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Tolerable Sex

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“Tell me if it ever hurts. It’s not supposed to.”


“Just try and push like you’re trying to force it out. It’ll open up your body for me. And breathe through it, alright? That matters. Don’t hold your breath, you’re supposed to relax. Focus on your breathing, more than the fact something is going in your ass.”

With a focused expression on his face, Flake nods, readjusting his hands around himself—he’s keeping himself spread for Richard, laying on his back, legs open.

“Alright, breathing. Got it. Child's game. I think I got that down at this point."

Richard leans over to kiss him on the forehead, chuckling fondly.

"I really hope this isn't a child's game."

Flake scoffs with a laugh. Grinning, Richard runs a hand up and down over Flake’s side, and then raises it to cup his cheek, thumb on his jaw. He angles his head to kiss him fleetingly. Flake is nervous, Richard can tell just based on how he returns the kiss. Shaky, tense, and clumsy. Richard presses his lips to Flake’s in one firm push, and then pulls back to search in his eyes. Those eyes are so big and blue, when no longer shielded by his glasses. Flake is so cute. Richard nuzzles their faces together. Flake huffs a laugh.

“Seriously, I don’t want you to be in pain. Tell me if it feels wrong,” Richard murmurs. Flake nods against him. Pulling back, Richard gets settled on his calves and looks down, watching as he gripped his slickened cock, hard in his hand, and rubs the head up and down against Flake’s asshole. Flake shudders at that. He keeps his ass spread for him with both hands, fingers gripping himself, white-knuckled. Richard is already boiling with a heat, from that visual alone. He hasn’t fucked Flake like this before. Just slow, gentle fingering which gradually intensified to using toys. They spent the last two hours stretching him, because Richard has always been insistent on being safe rather than sorry. He’s had a tear or two in the past due to impatience, or a top who didn’t know what the hell he was doing. Not fun. He wants to spare Flake that suffering, not only because it hurts like hell and takes weeks of monitoring your diet waiting for it to heal, but because it would mean he’d get an earful of complaint. So, Richard is in no rush whatsoever. He’ll even redirect them to something else if he has to, if it just simply isn’t working.

“Oh, God,” Flake breathes, watching with wide eyes as Richard shuffles a little closer, just to firmly press the head into his hole. Flake seems to remember his instructions: Richard hears him breathe in deeply, and release slowly. He knows based on experience it’s easier to insert on the exhale. So he waits, continuing to tease his entrance with slow circles of the head, fingers tight around himself, knuckles pressed to Flake’s warm skin. Flake is shuddering already.

“Push,” Richard murmurs, “Push, push. Come on, babe.”

Flake makes the quietest noise in his throat that earns a glance from the other man. Flake has a flustered expression on his face, his cheeks red. Richard does feel him begin to bear down, based on the way his hole flares around the head of his dick, but even so, Richard sits back on his calves, stroking himself idly as he roams a hand up along Flake’s shin. Back and forth, in a reassuring touch.

“You okay? Do you want to stop? We can try later if it feels wrong. If you’re not ready.”

“No, no, sorry—I just—nervous. J-Just put it i-in,” Flake stammers, eyes wide. Richard nods. He looks down, arching his hips in again to press the tip to his slick, pinkened hole. Even if they spent time stretching him, he still looks so tight… Richard really has to fit inside of that. But the human body is amazingly elastic and accommodating—he wouldn’t be surprised if they can manage it. They’d have to, after spending so much time on getting him ready.

With a firm fist, Richard begins to carefully push, while he feels Flake bear down in return. His asshole strains against him, opening for him just a bit, which feels honestly amazing. Richard has to focus. He exhales harshly in a burst, belly a flame of arousal, bottom lip sucked between his teeth. Flake is breathing in deeply, and exhaling the intake slowly, shakily. On that exhale out, Richard puts in a tiny bit more force—and then the head begins to sink in, and his ass opens up. Flake gasps.

“Don’t go tense,” Richard says firmly, a bit excitedly, “Keep pushing. Don’t clamp up.”

“Oh, my God,” Flake groans, “Richard—”

“It’s fine, just bear down. Come on, I’m almost inside.”

Flake obeys. He relaxes back into the pillows, dissipating tension, and starts breathing in deeply once more, focusing on that and only that. Richard feels his inner muscles try to push him out, and in result, it has him sliding in easier. Flake groans. Richard peeks up. He isn’t grimacing in pain. His mouth is open and his eyes are wide.

“Okay, that feels fucking weird,” Flake says, and then laughs. Richard grins.

“It’ll feel good in a second. Just stay relaxed.”

Flake bites his lip and nods. He continues keeping himself spread, body lax, save for his strained, albeit intrigued, expression. Richard grabs the lube previously placed aside, and pops it open. He squeezes a generous amount over his shaft, and down along Flake’s crack. He carefully works his hips in short, subtle thrusts. Little motions of his hips that moves his cock just slightly inside of him. Flake gasps at that, legs tensing. He’s still bearing down, though, which is good. Richard sets aside the lube, and gathers Flake’s skinny legs in his hands. He carefully pins them up against Flake’s shoulders. Flake is looking up at him with awed eyes and a mouth which hangs open in disbelief. Adorable. Richard grins and kisses him on the ankle, hands tightening around his knees. He then peeks down between their bodies. Flake’s hands are still pulling his ass open, giving Richard plenty of access.

Carefully, Richard begins pushing in, slow and easy. He watches his cock sink inside, slight increments at a time—but holy shit, he’s inside of Flake now! He’s so goddamn tight and hot around him—he really can’t believe how it feels. Flake is groaning, and huffing. Richard is sweating already. He’s trying not to slip and let the pleasure get the best of him. This position really helped with easier insertion. He looks up at Flake again, to see a slight grimace on his face.

“Does it hurt?” he asks immediately, concerned, “Should I pull out?”

Flake’s dilated eyes flick up to meet his. He shakes his head quickly, and stammers, “No—it—it just feels strange—and you’re b-big. Can’t—God—it feels so weird. I… I’m not sure if I like it. But keep going.”

He can barely talk coherently. Relieved, Richard nods. He peeks back down to watch himself carefully, gradually sink in the rest of the way. He’s so slick down here, it makes it much, much easier. And Flake is able to stay relaxed despite the initial nerves he must be feeling, which is helpful in maintaining composure. His ass isn’t trying to snap his dick off, which is a good sign. Flake is breathing hard. Richard groans under his breath as he shifts just slightly closer, to really bury into him, his balls pressing to his ass now. He squeezes his hands around Flake’s knees. Flake is moaning, too.

“Oh—kay,” he gasps, and then laughs, earning a smile from Richard, “That’s better. You’re… You’re so… Deep inside of mmm-me.”

Flake exhales harshly in exasperation at himself. He could barely get that out, he’s so flustered and embarrassed. Richard grins. He leans in to kiss over Flake’s forehead and blushing cheeks. Flake huffs. Gently, Richard lowers Flake’s legs; Flake naturally closes them around his waist, feet hooking over his thighs. Richard’s heart is fluttering with love and excitement and relief—he’s so glad it worked out. He speaks lowly, voice thick.

“Wrap your arms around me,” he murmurs, “If you want.”

Nodding, Flake immediately reaches up to do just that: he slips his arms under Richard’s, to wind them around his back, hands flatly roaming along soft, supple skin. Flake hums softly in his throat. Richard swoons. He nuzzles into Flake’s messy hair and sighs.

“I love you,” he mumbles. Flake is silent. He hides in Richard’s neck, tightening his arms around him. He holds him snugly. Richard is fine with waiting for the reciprocal statement. Flake doesn’t have to say it—he’s told him that before, too. Flake nods against him. Richard glows with warmth and adoration. It’s always been easy for Richard to say that. He always means it. Romantic, or not. Love is simpler to him, more than it is for a lot of people. He’s not afraid to express it.

Refocusing, Richard pulls back just to monitor what’s going on down there. And to maintain a better angle for Flake’s pleasure. Flake keeps his legs wrapped around him, modestly. Richard rests one hand upon Flake’s flat belly, damp with sweat. Reaching back, he plants the other behind himself, against the bed for stability. It has him leaning back, just enough to obtain a nice visual of his cock sitting inside of the other man. Arms extended, Flake’s hands end up on Richard’s thighs, holding him there firmly.

Richard begins carefully moving his hips. Flake grunts. Richard feels him begin to bear down again, to make the glide smoother. Grinning, Richard peeks up to watch his face as he slowly thrust his cock in and out of him, just a couple inches at a time, with a graceful, fluid rolling of his hips.

“Oh—Richard—!” Flake exclaims softly, head falling back into the pillows, his mid-length hair splaying out, some locks clinging to his neck and jaw with sweat. Richard is relieved it feels good for him—at least, it seems so. Flake’s nails are digging into his thighs now. Clutching at him. The bed is creaking quietly as Richard moved. He doesn’t speed up. He maintains this careful rocking of his hips, eyes downcast to watch himself thrust into him, admiring the sight of his shaft pumping into him again and again.

Richard stops moving, if only to shift closer, reaching out to hook both arms around Flake’s lean thighs and pull him closer, across the sheets. Flake looks up at him with wide eyes, flushed cheeks, and a broadening smile. Cute—Richard can’t help but grin in return. Readjusting on his knees, he hugs Flake’s legs to himself, hands splayed over his thighs, and begins gently pumping his hips against him once more.

“So good, babe,” Richard moans softly, stroking his hands up and down along his lean thighs, fingers tickled by Flake’s fair hair, “Feels really good... Does it feel good for you? What’s going on, tell me. Does it still feel weird?”

“No—“ Flake grits out, and then pauses, only to exhale harshly a moment later with a tense expression, his brow knit and mouth open. Then he swallows hard and tries to speak again, amongst Richard’s careful, slight thrusts.

“It—it feels—good…? Nnn, I don’t kno—know. It doesn’t hurt. Oh, God.”

He drops his head back down against the pillows. Richard chuckles. He shifts, moving so he’s hovering over Flake with both hands planted upon the bed. He watches his face as he began rocking into him with a bit more speed, in slightly deeper thrusts. Flake moans aloud at that, closing his legs tightly around his waist. His throat visibly works when he swallows, his Adam’s apple bobbing when he speaks in a slur.

“That’s good,” he groans, “Deeper…”

Richard exhales long and slow, shakily. His belly is a smoldering cauldron of arousal. His cock is so fucking hard, and his balls are aching. He’s not going to last much longer. But he wants to make Flake feel really good.

“Nngh, wait,” he bursts out breathlessly, “I want to try another position. Get on your belly.”

Then he slowly, carefully slides out, until his cock pops out of him with a wet, slick slide that has Flake shuddering hard, legs clenching around his waist. Unraveling his legs from around the other man, Flake dazedly rises to turn over. Richard shifts out of the way, attempting to catch his breath, chest heaving. Flake’s pale skin is glistening with sweat. Droplets roll down his flat chest, following the ridges of his rib cage. Beading on his belly decorated with moles. Richard tracks him, admiring Flake’s lean, skinny body as he sluggishly moved. His cock is long and hard, heavy, trapped between his thighs as he settles on his belly among their rumpled sheets. Richard reaches in to pet at it as he shifts closer, kneeling behind him. Flake jerks, and laughs.

“Pretty,” Richard teases quietly. Flake chuckles again, hiding his face in his elbow. Richard tickles at the head, earning a lurch of his legs and an exclaimed noise of protest. Richard laughs and moves into position. He gets on top of him, their legs sliding together, aligned. It feels nice. Flake grumbles in quiet enjoyment. Flake’s skin is hot and slick against his own. Richard roams both hands along his back. It’s quite a pretty display. Smooth, pale, with a few moles that Richard has kissed many times.

“Relax,” Richard murmurs, lovingly trailing his nails up and down across his back, “Always focus on relaxing. Don’t tense up.”

Flake nods into his arm. Richard is more confident now as he shifts higher up over his body, to align their lower halves. He rises up on a knee, hand propped against the bed, and grips his cock with the other to sweep it down between those cute little asscheeks. Flake moans weakly into his elbow, muffled. Richard exhales long and slow—it’s hard to keep a right mind during this. Flake is so beautiful and sexy. He could just absolutely go to town on him, but that will have to wait until later, when Flake is much more accustomed to this.

Instead, Richard carefully rubs the head back and forth against his slickened hole and begins to slowly, slowly, sink inside while Flake bears down, which in turn, has his body opening up more. Richard can slide in smoothly, evoking a sharp groan from Flake. It feels so good, but Richard really has to focus on not hurting him. Penetrating him too deeply at too fast a pace can be overwhelming. Only after gradually pushing in to the base, can Richard rest upon him with his full weight, pinning him to the bed. Flake is openly moaning with a breathless burst of air from his lungs. His legs are tensed and quivering against Richard’s. Richard rests his front against him, his soft belly dusted with hair pressed to his back, his pecs smothered to his shoulder blades. Flake jerks a hand down to rest it against Richard’s thigh.

“This is better,” Flake says shakily, “I like… I like it when you’re on top of me.”

“Me too, babe,” Richard murmurs, “Love having you under me, pinned to the bed. Could have my way with you.”

He leans in to nuzzle into his ear and the back of his head, only to kiss his neck. Flake makes a flustered noise. Richard slowly, gently circles his hips, working his cock in him, balls deep. Flake lurches, and groans sharply.

“Richard,” he gasps, “Oh, God!”

Richard nuzzles into his soft hair while he resumes grinding into him, carefully, watching for any signs of pain, listening for groans of discomfort. Flake does exclaim, a sharp sound that ends with a laugh and then a weak moan of pleasure when Richard firmly rolls his hips against him again. Richard grins, pleased to hear it. Pausing, he takes a moment to wrap his arms around Flake’s chest, braced on his elbows, hands curling up around Flake’s collarbone and shoulders. He holds him as he begins pumping down against him. Quicker, deeper thrusts. Gentle, but also intense in the way they deliver pleasure. That has Flake’s head lifting, with a hard exclamation of what Richard hopes to be pleasure.

“Oh!” is all Flake manages to say, sliding his legs further apart, “Oh, yes! Like that!”

Okay, pleasure, then. Good. Richard is huffing against Flake’s neck as he begins to fall apart. It’s too good—and hearing Flake enjoy it makes it all the better. He must be striking Flake’s prostate, as he anticipated, considering Flake is crying out following every thrust. He’s shuddering during the withdrawal, probably due to the drag of his shaft along the sensitive rim of his asshole, and then groaning with evident pleasure when Richard slides back in.

For a minute, Richard maintains these long, slow back and forths, only to resume the harder, faster thrusts that really seem to drive him crazy. Flake is whimpering and groaning and shuddering amongst them, and in turn, it just edges Richard on. By this point, Richard is shaking uncontrollably himself, his face in a grimace of pleasure. He’s sweating so much, and this intertwined position with Flake only worsens it.

“Feels good?” Richard grits out breathlessly, quickly pumping his hips despite the burn in his thighs. The soft clap of his pelvis hitting against Flake’s ass, accompanied by Flake’s exclamations of pleasure, only heightens his own state of arousal, of debauchery. He wants to do so much more, but he can only go so far, for Flake’s sake. Flake just manages to suck in a lungful of air before replying sharply, “Yes! D-Don’t stop!”

Well, it seems he doesn’t have much of a choice, really, because his body is reaching its limits. The roaring flame of his devouring orgasm is consuming him, whether he wants to prolong the sex or not. Richard’s thrusting becomes jarring, and spasmodic.

“Going—going to come, baby, sorry—” Richard grits out, “Shit—”

He has to hold himself back from pounding Flake into the bed. He slows to a stuttering stop, heaving and grunting and gasping for air. He shakily pumps into him a few more times, trembling wildly. Flake is moaning loudly, and shoving his hips back into it. It makes for deeper penetration while Richard ruts into him quick and fast, balls hitting against him lewdly. Flake is unashamedly enjoying it, curling his legs back over Richard’s, as if he could possibly pull him closer.

“Oh, fuck,” Richard moans lowly, “I’m coming in you, fuck, sorry—I can’t—Don’t want to pull out.”

Flake’s moans have weakened now, to soft sounds of pleasure. He’s still pushing back into it, breathing harshly into his arm. Flake then speaks, murmuring shyly, “C... Come in me. It’s okay. Feels s’good.”

That has Richard groaning with force, just as he’s swept away by the intensity of his powerful orgasm. He squeezes his arms around Flake’s chest, nuzzling his face into him. He snaps his hips against him twice, hard. Flake grunts sharply with each one, his hand pushing back against Richard’s thigh. Richard, in the haze of his orgasm, realizes his mistake and gasps out a harsh exhale of s-sorry, and simply resumes his short, little thrusts, stimulating his aching cock just a bit more inside of Flake as he filled him with his cum. Flake is moaning so genuinely, Richard, in his hazy state, finds himself incredibly pleased he could evoke that from him.

And then Richard slowly, reluctantly slides out of him with a low, deep exhale. Flake goes limp against the pillows. Kneeling back between his spread legs, Richard gropes two handfuls of his cute ass and spreads him open. His hole is well-fucked and dripping with his cum now. Richard bites his lip, amazed. He stares a moment longer, while Flake pants into the bed. Richard assumes he’s embarrassing him by doing this, so he leaves it be. He scoots back just a bit, if only to reach in, grab his leaking cock from the sheets, and angle it up from between his thighs, leaning in to suck it into his mouth. Flake lurches, and laughs.

“Richard! Let me—flip over—ngh!” he gasps out, but ends up collapsing against the pillows regardless. Richard agrees; he wants to see him. So he stops, and then sits back, tucking a hand under a sweaty, skinny thigh to gently pull upwards. Flake sluggishly turns over, careful to avoid kicking him. Richard gives him a warm smile, watching him limply fall back against the pillows with a sigh. Sweeping his longer hair back, Flake gives him a dazed look. His chest is heaving, blotched in places with red. His skin is dripping with sweat. He looks delicious. Richard crawls over him, between his lazily spread legs, and kisses his brow firmly. Flake runs his hands up over his back, fingers splayed to soak up as much contact as possible. Richard’s long locks, now made messy from the exertion of sex, fall to tickle Flake’s face when he kisses him.

It doesn’t last long—a few weak purses, and then Flake turns his head out of it with a grunt. Richard pulls back to see him scrubbing at his lips with a wrist.

“Sorry. My mouth tastes funny,” Flake mumbles. Richard pauses, and then laughs.

“Okay, jeez. I’ll just suck your dick, then.”

Flake blushes, heavily. He nods a little, pauses momentarily, and then reaches up to brush Richard's dark hair back from his forehead, fingertips sickeningly gentle. It has Richard grinning broadly, eyes glimmering with fondness. Flake swoons, seeing this. Then Richard shifts further back on the bed, kissing as he descends. Mouthing at Flake’s flat, heaving belly, licking up droplets of sweat, appreciating every little mole with a soft peck. He nips at Flake’s bony little hips, and bites gently at his pretty thighs. Flake is watching patiently, his breathing hard, but controlled. Richard finally grabs that lovely, sizeable cock and angles it up. He admires it. The way his foreskin is slightly folded over the pinkened head, the slit swelling with pre-cum.

Smiling, Richard shifts a little closer, comfortably tucking his arm over Flake’s thigh, elbow planted upon the bed, chest smothered against his leg. He then leans in to lick at the tip with a mischievous glance towards Flake’s face. He loves the taste of him. Flake rises up on his elbows to watch, his mouth fallen open, eyes weak.

Richard delicately closes his mouth around the head, and sucks lightly. Simply nursing at him. Flake moans, a shaky little sound that is simply adorable—it’s hard for Richard to find another word to describe his noises. He gradually works more and more into his mouth. Deeper and deeper, maintaining tight suction, until he’s got a mouthful and Flake is shuddering underneath him, sucking in sharp breaths and grunting quietly. Richard has his manicured fingers wrapped loosely around the base, keeping it steady as he carefully eases the rest into his mouth, letting it slide past the cusp of his throat into places that aren’t exactly comfortable. But he bears it, with a furrowed brow, just to hear Flake moan aloud. He jerks a hand up to grasp at Richard’s hair. Richard pulls off slowly, flicking heated eyes up to Flake’s, and then goes back down on him again, until he’s entirely in his throat and his lips meet his fingers. Flake is huffing noisily. Richard decides to stop messing around.

He begins bobbing his head, sucking harshly while bringing his other hand in to gently grab his balls and knead them in his fingers. Flake’s legs jolt from that. Richard knows having his balls massaged while getting sucked off, or even while he’s fucking, drives him crazy. Flake seems to agree. Without much warning, as Richard moves his mouth over half of his cock, he feels it throb and strain against his tongue. And then semen floods his mouth, while Flake collapses back against the pillows and gasps harshly for air. His legs are trembling. Richard furrows his brow. He’s not opposed to getting a mouthful of spunk, but he appreciates some kind of warning beforehand. He continues sucking at him, slowly stroking at what isn’t in his mouth with tight fingers.

“Richard,” Flake moans, that hand in his hair roaming further back to cup the base of his head. Richard swallows what’s in his mouth, and then resumes sucking in long, slow pulls while working his hand over his slick shaft. Flake’s balls are tight in his hand. He continues gently kneading them in his fingers. Only after Flake gently pulls at his hair, murmuring about sensitivity, does he finally stop. He pulls off slowly, sucking as he withdraws, before lifting his head and licking his lips, looking at the other man with a smile.

“What’d you think?” he asks, moving to get up. He crawls over him. Flake looks up at the other man with wide, bashful eyes and pink cheeks. Grinning slyly, Richard carefully moves to lay beside him on the bed, keeping his legs tangled amongst his. He gathers the skinnier man into his arms, impatiently ignoring his flustered squawk and nervous squirm. Richard holds him tightly, affectionately. He begins stroking at his back. Flake ends up with his cheek to his chest, long limbs curled up.

“Um, you’re still very good at oral,” Flake murmurs, “That hasn’t changed.”

Richard laughs aloud. He brings one hand up to pet at his boyfriend’s hair.

“I meant the anal, silly. It was your first time.”

“Oh,” Flake mumbles, and Richard can hear the blush in his voice. Flake lazily drapes his arm around Richard’s side.

“It was… Interesting. It felt weird, but the pleasant undertones coupled with the occasional spark of pain made for an intense sensation.”

Richard hums, contemplative.

“Did it feel better after we switched positions? It’s easier to hit your prostate when you’re on your belly.”

Flake pauses, thoughtfully.

“Actually, yes. When I was on my back, you did poke around a bit at places that just felt weird, and the pleasure of it didn’t really distract me from the odd sensation.”

“But you still enjoyed it, weird feeling and all? When you were on your front?”

Flake huffs. He wiggles closer just slightly, nuzzling into Richard’s muscular chest and the soft, subtle layer of hair found there. He speaks in a low mumble.

“Of course I did. Sex, even when it’s not amazing, is more tolerable with you. It might even be enjoyable, despite it taking a lot of work. Especially anal. Takes too long to prepare for it.”

“I’m… Glad?”

Richard isn’t sure what to make of that. Flake laughs.

“I like this part the best,” he admits a bit boldly, “Cuddling is nice. You tolerate my bony parts.”

That earns a smile from Richard.

“I love your bony parts. All of them.”

“…Was that a dick joke?”


“Okay, just wanted to make sure. It was a good one.”

Grinning now, Richard tucks his chin to kiss Flake on the top of his head, tightening his arm around him. Flake sighs and wiggles closer, until their fronts are snug together, legs overlapping, his face now tucked into Richard’s neck. Richard closes his eyes. This is very comfortable. He could sleep like this, with Flake nestled into him. Why doesn’t he?

The way Flake goes absolutely limp against him, breathing slow and easy, arm draped contentedly around him, convinces him he has the same idea.