This S.O.B. System

CHAPTER 42 VACATION



Asher’s folks dropped him and Tiffany off at the airport early the next day. They said their goodbyes and were soon on a plane to Atlanta. Unfortunately they were unable to join the mile high club. She assured him there would be plenty of chances in the future. Flying first class was a nice consolation prize. 

 

When they arrived in Atlanta they almost missed their connecting flight, but made it just in time. As they were rushed in the plane they finally saw her. Zora sat worried in her seat until they yelled her name. She beamed a smile. 

 

Asher was disappointed to be stuck across the aisle while the 2 girls caught up. Though they talked daily there was still much to catch up on. They spoke in whispers about the trip. What they brought. What they still needed to buy. He fell asleep listening to them yammer on. 

 

Once they landed in Miami Tiffany finally spilled the beans that they were going on a couples cruise down to Mexico. Glad he had bought some props he wondered when the best time to use them would be. 

 

They stayed in a high class hotel on the beach. Near the top floor they checked out their room, dropped Zora’s luggage off, had some sex, then went out to the beach. Working on his tan at the beach the girls did the same, but a part of him doubted Zora would ever get one. Her skin was a perfect pale white that he and Tiff loved. 

 

When they were done swimming and tanning they went to a high class restaurant and dressed up. Tiff of course demanded new dresses so that was thrown in there somewhere. Tiff kept pulling out cash as they spent money on whatever they wanted. After they found out they could buy Monopoly money online it had been easy to Roleplay it. Most of it was from when they had decided to have sex in a pile of money. It was interesting to be having sex on the paper Monopoly money one second then real money the next. 

 

That night they had more sex, but not near as much as usual. Jet lag was affecting them all. But it was still worth it to have them in his arms all night. Asher didn’t sleep much anymore with his stats so high, so the next morning he brought them breakfast and enjoyed his vacation. No fights or training to worry about. He simply lived in the moment. It was odd to have a thought about doing something and being able to do it. Very freeing. 

 

Within a few hours they were on the cruise ship. Asher was amazed at the size of the room Tiffany booked. It had a king size bed. Spacious living area. Even a small hot tub. The wonders of what money could get you.

 

 

Jack nervously waited outside the room. He was in the upper class area, and could be kicked out at any time. Wearing a white button down shirt with brown pants and suspenders, he did not belong there. Yet he was, because he was in love. 

 

He had met them on his first day of the cruise. 2 friends on the cruise together, they were from the upper class and he the lower. Day by day they ran into one another. Sometimes one on one, mostly they were together. He flirted. They laughed or gave him shit. Despite his inability to give them anything they deserved they came back for more. 

 

It wasn’t till he saw them kissing that he understood their true relationship. Their intimate moment only made him want them more. After some innocent discussions about his art they agreed to let him try it on them. Now he waited for them to be ready. 

 

Once there was a knock at the door he took in a slow breath and walked in. The room was bigger than he imagined. He had to share a room with 6 others down below in a room not nearly half this size. 

 

Sketch pad in hand he let himself in further. That’s when he saw them. They laid entwined on the bed smiling at him. The taller one had pink hair on one side and blue on the other. Both colors he had never seen before on a person. Her skin was smooth but he could see muscles flexing as she moved. Her breasts were C-cup and a delight to look at. 

 

The other girl had bright blonde hair that was almost white. Tied in a braid at the back her small breasts and pointed nipples drew the eyes to them. Both girls were hairless at their sex. They also had large purple diamond heart shaped necklaces hanging from their necks. They had said the necklaces were one of a kind. If so, how were there 2? 

 

Mostly laying there on each other he could tell they had never done this before. Then he began to act like the professional he was. Walking around the foot of the bed he stared at them at different angles. When he finally found one he liked he moved a coffee table to sit on. 

 

As inspiration came to him he moved their girl’s arms and legs. Turning their faces toward him he found the perfect angle for what they asked for. Zora closer to him she faced up looking into Tiff’s eyes. One leg bent helped hold Tiff at the right angle. Tiff leaned over Zora a little staring down into her eyes. Her arm was on the small girl's waist. A leg was draped over Zora’s prone one. 

 

Then he began to sketch it. A part of him really wanted to take a picture with his phone, but this would have to do. As he worked the girls shifted slightly. Tiff made jokes and Zora tried to hold herself in. Jack mostly ignored them, burning the image into his mind. 

 

As he began shading he knew they were about out of patience. A part of him said it was close enough and began to raise his pheromones. Putting on the finishing touches, by the time he was done the girls were kissing one another. 

 

Ever so slowly they inched closer and closer. They forgot what they were doing and focused on one another. Mouths opening wide slowly they were kissing deeply. The girls moaned into the others mouths. Zora’s legs wrapped around Tiff tightly. Her small body instinctively humping the other woman. 

 

Tiff's breasts then ballooned out. Zora smiled happily as they pressed their breasts together. Zora on top, Tiff was still in charge as she groped her lover's ass. Pulling her up to her face. 

 

Zora complied. Slowly inching up until she was mounted over her head. Legs straddling ears she leaned against the headboard to hold herself up. Then the tongue was in her. Snaking it’s way inside the dripping wet hole. First it stuck to the left. Then the right. Always moving, she was soon cumming. 

 

Jack couldn’t hold back after that. Setting his pad down he put his head between Tiffany’s legs and began his own work. Licking her slowly he didn’t want her to cum right away. The exotic woman groaned inside her girlfriend's legs with each slow lick of his. 

 

Zora breathing heavily again, Jack sped up. He was able to time it just right as both girls came together. Taking off his clothes he was instantly mounted back between Tiff’s legs. Her long tongue still moved inside the dripping wet pussy of her girlfriend. Zora was now facing him so they kissed. 

 

His long dick entering Tiffany he pounded her as his mouth filled Zora’s with his tongue. The small girl came another 2 times before she needed a break. The System users had told her more than once to pace herself, so they were proud when she told the truth. 

 

Soon Jack and Tiff were going at it harder. He didn’t try to be quiet as he pounded into his lover with all he had. The bed shook as they came again and again.  When Zora was ready to join the fray once more he ignored the notification and entered her from behind. 

 

She began licking Tiffany. Digging inside her for his cum with everything she had. As he leaned over her back pounding her from behind muffled screams came from her. “I’m going to put a baby in you,” he growled in her ear. “You make our girlfriend cum so I can fill you up. You’re so tight. Please let me fill you up. Make Tiffany cum and every drop of my seed will be in you.” He locked eyes with Tiffany as Zora began to redouble her efforts. Tiffany’s eyes fluttered and all 3 came together. 

 

Only by the pounding on the wall were they brought back to the present. They had been extra loud that time, and it was only the first night of the cruise. As he broke character he announced. “Congratulations girls. You now have your very own Heart of the Ocean necklaces. 

 

“Woohoo,” Tiffany said, raising her hands in the air in faux enthusiasm. He laughed as he slapped Zora’s ass. They still had a lot to do during the next few weeks. 

 

Prop Manifestation Success

All conditions for prop manifestation have been met.

Rewards:

Heart of the Ocean Necklaces x 2

 

 

Sketching (LVL 8)

Not as cool as painting, or most any other art form. This will still allow you to not rely on stick figures to convey a picture.

 

— 

The first real day on the cruise Asher woke up to a morning blowjob. At first he didn’t know what it was, but as his mind cleared he felt the wet mouths on his crotch. When he was finally awake he looked down to see 2 girls working on his large member. No words were said as Tiffany took him in as far as she could, nearly to the base. Then she would come up for air and begin to lick the head. 

 

Zora’s eyes were locked on his as she licked one of his balls. He groaned at the view letting Tiff know he was awake. Her eyes shot open and gave him a smile with his dick in her mouth. “Mwerning,” she said with her mouth full. 

 

“Morning,” Zora said happily. 

 

“Morning, ughh,” he groaned as they began again, going faster now. Zora still on his balls she fit it all in her mouth and began gulping it. Tiffany began going deeper down him. Her Body Control skill came in full force as she took him to the base with only a small gag. 

 

He groaned and moaned at the feeling of them both on him. His lower body bucking. “So seeex?” He asked, the word drawn out as Tiff raised up. 

 

“Of course,” Tiff said, plopping off of him. “After our morning cumshot.” She then kissed his dick slowly moving down to the base. Taking the other ball in her lips the girls swirled both in their mouths. Once he had groaned enough Zora moved up to his head. Only able to take a few inches down she gave up and licked the tip like a sucker. Her tongue swirled around the head. 

 

His dick began to twitch under all the pleasure. Tiff began kissing her way back up his length and was soon making out with Zora. His dick was caught in the middle as their tongues caressed one another’s. Tiff’s shot out and entered Zora’s mouth on the bottom of his dick head, and Tiff’s licked the top. 

 

In seconds he was cumming. Spurt after spurt shot out on their cheeks and his chest. Tiff sucked the head to get the last shots. “Mmmm coffee,” she said as Zora and she began to lick the rest up. 

 

Usually they stuck to sex, but the intense double blowjob caused Asher to have to catch his breath. He doubted he had ever cum so hard. When they had licked one another clean Zora mounted him first. Slowly she took him in until, surprisingly, she was all the way at the base. She moaned resting on his crotch as Tiffany began licking Zora’s nipples. 

 

Tiff then moved her crotch to his face. Raising pheromones and libido he was buried in her pussy for the next 10 minutes as Zora jumped up and down on his dick. He assumed they were kissing as he heard muffled gasps and groans above him. The only thing that existed to him was his girlfriend’s lower lips on him. 

 

When he came inside Zora twice she finally fell off. Tiffany then jumped on. Going all the way up then slamming down on his dick he never lost his erection. After he came once he felt something on his balls, sucking them again. Amazed at the feeling of his dick in Tiff’s soaked pussy and a ball in Zora’s mouth he stopped thrusting into Tiff to let her work. 

 

Tiffany eventually noticed her back there and leaned forward. “You’re so greedy Zora. You want our boyfriend’s cum so bad you’d lick it out of my pussy wouldn’t you?” He felt Zora nod with his ball in her mouth. Then she began to. Licking up the bottom of his dick she swirled her tongue around it and licked up to TIff’s cunt. Sucking up their cum as it leaked out Tiff and Asher stayed still for a moment, reveling in the feel of her.  

 

They began to groan as she continued. Asher pulled Tiff’s face down to his own and they kissed. Their tongues caressed one another’s as Zora’s explored where their sexes met. Asher was cumming in seconds. His urethra bulged as semen poured into Tiffany. The feel of it then made her start to cum. “Put a baby in me,” Tiff whispered as he shot another thick spurt inside. He wanted nothing more than to do that right then. 

 

After the short session Asher put on his swimming trunks and a Hawaiian shirt as the girls ate one another out. The coffee taste was well received in the morning. He smacked their asses to draw attention. “Let’s get a more substantial breakfast and go swimming. I want to see my girlfriends in their swimming suits.” They begrudgingly agreed. 

 

His shirt was left open, after the girls voted for it, so he showed off his thick muscles. They bulged with each movement. Asher’s physique was a far cry from the skinny muscular guy, now he was thick with muscles. The girls donned their bikinis and commandeered some more of the Hawaiian shirts he bought for the trip. 

 

Tiffany’s bikini was a 2 piece. The top was blue, the bottom pink. She had mixed and matched till she got the right shades at the store. Her large breasts bulged against it, drawing his and Zora’s eyes. Neither knew it but they both licked their lips at the sight of her. Her toned muscles and mildly tan skin were a testament to her beauty and stats. Zora wore a white 2 piece that covered a little more skin than Tiff’s. Her long hair braided back, pale white skin, and straw hat made her look extra cute. 

 

They walked out in a line. The larger rooms had much wider hallways too, so they didn’t have to shuffle much to get around people. They grabbed some breakfast at a buffet and were soon swimming at a pool on the deck. 

 

When they finished swimming Asher was rubbing lotion on Tiffany’s back as she rubbed it on Zora. “What should we plan to do on the islands?” Tiffany asked. He began to knead her muscles. 

 

“Where are we going again?”

 

“Nassau, Cozumel, Mexico somewhere, then back to Florida in a week,” Zora said. Tiffany had begun kneading her shoulders. Asher liked the idea so he began doing the same to Tiff. 

 

“I want to swim with dolphins,” Zora added. 

 

“Ooooh I like. I saw there was rock climbing and jet skis at one,” Tiff offered. “There were Mayan ruin tours too. Anything catch your fancy?” 

 

“Only 2 things catch my fancy,” Asher said, kissing her neck. 

 

“Oh stop. We can do that later,” Tiff said, but didn’t shake him off her. 

 

“I saw they had bingo,” Asher offered. 

 

“You old man,” Tiff said. 

 

“There was a cash prize for the winner,” he added

 

“I’ll put it on the list,” she said. Money always swayed her. 

 

Though they meant to tan, Zora leaned back laying on Tiff and Tiff did the same to him. So the throuple enjoyed the warm air laying on one another. Before he knew it Asher woke up to someone yelling, “Ho down there.” 

 

Asher opened his eyes to see a very chiseled man yelling down to them. On a deck above he leaned across the glass staring at them. He wore white shorts and a button down shirt opened like Ash’s. “Ho to you,” Ash yelled. The girls were soon waking up too. 

 

“Why don’t you beauties come join us up here,” he yelled. 

 

“We have a boyfriend, but thanks,” Tiff said. 

 

“I was talking to your boyfriend too,” he said confidently and turned away. 

 

The trio looked to one another and shrugged their shoulders. Getting up with a groan they headed toward the stairs leading to the upper deck. Still early, the cruise was quiet. They didn’t run into anyone as they were soon at the upper deck. The area had another pool, just not quite as large, but there were also curtained off sections. 

 

One curtain open they tentatively walked up to it. Inside were 3 other girls and a man. The man welcomed them in. “Hello my friends,” he said happily. “Thank you for joining us. I am Nadir, these are my wives Maya, Advika, and Pari,” he said pointing at the beautiful women. They were very exotic. Dark skin, darker hair, and perfect skin. They wore bikinis that showed off their bodies exquisitely. He and his girls may have stared a little too long.

“I must ask, what brings the famous Asher Whitmore on this fine cruise?” Nadir asked casually. 

 

“You know me?” He asked surprised. 

 

“Of course. We people in the System try to communicate clearly. It was quite big news to form a System Guild, defeat a trial, and get titles. Sit please,” he said pointing at some cushioned chairs across from him. Asher then looked at him. His girls had been smart enough to bring sunglasses, but he hadn’t. The only ones he had were the Inspection sunglasses. In front of him, over the man’s head it read. 

 

Human 

Level 17

 

“Still, I don’t think it's enough to become famous,” Asher said, trying to relax. 

 

“Well, maybe not famous, but I try to know who's who in the world. Consider me an outlier. But now I see they are true. Level 16, I’m quite jealous. It took me years to get this high of a level,” he admitted. 

 

“Been lucky,” he admitted. “How can I help you Nadir?” Asher asked skeptically. 

 

“Me? You see my wives? I don’t need anything. And you, my lord those beautiful women on your arms, I don’t think you need for much either. I simply like to know people. Share information. Consider my surprise when someone who I had a report on showed up to sunbathe a floor below? I like to think of it as fate.” He stopped looking around to everyone, then a thought struck him. “Look at me, I sound like some war lord. Let’s start over, girls,” he said. Then his wives began to talk a mile a minute. Introducing themselves, Asher was shocked for a minute. He assumed they were simply eye candy. Then they were talking Zora and Tiffany’s ears off about what they were wearing, what did they do to her hair, what their plans were. 

 

“Asher, do you have many plans for your trip?” Nadir asked as the girls talked. They too were discussing swimming with dolphins. 

 

“We were talking about that. Honestly, this is my first time out of the states. Do you have any recommendations?” 


Nadir nodded, “I might have a few.”


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