Day 6 (1/2 way through)

Cheri wakes you up with a mischievous glint in her eye, her hand already fondling your balls as she holds the advent jar in her other hand. 'Draw, please,' she purrs, her voice low and sultry. You oblige, reaching into the jar and pulling out a folded slip of paper.

You read the dare aloud: 'Attend a strip club together and take turns watching the strippers dance on each of you.' Cheri's eyes light up with excitement. 'Looks like a trip to the boom boom room tonight,' she grins.

But first, you have other plans. You pull Cheri close, your hands roaming over her curves as you kiss her deeply. She responds with equal passion, her hands tangling in your hair as she straddles your hips.

You make love with fierce intensity, your bodies moving together in perfect sync. Cheri's moans fill the room as you bring her to orgasm again and again, her juices soaking the sheets beneath you. Finally, you flip her over and take her from behind, your hips slamming against her ass until you explode inside her with a guttural groan.

Afterwards, you collapse onto the bed together, your chests heaving. 'So,' Cheri says after a moment, her voice still breathless. 'Which club should we meet at?'

You discuss the options, finally settling on a place downtown. 'I can't wait,' Cheri murmurs, her eyes sparkling with anticipation. 'This is going to be so much fun.' You grin, your own excitement building. It's going to be a night to remember.

You and Cheri step into the shower together, the hot water cascading over your bodies as you wrap your arms around each other. Cheri giggles as you spin her around, your hands roaming over her slick skin as you trail kisses down her neck.

'You're insatiable,' she murmurs, her fingers tangling in your hair as you kneel in front of her. 'I love it.'

You look up at her, a mischievous glint in your eye. 'You haven't seen anything yet,' you purr, your hands sliding up her thighs.

Cheri gasps as your tongue finds her core, her fingers tightening in your hair. You take your time, savoring her taste as you bring her to the brink again and again. Her moans echo off the tiles, her legs trembling with each climax.

Finally, you stand, your hands gripping her hips as you pull her close. Cheri wraps her legs around your waist, her arms around your neck as you slide into her with a groan. You move together, your bodies in perfect sync as the water sluices over your skin.

Cheri comes with a cry, her nails digging into your back as she pulses around you. You follow moments later, your own release triggering another orgasm for her. You hold each other tight, your chests heaving as you come down from the high.

Afterwards, you dry each other off, your hands lingering on damp skin. Cheri grins up at you, her eyes sparkling with mischief. 'I can't wait to see what you have planned for me today,' she murmurs, her lips brushing yours. 'I'll be thinking about you all day.'

You grin back, your own anticipation building. 'Me too,' you reply, your voice low. 'I'll be counting the minutes until I see you again.'

You settle in at your desk, your mind still buzzing with the memories of your morning tryst with Cheri. As you boot up your computer, your phone buzzes with an incoming text.

It's from Cheri, a single emoji: . You grin, your fingers flying over the keys as you type out a response. 'Wish you were here to give me a taste. '

Her reply is almost instantaneous. 'Mmm, I'd love to. But then you'd never get any work done, would you? '

You chuckle, shaking your head. 'True. But I'd rather be doing you than this boring report.'

'Patience, baby,' Cheri responds. 'We'll have plenty of time to play later. For now, behave yourself and get some work done. '

You sigh, your eyes straying to the clock on your computer screen. It's going to be a long day. But the promise of what's to come keeps a smile on your face as you dive into your work, your phone buzzing periodically with flirty texts from Cheri.

As the day wears on, the texts grow hotter, more explicit. Cheri describes in detail what she plans to do to you later, her words painting vivid pictures in your mind. You find yourself shifting in your seat, your arousal growing with each message.

By the time 3:00 rolls around, you're hard and aching, your mind consumed by thoughts of Cheri and the night ahead. You hurry out of the office, your phone clutched in your hand as you make your way home, eager to put your plans into action.

You arrive home, your heart racing with anticipation for the night ahead. You quickly shower and change into a sharp button-down and slacks, adding a spritz of cologne for good measure.

As you're putting the finishing touches on your outfit, your phone buzzes with a text from Cheri. 'Wear something nice,' it reads. 'I have a surprise for you. '

Intrigued, you make your way to the living room, your curiosity piqued. When Cheri emerges from the bedroom, your jaw drops. She's wearing a slutty Mrs. Claus dress that barely covers her ass, the candy cane stockings hugging her long legs. Her hair is tousled and her lips are painted a deep, sultry red.

'Well?' she purrs, doing a little twirl. 'What do you think?'

You can't help but stare, your eyes roaming over her body. 'You look... incredible,' you manage to say, your voice hoarse with desire. 'Absolutely incredible.'

Cheri grins, her eyes sparkling with mischief. 'I thought you might like it,' she says, sauntering towards you. 'I've been saving it for a special occasion.'

She stops in front of you, her hands trailing over your chest. 'And what occasion is that?' you ask, your skin tingling under her touch.

'Our first trip to a strip club, of course,' she replies, her lips brushing yours. 'I want to make sure all eyes are on me tonight. Especially yours.'

You give Cheri a playful spank, your hand connecting with her barely-covered ass with a satisfying smack. 'Alright, minx,' you growl, your voice low and husky. 'It's time to go. I can't wait to see you in action at the club.'

Cheri yelps, then giggles, her eyes dark with desire. 'Mmm, I can't wait either,' she purrs, pressing her body against yours. 'I'm going to give you a show you'll never forget.'

You flag down a cab, your hand resting possessively on Cheri's thigh as you make your way to the strip club. The anticipation is thick in the air, the sexual tension between you simmering just below the surface.

When you arrive, the club is dark and pulsing with music, the air heavy with the scent of perfume and sweat. You find a table near the stage, your eyes roaming over the dancers as they gyrate and twirl.

Cheri leans in close, her lips brushing your ear. 'I'm going to need some singles,' she whispers, her breath hot against your skin. 'For the dancers.'

You raise an eyebrow, a smirk tugging at your lips. 'Is that so?' you ask, your voice teasing. 'And how, exactly, do you plan on delivering them?'

In response, Cheri opens her mouth, her tongue darting out to lick her lips. You can't help but chuckle, shaking your head as you pull out a wad of singles. 'You're incorrigible,' you say, stuffing the bills into her mouth.

Cheri grins, her eyes sparkling with mischief. She saunters over to the stage, her hips swaying seductively. She approaches one of the dancers, a busty brunette in a skimpy bikini, and tucks a bill into her cleavage. The dancer smiles, her eyes flicking to you as she gives Cheri a wink.

Cheri moves on to the next dancer, a lithe blonde in a thong and pasties. She bends over, giving you a perfect view of her ass as she tucks a bill into the dancer's G-string. The blonde gasps, her eyes widening as Cheri straightens up, a wicked grin on her face.

You watch, your arousal growing with each passing moment, as Cheri makes her way around the room, delivering singles to the dancers in increasingly creative ways. By the time she returns to your table, you're hard and aching, your need for her consuming you.

'So,' Cheri purrs, sliding into your lap. 'Which one should we take to the boom boom room?'

You start to ask her if she has a preference when Feliz Navidad starts playing. As the opening notes of Feliz Navidad fill the room, a stunning Latina dancer takes the stage. Her voluptuous curves are barely contained by a tiny red bikini top and matching thong, drawing the eye of every patron. She moves with fluid grace, her hips swaying seductively to the beat.

You glance over at Cheri, raising an eyebrow in question. 'Her,' you say simply, nodding towards the dancer. 'That's who I want for the private dance.'

Cheri follows your gaze, her eyes widening as she takes in the dancer's sensual moves. 'Mmm, yes,' she purrs, her hand trailing up your thigh. 'She's perfect. Absolutely perfect.'

You flag down a waitress, indicating your choice. She nods, disappearing into the back to fetch the dancer. A few moments later, the Latina beauty appears at your table, her smile sultry and inviting.

'Hey there, handsome,' she purrs, her voice low and husky. 'I hear you requested a private dance. I'm Isabella, and I'd be more than happy to oblige.'

You grin, your eyes roaming over her body. 'Isabella,' you repeat, the name rolling off your tongue. 'I have a feeling you're about to make all my Christmas wishes come true.'

Isabella chuckles, her hand brushing your shoulder. 'Oh, I plan on doing more than that,' she whispers, her lips brushing your ear. 'I'm going to give you a dance you'll never forget.'

She takes your hand, leading you towards the private rooms at the back of the club. Cheri follows close behind, her eyes sparkling with anticipation. As you step into the dimly lit room, Isabella pushes you down onto the plush couch, her body moving to the music.

'Watch closely, baby,' Cheri purrs, sliding in beside you. 'I have a feeling we're in for a treat.'

Isabella begins to dance, her movements slow and sensual. She runs her hands over her curves, teasing the edges of her bikini top. Her hips undulate, swaying to the music as she inches closer to where you sit.

You watch, transfixed, as she reaches behind her back, untying her top. It falls to the floor, revealing her full, round breasts. She cups them, squeezing gently as she rolls her nipples between her fingers.

Beside you, Cheri shifts, her breath quickening. You glance over, seeing her eyes dark with desire. 'Fuck,' she breathes, her hand sliding up your thigh. 'She's so fucking hot.'

You nod, your eyes never leaving Isabella. She's close enough to touch now, her body mere inches from yours. She drops to her knees, her hands trailing up your legs. She leans in, her lips brushing your ear.

'You like what you see, papi?' she whispers, her voice low and seductive. 'You want to touch?'

You groan, your hands clenching into fists at your sides. 'Yes,' you grit out, your voice strained. 'God, yes.'

Isabella chuckles, the sound low and throaty. 'Then do it,' she purrs, taking your hands and placing them on her breasts. 'Touch me, papi. Make me feel good.'

You hesitate for only a moment before giving in, your hands kneading her soft flesh. She moans, arching into your touch as her hands slide up your chest.

'Fuck, that's it,' Cheri breathes beside you, her hand rubbing your cock through your pants. 'Touch her, baby. Show her how good you can make her feel.'

You continue to explore Isabella's body, your hands roaming over her curves. She grinds against you, her hips undulating in time with the music. The room is filled with the sounds of moans and heavy breathing, the air thick with the scent of arousal.

As the song comes to an end, Isabella pulls back, her skin flushed and glistening with sweat. 'Mmm, that was fun,' she purrs, her fingers trailing down your chest. 'You sure know how to make a girl feel good, papi.'

She stands, retrieving her bikini top from the floor. She ties it back on, blowing you a kiss before sauntering out of the room.

Cheri turns to you, her eyes dark with desire. 'Holy shit, that was so fucking hot,' she breathes, her hand palming your erection through your pants. 'I need you, baby. I need you right fucking now.'

You and Cheri stumble through the front door, your hands roaming each other's bodies as you make your way to the bedroom. The sexual tension between you is palpable, the air crackling with electricity. You can't wait to get her alone, to explore every inch of her body and make her squirm with pleasure.

As soon as you cross the threshold, you pull her into your arms, your lips crashing against hers in a searing kiss. She moans into your mouth, her fingers tangling in your hair as she pulls you closer. You walk her backwards until her legs hit the bed, then lower her down onto the mattress.

'Fuck me, baby,' Cheri breathes, her voice husky with desire. 'I need to feel you inside me.'

You don't need to be told twice. You quickly shed your clothes, your eyes never leaving hers as you climb onto the bed. You settle between her thighs, your cock nudging against her entrance. With a groan, you thrust forward, burying yourself to the hilt in her wet heat.

Cheri cries out, her nails digging into your back as she arches beneath you. 'Yes,' she moans, her hips rocking to meet your thrusts. 'Just like that. Fuck me hard, baby. Make me squirt all over your cock.'

You oblige, your hips snapping as you pound into her. The room is filled with the sounds of flesh slapping against flesh, of moans and cries of pleasure. Cheri's pussy clamps down on your cock, her walls fluttering as she nears her peak.

'Come for me, baby,' you growl, your fingers finding her clit. 'Come all over my cock like a good girl.'

With a keening cry, Cheri shatters, her pussy clenching around you as she squirts. You don't let up, fucking her through her orgasm until she's a quivering, whimpering mess beneath you. Only then do you allow yourself to let go, your own climax crashing over you as you coat her face with your seed.

You lean in close to Cheri, your breath still heavy from your recent tryst. 'Hey babe,' you murmur, your voice low and husky. 'There's something I've been wanting to try with you. A new position I think we'd both enjoy.'

Cheri's eyes light up, a wicked grin spreading across her face. 'Oh yeah?' she purrs, her hand trailing up your chest. 'And what position would that be?'

You grin back, your hand sliding down to cup her ass. 'It's called the butterfly,' you say, your fingers squeezing gently. 'You lie on your back with your legs up and spread, while I kneel between them. It's supposed to be great for deep penetration and hitting your G-spot.'

Cheri moans softly, her hips rocking against yours. 'Mmm, that sounds delicious,' she breathes, her fingers tangling in your hair. 'I'm always down to try new things with you, baby. Especially when they involve you fucking me deep and hard.'

You chuckle, your lips brushing hers. 'That's my girl,' you murmur, your tongue darting out to taste her lips. 'Always up for anything.'

Cheri grins against your mouth, her teeth nipping at your lower lip. 'You know me,' she purrs, her voice thick with desire. 'I'm insatiable when it comes to you. Now, are you going to show me this butterfly position, or what?'

You don't need to be told twice. You pull back, your hands going to Cheri's hips as you guide her onto her back. She follows your lead eagerly, her legs spreading wide as she lies down on the bed. You kneel between her thighs, your cock twitching as you take in the sight of her, open and ready for you.

'Fuck,' you breathe, your eyes roaming over her body. 'You look so fucking sexy like this, baby. All spread out and waiting for me to fuck you.'

Cheri moans, her back arching as she pushes her hips towards you. 'Then what are you waiting for?' she asks, her voice breathy with need. 'Fuck me, baby. Show me what this butterfly position can do.'

You grin, your hands going to her hips as you pull her closer. You line your cock up with her entrance, teasing her with just the tip. 'With pleasure,' you growl, your voice low and rough. 'Hold on tight, baby. This is going to be a wild ride.'

With that, you thrust forward, burying yourself to the hilt in her wet heat. Cheri cries out, her legs wrapping around your waist as she pulls you deeper. You oblige, your hips snapping as you fuck her hard and fast.

The room is filled with the sounds of flesh slapping against flesh, of moans and cries of pleasure. Cheri's pussy clamps down on your cock, her walls fluttering as she nears her peak. 'Yes,' she moans, her head thrown back in ecstasy. 'Fuck, yes. Just like that. Don't stop, baby. Don't ever stop.'

You don't, your hips pistoning as you drive into her again and again. Cheri's moans grow louder, her nails digging into your back as she urges you on. 'Fuck,' she gasps, her pussy clenching around you. 'I'm gonna come, baby. I'm gonna come so hard on your cock.'

You groan, your own climax building as you feel her walls begin to flutter. 'Come for me, baby,' you grit out, your voice strained. 'Come all over my cock like a good girl.'

With a keening cry, Cheri shatters, her pussy clamping down on you like a vice as she comes hard. The feeling of her walls pulsing around you is enough to send you over the edge, your own climax crashing over you as you coat her belly with your seed.

You collapse onto the bed beside her, your chest heaving as you struggle to catch your breath. Cheri turns to you, her face flushed and glistening with your come. 'Holy shit,' she breathes, her voice hoarse from screaming. 'That was... fuck. That was incredible.'

You grin, your hand reaching out to brush a strand of hair from her face. 'Told you it would be good,' you murmur, your thumb stroking her cheek. 'But trust me, baby. We're just getting started.'

You pull Cheri close, wrapping your arms around her as you settle into the plush comfort of your bed. She sighs contentedly, nestling her head against your chest as her fingers trace lazy patterns on your skin.

'You know,' she murmurs after a moment, her voice soft and thoughtful. 'As much as I love our little adventures, sometimes it's the quiet moments like these that mean the most to me.'

You hum in agreement, your hand stroking her hair. 'I feel the same way, baby,' you say, your voice low and warm. 'There's nothing quite like holding you in my arms, just being together.'

Cheri tilts her head up, her eyes meeting yours with a smile. 'I have an idea,' she says, her voice taking on a mischievous tone. 'Why don't we try a new position? Something we haven't done before?'

You raise an eyebrow, intrigued. 'Oh yeah?' you ask, your interest piqued. 'What did you have in mind?'

Cheri's eyes light up with excitement as she suggests a new position for you to try together. 'I want you to piledrive me,' she purrs, her voice low and seductive. 'My ass high in the air while you squat and thrust deep into my pussy. I want to gush like a geyser when I come, and then I want you to blow your load all over my asshole.'

You grin, your cock twitching at the mental image. 'Fuck, baby,' you growl, your voice rough with desire. 'You have the best ideas. I can't wait to make you squirt and then cover your ass with my cum.'

Cheri giggles, her eyes sparkling with mischief. 'Then what are you waiting for, baby? Let's get to it.'

You waste no time, flipping Cheri over onto her hands and knees. She arches her back, presenting her ass to you like an offering. You position yourself behind her, squatting down so that your cock is level with her dripping pussy.

With a groan, you thrust forward, burying yourself to the hilt in her tight heat. Cheri cries out, her walls clamping down on you like a vice. You set a punishing pace, your hips snapping as you fuck her hard and deep.

The room is filled with the sounds of flesh slapping against flesh, of moans and cries of pleasure. Cheri's pussy clamps down on your cock, her walls fluttering as she nears her peak. 'Yes,' she moans, her head thrown back in ecstasy. 'Fuck, yes. Just like that. Don't stop, baby. Don't ever stop.'

You don't, your hips pistoning as you drive into her again and again. Cheri's moans grow louder, her nails digging into the sheets as she urges you on. 'Fuck,' she gasps, her pussy clenching around you. 'I'm gonna come, baby. I'm gonna come so hard on your cock.'

With a keening cry, Cheri shatters, her pussy clamping down on you like a vice as she comes hard. Her juices gush out, soaking your cock and balls as she squirts. The feeling of her walls pulsing around you is enough to send you over the edge, your own climax crashing over you as you pull out and coat her asshole with your seed.

You collapse onto the bed beside her, your chest heaving as you struggle to catch your breath. Cheri turns to you, her face flushed and glistening with sweat. 'Holy shit,' she breathes, her voice hoarse from screaming. 'That was... fuck. That was incredible.'

You suggest to Cheri that you both shower together and then go to bed. She agrees eagerly, a playful glint in her eye as she takes your hand and leads you to the bathroom.

Under the hot spray of the shower, you take your time washing each other, hands roaming over slick, soapy skin. Cheri's fingers trail along your chest and abs before wrapping around your semi-hard cock, stroking you back to full hardness. You return the favor, caressing her full breasts and teasing her already stiff nipples. Your hands slide lower, over the curve of her hips to grip her luscious ass. She moans softly as your fingers dip between her cheeks to tease her tight hole.

The steam and the heat of your arousal fog up the glass shower door. Cheri turns around, bracing her hands on the tiled wall and arching her back, presenting herself to you. 'Take me, baby,' she purrs, glancing over her shoulder at you with a sultry look. 'Fuck me hard, right here against the wall.'

You don't need to be told twice. Gripping her hips, you line yourself up and thrust deep into her dripping heat in one smooth stroke. She's so wet, so tight, her walls clenching around you like a vice. You set a punishing pace, skin slapping against skin, the lewd sounds echoing off the tiles. Cheri meets you thrust for thrust, pushing back against you and crying out for more.

It doesn't take long before you feel your climax building, a tingling warmth at the base of your spine. Reaching around, you rub tight circles over Cheri's clit in time with your thrusts. 'Come with me, baby,' you growl in her ear. 'I want to feel you come all over my cock.'

Your words send her flying over the edge with a keening cry, her pussy clamping down on you as she comes hard. The fluttering pulses of her walls milk your own orgasm from you and with a harsh groan, you bury yourself deep and spill inside her, painting her walls white with your seed.

You stay like that for a long moment, chests heaving, as the aftershocks of your shared climax fade away. Gently, you withdraw and help Cheri to straighten up, both of you rinsing off one last time before stepping out of the shower.

After toweling off, you collapse into bed together, Cheri curling up against your side with a contented sigh. Her head rests on your chest, fingers idly tracing patterns on your skin. Within minutes, her breathing evens out and she falls into a sated, peaceful sleep. Smiling, you press a soft kiss to her hair before allowing yourself to drift off as well, secure in the knowledge that tomorrow's advent calendar dare is sure to bring even more excitement and pleasure.