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Summary -

Sonic and Tails had grown up together since they were both five years of age. Being that close with someone for so long, it isn't a surprise that one of them would develop feelings for the other. Tails decides he wants to be bold about this, and challenging Sonic's ego is the way to do it. Surely this dangerous game they're playing can't go wrong? Sontails/Slight Sonadow/Sonknux

Slight Warning -

This story is Rated M for loads of NSFW content, but considering the title, that's probably why you're here. Don't worry, it's all fluff and some good kink.

Notes -

This story is literally its title for me. I've had a hard time finding some good multi-chapter Sonails, and want to make something different for once. I don't normally ship these two, but sometimes I get in the mood for it. If you like fluffy, kinky stuff like this, then this is the fic for you. Just an FYI, Sonic and Tails are the same age in this fanfiction, and they're both 16. I need them the same age for the plot to work. Also, there's going to be some Sonadow and Sonknux, including M/M/M stuff. Haven't written smut in a while, and decided I want to do something nice.

- Anonymoux-Sonic

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Guilty Pleasures

Written by Anonymoux-Sonic

Beta'd by Capi

Prologue - The Bet

Stepping out into the living room, the golden fox stops to admire the sight laid out on the couch before him.

A blue hedgehog he knew all too well was laying across the couch on his back. His large quills were swept to one side, a hand over his chest, one arm and one leg hanging over the edge, while the other leg was propped up slightly and leaning against the back of the seats. He was sleeping completely still, which meant he was truly out of it in a really deep state of sleep. The moonlight from the window behind the furniture was casting on his cobalt fur, making him glow in the dark room and look just...

Shaking his head and walking over, the fox sits on the edge of the couch and holds out a hand to gently caress the side of the blue hero's muzzle. He smiles when Sonic turns his head, subconsciously burying his nose into the fox's hand and breathing in deeply, as if even in sleep he knew who this was and that he was comfortable with him.

That was something Tails was very proud of...the fact that Sonic the Hedgehog, Hero of Mobius and number one nemesis to the evil Dr. Eggman Robotnik, was his best friend, and felt comfortable around him. That he had the chance to grow up with this famous hero, through thick and thin, and see the sides of him that everyone else just wished to know. He loved this very thought, and cherished it every time he so much as looked at him.

Sonic shifts in his sleep, and Tails could tell the hedgehog was cold. Deciding that his current position probably wasn't the comfiest, the fox lifts the others arm up and places it on his fawn chest, before lifting the dangling blue leg up as well and putting it next to the other. He decides to take the hero's shoes off, gently tugging as to not startle him (and get kicked painfully in the process, something he's learned the hard way from), before putting both red shoes on the floor beside the couch. He takes off his gloves and socks as well, a move that would seem inappropriate to others if they hadn't been so close, and puts them on the table nearby. He grabs the blanket from the head of the couch and throws it over the hero's body, tucking him in so he would stay warm throughout the night.

After his work was done, the fox teen stops and looks at his friend again, feeling an ache in his chest he wanted to confess so dearly.

How would Sonic react? Would he give him that chance? Would he reciprocate those feelings? He wasn't sure, to be completely honest. He knew Sonic like the back of his hand, but when it came the hedgehog's emotions, it was a pure mystery. Sonic claimed to care for him more than anything or anyone in the world, but was that simply brotherly love, and if so, could it possibly change and become something just a bit more special?

His crush on Sonic was something he's had since they were children. Over the years it's only evolved into something more, no matter his attempts to cover it. He just couldn't help it.

Now that they were both sixteen, Sonic only older than him by so many months, he wondered if his chances were better or for worse. What if Sonic fell for someone else before he could confess? He knew the hedgehog had his eyes on another certain somebody, a male for that matter, but would Sonic even consider his best friend as a candidate?

In his worried state, he gently grabs the hero's fawn hand and holds onto it longingly.

He knew that if he wanted to have Sonic, he was going to have to make a move very soon, and very quickly. He just didn't know how to go about it. One false move could shatter everything, so he really needed to plan this out.

He was smart, so he was sure he could conjure something up. Besides, many told him, including their friends, that Sonic loved him more than the world, so if that was the case, it might not be hard to turn that love into something...better. He just needed the right push.

He remembered a time just last year, where he almost had that push. They had been at a party at Club Rouge, celebrating the twos' birthdays together. There was a running joke by Rouge herself that the two looked adorable together, and that they should, to celebrate their big day, have a "birthday kiss."

After everyone got involved and pressured them over the course of the party, the two finally gave in. He remembers it so clearly. How pink Sonic's face was, how soft his lips were, how flustered he was afterwards…

Looking down at the sleeping hedgehog, he wonders if Sonic has felt the same way about him this whole time, and neither have been brave enough to admit it. Maybe it was time he took charge...and figured it out for the both of them.

He decides he's been awake too long, and reminds himself that he and Sonic had a busy day tomorrow, so he leans forward and presses a soft kiss on his hero's forehead, before getting up and leaving him to his bedroom.

Stopping at the edge of the cliff, the blue hero kneels down into a crouched position, emerald green eyes locking on the large base in the distance. The base was tucked away within a thick growth of jungle trees, and in the shape of a thin tower with a wide, disk-like top. It's bottom was surrounded by a tall, sturdy metal wall, and robots could be seen flying in and out in dozens. "You sure this is gonna work?" he asks, turning to look back at the yellow fox standing beside a red bi-plane.

"Oh yeah," the fox smirks confidently. "I've thought of every possible way this could turn out, and we're always winning this."

Sonic grins, standing to his full height. "That's pretty snazzy of you."

Tails smiles back. "I've been working on my snazziness."

With a chuckle, the hedgehog walks over and stands beside the golden teen, the two at equal height as they looked over the holographic map in Tails's hands.

"We've gotta plant a bomb here," the genius points, "and here. With bombs on either side of the base, the explosion is going to knock out everything within the walls."

"So we get in, get out, and run really far away," Sonic smiles. "Sounds like a walk in the park."

"Maybe," Tails hums, looking up at the base itself. "We need to try and make as little noise as possible, but take out as many robots as we can along the way. We don't want any escaping."

Sonic takes a couple steps back, bending over to stretch to his toes. "Betch'ya I can take out more than you can, and be back here before you."

Tails freezes, his eyes glued to the stretching hedgehog, a lump forming in his throat. He was making a bet…

He starts talking before his mind registers what he's saying.

"You really think so? I've studied this map a hundred times," he tries to sound as cocky as his friend, taking a couple steps forward to show off said map. "No matter how fast you are, I know all the shortcuts."

Sonic bounces a step forward, eye to eye with the fox, a twinkle of competition in those bright irises. "Your brains against my speed?"

"Bet," Tails smiles back.

"Hmm…" Sonic puts a finger under his chin, thinking hard on what he should wager. "How high are the stakes?"

Again he talks without thinking. "How hard do you think you're gonna lose?"

Sonic whistles, putting his hands on his lithe hips. "You really have been working on that snazz. Alright then…" He stops for a second, before eyeing the plane behind the fox and smirking devilishly. "I win, I get my plane back."

Oh no. Was he being serious? Sonic had made many comments over the past few years about wanting the Tornado I back, after his first one was completely destroyed by the Egg Carrier. Tails had sort of taken over it, and loved it too much to want to part with it. Every time Sonic asked to have his plane back, Tails had to find excuses as to why he couldn't give it up. Sure he could just make another plane, but...this was the Tornado. It was practically his baby.

"You would seriously take the Tornado back?" he has to ask. Sonic nods firmly.

"You know how much I've wanted it back," the hero says. "I don't want to watch it end up exploding, again."

He wasn't lying. Sonic loved that plane, loved flying it. He would take it back and hide it somewhere in a heartbeat. The stakes were high.

Tails frowns, looking over at the plane. "You know that plane means a lot to me," he says, turning to look back at Sonic, who had a curious look on his face.

"I know, that's why I haven't taken it back," the hedgehog admits.

Tails drags it on, his namesakes waving behind him. "I'm pretty sure nothing means as much to me as that plane...well...besides one other thing..."

Sonic raises a brow, arms crossing over his chest. "Oh? What's that?"

The shots were lined up. He was glad he had gotten better at acting over the years, because while inwardly he was screaming, outwardly he only smirked and shrugged casually. "Only you."

Sonic blinks in surprise, and...there it is. There's a hint of pink on his cheeks and Tails has him right where he wants him.

"O-Oh really? Then what do you want from me?" Sonic asks, his stutter not going unnoticed.

This was it. This was the push he needed. This was what he could use to see if he could truly have Sonic the way he wanted to.

Closing the distance between them by only an inch, he watches the hero's expression become slightly surprised as he grabs his hands with his own.

"Remember our birthday last year?"

There it is.

The cobalt's muzzle became a light crimson, a look of pure shock taking over its owners face.

"Y-Y-Yeah, w-what about it?" Sonic forces out, tripping over his words. His hands are tense in Tails's hold, and the fox is surprised on how calm he himself was being.

Deciding to break the very fine boundary between them at that moment, he leans forward, nuzzling into the side of the hero's face. He hears Sonic's breath catch in his throat, and it takes all of his willpower to control his own breathing as he says, his voice almost a husky whisper; "If I win, I want a repeat, but as far as I want to go with it this time."

"Y-Y-You…" the hedgehog stammers, seemingly dazed, blinking rapidly with his cheeks practically on fire now. "Y-You...w-want to…"

Tails pulls back, and Sonic quickly looks away, avoiding his curious stare. The hedgehog shifts almost uncomfortably on his feet, and Tails can see him biting the inside of his cheek.

He decides to continue playing it off cooly, shrugging. "I mean, you sounded so confident in winning this bet, that I had to make it worthwhile for myself, you know?" Pulling the strings he knew all too well, he asks; "Are you sure you're gonna win?"

Sonic pulls away, crossing his arms and putting on a nervous smile, face still red. "O-Of course I'm gonna win! There's no doubt about it!"

He kind of feels bad for messing with Sonic's ego, but then again, the stakes were very high. This was his chance to see if Sonic and he could actually be together, if Sonic could reciprocate his feelings for him, or even admit them if he already had them.

"Then," he asks with a smirk, "you don't mind my bet, do you?"

Sonic's facade falters for a second, the hedgehog obviously second guessing himself. "N-N...Not at a-all…"

He had him.

Holding out a hand, Tails smiles proudly. "Shake on it then, and we start once we're down there?"

Sonic eyes him carefully, before taking his hand and shaking it.

"D-Deal."

He's flying like his life depended on it.

Technically, when it came down to his love life, it kind of did.

He doesn't see Sonic or any flash of blue as he's flying back to the Tornado. A part of him is worried that the hero is in trouble, but then the sound of a sonic boom can be heard, and the fox flies faster.

He can just see a flash of blue in his peripheral as he's nearing the cliff the Tornado sat on. Sonic would have to run up it to make it there...and…

He practically cheers out as he lands right next to the plane, only a split few seconds before Sonic is there, the two of them panting.

Then the base explodes.

They both yelp, almost completely forgetting about the whole reason they were there in the first place.

A plume of smoke erupted into the sky like a mushroom, fire and sparks shooting out of every wall in that base. They watched in slight awe as the area erupted into pure reds and oranges. A ship could be seen in the distance, flying towards the base, and without a word, both teens jump into the Tornado and take off before it could spot them.

The flight home was quiet. Sonic sat on the wing, not a word from him about the bet. It wasn't until they landed in the Tornado's garage, and the two jumped off, that Sonic finally spoke up.

"There's no way you didn't cheat."

Tails smiles, having had the feeling Sonic would try to talk his way out of losing. Then again, considering the bets made… "I told you I knew what I was doing."

Sonic gives him a look that's almost completely unreadable, save for the twinge of nervousness in his green eyes and hint of pink on his cheeks. "Can we eat something?"

Tails decides to save the hero the embarrassment and nods. "Foods on me."

He was making chili dogs, figuring Sonic deserved it after what was to come within the next few hours. He couldn't believe he had actually made such a bet, and that Sonic even agreed to it.

'I mean, I did manipulate his ego into it, but…'

He did feel kind of bad, but at the same time, this needed to happen. He just...needed to start this. Needed to get Sonic to recognize his feelings.

He was pretty sure by now that Sonic did in fact have feelings for him as well, he just needed to get that out of him. Needed to confirm it. He hoped that Sonic agreeing to this in the first place was the first step in the grand scheme of it.

The sound of soft footsteps into the kitchen brought his eyes up to the hero walking in, wearing his towel from his shower around his neck, fixing his white gloves as he sits at the small round table in the center of the room. He seems to realize then what it is the fox is cooking, and looks up with a small bit of excitement written over his face.

"You're making chili dogs?"

Tails raises a brow, smiling. "You didn't smell it right when you walked out of your room?"

"I wasn't paying attention," Sonic half-heartedly admits, but there's a small smile on his face.

Finishing making their plates, Tails takes their food to the table and sets Sonic's down in front of him, before sitting in the chair beside him. Sonic murmurs a thank you before they sit in silence, eating their meal, both with most likely the same thoughts on their minds.

There was a noticeable tension in the room, and Tails noticed that neither of them were really eating much. For Sonic to not have scarfed down his chili dogs by now, meant that he was most likely stressing about whatever was to come.

Tails was too, but he needed to be strong for the both of them.

Making a decision, the fox puts his half eaten food down and stands up, grabbing his plate to put in the fridge. Sonic looks up almost too quickly, blue ears perked forward as he tried to figure out what Tails was up to.

"I'll be back," the teen calls, stopping in the doorway on his way out. "You're not going to run off, are you?"

Sonic's face reddens, and he looks away, mumbling a quiet and hesitant, "no."

If this was going to get as far as they both suspected it would, he wanted to be prepared. He heads down to his lab to grab a few things, before heading to the bathroom.

Sonic's fear was starting to show itself. After washing himself up and getting some things ready in Sonic's bedroom, Tails went to get said blue hero, who was actually still sitting in the kitchen. He was honestly shocked the hedgehog hadn't run off, but he was rooting that it was because Sonic truly wanted this...whatever this was going to be.

He had taken his hand and led him through the house, up the stairs, and into Sonic's room, and by the time the door was shutting, Sonic couldn't hide it anymore. His face was beat red, and his legs were shaking. Tails sits them both on the bed, his own anxiety kicking in, wondering if he could really do this. Sonic was still going along with this. They had to keep going.

Sonic's quills are flattened slightly and his ears are folded at their sides. His thoughts were impossible to read, but the fear was clearly there, and Tails had to take in a deep breath himself, before deciding to get on with it. He didn't want to prolong it any more, for their anxieties' sake. Sitting close to the cobalt male, he doesn't give Sonic a chance to move before he's cupping his muzzle in his hands and pulling him into a soft, gentle kiss.

The hedgehog makes a surprised sound, but doesn't pull back or fight it. Their eyes are closed and they're still for a second, before Tails decides to move their lips together, reaching with his other hand for Sonic's shoulder and pulling him closer.

The hero slowly gets into it, their lips breaking apart and pushing back together softly and experimentally, Tails leading them on. The fox lets the hand that's holding Sonic's muzzle slide around his head, sliding expertly in between cobalt quills as if he had been doing it for years. This seems to be a sensitive area, because Sonic makes another tiny sound that could be taken as a hum.

He can feel the hedgehog still shaking slightly, and he rubs his other hand up and down his fawn arm to help ease him. His hand in his quills massages the back of the hero's head, and Sonic lets out a shaky breath and another soft hum.

Deciding to focus back on the other matter, he takes a second to appreciate that Sonic's lips were still as soft as they were before. He wants more, though, and shows this by letting his tongue run along the other male's bottom lip. Sonic stiffens for a second, before shakily letting those lips part, if just barely. Tails makes it work.

He slides his tongue in between those lips, feeling along sharp hedgehog fangs and then the others own tongue. Sonic's hands grab the blankets beneath them, before balling into fists. He's shaking a bit more now, but he's still responding to the kiss. Tails tilts his head to go a little deeper, and somehow convinces Sonic to move with him.

Sonic tasted just as amazing as he thought he would, Tails thinks to himself. Was just as warm as he imagined. He was ecstatic that the cobalt hero was actually going with this, and decides to push a little further.

He pulls away to give them a small break for air before leaning in for another kiss, Sonic meeting it and falling into it easier this time. He moves without separating them, moving his hand from Sonic's arm to the hedgehog's small blue waist, shifting him so he was further on the bed, fully facing him. He then shifts himself, leaning forward slightly to get his legs under him so he's on his knees, meanwhile moving Sonic's legs apart to get in between them. Sonic makes another sound, this one a shaky whine, as Tails lays him down on the bed and takes his place between his legs, leaning over him, all the while never breaking their lips apart.

When he finally breaks the kiss, it's because Sonic needs air, and instead of stopping completely, he just trails kisses down the hero's muzzle into the crook of his neck. Sonic lets out a 'hahh' of air, subconsciously turning his head to allow Tails more access.

This was going too well, the fox thinks.

He lets his hands fall down Sonic's sides, one of them resting on the hedgehog's hips, while the other slides down even lower to strong blue thighs. He massages both areas his hands are in, feeling Sonic keen in his hands, and it feels amazing.

He continues pressing kisses down the hedgehog's body, stopping at his shoulders to nip lightly, before moving across his chest to the middle of it, letting his tongue run along a small part of it.

"Hah-T-Tails…" Sonic huffs out, back arching slightly, legs twitching from the work the golden teen's hands were doing.

"Are you feeling good?" Tails asks quietly, leaning up to press a kiss onto the hero's left cheek. Sonic flushes darkly, turning his head away and slowly, shakily, nodding.

Tails can't help but smile. "This bet might be more in your favor, you know…"

Sonic makes a puzzled face - brows furrowed and a small frown, before gasping in surprise as Tails leans back down and runs his tongue over his right nipple. "Oh-!"

The sound is music to the fox's ears, and he wants more of it. He abuses the small nub in his mouth, pressing his tongue against it and nipping it with his teeth occasionally, making Sonic's body shudder beneath him and bringing more delicate noises from the hero's throat. He moves his hands again; the one on Sonic's hip moving to the small of his back, while the one on his thigh moves upwards, inwards, until it's cupping the hedgehog's crotch and Sonic is calling out his name again in surprise.

Tails was suddenly glad he did a ton of research within the past year. Hitting puberty and finding Sonic attractive in this way had inspired that need for research. Sonic was obviously completely oblivious to these activities, so he supposed he lucked out big time. The cobalt male was as innocent as ever, and he could take full advantage of that by making this the best he could.

Having Sonic in his hands like this, completely under his control, was definitely getting him off. There's a growing heat in between his own legs that he tries to ignore for now, wanting to get Sonic completely disheveled before going that far. He wanted to turn him into a mess before he even considering taking him.

So far, that was going more than well.

He rubs his palm against the hero, feeling the area heat up with every movement against it. He brings his mouth lower, down to Sonic's stomach, which is apparently super sensitive - he learns as he tongues it, making the male beneath him gasp loudly and try to arch away from the touch.

"T-Tails…" Sonic calls out, voice higher pitched than normal. The fox keeps moving down, pulling Sonic's body up to meet his mouth, using his teeth against the others sensitive flesh, leaving small hickeys across his belly to his hips, down to his waist. Sonic meows out a weak moan, before cutting it off with a quick intake of air. Tails pauses at this, stopping just at the hero's hip bone.

"You don't have to be quiet, Sonic. It's just us," he says softly, pressing a warm kiss down on where fawn fur met blue.

Sonic only makes a strained hum, eyes squeezing shut and ears falling against his skull. Tails decides to pull back up, reaching to connect their mouths again. Sonic accepts this, but a muffled moan leaves him two seconds later, when Tails pushes his thumb inside the hidden pouch down between blue legs. Sonic's hands shoot up to grab onto the fox's arms, and Tails counters by grabbing one of them with his free hand, pinning it above the hedgehog's head. He feels around more inside the hot sheath down below, coming into contact with the sensitive organ he was looking for.

The moment his thumb presses down on its tip, Sonic is bucking, a loud whine and groan leaving him, never before been touched by anyone in his life until now. He almost tries to pull away, before Tails breaks their kiss and gently murmurs in his ear; "Let me touch you…"

"Ahn...hah…" Sonic pants out, tips of his ears and top of his chest flushed as red as his muzzle. They weren't even at the big parts yet, and Sonic was a mess already. "Ah...I don't...I don't know if I-ahhaah…"

"You're okay," Tails reassures. "Just let me do this. You'll feel so good, I promise."

He had a small feeling Sonic might start to panic at this point. The hedgehog didn't like being restrained, held down, or not having any control over himself. This was pushing boundaries the hero had never let anyone cross before. He hoped he could get Sonic to get over this. He was determined to, more accurately.

"Tails…" Sonic starts again, and Tails pulls back, meeting those glossy emerald eyes with his own firm blue ones.

"Do you trust me, Sonic?" he asks quietly, not stopping in his hand movements. Sonic looks unsure, but shakily nods. Tails nods back, leaning forward to press a kiss in between cobalt's eyes. "You'll be okay, True Blue," he says reassuringly.

He feels outside the sheath down low for the pressure points there that would fully expose the hero, and once he does, Sonic becomes a babbling mess.

"Tails-hah-I-I don't th-think-hah-I...I don't think I-"

Tails cuts him off with another kiss, while pulling both hands away to ease his gloves off. Once they're out of the way, he gets to work again; one hand holding the side of Sonic's muzzle while the other slowly starts feeling along the cobalt male's now exposed member.

His fingers feel along the tip, before trailing lightly down the side of it, feeling every curve and dip and making Sonic tremble in his care. Leading his fingers back up, he wraps them around the tip, and starts pumping.

"Nng-hhahhaaah-" Sonic chokes out, hips bucking into the hand that was now treating him, before his lips are claimed into another kiss. He's doing better, Tails notices, so he decides to go a little further.

He pulls away from Sonic's lips and starts heading back down, spreading kisses and love bites all the way down. Sonic meows out again, this time louder, his fingers squeezing the blankets under him, his eyes opening and closing, unknowing at what to do. Tails makes it down to his goal, which was now dripping with a light, clear liquid, and presses his tongue against its tip.

"Tails!" Sonic cries out, before putting a hand over his mouth and attempting to sit up. The fox keeps a hand against the hero's chest, keeping him down, and all Sonic can do is whimper into his own hand as suddenly Tails takes him into his mouth.

Little did he know the golden teen was getting his fingers wet in the process, coating them enough to his satisfaction. Once he deems such a thing, he moves his hand from the cobalt male's chest to blue legs, lifting them up a bit so they were out of the way enough for what he needed to do. He's trying to keep Sonic distracted with his mouth still on his member, letting out small hums here and there, giving attention to just the tip, while his wet fingers started to pry at a very small opening just under a blue tail.

Sonic notices despite his attempts, a loud whimper breaking his lips and muffling into the hand he still had over them. Tails lifts his free hand up to the hedgehog's chest again, feeling for one of the two sensitive nubs there to pinch and squeeze. Sonic takes it, moaning and arching to the touch.

Tails gets to work again, gently and slowly pushing with a finger into the tight hole he wanted in. Sonic was tight, but seemed distracted enough to take it at the moment. He starts pushing in, slowly all the way. Sonic attempts to call his name again, but can't get his words to form properly, and ends up letting out a strangled moan instead. The fox teen curls his finger up, brushing against something smooth and very, very sensitive.

"Ah-!" Sonic gasps out, bucking down instinctively, and Tails realizes what this was. With a tiny smirk, he pulls his finger back a bit, to jam it as hard as he can into that sweet, delicate spot.

Sonic bends in his hold, letting out his first, loud moan of the night, legs kicking and falling limp to their sides. He was pulling on the sheets for dear life, his vision hazy and a hot flash of pure ecstasy falling over him from head to toe.

Now that the blue male was finally broken in, Tails goes fully at it. He pulls his mouth away from a needy organ and trails kisses back up, thrusting his finger against the hedgehog's prostate every second. Incoherent words, loud moans, and cries are flying from Sonic's lips, which were flushed and moist from panting so hard. His fur is ruffled and sweat is giving it a slick shine, and his emerald eyes were cloudy beneath rapidly blinking blue lids.

This was too good to be true, was all Tails could think. He's wanted this for so long now, and he was finally getting it. It felt like a rewarding trophy for all the waiting and stressing over whether he would ever get this far, and hell did victory taste so sweet.

He adds another finger, slowly but surely, and starts to try and stretch the cobalt male as much as possible. His other hand goes back to work on the dripping member between them, despite how much his own crotch ached at the lack of attention. He could deal. He wanted Sonic to go crazy.

"Tails…" Sonic whines between kisses, weakly bucking to try and get more from those fingers down below. The fox could tell the hero was reaching, wanting more than just what he was getting. He pulls their mouths apart, resting their foreheads together.

"You ready for this?" he asks softly, and there's a flash of fear in emerald eyes, if only for just a split second. To help convince him, Tails pushes against that sweet spot again, making Sonic gasp and stutter, a weak moan passing quietly through his lips. It takes a few seconds for him to recover, but when he does, he looks away, embarrassed, and nods.

Tails pulls his fingers from the shaking body, finally reaching for his own needs in between his legs. He was hard, and wet from eagerness, and he lets his hands stroke himself a few times to coat himself with a thin slickness. He leans down and presses his lips against Sonic's again, aiming to distract him from the next few events. He didn't want to hurt him, but he knew slight pain was inevitable.

He reaches a hand under Sonic's frame and lifts his lower half up more, their hips meeting for a second as he repostions them. The hedgehog makes a nervous sound, which smothers into the others lips, as he feels something prod against the pulsing opening under his tail.

Tails starts slow, not wanting to rush it, rocking his hips forward carefully and entering as gently as possible. Sonic is tense and shaking, and the fox reaches down in between them to distract him by fondling him.

It's a delicate process, filled with sweet nothings whispered into blue ears and kisses trailed over his face and chest, but he's able to get his tip in, and after that, it's a bit easier.

Sonic is huffing, barely able to focus on the attention his crotch was getting while being stuffed, but he's handling it amazingly well, and for that Tails is proud. With a few more easing thrusts, he's able to get all the way in. With that, he pulls out, pushes back in a bit faster, pulls out again, then stops to see if Sonic is okay.

The hero seems to be enjoying it somewhat, so the golden kitsune decides to speed it up by a ton.

He thrusts in, aiming for and nailing that sweet spot he was coming to know so well, and Sonic cries out loudly, his voice filling the quiet, dark room. Tails holds the side of the hero's muzzle as he snuggles into his neck, pulling back to thrust back in just as rough as before.

It doesn't take much longer for Sonic to fall apart again, and soon they're both panting and moaning into each other's mouths, the submissive one of the two lifting his legs up to wrap around a yellow waist, pulling the fox closer. Fawn arms wrapped around the teen's neck, as Sonic started to kiss him back just as eagerly, their tongues wrapped up in each other and filling the corners of their mouths.

It was a dream come true for Tails. It was just as good as he imagined it, with Sonic a melted pile of pudding beneath him, thrusting inside his lithe form, hot and wet and tight and so damn good. He felt like he was losing his mind, drowning in the hero's moans and cries and gasps for air, and never wanting to stop.

He was almost disappointed when he felt himself get close, but Sonic was even closer and he knew they wouldn't last much longer. He lifts Sonic's bottom end up a bit higher, aiming deeper and thrusting harder, wanting to rush the cobalt male over the edge.

It hit them faster than he thought.

"T-T-Tails!" Sonic practically screamed, before his body shudders and he's falling into bliss, and Tails falls shortly after, pulling the other as close to him as possible as he fills him with his seed. They're both whimpering into each other, faces buried in both yellow and blue, trembling from head to toe through their orgasms.

He's not sure how long they sit like that before they recover, but when they do, he's exhausted. He carefully pulls out and away from the hedgehog, laying beside him and grabbing at the towels he had left beside the bed. Sonic is limp and looks as if he's about to pass out as he cleans him up, throwing the towel somewhere when he's done. He pulls the hero on his side and against him, pulling the blankets up over their shoulders.

Sonic snuggles into his white chest, humming quietly against him. Tails presses a kiss on the hero's forehead, before nuzzling him back.

"Sleep good, Sonic."

They're both out, only minutes after.

He had woken up early to make Sonic a well-deserved breakfast, a pep in his step and a smile on his face the entire time.

He had done it. He had Sonic.

Now, he wasn't sure where to go from here. It all really depended on how Sonic reacted when he woke up. He supposed he'd just wait and see, but no matter the outcome, he knew it was going to be okay.

Sonic wasn't a romantic person, so he figured it was probably best not to pull that card. No, Sonic liked challenge, fights, and was pretty masochistic, so keeping the edge in instead of all gooey lovey dovey, was probably the best option. Of course, he was definitely going to pull that card when he wanted to fluster him, so using it as little as possible was the best option here.

Maybe if he could keep playing at Sonic's ego, he could keep this up. If he could keep making bets and challenges, winning, and earning that reward afterwards, maybe he could convince Sonic to just stay with him.

Again, it really depended on how Sonic was when he woke up. For all he knew, he was overthinking things, but Sonic really was an open card, here.

He grabs the plate of breakfast and heads to Sonic's room, stepping in to see the hedgehog sitting up, rubbing his eyes. He must have just woken up.

"Good morning!" the fox teen calls cheerfully, making the hero's head fly up and blink in surprise. Then, a shade of red casts completely over his muzzle like a curtain, blue ears folding to their sides in pure embarrassment.

Tails sits on the edge of the bed, holding out the plate of food in offering. "You feeling okay?" he asks softly, tilting his head. Sonic takes the plate, looking down at it, face flushed as ever.

"Y-Yeah…" he mumbles, grabbing the fork he was given and stuffing his mouth before he was asked anything else. Tails chuckles at this.

"So you're not too unhappy about losing the bet, now?"

Sonic chokes on his food at that, swallowing and turning his head to cough lightly into his elbow. "N-N-No," he coughs out, immediately going back to his food.

"I'm happy," the golden male admits, before leaning forward and kissing the hero's cheek, taking him by surprise. "I found out where Eggman's new base is, so we can head out in a bit, okay?"

Sonic nods, taking another bite of his food, looking a little delirious.

Tails smiles.

This was going way better than planned.