Amazing Hawaii Master

An hour later, I called Meghan and told her I would be going with Jenn, I felt terrible, it took me a while to be up for calling Jenn and being happy about it.

Jenn was genuinely excited to hear she'd won and was talking much faster than at lunch. "Ok, so can we get started now?" was the main thrust of her end of the conversation.

"I'm starving, can we meet for dinner and then go back to my place and we'll get started then."

"Sure, I haven't eaten, what should I wear? I brought a nice dress because you okayed it for someone else in your email."

"Of course, and you brought your comfy sweats right?"

She giggled - it was so cute! "Of course, I love them."

"Yeah, wear your dress, any particular type of food you'd like?"

"No, this will be the last time you get to pick anything, so pick well."

I laughed, "Gotcha, I'll be there in an hour. And don't wear your hair back this time."

When I picked her up I was glad to see how nice she looked in a dark blue dress with her hair not pushed back in the headband. I couldn't help but think of what she'd look like tomorrow, what I'd look like as her slave.

"Are you going to be able to get a tan when you're here?" I asked.

"Yeah, I'm pretty pale naturally, but I'll darken up a bit, probably the first time ever I can do it without tan lines, your place is totally secluded right?"

"Completely, for a few miles."

"That sounds amazing, I'm excited to see it."

"Yeah, I love it."

We talked logistics for a bit, I told her I had all her toys, and she could go through Meghan's too. I got all the food and drinks she wanted, and she had recommended I get an expensive bed set, sheets, blanket, pillows and thick robes and towels. I liked that she asked for them, the other girls seemed almost sorry to ask for things when I told them to.

We talked about our lives for the most part, mostly about mine, but I got some stuff out of her, she was very philanthropic and a lot of her goals were focused on that.

She was pretty easy about answering my questions, but she just seems interested in how I got to where I was. That is where the conversation was mostly focused on.

After we finished eating she grabbed my hand as we walked out together, we drove the 40 minute drive to my place and when we pulled in I said, "OK, do you have a cellphone, camera, anything that I don't want you to have?"

"Nope, at the hotel with my friend."

"Ok, I planned on searching your bag, but I trust you totally."

"Thanks."

"OK, I'm ready, let's begin, if you'd like a tour of the place first-"

"It's a house, I'll figure it out quick, it's fine. Is the door locked?" she said rapidly, gesturing to the house.

I shook my head.

"OK, stay right here, I'll be back."

She went into the house and came back out 20 minutes later. "Grab my stuff and bring it into my bedroom."

She took her time getting to the bedroom and she then said "OK, clear out a space in your closet that has more than enough room for all my stuff, get you stuff out of here and put all my stuff away nicely."

She then lay on my bed and watched me empty out a bunch of closet space and drawers and put my clothes in the laundry room before I started hanging up her clothes away on the hanger and in the drawers, she wasn't kidding about hating underwear, she hadn't packed any. Near the end of this she had wandered off outside to check out the area.

She came back to find me waiting on the bed. "Get me a glass of the red I had you buy, I'm thirsty."

I complied, seeing her lay back on the bed in her blue dress and cheap flip flops, she looked totally relaxed. I actually felt good about it, to finally be started, and to have things go well in this short time. I was already pleased that she was pleased. I realized that I am much more nervous and eager to please Jenn, I think that's what made me pick her.

"Good," she said as I handed her the wine, "I guess since it's 9 pm here, it's actually 2 in the morning in Cincy, that explains why I'm so tired, that and the long ass flight here in the morning. I thought that maybe I should try to stay up to adjust to the time zone here, but I realized it's a trap. I don't have to adjust to anyone's schedule here, I can sleep whenever I want and I even have a man who will bend over backward to accommodate me, isn't that right my little pet?"

"Yes, it is."

"I have to be careful to remember I have total freedom and control here. Not taking full advantage would be an awful waste. And from now on, always call me "My Love" it sounds so pleasant to hear, try it now, and say it with feeling, like you do love me, like how you felt as you stared at my pictures, picked me over everyone else, dreamed of what I looked like naked, dreamed of me here on your bed right now, say it like that.."

"Anything you say, my love."

"Great, that was amazing, you say it with such longing, I love it, I want you to focus on how much you desire me every time you answer me. Pretend like you're feeling my soft, warm, naked body pressed tightly against you to warm you up, every time you speak."

"Mmmm," I began, involuntarily, letting that great scene play in my head, "Yes, my love."

"I adore the way you say it, make sure to say it like that always. You on the other hand, little servant, will have many names, depending on the situation, but I like to think of you as my little pet, who will cherish the ground I walk on unconditionally, who will sit, stay, do a flip for my attention and approval, without any regard for your own opinions, self respect and basic human dignity, much like a little puppy. Let's try: Sit Sparky."

I hesitated, feeling ridiculous and humiliated, but sat on the ground.

"Good boy, now lie down. I leaned back and lay on my back. Good boy, sit again Sparky."

"Ok, now speak Sparky," she said, lying back with an amused smile on her face, speaking as if to a dog, "Bark for Jenn."

I looked at her as I debated doing such a ridiculous, degrading thing for a woman.

She saw this and said, in a voice she'd actually use to talk to a dog still: "Scruffy, you have to be a good boy or else I won't give you attention or rewards. Bark."

I still couldn't bring myself to do it, and made defiant eye contact with her. "Lassie, bark for me and I'll give you a treat. You want my attention and I'm sure you want a treat don't you my pet?"

I looked over her body as I remembered to picture it naked against mine, I closed my eyes to see it vividly as I said "yes, my love" in a dreamy voice.

"Then bark right now, I won't ask again."

I did it, feeling defeated more than anything. "Woof!"

"Oh, that's not a good bark, do it louder."

"WOOF!" I said loudly.

"There, that's good, see that was easy." she finally dropped the exaggerated emotion and dog voice and said, trying to keep her amusement in check "Go fetch your love another glass of wine, Sparky, then come back for your treat."

I came back to see her watching me with amusement as I entered carrying her wine glass and handed it to her, "Here you go, my love."

"My god, just you saying it like that, it makes me feel so good. It washes over me like a warm breeze," she said as she leaned up against the headboard to sip her wine. "Now for your treat, you may massage my feet while I enjoy this delightful wine, remove my sandals..with your mouth."

I bit the edge of the shoe on her right foot, just above her toes and pulled it off, the second slid off easily as well.

"Good, hop up on the bed so you can do a good job," Jenn asked, "Are you a good foot rubber?"

"I've never really tried...my love."

"Mmm, we'll see what happens, go ahead."

I took one foot tentatively in my hands and started to rub her sole. "Are you disappointed with your reward, my servant? You don't think me letting you take care of my precious feet is an honor?"

"No, I'm eager to massage your feet...well, I was just expecting a more...intimate treat."

She laughed, "Please, how bold! You are nowhere near proving you are deserving of that yet. Circle both your thumbs on my soles, more pressure, there you go."

She gave me more directions as we went along and I started to understand how she wanted it done, even though she seemed to have lost her patience somewhat before I was doing it how she wanted me to. Her attitude was one of disappointment, but not surprised, like she expected it. I didn't like that she doubted me and even worse was proved right.

After 15 more minutes of me rubbing her foot in silence she seemed to finally become relaxed and happy.

"You know, not barking when I asked you, not doing anything right away, I can't have that. I need you to understand and do anything I say right when I say it. I warn you that it's a much better road for you to just do it, then disobey and face the repercussions after, they will always be worse."

"Yes, my love, I'm sorry, I'm still new to this."

"It's very evident you are new, remember that I may take to physical punishment from time to time for any infraction of our rules, remember that when you don't want to do what I say. If you had just barked right away this would have been so much easier on you, now I need to break you out of it, to make sure you'll obey me, I need to give you even more difficult tasks until I am sure you will listen unquestioningly. Your first few days got much less pleasant. You aren't allowed to ask yourself if its ok before you do it. You don't make the decisions anymore. I suppose some of that is time, you will have to learn to trust what I say unconditionally, as if it's your own reflex."

"Yes, my love."

"Good, switch feet."

"My love?" she could tell every time I was going to say something because I paused to visible picture her beautiful body naked against me.

"Yes slave?"

"During tasks like this can I talk, when am I allowed to talk?"

"That's a good question, I feel that while you should probably never speak out of turn, it feels too formal, and besides I wouldn't enjoy it. You are free to talk to me about anything that isn't directly related to you as my slave, your tasks, etc. And if I ever don't want to hear from you I'll simply tell you to stop talking, it's easy enough. When we are engaging in casual conversation there is no need to use 'my love' either, save that for when you are acknowledging my orders or addressing me."

"Ok, my love."

We then talked for a little while longer as I rubbed her foot, she had finished her wine long ago and was now laid back with her eyes closed, enjoying the foot rub.

"Now kiss my feet, kiss them all over, suck my toes."

I leaned over to start on the top of her foot and began to kiss the top of her foot tenderly.

"My foot isn't dirty or anything like that?"

"No, your feet are lovely."

"Shame."

I kept kissing the top of her foot, then switched to the sole until finally I started to suck on her toes, taking them one by one completely into my mouth. I then switched to the other foot and repeated the process.

She had me go through it one more time and then said, "I need a shower, do you have the fluffy pillows and robes I requested?"

"Yes, my love."

"Great, I want you to make my bed with all the bed supplies I requested, you haven't used them yet, like I asked right?"

"No, they are still all in their packaging."

"Perfect."

She then got up and her and her glistening feet padded off to the bathroom, I watched her leave, her round ass, wrapped tightly in that dress, swaying slightly as she left.

I made the bed and waited in the chair in the corner for her to return. She entered with the baby blue robe wrapped all around her small body.

"Great, I can tuck myself in tonight, you haven't earned the right to see me naked yet. I know it's only 11, but I am exhausted. I want you to sleep on the old sheets here on the floor beside my bed. For now you may go and eat, drink, use the bathroom whatever, but when you're done, return quietly and be in that spot when I wake up. Keep those same clothes on for now, if they are uncomfortable, remember why it's important to bark when I say so. Got it, my pet?"

"Yes, my love, sleep well."

"I intend to, I've had a really long day"

I wasn't tired as I usually fall asleep around 2 am, so I was up for hours just laying on the uncomfortable floor in the dark. I didn't sleep well and was up most of the night, I lay awake from 7 am hoping Jenn would get up, but she didn't even start to stir until after 9, and a bit after 10 I finally heard.

"mmm, servant?"

I sat up, "yes, my love."

"Go make breakfast, coffee and omelets with fruit cups, for both of us. Bring mine back to the bed first, and throw me a t shirt of yours."

I came back with her meal to find her sitting upright in bed wearing my tshirt with her legs still under the covers. I put the meal on her lap and said, "Is there anything else I can get you?"

"Not now, just hold my coffee until I need it."

I began some small talk about how she slept for a little while until I grew content simply watching her eat. Her thin arms flexing slightly with every movement to her mouth. Her delicate lips letting each morsel of food pass. Her straight, black hair looked just a little out of place, she looked so cuddly and warm and innocent and fragile, I adored her.

"Coffee," she took a sip, "here."

She finished and said "That was good, servant, I feel amazing today, so refreshed and full, I'm over the time difference, jet lag, all that. I'm excited about how happy and healthy and relaxed I am right now, and we haven't even started yet. Go ahead and eat your meal, I'm going to have another nice shower, then we can begin our day."

I ate my now cold meal and waited for a while as Jenn was taking a long time in the shower. Thinking of her in that shower made me feel dirty in these clothes I'd slept in.

"Ok, today is an important day, we need to make sure you'll listen to everything I have to say and you have to prove you're worthy of being my complete slave. You're going to be put to work, so take a big drink of water."

She then left to get changed out of another of the robes I had bought her.

She emerged in a light sundress that would wave in even the slightest breeze. "OK, I need you to do some work for me while I get some alone time, come outside."

We got out to the back porch and she said "Take off everything you are wearing but your underwear."

I looked around and then at her again and started to take off my shoes and socks.

"It's still entirely unacceptable, your obedience and compliance are very low. When I say something I need you to just do it, to not even think about it. If you saw someone around you wouldn't have taken off your clothes. It doesn't matter if you saw 10 people, I said it, you do it."

"It's blatantly obvious you are thinking about it...a lot. Right now you have so many filters running through your head before you do it. 'Do I want to?' 'Will I be embarrassed?' 'What happens if I don't?' etc, that has to stop, we have to blast through all of those filters until you simply do, you hear and then you do, you don't think about if it's good or bad, or whatever, if it's embarrassing or humiliating. Fuck, if it is you are lucky, you'll get turned on. We both know that. You begged me to come here and treat you like my slave and then you get embarrassed when you do it? Does that make sense?"

She then softened her disposition, "But it's ok, this is only our first day, after you finish your chores I know how we can train you to get over this. Does that sound good? Not living in your own head and analyzing everything I ask, but just listening and experiencing it. I actually imagine once you get it, it will be quite invigorating to not have to decide anything, but to just sit back and let whatever comes, come."

"Anyways, see that coconut tree, the only one we can see down the beach maybe 2 miles?"

"Yes, my love." I said as I admired her soft hair in the breeze.

"I want you to go over there and pick me up a coconut from that tree and bring it back, OK?"

"Yes, my love."

"Before you go, stick your face in the sand."

"What?" I exclaimed in surprise, looking at her with wide eyes.

"Yup, we have a lot of work to do, you still aren't listening, do it because I said so, that's all you need to know and then go get that coconut. I want you to go as fast as you can."

"Yes, my love." I took off at a stiff jog after pushing my face in the sun heated sand, and did the best I could, it took me a while to knock a coconut down, but I did and jogged home, when I got to the house I was exhausted, thirsty and drenched in sweat.

"You haven't been in Hawaii long have you?"

"No, my love."

"It's obvious, you are barely tan, it's embarrassing," she said as she looked me over with mild disdain, "Good job on the coconut, it will be fine, now get yourself a drink of water and use all the coconut juice to make me a drink."

After this she had me put back on my clothes that I had discarded in the sand while I was still hot and sticky and then she said "OK, we're going into town, take us to the largest mall, we're going to work hard to make sure you listen to whatever I say without thinking about it. If you can do it in front of a group of people, then at home won't be a problem anymore."

Scared the whole way, we arrived at the mall in about an hour and Jenn made me hold the door for her to get out and then walk behind her into the mall, holding all her possessions. We first went to the book store because Jenn wanted something to read during her beach lounging.

"OK, you remember what I told you about not thinking, just doing?"

I gulped and nodded, incredibly nervous about what was to come. "OK, I want you to skip, like small girls do, around the outside of the store for two laps. Go right now."

I had to brace myself to do it, thinking like I wasn't supposed to, I could feel Jenn's disapproval before I started to skip.

I felt mortified as people stared and laughed as I skipped around the store until I got to Jenn, who was pleased. "You didn't listen right away, but you did the task. Come on, let's find me some books."

Jenn picked a few books out she wanted to look through and had me carry them and find her a seat. She had me stand beside her as she sat, turning the pages as she instructed, holding the book awkwardly in front of her. A lot of people did a double take at seeing this.

I started adjusting more and more frequently, my arms getting tired, Jenn said "Arms tired? I'll let you have a break." She took the book from me.

"Thanks, my love."

"I'm happy to help, now get down on your hands and knees and be my footstool, but before that take my sandals off." Her offer of help was a tease and nothing more.

I saw a girl sitting opposite the aisle, looking over her book at us. I hesitated to get down to my knees.

Jenn smacked my ass firmly, "Now, footstool. Don't think ever." She said loudly so anyone in the vicinity heard.

Very embarrassed, with people watching in shock, I got down on my knees and gently slide her sandals off her feet before crawling under her extended legs as she used me for a footstool.

"Take my sandals off with your mouth," she said angrily and pushed her bare foot roughly over my face before relaxing to read.

I stayed like that for about 40 minutes, my face red the whole time as many people walked by, shocked at what they saw. Finally, Jenn was done reading and had me kiss both her feet and slide her shoes back on. I got up to see the girl was still there, still watching.

"Can my pet kiss your feet?" Jenn asked loudly as I cringed. She looked taken a back, but then gave a small grin and said,"OK."

"Go on, footstool." Jenn said.

My shoulders slumped submissively I walked to her and got on my knees and grabbed her foot by the ankle and lifted it a bit to kiss it, and then the other. "Thank you," I said softly, humiliated. Thankfully, that was over and we left the store.