Tricked into Turning a Trick Pt. 08

Part 8 - The Business Trip

The following week Amanda went to work like normal. She hadn't spoken with Jenn since the night at the Roadway Inn. She wanted to reach out but didn't know what to say. She also wanted Jenn some time to reflect on it on her own.

Amanda started to get worried after a week had passed without any word from Jenn. However, her concern for her friend quickly shifted to excitement for herself when Rick summoned her into his office with unexpected news. She would be accompanying him on a business trip. He needed her in New York for a few days and they were leaving tomorrow. Jenn would have to wait.

As Amanda packed that night, she struggled to decide what to bring. She had never been on a business trip before. In fact, she had never traveled anywhere outside of her home state. The thought of visiting New York City for the first time filled her with excitement.

Amanda's excitement grew even more when she saw Rick pull up in a limousine the next morning. But it reached pure bliss when they arrived at the airport, bypassing the commercial terminals and heading straight to the commuter terminal, where a private jet was waiting for them on the tarmac.

The pilot stood in front of the jet as Rick made his way across the tarmac toward the plane. When Rick reached the aircraft, the pilot gave a respectful bow of his head.

"Welcome aboard, sir," the pilot greeted.

Rick nodded in response as he climbed up the airstairs, with Amanda following closely behind.

The jet exuded luxury, with plush leather seats that were spacious and inviting. Rick settled into a seat in the back and gestured for Amanda to sit across from him. Amanda could hardly believe that her very first flight would be aboard a private jet.

Amanda felt a bit nervous as the plane took off. With each shudder and jolt, she tensed up, unsure of what it meant.

"Don't worry, it's completely normal," Rick said with a reassuring smile. Once they reached cruising altitude, he pulled out some papers and started working at the makeshift desk. It quickly became clear that this was a business trip, as Rick became fully absorbed in his work.

Amanda couldn't help but feel a rush of excitement as her pussy started getting wet at the thought of being on such a luxurious jet. It surprised her how this was making her horny. But with Rick so focused on his work, she had to use all her self-control to stay composed and not jump his bones. She even thought about offering him a blowjob but quickly dismissed the idea, too shy to make the suggestion. The last thing she wanted was for this business trip to be seen as anything other than professional.

Upon arriving in New York, another limousine was waiting to take them to their next destination. They were whisked away to downtown Manhattan, where they arrived at the Grand Hotel, one of the city's most luxurious five-star hotels.

Amanda waited in the grand lobby while Rick checked in. The interior of the hotel was just as elegant as the exterior, with chandeliers hanging from the soaring vaulted ceilings, fresh flowers in large vases filling the air with a pleasant floral scent, and soft jazz music playing from the hotel bar next door, enhancing the atmosphere. Rick received the key cards and made his way toward the elevator.

"Follow me," Rick said, and Amanda quickly followed his lead.

Rick inserted his hotel card and pressed the button for the penthouse suite. They waited as the elevator swiftly ascended to the top of the prestigious building. When Amanda stepped into the suite, her jaw nearly dropped. The room was nothing short of extraordinary, a stark contrast to The Roadway Inn. It offered stunning views of New York City's skyline and Central Park. Rick walked into the main living area and gestured toward the door on his right.

"You're in there," Rick said.

Amanda was surprised to find that they each had separate bedrooms, but it only reinforced that this was, in fact, a business trip. Rick headed left to his room, while Amanda entered hers. She quickly hopped onto the bed, feeling the luxurious comforter beneath her. The silk slipped through her fingers as she stretched out on the soft mattress. Luxury felt incredible, and Amanda couldn't help but think that she could easily get used to this.

After settling in, the two headed down to the hotel restaurant for a nice dinner. While they waited for the waiter to take their order, Rick said, "I've got a lot of work to do tomorrow. I won't need your help for this part of the trip. Feel free to relax at the hotel, grab some lunch, go sightseeing."

"What do you need me for? Why did you bring me here?" Amanda asked.

"I need you for Saturday night, but until then, enjoy the city," Rick said. Amanda smiled and ordered a filet mignon from the upscale steakhouse.

The next morning, Amanda slept in before spending the day exploring the city. She visited all the classic tourist spots, Times Square, the Empire State Building and the Statue of Liberty. At the end of the day to unwind, she relaxed in her room with a luxurious warm bath. She felt like a character from Pretty Woman in the oversized tub surrounded by bubbles.

Rick returned later that night looking a bit tired. He poured himself a scotch and settled onto the couch. Amanda entered the room in only a bathrobe, having just stepped out of the bathtub.

"How was your day, honey?" Amanda asked, her tone playful and flirtatious.

Rick smiled and took a sip of his scotch. "It was a long day, I'm going to head in."

Rick went into the bedroom and closed the door behind him. Amanda felt a little disappointed that he hadn't reacted to her playful, half-dressed appearance. Sighing, she retired to her own bedroom for the night.

Amanda woke up to find that Rick had already left. He left a note saying he would be back in the afternoon and to enjoy the morning. Amanda ordered breakfast in bed and savored the eggs benedict and mimosas that were brought up to her room. She decided to treat herself to a facial and a relaxing massage at the hotel spa. When she returned from her pampering session, Rick had returned to the room.

"How was your day?" Rick asked.

"It was wonderful, and sooooo relaxing," Amanda replied with a chuckle.

"Yeah, looks like you had a good time. I'm glad you had time to pamper yourself.," Rick chuckled in return. "Come get dressed. We've got a few things to do."

"What things?" Amanda asked, curious.

"We have plans tonight. I went ahead and got you a dress for the evening," Rick responded.

Amanda spotted an incredible gown hanging on the coat rack. It was another stunning ballroom dress, clearly expensive, with a shoebox placed neatly on the carpet below. Eagerly, she rushed over to take a closer look. Inside the box, she found a pair of exquisite shoes that perfectly matched the long, bedazzled black cocktail dress.

"Try it on. Let's see how you look in it," Rick said.

Amanda grabbed the dress and shoes and headed to her bedroom to try them on. When she emerged, she looked like a princess. The dress fit her flawlessly. As she stepped into the room, she found Rick already dressed in a tuxedo, looking as handsome and debonair as ever.

Rick paused for a moment, taking in Amanda's stunning appearance. Her beauty seemed to fill the room and he was truly impressed. In that moment, he couldn't recall ever seeing anyone more beautiful. Rick set his scotch down on the table and walked over to her.

"Wow, you look incredible," Rick said.

"Thanks to you, so, like, what's the plan for tonight?" Amanda asked, her expression clearly excited.

"We've been invited to another ball," Rick responded.

Amanda's stomach sank recalling how she had been treated at the last ball.

"The good news," Rick continued, "is that you're now a full member, with all the privileges that come with it and you'll be free to walk around and watch the initiation."

Amanda let out a soft sigh of relief, hoping tonight's event wouldn't be like the previous party. Amanda nodded her approval nervously. Although she was uncertain if Rick's was telling the truth, she also felt a surge of excitement and curiosity. Attending the party as a full guest intrigued her and she found herself eager to see what happened inside the other rooms.

Rick poured a glass of whiskey for Amanda and raised his glass in a toast. "To an exciting night."

The two clinked glasses. Amanda took a big sip and coughed, almost choking on it. The strong taste of the whiskey caught her off guard as it was rare for her to drink hard liquor straight. Rick chuckled, amused by her struggling with the adult drink. He took a large swig, showing her how it's done.

Rick and Amanda headed down to the hotel lobby where their limousine was already waiting for them. During the short drive to their destination, Amanda gazed up through the window at the towering skyline, mesmerized by the beauty and size of the big city. Once they arrived at a luxurious apartment building the doorman opened the door and greeted them, welcoming them into the impressive building.

In the lobby, a security guard stood watch in front of the elevators. He tipped his cap at Rick and escorted the two to a private elevator. Once the doors opened, he inserted his key card and pressed the button for the penthouse suite.

"Good evening, sir" the security guard said.

Amanda and Rick rode the elevator up to the penthouse suite. When the doors opened, they were greeted by two men in tuxedos, each wearing a masquerade mask.

"Sir, ma'am," the first man said through his mask, while the other man checked off their names from a clipboard he was holding.

Rick pulled two masquerade masks from his tuxedo pocket. The first was the same joker mask he had worn before. The second mask was for Amanda, who smiled as she took the mask from him. She quickly put it on, knowing it would allow her to attend the party anonymously. The elegant mask covered her eyes and nose but left the lower half of her face exposed. Its design had a delicate floral pattern that perfectly suiting her style.

"How do I look?" Amanda asked.

"Good enough to eat," Rick replied with a smile.

Amanda and Rick stepped into the luxurious apartment. Amanda was immediately struck by its vast size and grandeur. She could only imagine owning something so magnificent. It was filled with priceless artwork, crystal chandeliers, marble floors, and mahogany furniture, all of which adding to its elegance.

Rick led Amanda to a main room where numerous guests mingled. They were all impeccably dressed in tuxedos and gowns and all wearing masquerade masks. It was clear they all wished to remain anonymous. The excitement in the air was palpable, she could sense she wasn't the only one feeling excited. The two made their way to the bar and Rick ordered a double scotch on the rocks.

"What would you like?" Rick asked.

"Something fruity," Amanda replied.

Rick stifled a laugh before turning to the bartender. "Vodka cranberry," he ordered. The bartender nodded and began mixing a drink. He presented Amanda with a light red colored drink. Amanda took a sip and although she could taste the alcohol, the sweetness and flavor of it was pleasant. She had never been a big fan of alcohol, her taste buds too young to truly appreciate its mature flavors. However, this drink was delicious and she eagerly finished it.

"Shall we check out the place?" Rick asked. Amanda eagerly nodded, excited to explore the other rooms.

Rick and Amanda entered the hallway to the right and walked down the long corridor. They began to hear classical music playing softly ahead of them, which gradually grew louder with each step. When they entered the next room, Amanda's eyes widened in surprise. There were several people in varying states of undress, scattered throughout the room. On the couch was a completely nude woman riding a man reverse cowboy. Her animated movements caused her large breasts to bounce as a group of onlookers surrounded them. Nearby, another woman was lying on a pool table while two men fucked her, one in her mouth and the other in her pussy. She appeared to be enjoying the attention as several people stood and watched. In the far corner, near the fireplace, another fully nude woman was bent over as an older gentleman fucked her from behind. By the exit door, a man stood as a topless woman sat on her knees in front of him sucking on his cock.

Amanda clutched Rick's arm as he guided her through the room. They all continuing their sucking and fucking, paying no attention to them. Amanda and Rick moved to the next room, where even more people were naked and engaging all kinds of sexual congress. The atmosphere resembled that of an orgy, as ten people gathered around, fucking each other while others looked on. Amanda wondered if she was expected to join in. Just as she was starting to feel uneasy about it, Rick leaned in and whispered in her ear.

"You want to watch?" Rick whispered.

Amanda nodded in agreement as Rick led her to the side of the room, positioning them just in front of the couch. From there, they had a clear view of the orgy unfolding before them.

Amanda watched in fascination as two men fucked a girl on the couch, one from behind and the other in her mouth. The man fucking her throat drove his large cock in with force, each thrust unrelenting. Gagging sounds filled the air as thick drool dribbled from her lips with every deep push of his cock. The intensity of each thrust caused her mask to shift every time her nose hit his abdomen, misaligning the eye holes on her face. Yet, instead of resisting, the girl didn't try and push the man away. Instead, she calmly reached up to adjust the mask, seemingly captivated by the rough and unyielding throat fucking. At the same time, she was being fucked from behind by a towering man who looked like he could easily be a linebacker in the NFL.

Beside them on the couch, a man sat in a tuxedo, his fly undone with just his cock sticking out. Kneeling before him, a brunette fervently stroked his cock with both hands as she sucked him.

On the bearskin rug sprawled across the floor, three women were tangled in an intense lesbian tryst, their bodies entwined in a dynamic triangle. One woman straddled another's face as she lay back on the rug, while a third, kneeling between her legs, was tonguing her wet pussy.

Amanda could hear their moans and see the way they writhed, the pleasure radiating from them unmistakable in the open room. The scene sent a thrill through her, and she could feel herself getting wet. Just as she was starting to get horny, Rick glanced at his watch.

"Let's move to the next room," Rick whispered, gently pulling Amanda along with him. Amanda followed but kept her gaze fixed on the orgy. One man withdrew his cock from the girl's mouth and came all over her face and mask, while the other man fucking her from behind did the same all over her ass.

Rick and Amanda stepped into the apartment's largest room. It was a huge open space and had been completely cleared of all the furniture. At least fifty people stood in a wide circle, their eyes fixed on the empty center. Above them, more onlookers gathered along a balcony, peering down at the scene below. Though the circle remained vacant, Amanda immediately recognized the setup. It mirrored the arrangement she had encountered when she was brought in for her own initiation.

Rick led Amanda up a staircase to the balcony above. He positioned her in front of him along the railing, ensuring that they both had a perfect view down below. As they reached their spot, the room was plunged into darkness and a single spotlight illuminated the empty circle.

The same eerie music from Amanda's initiation began to play, its haunting melody sending a shiver down her spine. The sounds were seared into her memory, triggering a wave of unease that felt almost like posttraumatic stress disorder.

As she watched, a blonde woman stepped out from an adjacent hallway, her features eerily familiar, almost identical to the one from Amanda's past encounter. Behind her followed another woman, the only one in the room not wearing a mask. Amanda squinted, shaking her head in disbelief, as if she couldn't believe what she was seeing.

Amanda turned to Rick and whispered, "Is that...?" she asked before getting cut off.

"Shhh," Rick responded before giving a subtle nod of confirmation.

Amanda stared in shock as the subject of tonight's initiation stepped into the center of the ring completely nude. It was Alessandria, the world-famous supermodel.

Alessandria's beauty was indisputable, from the cascading light brown hair streaked with flawless blonde highlights to the luminous skin that graced the covers of countless magazines. Her posture was impeccable, every movement exuding the elegance that made her an icon. And for a woman who had never posed nude in her entire career, to be standing there completely exposed before nearly a hundred people was nothing short of astonishing.

Alessandria's hazel eyes held a worried look of apprehensive for what was to come. Her slender yet undeniably sensual frame was accentuated by her perfectly proportioned B-cup breasts. The only thing she was wearing were a pair of designer high heels, adding to the surreal nature of the moment. But it was her striking face, a captivating blend of English and Spanish heritage, that had made her a legend. It was well known that she had been discovered on the streets of Lisbon as a teenager, rising through the fashion world over the years to become one of the most coveted supermodels of her generation worth millions and desired by all. And yet, there she stood, completely nude, in the center of a room in a New York City apartment, about to be put through an initiation.

From the crowd, the man in the red robe emerged and began his ritual. He moved slowly, deliberately circling the two women, striking the floor with his scepter with each step. The cracking echoes reverberated through the room, each thunderous impact making Alessandria flinch. She was visibly trembling, her hands quivering from sheer nerves. Her breathing was unsteady and fear etched across her face as she braced for what was to come. The man in the red robe completed his circuit around the girls, before slamming his staff against the ground three times signaling the start to the initiation.

A side door opened and a group of men emerged, carrying the same red velvet chaise as Amanda's initiation. They placed it in the center of the room, its presence an unmistakable symbol of what was to come.

The blonde woman reclined on the chaise and spread her legs apart with deliberate confidence. She gestured to Alessandria to proceed, just as Amanda had been instructed to do a month earlier.

Alessandria hesitantly approached the masked blonde and lowered herself between the woman's legs. She moved cautiously, her mouth hovering near the blonde's open pussy. She peeked up, searching for approval and the blonde woman met her gaze and gave a slow, approving nod.

Swallowing her nerves, Alessandria extended her tongue brushing up against the blonde's pussy as she traced along the labia to her clitoris. The blonde woman let out a moan, her back arching in response to the sensation the supermodel had unknowingly elicited.

From Amanda's vantage point, all she could see was the back of Alessandria's head as she moved her tongue vigorously on the blonde's wet pussy. Her perfect, taut ass was on full display, accentuated by the position she was in. Alessandria's toned backside was pointed directly toward the spectators, a striking contrast to the vulnerability of the moment. Though Amanda was some distance away, she thought she caught the faint shimmer of moisture between Alessandria's legs, a subtle glisten that hinted at her excitement.

A warmth grew between Amanda's legs as she watched the scene unfold before her. Though she wasn't a lesbian and had never been particularly drawn to lesbian porn, there was something undeniably captivating about witnessing a world famous supermodel go down on another girl.

For several minutes, Alessandria worked with focused intensity, her tongue pressing firmly along the blonde's clit. The blonde, caught in the sensation, grasped Alessandria's head, pulling it closer, increasing the pressure between her mouth and pussy lips. As the tension built, her heavy breathing turned into gasps, her hips moving in rhythm with the deepening licking. The blonde's body arched, her moans rising in intensity until she finally cried out, and came all over the supermodel's face.

The man in the red robe struck the ground three times. Amanda glanced around, curious to what was about to happen next. Moments later, three men entered the room, each completely nude except for their masquerade masks. All three had large hard cocks, each at least nine inches long, that swayed with every movement as they walked forward toward the supermodel.

The first man was tall and powerfully built, his physique reminiscent of a swimmer. He had broad shoulders, chiseled abs, and a strong, athletic frame. His pale skin glistened under the spotlight, accentuating every muscle, including his nine-inch cock, its size impossible to ignore. Behind him the second man had a slightly darker complexion of Hispanic descent. His body was just as imposing, equally sculpted, with formidable sized cock. The last to enter was a towering black man. His cock was the largest of the three, easily exceeding ten inches, making it the most intimidating.

The three men advanced toward Alessandria, whose expression was that of panic. She was no virgin and had a well-known reputation for partying, but she had never been with more than one man at a time. Now she found herself in uncharted territory, expecting to take on three men simultaneously.

The first man stepped forward and presented his large cock in front of Alessandria's face. She paused, taking a deep breath before placing her hand over the stiff cock, giving it a few light stokes as if she were stalling while she weighed her next move. With a slight tilt of her head, she extended her tongue, delicately flicking the tip of his cock head before swirling it in an erotic display. Years of performing as a supermodel had trained her that if she had to do something in front of an audience, she might as well make it look good. Gradually she parted her lips, drawing him into her mouth with a gentle pull, her tongue swirling in slow motions as she continued lightly stroking it with her hand.

Alessandria was no stranger to giving blowjobs, having given plenty throughout her life. Now in her late 20s, having had several boyfriends, giving one was nothing unusual for her. Under normal circumstances, she would have welcomed the act, but this was different. This was the first time she would be giving head to complete stranger in front of an audience. And it was certainly the first time she had to handle one as large as the one now resting between her lips.

Amanda observed from above, captivated as the supermodel accepted the cock into her mouth. She knew this was merely the beginning, the easy part. A flicker of anticipation stirred within her, recalling her own experience and the challenge that lay ahead. Yet, for now, she simply watched, admiring the graceful composure on Alessandria's striking face as she sucked on the sizable cock with erotic flair.

Alessandria worked the cock, taking in several inches while maintaining a steady grip at its base. Her fingers stroked his shaft vigorously as she worked her head up and down, her confidence in her blowjob skills evident. Though the presence of an audience added an element of discomfort, she once again pulled on her experience as a model to remain poised under scrutiny. Drawing on that expertise, she set aside any lingering hesitation, focusing instead on executing the blowjob with some sense of grace.

After a few minutes, the first man stepped aside, making way for the second. The Hispanic man positioned his large cock in front of the supermodel, waiting for her to proceed. Once again, Alessandria reached out, her fingers wrapping around his shaft. This one, however, was uncircumcised. She carefully pulled back the foreskin, before allowing it to slip into her mouth.

This wasn't the first time she had sucked an uncircumcised cock, though the extra skin made for a distinct experience. She used the extra skin to her advantage, exploring it with her tongue as she bobbed her head along his length.

The Hispanic man placed his hands on either side of Alessandria's head and slowly he began to buck his hips forward driving his cock into her mouth. The unexpected intrusion into her throat took Alessandria by surprise, and the initial thrust triggered her gag reflex. A sharp, involuntary gag echoed through the room, the sound reverberating off the walls as she instinctively adjusted to the intrusion.

Amanda knew that sound well, and smiled as she continued to watch the spectacle below. The second man was more dominant than the first, forcefully driving his cock into the supermodel's mouth, thrusting it deeper until at least half had entered her throat. Alessandria gagged with each thrust, her body instinctively resisting the invasive blowjob. Desperate to control the depth of the cock, she reached up to push away at the man's stomach, but the blonde woman swiftly intervened, seizing her wrists and pulling them behind her back to prevent interference. Now unimpeded, the man continued, bucking his hips and thrusting his cock into her airway.

Amanda watched with fascination as tears welled in the supermodel's eyes before cascading down her cheeks in delicate streams. The thick mascara, once flawlessly applied, now smudged and streaked from the moisture, leaving dark trails in its wake. The contrast between Alessandria's ethereal beauty and the harsh intensity of the blowjob created an incredibly erotic sight, one that left Amanda mesmerized by the scene unfolding before her.

Alessandria struggled to maintain control. A brief wave of relief washed over her as the man pulled out and stepped aside, giving her a moment to catch her breath. But the reprieve was short-lived. The third man quickly took his place and presented his large black cock, easily the largest of the three. Panic rose in her chest at the thought of accommodating something of that size. With the blonde woman still restraining her wrists, she had no choice but to open her mouth as the black cock entered.

The third man immediately and aggressively drove his cock forward with relentless force. Unlike the first two, he was far more forceful, his power overwhelming Alessandria as she struggled beneath him. Gagging sounds filled the room with each powerful thrust, her body convulsing against the intrusion. He had already forced half of his cock into her throat and was determined to insert the entire length. As he slowed, he applied even greater pressure, pushing with all his strength to advance it further. Inch by inch, he pressed on, stopping only when just two inches remained. Panic consumed Alessandria as the large obstruction in her throat triggered violent convulsions throughout her body with each forceful advance. Every gag sent shudders through her torso, her muscles tensing uncontrollably in response to the unyielding invasion of her throat.

The sight and sound of Alessandria's body convulsions sent a jolt through Amanda's groin, leaving her flustered. She could feel herself getting even wetter and felt an almost irresistible urge to masturbate right there and then, captivated by the way Alessandria struggled with the black cock. But as she glanced around, she noticed everyone else standing still, their focus unwavering. Unsure of the protocol, she hesitated, unwilling to risk breaking it.

The first man moved behind Alessandria and positioned himself behind her with his cock in hand. He rubbed it against her juicy pussy lips then paused, waiting for the right moment to penetrate her.

Alessandria continued to struggle against the cock lodged in her throat. With one final, forceful push, the man applied all his strength, pressing against the back of her head in an attempt to get his entire length in. Slowly, the large cock slid further until her nose reached his abdomen.

At that moment, the man behind her swiftly plunged his cock into her open pussy. The sudden sensation sent a shockwave through Alessandria's body. With her hands restrained, she had no choice but to succumb to the simultaneous penetrations. Finally, Alessandra's head was released, allowing her to pull the black cock from her throat. She gagged as it slid out, gasping for air as she struggled to steady her breath. Thin strands of saliva stretched between her lips and the cock, glistening under the bright spotlight. Meanwhile, the other man continued his hard thrusting from behind.

Alessandria was utterly overwhelmed, drowning in shock and despair. Amanda could see the cock in Alessandria's pussy was beginning to have an effect as faint moans slipped from her lips. But those sounds were short lived and quickly stifled as the black cock was reinserted into her mouth.

Watching the supermodel get double teamed was an incredibly erotic experience, made even more so by the knowledge of her struggles. In an attempt to enhance her own excitement, Amanda pressed her pelvis against the railing. She used the pressure to push against her clit, seeking some form of stimulation for her dripping wet pussy. Suddenly, she became aware of something behind her the unmistakable sensation of Rick's cock pressing against her backside through his tuxedo pants.

Rick was clearly enjoying the scene, his hard cock proof that it was turning him on. He remained perfectly still, resisting any movement. Instead he let his cock rest firmly between the crack of Amanda's cheeks, separated only by the thin silk of her skirt. Meanwhile, Alessandria struggled mightily against the forces of the two cocks, her struggles intensifying with each thrust of the men.

With each forceful push from the man behind her thrusting his cock into her pussy, Alessandria was propelled forward, driving the black cock deeper into her throat. The relentless back and forth motion overwhelmed her, dizziness washing over her until she teetered on the edge of unconsciousness. However, just as it seemed to become too much for her, the cock would be pulled from her mouth, granting her a brief moment to breathe.

The fucking from behind intensified rapidly. The man pulled her hair from behind as Alessandria felt her orgasm building. The blonde slipped a hand beneath her, applying gentle stimulation to her clitoris in an attempt to increase her pleasure. This was too much for Alessandria who let out a piercing yell, her body reaching its breaking point.

"Fuck!" Alessandria screamed as she climaxed, every eye in the room fixed on her.

The two men stood as Alessandria lay exhausted, desperate for it to end. But instead, the Hispanic man stepped forward, replacing the first, and inserted his cock into her dripping wet pussy to begin another round of hard fucking. This continued until she was lifted into the air and placed on top of the Hispanic man as he reclined on the chaise. She was now compelled to ride him, her weary body shifting up and down the large cock. For a fleeting moment, she believed she had some control over the depth and pace of the penetration. But that illusion quickly vanished as she felt pressure from behind. The first man had repositioned himself behind her and aligned his hard cock against her exposed anus.

Panic surged through Alessandria as she attempted to break free. She had only tried anal sex once, years ago, but the pain had been unbearable, forcing her to abort the attempt almost immediately. Ever since, whenever a boyfriend suggested it, she had always refused. With a forceful thrust, he drove into Alessandria's ass, the large head of his cock breaching the tight resistance of her anal seal.

"AHHHH!" Alessandria screamed, the pain overwhelming. Her piercing cry echoed through the entire room.

Amanda imagined the scream was so loud that people in the other rooms must have heard it. Strangely, hearing Alessandria's despair only made her wetter. Though she could vividly recall her own ordeal in that very situation, witnessing the agony of the esteemed supermodel was an extraordinarily erotic sight.

Alessandria began to cry, her sniffles breaking through the tense silence as the simultaneous fucking of her ass and pussy proved to be too much for her. The sheer size of the two cocks overwhelmed her, leaving her with no choice but to endure and ride out the pain. Her breathing grew sharp and uneven, only to be abruptly cut off as the third man returned his black cock to her mouth. Now, she was forced to endure all cocks at once, something she had never imagined facing.

In perfect sync, all three men fucked Alessandria relentlessly, showing no mercy. Watching the supermodel take on all three cocks in such an intense and unyielding way was truly mesmerizing. Amanda could only wonder how they had managed to secure someone so highly coveted to be initiated and why she herself had been selected just last month.

The three men worked in unison, fucking Alessandria until every hole was numb. Utterly exhausted, she felt her resistance fading, overwhelmed by pain and the desperate struggle for air. Sweat coated her skin, shimmering under the harsh spotlights. Her strength faded away, her body wilting as she teetered on the edge of collapse. Just as she was about to lose consciousness, the men abruptly stopped and stood.

The man in the red robe stepped forward once more, striking his staff against the ground three times. At the sound, the side door swung open, and another group of nude men entered. Moving in perfect sync, they advanced methodically, encircling Alessandria. Now, twenty men of varying builds and statures with hard cocks stood in a vast, unbroken circle around her.

Alessandria whimpered at the sight, her body too drained to endure what was coming next. Completely exhausted, she had no strength left to resist. The blonde gently repositioned her, laying her flat in the center of the chaise. Around her, all twenty men began to masturbate in unison directly over her.

One by one, the men stepped forward. The first was the black man, who positioned himself directly over Alessandria, stroking his large black cock. She stared up, uncertain of what to expect, until the first burst of cum struck her face. She flinched instinctively but knew better than to resist. Keeping her mouth tightly shut, she remained still, allowing the man to continue unmoving.

"Open your mouth," the blonde instructed, directing the command at Alessandria.

Alessandria obeyed, bracing herself as the second blast struck her squarely in the nose. The third landed directly in her mouth, the taste of the black man's cum immediately coating her tongue. She fought the urge to gag, instinctively trying to push it out while keeping her mouth open. But as some trickled down her throat, she had no choice but to swallow.

After a few more shots landed on her face, he stepped back into the circle, making way for the next. This time, the Hispanic man moved forward, aiming directly at Alessandria. His strong shots of cum covered her face, sealing both eyes shut. Once he was done, he stepped back into formation. The Caucasian man next stepped forward and released a powerful blast. Most of his cum landed in Alessandria's mouth, coating her tongue before dripping down her chin and neck. She struggled to keep her composure, feeling the thick liquid spread across her skin. The man took his time, ensuring every last drop of his cum was delivered. When he finished his load, he shoved his cock into Alessandria's mouth for good measure, forcing her taste her own ass. She gagged at the combined taste of her own ass and traces of other men's cum, deepening her humiliation. Finally, he stepping back into the circle, making way for the next.

One by one, each man stepped forward in perfect synchronization, delivering a heavy load onto Alessandria's face. Every time cum landed in her mouth, she had no choice but to swallow. The sheer amount of cum she was forced to swallow was staggering. Each man's semen had a distinct taste, some thicker, some saltier, and after just a few, her stomach churned as she felt like she would throw up. With every swallow, she gagged, struggling to keep the sour semen down.

To add to her struggle, after each finished, they would shove their cock into the supermodel's mouth, forcing her to suck it clean. It insured that by the end of the night, she had given blowjobs to 20 men different men. As the 20th man approached, his precision surpassed the rest, every one of his shots landing squarely in her mouth. Alessandria swallowed once more, her body shuddering as she swallowed what was likely her fortieth dose of cum, struggling to suppress her gag reflex.

As the 20th and final man stepped back into the circle, the man in the red robe struck his staff against the ground three times, signaling the end to the bukkake and the initiation. Without a word, the men all turned and exited in a single-file line, leaving Alessandria lying motionless naked on the chaise, her face, hair, and neck drenched in cum.

Amanda stared down in shock and awe, struggling to process the utter transformation before her. The world's most famous supermodel, now completely unrecognizable, lay in absolute disarray drenched in cum, indistinguishable from the vision of perfection she once was. Amanda knew she could never speak of what had happened, though even if she did, no one would believe her. In a way, it felt like a fitting conclusion, watching the most beautiful woman in the world reduced to the most disheveled. Her face, so thickly coated with cum, she was barely recognizable. It was almost... a work of art.

Rick gently pulled Amanda aside as another man lifted Alessandria into his arms and carried her out of the room. Amanda trailed behind Rick, her mind reeling from having just witnessed the unbelievable. It was one of the most incredible, erotic, and disturbing experiences of her life. She could only begin to fathom the kind of power it took to orchestrate an event like this. As Rick guided her out of the main room and down the hall, she couldn't help but wonder what else was in store on The Business Trip.