’s shoulders.
Robby is mute on the other end of the screen, afraid of what his voice might sound like if he speaks, though it may be worse when Jack fills the growing silence.
“Much better,” Jack sighs, and rolls his shoulders. He loosely strokes his cock with one hand, and the other comes up to his chest to pinch a nipple. Robby can only stare, mouth dry, while Jack teases himself, pinching and twisting the nub between his fingers while his other hand moves languidly over his erection.
“Was thinking about another piercing,” Jack says almost dreamily, then he looks into the camera. “Think I should go for it?”
“I—” Robby has to clear his throat and slow his hand on his cock, squeeze the base, to tamp down his arousal at the image of Jack with a nipple piercing, at how sensitive Jack would be afterward. “Yeah,” he says roughly, almost too honestly, and corrects himself, adding, “If you want to.”
“I’ll let you know,” Jack says easily, and picks up the small bottle of lube. “But that’s for another day. We’ve got other priorities,” he says, and fucking winks at Robby.
Without fanfare, Jack flips open the cap and coats his fingers with lube, then pulls his left knee up, planting his foot on the bed. Robby wants to pick up the phone, hold it closer, and get the clearest view possible, but he stays rooted in place, eyes locked on the space between Jack’s legs where he’s now circling a finger around his rim.
“Fuuuuck,” Jack breathes, eyes going hazy when he slides a finger in. “You just planning to watch? Point is for you to join in.”
Robby’s heart stutters in his chest, but he grabs lube and coats his fingers on one hand. Just as he’s reaching below his balls, Jack cuts him off, “How can I help you with this if I can’t see what you’re doing. C’mon, man.”
It feels like time is suspended while Robby wipes his hand on the sheet and moves some pillows around to position his phone between his legs. A wave of embarrassment washes over him when he looks at the small image in the corner of his phone—his legs spread, cock still hard and leaking, and now his face is on camera, too, eyes heavy-lidded and skin flushed.
Robby sets the pad of his index finger against his hole and starts to push in when Jack makes a noise to stop him. “Play with your rim at first, don’t just pop it in,” Jack tells him, still rocking his finger in and out of himself. His jaw is slack, his gaze hooded as he leans back, watching Robby through the phone.
“And here I thought I was doing what you were doing,” Robby says, unable to look away from where Jack’s finger is disappearing inside his hole, slow and steady.
“I’m used to it. Are you?” Jack asks and presses a second finger in with a low exhale, the tendons in his forearm flexing with the movement. He pulls both his fingers out a breath later, his hole slick and shiny with lube, and Robby can’t stop the wild curiosity of wondering if he’s tight.
“No,” Robby admits, watching the piercing bobble Jack strokes himself.
“Go on, then, give it a try. Gentle,” Jack says, rubbing at his rim, fingers flat against his hole. “Like this.” He draws little circles around his hole, and Robby, eyes fixed on Jack’s fingers, swallows and mirrors him. His breath hitches at the sensation, little sparks of pleasure making him tremble, and he speeds up, already aching for more.
“Slower, brother. See what I’m doing? No need to rush, let yourself feel it.” Jack guides, his voice cutting through the haze starting to fill Robby’s mind. “Circle your rim…..yeah, like that.”
The encouragement pulls a low moan from Robby’s chest, and he has to close his eyes to center himself, afraid of what Jack can see on his face.
“You’re doing so well for me. Now I want you to ease a finger in…nice and slow.”
Robby opens his eyes to find Jack, once again, sliding a thick finger out of his body, and does the same, sighing in relief as his finger breaches his hole. On the screen, Jack’s eyes are heavy and his lips are parted, and there’s a ragged rise and fall of his chest.
“Perfect. Let your body adjust. Let yourself enjoy it,” Jack soothes as Robby fucks himself on his finger. He releases his cock, which is leaking steadily on his belly, to focus on Jack’s directions.
“Move it around a little, play with yourself, see what you like… does that feel good? Do you want another?”
Jack is sliding two fingers in and out of his hole now, and Robby feels a little breathless when he answers, “I don’t know.” He wants more. He wants to come. He wants Jack to tell him what to do.
Fortunately, Jack seems to know what Robby needs. “Then trust me,” he says, gravel in his voice that makes sparks zing up Robby’s spine. “Give yourself more. Lemme see you fill yourself up. You’re gonna feel so good stretched around those thick fingers.”
“Fuck, okay.” Robby rasps and tries easing another finger in, his head dropping back as he adjusts to the stretch.
“There you go, man,” Jack says on the phone, the slick sounds of his fingers disappearing into his hole never stopping. “How’s that feel?”
“Fuck, Jack,” is all Robby can say, his tone almost a whine with how he can’t seem to catch his breath, overwhelmed by sensation and the ever-present awareness that Jack is watching.
“Talk to me, brother, what do you think?” Jack asks, somehow still sounding in control of himself. Robby, on the other hand, feels insane watching Jack slip a third finger inside of himself, his hole stretched wide. Robby lets out a small whimper at the thought of what else, besides fingers, Jack might have taken.
“Feels huge,” Robby answers, as steadily as he can. There’s pressure around his knuckles, and the blood-warm heat of his own body. “Never felt like this before.”
“Good, isn’t it?” Jack prompts.
“Yeah,” Robby breathes, his hips bucking down into the pressure without his say-so. “Fuck.”
“Gets even better,” Jack says, his voice like honey through the phone. “Angle your hips a little. Find your prostate.”
Robby’s whole body heats, and he pushes back, deflecting, even as he tilts his hips and angles his fingers. “I know how to find a prostate, man, you don’t need to tell me how.”
“Then do it. Show me.”
Robby tries to keep looking at the phone screen—at Jack—but his eyes close of their own volition when the pads of his fingers press against his prostate, his other hand gripping the bedsheets in a tight fist.
“Oh, oh fuck.”
Robby presses harder, and his hips buck against his hand, his moan echoing through the room.
“Fuck, Robby,” Jack rasps, the control in his voice fraying to Robby’s delight. “Like that. Doing so good. Now touch your cock. Lemme see you get yourself off.”
Robby can’t help the heavy breaths and the occasional whimper that escape, one hand on his cock and his other working his fingers in and out. He twists his head to the side and hides his face in his shoulder to try to mute the noises bubbling up from his chest.
“C’mon, Robby, lemme hear you. I’m trying to make you feel good. How will I know if I’m doing a good job if I can’t hear what sounds you make?”
Robby heats, sure he’s flushing all the way down his chest, but his hand speeds up and he lets out a long, low groan, the kind of uninhibited sound he’d make if he were alone. He shoves a third finger in his hole, the stretch so fucking good, and over the rushing in his head and his building orgasm, he hears Jack’s voice.
“Just needed to be stuffed full, didn’t you? Couldn’t get yourself off because you weren’t letting yourself have what you need.”
“Oh, fuck, Jack.” Robby feels cracked open, slick fingers in his hole rubbing bruising circles over his prostate. “Needed this, yeah.”
His eyes feel like they’re about to roll right up out of his skull, pressure building in his gut that he can feel with his pulse, when his gaze lands back on the phone between his legs and the sight of Jack fucking himself on his own fingers, all his languidness gone now, his cock visibly wet with how much he’s leaking.
The noise Robby makes seeing Jack like that is desperate, and one more hard thrust against his prostate shakes something loose inside him. Robby can’t stop the words that slip from his lips as the tension snaps. “You gonna come, too? Fuck. Fuck. Gonna come. Wanna see you. Shit. Oh, fuck.”
He lets out a wild sound as he comes over his hand, his hole spasming around his fingers. “Jack. Fuck.” He forces his eyes open and sees Jack’s composure gone, his hand moving ruthlessly over his cock.
Robby is lucky enough to see the moment Jack comes, see the way his thighs shake just out of frame as his balls draw up and his cock erupts, his fingers still driving in deep inside himself, grinding down on his hand through his release. Jack lets out a guttural groan that makes Robby’s spent cock give a valiant twitch, a noise he’s gonna remember for a very, very long time.
Jack’s got white on his belly, his chest heaving as he slides his fingers from his ass. Robby’s mouth goes dry as he watches how Jack’s hole twitches at the loss and then stays loose and open. Robby follows Jack’s lead, a strange, empty sensation to be sure, and wonders if Jack can see the same, if his own hole looks as ready as Jack’s to take more.
They catch their breath in silence. As they come down, the reality of what they’ve done hits, and Robby starts to grow a little anxious. What’s he supposed to say now? To do now?
But Jack gazes at Robby through the screen, looking wrecked and satisfied, and says, almost lazily, “Got some even better ideas if you’re open to a more hands-on lesson.”
Robby swallows, sparks of surprise and hope blooming, and feigns courage he doesn’t feel. “You think you have more to teach me?”
Jack huffs a laugh, stretches his arms above his head til there’s a pop, leaving Robby distracted by the flex of his abdomen as he moves, the vulnerability of his softening cock, his loose hole. “Could take you on a tour of my toy collection if you want. Or show you how much better it feels when it’s someone else inside you.”
Robby’s cock twitches, trying to pretend he’s got the refractory period of a man thirty years younger. “Are you trying to kill me?
“So is that a yes?” Jack asks, with anticipation and a flash of nerves on his face.
Robby swallows against the dryness in his mouth, looks at his best friend on the camera, naked and vulnerable, alone in his home in another part of the city.
“Yeah,” Robby agrees, and watches as the nerves ease away.
Robby’s at Jack’s door in under an hour.