For a three day trip.
Yes, dating a billionaire meant that she had to recalibrate how she assessed the costs of various things. In fact, she didn’t have to assess prices at all. In her new world, money just didn’t matter. She still couldn’t quite believe it.
Lisa was a good friend and didn’t sound at all jealous as Gin showed off her new clothes in the living room of her apartment. Lisa was in a beat up old recliner sipping a merlot, while Gin did her best not to get her new clothing dirty.
When Gin finished, she sat down on her sofa and took a long drink from her wine glass. “It’s kind of surreal,” she said as she put her glass down.
Lisa stared at her for a moment and then smiled. “Look, just promise me you’re not going to go all new Gin on him.”
“'New Gin?' What the hell do you mean by that?” Gin glared at her friend.
“Look, you to tend to make guys work pretty hard for the goods these days, if you know what I mean.”
“Well, it’s been working.”
“Gin, all those years when you acted like a total slut worked, too. When are you going to get it through your head that guys just plain like you?”
“Hey, you acted the same way.” Gin frowned. “And we weren’t sluts. We just liked having fun.”
“That’s what I’m talking about. You’re not exactly a slut if you fuck the guy flying you to Venice for dinner.”
“Jesus, Lisa. I’m not a whore either. This is not a quid pro quo thing.”
Lisa sighed. “I’m not saying it is, but Phillip is flying you to Venice. Venice! I’m not saying you need to sleep with him, but at the least give him a blowjob. That’s just polite.”
“I can’t believe we are having this conversation. It’s not some prom in 1967, Lisa.”
“And this isn’t some grad student taking you to In’n Out for burgers. The rules are different. Do you really want to risk losing a billionaire by making him wait one more date for a blowjob?”
“Do I even want to be with a guy who breaks up with me because I make him wait for a blowjob?”
“Don’t be naive, Gin. That’s every guy.”
What bothered Gin the most was that her short experiences with extreme wealth told her that Lisa was probably right. Even if there was no expectation of “I fly you to Italy so you can sleep with me,” there was this kind of casual approach to everything… money, time, distances, clothes, and probably sex. Everything seemed to be just taken for granted.
Gin said goodbye to Lisa not knowing how she’d handle herself, but the idea of just jumping right into bed with Phillip, who was handsome and athletic and sexy—and flying her to Italy—was something she no longer dismissed out-of-hand.
chapter seven
There was a knock at the door and Gin took a deep breath. She looked down at her two bags and closed her eyes. Relax. You’re going to Italy for a date. This is not a big deal for a billionaire. Don’t make it a big deal for you. She opened the door. Phillip stood outside with a stylish business casual outfit on. Designer jeans, loafers, and a tailored cotton shirt. His enthusiastic smile just killed Gin. How can someone so rich be so attractive?
“Can I help with your bags?”
“Oh, sorry. I was just kind of thinking if I forgot anything.” She picked up her bags, and as she went to move forward Phillip grabbed them.
“Here, let me take them to the car while you lock up.”
Gin locked the door of her apartment and followed Phillip to his car, a pristine Tesla Roadster. She looked around her beat up neighborhood and felt a bit embarrassed. She hated the idea of this turning into a Cinderella thing, but it was practically impossible not to think that way when looking at Phillip walking down a crumbling sidewalk to his expensive car.
He held the door open for her after tossing her bags in the trunk. “Did you end up seeing Jules?”
Gin’s jaw dropped open. She was wearing the first outfit Jules prepared for her. It probably cost more than five thousand dollars. “You really don’t notice details like that do you?”
Phillip’s ever-present smile spread wider. “I guess not.”
“Jules picked this outfit out for me.” Gin spun around, letting the knee length miniskirt fly out.
“Gorgeous.” Gin smiled. “And the dress is pretty, too.”
Gin didn’t say anything but climbed into the car glowing over the compliment. The drive to the airport didn’t take long. The airport was a private one in San Rafael, which was a short drive up 580. Phillip used the drive to explain what to expect.
As they walked up to the plane, everything Phillip explained became all too real. It was a medium-sized plane, but it was basically a flying apartment. The interior looked nothing like a commercial plane. There were lounge areas and a big screen TV and a sleeping area in the back behind a wood door with a king-sized bed and another big screen TV.
They would make the trip in two legs. The first would end with a short stop near Philadelphia to refuel, and then they would go straight to Venice. The first leg went by fast for Gin as she listened to Phillip tell his life story. He was a child of wealth, which he saw as a weakness.
“I have no perspective. I just don’t. I remember in college I had a roommate who came from a blue collar family. His dad was like a bank manager or something. I’d constantly be ordering pizza and stuff, and I thought he was the biggest jerk because he would never join me. He’d kind of give me this sneer and walk out to the library or something.
“It wasn’t until second semester that he admitted that he was on a limited budget, and he simply couldn’t afford to split the cost on a constant barrage of delivery food and expensive alcohol. Here’s the thing, Gin—it didn’t even cross my mind that anyone would have trouble affording stuff like that. How horrible is that?”
“That’s not horrible. It’s just that you had a different life experience than him.” The two of them were sitting at a table sharing a bottle of wine as the clouds streaked by. Gin took Philip’s hand. “The fact that you recognized it illustrates that you aren’t a rich asshole.”
Phillip squeezed her hand, and the conversation moved on to funny stories from their youth. By the time the plane started the descent to Philadelphia, Gin was completely enamored with her new boyfriend. He was charming, handsome, and he was just self-aware enough to know that his behavior was constantly being mistaken for his being a rich asshole, when the reality was that he was just innocent.
As the plane bounced on the runway, Gin smiled to herself. I’m dating a billionaire whose social media profile is full of him arm-in-arm with half naked gorgeous women, and I’m calling him innocent. They don’t know him like I do, she thought as she undid her seatbelt and stretched her legs.
It wasn’t much later that the plane was cruising over the Atlantic. Phillip was looking in a cabinet in the kitchen area, while Gin relaxed in a chair. She had lost count of how many glasses of wine she had, but she didn’t mind. Getting a little tipsy while flying to Venice in a private plane almost sounded like a requirement.
“Ah, I knew we had some!” Phillip turned around and had a box of microwave popcorn in his hand. “Want to have an old-fashioned home movie night only on a plane?” He had a mischievous smile on his face.
“Oh, that sounds awesome. What movies do you have?”
“How about The Lost Ring?”
“That was just released!” Gin’s eyes went wide. The movie was a romantic comedy that had been released the week before and was still a box office smash.
Phillip shrugged. “I know people.” He opened the microwave and put the popcorn in. “Gin. I’m going to ask you something, but I don’t want you to get the wrong idea. I just want you to know that this is all in a sense of fun and not some kind of lame maneuver.”
“What the heck are you talking about?”
“Why don’t we change into pajamas, toss a huge bunch of pillows on the back of the bed, have a huge bowl of popcorn between us, and just watch the movie in bed?”
<
br /> Gin almost laughed. Phillip looked almost sheepish, as if he wasn’t sure if she would believe him or not but he really hoped she did.
“Sure. That sounds fun. I’ll get the bed ready.” She walked into the rear cabin and opened her suitcase. For a moment she considered wearing the see-through lingerie and climbing under the covers in them as a surprise for Phillip, but that seemed too far too fast. Although she was still uncertain what was too far and what was too fast.
There was a knock on the door. “One moment!” She had silk pajamas that she quickly changed into. She didn’t bother wearing panties or a bra. The pajamas covered everything, and they felt luxurious against her skin. Her nipples were noticeably hard as they were caressed by the silky material, and Phillip would obviously notice, but Gin didn’t think that was necessarily a bad thing.
“Come in!” Phillip entered with a huge bowl of popcorn in his hand. He had barely crossed the threshold when he just stopped and stared at Gin.
“God, you are so gorgeous.”
Gin ignored him and walked over. She grabbed a few pieces of popcorn and walked through the door. “I’ll wait outside while you get into your pajamas.” He nodded, but she could see his eyes devouring her body.
A few minutes later, the door opened, and Phillip stood in front of her in nothing but a pair of sweatpants, tied at his waist. It was Gin’s turn to take in his body. He had that smooth lean look that she adored. He didn’t have an athlete’s body, but it was tight without being skinny.
“Sorry, I considered wearing this flannel thing, but I just can’t be dishonest with you.” Phillip motioned his hand from the top of his body down to his legs. “This is what I’m most comfortable sleeping in.”
“No, no, it’s perfect.” Gin climbed into the bed, doing her best not to stare at Phillip’s sweat pants to assess what kind of bulge was underneath. As Phillip walked over to the other side of the bed, she added. “I want you to be comfortable. Hell, I’m not wearing any underwear.”
Gin heart beat fast. Holy fuck. Did I just say that? She pulled the covers up to her chin, looking away to hide her embarrassment. Or was it uncertainty? To his credit, Phillip didn’t say anything.
The bed was divine, and the pile of pillows were incredibly comfortable as Phillip dimmed the lights and turned the movie on. “There’s a Pepsi on the nightstand.”
“Oh, thank you,” Gin replied as she took a handful of popcorn.
The movie was incredibly romantic, and right at the moment that the protagonist reconciles with his girlfriend, Gin wanted to hold Phillip’s hand. She didn’t even think much about it. It just felt right. She grabbed the mostly empty popcorn bowl, moved it out of the way, and slid over next to Phillip. She took his hand, and they intertwined their fingers as they continued to watch the film.
As the inevitable tragic twist in the movie arrived, Gin got teary-eyed and pulled herself up next to Phillip and lay her head on his chest. He put his arm around her shoulders and stroked her hair. She rested her knee on his thigh while they watched the final part of the film.
The romantic end of the film took place with a long kiss in Central Park with strangers all around the couple cheering. As the credits rolled, Gin ran her hand across Phillip’s bare chest. Everything felt so magical. She was in the arms of this alpha male guy who was also romantic and stupidly rich. Innocently rich, even. They were in a plane heading to Venice, and her fingers were caressing his bare chest.
It was, without a doubt, even more romantic than the movie they had just watched. Gin ran her hand down Phillip’s lean stomach and felt him take a quick surprise breath, and at that moment she knew what she wanted to do.
She kept moving her hand down and slid it under his sweatpants. She took a deep breath as she felt his smooth skin and then his half erect cock. I so badly want to do this for him. He clearly has no expectations. In fact he’s practically innocent. As she wrapped her fingers around Phillip’s cock, the thoughts justifying what she was doing disappeared, and the desire to just do it consumed her.
Turning her head, she kissed Phillip’s chest and then she licked his left nipple. She began a trail with her tongue down his chest. He had used some kind of body wash and smelled of a mix of cinnamon and other spices. She licked and kissed his skin as she worked her way down. She pulled the string of his sweatpants and tugged them down with her left hand.
Phillip’s cock was harder but still not stiff, and that made Gin excited. She loved the idea of taking this man who obviously had no expectations of an erotic night and then bringing him to ecstasy. She kissed Phillip’s cock on its head and slid her lips down the shaft and licked his balls, which were also smooth. She sucked on his balls and then ran her tongue back up the shaft. He was getting harder, and she badly wanted to feel that happen in her mouth, so she wrapped her lips around him and pushed his cock back into her mouth.
She stroked his cock with her hand while she sucked on it. He took no time at all to get really hard, and she loved how as he got harder she had to pull back as he filled her mouth. He was average size, which was perfect for a blowjob.
Sucking on the head of Phillip’s cock, she stroked its shaft with her left hand. She would occasionally lay her cheek on his abdomen, and part of the thrill was feeling Phillip’s muscles tense as she would lick one spot or suck another one.
Phillip’s hand slid up along Gin’s leg and between her legs. She looked back at him. “No. Just enjoy what I’m doing. This is for you.” Phillip’s hand dropped to his side, and Gin took him in her mouth again.
She stroked his cock and then caressed his balls as she moved her head up and down. She could feel him tense as she slid her head up and down his cock, so she went faster. As she paused to run her tongue around the head as she stroked him, Phillip started to tense. “Oh, that feels so good. I’m going to come.”
With her lips wrapped around his cock as she stroked him, Gin could feel it start to throb. Phillip moaned, and without warning his hot cum shot into her mouth. She quickly swallowed it and continued to suck as more cum shot out. Sucking and swallowing, Gin didn’t stop until Phillip was completely done.
She kissed the head of his cock one last time and then pulled up his sweat pants. She kissed his stomach and then brought her head up and lay it back on Phillip’s chest. He ran his fingers through her hair. “You are amazing,” he whispered. “Thank you.”
“No. Thank you, Phillip. This is magical.”
They fell asleep next to each other on a king-sized bed thirty-thousand feet above the ocean. They didn’t wake until the pilot announced that they were preparing to descend.
They had arrived at Venice.
chapter eight
Phillip crawled out of bed and immediately pulled down his sweatpants. Gin stared at his cock, which was half erect. She loved that he was completely shaved, something she had only experienced a few times. It made him look so clean and, well, fuckable was the only word that came to mind.
Not paying attention to Gin, Phillip grabbed briefs and started to get dressed. He glanced over at her. “Get up, sleepyhead.” He smiled, which made her melt all over again.
She slid out of bed and was suddenly self-conscious. She wasn’t sure she was ready to have Phillip see her completely naked. The ridiculousness of her thoughts paralyzed her. I just gave him a blowjob, and I’m nervous about him seeing me naked? Gin, you are a complete idiot.
She had been naked on beaches, topless at Mardi Gras, slept with lots of guys, and was pretty much completely comfortable with her naked body, but the stakes just seemed higher, and that made her nervous. To make matters worse, Phillip had been so damn nice since they had gotten together at the Billionaires Club. His obnoxiousness at the Orion was a distant memory. Philip interrupted Gin’s thoughts. “Did you leave a suitcase up front? Want me to get it?”
“No. Sorry, I guess I’m just waking up.” Gin crawled out of bed and pulled her top over her head and set it on the bed, only to see Phillip staring at her. She had s
een plenty of guys stare at her tits, and Phillip’s response was so typical that it actually set her at ease.
Gin froze after she slid her fingers under her pajama bottoms. It suddenly struck her that she wasn’t shaved like Phillip was. Was that his thing? She had a small patch, but it wasn’t even a landing strip, let alone shaved. Would he hate it?
She hated her indecision, so she just pulled her bottoms down and tried to ignore Phillip. She turned and started to gather her underwear and clothes from her suitcase. She glanced up for a moment, and Phillip was staring at her naked body. He smiled as he caught her eye.
“That’s exactly what I was picturing under that dress you had painted on at the Orion.” He winked, and Gin forced a smile, turning her attention back to getting dressed. “Gin.” She jerked her head over and looked at him. He looked at her face and then looked her naked body up and down again. “You are gorgeous.”
She whispered a “thank you” as she pulled her panties on and did her best to put her bra on without looking awkward. She finally relaxed when she was dressed. She had a tight top that hugged her body down to her waist which led to a medium-length flowing miniskirt. She remembered Jules whistling at it, saying it was perfect for a walk around Venice—it showed off her figure, while making her look taller.
Phillip was wearing black jeans, a loose white shirt, and black leather loafers. He looked thoroughly European, and Gin laughed.
“What’s so funny?” Phillip asked as he buckled himself in for the landing.
“You look like a native Italian, while I look like a tourist.”
“A beautiful tourist.”
Gin smiled and just enjoyed the moment as the fasten seatbelt light came on.
In the Billionaires Club Page 4