I remembered James from when I was a kid. He had moved into my neighborhood when I was around seven years old. My mom said that he was only thirty, but had bought a house on the street that cost something like a million dollars. There were rumors that he had made his first million by the time he was twenty-one, but no one really knew for sure.
The area in the canyon that I lived in was pretty exclusive. My dad had invented some part for jet engines that was now in virtually every single one produced. We were not strangers to wealthy people, but James was different. He was half kid, half adult, always giving stuff to the local kids, joking around with us and playing with what could only be described as “big boy toys.” He had two ATVs, five cars, and this huge contraption in back of his house like a bungee jump.
By the time I was thirteen he had moved away, and my dad said that it was because he had made millions more and would probably be buying a chalet in Switzerland or a tropical island somewhere. All the kids in my neighborhood started calling him James Bond because he was so mysterious.
I grew up, went to university, and never really thought much about him again until I saw a news article. I was in my first year at Stanford when there was a piece about how he had revolutionized some kind of water filtration system—another invention that made him tons of money. The article said that because it was easy and cheap enough to use in developing nations, he stood to make billions. I showed my friends and told them that I knew the guy, but no one believed me.
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Lelo Ora 2
The World’s Most Sophisticated Oral Sex Simulator
That would have been the end of it had I not been in San Francisco that weekend. Two of my good friends at college convinced me that we needed a getaway from school/ They thought we should go to the city and all spurge and share a room in a luxury hotel. It wasn’t an uncommon thing for us to do, especially before exams. It was a good way to relax and let off steam.
So that weekend in April, Danielle, Laura, and I booked a big room at the Four Seasons. When we split it three ways, it was still a bit much for us, but staying in such a nice place for a weekend really cleared our mind. And besides, the three of us were all cute and flirty enough to get drinks—and maybe even dinner—bought for us at the hotel bar. If not, there were always more affordable local places.
The three of us were quiet a trio. Danielle, with her wild blonde hair and big breasts, was the most talkative of all of us. She had these huge green eyes that could make almost anyone melt and her smile should have been on T.V.
Laura was a raven-haired beauty that was taller than a lot of guys. She had some kind of Slavic background, giving her high, elegant cheekbones and a rather naughty look. Out of the three of us, she actually did have the most experience with guys, and she would tell us many dirty stories.
I myself had the “young” look going for me, with long, curly brown hair, big brown eyes, and just enough baby fat in my cheeks that I still got asked for my ID nearly everywhere we went. But I had the most perfect ass and breasts from doing gymnastics for six years as a kid, and later yoga and pilates.
The three of us sat at the bar of the Four Seasons on a Friday, all dressed to impress. We had been there for less than ten minutes, when a bottle of champagne arrived.
“Compliments of the gentleman over there, ladies,” the bartender said. I knew that Danielle already had her sights set on him. He was very fit and gorgeous.
“Told you, Cheryl. I knew that guy looked like money when we walked in,” Laura said to me.
I looked over my shoulder and there he was: James Bond, right out of my past.
“Tell him,” I said to the hunky bartender. “That we would love to accept it if we can come and sit with him.”
I don’t think that he had recognized me. After all, the last time we saw each other, I was an awkward thirteen-year-old just sprouting breasts. And even then, it wasn’t like we were good friends, I was just some kid that lived next door. I did remember him watching me do gymnastic moves in my backyard though, and cheering me on when I managed to get a new one right.
“Hello, ladies,” he said as we approached the table. “My name is James. Won’t you join me?”
We all sat down in the big booth while the waiter opened the champagne. It was Krug, which I had never tasted, but I knew that it cost hundreds of dollars for just one bottle.
“And what are your names?” he asked, looking at me first.
I didn’t speak, but only smiled. I wanted my friends to go first. I had told them about this guy when I had found the article, but they had no idea that it was him.
“Danielle,” my wild blonde friend said, holding out her hand and pushing her chest forward to accentuate her breasts. He shook her hand and then kissed it like she was some kind of princess. Danielle giggled.
“I’m Laura,” my other friend said. “Princess of the lands east of Greece.” She loved using that line, and she could have actually been one too. He kissed her hand also.
“I’m Cheryl,” I said finally. “Former neighbor of yours back in Mill Valley.”
He didn’t take my outstretched hand, but instead just sat there with his mouth open.
“Little Cheryl from Mill Valley? Oh my god, you have grown into such a… a woman!” Then he stood up and gave me a huge hug.
“I often wondered what became of you,” he went on. “That would have been what, like, seven or eight years ago?”
“Six,” I said. “And yes, I have grown up. I am at Stanford now. Not much like the thirteen-year-old that you knew back then.”
“So, what, you’re nineteen now? Should you even be drinking?”
I laughed out loud and so did my friends. It was cute that he felt concerned that we were not legally old enough to drink.
“Nineteen is old enough to do just about anything but drink. How stupid is that?” said Danielle. She was probably feeling left out of the conversation.
“Good point,” James said, sitting down so as to include everyone else again. But he could not take his eyes off of me.
We sat with him and sipped the most amazing champagne that I had ever tasted. He asked us about school, what we were doing in the city, and what we enjoyed doing for fun. He kept coming back to me, asking about the old neighborhood, my parents, and my little sister. I had never realized that he had actually paid that much attention to anyone in our community. He was always just the rich guy up the street.
“So, are you girls staying at the hotel?” he asked “Or are you just trawling the bar for unsuspecting travelers?” He said it in a good natured way, devoid of any untoward implications.
“We… umm… are sharing a room. We do this sometimes to get away from the pressure of school,” Laura said.
“It’s our little fantasy getaway,” I added. “It is such an amazing hotel.” I must have sounded young and inexperienced, but he smiled and touched my arm.
“Sharing a room?” he said. “How long are you staying for?”
“Just the weekend,” Danielle answered. “We have exams next week.”
“Well, you should all have your own rooms, then,” he said. Then he held up his hand for the waiter.
Before I even got a grasp of what was happening, he had booked two more rooms and told the waiter to take care of it all. He said he would bring us room keys in a moment.
“But… you can’t do that. These rooms cost a fortune!” Laura said, and then it occurred to her. “You don’t think that we’re going to…”
“Relax, Lady Laura, princess of all the lands east of Greece. I don’t expect anything. I’m just being nice. I haven’t seen my lovely friend Cheryl in years. And besides, a couple of nights in a room here cost less than I make in five minutes.”
All of us were in shock, except for him, of course. He was the picture of calm, cool, and collected. I took a closer look at him. He was probably about forty-two or so now, with just a tiny bit of grey at his temples, but with a full head of dark, wavy hair. His suit looked like it would have cost a grand, at least. He fit into the surroundings as if he owned the place.
“Okay, but… are you sure? I mean…” Laura was stuttering, searching for the right words.
“We gratefully accept,” I said, finishing her sentence for her.
“Would you all join me for dinner tonight? My treat. But you’ll all have to go to the shop in the mezzanine and get suitable dresses. Just put it on James Hawthorn’s tab. They can ring me if they need to.”
Danielle’s mouth was opening and closing, a bit like a fish, as she struggled for something to say. Laura was blushing because she had assumed the worst, only to be surprised by the depths of James’ generosity. I was the only one semi-composed.
“What time shall we meet you, James?” I asked.
“How about eight, at La Rincón? It’s easy to find, just ask at reception.”
The porter had come and handed us two keys. It was decided that Laura would keep the room we had and Danielle and I would move into the two new ones. James asked us our room numbers and then stood up to sign for the bill.
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Lelo Ora 2
The World’s Most Sophisticated Oral Sex Simulator
“See you at eight, ladies” he said, and then he was gone. We all sat in stunned silence.
“Holy shit, Cheryl. You really did know that guy! He’s worth, like, billions!” Danielle said. Then she grinned wickedly. “Let’s go buy dresses!”
We got up, barely even believing that it was all happening, and walked out to where the mezzanine shops were. There were Rolex stores, perfume shops, and a fantastic place with designer dresses. We walked in, very self-conscious that we could never afford one of these dresses on our own. Even looking at one was out of our price range.
“Umm… James said…I mean James Hawthorn… he said…” I was nervous all of a sudden.
“Very good, ladies,” said the woman in the shop in a clipped English accent. “James has just stopped by and said that you would be coming. Anything in particular? Do you need some help?”
I knew all the designer’s names and I had seen them on actresses at awards shows, but I had never even touched one before. We spread out, looking at everything, mouths agape like three kids in a candy store.
By the time we had finished, we figured that we had spent over $3000 of his money. All three of us looked like famous movie stars, and we insisted on wearing them out, something that I gathered by the saleslady’s expression was not usually done.
“My god, Cheryl. You are a vision of pure beauty,” James said to me when we arrived at dinner. He complimented the others too, but in no way as strongly as me.
Dinner was a lavish affair, with many different courses and with a different wine served with each dish. Initially we were all quite stunned, but as the evening wore on, we relaxed and became very talkative.
James was the perfect host, listening to everything that we said with genuine interest and not laughing at us if we didn’t understand something. Although we considered ourselves quite grown up, it was hard not to feel like the very young women that we really were, barely out of high school.
“What would you all like to do now?” James asked when dinner was over. I was still eating my dessert, a piece of red velvet cake with candied rose petals.
“Let’s do something really different,” Danielle suggested. It wasn’t very specific.
“Do any of you girls have a fear of heights?” James asked.
I did, a little, but wasn’t about to say anything. It wasn’t that kind of morbid fear, just the kind where your tummy tingles when you look out over an open space below you.
After we had an after-dinner cocktail, James took us to the elevator to go upstairs. At first I thought that he was taking us to his room, but then the elevator opened on the roof. There in front of us was a helicopter.
“You want us to go in that?” Laura said. Now she was the one who sounded afraid.
“It’s perfectly safe, and if you haven’t seen the city from that air at night, you don’t know what you’re missing,” James responded.
We finally all got in, convincing Laura that we wouldn’t go if she didn’t, and that made her feel like she had to. It wasn’t as flashy or glamorous as I thought it would be. We all had to wear headphones so that we could talk. But once we got up in the air, it was amazing.
We flew out over the bay, then out to sea and back in toward the Golden Gate Bridge. I sat close to James in the front. I hadn’t even realized that I was grabbing onto his leg as we flew. My stomach full of butterflies as we seemed to float on air.
After we landed, I was still holding on tight. When the engine turned off, he leaned over, kissed my cheek, and whispered in my ear.
“I think you can relax now,” he said, gently prying my hands from his legs.
We went back inside the hotel for one more drink at the bar. James thanked us for spending time with him and suggested that we all get some rest. If we wanted to, we could do something with him on Saturday, too. He had one meeting, but that wouldn’t be a problem.
We all went to our own rooms and I flopped down on my bed. The excitement of the night had been almost overwhelming.
Then my room phone rang. Only my friends and James knew where I was. I secretly hoped that it was him.
“That was crazy, wasn’t it?” said Danielle from the other end. “What an amazing guy. Cute, too. Do you think he would fuck me if I offered it to him?”
“God, Danielle, you are so crass,” I said and laughed. “But yeah, probably. I don’t know. He definitely is cute though, isn’t he?”
“Yeah, and worth like a gazillion trillion dollars, too. Can you believe this dress?”
We laughed and talked about how crazy our trip to the city had been. What had started as a little innocent getaway for three college freshmen had turned into a fantasy trip complete with an attractive billionaire.
There was a beep on my line, indicating another call. I guessed it was Laura.
“Hiya, Spunky,” I said, using a pet name that we called each other.
“Well, you’re very spunky too,” James said to me. I sat bolt upright, a tiny bit embarrassed.
“Oh. Sorry, James, I didn’t know… I mean, thank you… I mean, I thought you were Laura.”
“It’s fine, Cheryl, relax. I was just wondering if you would like to maybe spend a little time talking. We didn’t have much alone time, and it would be nice to catch up. That is, unless you’re tired.”
I was not the slightest bit tired. After the events of the evening, I wondered if I would ever even sleep again. I was more excited than I’d be on any Christmas Eve I could remember. I told him so, too. He laughed and invited me up to his room. I agreed and went back to the other line to tell Danielle.
“Are you gonna fuck him? I would. If you aren’t going to, I will,” she said, and we both laughed. Neither of us were super experienced, but we weren’t virgins, either. I had no plans to have sex with him and I told her so, but I didn’t discount that I might.
“He’s more than twenty years older than me, Danielle. I highly doubt that he’ll want me. He can have anyone.”
I hung up and went up to his penthouse suite, but not before washing up a little, just in case. I had no idea if that was his plan, but he fascinated me enough to the point where I would probably just say yes if he asked. No one had ever treated me—or my friends, for that matter—like this before.
His penthouse was huge. From what I could see, there were two bedrooms, a little kitchenette, and a big, wide open living room that extended out to a terrace. It looked more like a luxury apartment than a hotel room.
“Wow,” I breathed, clearly in awe. “I wish I lived here.”
“No you don’t,” James said. “I practically live here, and believe me, having a home is way better.”
He explained that for almost the last six months, he had been in the city because it was easier than coming back every week. He actually did have a home—three of them, in fact. One was in the British Virgin Islands, another was a suite In New York City, and the last was a house in London. All were places that I had wanted to go, but had never been.
“Perhaps I will take you sometime, if you really want to go,” he said.
We were sitting on the terrace overlooking the lights twinkling across the bay. We got to talking about Mill Valley and how life had been back there. He told me that he sometimes wished he’d been a teenager when he lived there so that he could have chased after me. I giggled at the thought of it.
“It’s not too late,” I said, knowing full well what I was offering. “I’m still technically a teenager.”
“Cheryl,” he said looking at me seriously. “I always get what I want, and my tastes, well… let’s just say that they are on par with my… lifestyle.”
“Meaning?” I asked, bemused.
“Meaning if that’s something that you want to embark on, be sure about it.”
He made it sound both exciting and dangerous at the same time. But it wasn’t like I was an innocent little virgin. I had slept with a few boys, and one of them was even twenty-eight, so I had some experience, though admittedly not a lot.
“I’m a big girl,” I said almost defiantly “I can handle it.”
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Lelo Ora 2
The World’s Most Sophisticated Oral Sex Simulator
“Right, then. If you want to try a little something, you can see if you like what I’m into.”
I put my hands down on my $1000 dress, feeling the smoothness of the fabric. I considered what it would be like to hang out with James. I still had to finish my school year anyway, so it wasn’t like I would be jetting off to an island somewhere. He was attractive and sexy, and the fact that he had tons of money was just a bonus.
“What do you want to try?” I asked him.
“Take off your panties and kneel on the bed. Right up on the edge.”
I did as he asked, the silken fabric of the dress brushing up against my pussy lips, already swollen a little from anticipation. He knelt behind me on the floor and pushed my dress up, revealing my wetness. He gently pushed my legs apart until I was completely exposed. He stayed fully clothed.
James softly kissed over my thighs, and then moved his lips to my enlarged labia. He began to lick me and tongue-fuck me, filling me with an indescribable pleasure. I gasped as I came closer to an orgasm with every second. But every time I did, he stopped and kissed my thighs again, teasing me, forcing me away from the edge he’d brought me to. Then he would start again, sometimes using his fingers inside me.
For almost forty-five minutes he did that, bringing me right to the cusp of a massive orgasm and then stopping. He knew just how to suck on my lips and clit, drawing them in and then releasing. My legs started to get sore from being in that position and I told him so, but he would not let me move. The denial of my orgasm was almost painful, and I was at the point where I could not stand it anymore.
“Please make me cum,” I begged, grabbing his head.
“No touching,” he instructed me as he stood up and got one of his ties.
James gently bound my hands behind me. It wasn’t tight, but I couldn’t move them at all. I imagined that tie would have cost him about $200, and he was just knotting it up.
After almost another half an hour of him starting and stopping, I was almost on the edge of tears. It physically hurt. Now I could imagine what those boys meant years ago when they said that I had given them blue balls by not giving them at least a hand job.
“Please, James,” I cried. “I need to cum!”
“Will you earn it?” he asked.
“Anything! Whatever you want. Please!” I was begging, simpering for an orgasm. It was pathetic, but James seemed to like it.
He stood up and unzipped his pants. He didn’t take them off, just pulled out his cock. It must have been seven or eight inches and quite wide—bigger than I was used to. It was all covered in veins and dripping a huge glob of precum. I thought that he was going to finally fuck me.
“Swallow all that you can,” he said.
He grabbed my head and drew it towards his cock. He held his base with his other hand, slapping my face with his shaft a few times and making the precum stick to my cheek. Then he pushed it into my mouth, grabbed a handful of my hair, and began to fuck my face. If any other man had done that to me, I would have gotten so mad, but in this case I was hornier than I had ever been in my life and I welcomed it. He shoved it deep, almost making me gag. I had to breathe as he drew his shaft out.
Then quite suddenly, he was flooding my mouth with copious amounts of warm semen. It was a steady, constant flow. I had never let a boy do that to me before. The taste was tart yet sweet, not at all unpleasant.
As he filled my mouth, he told me to swallow it. I tried to, really, but there was so much that huge amounts trickled out of the sides of my mouth and down onto my new dress. When he had finished, he drew his cock out of my throat and smiled.
“Pretty good job,” he said. “We’ll send the dress to get cleaned.”
Then he reached between my legs, sticking three fingers inside my wet, gaping hole. He moved his hand very rapidly, his fingers pulling forward against my sweet spot. In less than a minute, I was completely overcome with the most intense orgasm that I had ever had in my life.
My entire body shook with uncontrollable spasms. I became so sensitive that I could not stand to be touched at all. And at the same time, I squirted a silky spray of liquid all over the carpet. I thought I had peed myself, but James was delighted.
“Well done, Cheryl, and on your first time, too,” James said, clearly pleased with himself.
I could hardly speak. My mouth still had his cum in it and my body was still trembling. He told me that I had just done what he called “gushing,” “squirting,” or “female ejaculation.” He said that all women could; they just had to be taught how. I was the perfect student. I waited for him to untie my arms, but he didn’t right away.
“I never would have imagined that little Cheryl was capable of being so dirty. Did you like it? Did you enjoy all that cum?”
“Yes,” I said, nodding my head. I did enjoy it, but I wanted him to untie me.
“And you want to try more?” I was staring at his cock dangling in front of me. It had gone soft, but was getting hard again.
“Yes… umm… well…”
“I want you to be sure, Cheryl,” he said taking my face in both of his hands quite tenderly. “I can be very generous, and very dirty also. Are you ready for that?”
“Yes,” I squeaked. His cock was fully hard again. I had never seen a guy do that so quickly.
“Do you like anal sex?” he asked, as if it were an everyday thing.
“I’ve never… I mean…”
“That’s okay. We’ll take it one step at a time,” he assured me.
And then he went from being so tender to spinning me around so that my ass was facing him. With my hands bound behind my back, my face sunk into the bed covers. It was a little uncomfortable. I was terrified that he was going to try and fuck my ass then and there.
But he drove his cock deep into my pussy, each thrust pushing my face into the sheets. The extreme sensitivity I’d experienced earlier had given way to more lust, and I actually found myself pushing back into him. He held my wrists where they were bound with one hand and grabbed my ass forcefully with the other.
“So…. now… you… are… my… slut…” he said, one word coming out in between each deep thrust.
He was doing it again, bringing me to the edge of yet another orgasm. Something about being treated so dirty made it even hornier. I liked it, and found something in myself that I had never known was there.
“I am going to fill you with cum now, and I want you to keep it there all night, do you understand?
“Yes,” I managed, even though I was cumming.
Then he surprised me. He pulled his cock out of my pussy and put the tip just the tiniest bit into my ass. I could feel the flow of his sperm enter me. Jet after jet of goo filled me up. It was warm and wet and it was the dirtiest thing that anyone had ever done.
Then he stepped away from me and picked up his phone, walking to the other room. I slid down on the bed so that I was lying on my tummy. I could hear him talking in the other room. He came back out and untied me and handed me a glass of champagne.
“Get that dress off quickly. They’re bringing up something for you. We need to send this to be cleaned. They’ll return it to you in the morning.”
I did as I was told.
There was a knock at the door not ten minutes later, and James took the package. There was a designer shirt and jeans and a pair of panties. The dress was sent away. I had no idea what happened to my other panties.
James told me to get dressed and get back to my room for some sleep. Tomorrow was going to be a busy day. My friends were more than welcome to come along too. He told me that he understood that I still had school, but that I should be free on weekends. He had plans for me, he said.
He kissed me, very tenderly, which was so at odds with how he had just used me. I could feel his cum dripping into my panties, slowly seeping out of my ass. As convoluted as it may have been, it made me horny again. I asked if I could stay the night.
“Not tonight, Cheryl. I have things to attend to. But please be ready at ten-a.m., and tell your friends too. Wear something for the beach.”
That was it. He walked me to the door, kissed me like a boyfriend would, and then gently pushed me out the door.
I went back to my room, still in a state of shock at what had just happened; at what I had agreed to. I called Danielle, who already suspected something anyway. I didn’t reveal everything of course, just the basics. She was really excited that she and Laura had both been asked along for whatever was planned for the morning. I crawled into bed, wondering what would come next.
I woke up at nine, with room service delivering both a lavish breakfast and my dress. There was a little note in an envelope from James, too. He said that he was looking forward to us spending time together. That it would be more romantic, dirtier, and more exciting than anything that I had experienced in my life.
I secretly couldn’t wait, and even as I washed the dried cum from my ass in the shower, I was ready for more.