Trip to Strip

Dan groggily opened his eyes, his mind still foggy from sleep. It was a new day at the Harem Hotel. Fortunately, this time there were no reality-warping events planned for the day. That didn’t mean, however, that the season’s Master would be free of challenges himself. As his vision cleared, he felt a weight on his chest. ‘Tori? Wait, no…’

His heart skipped a beat. There, latched onto him like a barnacle, was Chloe, the brash tomboy who, up until last night, was the target of much ire from his childhood. Donned in nothing more than a pair of simple panties and his shirt, the Amazonian brunette softly snored into his chest, an arm possessively draped over him. At Chloe’s **** insistence, the two had fallen asleep on opposite sides of the large King-sized bed, but there was a small detail that Dan would never have known about his companion in normal circumstances: That she was a big spoon.

Taking a deep breath, Dan slowly shifted his body, inching towards the edge of the bed. His muscles tensed, his heart raced, and he prayed for a swift and silent escape. With each careful movement, he could feel the pressure on his chest gradually easing. It seemed luck was on his side, and Chloe remained blissfully unaware.

With a final push, Dan managed to free himself from Chloe's grasp. He quickly tiptoed towards the bedroom door, trying his best to stifle any noise that could potentially wake her. Once out the door, he sighed with relief, his body tingling with a mix of anxiety and triumph.

“Good morning.” Dan leaped out of his skin before turning toward the sight of his one and only secretary sitting by his suite's coffee table, sipping on a delicious-smelling brew. Dressed as immaculately as ever, she sighed as her emerald eyes roamed from the visage of her boss to the erection attempting to burst from his boxers. “At least try not to make a habit of exposing yourself to me.”

“I, uh… My bad.” Dan sheepishly tried and failed to hide his impressive morning wood from Natalia once again. “Wait, why am I apologizing? You’re the one in my suite!”

Natalia put down her coffee and gestured toward the second mug sitting by a recliner before sarcastically responding. “For some reason, I keep waking up with this nagging compulsion to bring you coffee. I can’t imagine why.”

Dan huffed as he returned to his bedroom to stealthily snatch his hanging bathrobe from its spot, ignoring the now spread-eagled form of Chloe taking up 90% of the bed. Now somewhat covered up, Dan joined his Irish companion in enjoying their morning cup. “Thanks for the coffee. Though it’s not like making coffee is the only thing secretaries do, you know?”

Natalia fought off the tingle of pleasure she got from those words of gratitude and frowned as she shifted in her seat. “Tell that to the twisted fucks who made me like this.”

Dan watched on and noticed her unease. “Are you okay? You’re a bit…”

“Agitated? Antsy?” She barked back before breathing out slowly. “I take it the two of you didn’t have sex last night.”

Dan almost spat out his drink. “The fuck!?”

“Hmph. Figured as much…” She sighed as she took a sip of her coffee. ‘Thank God tonight’s Tori’s turn.’

“Is it really that bad?” Dan asked, curious about what exactly his subordinate was experiencing due to his recent drought in his sex life.

Natalia hesitated while the tips of her ears began to match the color of her hair. ‘Like hell, I’d tell him it’s like being constantly edged and that it’s getting worse by the day. I’d rather die.’

“... Could be worse.” She finally answered. Her eyes met with his for just a brief moment before she diverted them back toward her coffee. “Just… annoying is all. I’d very much prefer that you don’t ask.”

“Got it, message received.” Dan nodded in understanding.

A few moments of silence passed while the two sipped on their coffee. Neither was eager to start back up the awkward conversation, at least until a beep from Natalia’s phone broke up the silence. She begrudgingly put down her cup and checked the incoming message, only for a frown to mar her face as she read the message sent to her.

“What is it?” Dan inquired, leaning forward but only getting a small glimpse of the wall of text sprinkled with emojis before a growl formed in Natalia's throat.

“Just a reminder that Vanessa has a sense of humor, I suppose.” She threw her phone back into her purse and began gulping the rest of her coffee. She slammed her empty mug on the coffee table and glared at her boss. “I am to remind you that today is Sam’s first day on the job and that she should be at the club at around 4 pm to begin her training. Why I am telling you this, other than the fact that Vanessa has graciously deemed it necessary for my own “development,” is because the owner has requested your presence at said club.”

Dan furrowed his brow. “Shit, I forgot about that… I can’t believe Vanessa is making her a damn stripper.”

“Horrendous,” Nat commented dryly before continuing. “Lastly, tonight is Tori’s night to be your “companion.” Though she isn’t required to take you on a date like Chloe did last night, she must spend the night in your bed.”

“Oh.” Dan’s face lit up at the mention of his “first” girlfriend. ‘At least some good news then…’

“And with that, my job here is done. Now, if you’ll excuse me…” Natalia began quickly gathering her things and made for the suite’s private elevator, her heels clacking in quick succession.

“Ah, right.” Dan followed his assistant to the doors like a courteous host. “Thanks for the coffee again and… I guess for the itinerary, too.”

The secretary could not stop herself from letting out an unusually sensual voice as her boss's gratitude warped into something far more carnal for her reddening ears. “It’s my pleasure…”

Dan’s mind whiplashed as he took in the half-moaned words of his secretary. “Wow. That’s… uh, something.”

“Oh, Fakin’ hell.” Nat’s face matched her hair color as she fled into the opening elevator and mashed the close door button. “Shove off already! Go play with the fakin’ bird in yer bed. Fucks sake.”

The elevator finally did its part and withdrew the flustered woman from her boss's presence while Dan simply watched in amusement. ‘I guess her accent really only comes out when she’s flustered…’

Now all alone, the man figured he might as well bite the bullet and address the sleeping tomboy in his bed. Something he’d soon regret as he learned a second fact about his former high school bully. She was not a morning person.

**********

“Do we have to?” Dan whined as he came to a stop along the sidewalk.

“Yep! Boss lady said so. She even came by earlier to wish me luck!” Sam smiled as she turned around to look at her anxious brother. Her smile turned a bit wry as she added. “Plus, I… uh… kinda want y’all here for support. So… Thanks.”

Tori stormed forward and embraced her beloved pseudo-siblings. “Of course we’d be there to support you! Right, Danny?”

Dan sighed as he scratched the back of his head. “Yeah, sure. It’s just…”

Tori’s eyes narrowed as she glared at him to get him to put a foot in his mouth.

“I mean… I know you’ll be fine!” Dan nervously backpedaled. “Whitakers always try their best, right?”

“That’s right!” Sam's smile returned as she shook off Tori and latched onto her brother for a hug. “Thanks, Bro! Love you!”

“Y-yeah… Love you too.” Reluctantly, Dan relented while mentally screaming. ‘Why the hell am I more anxious about this than her!?’

The three stood there hugging momentarily before continuing their short trek toward Sam’s new place of work. As Natalia described to Dan earlier in the day, he was to escort his lovely sister to the strip club around 4 pm, something he dreaded every step of the way. His only solace was when Tori demanded that she accompany them when they met up earlier for lunch. Maddy had tried to invite herself along, but Sam asked if it could just be the three of them, if possible. Unable to argue, Maddy relented and bothered Yui with her antics instead. Thus, when it was finally time, the Whitaker siblings, plus one Chapman, ventured out from the hotel and down the street toward their destination.

“Woah, is that it? This place is huge!” Sam suddenly shouted as the visage of the Brooks Gentleman Club came into view. Unlike most strip clubs Dan had seen or been to, this one made zero attempts to be inconspicuous. The large white building was highlighted with bright tropical colors and accented with some of the most interesting mosaic tilework Dan had ever seen on a classic Art Deco-styled building. And if the exterior didn’t draw the eye, the massive neon sign of a well-endowed woman with a river flowing between her breasts would.

“I feel like the sign doesn’t match the building,” Tori judged, memories of a past life visiting these types of places with Dan as a reference. Not that she’d want him to visit them normally now. Perhaps not without her, at least.

Dan chortled. “No kidding, the building is way too pretty to be a strip club.”

“Really? Why’s that?” Sam questioned with a tilt of her head. “Wouldn’t a pretty building get more customers?”

“I think clubgoers care far more about what’s on inside than what the place looks like,” Dan remarked. Though now he wondered. “Sam, have you… Ever actually been to a strip club before?”

She shook her head. “Nope! Always wanted to, though! Topless chicks are rad!”

‘Sam, you’re about to be the topless chick…’ Dan sighed. He took a moment to spare a glance at his girlfriend, who smiled wryly in response. “Alright, get in there, tiger.”

“Woohoo!” Sam cheered and led the charge into the venue. As the trio entered, instead of further appreciating the gorgeous decor, they were immediately approached by a couple of burly men who looked like they could put male Chloe to shame with how muscular they were.

“The club’s not open yet. 6 PM on weekdays.” The bald yet bearded bouncer said while pointing out the hours displayed on a poster they had passed. “Come back in a couple of hours.”

“Woah!” Sam’s eyes went starry as she pointed at the two burly men. “You’re huge!”

“What she means to say… Is that we have an appointment?” Dan reached forward, placing a hand on Sam’s shoulder, stopping her from possibly insulting the two giants before them. “My sister here is supposed to be starting here today, and we’re to meet the owner.”

The second short-haired giant snorted in acknowledgment and reached for a radio. “Ma’am, were you expecting a new girl today? She’s with a guy and another girl. I see.” The giant lowered his radio and gestured toward the trio. “Looks like Ms. Brook is expecting you. Follow me to the back.”

Without another word, the stern man began walking deeper into the venue. Dan quickly pulled along his sister and fell in line behind him, not wanting to risk garnering any possible ire. As the group navigated through the venue, Dan couldn’t help but notice the large central room that held an impressive stage with multiple poles and fixtures. Several girls appeared to be practicing their moves as they casually swung around to the beat of some quiet music. The longer he looked at them, the harder it began to sink in that his brother-turned-sister would soon be one of them.

Before he could get more absorbed into his thoughts, Dan felt a hand slip into his own and intertwine their fingers with his. He looked back to see Tori smiling at him in solidarity. She whispered in his ear. “She’ll be fine. She’s a big girl; she can take care of herself.”

At first, Tori furrowed her brow when she caught her man staring at the attractive dancers, but when she got a good look at his expression, the conflict and storm of emotions he showed, she eased back.

“I…” Dan started before realizing that maybe she was right. “You’re right. I just… This is wild.”

“I know. But that’s why you need to support her.” Tori spoke gently, rubbing her thumb along the back of his. “Help her get through this. It’s not like this is permanent, right?”

Dan nodded. “I’ll make sure of it. Thanks, Tori.”

“Anytime, Danny.” She pecked him on the cheek before pulling him along. “Come on, we’re making a scene.”

Dan looked around and saw Sam and the gruff bouncer staring at the couple. Embarrassed, he quickly caught up with the rest of the group and continued toward the back offices.

Soon enough, the group found themselves in front of a rather impressive office, where the bouncer leading them knocked gently on the closed door. “Ma’am, your appointment is here.”

“Kay! Send them in, por favor!” A feminine voice shouted from the other side.

The bouncer grunted and opened the door, allowing the trio to get a first look at the esteemed owner. Dan didn’t know what he expected, but what he saw was not it.

“Hey! Hey! Whazzup!” A young tanned woman with unnaturally green hair approached them, holding up a couple of peace signs with her expertly manicured hands. Wearing a pink bikini top, black leather hotpants, and matching pink thigh-high boots, the only thing “professional” she wore was a black suit jacket hanging off her shoulders like a shawl. “Aren’t you three like the absolute cutest! Childhood lovers and a golden retriever puppy of a little sister. OMG, I LOVE you guys sooooo much!”

“Uh, thanks?” Dan replied, bewildered, as the young woman darted over and took turns hugging each of them. Even the bouncer got a hug.

“No probs! Oh my gosh, where are my manners?! I’m Brook, the owner of this lovely establishment. It’s like totally awesome to meet y’all.”

“Pleasure’s totally ours…” Sam commented with a silly grin plastered on her blushing face.

“Hehehe…” Brook giggled as she sat on top of her desk. She gestured toward the seats in front of her. “Please take a seat! Oh, and we’re good, Spike, no need for the escort.”

The giant nodded and took his leave without another word. Brook hummed to herself. “Ain’t he just a big softy. Found him after his Master abandoned him. Poor thing. Oh! Speaking of which… I’ve been watching y’all’s season so far. You’ve got yourself quite a harem, cutie! The sexual tension between you and Chloe last night was hot af!”

“The what?” Tori raised an eyebrow as she turned toward her boyfriend.

“Hold up!” Dan raised his hands as if to defend himself. “Nothing happened! Literally, nothing is going on between us. I mean, that’s Chloe for God's sake.”

“Who’s a smokin’ hot tomboy babe!” Brook exclaimed as she jumped dramatically from her seat. “Past is the past, you two totally have to smash at some point! Oh, and that sexy secretary of yours, oof, I want her to sit on my face! Golly, so many hot chicks, not to mention the goddesses with you now. Love the whole childhood romance angle you got going on. So romantic! You better jump him tonight, girl!”

While Brook gave Tori an exaggerated wink, the latter blushed as the thought crossed her mind. ‘God, I hope.’

“Anywho! Enough teasing, we got a new employee, now don’t we?” The club owner/manager found her way back to her desk seat and pulled out her phone. “Vanessa already shared all the deets, so I’ll address your biggest concern, Darlin’. As long as our cute Puppy works here, no one, and I mean no one, will be allowed to touch your beloved sister sexually. Without your permission, that is! Some folks are totally into that stuff, but I can tell you ain’t one of them.”

“I guess that’s a good thing…” Dan spoke, conflicted.

“For you, it is! You’ll have your own little sexy private dancer!” Brook giggled. “After I personally train her, though, of course. Which leads me to this question: Cutie, may I have permission to touch your sister for the sake of training?”

“Yes!” Sam shouted before Dan could respond. “I mean, I’m totally cool with it. So no probs, right, Bro?”

The way Sam stared so intently into Dan’s eyes made him chuckle. “You heard her, I’m good with that.”

“Awesome!” Brook cheered as she rounded back toward Sam and crashed into her for a big hug. “By the time I’m done with you, Cutie won’t be able to keep his eyes or hands off these sexy hips.”

Brook then discussed other housekeeping items, such as Sam’s hours and wages. Surprisingly, the part-time benchmark was similar to standard practices, with Sam required only to work 25 hours each week. A week being the same length as a Harem Hotel Round, so 8 days in this case. So if she chose to work 5 hours a night, she’d still get three days off a week, one of which would always be for the competition and another for her night with Dan. She could always work more hours if she wanted, but knowing Sam, Dan was sure she’d want to do the bare minimum.

As far as wages go, however, Sam would earn about 50BP an hour, not including tips. Without a frame of reference, Dan was unsure whether this was a fair deal, but Brook seemed adamant that she would never rip off her employees. Something she claimed to be incredibly passionate about.

“My employees are like family to me, and as long as you work here, Big Sis Brook will take good care of you.” Brook smiled sweetly as she kissed Sam’s forehead from her place in the latter’s lap. The green-haired girl jumped from her newest employee’s lap and walked over to her desk again. “Well, I think that just about covers everything! Let’s get your onboarding out of the way, then we can start your orientation!”

“Would you like us to stay for her orientation?” Tori asked in Dan’s stead.

Brook tilted her head to think. “Hmmm… Nope! We got this from here, right, Sam?”

“Totally!” Sam agreed with a dopey smile on her face. ‘Alone time with her? Yes, please!’

Dan reached out and grabbed his sister's hand. “Just remember, we’re here for you. If you need us to come back at any point, just call. We’ll be there, I promise.”

Sam leaned over and hugged her brother. “Gosh, you’re such a worrywart. You said it yourself, right? A Whitaker always tries their best! I’ll be 100% fine.”

“I know.” Dan breathed out. “You’ll be fine. I love you… Sis.”

Sam smiled brightly. “I love you too, Bro!”

The two were broken from their moment by a squeal on the other side of the room. “OMG! I think I need to go check my blood sugar levels. Think I’m overloaded with how sweet you two are. Uhhhhg. I’m so jelly!”

“They are pretty cute, huh?” Tori murmured to herself.

The siblings released each other and sheepishly returned to discussing Sam’s employment. Once all the paperwork was signed, Brook escorted the group back toward the club's entrance, where Dan and Tori took their leave.

“Oh! By the way!” Brook called out before the couple could exit the venue. “As this season's current master, you get unlimited access and drinks here. Feel free to come around as a guest whenever you'd like. And bring your other cuties too!” She paused for a second before adding. “But not for a couple of days. I need to train up your private dancer first!”

“Okay, sure. I’ll keep that in mind.” Dan laughed at the thought of bringing Gabriella, of all people, to a strip club. ‘The girl would have a heart attack.’

“Oh! And don’t worry about picking Sam up after her shift. I’ll have Spike here escort her home safely.” Brook gestured toward the man who escorted them earlier. The giant grunted in affirmation as his gaze bore down on Dan.

“Thank you, Brook,” Tori said graciously.

“Now, you two run along and enjoy your date night.” Brook began shooing the couple away. “I’m expecting sexy things from you two!”

Before Dan could respond, Tori interlaced her fingers with his and kissed his cheek. Her sensual voice whispered in his ear. “I am too.”

Dan stammered as he looked into her smoldering gaze, an unsaid promise of what would come. He gripped her hand tightly as he began to pull her away. “Look forward to it then.”

As the flirting couple took their leave, Brook giggled from her place next to her newest employee. “Your brother is something else, you know that?”

“Yep! He’s the best!” The brunette responded without a shred of doubt in her words.

**********

AN: Well Howdy, sorry about the break between these last couple of chapters. Between the new Legend of Zelda coming out and me getting Covid for the first time, I had alot on my plate. I hope you guys enjoy this latest chapter! Next time will be a certain event I'm sure most of you have been waiting for. See y'all next time!