“You could always be one of those progressive guys who kept a couple of women,” Robert said jokingly as they headed back to the office.
“Yeah, that would be better.”
“No, Drake I was joking. Trust me. Two women would be way too much to handle on a daily basis. Plus they wouldn’t get along and would always be fighting. It doesn’t work that way.”
“I like it. Maybe two really hot, smart, sexy women. Mmmm yeah that would be perfect. I could take turns with them. Maybe they could take turns with each other. Perfect.”
Robert just rolled his eyes as he stopped walking altogether.
“Drake, that’s a porno film, not real life. You can’t even find one hot, sexy, intelligent woman to keep around. How do you expect to find more than one?”
“Alright. Let’s say I wanted to find just one. We need to figure out the most efficient way to just get this over with. I don’t have time for dating a million women and wasting time.”
“Have Sam help you. She has known you for five years. The two of you could go to one of those fantasy matchmakers or something,” Robert didn’t seem very confident in his plan.
Robert could still remember the time Drake did go to a matchmaker service and he ended up fucking the matchmaker. She was totally into it, but then refused to help set him up with any of her clients. Pretty much she just wanted to keep him for herself.
Drake stood still and stared at the movie poster on the building they were in front of. He had a fantastic idea.
Chapter 4
“I would settle down if I could have women battle over me like in that,” Drake said as he pointed to the latest movie poster.
It depicted a group of people battling to the death as they were held captive on an island. Drake smiled as he thought about how much fun it would be to be held captive on an island with a bunch of beautiful women fighting over him.
“So, would they fight to the death? The last one standing is the one you’d keep?”
The two men laughed as they thought about the outrageous plan. It had to be something most men had pondered. A little fight to the death among hot women. A lot of sex and battles to see who was the best.
“Yeah, why the hell not. I’d love to see some women fighting over me like that. Full on chick fights are hot.”
“Drake, you’re talking craziness,” Robert just brushed him off as the two of them continued toward the office.
“Instead of a battle to the death, I’d like to do a sex battle. Oh fuck yeah. Can you imagine? Stuck on an island and each woman fucking my brains out until I was too exhausted to move. Now that would make a good fucking movie.”
Robert just rolled his eyes as the pair continued into their building and waited for the elevator.
“Maybe you could set some rules up, or give out points based on their sexual abilities.” Robert clearly was just humoring Drake by that point.
“Yes, perfect!”
“No, Drake it isn’t perfect. Woman don’t like to be looked at as a game to win. You’d never get a woman to agree to such a thing.”
“Oh, you underestimate the women that I sleep with,” Drake laughed. “I do think we should keep the killing in our little island game, though. That would make it much more fun.” Drake laughed.
“Yeah, maybe they could be naked too. That would really be hot,” Robert added as he really started to get into the idea.
“Fuck yeah, and have them do some naked competitions. Maybe compete for my affections. Oh, that would be hot.”
“I feel some Jell-O wrestling coming on.”
The two men just laughed and laughed as they continued to plan out their factious sex island that Drake would use to find his perfect woman.
The funny thing was, the more they talked; the more Drake actually wanted to figure out a way to find the woman of his dreams. He was kind of tired of using all his energy to find one night stands. It would be so much more efficient if he had one amazing woman around.
“I’d love to fuck a group of women. Like a full on orgy but with all women who wanted me. God that would be so fucking hot. Let’s find an island and get this party started,” Drake winked at Robert.
“That’s exactly the problem Drake. If you filled an island with the women you sleep with, you would be the one running for the nearest boat. You can’t even be around those women longer than one night.”
Drake had to admit Robert was one hundred percent right. He really couldn’t stand to actually be around most of the women he fucked. But those were the women he was attracted to. He would never settle for a woman who wasn’t smoking hot. The sexual attraction had to be there, it was extremely important to Drake. Sexual attraction did come in many forms, though. A woman didn’t have to look like a model, but she did have to be confident and proud of her body. That meant Drake would fuck a woman of any size, if she had the sexual confidence he liked to see.
“Well it was a fun idea at least...”, Drake said a little dejected as they made their way up to their offices.
“Perhaps you could do something for real though Drake,” Robert suggested.
It wasn’t a totally horrible idea to bring a few women around and see which one Drake could actually stand for longer than a night. Of course, there would be no fighting to the death or anything like that. But they could certainly do something more similar to those wild dating shows that were on television.
“You just got done convincing me it was a stupid idea. Now you like it?” Drake said as he playfully shoved Robert out of the elevator.
“Hear me out. Yes, you could do something like have the women come to your house, maybe spend the week there.”
“Yeah, I could do that. It would be the best way to get to know a group of women and find one that I wanted to keep around. But there’s one problem.” Drake looked at Robert and started to pull on his hair.
“What? Why are you pulling your hair?”
“That many women in one place is sure to cause some serious cat fights.”
Drake pretended to pull on his clothes and scratch Robert. He continued to tug and pull as he pretended to have a cat fight with himself. Robert couldn’t help but laugh as Drake made fun of their planned way of getting Drake, a woman.
“I think it’s a good idea. We should run it past Sam. Obviously we would not have the killing in our little plan. But we could make this work.”
“Oh, no. There is no running this past Sam. We don’t need to, we are doing this Robert. I’ve decided. I need a regular woman and this is the most efficient way of making things happen.”
Drake was a very decisive man. He really didn’t like to sit around and plan things and much preferred to just make his decision and then move forward with things. He also knew that Samantha wouldn’t approve. She already hated how he had one night stands all the time; she surely wouldn’t appreciate his plan to have a bunch of women live with him for a week so he could fuck them and get to know them.
“Well, you’ll need her help in picking the women. We can’t leave it up to you. You’re horrible at it.” Robert shoved Drake back as they stood in the lobby of their floor.
Robert really did think this plan was a good one. Drake needed a woman in his life. All the one night stands weren’t going to get him anywhere in life. All the big executives had women in their lives. Having a woman around softened up the persona of a leader and she was also the perfect partner to attend business meetings and charity events. Drake would love it, Robert just knew it.
But as much as Drake wanted to just plan it all himself, Robert knew he didn’t have time for that and Samantha was going to have to do a lot of the work. They were going to have to figure out a way to convince her it was a good idea. She needed to be on board with the plan before they could get started with it.
Oh, Sam would do anything that Drake asked her to. She was an excellent assistant. It was her job to make Drake’s life easier. Plus, if Drake really wanted something he knew that Sam would back him; she always did. But
getting her on board with the plan would ensure the ultimate success.
“I think she’ll like my plan. Let’s go ask her”, Drake moved quickly down the hall toward Samantha’s desk.
Samantha had returned from her errands early and sat at her desk and watched the two men as they walked toward her. She had to laugh when she saw the childish grin on Drakes' face. He only got that look when he was up to no good. She knew that look very well. It was often the look she saw just before he did something stupid.
Chapter 5
“What are you up to, Drake? I’ve seen that smile before”, Sam said as she met his gaze.
“I have a job for you. It’s going to be a fun one.”
Samantha hated when he said stuff like that. Drake was notorious for the way he went about business and life. Full throttle, non-stop without worry for anyone at all. It made Samantha very nervous. She lived life within the boundaries of rules. Yes, she had fun. She actually had a lot more fun than Drake probably thought she did. But she always lived life by the rules…her own rules. Samantha used logic to make her decisions and hated that Drake always seemed to not stop and use his own logic.
Drake was clearly a very bright man. He ran his business with insight and creativity that Sam envied a lot, but Drake had an extremely difficult time living by the rules. Anyone’s rules.
“Alright Drake, I’ll bite. What would you like me to work on?”
By this time, Robert had also joined them and he was smiling just as broad as Drake was. Samantha was nervous. Robert was normally the level-headed one of the group. He typically could talk Drake out of things. So if Robert also thought this was a fun job, Samantha was certainly interested in hearing more about it.
“I’m going to host a group of women at my house and have a fight to the death for me!” Drake said excitedly.
Sam couldn’t help but laugh out loud at the preposterous idea.
“Oh yeah, a fight to the death?”
“Remember, we decided no death,” Robert added as he and Drake made their way into Drakes office and Samantha followed them.
The three of them sat around the conference table and Drake tried to explain what he wanted Samantha to do.
“Alright. We will have to work out the details, but basically this is what I need. I want you two to find me like five to ten of the most amazing women. I don’t just mean beautiful. I mean sexy, smart, basically the whole package.”
“Oh, because that will be easy to find,” Samantha said as she took notes.
Samantha had learned from working with Drake that she always had to take notes when he got one of his wild ideas. Often he would forget what he said and ask her about it, so she always took notes, it just made it easier on her later when he decided he wanted to do whatever his crazy idea was.
“I believe in you, Sam. Alright so let’s just say you are able to find these women. The two of you will know who I’ll like. Then we will set up some rules and they will come to my house for a week.”
“What will they do while they are at your house for a week?” Sam asked as she kept taking notes.
Sam looked skeptically from Robert to Drake and then back again. The two of them were so excited that it made Sam smile as she waited for Drake to tell her all the details about his plan.
“Fuck me.”
“Oh come on Drake.” Samantha threw her pen across the room. “You’re going to go to all this trouble to find these fantastic women and all you want to do is fuck them?”
“Alright, what do you suggest?”
“If you want the caliber of woman you say you do. They are going to need more from you. You’re going to have to talk to them, have a date with them, and get to know them.”
“Then fuck them?”
“Yes, then fuck them.” Sam smiled as she wrote it all down with the pen she took from Robert.
“He really does need to fuck them, Sam. It’s an important part of knowing if they're a good match.” Robert added.
“I know you guys think I never have sex at all. But believe it or not, I understand the importance of having a fulfilling sex life. I just think Drake has to have some sort of emotional connection with these women. If we are going to do this, we should go all the way. Isn’t that what you always say, Drake?”
Samantha was so right. Drake never did anything halfway. His whole life was spent pushing the envelope, taking things as far as they could go and then going even further. He wouldn’t settle for an employee that was mediocre and he certainly wasn’t going to settle for a full-time girlfriend that was mediocre. Drake needed a woman that had it all.
As much as Drake didn’t want to admit it, he started to get excited about this little adventure that they were planning. Of course, it would be exciting to get to know some gorgeous women, but he was also excited at the idea of finding a woman that might actually be his match. He wasn’t sure she was out there, but the thought of her was exhilarating.
“So when would you like to do your little matchmaking game?”
“Let’s say in one week?” Drake said as he scratched everything off his calendar.
“Drake, seriously? One week? You want me to find you a group of perfect women who can give up their entire schedule for a whole week and you want me to do it in less than seven days?”
“Robert will help you.”
“What? Me? No, no, no I can’t help with this matchmaking game. Someone needs to run the business.”
“Oh you know you want to interview some sexy women, Robert.”
Robert didn’t argue. It was a good excuse to get to hang out with some gorgeous women. He was a 100% faithful husband, but looking certainly wasn’t cheating. And boy did Robert like to look at the women that Drake dated. Drake always had the women that were so beautiful you didn’t even need to ask why Drake fucked them; Robert knew exactly why.
“Are we looking for level ten women with big boobs? Or what are we looking for?” Samantha continued to take notes like the dedicated assistant she was.
“Sam, I want women that will be my equal. I’ll let you pick some nines if necessary. I’ll let you pick any woman you think will give me a run for my money.”
“Any woman?”
“Fuck it. Yes. I love women. I love smart ones, blonde ones, big ones, short ones. You find me a woman who has a sex drive as high as mine and a brain for business I’ll be in heaven.”
“I think we should find some really kinky women. Drake isn’t going to be happy with plain woman.” Robert added as he sat back in his chair and thought about the women they should find.
“I don’t know, Robert. A nice sweet girl with an MBA might work pretty well if she was open to experimentation.”
“I like how you guys think. Go get to it. I’d like to have them at my house by Saturday.”
“You want me to get started now?”
“Yes Sam, now. You only have less than a week to bring me a group of women that would be perfect for me.”
“Are you still going out with Rose tonight?”
“Sure, what the hell. I’ll go out with her.”
“Why don’t you try actually getting to know her? Practice for your week long matchmaking game.”
Drake liked that idea. It would be fun to pretend like Rose was one of the contestants and Drake could practice going on a real date and trying to get to know her. He really didn’t do that very often in a real sense, probably because he didn’t actually go on dates. Most of the women he met were simply interested in nailing him and then bragging to their friends. After the sex, then they started to contemplate what it would be like to official date Drake.
Sure he pretended to get to know women so he could get enough information to get them back to his place. But he didn’t often actually get to know them. It would be a good night to practice that.
“I’m game for this date tonight. I’m going to totally knock her socks off. You just wait and see.”
“I really hope you two hit it off, Drake. She’s a really nice girl
.”
Chapter 6
Drake arrived at Giorgio’s Italian Restaurant totally prepared to work on his real dating skills. He was more determined than ever to show this girl that he could have a conversation and not just sleep with her.
Secretly Drake hoped that Rose was ugly so he could concentrate on his questioning skills and his listening skills and not have to worry about lusting after her. Maybe not totally ugly, but just enough that he would be able to resist himself. But who was he kidding, Drake knew he had a hard time resisting any woman.
Drake looked around the restaurant for a homely woman just sitting and waiting for someone. Typically when he was set up by his friends, the women would be so excited to meet him that they were always at the restaurant early waiting for him. Unfortunately, he couldn’t find anyone at all, in fact, there were no single women sitting around anywhere in the restaurant.
“Table for Leblanc,” Drake said to the man at the front of the restaurant.
“Oh yes sir, this way.”
Drake sat down and ordered his favorite wine while he waited for Rose to arrive. He looked at his watch and started to get a little annoyed as the time flew by. When it hit 8:15 pm Drake was about to leave, or at least order some food and eat.
Then he saw her.
She was beautiful. Nothing like the women his brother typically set him up with. Rose had long dark brown hair and the perfect hourglass body. She had on a navy blue dress and stunning red shoes with matching red lips.
Although she certainly wasn’t a size two, Rose was perfectly proportioned and very slim. He thought she reminded him of one of the Victoria Secrets models. Curvy in all the right places. She was a delectable sight to see and Drake knew right away he was going to struggle on their date. He knew his mind would spend most of the night thinking about having her in his bed.
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