Fox hound

Charlie's eyes beaded with tears as he writhed underneath you. "Please!" he gasped. "I can't take another one!"

"Awwh, pretty boy…" you cooed down at him, tone full of fake condescension easily betrayed by the mischievous malice glinting in your eyes. "I don't recall asking if you could take another, I recall telling you that you would.

He sniffled pitifully, a balled fist going to wipe at one of his teary eyes, before meeting your gaze again. "Please…" it was barely more than a whisper now.

Ignoring his pleas, you simply hummed before starting the soft, feather light touches against him. A finger circled the red, swollen head of his cock, which spasmed underneath your ministrations. You changed course, running your hand underneath his cock to palm at his balls. Charlie had cum dry twice already, but just because they'd been emptied didn't mean they were immune to sensation. A garbled moan slipped out of his mouth.

You glanced down to see Charlie, red in the face and lower lip trapped between his teeth. He worried it between them almost to the point of biting through it as he let out sounds that weren't quite appreciative but weren't quite tortured yet.

Well you couldn't have that…

"Baby boy," your tone was firm, but not upset. "You're supposed to let me hear you. I know you know that," You reached out and gently swiped your thumb over his ruined lip. He released it slowly, gazing at you almost in trepidation. Not wanting him scared of what was coming, you leaned down and pressed a kiss to his raw mouth. He groaned gratefully into yours, before reaching a hand up to grip at your waist like a lifeline. You had told him no touching earlier, but in a split second decided to allow this. Charlie clung to you as you dragged your tongue across the tender skin of his bottom lip, mouth falling open in submission. You hummed gratefully as he granted you access, using the opportunity of slipping your tongue into his mouth to deftly reach downward and cup his balls again.

Charlie started against you, but didn't protest past a soft mewl that you quickly swallowed. Tiny noises left his throat as you caressed and tugged until he started getting hard again. You finally turned your attention to his neglected cock, and Charlie broke away from your mouth to moan loudly. "Good boy!" A warm pride swelled in your chest at the sight of your boyfriend opening up for you, and you didn't resist the overwhelming urge to push his hair off his sweaty forehead, despite how uncomfortably sticky it was.

He blinked slowly at you, blush spreading up his cheeks. You gave his cock a few gentle tugs, until the poor thing was fully hardened under your fingers. Charlie winced, but his eyes betrayed that through the pain he was also finding a great deal of pleasure. You smiled reassuringly at him, and began to stroke at a smooth, slow pace. Your hand and his cock had already been covered in cool lube to avoid rubbing him too raw- and you were grateful for it now as you slid up and down his tired shaft with ease.

Charlie shook slightly under you. "'M not going to last long…" he whispered, embarrassed.

"That's okay, darling. Let me see you come undone," You quickened your pace ever so slightly, twisting your wrist as you focused all your energy on getting Charlie off.

Mere moments later, his dick began to twitch in your hand. "Oh fuck, fuck fuck fuck," he was murmuring above you, but you didn't break concentration, wanting only to milk him through one more orgasm. He let out a choked yelp as he came, a single bead of cum gathering on his tip as he shuddered and shook. You gratefully licked it up, and Charlie let out a whimper at the contact, before you gently released him, finally making eye contact with him again as his lids began fluttering closed.

Charlie was speechless, his palms sweating into the material of his jeans.

The two of you had been sitting on your couch watching a movie, completely innocent, until you’d brought up the fact that you were going on a date the next day.

Your first date ever.

“You wanna…”

“Please? I just- I don’t want to tank my first date because I’m inexperienced.” You pleaded, your body turned to face him completely.

Charlie was your best friend.

You’d known each other since sophomore year of college, being practically inseparable ever since, even becoming roommates after graduating around a year ago.

And for all those years that he knew you, never once did you mention your dating life.

He supposed this was why.

He felt stiff next to you, not uncomfortable, just processing. “And so… You want me to…”

You frowned, burrowing your face in your hands. “Please don’t say it again, I already feel weird.”

“No! It’s not…” Charlie stammered, struggling to find what words he really meant. “You don’t need to be embarrassed… I just…”

He didn’t want you to feel bad.

It was flattering, if anything, that you trusted him enough to even ask.

And it’s not like he didn’t want to kiss you…

He did.

He really did.

And maybe that was the problem…

But when you were sitting across from him, eyes big and pleading, how could he ever find it in himself to deny you?

“Just to practice?” He asked softly, glancing at you nervously, his teeth chewing on the inside of his cheek.

You nodded frantically, scooting closer to him like a nervous puppy. “I would also appreciate… Tips.”

He chuckled, almost in disbelief at how open you were being about this. “If it won’t… Make anything weird-“

“It won’t, scouts honor!” Your hand shot up, your open hand facing toward him.

Charlie grinned, reaching for your hand and folding your thumb and pinky finger into your palm to form an actual scout’s salute.

His touch was warm in your hand, lingering for just a moment too long.

“Okay.”

“Really?” You released your salute to grip onto his hand, something you would do often, grabbing his hand to reassure him or ask for his help.

He’d originally seen it as an innocent gesture, just something you did with all your friends, but when you were holding his hand asking him to kiss you, asking him to take away your chance for a real first kiss, he wasn’t so sure it was completely innocent anymore.

“Yeah.” Charlie’s tone was low, not realizing how close you’d gotten to him until then, glancing at your lips. “I’ll help.”

Your heart skipped a beat.

You really didn’t think that would work.

But here he was, your best friend, ready to kiss you.

And as he leaned in, lips parting slightly, you closed your eyes and felt fireworks explode from your mouth, back to your cheeks and brain, blood rushing to every inch of your body.

Your hand twitched and tightened your grasp on each other.

Charlie’s lips were so soft, tasting like strawberry jelly, the donuts you’d eaten together just mere minutes ago.

You couldn’t move, couldn’t breathe.

Until he pulled away.

You nearly chased his lips, but took a deep breath instead.

Charlie grinned, a small smile that made his dimples obvious. “Breathe through your nose.”

You brought a hand to his shoulder, gently dragging him back to your lips, which he accepted.

He smelled like home, like comfort and joy.

You supposed you’d never noticed it before.

How he smelled.

Other men would wear colognes, musk mixed with spice or something oddly vascular.

But Charlie smelled vaguely of citrus, just the beginning hints of it, enough to recognize the smell but not enough to really identify it.

Every time you kissed him you felt something new.

A new depth of him that you’d never gotten to experience before.

But you wanted more.

So you pulled away.

He could see you getting frustrated, a look of upset in your eyes.

“But… How do I…”

He just grinned at your impatience. “I’ll show you…”

Your body shivered at his words.

“Open your mouth a little…” He whispered against your lips, waiting for you to do so before he pressed back into you.

His instructions made your mind race, you wanted him to teach you more, to tell you how to do everything just the way he liked it.

When your tongues touched it felt electric, causing you to jump slightly, before falling into a rhythm that made too much sense to pull away.

It felt so right, his familiar touch, his newly-familiar taste.

A tingling fell to below your chest, seating deep in your core.

Your thighs clenched at the sensation, giving only the smallest gratification to your clit.

You were so wet, you could feel it underneath your skirt, on your soaked panties that pressed against your thighs.

His tongue in your mouth was the only thing you’d ever imagined when pleasuring yourself.

When he pulled away, you knew you’d be chasing that feeling for the rest of your life.

But you could have it right now if you wanted, it was inches away from you, Charlie was right there to provide.

So you slowly leaned in to kiss him again, Charlie’s eyes fluttering shut as your lips met again.

He groaned into your lips as you climbed into his lap, straddling his hips and continuing to kiss him.

Charlie’s hands hovered just inches away from your waist, twitching with want, until he caved and cupped your body like it was breakable.

His own brain was melting, everywhere you touched felt like it was on fire.

He had to fight tooth and nail to keep his hands from lowering onto your ass.

This was just supposed to be practice, right?

But he gasped when you’d brushed against something hard beneath you, causing you to pull away, wondering if you’d done something wrong. “Sorry, I just-“

He didn’t have the words to explain himself, why he’d gotten hard at his best friend kissing him.

But you didn’t give a damn.

“Will you teach me?” You whispered to him, rubbing your clothed core on the hard print of his dick in his jeans.

Charlie’s brain nearly short circuited at the request. “Teach you… What?”

You thought for a moment, before you grabbed the hem of your shirt, rolling it up and off your body.

You wanted for him to see all of you.

To gaze at you through those eyes you’d tried so hard not to stare into for any longer than necessary.

You’d just felt so wrong, imagining him touching you, kissing you, fucking you…

You weren’t really sure how you actually felt about him.

Maybe you had a little crush on him and all of this talk of “inexperience” was just your way of creating something between you two.

A desperate attempt, you would admit.

You’d imagined him taking advantage of you in the smallest ways during sleepovers, watching you change through the door to your bedroom you may have intentionally left open just a crack once or twice.

Or catching him staring at the pair of slutty panties you’d one time left on your floor of your room just so he would see them.

One time, you’d thought about cuddling up to him during one of your sleepovers and rubbing your ass against him to egg him on, but you didn’t.

You just wanted him to do something.

But he didn’t.

He was just so nice.

So caring.

Completely respectful of you and your personal space.

But you didn’t want him to be respectful anymore.

You wanted him to want you as much as you wanted him.

Charlie’s eyes dilated at the sight of your tits, cupped in a cute little bra.

“Teach me how to make someone feel good…” You pleaded, your face flushed and hot.

Charlie opened his mouth to object.

He had definitely taken this too far.

He’d wanted you so bad, he’d managed to push aside any feelings to help you.

He just couldn’t do this with you if it wasn’t him that you actually wanted…

But how could he stop when you were practically begging him to keep going?

So Charlie’s hands released your waist, slither down between your bodies and unbuckling his belt.

You watched as his fingers unzipped his fly, opening his jeans to reveal his boxers, simple and black, before he pulled his cock from the confines of his clothes.

You felt your pussy flutter around nothing, the ache in your core getting stronger.

“Take your… Your hand.” Charlie stuttered, obviously embarrassed that he was exposed like this, but still trying to keep his cool.

He gripped your wrist, bringing your fingers slowly to his tip, flushed and leaking.

You shuddered at the feeling of a cock in your hand for the first time.

And not just any cock, Charlie’s.

He was smooth, but hard, the stiff muscle beneath the skin twitching at your touch.

He was breathing harder than you’d ever heard him before, practically panting as you experimentally circled over his slit with pre-cum beading over it.

“Just uh… Hah… Go slow.” Charlie mumbled, his gaze trained on your hand as you stroked him slowly.

The rasp in his voice made a warmth form in your brain, sliding like honey down your spine.

Your wrist turned around him slowly, pumping him up and down all the way down to his base.

“Squeeze tighter… I can take it.” He grinned, licking his lips and glancing between your legs.

In your passion, your skirt had managed to ride up on your thighs, revealing the slightest view of your panties to him.

They were soaked, darker in the middle where your pussy had drooled all over itself.

You followed his instructions, tightening your grip on him and speeding up just slightly.

“Fuck~” Charlie’s head fell back, letting out a groan at your movements. “Yeah, just like that.”

You felt your chest heave, watching him struggle to keep sounds down.

It wasn’t fair, you wanted to feel good too.

So you took your hands off him.

His head lifted to look up at you, eyes foggy and out of it. “Why’d you stop?” He slurred out, a hand moving to grip your thigh.

You whimpered with guilty eyes, so sensitive to his touch, which made his eyes widen.

“Oh…”

“I still haven’t…” You struggled to get the words out.

“And… You want me to…”

You nodded bashfully.

You wanted it to be him, needed it to be him.

You felt so safe with him.

You couldn’t imagine anyone else you would be willing to go this far with.

Both of you realized then that this wasn’t for practice anymore, but for your pure lust.

Charlie knew you hadn’t had sex yet.

It was one of the many things he teased you for.

But to hear it straight from your mouth when you were begging for his cock…

He wanted to fuck your virgin pussy and ruin you for anyone else.

You’d been such a whore in front of him so many times.

Every dirty thought he’d ever had toward you could finally come out to play.

Charlie’s fingers dug into the meat of your thigh. “You want me to fuck you?”

You nodded desperately, shy, yet so fucking horny.

He couldn’t resist, shoving his hands between your legs and moving the middle of your panties to the side to see the pretty little cunt that was so hungry for his cock.

Shit, he’d imagined what your pussy would look like for years, but nothing could compare to the real thing, so cute and wet for him.

He thought about having you bounce on him, but it just wouldn’t be enough.

Charlie needed to be so deep inside you that you would feel him for days afterward.

He needed to corrupt you, make you feel so good you’d never turn to someone else ever.

Turn you into such a cock hungry slut, you’d want him all the fucking time.

So he gripped your hips, flipping you around so you were on your knees for him on the couch.

He flipped your skirt up, moving your panties out of the way completely, and kissed your entrance with his tip.

“You want me to take your virginity?” He asked teasingly, moving half of the head of his cock in and out of you.

You breathed heavily, moaning and wiggling your ass at him. “Please, Char~ Fuuuck!”

Your pleads were cut off as he slowly sunk inside you.

It hurt a little, the pain only turning to pleasure when he stopped at the hilt, completely balls deep in you.

It was such an intoxicating feeling, having your best friend inside you.

“God, you’re so fucking tight.” Charlie moaned, trying an experimental movement of dragging out and slipping back in.

And it was so fucking easy cause of how wet you were.

So he thrusted harder, faster, making you whine even louder.

“Feels good?” He whispered to you, leaning down to grip your arms, pulling you back onto him vigorously.

You gripped his arms in tandem, pulling yourself back onto him. “Ooh~ yesss~”

“Practicing, my ass.” Charlie growled out, forcefully thrusting into you enough to punch the air out of your lungs. “You just wanted me to touch you like a little slut.”

You moaned in response, smiling wildly.

You knew it was true, every time he would tease you or make fun of you for being a virgin you’d have to restrain yourself from jumping his bones then and there.

Cause you knew he would be so nice and let you fuck him.

But if you knew sex would feel this good, you would have propositioned him so long ago.

“You’re all mine.” Charlie mumbled deliriously. “Pussy’s all mine…”

You felt so helpless, his iron grip on your arms releasing, sure to leave the most delicious bruises.

His fingers trailed around your body to grasp your tits, still sitting pretty in your bra, before he tugged it down and freed them, wrapping his big hands around them.

“Char~ Charlie~” You moaned, feeling him switch angles and pound up into a spot that made you see stars. “So deeeeeep! Aahh~”

“Yeah? Did I find your spot, baby?” He asked, pinching and tugging on your nipples. “Are you gonna cum?”

You nodded frantically, making him growl out a moan, going even harder and fucking into you with a fervor that only Charlie could give you.

“Ohhh fuuuuckk~” You cried out, grabbing the hem of his shirt and pulling him into you as you came, squirting everywhere on shaking legs, your pussy fluttering around him.

He let out a groan, his legs shaking as well as he pumped into you, cumming in tandem.

Your cum dripped down your legs, his balls, even the bottom of his shirt, the green fabric wet and smelling of sex.

Fuck, the whole room probably smelled like sex.

You finally could say that, too, knowing what that meant.

He pulled out, making you shudder, and laid down, bringing you into his chest.

“You should maybe uh… Cancel that date tomorrow…” Charlie chuckled under his breath, pressing a kiss to your temple.

you made a lot of noise in your sleep, so honestly, wilbur didn’t think much of it at first.

wilbur could always tell when you were dreaming- those nights he’d be wide awake but you were asleep against him, your lips twitching upwards into a small smile or your lips frowning, hands grabbing his arms when you were having a nightmare.

you’d stumbled over to wilbur’s place after work, tears in your eyes and exhaustion settling in your bones. you collapsed into his arms and you cried it all out, rambling to him about mean customers, how you spilled drinks all over your clothes that you had to wear for hours, how you felt sticky because it was humid in the restaurant you worked at.

after letting you use his shower, you’d come out wearing one of his big sweaters and a new pair of underwear that you’d brought weeks ago in case you ever needed them (and found them shoved into the back of his pants drawer in the dresser, he genuinely had no idea they were even there).

wilbur hasn’t slept all night. his eyes were exhausted, but his body refused to let him sleep. his arm was snug around you, the other tapping against his stomach through his worn out sweater (the same one you could tell he’d rot away in on those weeks it got hard to get out of bed and take care of himself or nights he simply couldn’t sleep).

wilbur could tell you were dreaming. your eyelids were fluttering, your lips were twitching up and your breathing was slightly heavier than normal.

but then he felt a slight rocking against his thigh. and the soft hums from your mouth were turning into quiet moans. he had to look down to make sure he wasn’t imagining this- but he wasn’t. and there you were, dead asleep, humping his thigh almost so carelessly.

wilbur wasn’t entirely sure what to do in this situation. you weren’t even giving him the ‘okay’ to do anything. in fact, you two had never been intimate. you guys enjoyed cuddling and watching movies. and he wouldn’t deny that he had thought about a moment like this before, or kissing along your neck while he fingered you, but now that it was happening… well, he froze up.

but that didn’t make him push you away. instead, he wanted you to keep going.

you adjusted so your hips moved quicker against his thigh, fingers trembling as they clutched his arms. and he pushed his thigh between your legs harder. you let out a tiny squeak, and he could feel your cunt throbbing. and all he could do was hold you closer, helping you get closer and closer to your finish.

and there it was… your hips spasming, mouth open and hole fluttering. wilbur felt his dick grow hard as you came on his clothed thigh, and before he could hide it from you, your eyes slowly fluttered open.

fuck… fuck.

it took you a few seconds to gage your surroundings, hips still rocking just barely, eyes sore from sleep and lips slightly puffed out. but the wet patch in your underwear caught your attention, and when you pulled back on his thigh and looked down, you saw the wet patch… and it clicked in your head.

“oh… i’m- uh… i’m so sorry…” you said, cheeks burning with embarrassment. “don’t… don’t even worry… uh… it was kind of hot.” wilbur admitted, gulping nervously as he helped you off of his thigh, rolling over to hide his hard dick from you.

but you noticed.

“wilbur…” you spoke out softly, laying on your back. “yeah?” he asked. “have you ever… i don’t know. thought about us?” he paused for a second at your question. “yeah, i mean, i’m thinking about you all the time.” “no, i mean… like, us fucking.” you inquired. he bit his lip, deciding what the right answer was. “uh… yeah. i suppose. maybe a couple times. why do you ask?” “i… i don’t know. i wanna try it… i think we can do that, right?” you watched wilbur roll over, his bulge visible to you now. “i guess… yeah. i mean, why not?” he suggested nervously, crawling closer to you, shaking fingers hesitantly slipping into the waistband of your underwear and sliding them down.

your underwear dangled from your ankle, eyes on wilbur as he untied the string on his pajama pants and slowly pushed them down, his dick hard and the tip wet. “so, uh… do y’wanna do this facing eachother or… or you facing the other way…” he asked. “uh… i’ll face the other way…” you responded, turning over in the bed, hesitantly spreading your knees and arching your hips up. wilbur felt his breath hitch in his throat before coming closer, taking his dick into his hand and testing your hole by pushing his tip in and out. he almost moaned from how wet you felt.

“are you, uh… ready? o-or do you need a minute?” he questioned. “no, ‘m fine…” you assured. slowly, he pushed in, a soft gasp escaping his lips. you quickly shoved your face into the pillow, face hot with embarrassment from how fucking good this felt, but also at how big he was. wilbur wasn’t grotesquely big, but he certainly wasn’t small either. he was filling you so nicely, and all you could do was lay there and take it.

“ahh… wow…” wilbur breathed out, a huff of air coming from his mouth as he bottomed out, one hand on your back and the other holding his shirt up so it didn’t get wet. he stayed there for a moment, making your hole flutter from how full it felt. his hips shifted, his dick dragging in and out of you slowly. your hands grabbed onto the pillow below your head as you reveled in this feeling. fuck, you haven’t been laid in so long.

it was almost involuntary when your hips began moving back against his, begging for more. wilbur took the hint, hips moving steadily. he wasn’t sure if he was gonna last long… but honestly, you couldn’t even complain if he did cum fast.

the pleasure shot through your stomach over and over. you felt your thighs growing sore, threatening to give out. his hips pressed against your ass so nicely everytime he bottomed out. and this is exactly how you pictured it everytime you did- on his bed, him fucking you from the back.

it was hard for you to move, and in all honesty you had no desire to, because he was hitting the right spots. he sure seemed to know what he was doing; and on any other day, you’d feel jealous at the thought of him doing this with other girls, but right now, all you could focus on was his dick in you.

wilbur’s hips moved with more urgency, it was obvious he was close to cumming. his hands pushed down against your back, soft whimpers leaving his lips. his eyes were softly closed and he finally opened his mouth to speak. “fuck… fuck… ‘m gonna cum… ah-“ he gasped out, quickly stilling in you as he came. he thrusted a couple more times before slowly pulling out, his dick slapping against your back once. he sat back onto his knees, releasing his grip on your back as he breathed shakily.

“ahh- shit, did you not cum?” he asked. “no, not really.” you admitted, resting your sore legs down onto the bed. “oh- sorry…” he responded sheepishly. hesitantly, he reached a hand down and pushed it into you, curling his fingers on your spot again. you spread your knees for him, moaning softly into the pillow below you. you felt the pleasure rise in your stomach again, and it didn’t take long for you to be a shaking mess on his fingers.

finally, you came, legs trembling and moans shaking into the pillow. slowly, he pulled his fingers out, wiped them with a tissue, and laid next to your sore form. he wrapped an arm around you.

“doing alright?” wilbur asked, his eyes half lidded with sleep, but clearly still wanting to stay up and talk to you. “yeah… but, uh… what does this make us?” you questioned. wilbur’s eyes softened, his eyes seeming almost guilty. “well… right now isn’t really the time for this discussion, no?” he said. you frowned at him, but he was right… it was three in the morning and the both of you were struggling to stay awake. “i suppose not…”