#the only part i don't agree with is 'you don't feel jealous per se' because he ABSOLUTELY FEELS JEALOUSY OF EVERYBODY WHO HAS HIS DESIRES | Explore Tumblr Posts and Blogs

wincest-gaychesters · 4 years

Note

Hey, it's me again!♡ :3 I hope I don't annoy you with my ideas? So, I don't know what you think of Jack, but I love him! And I think it would be great if Sammy and Dean, Jack teach something more about sex. It may sound a bit perverse, but I think, our boys would be very loving and gentle with Jack. And I think this three would be so hot and somehow unique! What do you think? ^^ Love for you💕

I finally finished this one! I’m sorry it took so long, it’s a lot of firsts for me (Jack, threesome) so it took me a while to write it out, but it’s finally here!!

I know we talked a little more about it and I hope it ticks the boxes you were looking for!!

Will be under the cut: Their super innocent new roommate is trying to learn all about life and asks, oddly specifically, about sex. Dean, who's started to think the kid's adorable, agrees only because Sam, who's already a little in love with the boy, talks him into it. Established relationship between Sam and Dean, rimming, fingering, blow jobs, first time for Jack, dirty talk, very pwp ;)

Jack had asked, with absolute zero shame, what sex was like. It had taken Sam by surprise and, at the time, he thought it was because he was experiencing a first crush. On who, Sam couldn't bear to think of it. Dean was the one who answered, of course, talking about his porn collection and how that would set Jack upright.

Sam didn't like the idea, but it seemed the easiest way to open up the conversation, so he reluctantly agreed. They were a few minutes in, a video not at all to Dean's liking playing, the two people on-screen kissing and starting to undress when Jack had stopped it. With his unnerving directness, he told them, possibly, the best thing Sam's ever heard. That he wanted to know what sex was like between guys. And in answer to Dean's dumbfounded face, he put the final nail in their coffin, "I wanna know what it would be like with you."

Getting Dean to agree was a struggle. In fact, it's been a few days between then and now, and Sam nearly had to bribe him. Even now he can feel how uncomfortable Dean is with this, the jealous bastard.

For his part, Dean's not against this, per se. He's just not that into it. Jack is cute, he'll admit, but Sam is his and he's not real big into sharing. Not to mention, he's seen the way Sam looks at Jack and no matter what he says, he's clearly into the boy.

Which is how they end up here, Dean's arms wrapped possessively around Sam, waiting, expectantly, for Jack to walk into the room.

When he does, Jack greets them a little hesitantly, but otherwise as bright as usual. Sam smiles at him, one of those huffy little smiles Dean loves, and he growls in his ear because it's so obvious Sam's into the boy. And, maybe just to spite Dean, he can't be sure, Sam pulls Jack into a kiss.

Sam lures him in with an outstretched hand, the other coming up around Jack's waist when the boy takes it, and in the same motion pulls him in. Jack stiffens, pure surprise, but then goes limp in his arms and all he can really think about is Dean opening the boy up. So he pulls back, drops a soft kiss on his cheek, and turns to Dean.

Dean's face is frozen in a scowl and Sam has to maneuver in his arms to reach his lips. But when they finally meet it's rough, Dean growling and biting, as adorable as it is annoying. Sam goes along with it, fighting back, before pulling away and taking advantage of Dean's momentary daze to push him and Jack together.

It's weird, the pliable boy under him, and Dean instinctively moves his hands up to grip his hair, adjusting them into a better angle, tongue darting out to lick along Jack's bottom lip. He reacts with a soft little gasp, mouth opening just a bit and Dean takes advantage of it, thrusts his tongue in more roughly than he meant to, and gets lost in the game.

Sam moans somewhere next to them and he has to pull away, breathing heavy. "Knew you'd like him," Sam whispers, one hand still laying on Jack's waist, the other coming up to rest on Dean's cheek.

Dean looks up at him, unreadable, before nodding and impatiently trying to shove them both toward the bed. They're in Sam's room because Dean's a stubborn bastard and of course he was never gonna let anything happen in his bed. But that's ok because Sam can't wait to have the smell of both of them mingled into his sheets.

Dean sits them on the bed, taking Sam's lips again, hands smoothing over his chest, slowly teasing until Sam's moaning into him. He keeps sucking the noises out of Sam, hand reaching blindly until he finds Jack's, guiding it down over Sam's half-hard dick, trapped under too many layers of clothes. Jack gasps again, something that sounds like a perfect oh escaping his lips. When Dean moves their hands, pressing and rubbing against Sam, the boy picks it up quickly and Dean abandons him there, his own hands coming back up to Sam's chest, moving to unbutton his shirt.

Dean is down to the last two buttons when Sam's head falls back, keening, hips pushing up into Jack's hand. Dean can't help the chuckle that escapes him, "like that, Sammy?" And Sam's answer is a deep groan, eyes blinking open slowly before pushing himself up, grabbing Jack's arm and pushing it away. "Did I do something wrong?" Jack asks, in that oh so innocent voice of his, looking guiltily between them.

"Jack, no! No, no, no." Sam gets out, breathing heavy, "no, it's just..."

"Sam doesn't want to come too soon." Dean leers, and Sam can hear the smug smile.

"Shut up," he shoves at Dean's face before turning fully to Jack, unbuttoning the last of his shirt and throwing it off.

"C'mere," Sam takes Jack's arms and wraps them around his waist, pulling his face up to catch him in another kiss, and he just knew it was a good idea to get Dean to kiss him first, because this time Jack opens his mouth to him, unprompted. He kisses the boy slow and deep, taking his time drawing out the moans, letting them build up, louder and louder.

He forgets all about Dean until his brother groans, loud and clearly annoyed, but doesn't draw back right away. Sam likes pushing Dean's buttons, likes what happens when he gets jealous, and he can't wait for that anger to be directed at him and Jack. When he finally does let go of Jack, the younger boy's eyes glazed and breathing hard, he's surprised to look over and find Dean naked already, stroking himself, watching them with a mix of hunger and frustration.

Sam smiles wickedly, peppering soft kisses over Jack's cheek without breaking eye contact with Dean, "enjoying the show, Dean? You're so hard already." His eyes move slowly down his brother's body and Dean makes another frustrated sound.

"Undress, now." He nods curtly at Sam before manhandling Jack out of his arms and kissing him, pushing him back to lay on the bed.

Sam gets Dean's frustration now, it's such a hot scene, honestly, Dean's hands all over Jack in a way Sam knows all too well, the younger boy helpless under him. Sam stands up to rid himself of the rest of his clothes as quickly as possible before laying out on the bed next to them.

Feeling the dip of the bed, Dean looks over at him and grins, moving off to the side, almost completely off the bed, one foot steadied against the floor, leaving Sam access to Jack. Then Dean leans back down to take Jack's mouth, the angle forcing Jack's head back into an awkward position, though he doesn't seem to notice. And Sam gets down to work, undressing Jack slow and teasing, leaving a trail of kisses after every inch of skin he uncovers.

He pushes Jack's shirt up as far as he can without breaking Dean's deep kiss, leaving it bunched up under the boy's armpits before focusing his attention on Jack's uncovered nipples, mouth coming down to suck one in, letting his hand wander over to pinch the other. Jack's hips buck up at the contact and Sam hums happily into his skin. He licks it stiff, then pulls up for a second, about to move over to Jack's other nipple, when he catches them both watching, Jack teary-eyed and in awe, Dean with dark and narrowed eyes.

"He must taste really good." Dean rasps, and Sam can't tell if he's jealous or turned on, maybe both.

"He does," but he directs it at Jack, eyes connecting, and Jack shivers in response. Sam smiles at that, sweet and dirty, before going back to his earlier task, latching onto Jack's other nipple, making the boy shiver again. His hands gently find their way to Jack's pants and he continues to undress him.

Dean could watch Sam forever, he thought he'd only ever want Sam's attention on him, but watching his brother slowly pull apart the boy under him is just as amazing. He turns to Jack, then, watching as his eyes shut tight against Sam's mouth and hands, as his own hands clench uselessly in the sheets. And, yeah, ok, so he kind of understands Sam's obsession with him. Dean lays a soft kiss against Jack's jaw, letting his lips drop further down next to the boy's ear.

"You like that? Sam's mouth all over you?" And the reaction is perfect, Jack shuddering and moaning out. "Yeah, I know, Sam acts all nice and sweet," he shifts until his brother comes into view, "but his mouth is pure sin." Dean knows Sam can hear him, though he gives no indication of it. "Sammy's a total slut."

Sam finally pops off, looking up at them both, sending Dean a half-hearted glare. And, of course, Dean just laughs at him, low and dark.

"You're one to talk." He tries, but Dean's smile doesn't waver.

Jack looks up at Sam, then, and in an absolutely serious voice asks, "what is a slut?"

Dean laughs, and Sam gapes at him, not really sure how to answer. Before he can think of anything, Dean pulls Jack's attention to him with a light finger to the chin, "don't worry, we'll teach you." Then he lays another deep kiss into his open mouth.

It's one of the best things Sam has ever seen and, getting impatient, he moves down to quickly finish pulling Jack's pants off. He can hear the whimper clearly, even with Dean swallowing the noise.

Dean pulls back and looks down, eyes skimming appreciatively over Jack's mostly naked form, "about time."

"Oh yeah, you really hated waiting." Sam rolls his eyes.

"Not hated," he replies, sitting Jack up and helping him out of his t-shirt. "But we could definitely speed things up." He stands up and drops the shirt on the ground next to him.

Sam understands, he's getting impatient too, Jack just sitting there, willing to take whatever they throw at him, and god there's so much he wants to do. So he nods, an idea occurring to him, and instructs Jack to get down on the floor with him, kneeling side by side at the foot of the bed. He shoots a suggestive look over at Dean and waits for him to catch up.

When he figures it out, Dean doesn't waste time coming over and, in one practiced motion, slides his cock into Sam's waiting mouth. It's a perfect feeling and he sighs into it, enjoying it momentarily before pulling back, slowly sliding back in. Sam hums around him, sending a shiver up his spine, and Dean thrusts into him, hard.

Sam moans, letting it happen once, twice more before taking hold of Dean's hips and pushing him back. Dean groans in response but Sam ignores him, looking over at Jack, instead, and finds the boy watching them intently.

Sam smiles when their eyes connect, cupping the boy's chin, "you wanna try, Jack?"

"Yes." It's a whisper, but it's clear, Jack looking up at Dean.

Dean grins, suddenly predatory, and moves to stand in front of Jack, a hand coming down to stroke his cheek. "You really think he's ready, Sammy?"

"No. But do you care?" Sam kisses the words into Jack's skin, hand moving over his throat, and Dean groans again at the sight of them.

"Open your mouth, sweetheart." Sam whispers and Jack obeys.

It really is a gorgeous sight, Jack open and waiting, Sam kissing nonsense into the kid's cheek. Dean grabs himself and tries to remember how to be gentle, slowly feeding his dick into Jack's small, wet mouth. He's pushed half his length in, knows Jack won't be able to take too much more, when the boy's throat seizes violently, coughing around him.

Dean pulls out instinctively and lets Sam ease the boy through the gagging. Jack recovers quickly enough but Dean doesn't expect the teary-eyed apology directed at him, and his heart clenches. Yeah, he might be falling in love.

Sam draws Jack's attention away, gives him a quick and dirty kiss, "relax and breathe, baby." Taps his nose lightly before posing him for Dean again.

Dean tries to smile reassuringly at Jack before pushing the tip of his cock back into his mouth, letting it rest there.

"Suck," Sam whispers into the boy's ear, reading Dean's mind, and the shy pull Jack gives him takes his breath away. He slides his hand into Jack's hair and slowly pushes further in. With Sam encouraging the boy, trying to keep him relaxed, Dean finds the back of his throat, making them both moan.

Sam's hands are rubbing along Jack's jaw, hoping it helps in some way, but it's hard to concentrate with this view. His mind keeps filling in with the memory of Dean, his taste and his weight, and Sam has to force himself to focus on Jack. But the faces Jack is making, the little noises, Sam could watch it all day. When Dean seems to push as far in as he can, Sam can't help himself, whispers to the boy, "suck again, Jack. Hard as you can."

Dean groans above, deep and breathless, falling forward, barely holding himself up with a hand on the bed. Sam smiles but wants more, moves Jack's head back, sweet reminders to breathe, stay relaxed. The shift allows Jack's throat to open up, Dean slipping further down and when Sam's hand slides over Jack's throat, he can feel it. Feels it when Dean starts moving, fucking down slow and deep.

Dean's eyes are shut tight, forcing himself to go slow, but his world is quickly reducing to Jack's tight throat, losing control with every inch he gives. Before he knows it he gives a shallow, quick thrust, feels Jack strain around him, and can't stop himself from thrusting again. Hard, over and over, Jack's throat convulsing around him until, suddenly, he's coming.

Sam is staring, hungrily taking in the scene, swallowing heavy before talking Jack through it. He's got his hands on the boy, keeping him in place, whispering to him to swallow, to keep breathing. And Jack does such a good job, Sam makes sure he knows it but he's barely getting the words out, finding it hard to breathe, impatiently waiting for Dean to pull out. When his brother finally does, Sam pulls Jack into a kiss, chasing after Dean's taste.

Jack is gasping, eyes closed, throws his head back against the bed when Sam finally lets him go. Dean is on Jack's other side, facing them both but breathing just as heavy. Their eyes meet and Dean reaches his hand out to him, an invitation Sam doesn't hesitate to take.

It's an awkward position, Sam on all fours in front of Dean, but he can't wait to have that mouth on his and he leans in impatiently. He can taste Dean's laugh as their lips meet, easily opening up to his brother when his tongue darts out, melting a little into the languid kiss.

"You're gonna love him," Dean whispers as they pull away.

Sam nods before taking Jack and moving him up to the bed, laying him out again.

"Don't worry," he whispers to him, "we'll take care of you." But he's been watching and waiting for so long, Sam can't wait anymore and kneels over Jack's face, sliding into his mouth slowly.

Sam closes his eyes, Jack's throat tight around him, and he can feel the younger man trying to control his gag reflex, trying to breathe through it. A weird mixture of pride and lust wash over him and he starts fucking into Jack, easy but as deep as he can, pushing further in each time.

Dean smiles at them, loves how Sam takes control of the boy so easily, but he knows what Sam expects of him and he leans down to kiss the tip of Jack's dripping cock. Sam moans and he can only imagine what Jack's reaction was, can still remember the feeling of the boy's throat tightening around him, and his dick stirs in interest.

Dean leans back down then, wonders for a moment if he should try and draw this out, decides against it, and swallows Jack down in one go. This time he hears the deep groan, Jack's skinny hips bucking up hard and all Dean does is swallow around him, letting his tongue play over the boy's length.

Sam is moaning too, unable to control himself, his hips thrusting hard into Jack's mouth and the boy under him is squirming, gagging and groaning. It's tight and every time Jack swallows it tightens more, and Sam is coming not long after, thrusts deep, and screams out.

Dean can feel it in the way Jack thrusts up into him, and he doesn't hold the boy down, lets his chaotic rhythm take over. A few licks and sucks after Sam comes and Jack is spilling his seed down Dean's throat, and he can't help but swallow it all down, greedy for it. He gives Jack's cock a few more sucks and licks him clean before pulling away.

Sam is resting, spread out on the bed next to Jack, watching and waiting for Dean to finish. When his brother pops off, he gestures with a finger for him to come up. Dean obeys, moves onto the bed, and, like he can read Sam's mind, comes straight in for a kiss. Sam already can't get enough, the mingled taste of Dean and Jack, and he sucks as much of it as he can from Dean's mouth.

They pull away slowly, kisses turning soft and lazy, and Sam reaches down to grab Dean's half-hard dick. His brother gasps in surprise but leans into it, letting Sam stroke him to full mast.

Jack stirs next to them, sitting up and boldly dropping a kiss to Dean's shoulder, looking up shyly when Dean turns green eyes to him. Without much thought, he pulls Jack up to a kiss and it doesn't take long before he grabs Sam's wrist, stopping him mid stroke.

Panting a little he pulls away from Jack and whispers, "not yet, Sammy."

Another time Sam might poke fun at him but, today, he understands. Today, Sam just wants to keep things moving, to get Jack back under them and squirming. So, instead, he pulls Dean to him and whispers his intention. Dean grins wildly and they both move to the edges of the bed. Sam, in the soft voice he's been using all night, gently guides Jack to lay face down in the middle of the bed. And Jack, in that way of his that screams he would trust Sam to his dying day, easily follows and lays still, waiting.

As always, Sam lets his brother go first. Stays up by Jack's head and kisses his cheek, his shoulder, anything he can reach, while murmuring little encouragements and platitudes. Dean, no longer patient, drops his head between Jack's legs and licks a long stripe from his balls to the top of his ass. The younger boy keens and Dean does it again.

Dean smiles into it, he can clearly remember his first time with Sam, how desperate it was, but with Jack it's different. He doubts the boy can handle what Sam can handle, and the hunger that used to gnaw at him for Sam isn't there for Jack. He doesn't feel the need to force hidden feelings into every action, to make every touch a wordless speech of everything he'd like to say but can't.

No, with Jack he has to take his time, open him up slowly. The boy is sensitive, first time, probably hasn't even touched himself before, and Dean has to work with that, has to be gentle with him. But Dean is good at slow, ducks back down to kiss lightly at Jack's hole, making him shiver. Then he presses his tongue against it, licks until he has a clear memory of the taste.

Sam is rubbing Jack's shoulders, kneading softly in hopes that it adds to the pleasure. He's watching Dean lick and suck, leaving wet trails all over Jack's ass, pooling saliva over the little pucker. He can't look away, thrills every time he sees Dean's tongue glide over Jack's hole, loves how it makes the boy under him squirm and moan. Then, before he ever pushes into the boy, Dean looks up at Sam. An understanding passes between them and Sam moves down to join his brother.

At first, he just stares at Jack, reverent, worshiping, then he bends down and licks carefully over his hole. Jack whimpers. A soft, lovely sound that Sam wants to hear again, so he gives him another lick, identical to the last, and another, and another. When he pulls away, Jack is sobbing softly, hands gripping the sheets.

Dean takes his place, tongue back to work, at the same time that Sam asks, "does it feel good, Jack?" All the boy can do is nod.

Jack shivers under Dean, body flushed and sweat-sticky, then, suddenly, he gasps loudly, whole body tensing up. Sam can't see it, but he knows Dean's tongue has finally squirmed its way into Jack. Dean pulls a few more moans from the boy before pulling back.

Sam waits for Jack to stop shaking, for his breath to even out, before diving straight toward Jack's hole, mouth latching on. He licks over it once before forcing the tip of his tongue into the tight hole. Jack goes rigid for a second, then he sighs, relaxes, and his hips push a little closer to Sam.

Sam moans lightly, appreciative, before trying to wiggle his tongue a little deeper. Each attempt makes Jack quiver and, before long, the boy is a whimpering mess again.

When Sam finally pulls away Jack doesn't even turn to look, knuckles white in the sheets.

Sam moves him again, gets him up into a kneeling position that exposes him, and presents his ass up, like an offering, to Dean. And his brother wastes no time taking it, licking his way back in.

They keep taking turns, slowly eating the boy out, keeping him on edge. Jack, soft and pliable, shivers and moans at every touch, at every little wriggle of their tongues, and soon he's mumbling, too, begging for something he can't even understand. They both pull away then, Sam shushing the boy with gentle kisses.

"Please, what? What do you want, Jack?" Dean asks before dropping a kiss to the dip of his lower back.

A shiver runs through him again, then turns wet eyes to Sam. "I don't know," it comes out in a strangled little sob.

"Something bigger," Sam says but Jack doesn't seem to understand. "What you want, baby. You want more, something bigger."

Jack continues to stare up at him, totally lost, so Sam tries again. "Please, Dean, I want more. Need something bigger." And, this time, Jack repeats it.

Dean chuckles a little darkly as he straightens up and goes to the bedside table. "Ok, Jack, anything you want."

When he returns it's with a bottle of lube that he squeezes over Jack's ass, letting it run. Jack squeaks at that and tries to look over.

"It's to help you," Dean says, looking at him before squeezing a decent amount into his palm, making a show of covering his fingers in it. "So it hurts less."

Dean wiggles his fingers, winks, then drops back behind Jack, rubbing the lube over his hole before trying to push his index into him. Jack makes a surprised sound, but Dean keeps pressing until the tip of his finger is swallowed, caught in the tight heat.

"Relax for me, Jack. It'll feel better." Dean calls while rubbing circles into his skin with his other hand.

Sam takes over then, softly instructing Jack to relax again before taking his lips in a kiss. Hoping to distract the boy a little.

Dean takes advantage of it, Jack just a little looser than before, and gets his finger all the way in. And the boy is moaning over and over, muffled by Sam, but still beautiful. Dean flexes his finger, deep inside Jack, and the boy gives a perfect, open-mouthed moan. Smiling, Dean does it again, and a few more times until Jack is shaking under him.

Dean looks up, locks eyes with Sam, "that's just one finger, Sammy."

Sam groans before coming to join Dean again. He spreads lube on his fingers quickly, impatient, then rubs along Jack's hole, right where it's pressed tight around Dean's finger. Jack whimpers a little and Sam reminds him to relax, waits until his breathing steadies a little before trying to push his own finger in next to Dean's.

This time Jack screams. Sam has to shush him, peppers little kisses where he can reach, and waits patiently for Jack to say he can take more. But it doesn't come and Sam remembers so late that the boy is new to all this.

"You have to tell me when you're ready, baby."

"Oh," Jack nods shakily, looking over his shoulder at them. "I'm ready, Sam." He whispers.

Sam holds back a strangled sound, then pushes deeper until his finger is right next to Dean's. He wiggles it a little and Jack sighs, head falling onto the pillows. Then they move their fingers together, in and out, taking turns with it, tugging at the rim, trying to open him up. When Jack is whimpering again, whole body shaking, they pull out. Sam has every intention of heading back up to Jack, kissing him until he can't breathe, but Dean has a better idea, has him kneel alongside the boy.

Dean doesn't rush it, even though Sam's always impatient, but he carefully fits three fingers into Jack, waits until he's pushed all the way in before turning his attention to his brother. Sam is trying to watch him over his shoulder, tracking his movement as Dean bows down and, without any hesitation, lets his tongue push into Sam's ass. And his brother moans out, Dean knowing exactly what Sam likes.

It's a balancing act, fingers deep in Jack, tongue working in Sam, but he manages to keep them both on edge. A weird sort of satisfaction swells in Dean at knowing he can have both his boys like this. At knowing he's the one that's giving them this pleasure. He pushes them until Jack is mumbling things again and Sam is moaning his name, pulls back breathless, making them both groan at the loss.

Sam rolls onto his back and eases Jack down next to him. "Did it feel good, Jack?" Sam asks, stroking his cheek.

"Yes." Comes the shaky answer, Jack looking up at him.

Sam smiles before letting his hand wander down, taking Jack's dick in his hand. "Wanna come again, baby?"

Jack shuts his eyes and nods, hips pushing into his hand, making Sam chuckle. He sets a slow rhythm with long, sure strokes.

Seeing this, Dean slips his fingers back into the boy's tight hole. Jack whimpers, both hands digging into Sam's shoulders, but he pushes against Dean, hips jerking between them. A few beats later, Jack is coming into Sam's hand, moaning deeply.

Before Jack is fully recovered Sam has moved down the bed, kneeling between his legs.

"I go first, Sammy," Dean says, handing him a condom.

Sam shakes his head, spreading Jack's come over his own twitching cock. "Don't you wanna feel my come inside him?"

Dean groans. "Sammy- "

"Please?"

Dean sighs but tosses the condom aside, "ok, baby, sure." He squirts a bit of lube into his palm before handing it to his brother.

Sam lubes up quickly, adding to the sticky come, before grabbing himself and lining up with Jack's hole. He looks up at the boy, making eye contact, "you tell me when you're ready, Jack."

Jack nods slowly, taking a deep breath, "I'm ready, Sam. Need something bigger."

Sam chokes, finding it hard to breathe, but starts to push into Jack until the tip of his dick finally gets past the tight ring of muscles. He sighs and does his best to move slowly, trying not to hurt Jack. He pushes steadily until he's all the way in, pausing for a moment.

"He's so tight, Dean." Sam breathes out, staring down at Jack.

Dean nods and pulls him into a kiss. When he pulls back he moves his hand down over Jack's soft cock. "Can't wait, Sammy." Then he leans down over Jack to lay a kiss on him.

Sam hums, hands spreading over Jack's small hips, pulling back slowly, before snapping back in, in a single push. It makes them both moan and he pushes deep again, settling into a quick pace.

Jack's hips are rocking back and forth, unable to get enough of the friction between them, moaning into Dean's mouth. Sam shifts up slightly and Jack screams his name. He adjusts to hit the same spot at every thrust and, suddenly, Jack is coming hard, head thrown back. Sam's thrusts get erratic then, hips stuttering, before he's chanting Jack's name, coming as deep into the boy as he can get.

He falls over against Dean, leaning on him until his breathing is under control. Then he pulls out of Jack, lays down next to him, leaving kisses on his shoulder.

Dean kisses Jack's cheek, then down his chest, all the way down to drop a kiss on the tip of his cock. Then he moves to sit between Jack's legs, prepping himself quickly. "Ready for one more, Jack?"

Jack blinks up at him, sweaty and teary-eyed, but nods. Dean smiles and leans down to kiss him, using the distraction to push into Jack. The boy moans, hips moving to help Dean slide in faster. Dean groans, settling over Jack with arms braced next to his head, too shaky and close to even start slow. Sets a bruising pace, instead, that moves Jack up the bed with every thrust. Dean thinks it must hurt the boy, taking so much in one night, untouched until now, but then Jack moans, head thrown back.

"You like it, sweetheart?" And Jack nods shakily, peering up through half-lidded eyes, cheeks pink with exertion.

It makes Dean groan, shove a little more forcefully into him. "Told you we'd teach how to be a slut."

Jack nods vigorously, "yes, Dean."

"Say it, baby," Dean whispers to him, leaning down until their noses touch. "Say you're my little slut."

Breathless, words broken, he repeats it, "I'm your little slut, Dean."

Dean thrusts harder, so close, so ready to let his come mingle with Sam's, already deep inside the boy. "You are, Jack, you are. You're my perfect little slut." To which Jack's muscles tense up, ass clenching, and it's enough to send Dean over the edge, groaning as he comes into him.

He's coming down, eyes blinking open as his dick gives a few final spurts when he notices that Jack is shaking, eyes closed and head thrown back again. The boy is moaning, trying and failing to get Dean's name out, and he realizes he's coming, dry and untouched, just from Dean's dick. And Dean's eternally grateful to his brother for bringing them together.

As if on queue, Sam speaks up, sleepily, from next to Jack, "you like him."

Dean looks over slowly, eyes still wide from watching Jack, wanting to remember everything about the boy and this moment. His mouth is dry, swallows thickly before answering Sam and it comes out as a whisper, "I love him."

There's a long, tense moment, Sam unreadable, where Dean thinks his brother will resent him for saying that, maybe even hate him. Then, slow from sleepiness, Sam smiles and the painful grip around his heart loosens until he's jelly, light as air. He looks down at Jack who's staring up at him, stock still now.

"I love you, too."

He hears Sam chuckle lightly and he smiles at the boy. Dean never knew he could be this light and happy. He slips out carefully from Jack and settles down on his other side. He knows Sam wants them both to stay and, after all that, Dean thinks he'll probably give in. So when Sam asks he doesn't protest, pulling Jack and Sam as close as he can before letting go into sleep.

#dean/sam/jack #wincest-gaychesters

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ante--meridiem · 5 years

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(You don't have to answer if this is too personal btw) It's just that I've known for about two years that I'm probably-mostly a lesbian, but I never had someone to talk to about it seriously. I'm almost 19 now and never really tried to get involved with someone romantically because I don't want to weird anyone out or make them uncomfortable. And I know that doing stuff at my own pace is totally cool but sometimes I worry that I'm late to the game or something :/ What were your experiences?

Hi anon :). Don’t worry, it’s not too personal. (I mean, my answer is quite personal, but what is tumblr for if not over sharing with strangers on the internet? :P) I hope my experiences can help you, though if you’re looking for dating advice the most I can say is “don’t do what I did”.

I can empathise with a lot in this ask. I realised that I was gay at about the same time as you, and it felt late to me as well - but going by what I've heard from other lesbians I've talked to, I think it's actually quite average. (I think the reason it feels late to us is because most "common knowledge" about LGBTQ stuff tends to focus on gay men, who just anecdotally seem to realise a lot earlier on average). I'm still not 100% confident in my sexuality - I settled on "lesbian" more by process of elimination than anything else. The only thing I'm mostly certain of is that I'm not straight - I could potentially be wrong about liking girls, or about not liking guys, but there is no way that I'm attracted to men more than to women.

Extensive discussion of my personal life below, feel free to read if you want to.

Getting to identify as a lesbian was a really long, confusing process for a few reasons. I'm the kind of person who tends to overintellectualise and overrationalise my feelings, so it was far too easy for me to convince myself that I felt the things I "should" feel. My immediate environment was never intensely homophobic (...extended family is a different matter, I'm still not out to them because I'm pretty sure my grandmother would react very badly based on arguments we've had about LGBTQ rights in the past), but the possibility of being anything other than straight just wasn't discussed, other than in a "that's weird and inappropriate for children" kind of way, so I ended up with the impression that being gay is such an unusual and distinct experience that it would be impossible not to know if you were.

In retrospect, there were a some feelings I had for girls when I was younger that would probably count as crushes/puppy love (I made a girl a Valentines Day card when I was 11, for God's sake, and in my naive obliviousness didn't think anything of it) but somehow I never connected that feeling of intense, nervous admiration to what a crush was supposed to feel like. I managed to think my way into believing I liked various boys and had a tendency to confuse mutual respect for romantic love. (Those "crushes" made me sure for a while that I couldn't be gay, because I liked boys, didn't I? It's honestly hard for me to pick out a detail that proves they were fake, even now, but the main thing that stands out is I preferred talking about how much I liked them over actually talking to them.) Later, I had a phase where I rationalised that romantic love was a lie and indistinguishable from platonic love, and I shouldn’t care so much about it - even though part of me very much cared.

I can pretty much split my realisation into two parts; realising I wasn't attracted to men and realising I was attracted to women. Both parts were difficult, but in their own way. The easiest one (or maybe I should say "simplest" one, since while it was fairly obvious it wasn't particularly easy emotionally - it made me feel even more weird and out of place, which I’d already felt for other reasons) was realising I wasn't sexually attracted to men - except that at the time, I just parsed it as not being interested in sex generally. Somehow the possibility of sex that didn't involve men at all wasn't something I was really aware of. My friends would talk about how attractive various men were, and I'd just feel extremely confused and like I was missing something. Being the pretentious person I was I rationalised it as "sex is meaningless anyway, all I really care about is love".

The other half was much more confusing, but happened in a pretty cliché way - I fell in love with a friend. I can't actually say how long it took me to realise that because I'd always seen her differently from my other friends, but I put it down to admiration, jealousy and wishing I could be her. I kind of assumed that she was just so special that everyone must feel that way around her. A moment that stands out is when she was telling me about various guys who'd asked her out, and I started feeling weirdly jealous about it but also found myself thinking well I can't blame them, if I were a guy I'd want to date her too. From there it took about a year to realise that the "if I were a guy" clause wasn't necessary. It felt completely different from my other “crushes” - she made me feel happy more than nervous, I wanted things to stay just between us instead of wanting to share them with everyone, she popped into my head unasked for instead of me making myself think about her. I was hyperaware of her presence and couldn’t stop thinking about how beautiful she was - which had never happened with a guy.

At that point I started calling myself biromantic asexual (terms I found on the internet and never actually used in real life - the most I told anyone was that I was bi, which it still took a long time to be willing to do - I think I was seventeen by the time I actually told anyone I might be bi), but I was still very uncertain of it. For a long time I told myself that I didn't really like girls, I just liked her. I was also completely in denial that my attraction had any physical component at all, because I felt like that would make it less "pure" and I was terrified of being creepy. I tried asking my parents for advice, but they insisted that admiring your friends a lot was normal and didn't mean anything, and I couldn't explain how I knew that this was different. (It didn't help that they believed the only difference between friendship and romance is physical attraction, and I couldn’t define any other difference even though I knew there was one). My mom was hesitant because it would be harder for me if I wasn’t straight, which... I know she meant well, but it came off like she thought I was choosing to overcomplicate my life, something I internalised and that made me second-guess things even more.

Even once I accepted that I was probably bi, a part of me felt certain I would end up with a man, but I wasn’t happy about it - every time I thought about it, I felt resentful. It was the kind of thing that felt like a bad kind of inevitability. I was also scared to tell the friend in question I liked her, because the pessimistic part of me felt certain she was straight even though she’d hinted otherwise. Eventually I did though, but only when she was about to move away to study in university, and because I was afraid of freaking her out I decided to phrase it in past tense and downplay it (”I used to kind of have a crush on you”). When she took it well, I gained the courage to say I still liked her, but had been afraid to say anything because I was afraid of how she’d react. She told me I should have told her sooner, that gender didn’t matter to her and I shouldn’t have assumed she’d reject me. We spent the next few months exchanging semi-flirtatious messages and she said she might consider dating me some day, which came to a head when I realised she didn’t really mean that. I asked her to just straight up reject me - which she did.

During all this time, I’d come to be very close friends with a guy. He understood me better than almost anyone except the friend I liked (or so I thought at the time) and I felt like I could tell him anything. He asked me out (knowing about the other friend who I was definitely not over) and I accepted, for all the wrong reasons - because it was flattering to be liked, because I was afraid no-one else would like me, because I was trying to get over her and didn’t want to be alone, and because I couldn’t find a reason not to. I told him I thought I might be asexual, but agreed to physical intimacy (not sex, mind you, just kissing and cuddling, but it was enough for me to feel between bored and uncomfortable) anyway, for a lot of the same wrong reasons.

The relationship wasn’t bad per se, at least at first, but it felt - empty. Like ticking off the boxes of what a healthy relationship should be. We had deep, intimate conversations but it never felt like enough. At first, I tried pushing him for more - more depth, more intensity - because I was annoyed with what felt like complacency from him. I couldn’t understand how he could be satisfied - even happy - with what we had. I felt like I was doing something wrong, like I didn’t know how to love right. The first time I tried to break up with him was after I’d introduced him to my former crush, and he noticed that as soon as she was around she had my full attention. I felt incredibly guilty, there was a lot of crying on both sides, but eventually we didn’t break up. The question came up again a few times - he tried to break up with me as well because he sensed I was being distant, and during this whole time, I started fantasising about being with various girls. This was when I started acknowledging that I might not be asexual after all.

In the end, I decided to call myself a lesbian because it was the hard boundary I needed to draw in order to break off the relationship, and kept the label because nothing else seemed a better fit, but part of me still felt like I was faking it. (I once made a friend laugh by saying I had imposter syndrome about my sexuality). I was out to a few people - my closer friends, my parents and my English teacher - but only started being fully open about it once I went to university. I got involved in various LGBTQ communities and while I never felt I fit in especially well with the other people there, it did make the label feel less alien, to the point where I was comfortable casually referring to myself as gay. I even went on a few dates with a girl, but I could feel myself trying to force feelings that weren’t there again. I’d latched on to my sexuality as an explanation for why my last relationship went wrong, and I think I wanted to prove to myself that I could feel the right things if I were with someone of the right gender.

After we decided we wouldn’t work out I decided to stop trying to force things. Right now, I’m very comfortable being single and think it’s best I stay that way until or unless I develop feelings for someone else naturally, though the thought of dating a girl someday makes me feel warm fluttery things in my stomach. (I do realise the chances I’ll just fall in love again without looking for it, and that she’ll be into girls and into me, are very small, but I don’t see a better option). I’m also out to most people who are a regular presence in my life, extended family aside, and the label has stopped feeling just “good enough” and started actually feeling right.

#lgbtq stuff #Ask #Anon #Personal #About me #I ramble #I overshare on the internet for fun and no profit

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redxblueihateloveyou · 6 years

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Hi, what do you think about makoto and haru's friendship? A lot of people ship them but I can't see them as more than just best friends tbh and I don't think haru likes him that way, maybe makoto has feelings for him but even that I'm not sure, what do you think? also am I the only one that finds a little weird the fact that makoto is always helping haru get out of the water? I mean I understand when he's in a pool but when he is bathing in his own house isn't that a bit inappropriate? lol

Hi:) I’ve never seen them as more than friends, I can explain why. It’s not because I’m blinded by my ship or something. The thing is when I got into Free! I’ve been already far too into eastern world, I started digging facts about their real culture after the first animes I’ve watched, then it was facts from friends who moved to/lived in Japan, I was already into BTS by then and started digging into korean culture, too. My point is for most people things like sharing each other boxers, cuddling each other in bed, having tickle fights and having almost no boundaries lead to thoughts “they’re gay” which is basically the main problem for most of k-pop fans who really seem to be tired of this. Not to mention crossdressing and using make-up for a guy.

Why I’m mentioning it is because I can’t see Haru and Makoto doing anything that can be seen as them being more than friends even if I’m watching it from the western point of view where basically just holding hands for 1 minute is gay for some people.

Like most scenes ppl try to shove at me here like:

- “I love swimming with Haru-chan” in Starting Days where he says “skides/suki desu” which is used in japanese basically everywhere including talking about liking food, that way I should say Haru/Nagisa is canon since Nagisa said “Aishiteru, Haru-chan” after swimming with him which is kinda a big deal since they basically don’t use this phrase now, only for a rare special occasions.

- episode 2x06 when he says “I guess I was jealous of Rin”, I genuinely think it was mostly part of the personal what to do with my life crisis they had in s2, because seriously those kind of changes are freaking hard and seeing a person who already knows what he wants from life and another one who doesn’t but have all the great possibilities is really tough, plus I think everybody already kinda knew seeing rinharu race that they have a great future together. Moving on from your basically family all alone while somebody have mutual goals is pretty sad.

- one rinharu fan said about my gay things/bro things gifset that you can compare Haru’s reaction to Makoto leaving to Tokyo to Rin leaving to Australia in TYM and that would be other way around. Haru being upset and angry wasn’t about Makoto leaving per se, it was about people around him moving on without him while he’s stuck. That’s why after the trip to Astralia he was perfectly fine, while comparing it to Starting Days when Rin left and he was a messy fucking mess. While in TYM he was already sure about his future and sharing it with Rin, so why compare those I don’t know.

That being said… if somebody have a straight explanation for Haru’s behaviour when Rin is around I’m open to suggestions really. Why Haru shares bed normally with everybody but getting like this about sharing it with Rin? Why he doesn’t react to others being close to him, but when it’s Rin he gets like this? You know the first thing that comes up on google when you search for “being afraid to call him”? An article “How to text or call your crush without being scared”.

I mean I don’t do anything here, I don’t even need to exagerade when it comes to these two. I have lots of gay ships as you see, so I’m well aware which of them are just me reaching out or dreaming and which are not.

As for the bathtub scene I’m kinda so used to it already, it’s their thing and it didn’t strike me as super weird or anything maybe because if you won’t get Haru out of here, he will stay there forever LOL In some american movie it would be weird I agree, but not here? But once again I’ve watched how bts live together, nothing surprises me anymore lol

Another point: I live in extremely homophobic country. I recommended Free! to a slice of life fan guy, my sister’s coworker who wanted to talk to smb about anime. I got him in with a picture of Gou. He said he doesn’t mind gay people but he can’t watch anything about them (so basically ugh yeah you know this type). He texted me after episode 4 saying he’s dropping it because of the fence scene. That being said bathtub didn’t bother him either, but Rinharu is noticed by everybody. So they’re being gay in a worldwide sense you know.

P.S. What bothered me in Makoto/Haru relationships is Makoto not being his own person, which also concerned Nao in Starting Days and Rin when he said “I was worried you’d only worry about Haru and not focus on figuring it out for yourself”. He was basically Haru’s doormat for most of the time. That’s not my thing really. That’s why I’m happy that they moved on from this and he’s doing fine now.

I’m more of a I’m my own person, but you became a part of my dream kind of girl. I find it really romantic.

I also don’t like the idea of anybody on Free! being unrequitedly in love so it’s not for me either (tho I can see where this is soming from!). I’m into unrequited requited love also known as misunderstandings AU also known as season 1 of Free!

Not to mention that Makoto, Sousuke and Nagisa are the biggest wingmen for my ship, I mean they’re basically me watching Rinharu:

But as I always say, that’s just my opinion, I don’t judge anybody and I totally get why people can see things differently. To each their own cup of tea.

#answered #anonymous #Free!#I won't crosstag it bc I hate when ppl do this and I don't want any ship wars again #they're pain in my ass as it is already

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committoreality · 5 years

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Hi Georgia. Recently I have been very short tempered & critical of my boyfriend. This has happened before and I know I usually do it when I feel stressed or anxious about something in my own life but I can't really pinpoint what is making me act this way. It happens whenever he does the smallest thing to annoy me. I don't want to take out my aggression on him because I know it is unfair but I am having trouble understanding my own feelings. Any advice?

Hi friend. This is definitely something I relate to, so I’ll start by sharing my practical advice and what I do. I think when you’re in a tumultuous place, the best thing to do is isolate yourself for a bit. And this may seem unintuitive to some, but I find that when I seek advice and opinions regarding my own feelings- that adds to the confusion. Taking time alone doesn’t mean you’ll understand the source of your feelings per se, but being alone allows you to sit with the feelings and just get comfortable with them.

I’ve accepted that there are going to be periods of my life, my month, my day, where I feel discomfort. And that is going to disrupt things. My work, my relationships, my peace of mind. And it’s fine because you always come out the other end and get back to your base line, whatever that is.

I find that whenever there is a negative feeling, that negativity is only intensified when you add the additional dimension of feeling guilt about the emotion, rejecting the emotion, or diving so deeply into emotional analysis it consumes too much of your mental energy. My go to technique is to allow myself to feel the way I do, be candid and unapologetic about it, and be honest to the people that my emotions are affecting. For example my mum called the other day, and I was pissed off for whatever reason, and I just said “i’ve been antsy, it’s not you, if you’re feeling hurt I’ll call you when I’m in a more receptive and loving headspace”.

Because it’s not your responsibility to be 100% emotionally consistent. Especially when it comes to intimate others. When you spend so much time around them you can’t guarantee to be the best version of yourself at all times. And I’m even hesitant to say “best version”, because it implies there is a “worse version” that you’re embodying.

My go tactic is twofold. Be really candid in the way you communicate your emotions. I’m not saying punch a wall and yell and be completely unfiltered, nor be completely articulate and be able to put your finger on what you’re feeling. What I am saying is that it’s normal to have these negative feelings that will seep into your relationship. Just tell your partner that you’re feeling some version of x, you don’t know why, you love them, and please be patient. I frequently ask my partner to be patient with me. I have these random unidentified weird feelings and I get distant and sad. And I ask him for his patience and to love me and be a bit more gentle. And I do the same for him.

Secondly, I find that when I’m mad, trivial things aggravate me. So distancing yourself will reduce the frequency that you take out your feelings on those you love. More importantly, it will remind you of all their positive qualities, what you love and miss about them etc. And I find having that reminder makes me treat my intimate others with more love. I don’t have to filter and monitor my negativity because getting the space and the reminder of my warm feelings towards them will smother a lot of the unwarranted manifestations of my anger.

On the other hand, some feelings are not irrational misdirected expressions. And sometimes distance can remind you of the warmth you feel that is at the core of your relationship, and other times it can illuminate you to a problem that hasn’t been addressed. I know that in my past relationship, distance showed me all of these built up resentments. And it showed me that my short temper towards my ex was based on valid, unaddressed issues.

So no matter the outcome, taking time to yourself can neutralize of exacerbate the feelings. Both outcomes are good to know.

And on a final note, I have had the experience (many times), of being pissed, angry, sad, suspicious, jealous etc. for absolutely no reason. And thinking it through, trying desperately to identify the source of my negativity was completely futile because it’s not that deep. Not every feeling is some divine intuition that needs to be honoured, analyzed, or acted on. Sometimes we’re angry pieces of shit because we’re human. Sometimes I get furious about dumb shit and it doesn’t mean anything.

I also find that giving too much attention to an emotional state can actually push you a lot farther from finding the source of the negativity. Sometimes the best approach is to be indifferent to the emotion, and just pay attention to the times that it comes out. Giving less thought to it can bring you closer to noticing the situations that actually elicit the feeling and intensify it.

And I think most importantly, don’t feel guilty about what you feel. I’ve really come to believe that the best relationships are those where you are patient with your partner, endure the shitty times, and give them the benefit of the doubt. My boyfriend and I have been through a lot of real and challenging situations. And I know that our depth of love and commitment is a testament to our capacity to be forgiving, patient, and believe that the best version of each other is always present, sometimes it is latent due to circumstances. Obviously you need to use your discretion and sometimes challenging times are patterned and not temporary.

I think it’s good to communicate openly with your boyfriend, apologize if your actions are hurting him, ask for his patience with you, and give him reassurance that you’ll be there and be patient with him when he’s feelings stressed and being short with you. Because no one is perfect and completely consistent. And if you mutually agree to be patient with each other and endure the shitty parts of one another, that strengthens the relationship.

And if you can’t agree on that, then it’ll be a hard relationship to sustain because the love is conditional on your good mood. So it’s important to give those you love the permission to be shitty and short with you sometimes.

Anyway, I really went off on a tangent, but I hope you can grab something useful from my pontification. Kind regards, G.

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