I was so happy to be going somewhere with Jim again—and not just because I got to get away from my family either. That just made it even better. As soon as his driver started taking us toward the airport, I reached down and tried to take his cock out of his pants to suck it. He didn’t have to ask or anything. It was kind of just a tradition, but I was surprised when he stopped me.
“Not now, little lady, save it for the airplane,” he pushed me up, but kept his hand around my shoulder.
“What? We can’t do anything on the plane!”
“We can if we fly private!” Jim answered. “We’re flying in a private jet.”
“Really!?” I said excitedly. We had flown on one to the Bahamas, but that plane was really small and wasn’t very exciting. I hoped this one would be better…
“Yep, so we can do whatever we want on our way to New York,” Jim told me.
“We’re going to New York?” I was really excited.
“Yep, won’t be there too long, though,” Jim answered. “I just have a little business for you there and then we’re heading to the Netherlands.”
“Where’s that? I asked. He pulled out his phone and showed me where it is on a map. I was excited and asked him more questions, but mostly he told me I’d find out when we got there. He said we were going to Spain and Italy, too.
I snuggled up to Jim on our way to the airport. That day we went to a different airport than usual. Jim said it was a private airport. The plane we flew on was smaller than a normal airplane, but it we had more room since it wad just two of us and it was really nice inside. There were four seats and then a sofa behind them.
“Do you own this plane?” I asked when Jim was showing me around.
“I own the company,” he answered. “I wanted a private jet, but instead of just buying one, I bought a company so I could start renting them out. So I actually own 7 airplanes. I’ve arranged for us to fly on one of the bigger ones when we fly to Europe.”
“Cool,” I said as Jim motioned for me to sit. I took one of the chairs by the a window and Jim sat next to me.
Jim’s driver loaded our bags onto the airplane. I had only ever seen him from the back seat of Jim’s car, so I never got a good look at him before. But he was really big—not fat, just tall and muscular. But he looked a little older than Jim. I was surprised when he got on the airplane with us.
“Is he coming with us?” I asked Jim.
“Who Terry? He is this time!” Jim answered. “Terry isn’t just my driver, he does a lot of things for me. I will need him for a few things when we’re in Europe.” The pilot and co-pilot greeted us and we took off not long after that. I watched Houston get smaller and smaller as we flew higher.
“Are you a billionaire?” I asked Jim after we’d been flying for a little while.
Jim laughed, “Actually, little lady, you know that first trip we took together, you helped me buy Edward’s company?”
“Yeah…” I remembered having sex with Edward at the fancy golf club he owned.
“That was the deal that made me a billionaire,” he told me. “My company went up in value 30% since you were able to make it happen.”
“So. . .I made you a billionaire?”
“You sure did,” that’s when he unbuckled my seatbelt and pulled me into his lap. His hand went up my t-shirt and he felt my chest. A minute later he took my shirt off and dropped it on the floor of the airplane.
When he started kissing my chest, I looked over at Terry. He was reading a newspaper and glanced up at me. It made me feel uncomfortable when we locked eyes. I looked away and he started reading again.
Jim stuck his hand down my pants and inside my underwear. He took them both off too sk I was completely naked in his lap. The. I helped him unto his pants and lifted his shirt off.
Once we were both naked, he pulled me in and kissed me some more. It felt so nice to have his naked body rubbing against me again. I put my legs on either side of him and felt his cock push into me.
I moved my hips and Jim’s hands grabbed me. We made out, too while he touched me all over. It felt nice to have a man’s cock that I actually wanted inside my kitty for a change. I hugged his neck and didn’t stop kissing him while I felt his body moving.
“You’re noisy today, Naomi,” Jim giggled. I didn’t even realize that I had been making little moaning noises until he said it. I giggled, too and started moving my hips faster.
I ran my fingers through Jim’s hair when I felt myself start to cum. Then after a little longer, he started making noises, too when he shot his stuff into my kitty. When it was over, I relaxed on top of him and enjoyed feeling him close to me.
His thingy got smaller and fell out of me as we sat there. I had missed having his arms around me and played with his chest hair while he held me.
“I missed you a lot,” I said, snuggling him. He hummed and held my head to his chest. Then I remembered Terry sitting near the back of the plane…
“Should I have sex with him, too?” I looked up at Jim and asked.
“No, little lady,” Jim smiled. “Terry doesn’t like kids.
“Oh…” I kissed Jim’s chest and kept relaxing in his lap. He started softly massaging my head and it felt really nice.
“There’s a man in New York I need you to have sex with, though,” I watched the clouds while Jim talked. “He’s an important judge that does a lot of favors for me. So every once in a while I go out of my way to do special favors for him.”
“You send him girls to have sex with?” I asked, remembering what Hannah’s mom told me.
Jim laughed, “Not always, usually he’s happy to accept cash, but this time he specifically requested a girl your age.”
“Oh—okay,” I answered, still looking at the coulds. “You know, since I made you a billionaire…”
“Yes?”
“I don’t know, I just…” I didn’t know what I was trying to say, but I lifted my head up. “You buy me lots of stuff, but... I mean, you said you were going to teach me business stuff, but if I have to go—.” I was trying to figure out exactly how to word it.
“It’s not fair if that I have to do all this stuff for you just to make you rich!” I blurted out. I was worried he’d be mad, but he laughed.
“I like a good negotiator,” He answered. “What do you want?” I thought about it for a minute. Then I remembered when Jim told me he owned a percentage of a company…
“In Chicago you told me that you owned 25% of the company I helped you with,” I was still thinking… “Can I own part of a company, too?”
“Well, you’re still a kid so it’s a little complicated,” Jim answered. “It’s a lot more trouble than it’s worth.”
“Oh…” but that didn’t make much sense. “But I make you a lot of money, so it’s not fair that I just get a few presents while you’re making millions of dollars,” It was scary talking like that, but was also kind of fun.
“Sure, but if I have to give you a percentage of my deals, what’s to stop me from finding a different girl who I don’t have to pay?” Jim countered.
“I don’t know. . .but I’m smart,” I said. “And you’re teaching me stuff so I can do better…”
“Sure, but my advice isn’t free,” Jim said. “Lots of people would love to have me as their mentor—pay me a lot to do it—but you get to learn from me all the time and all you have to do in return is fuck who I tell you to—and fuck me, of course. There are a lot of already somewhat successful people who would take that deal.”
“What if—“ I tried to think, but I was stuck and didn’t know what to say next.
“Listen, little lady,” Jim spoke up before I could say anything else. “You’re intelligent, beautiful, and really quite cute. And one day you might become an excellent negotiator. But I do this for a living and compete with some of the best in the world. So here’s my counter—If you want to be difficult, I can go into the cockpit right now and have this plane turned around. Then I can drop you back off at your house with that disgusting family of yours and bring Hannah with me instead. Or you can just accept the fact you’re a little eight year old slut that has the privilege of coming with me and enjoying all the toys, trinkets, dresses, and sex that I think you deserve.”
“Okay, you win,” I sighed and put my head back on his chest.
“Hey, I’m proud of you for trying,” Jim massaged my head again. “You’re really hot when you try to take control like that.” Even though we just had sex, I felt his cock rubbing against my leg. So I dropped down in front of his seat and stuck it in my mouth.
I felt the rumble of the airplane engine as I knelt on the floor, moving my head on his cock. He kept massaging my head and I looked up at him while I kept going. It took a little longer to make him squirt this time, but eventually I felt his cock twitching and his goo started filling my mouth.
After I swallowed his cum, Jim told Terry to heat up some food he’d had on the plane because I needed to actually eat something. His cum didn’t count. It was going to be late when we landed and Jim told me I had to go to the judges house right from the airport.
I went to the bathroom in the back of the airplane to get cleaned up, I washed Jim’s goo out of my kitty and cleaned some of it off my cheek, too. But my hair was a mess and I realized I hadn’t brushed it since early that morning.
“Hey, can I get my hairbrush out of my bag?” I opened the bathroom to ask.
“Here, just use this!” Terry handed me a fork since he was getting my food ready nearby. We all laughed and I took it—just like the little mermaid. Once I got my hair looking okay, I walked back out of the bathroom and got dressed again before I ate
As soon as we landed, Jim said Terry was going to drive me to the judges house. I wanted Jim to come with me because being alone with Terry made me feel uncomfortable. But he wouldn’t come. Jim said he was going to go check into a hotel and that he’d see me tomorrow.
Jim had two cars waiting for us at the airport and Terry put our luggage in one of them. Jim told me I wouldn’t need any of my stuff for the night, which did make sense. So I said goodbye and Terry opened the back door of the second car for me.
“Where are we?” I asked, Terry when we started driving, it was already dark outside. I expected to see lots of big skyscrapers, but I didn’t see any.
“We’re in North Hampton,” Terry answered.
“The judge lives here?” I asked. I saw a few fancy houses as we drove
“He lives nearby—we’re headed to Shelter Island,” Terry spoke in a low tone
“Oh…” I didn’t know where my family went when we visited New York since I was too little to remember. But I doubt they took me to the Hamptons.
“What do you do for Jim?” I asked after we'd been driving for a while. Jim had mentioned he did a lot more than just drive him.
“I work for him.”
“Duh!” I laughed. “But what do you actually do?”
“I drive little brats like you around.”
“Hey, I’m not a brat!” I scolded him.
“If that were true, you’d stop asking so many fucking questions then!”
“Okay. . .are we almost there yet?”
“Another 20 minutes or so.” We both stopped talking for a little bit and it going really quiet.
“Do you like working for Jim?” I decided to ask about his job again right when I noticed it was starting to rain.
“Do you like working for him?” Terry replied.
“Okay, I’ll stop,” I said finally. “I think you’re really funny.”
“Good for you, kid,” Terry answered, taking a long pause before he kept talking. “You know, you’re not the most annoying kid Jim’s had around.”
That’s when I realized I’d been asking the wrong questions the whole time! “Do you drive kids a lot?”
“Yes,” he said.
“How many kids have you driven?” I wondered.
“I don’t know,” Terry replied. “I’ve been working for Jim a long time. So he trusts me to take care of things. But the less you know, the better.”
“Why?” I asked.
“Seriously, Naomi, shut the fuck up,” Terry said it in a friendly way, but I still felt like I should listen to him. I looked out the window for the rest of the drive and didn’t say a word.
It started raining harder before we stopped in front of a big house where I assumed the judge lived. It wasn’t as big as Hannah’s house, but definitely bigger than mine.
“Okay, go ring the bell, I’ll stay here to make sure you get in okay,” Terry said. “Then I’ll be back around 11 tomorrow morning to pick you up.”
“Okay,” I opened the door, feeling nervous. Trying not to get too wet, I ran up to the porch of the house and found the button for the doorbell. Moments later, the door swung open.
Inside the house, there was an older man with a grey mustache who looked down at me and smiled, “Ah, you must be Naomi!”
“Hi,” I answered and I turned around to wave to Terry. But he was already driving away. Feeling nervous, I turned back and stepped into the Judge’s house—ready for whatever he wanted to do with me.