The Next Playboy

I woke up the next morning with a soft smile. I was very satisfied with my previous evening, despite essentially being teased and not actually having sex. Kissing Janell had been wonderful. But Frank, Aaron, and I had a new problem on our hands. We had $30,000 and no idea what to do with it. We had all mutually agreed the previous night to sleep on it, but sleeping was done. I could hear Aaron typing away furiously for some reason or another and Frank tended to be an early riser. I got up.

After getting ready, I found both of my roommates drinking dark, dark coffee at our kitchen counter. They clearly wanted to be as attentive as possible for the next possible moves.

"So," Frank started, "I got a phone call."

"And?" I said.

"It was from Christiano Morgan," he answered.

"Who's that?" I asked.

"Angel investor," Aaron responded, "worth about $60 million and his company about twenty times that."

I perked up.

"He wants a meeting," Frank said, "but it has to be in New York. That's where his firm is."

"And you're sure it was real?" I asked.

"That's what Aaron's been checking," Frank said, "the actual caller was his secretary. We found her on Linkedin. It checks out. Also made sure his finances were legit. As far as we can tell, they are."

"And the new money pays for our flight," I said, "and we can afford to miss school?"

"For the potential of an investment, hell yes we can," was Aaron's response.

"What about a hotel?" I asked.

"He offered to comp it," Frank said.

"Really?" I responded in near-disbelief.

"Well he has the prospect of making millions off a stake in our company, so one hotel suite is not gonna set him back much," said Frank.

"So," I said, "who's ready to fly to New York?"

* * *

We booked a red eye for that evening and packed quickly. We didn't know how long we'd be staying, so we did so moderately. We packed enough for 3 or 4 days, including our fancy-ish clothes for the meeting (button-ups with dress pants). We woke up with $30,000 and by 8:30 we were in the airport with the prospect of millions.

The three of us were soon on the late flight. I was seated by the window with Aaron to my right in the middle and Frank by the aisle. Frank had elected for headphones and a book, but Aaron was full of nervous energy which made him talkative, which was a problem because I needed to put together a PowerPoint proving to Christiano Morgan that we were worth an investment.

"So, these Wall Street guys, what are they gonna be like?" he asked me.

"Like I know," I responded, "my closest experiences are with other business and finance guys at Stanford. From what I can tell, competitive, wickedly smart, and often times quite narcissistic."

"Do you think we'll fit in?" he asked sheepishly.

"Dude, you coded a high-class porn website for college students. You've done what these Wall Street nerds wish they could have. We'll be just fine. Now, this PowerPoint is not going to make itself, so you're gonna have to be neurotic on your own time."

That shut Aaron up.

We landed the next morning. Frank had slept, but Aaron and I were running purely on coffee and adrenaline. Our meeting was set for that day at 2 PM. We called an Uber and made our way to the hotel. It was 4 stars and close to the financial district, so practical, but not too fancy.

"So, who wants to go shopping?" Aaron asked with glee.

"We've gotta prep for the meeting, dumbass," Frank said, "I know your part is done, but I'm tweaking my portfolio and Mark is putting together a PowerPoint outlining future plans."

"And what are our future plans?" Aaron said.

"For now, the plan is for you to be quiet while Mark does all the talking," Frank answered.

He shut up again.

By 1:30 PM, we were set with our materials and walking towards Wall Street to be early for our meeting. We looked like real business people ambling down a New York street in dapper shirts and pants, even though we were just college students. Finally, we made it to Morgan's building. It was a skyscraper across from a very fancy looking hotel. We stopped in front of the doors and looked up. After acknowledging the magnitude of what was in front of us, we stepped into the building.

The lobby was ornate, with people bustling to and fro and busy looking assistants talking quickly. We spied the elevator and walked towards it like we knew what we were doing. To our surprise, there was an elevator attendant. She looked to be about our age.

"What floor?" she asked in a sweet voice.

"36," I responded coolly. She pressed the button and Frank, Aaron, and I did our best to prep ourselves for a meeting that could change our life.

The doors opened to another immaculate floor, this one filled with the offices of extremely high-level executives. All the offices had glass walls and we could see people talking urgently on phones and typing away at their computers. In the center was our destination, Christiano Morgan's office. It was easily the biggest and we could see him on his phone behind a huge desk. He was in a suit that was surely extremely expensive. We walked towards the office with as much confidence as we could muster.

Soon we reached the door and Morgan saw us. He said a few more words on the phone then hung up. He smiled warmly towards us and waved us in.

"So, you must be the Voyeuristic people!" he said.

"We are," I nodded, smiling back.

"Well, I won't hold you up! I want to hear your proposal!" he said.

I pulled out my flash drive and he immediately called in his secretary to set it up on the tv in the room. I pulled up our first slide.

"So, we have seen growth at about..."

I talked for about 15 minutes about our current success and plans to expand as well as the kind of media we would like to create. Morgan was receptive the whole time, nodding and adding little "hmms" here and there. I outlined our plans to purchase our own photography studio and begin scouting models at college campuses across the country. We would employ more people like Aaron to expand the website, clean it up, and make more content faster. We would employ more photographers and social media experts to give us online presence. Finally, I got to our kicker.

"And finally, a portion of an investment would go towards something that would be recognized nationally. It would instantly become iconic. Phoebe-Cates-in-Fast-Times iconic. We want to start doing nude shoots with celebrities," I said, then looked right at Christiano to gauge a reaction. He sat and thought for a moment.

"You really think a celebrity would go nude?" he asked with his slight accent.

"For the right price. Think about it. Touring, filming, and press are all hard work, but you know what's easy? Getting glammed up for a single day and having some people take pictures of you," I responded.

"And what sort of price tag would you put on this?" Christiano asked.

"We'd lowball them starting at around $100k first, but we'd probably be looking more at the $300k-$500k range once all's said and done, but people would pay good money for these pictures."

"And what stops people from just sharing it with their friends?"

"That's where Aaron comes in. We already have some restrictions on sharing on our website. No screenshots, no downloading, no printing, no sending. Pictures are only available on our website with a payment, similar to OnlyFans."

"And who did you have in mind for your first shoot?"

"We're thinking big, something that will put us on the map, high risk, high reward. We're talking about doing a nude shoot with Ariana Grande," I stated proudly.

Christiano mulled it over for a few seconds.

"Your business plan is solid. Your numbers are impressive, but this celebrity thing is a long shot. I mean, the idea that she would even respond, even for a large number. I mean, it's potential money means nothing to these people with how much they have," he said, almost to himself.

"How much money do you have?" I asked.

"About $65 million," Christiano answered.

"And why are you thinking about investing in our company?"

"Because it might make me more money."

"Exactly. Money always has value, more value than some sort of mystique around nudity," I said, "we're looking for a $10 million investment for a 12% stake. We can have the Ariana Grande content out by the end of the month, plus a springboard on hiring models, techs, and photographers. Once that celebrity issue comes out, we're on top of the world."

Christiano seemed to be mulling it over again.

"I'll give you $9 million for a 14% stake and the celebrity issue comes out in three weeks," he said finally.

"Done," I said without a second thought. I walked over to his desk to shake his hand. As I stepped towards him, he got up and walked to meet me in front of his desk and he pulled me into an embrace, which took me by surprise.

"Come on! The hard part's done!" he said with glee, "the four of us are going to make so much money! Let's throw a party!" He pressed a button on his desk. "Liz, rent out the Ritz-Carlton rooftop for a party tonight and invite the usuals. We're going to celebrate!"

Christiano then walked us to his office's door with his arm around my shoulder. Frank, Aaron, and I were just kind of in awe. We had no idea what we were in for.

* * *

After a few hours worth of paperwork, we quite literally had $9 million in our bank account. It was a wire transfer that took five seconds. I talked with Aaron so he would soon set it up so only I had access. I loved Aaron, but I knew he could lack judgment sometimes. Then, we went on a small shopping spree. We stopped at Sak's, Burberry, Saint Laurent, you name it, and pulled a few items. I got myself a fancy Moncler coat while Aaron decked himself out in a flashy Dior button down. Frank flew a little more conservative, opting for a quaint Burberry sweater that fit him perfectly. Afterwards, it was time for the party.

Entering the Ritz-Carlton was like walking into a dream. Like stepping into the very pages of an F. Scott Fitzgerald novel (though perhaps without the ending of those novels). Wondrous chandeliers and bellhops dressed to the 9's abounded. We hadn't taken a step in when a clerk stopped us.

"The Voyeuristic people?"

"Yeah," I said.

"You're VIP, right this way," the clerk said and led us to a large elevator. We all stepped inside and he pressed a button that said 'ROOF.' Aaron, Frank, and I were electric with anticipation. What was a real fancy party like? Frank being excited meant this really was a big deal. I mean, we were millionaires now (ok kind of. Most of that money was going to go back into the company).

The elevator doors opened to what looked like a scene out of The Wolf of Wall Street. There was a huge view of the New York City skyline with champagne glasses left and right in the hands of the most gorgeous women we'd ever seen. Christiano was right in the middle. He saw the elevator doors open and immediately opened his mouth to exclaim, "Everyone, quiet!"

The room silenced. We had probably 100 eyes on us.

"These boys are going to build a huge company with me! Everyone, show them some love!"

The crowd of mostly women cheered. All of our faces went red, but we smiled to the crowd begrudgingly.

Before the party could resume, Christiano said one last thing, "alright, let's show these boys a good time!" Another cheer and raising of glasses and immediately we had a circle form around us. Aaron and I walked to one of the small tables outside as a host of models followed us and were complimenting us on our clothes and hair and such. Frank walked over to some of the guys in suits and struck up some conversation.

The first girl on my left put out a hand for me to shake.

"Hi, my name's Kellie," she said with a smile. She was about 5'10" and blonde, an absolute delight to look at. She was definitely a model, wearing what was probably a custom dress and heels.

"I'm Mark. What do you do?" I said, trying to be polite.

"This, mostly," she responded.

"What do you mean, 'this?'" I asked.

"I model and go to parties," she said.

"That sounds like a good life," I said.

"It looks like your partner over there is bonding with my friend, Erin."

I looked across the table to see Aaron laughing it up with another tall blonde, this one with bigger breasts and lips. She was definitely a model too. She had sharper features than Kellie. Kellie's face had some softness to it, Erin was all model. She also had an evening gown on, hers bright red to match her lips

"We model together a lot," Kellie told me, "don't get fooled by all this, though, a lot of these girls aren't models or anything. They have 10,000 followers on Instagram and got invited by a guy. We've modeled for GUESS and Louis Vuitton."

"Would you ever be interested in modeling for us?" I asked.

"We'll see," Kellie responded slyly. By now, the crowd had died and the girls were mostly talking to each other.

"Ya know, I haven't been around this many beautiful women before," I said.

"You'll get used to it," Kellie said, "I can tell you guys are newbies, but sometimes that can be charming. Some guys are in this too long and it all goes to their head."

"Huh, I'll try to avoid that I guess," I responded.

"Best way is to focus on conversation, not looks," she said.

"And what do we talk about?" I asked.

"Life," Kellie answered, "what made you want to start a softcore modeling website?"

"We were horny," I answered truthfully.

"Hey," she smiled at me, "no shame in that." As she said this she touched my arm with her free hand (the other had a champagne glass).

"Um... I hope it's not rude, but how old are you?" I asked.

"24," she said, "I can tell you're a young college boy, but that's fine. Sometimes young boys get to do big things."

Was that a euphemism or was I just horny? I looked at Aaron and he was still laughing with the dimepiece on his arm.

"You know..." Kellie started, "Christiano booked a presidential suite for you guys in case you ended up spending the night. I don't think your friend and mine would say no to joining us there. The crowds and noise can get a little..." she paused and leaned in to whisper in my ear, "hectic." I just about did a spit take (without a drink in my hand too!). This could not be happening.

I walked over to Erin and Aaron, which I just noticed was a funny combination of names, and repeated Kellie's inclination, "Hey, Christiano booked us a fancy suite here and we were gonna go there to get away from the crowd."

Erin immediately grinned widely at Kellie. I couldn't help but think this wasn't the first time they'd done this. Aaron also looked pretty damn happy, so there was that. Kellie grabbed my arm and led the way.

We walked back into the elevator and she took us down one floor to where the best suites are. We walked down the luxurious hallways, all four of us, me with Kellie on my arm and Aaron with Erin on his. Finally, we reached room 1124 and Kellie opened the room with a room key. All of a sudden, we were treated to the sight of the most luxurious room I've ever seen. Gold and red everywhere, a giant bed, and the kicker: a hot tub with a window view of the city in the same room as the bed.

"There's a second bedroom over there," Kellie pointed across the large hotel room to a door, "but for now, I say let's try out the hot tub."

"We don't have any swimsuits," Aaron said.

"Who said anything about swimsuits?" Kellie said with a grin. Then she turned to me, "unzip me?"

Aaron and I were stunned.

"Um, uh, yeah," was all I could muster. Then I forced my body out of shock mode and started unzipping Kellie's dress. Aaron was excitedly doing the same for Erin. Soon, both girls were in just their bras and panties, a matching set of reds. God, they knew what they were doing.

"Why are we the only ones getting undressed?" Erin said as she unsnapped her bra. Aaron and I quickly began taking off our shirts as the girls removed their lingerie. Before we could sneak a peek, both of them were in the hot tub with their cherry undergarments strewed across the carpet. We got our shirts off and fumbled to undo our pants. We clumsily got ourselves down to our boxers.

'Come on, boys..." Kellie beckoned with her finger. Aaron and I pulled down our boxers and stepped towards the hot tub. We both felt a little shy getting naked in front of girls, let alone models that we barely even knew. We finally got through the nude walk and waded into the hot tub, which could comfortably fit six, so with just the four of us, there was plenty of room. I drifted towards Kellie and Aaron drifted towards Erin. We all just sat there naked for a second before Kellie broke the tension by wrapping an arm around me and planting some kisses on my cheek. Erin took her cue and pulled Aaron into a full-on makeout. I turned my head and pressed my lips to Kellie's. She didn't waste any time and stuck her tongue in my mouth immediately. Soon, we were locked in a passionate makeout session. I wrapped my arms around her and began feeling up her bare back, letting my hands drift close to her butt. Suddenly, she broke the kiss.

"How about a switch?" she said.

"I like that idea," Erin responded and floated over towards me for another passionate liplock. Erin kissed differently, with a little more fire. I was really tempted to reach out and fondle her soapy tits, but stopped myself and just enjoyed the kissing. Erin's luscious lips felt great on mine. I broke the kiss kinda soon so I could look at Aaron swapping tongues with Kellie, both very much enjoying it. Erin then tapped on Kellie's shoulder. Kellie broke her kiss with Aaron as Erin pulled her in so the two girls could make out. They wrapped their arms around each other and began what I would guess was not their first makeout session. Both Aaron and I leaned back and enjoyed the show.

"Mmmmm," Kellie moaned, "you wanna take the other room?" she said to Erin. Erin gave her a little nod. The girls broke apart and Kellie waded towards me and Erin waded towards Aaron.

"Come on, stud," Erin said and she stepped out of the hot tub, showing off her soapy bubble butt. Aaron got out and was right behind her. Kellie and I watched them until they made their way to the door and closed it.

"Now it's just you and me, honey," Kellie said and resumed our making out. Her tongue played with mine as my hands roamed her body. Suddenly, I felt her hand rub against my very hard cock. "Did I do that?" she asked as she gave it some light rubbing.

"Oh, yeah," I responded.

"Sit on the edge of the tub," she commanded. I quickly pulled myself out while she stayed in. Now my hard cock was free to the air and I felt the cold sting of the air in the hotel room. Kellie began jerking me off and quickly added her tongue into the mix. She licked the underside of my cock before putting the tip in her mouth and letting her tongue run along the sensitive areas there. For the first time, I had a good look at her tits. They were shining from the water and were absolutely beautiful. Two sizable mounds topped with light brown areolas and pink nipples that just begged to be sucked.

"You like that, Mark?" Kellie asked seductively as she jerked my cock.

"Yeah, baby," I responded.

"Let's take this to the bed then."

I wasn't gonna say no to that. I got up and grabbed a towel hanging by the side of the hot tub. Kellie got out behind me and I handed her another towel. As we dried ourselves off, we heard grunting noises coming from the other bedroom. Kellie and I looked at each other and laughed. We finished toweling off and I let her lead the way. She strutted to the bed, showing off her model moves and laid down on her back, letting me see her whole body. Her pussy was totally shaved, pink and perfect. My hard cock was pointing straight up as I stared at this goddess with a perfect body waiting for me.