Posted originally on the Archive_of_Our_Own at https://archiveofourown.org/
works/12591244.
  Rating:
      Explicit
  Archive Warning:
      Underage
  Category:
      M/M
  Fandom:
      Sonic_the_Hedgehog_(Archie_Comic)
  Relationship:
      Miles_"Tails"_Prower_&_Sonic_the_Hedgehog
  Character:
      Sonic_the_Hedgehog, Miles_"Tails"_Prower, Honey_the_Cat, Sally_Acorn, Amy
      Rose_(Sonic_the_Hedgehog)
  Additional Tags:
      Crossdressing, GONE_SEXUAL
  Stats:
      Published: 2017-11-01 Words: 8190
****** Something New, Something Different ******
by orphan_account
Summary
     Tails owed Honey a favor, that much was true. Initially frustrated
     with the prospect of wearing Honey's clothing, he changes his mind
     when he's enchanted with the idea of appealing to Sonic. When Sonic
     himself gets a little inspired, the pair become the closest they have
     ever been.
Notes
     Something I'd been meaning to do for a long while! I really wanted to
     get experimental this time around, so the narration here is a lot
     more Lemony than usual. It's overall kind of goofy so I wanted to
     make it really entertaining, as well as of course something really
     lewd as well. Hopefully you'll enjoy reading it as much as I enjoyed
     writing it!
     Also, I love Honey. Can you tell?
     Criticism HIGHLY ENCOURAGED.
  This work was inspired by
      Realizations by Bdugo
"Miles Prower! Just the fox I wanted to see!" A golden furred face grinned in
the doorway of Tails' workshop, words just barely heard over the chattering of
powered appliances and whirring machinery. Guess who.
"Oh, I didn't expect to see you here, Honey. What's up?" Tails turned to face
the figure in the door and gave a friendly wave. The boy was hard at work on a
little pet project of his: a powerful new set of core parts for the Tornado in
the form of a fresh engine and battery of his own design. Said parts were
intended to cut back drastically on energy consumption in addition to reducing
air pollution. For as much as he and Sonic traveled, he believed that this was
long overdue. Eggman wasn’t the only thing that threatened the planet, and it
was only fair that Tails did all he could in protecting it.
“That’s pretty thoughtful of you, buddy,” Sonic had said. He admitted he would
have never came upon the idea if it wasn’t brought up to him first. That was
why Tails was the tech guy.
This was what stole the young prodigy’s focus for the past few hours, so
despite his clear and warm greeting, he was internally groggy and wobbly,
unsettled at this unexpected visitor who tugged him away from his efforts.
Honey had a loose grasp on the nature of Tails’ work, but the realigning of
Chaos-whatzits and tireless reworkings of spatial-whozats was a little more
than a short walk outside her court of comprehension. "You tell me, kiddo.” Her
hidden arm came into view, in its hand a tangerine top and skirt.
Tails scrunched up his mouth. He made a promise. And yet, he had completely
overlooked it. “Oh right…er, could it be some other time? I've been doing some
adjustments to the Tornado so Sonic and I can get flying again, and well..." He
grimaced at the thought of piloting the biplane in a frilly looking dress.
Yeesh.
"Aw, you can't spare a little time? I can't just do some measurements and go,
I'm gonna need more data than that."
Tails' eyes narrowed. “What do you mean?” He knew what she wanted, and
practically asked for it. “I hope you don’t expect me to wear that all day…”
Honey walked up to the young inventor and placed the outfit in his open hand,
dismissive. "That's exactly what I'm asking! Give me feedback on how it feels
and all that good stuff,” she said with a wink and a toothy smile, hoping the
fox boy would catch her enthusiasm. Right now she was hoping for too much.
“You… you couldn't get anyone else to try on your...girls clothing?" Tails set
a wrench on the table and eyed Honey warily. "I really don't think I could wear
this in front of the others."
Honey’s eyes glimmered. "Well this wasn't just any old pick. If you want to dig
a little further, I'll have you know I picked this outfit for you because I was
confident a certain blue hedgehog was bound to  love  you in it."
Tails opened his mouth, letting loose a particularly terrible mangling of the
English language. "Y-you...what? I don't...huh? Honey… you mean Sonic?" He
tilted his head and his twin tails swished in a circular motion behind him. He
wasn't sure what the frisky feline's words meant, but being honest with himself
he didn’t want to know. “What are you saying?"
The cat grinned, closing her eyes. "Sorry kiddo, answering your questions takes
time, and unfortunately wasted time is wasted money. If you wanna know more,
you're gonna have to help me out here like you promised~"
Pursing his lips, Tails sat on her words for a moment. Her mind games were
working on him, and that made him...frustrated. “I should probably get it over
with, then...” Mildly annoyed, he gripped the dress and silently waddled off
into his private quarters.
"Aw thanks, I knew you'd come through!" Honey shouted. The door shut.
 
===============================================================================
 
 
“Oooh, don’t you look the sweetest!” Honey rubbed her chin, satisfied in her
handiwork. “How do you like it?”
Tails tugged at the rim of his skirt as he sized up the total cutie in the
mirror. The orange and white bows on his head and tails were an enhancing touch
that seemed to add to that “natural charm” people told him he had. And that was
only an accessory. The actual outfit - a relatively uncomplicated orange
sleeveless dress with ruffled edges and a white stripe across the middle - was
fascinating in its appeal and how well it emphasized the fox’s better features.
The white leggings appeared to really wrap the whole package up.  That’s me?
“It’s a little tight, but surprisingly comfortable. Really nice, actually!”
Tails guessed the modish and trendy spirits of the fashion gods themselves had
made Honey their willing vessel, because there was little denying that she was
darn good at what she did. He really looked convincing. And felt convincing.
...And pretty. He felt pretty.
"Good to hear! I’ll have you wear this for just one day,” Honey said, adjusting
the tangerine bow on his fur. “No more, no less. Promise."
"...Then that’s it?"
"Yep!"
"...Really?" Tails shook.  What if she has more planned? Oh, this cat’s gonna
kill me.
"Yeah, really! You've done what you promised you would do. I can't keep forcing
you, can I? I’m only holding you to your word.”
Her integrity was at least worth commending. With an exhale Tails’ twin tails
slumped to the ground as he imagined the amused looks and chortles his peers
would give him. He did promise to model for Honey. He just didn't think she'd
hold onto his words and pin him against the wall with them some weeks later. To
escalate the tension, a few stray questions tugged at his tongue for answers.
"...But trust me, by the time this day is up you'll  want  to keep doing this
with me," Honey added. There was a clear conviction in her voice that sent the
young fox mentally stumbling. He washed out his stray thoughts with a question.
"Err… what about what you said... about Sonic?" The boy's words came out
stilted and awkward, which drew out a faint chuckle in response.
"Oh, that?" Honey said, delight marking her face. She seemed way too amused.
Tails sighed, pinching at the rose-red fabric that clung to his small frame.
"Please don't tell me you made it up..."
“Oh, I meant what I said, but I can't say much more than that. All you need to
know is that I have my ways of getting information." Honey scanned Tails up and
down for a lightning moment before turning for the door. "And my 'ways' tell me
that your pal Sonic will get a good kick out of what you're wearing right now,
if you catch my wind. Don’t worry, it'll be fun!"
Does she mean he'll laugh? He wouldn't! ...Well, he might…
"Alright… j-just a day, though."
Honey gave two thumbs up.  "Thanks kiddo, you're the best! Just one day,
honest.” Before signing off, Honey struck an elaborate, showy pose, shifting
her weight to one foot and winking, a finger pressed into her cheek. “And
remember, if you don’t look sweet..."
“...then you’re not wearing Honey- yeah, hah, I know the slogan. See you
tomorrow,” Tails said with a chuckle. The door closed shut.
The fox shook his head and sighed, tightening the orange bows that circled his
tails as he reclaimed his spot in front of the workbench. Reminding himself
that this may not actually be a completely terrible thing, he went back to
work, unswayed by the knowledge that he was tinkering around with a dangerous
prototype battery in a dangerously adorable top and skirt combo.
 
===============================================================================
 
 
"Tails...?" Sonic's face was contorted into a ridiculous grin, eyes squinted in
amusement. "Is that you, buddy?"
The fox's eyes darted to the left. His cheeks were so red he swore he was
morphing into a tomato. He dropped his wrench and faced his spiny blue friend,
who was leaning against the doorway in a bemused daze. "Yeah... I promised
Honey I'd wear this outfit for the rest of the day."
Sonic maintained his cool demeanor as he looked on with glee, but it didn’t
take long for his goofy grin to settle into a more natural expression. "It's
actually a pretty good look for you," he said, flashing one of his world-famous
smirks.
“T-thanks..” A dry laugh was the only other thing Tails could manage in
response.
 Sonic paced around the workshop, taking in an extra eyeful of his friend.
"Well, I'm not really much for fashion, but looks to me like Honey really knows
her stuff," the hedgehog said with a thicker layer of sincerity.
Tails gazed down at his feet, nudged out of position by the candor in his
friend’s voice. He initially saw the ruffled orange skirt and top, and thought
little of it upon putting it on. "Yeah, I didn’t want to admit it," he said,
smiling. “but I do feel nice.”
The blue blur did some stretches in place as he examined Tails again, placing a
hand on his own chin and furrowing his brow. Tails recognized the face. This
was the rare side of Sonic he hadn’t expected to see now of all times.
"Actually… I just got a real cool idea," Sonic said in a low voice. He
approached from the side to whisper into his friend's ear before stepping back
with an open smile. Tails caught his enthusiasm like the flu. "It'll be great!
Trust me." When Sonic said things would be great, you bet your behind that’s
what they were going to be. The guy didn’t know how to disappoint.
"Oooh Sonic, that’s twisted," Tails murmured in between giggles. "Let's do it!"
 
===============================================================================
 
 
"Sorry guys, what's up?" The door to the Sky Patrol meeting room slid open with
a faint whir as Sonic strutted in with a dolled-up Tails in tow. He shot a
knowing look at his buddy, his prideful grin unchanging.  Remember how this’ll
go.
"Sonic, when are you ever late?" Sally lowered her eyes. "And why is Tails...
in a dress?" Futile attempts were made to suppress giggles, and the rest of the
Freedom Fighters followed their leader’s eyesight, forming a collective of
smiles and grins as they turned in their chairs to face the entrance.
Sonic merely returned their gleeful gestures, unfazed. "Oh, this isn't Tails.
The guy said he had to finish up some experiments with the Tornado, so he
couldn’t make it." Tails nodded. Sonic wasn’t just the fastest hedgehog around,
he was also a pretty darn great liar. Or so he thought.
"Who is it then, sugarhog?" In clear disbelief, Bunnie sent off a smirk that
seemed to challenge Sonic's own. Though he'd never admit it he swore he could
feel his heart sink, albeit only slightly, under her unruffled eyeballing.
"Oh, this is..." He stopped for a moment, his last word trailing on as he
realized they didn’t think this through at all. By way of an exchange of eye
contact and subtle gesturing over the span of a few seconds, Sonic and Tails
appeared to communicate amidst the silence in the room and their own internal
panic.
Tails nibbled his lip, vision unfocused on the team’s relentless gazing.
Bunnie's asking for my name, Sonic! What do we do?
Sonic’s pupils quivered within their whites.  I know, that's why I'm looking at
you! C'mon Tails, I'm not good with names!
The fox blew air out of his nose, trying to give off a convincing looking
scowl.  I'm not either! Sonic, just say anything!
"This? This is M...Miley."  Wait no that’s terrible-
“Oh, well it’s sure nice meetin’ ya, Miley!”  Darn.
Poker-faced, Tails' gaze bore through the back of Sonic's head.  Miley?
With an absolute confidence, Sonic extended an open hand as he presented Tails
to the crew.  You know naming things isn't my speed...  "She's an old friend of
Tails, and...my girlfriend."
The room was hit with a strike of silence. Tails snickered to himself, barely
audible. The shine in Amy's eyes dulled.
"H-hello everyone!" the fox shakily said in his best girl-voice, pinching at
his skirt. "It's sooooo nice to meet you all."  Hey, this isn't so hard!
Hopefully I'm convincing enough.
Sally stood up, her smile gone. "Oh, I'm so sorry. You looked a lot like Tails
and I just thought..."
"Hey, it's okay~! I’m glad to finally meet you…!" Tails threw in a girlish
giggle for good measure. He was pretty certain he looked like an idiot, but no
one laughed at him so he figured he did well enough. Sonic found it hard to
remove the smarmy smirk that stuck itself on his face.  Unbelievable, buddy.
"We met up a few weeks ago. I meant to introduce her to you guys, but ah, you
know me." Within the far reaches of Sonic's mind, there only existed
uncontrollable, endless laughter. There was also some uncertainty, a
realization swiftly striking him in the gut.  I’ll give it a good 20 minutes
before Amy catches on.
"Well, allow us to give her a warm welcome aboard the Sky Patrol." Sally
cracked a nervous grin and clapped, prompting the others to follow her example.
Sonic tensed up as he caught Antoine wink in his direction, but what truly
unnerved him was Amy, who had her laser sight fixated on Tails.  Make it 5,
Sonic thought.
Rotor sat his coffee cup down on the table and gestured a thumbs up of good
will. "Good on ya, Sonic. She looks like a keeper."
"Thanks man, means a lot." Sonic pursed the edges of his mouth into a very
awkward display of happiness.
"Alright Freedom Fighters, without further interruption let's start the
meeting. Sonic, I'm trusting you to relay this information to Tails when we're
done here."
"Won't be a problem, Sal..." He used every supersonic molecule in his body to
prevent himself from bursting into a hysterical fit.
With that, the meeting began. It was short and simple, like most. These
meetings existed mostly for Sally and Nicole to keep everyone briefed on the
world’s current events. No signs of Eggman since the Dark Gaia incident, and to
the relief of everyone involved, Angel Island was in stable condition. Outside
of a few giggles from you-know-who, everything progressed normally. When it was
time for the Freedom Fighters to take their leave, Amy got a hold of Sonic on
the way out. Ever the observant one, she smelled the odd air and decided to
take action.
"Hey guys!"
Sonic knew exactly what was coming. Tails did too, and decided to wait by his
side as Amy approached them with a cheery smile.
"So you're Sonic's girlfriend?"
“That she is." The blue hedgehog grinned.
"That's funny Sonic, I didn't peg you to be the dating type."
"I'm just full of surprises, aren't I?" The tension was stabbing at him inside
and he promised he wouldn’t let it completely kill him.
Amy narrowed her eyes and turned towards the disguised fox with a smile. "Oh,
well sorry for not introducing myself earlier. I’m Amy Rose! It's so nice to
finally meet you,  Tails. "
"Er, Miley." Tails repositioned the cherry-colored bows that circled his twin
tails and placed a finger on his mouth, swaying his hips while he stood in
place.  This is a thing girls do, right?
Not one to humor over a situation like this, Amy deemed her tenacity officially
challenged. She eyed the boy dead on with an unfaltering simper. "I admire the
effort, but you're not fooling anyone, Tails." Amy had caught onto the duo’s
stunt, and they knew she wouldn’t let up until the beans were spilled. Tails
thought now would be a good time to spill those beans.
A knot formed in Sonic's throat. As long as he was around, they weren’t wasting
any beans. "You okay, Amy? This isn’t Tails, remember?" He shivered a little as
he caught Sally return to the meeting room out the corner of his eye.
"Hey Miley, I just wanted to say sorry again about-"
The pink hedgehog lifted a hand. "Sally, it's just Tails."
Sally tightened her face. "But Sonic said Tails was back at his workshop," she
pondered, turning to face the mischievous couple. "...Unless of course he was
messing with us? That  does  seem like something he’d do."
An audible gulp. "C'mon guys, what'd I say? It's Miley, my girlfriend."
"Come to think, why does she have two tails? Foxes don't just  have  those."
Sally folded her arms. "To think I was actually about to apologize..."
Sonic looked at Tails and they both beamed nervously, the fox’s twin tails
becoming inert.  Shoot! We should have thought this through.
Yeah...
"...O-oh, you see, one's fake! Tails is one of my  closest  friends, and I
always admired his two tails, so I had him make me a fake tail to wear. He's a
good guy, isn't he?"
A subtle smirk forced itself onto Sonic’s face.  Nice save!
From Amy and Sally there was a synchronized ‘mhmmmm’ and a quick sideways
glance. Amy spoke up. "Okay, that sounds pretty reasonable..."
Sonic sighed.
"...If we were  complete fools.  Sonic, why don't you call Tails on Sally's
MilesElectric? I want to say hi." This hedgehog wasn't backing down so easily,
her tenacity dangerous in that it clashed with Sonic’s own.
Tails clenched his fists, trying his best to maintain a convincing falsetto in
his voice. "Amy, is this really how you treat a new face? Sonic is my boyfriend
and I don't really like how you're denying our love like this…!" In his head,
Tails chuckled at how strongly those words came out. After that heartrending
display, he imagined his name in the credits of the sci-fi movies he and Rotor
loved so much, walking down the colorful azure streets of Studiopolis Zone.
Miles ‘Tails’ Prower, world famous actor and inventor. That’d be fun. He mused
on his words again - especially the words “boyfriend” and “Sonic” - and figured
he shouldn’t think about those words together outside of their little practical
joke.
"Whoa, you sound serious,” Amy laughed. “So, this is true after all?"
"Isn’t that what I’ve been trying to say?" As Sonic had expected out of
himself, his mouth was too fast for his brain. When Amy approached him and he
saw the interminable fire in her eyes, he understood a moment too late that he
should have put an end to their harmless little prank then and there.
Amy’s tone remained chipper. "Well Sonic, I guess you wouldn’t mind giving your
girlfriend a kiss for us then?”
The speedy hero felt his body stiffen up as the pressure stacked tenfold, his
cheesy grin remaining glued to his face. Hoping to pull clues from his friend’s
visage, his gaze shifted towards Tails while he made tiny steps away from the
exit door.  She’s got us good.
Tails fluttered his lashes in a kittenish manner.  Just do it, Sonic! Could you
imagine the look on Amy’s face?
Sally bit her lip. "Amy, isn't that a little extreme?"
Amy’s presently jovial demeanor took on a sinister aura. "Nope. If he’s telling
the truth, and this really is his girlfriend, he'll do it.” She plopped back
down in one of the briefing room chairs and invited Sally to the seat next to
her, kicking her leg up and folding her arms. “If not, he'll drop the whole
charade. Isn’t that right, Sonic?” Her eyes became cold.
Paying his crafty admirer little mind, Sonic cocked an eyebrow for one final
signal.  You sure buddy?  Tails winked, and to Sonic’s surprise, his response
came out in three words and a more familiar voice. “Do it, Sonic.”
So they did.
No more than a few seconds had passed, but Amy could merely stare, stupefied,
as Sonic pulled his friend in by the torso with little hesitation and locked
their lips together in the near-empty room. Tails became warm as he felt gloved
fingers run through his fur, and he gave in almost instantaneously. With closed
eyes and open mouths they kissed each other with a zeal that surprised all
parties involved.
Sally concealed her face with her hands, her tan fur now a subdued crimson. The
scene was something she could barely process in full while her eyes hungrily
devoured it between her fingers, and the same could be said for Amy, whose
mouth merely hung open in shock. Amy was bewildered. With what her eyes saw and
what her ears heard, she was sure this was more elaborate than that. She was
convinced she was being tricked again in some way. Unfortunately for her, she
wasn’t.
Sonic pulled away as Tails’ eyes opened little by little, noticeably
disoriented. Still within Sonic’s arms, he looked toward Amy, whose face hadn’t
changed. He sent her a tease of a message in a knowing smile, causing waves of
jealousy to ripple through the mind of the hammer-wielding heroine. “Alright,
alright, you got us.” Amy muttered, standing up from her seat. She felt a very
faint urge to break something.
“Honestly ladies, I really think you underestimated us here,” Sonic quipped,
his voice taking on a softer quality as he kept his attention on Tails. Tails
looked at him in contentment, swishing his tails slowly.
“W-well, I guess we did…” Sally’s eyes didn’t waver, and the crimson in her
cheeks refused to leave. Her halfhearted attempt at shutting down the situation
went unacknowledged as Sonic leaned in to kiss his fox friend once more, his
blood warm. The second time was even longer than the first, with Tails pushing
Sonic to the ground in his unexpected retaliation. When the hedgehog broke away
for air, Tails went back in and feverishly stamped the hedgehog on his cheek
and around his mouth.
“Eheheh… easy there...” Drunk on growing passion, the duo approached each other
and soon their tongues were twirling once more. Sonic moved his hand down to
Tails’ rear end and tugged at the skirt in a messy attempt to slide it off his
body. They parted and bore into each other, panting like dogs and smiling.
Sonic readily reciprocated Tails’ eager touch, the two paying little mind to
their observers.
Believing herself to have seen enough, Amy trudged out of the meeting room with
a firm grip on Sally’s hand. “Yeah, we’re done here,” she said, stepping out
into the hallway with a frown.
 
===============================================================================
 
 
Sally averted her eyes from Amy, who was pacing back and forth.
“I can’t believe Sonic would go that far just to spite me,” Amy muttered.
“Who knows why he did it, Amy. You and Sonic mess with each other all the time,
don’t you?”
Amy gritted her teeth. “Yeah, but this feels different. It’s like a weird
dream, or a terrible story some guy on the internet would write. It’s so… s-
so...” Her words trailed off as the scene renewed itself in her head. Vivid
images of Sonic and Tails’ passionate lovemaking grew more intrusive by the
second. Her cheeks turned rosy and she fought back her growing smile with a
tight frown. Hot. “It’s sohot,”is what she was originally going to say.
“...Ugh. W-well, it’s something I’m not in a rush to see again, that’s for
sure.” Amy was so stuck in thought that she didn’t notice Sally was halfway
down the Sky Patrol’s inner hall, speeding further and further away.
“I-I’m sorry to hear it, Amy! I hope things get better soon!” Sally shouted,
her voice echoing through the mostly-quiet interior.
Amy narrowed her eyes and sighed, dejected.  Okay then.
 
===============================================================================
 
 
“Heh, well… I guess Amy got what she asked for. You alright?”
“Y-yeah,” Tails had sputtered out, standing up.
Sonic followed suit, chuckling airily to himself as he realized the girls had
departed. “W-well, I’m cool with calling this a win. ...Why don’t we pack it
up?” His muzzle had a slight trace of red, and the discomfort could be plainly
heard in his wavering voice.
Tails shook in place, displeased. “Wait…” Bashful, he turned his focus away.
“...What’s up?”
The young fox squeezed his legs together, twisting and pulling at the rim of
his skirt as he tried to speak. “I want...” A large lump formed in his throat
which prevented his voice from traveling any further, but he was looking
forward to getting railed and that much was clear.
Sonic’s mouth creaked open and he tilted his head back a good inch, stewing in
his silence for a minute. Injected with a realization, his eyes lowered and a
kind smile crossed his face. ... You don’t want to stop either. I really
haven’t been good enough to you, little guy.  “Heh... I get it.”
He hoped he got it, anyway, otherwise he was about to look real creepy in a few
seconds.
“Y-you do...?”
Sonic carefully leaned in toward Tails, backing him against the wall. “Tails,
you should just tell me when you’re feeling like this.” He lifted his skirt by
the rim, causing the head of his stiffened cock to make a surprise appearance
from beneath the restraints of his white and red panties. Precum oozed from the
head and light, faint moans soon followed. Tails’ face grew hot, and his tongue
almost spilled out of his mouth at the sensation. Sonic’s smile took on a
wicked form.  Oh man, looks like I guessed right.
With a reddened face Sonic tugged the restrictive striped panties down little
by little before his free hand stroked at his partner down below. “How’s that?”
he said, an airy quality to his voice.
The boy squeaked and moaned under his breath. His knees were shaky, and he
swore they would give out under him any moment now. “Ah, Sonic…” Soon the light
stroking became a thorough pumping, and Tails’ cries of pleasure grew in volume
as his excitement stacked and bubbled to the tip.
Tails could only mouth words and whimper happily. “No...help me, Sonic...” It
wasn’t long before Sonic silenced him again, muting his pleas through a kiss.
He continued to pump, feeling Tails’ breath quicken and hitch as he slipped
away slowly. Tails’ whole body warmed as he approached his endpoint. He felt
like a super shaken bottle of soda, great amounts of sticky pleasure building
up inside his little body and pushing at him for a release.
“S-Sonic...I can’t take it...”
A door whirred open. “Oh, for the love of-” Sally and Amy had left but now in
their place was Rotor, whose shrunken pupils and baggy eyelids did well to show
his exasperation. His eyes were squinted away from the preoccupied pair and
below narrowed lookers was an unchanging grimace. Sonic dashed to a standing
position, his face flushing as he realized their compromising situation. Tails
jumped up just as quickly, moving behind Sonic to conceal his erection from
view and to avoid dying of shame.
Sonic spoke. “Woah, Rotor! Hey man, you see...”
Disoriented by copious amounts of caffeine and a seriously messed up sleep
schedule, Rotor lifted the mug in his hand to take a sip before speaking in a
grumble, his eyes still turned away in disgust. “Gotta be honest, I knew
something  was up, but uh… I guess I can ask the important questions later.” He
cleared his throat as Sonic balled his fingers up and flexed them,
unquestionably anxious. “Um, I’m glad you and Tails are…  enjoying yourselves ,
but please...not here.  I’m  the one who has to clean up around these parts.”
Sonic and Tails hung their heads. “Aheh… jeez Rote, how’d you know it was him?”
When he was sure the duo had concealed themselves, Rotor’s focus turned towards
Sonic. His eyebrows dropped and he spoke between brief sips of espresso. “Come
on, Sonic. Tails’ girl voice is horrible.” He managed a glimpse of the hidden
and wide-eyed Tails and hoped he wasn’t smashing his secret fantasy of
impersonating a girl or something.
Tails pressed his lips as he leaned over Sonic’s shoulder to look at him with
glassy eyes, heartbroken.  I really tried!
Sonic smiled.  Don’t worry about it.
“You guys were making faces at each other and giggling like goofballs the whole
meeting. I’m surprised Sally never caught on.”
“Eheh...r-right. Sorry Rotor,” Tails squeaked, shifting in place as his body
remained hidden behind Sonic. Unexpectedly, his joints locked up and he became
cold as he no longer moved. Frozen and mortified, he didn’t budge from where he
was. The culprit for this immobilizing wave of shame was his still-stiffened
penis, which brushed against Sonic’s rear and was almost hard enough to tear a
hole in his panties. Oh no... I’m sorry, Sonic…!
While Sonic’s eyes remained aimed towards Rotor, his ears found it difficult to
disregard the hushed groans that came from behind him and the hardened dick
that couldn’t resist jabbing him in the butt.  Aw man... Tails, c’mon!
“All good, buddy. I’m just asking that you make things a little easier on me.”
Sonic coughed for a duration, trying his hardest to mask his friend’s low,
lustful sighs. “Erm, you got it, Rotes.”
“Thanks a bunch, guys. Uh, you two have fun now.” With a wink and an honest
smile, Rotor made his exit as the door shut behind him, leaving Sonic and Tails
to a deafeningly awkward momentary silence. Rotor’s hospitality was appreciated
but he seriously made things really weird, and neither of them were as
appreciative of that.
“That was too close...” Sonic figured he should have said something sooner. His
eyes were wide and stupid, and he had an equally wide and stupid grin to match.
“J-jeez, you couldn’t wait until he left first?”
“S-sorry….” Tails fixed at the bow on his head and twisted at his skirt,
pulling himself from behind Sonic.
Sonic placed a hand down below, and the glow on his face became more than
apparent as he felt the sizable bulge through his friend’s undergarments. Tails
responded with a heavy sigh, nerves twisting. “...Why don’t we do Rotor a favor
and finish this somewhere else?”
 
===============================================================================
 
 
“I hate to bother you Nicole, but I need your help right now.” Sally scanned
her room for any unwanted visitors before shutting the door tightly behind her.
From her pocket she took out a small handheld device, and Nicole’s stern visage
lit up on the bright screen.
“What’s the matter, Sally? You look tense.”
Sally placed the handheld on a desk. If it wasn’t already clear, her priorities
were very skewed. “I heard them, they’re heading down the hall to Tails’ room.
I’m going to need a live feed  right now. ”
“Is there an intruder?”
“No, no…” Sally laid back as Nicole projected a hologram of the camera view in
front of her eyes. She saw a still dressed up Tails walk into his room with
Sonic behind him. As soon as the door was closed, Sonic back himself against
the mattress, pulling Tails close. The audio came in crackly and muffled. “Oh,
Sonic...”
“Oooh...this is too much,” Sally moaned, tugging at her shorts. “N-Nicole,
enhance the stream...”
A tiny blush could be seen on the AI’s cheeks through the screen. “Sally, I
really don’t know if you should be using the Sky Patrol’s security cameras to
spy on Sonic and Tails like th-”
“Enhance it.”
Unfortunately, Nicole’s further protests went unheard as they were drowned out
by a sequence of moans and sighs. “Sally?” Frustrated and confused, she snapped
her fingers and the picture’s quality increased pixel by pixel, static
vanishing from the feed.  “S-Sally…?” The lynx’s attempts to get her friend’s
attention went ignored. She could do little but look at the aroused and
inattentive Sally, whose heavy eyes had a trancelike focus on the camera feed
as frantic fingers rubbed and dipped away at her moist lower lips.
Intrigued, the lynx girl turned her attention to the stream of Tails’ room.
Sonic was kissing Tails up his tummy while he giggled and sighed, his panties
pulled off of his legs entirely to fully expose his erect penis.  I’ve never
seen Sonic and Tails do this before , Nicole thought to herself.  Why would
such activities appeal to Sally this much?  Her eyebrow lifted as she mused on
the view.  Perhaps an extensive investigation should be conducted...
 
===============================================================================
 
 
“Ahah… Sonic, stop that!” Tails cried, whimpering as Sonic kissed him still.
Sonic moved down to the head of Tails’ cock and proceeded to slowly lap at the
fluid that seeped from it. Tails shuddered happily as his prickly pal met him
face to face. If the lusty little fox had to describe how he felt right now,
one word would come to mind, a  rigid  and  stiff  little adjective -  hard .
He was hard, beyond it even. Very hard, as if the firmness of his cock was
somehow held by a thin steel beam, with said steel actually being some sort of
reinforced uber-diamond. Existing as he was at that point - with his messy
climax nowhere in sight - almost crossed the border into torture. Almost.
“So… Honey wanted you to wear this?”
Tails opened his eyes. “Y-yeah… she said you’d love me in it.”
Sonic lifted the tangerine top and exposed the white furred tummy hidden
beneath. Slowly he planted a kiss on his fluffy midriff. “Well I gotta say it
again - that cat really knows her stuff,” he said, cheesing. Many wouldn’t
think it, but Sonic really knew his stuff too.
Tails was set to open his mouth before Sonic restrained him with a powerful yet
brief kiss. He briskly felt the fox up his body, tugging at his clothes. Sonic
pulled his mouth away again, leaving a string of saliva between the two as
Tails panted for air. Sonic backed off, then dove again. His penis pressed
against that of his buddy as Tails faced him from below.
Tails thought back to earlier that day.  I'll have you know I picked this
outfit for you because I was confident a certain blue hedgehog was bound to
love you in it.  That was what he heard her say - and love him Sonic had so
clearly did. The hyper-quick hedgehog indulged in his partner like a hungry
dog, nibbling lightly at his shoulders and kissing him tenderly on the lips.
His hardened cock brushed against Tails’ own during the occasion, inciting
hitched breaths. Sonic rolled his eyes away, blushing as seminal fluids began
to seep from his own erect penis.
“S-Sonic?” Tails was thrown back by the carnal yet gentle beast that had
replaced his friend. Eyes unfocused, Sonic backed himself off, aroused beyond
his own belief.
Stricken with an impulse, Tails broke from his vulnerable state and swapped
with Sonic, splaying his body out against the bed as he pulled his panties back
up. He eyed Sonic’s stiffened penis and creeped up on it, placing his tongue
below it and panting. Unafraid to display his docile sensibilities in full to
his spiky partner, his ears drooped as his eyes rolled up towards Sonic’s own.
“W-woah…!” Sonic clenched his teeth as Tails’ warm breath engulfed the head of
his cock. Soon Tails was eagerly sucking at the tip, prompting the hedgehog to
grip the sheets below him as groans emitted from between his tightened lips.
Sonic’s face grew warm. He repositioned his hand to guide Tails’ head, and his
body tightened as the remaining length of his erect penis vanished from view.
“Aghh…”
From the beginning Tails was persistent, closing his eyes as he sloppily
suckled away. Saliva seeped from his mouth while he bobbed on Sonic’s cock,
viscous fluids coating the back of his throat. He tasted at his friend’s girth,
trapped in a lust-fueled daze. Sonic tilted his head back and groaned.
Restraint was a thing he rarely ever liked to use, but he called upon that
control now to keep himself from crying out as Tails pleasured him
enthusiastically.
Tails’ eyelids lowered, his tongue pressing against the bottom of Sonic’s
length to cover it with a thin layer of saliva. He went down slowly, then back
up, licking at the head again before being pressed back down onto it with a
muffled “mmph”. Sonic’s tongue rolled out as Tails kept his pace, his body
ready to give out right then and there. After a good minute, Tails moved off of
Sonic, freeing his penis before twisting around and sticking his bare rear out
with a pliant look. “J-Jeez…”
If Tails had a little more fortitude he would have patiently waited to see what
Sonic had in store for him. He had none now, and so he shook his tails in
Sonic’s face again, desperately craving his end with the friend he cherished so
dearly. When a few seconds passed and there was still nothing inside him, he
resorted to words. “Sonic…?”
“I have a way better idea.” Sonic gave a command and Tails did what was told,
facing tummy-up, and Sonic mirrored his position, to the point where his balls
and penis were lined up against that of his partner. Now lying opposite each
other with their cocks pressed together, Sonic wrapped his hand around them
both, his touch sending a powerful current of electric signals through Tails’
body. “You can handle this, right?”
“Y-yeah…”
Sonic kept a loose grip around both of their erect penises and began pumping at
a moderate pace. He could feel Tails’ erection throb against his own as he
pumped, which was exciting. It didn’t take long for Tails to start moaning
either, which was even more exciting. Sonic became weak and eventually he gave
in to himself and his buddy, groaning on the off-beat. “Hnh…”
Tails’ control expectedly slipped away from him and soon he was spiraling into
joyous, pleasured sighs and coos right along with his partner. His body was
boiling, and it was clear being so close to Sonic like this was an otherworldly
experience. Sonic felt the same, and he himself struggled to even think
straight through his hitching breath. He slowed down briefly, sliding his
fingers up and stopping to give a delicate squeeze, causing precum to seep out
from the two and moisten their touching heads. The thin fluid made a fine
lubricant, and with each grope there was an assortment of little sticky sounds
as their lengths rubbed against one another.
“Sonic… not yet...”
Abort! Sonic stopped his hand and became limp, exhausted already. They laid
there for a good moment, sighing. Tails wanted to finish, but not in this way.
That much was clear. So Sonic sat up, straightening himself and grinning. “Why
not?” he said, an index finger now on Tails’ shaft. Sitting upright now, he had
a proper view of his friend after their moment together. Tails looked up at him
with pitiful, shining eyes, barely moving as Sonic held him at his mercy. The
tufts of fur on his chest pushed his top out as he breathed, and his face was
sweaty.
“What’s wrong, buddy? Are you sensitive here?” Sonic thumbed the head of Tails’
penis a few times, and was rewarded with a lovely and amorous melody of moans.
On Tails’ drooling face Sonic found more words.
Yes, yes I am…! Please stop!
“That’s kind of crazy, huh? I mean I’m not doing much…” His tongue released
itself from his mouth and veered ever closer to Tails’ most sensitive area,
threatening to attack him with a good lick or two.
Yes you are! I can’t take it, Sonic!  Tails tried to speak but he only managed
a “S-stop…”
Sonic’s voice softened and he looked directly into Tails. “Why would I stop?
That’s kinda lame. Besides, does it really matter if you…” He dragged this word
out a little, his tongue lapping at Tails’ tip. “ ...cum?”
HNNNH...
Tails shut his eyes, ready to explode like a lewd hand grenade just waiting to
have its pin pulled. “N-no…”
Sonic decided to give him a break. “Alright, I’m done messing with you, bud,”
he laughed. “Why don’t we finish it?”
Tails laid there panting for a good few minutes, but once he had regained
control he flipped himself over and jutted his rear out again. He  really
wanted this.
Frankly, after all he’d endured, with his skirt hiked up and his bare ass aimed
towards Sonic’s face, Tails felt too vulnerable, too excited, and too hot to
generate any sort of response past ceaseless, hushed moaning. The boy’s body
ached. His twin tails dusted at Sonic’s chin, almost as if to tease him for not
immediately taking advantage of the round, squishy opportunity presented to
him. Tails had no spoken words, but as things usually progressed between the
two, his actions made a more effective statement. He batted his eyes and looked
back, wiggling his butt again.
It took less than a moment for Sonic to come to terms with his erection and
slip himself into a comfortable spot between Tails’ cushy cheeks, lifting the
skirt a little more. With a grunt Sonic pushed in slowly and gently, Tails
gasping. Then he started. Once in...once out...in again...out again. Tails
echoed Sonic as he blushed and whimpered, his stuffed rear end jutted high in
the air as the upper half of his body wearily flattened itself against the bed.
The initial five motions were slow and had a strange grace about them, which
was fine - they were just getting started, after all. But the sixth time in was
what threw the oversexed and overstimulated Tails for one hell of a loop,
because with the sixth hit there was a series of grunts as Sonic’s body picked
up absurd amounts of speed over the course of a few seconds. Soon he was four
times in. Then six. Then ten. Fifteen, twenty-five, thirty-eight, only getting
faster from there.
Initially open and wanting, Tails learned nothing could have truly prepared him
for the supersonic smashing Sonic would swiftly deliver to him. His words were
forced out of his lips between gulps of air. “Hnh….S-Sonic...”
Shame slapped the hedgehog in the face and spat on him, and he immediately
dropped his speed respectfully. “S-sorry buddy…” His thrusts were a gentler and
kinder pace now. Tails loosened over time. He shivered delightfully as Sonic
pressed into him, a myriad of sensations about him: a tingling and a twitching,
among others. The moment itself was surreal, and his own thoughts struggled to
maintain their presence.
Any boldness Tails may have had was gone, thoroughly melted away as he put
himself at the hedgehog’s mercy. Sonic blushed as he realized what he was
doing. There wasn’t any reason to deny anything - he was horny as all get-out.
And he wanted to go  as fast as he possibly could.  But he remembered how rough
he was at first, and promised he’d do his cuddly companion a kindness. So he
made sure he started out gentle. He was careful at first, but whenever he was
certain Tails was comfortable, he’d crank up the speed in minute amounts.
“Ah, Sonic…!”  Throughout it all Tails moaned Sonic’s name like it was the only
word he knew. His elated, honey-dipped cries were a sweet signal that served to
stimulate Sonic further in his fervor. The feeling of Sonic thrusting inside
him was fulfilling to him, like it met some strange life urge he hadn’t
realized until now. Tails could feel Sonic’s cock throb and thicken deep within
him, and it drove him wild.
As Sonic sped up he felt himself approach a limit .  Though he didn’t want to
drag things out any further for Tails, he was unsatisfied with the possibility
of going out like this. He followed his good judgement and pulled himself out
before he could let loose. Tails, still pressed against the bed with a boner
and a grin, sank in mild frustration when he felt Sonic exit him.  So close…
He was naturally surprised when Sonic eagerly put himself back in, this time
pulling Tails on top of him. “W-whaa…” Sonic kept his motions but this time as
he thrusted he held a firm hand around Tails’ cock and jerked it slowly. Tails
just nearly lost his mind, his consciousness really to splinter at this point.
There really weren’t any words, only elated cries and helpless panting. Tails
stuck his tongue out, sweating and trembling. The poor soul was flooded by his
feelings, clinging hopelessly onto his sanity as everything he ever had swelled
to the tip of his penis.
Gratification was the name of the game, and Sonic was certainly gratified. He
was eager to please and so he kept his pace consistent in its quickness,
despite a burning desire to go beyond. True to his style, he was marking ahead
when he wasn’t even sure if he could run that far. Any quicker and he felt he
would pass out, or finish too early. It was an overall wonderful feeling, his
length snugly sliding in between soft yellow mounds.
“Nnnh…. Tails…” What Tails didn’t count on as he felt the tightening warmth
inside him was that Sonic would be the first to go, having just barely held
himself back through their time together. That seemed to be enough for him.
“S-Sonic…!” When Tails followed, he came strong, spurting with the unexpected
force of a geyser as he dotted the duo with his seed. His eyes watered and cum
shot from him in short intervals as he whimpered, almost ready to break into
tears. For a time his body was a conductor for a mighty lightning bolt of
ecstasy, which bounced around inside him and left him now, these orgasmic
energies accumulating to this moment.
Sonic withdrew and fell flat onto the bed, a smile on his face. Tails flattened
himself next to Sonic, his breath slowing. They turned to look each other other
and then looked back up, and it took a good 5 minutes before anyone actually
said anything.
Tails was staring at the ceiling. “Sonic…?”
Sonic was too. “...Yeah, buddy?”
“Amy’s going to be really mad.”
Eyes warm and friendly, Sonic turned to give Tails the sacred and forbidden
Grin of the Shit-Eater. “...So?”
Tails smiled.
 
===============================================================================
 
 
“So Tails, how’d it go...?”
“How’d you know?”
“Hmmmh...you first?”
Tails turned into a tomato again. “You were right, he was really into it and…
well, I was really into it too, and uh...”
“W-woah, I bet you had fun!” She placed a finger against her lips, as if to
prevent herself from letting anything slip. Tails had an inkling that Honey had
some sort of treasure chest hidden somewhere in her mind, locked behind the
marked outer layers of opportunism and raw spunk. A treasure chest that
contained all sorts of crazy life secrets, ones that went much further than
just “put on a cute dress and you’ll get laid.” She just seemed like she knew a
lot about things like that.
“Uh…yeah… but how’d you know he’d get… different over me wearing this?”
Honey struck her signature pose. ”Well you see kiddo, that’s just my
businesswoman’s intuition at work~”
Tails cheesed, placing a screwdriver on his work table. “For some reason I
don’t believe that.”
“...Yeah, you shouldn’t.” The cat snorted with laughter. “It was just a really
lucky guess.”
Hmmh.
“I had an inkling you wanted to appeal to him though, and I was right, wasn’t
I?”
Tails’ stupidly book-like face said yes. Honey skipped a few chapters ahead.
“So I suppose you’re going to ask if you can keep the dress?”
“Huh?”
“That’s what you’re going to ask! You were thinking about it, at least?”
“Maybe I was…” Tails twiddled his fingers together. “You did a great job.”
Honey shooed Tails with her hand, blushing. “Aww, I try.”
“So...can I?” He wasn’t even sure if he was really comfortable with holding
onto it. He would still have to explain to everyone that he’s not a girl and
deal with troublesome things, like Antoine’s tears and Bunnie’s divorce
paperwork.
 “Of course, of course. On my end, we call that a ‘pocket promotion’. But.”
“But?”
“I have a better question.” Honey’s tone turned earnest. “Do you think you’ll
actually need it?”
“Huh?”
“We both know how Sonic can be. Think about it. Maybe he’s always wanted to get
closer to you. So maybe your totally fashionable top and skirt combo was more
of an excuse to finally do so. You  know  he cares a lot about you no matter
what you wear.”
Tails’ gaze fell towards the floor and he smiled. “Yeah… you’re right. Thanks.”
“It’s nothing, really.” Her words were an undeniable kindness to him. “Now if
you’re feeling as generous as I am, I’ve got one teensy favor to ask of you.”
“Oh sure, shoot!” Tails couldn’t be more willing right now.
Honey leaned her face in as close to Tails’ as possible, piercing into him with
a Cheshire grin. “You and me, kiddo. Sonic was just round one.  I’m  round
two.”
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