Amazing Hawaii Master

As I lay back on my towel in the sand, eyes closed, letting the warm breeze drift over my almost naked body I took a sip of a freshly opened beer, the cold liquid running through my body.

"Ahhh," I exhaled. I've arrived, I thought...finally.

10 years ago I dropped out of high school at the age of 17 because I wanted to start my own business, I knew that I could do it, school could get me no further. I also knew it would be a long, hard road so I wanted to get started right away.

I was right on both accounts, it was long and hard, but I did it. I'd worked my ass off for a decade but I sold a portion of the company and stepped down in my active role , I'd now collect checks while I let others do the work.

This happened less than a month ago, and since then I'd sold my condo and bought this place, this amazing place. It's a private bungalow on the beach in a secluded area in Hawaii, no one within a 20 minute drive, the nearest city 20 minutes past that.

For the past week, I'd been waking to the sounds of the ocean, the waves hitting the sand 50 feet from my window. I often pondered whether this was worth it all, I'd spent a lot of prime years in my life just working, I'd missed out on a lot of experiences, especially college, but also so many other little things, I barely had any real hobbies, and perhaps the biggest thing was I'd never had time for a relationship, I'd been on sporadic dates, a lot, but I'd never met anyone who could make me take the time out of my life for them, and I know now that that was a mistake.

I'd met some great people, but brushed them off because they were getting in the way of my single minded focus.

I realized that any mistakes in the past, any obligations on my life, were now gone, I could do what I wanted, what I deep down wanted, and if I didn't for any reason, then the last 10 years of my life would truly have gone to waste.

What did I want the most? I thought. That was easy, a beautiful, amazing women to share all this with, but was it that easy? I know that in my sex life for the past 10 years I was all about 'getting mine' I wasn't interested in woman for relationships, I wanted to meet ones that would hook up, no commitments, nothing.

I realized too, that my favorite ones were the ones that I could let go with, not be in charge, making decisions. The girls that would take over, be in charge, the ones that would get on top of me and ride me hard, while I would just lay back and watch them work.

I'd never made the connection before, but I'd had a passing sexual fantasy, one that came up in dreams more often than conscious thought that now seemed very connected to my sex life up to this point.

I then started to ponder a way to make this fantasy a reality. At first, I felt intense fear and reluctance as I'd never thought about anything like this before in my life, then I started to think deeper, my fear faded, the details feel into place and I started to get excited, nervous excited, but excited.

I laid around for another hour thinking about it, went for a swim in the ocean, the whole time rolling it over in my mind.

I was finally ready and headed inside to my laptop and I started browsing around any message board, dating websites, etc that would have college girls on them. I figured the timing would be perfect, as exams were finishing right about now leading into summer.

I found a bunch of sites and decided to write my pitch:

This may be the most unusual request you've ever read in your life, it's certainly the most unusual I've ever asked, or even heard about. I assure you I am 100% serious.

I'm a 26 year old single guy and I just moved into a beach house in Hawaii. I own my own business and am not needed there for long periods of time. I never went to college as I was busy with my business the whole time, I am looking for a college co-ed who has a few weeks of spare time in her summer vacation.

Here's the strange part, I've recently decided that I want to try some dominant-submissive stuff, so I am looking for a girl to dominate me for 2 weeks in my place in Hawaii.

The trip would be all expenses paid, I mean everything, food, plane, you will have everything you need, you'll live in luxury for the whole time. But, this isn't a regular Cancun, all inclusive deal, this is ALL inclusive, you have me as your complete and total control, I'll take care of whatever you need, you have no need to lift a finger, anything you want done for you you simply ask me and I will.

If you're interested I want a girl who is college aged, attractive, and interested in being a dominate, though no experience is required, you must be willing and able to order me around for two weeks as basically your slave, sexual and otherwise.

I can promise that this will be the most pleasurable two weeks of your life, you'll have a private beach house and a man willing to do whatever it takes to please you, to satisfy you 24/7.

I've attached picture of myself in this message.

As far as my interests on being a submissive, bondage, teasing, some spanking/pain/punishment stuff, humiliation and total service to you, are what gets me turned on about all this.

If you are interested please reply with the following details: First name, real age, pictures, earliest departure date and latest return date, at least one picture in bikini and a face close-up, but the more pictures the better, nothing with less than a bikini, I kind of want it to be a surprise, but all sexy pictures without nudity are strongly encouraged.

I have a whole bunch of questions, but I have to be sure I am sexually attracted to you before I waste our time. I'll be contacting probably the 10-20 girls who I find turn me on the most. Note that your pictures will not be shared with ANYONE but me.

Thanks for applying and I hope to hear from you soon. Any questions, please contact me, you have 1 week to apply.

And with that I went to all the sites I had bookmarked and posted it as a profile or to a message board and shaking with excitement and uncertainty, I turned the computer off and headed out for a run along the beach.

I resisted checking my email and profiles for a whole week to let the time run out. I actually let it run that 7th day, so on the 8th morning, very excited, I began to check for applicants, praying I got at least 1 I found hot.

Amazed, I had a bit over 100 girls apply from all across America. Realizing that today was going to be an awesome day, I grabbed a coffee and settled in. I was impressed to find a lot of girls tried really hard with the pictures, some sending 10 in different poses and outfits, a lot including a few leather or latex bdsm ones, many even explaining that they took these just for me!

I don't know how many hours I took, but I had over 40 girls that I thought were hot. I kept slowly eliminating them until I was finally down to 12, this would be a great number to work with for the next part of the interview process.

So, I sent out an email to all the girls that went like this:

Congratulations girls, you were one of 12 girls selected from over 100, I'd like to ask you a few more questions. I am hoping this will narrow it down some more.

First, I'd like to read a little bit about you in general to get an idea of your interests, personality, etc, the more you can tell me the better, but keep it under 1 page please.

I also need to know your experience with dominate-slave, if any, if not, tell me why it interests you, go into detail. I'd also like to hear about some of your favorite sexual experiences. I want you to go through the sex toy website attached and give me a list of anything you'd want on this trip to use on you and/or me. Go through the site well, add anything you may think would come in handy that you'd be interested in trying.

Give me an example of a perfect day at my place as you would run it (and you're under control, so that's how it would actually happen) and finally explain why you would be a great candidate, besides physical appearance.

Finally, I am looking for someone to truly be in control, so if you don't have a history in bdsm explain why you are certain you could be an authoritative, powerful, intimidating dominant, instead of the regular girl you are in your daily life.

Thanks, I know that this is a lot, so take your time, but I am setting a deadline for a week from now again. I would love to hear about you ladies as much as possible, but please limit your whole application to 5 pages of writing, that's probably over 2000 words, but don't feel a need to write that much if you feel like you've described what I have asked fully, there is no minimum.

I don't know how long it will take me to get through them, and how much I can limit it down, but rest assured you will know as soon as I do.

Thanks again, you guys are all incredibly sexy and I am SO excited to begin this.

Once again, I tried to push it out of my life as much as I could for the week and on that 8th day I again opened up that email account to find 12 applications, all sent within the past 3 days.

I printed them all out and matched them to the images I had also since printed in high quality. I read through each once to see if there were any easily eliminations. There were, I cut 1 for being basically incomplete, she didn't talk about herself, why she'd be good, etc. 2 girls sounded just mean spirited, it wasn't a sexual thing to them, it was a 'take out the anger,' also no good, I also thought one girl was trying to use me for a free vacation.

So that was 8, I then cut another girl who only picked a vibrator for toys, not what I am looking for.

I then cut one more girl, who was almost a professional dominatrix, she had tons of experience. That didn't vibe with me, so I was down to 6 amazing, mind blowingly attractive and qualified applicants.

I decided to put them away for the day and get back to it tomorrow.

The next day I was able to eliminate one more girl, just didn't think her application or physical appearance was quite at the level of the others, there was nothing wrong, I just knew I wouldn't have picked her.

For the next few days I wasn't sure how I could decide, I was always changing the way I'm leaning, I spent hours each day reading them over, looking at the pictures and just thinking about them.

I then decided to maybe let them make the decision for me as I had a further idea for the vacation, so I wrote them:

Hello girls, I've got it down to 5 so far, but I am stuck at the moment. I have a few more things I'd like to mention before the trip.

I want you to pack light, we will be secluded the whole time, so you can only bring nightwear, underwear, any dominant clothing you like, two sundresses and however many bikinis you would like, then sandals for footwear, a few other limited accessories will be fine, and toiletries should be brought too.

I also insist you not use your cellphone, or any electronics for the whole trip, if you bring them, we'll just put them away somewhere for the trip, it's no big deal, I do this to insist you aren't distracted, have other intentions or using me for a vacation.

There will be a car and trips to the local city can be made together. If there are any problems with this let me know immediately, if you have some specific clothes questions, or inclusions for specific reasons let me know and I'll consider it, also any other items at all you'd like let me know, especially food, drinks. I keep a fully stocked kitchen, but there's nothing fancy, a few vegetables, some meat, dairy, bread, etc, these requests won't have any affect on your standing, anything expensive or odd is fine, worst case I'll just say no, remember that I want you to be as truly as happy and comfortable as possible the whole time..

I hope this restrictions won't be a problem, even though they may take you a bit out of your comfort zone in terms of packing so light, but please remember that these few restrictions are the only ones you have to cross, after that I'm completely yours, so I hope you think it's a fair deal.

Get back to me soon, take care.

Later that day, I got the first response, and unfortunately it was negative:

I'm so sorry Brent, but I was already pretty nervous about doing it, and I don't think I could go without my cellphone for long, but know that I was determined to make it the best two weeks of both our lives, so if you do happen to reconsider, please let me know right away.

I hope you have a great time, best of luck!

Over the next two days the other results came in, they were all accepting of the situation, two were happy to try it, and the other two you could tell were uncomfortable with giving up control of their packing and world communication, but it proved how eager they were to do this. I'm not sure which response was better. They asked for various stuff for the house, from alcohol to sleeping supplies like feather pillows to beach type stuff. Three of the girls each had a special request for clothing, one a "little, tight black dress" another workout clothes and a third asked about "comfy cotton shorts and hoody." I thought all these were fine and approved them.

Again I spent two days looking over these final 4, all the girls were stunning, all had amazing applications, great personalities, healthy sexual views according to this challenge, an obvious interest in trying it and awesome day plans, creative and well thought out.

I agonized, but I eventually took off what may have been my favorite girl, just my type, so sweet and bubbly, but I just feared she couldn't get totally into it as a dominant, like she wouldn't be able to be firm and demanding, so I had to cut her, even though I was totally in love with her from her application, if this was a pick my future wife contest, she would have won, and I told her so via email.

I then to cut another girl because her perfect day and toy selection wasn't as varied and diverse as the other two.

I had an idea to narrow down the last two and contacted both girls:

Hey, congrats you are the final two girls, but you're both perfect, I can't decide. I can think of one thing: Can you both come out to Hawaii this Saturday, I'll interview you both over lunch or a coffee and pick the winner, if you don't win you are welcome to stay at a great resort in Hawaii for the weekend on me, or I can fly you back home as soon as you hear you weren't selected if that's preferable, whatever you want is fine with me.

Both emailed me back with the same request: Can I bring a girlfriend to spend the weekend if I don't make it? She can buy her own ticket.

I told both it would be fine, I'd take care of the ticket as well, I then sent out a pair of tickets to each girl, Meghan in Phoenix and Jennifer in Cincinnati. I told them to wear one of their sundresses to meet me.

The rest of the week I thought about these two girls the whole time it was crazy. Meghan was 21. She was a tall, tanned, light blond haired beauty, she was lean, but toned, as she told me she played soccer and did yoga regularly. She had a picture of herself in a bikini her body away from the camera but her face turned around to smile flirtatiously for the camera, her ass looked amazing, She had a lot of side views in her bikini to check out her great legs and firm ass, she had one of her in a club outfit, short skirt and heels and her legs were stunning, I also loved two she had of her in hot pants and a sports bra doing yoga:

Jennifer was shorter, probably 5'4", 5,5" and 19, she had simple straight black hair the always fell perfectly down her body, falling just past her shoulders. She didn't wear glasses, but if she did she'd have a really strong bookish look. She struck me, by her appearance, as very polite, nice, mild mannered..nice. She had rather pale skin, I liked it, it looked so fragile, like porcelain. She wasn't quite as lean as Meghan, but was curvy, her hips flared out to make her waist look tiny, her breasts were definitely more full, they were probably about the same sized, but on her smaller frame looked bigger, and wonderfully round looking.

She didn't exude sexuality like Meghan, frolicking in her bikini by the pool, or dress to kill in tight dresses or club wear. Jenn submitted one bikini pic, out of obligation it seemed, she wasn't as eager as Meghan was. She had her hands on her hips, and looked comfortable with herself smiling easily into the camera, then 6 more of her in various clothes, two in jeans, two in nice dresses, one in shorts and a tank top and one of her in a professional attire, white blouse and tight dress pants.

I loved both the girl's profiles and couldn't wait to meet them, I had them take separate planes a few hours apart, I had a limo meet Meghan and her friend at the airport and then drop off her friend at the hotel and then bring her to the cafe.

I waited nervously at the quiet booth I had gotten in the corner, facing away from the entrance, too scared to watch, soon enough I felt a tap on my shoulder and my blood turned cold. I looked up to see Meghan in the flesh, smiling down at me, I stood up and greeted her with a friendly hug.

I directed her to the opposite side of the booth and I sat down across from her, feeling nervous, I could tell she was too, though she played confident very well.

She looked incredible in that thin, flowered sundress, you could just barely see through it, it was cut high on her arms and legs, it looked like it was delicately wrapped around her long body. She looked breathtaking, my beach goddesss.

"It's awesome to finally meet you Meghan, I feel like we're already acquaintances, you wrote a lot in your...application."

She laughed while throwing her hair back over her shoulder, "Good, I hope you liked it."

"Of course, I'm hoping this meeting doesn't feel like an interview, I'm hoping we can just have a conversation about the next two weeks and ourselves and we'll see how it sounds, if you want to say anything or ask me something, for sure go for it. Also, don't be nervous or pressured, you already won a free weekend in hawaii for two friends, you're an amazing woman."

"That's so sweet, thanks, and I hope we can have a nice conversation too."

"Great, ok, how hard of a decision was it for you to apply?"

"Wow, umm, it's weird, I wasn't sure if I wanted to do it or not, but it wasn't fear, I was uncertain if you were legit, if I wanted to apply and probably not even get picked, but I love trying new things, so the day after I saw it, I logged back in and said, he looks good, it's a free hawaii vacation, why not try? I didn't think anything would come of it, it's surreal that I am even here. What about you, why put that ad out now, what made you do it?"

"Pretty random actually, I have tons of different fantasies and a submissive one isn't even one that comes up often, but it's weird I was thinking about my sexual history and a girl that was in control, not like submissive, but a take charge in bed type girl, always left me feeling the best, and then it clicked that I would actually like to try something like this. I only wanted college aged girls because I missed that part of my life and would like to get a piece, the best piece, of it."

"But how long until you put it up, were you scared?"

"Not really, I kind of thought, is this something that I want to do? And I said yes, at that point on I've been scared, but never to the point of turning back or even close."

"Cool."

"What appeals to you more, the pleasure you'll get from me, like sexually, as your servant and also just the pleasure of living in hawaii, or the satisfaction and power of ordering around and using me, trying something like that?"

Meghan smiled deeply at that question, "That's a good one, I haven't thought about it that way, I'm really excited to order you around, to experiment on your body basically, I'm curious, but I have to say that honestly the thought of living the life of a sexy, powerful princess is the part I've been dreaming about the most. So I guess both, Im looking forward to having everything done for me, but because I can make you do it, that's why I am so excited."