The Island Emily

**********************************

Author's Note: This is one of several short stories in a series called "The Island." All stories take place in the same secret island resort, where women come to serve as sex slaves for a year, under the control of a man known only as "Sir."

All characters are over 18. All places, characters, and stories are completely fictional. Sexual slavery and human trafficking are real, serious problems, and rape and kidnapping are illegal.

***********************************

The girl stared at me from across the room, blue eyes wide with fear and confusion, blond hair damp with sweat. This first moment, this first meeting, told me a lot about how the year would go. Was she paralyzed by her fear, or motivated? Was she in awe of me, or did she hate me? Would she do anything to please me, or would she fight me at every turn?

"Come in, Emily. Let me see you." My opening line, honed over years of use, with dozens of girls, delivered in an even, unemotional tone. Not meant to frighten, only to invite, to greet.

The girl took several steps forward but stopped short of my desk. Interesting.

Andrew's report ranked her squarely as "mediocre." She'd done everything she was told, but it had taken more coercion than I would have liked. Andrew was frustrated, but not overly so. His comments suggested he was more annoyed with the field agents than with the girl. He indicated that they had not properly prepared her. It was possible. The Midwest agents tended toward lenient. I'd have to have a talk with them before their next assignment.

I waited, gave her a chance to continue forward without prompting. I focused on my screen, rereading her profile, apparently paying her little mind. Emily, Minneapolis, 23 years old, 5'4", 114 pounds, 32B, three partners, limited experience.

It would be quite cold in Minneapolis at this time of year. Arriving on the Island must have been a shock just for the change in temperature.

She took another several steps toward me after just a few seconds of hesitation. Good girl. I smiled at her, pleased.

I gazed openly at her now. Beautiful girl. But then, they all were. Her breasts were perky, with large, pink nipples. She was quite pale, the skin of her stomach nearly translucent, unblemished. Even her pubic hair was light, though darker than the hair on her head. Muscular legs. I glanced at her profile. Track and field in school. Excellent.

Her hands twitched. The girls knew by this point not to bother covering themselves, but most still wanted to.

"Why did you refuse to masturbate on the plane?" I asked.

She swallowed, trembled. I'd caught her off guard. "I - I didn't," she protested.

I leaned back in my chair, adopting a casual pose, hands behind my head. "You were whipped, and then my agent had to put the vibrator in you before you took over. I consider that refusing." I'd enjoyed the video, actually. She'd squirmed under the crop, breasts going from white to red. Bradley had chosen a big vibrator.

Her cheeks reddened, and she opened her mouth to argue. I raised an eyebrow. That was usually enough. She closed her mouth.

"Andrew says you resisted every order. Is there some part of 'do what you're told' that's difficult for you to understand?"

"N - No."

"No, Sir," I corrected.

"Uh. No, Sir."

"Good. My men on the plane went easy on you. I will not be so lenient."

One tear. Only one. She was braver than I expected.

"Yes, Sir," she said.

"Good. Now, have a seat."

She sat in a chair on the other side of my desk, hands between tightly clenched thighs. A familiar pose.

I straightened, rested my forearms on the edge of the desk, leaned forward. Every motion had to be perfectly controlled, planned. The girls would read into anything I did. They would analyze my posture, search my face for clues. "Now, Emily, I have here your sexual history. We have quite a bit of work to do. Clients have many different preferences and desires, and you will fulfill them all. You will spend the next week or two here with me, undergoing intensive training. When your training is complete, you will be available for hire by clients. I will explain exactly how everything works shortly. The most important thing for you to remember is this: I pride myself on providing an environment in which my girls are compliant and willing. If you cannot live up to that standard, you will be punished. If after punishment, you still cannot live up to that standard, you risk being sent home. If you are sent home, you will receive no compensation. Do you understand?" It was best to dive right in, while they were still reeling, wondering what I was going to do.

She hesitated just long enough that I thought I might have to repeat myself. Then, finally, "Yes, Sir." Quiet but clear. We were making progress.

"Andrew told you about the hormone shots, correct?"

She was startled by the change of direction. Keep them guessing.

"Um, yes, Sir?"

"We'll start with that. Then you will be punished for your disobedience."

She'd been waiting for that. I watched her eyes dart around the room, wondering how and where I would punish her, wondering how much it would hurt. I took the injection supplies from my desk drawer, letting my words sink in.

The shot was the easy part. She hardly flinched. "Good," I said. Praise was important. "You'll have a shot every three months and take a pregnancy test every six weeks. Now, follow me." With more cooperative girls, I allowed more conversation, but with this one, I'd need to strike while she was still processing everything.

I started toward the training room without looking at her. I was interested to see whether she would come without prompting. I didn't quite have a read on her yet. I would soon.

Shuffling footsteps behind me. Excellent. I opened the door to the training room and stepped aside, letting her have a first glimpse. She halted just inside, gazing around in bewilderment and fear, eyes lingering on the suspension hook, the frame, the benches. Still so much fear. But she was inside. I moved up behind her and shut the door.

Reluctance and hesitation, but no outright refusal. Andrew said she'd swallowed, once she'd been convinced to actually give the blow job, which was a point in her favor. He'd spanked her, but she'd avoided the flogger. Mediocre indeed.

Ass, then. "You will be spending a great deal of time in here over the next few days," I said. She jumped. "For now, you will be punished for your disobedience. Learn the lesson quickly, and you will be spared considerably more pain in the future." She was on the brink. It might only take this one demonstration, if I calibrated it correctly.

I touched her then, finally, a hand on her upper back, very gentle. "50 lashes," I pronounced. She jerked in shock. Too many? I'd soon find out. I guided her to the flogging table. I wouldn't make her dangle by the wrists. Not this time.

I stood behind her. She was cooperating now. With the very tips of my fingers, I caressed her neck, her shoulders. I saw goosebumps sprout. I wanted to touch those tits so badly. Was now the time? She stiffened, but her breath quickened. Yes. I continued, between her shoulder blades, around and under her breasts, then with the palms of my hands cupped her breasts. They were firm, the skin so soft, nipples poking out like little flower buds unsure if spring had arrived. A rush of blood to my cock. Soon.

I let my hands trail down farther, to her navel, then around to her hips. Then one hand on her lower back while I adjusted the table with the other. She'd had enough time to study the apparatus, to figure out what it was for. I left her standing there, wondering if she'd heard me wrong, and retrieved a flogger from the rack. A light one. I'd go easy on her. She wouldn't know, but that didn't matter.

She was watching me now, still standing where I'd left her, head turned, eyes tracking me. I returned.

"Bend," I said. She was fixated on the flogger in my hand, too afraid to hear me. I brought it back, then flicked it forward so the tips of the tails just touched her ass. A wake-up call. It shouldn't have hurt, but she yelped. "Bend," I repeated.

She bent at the waist, leaning forward over the table. I pushed her down until her cheek was pressed into the padded surface, then guided one arm into position and then the other so they were stretched up and out, secured by wrist cuffs. She tested her bonds. They all did that.

I squatted at her feet and coaxed her to open her legs, cuffed her ankles against the legs of the table. She tested those restraints, too.

She whimpered.

I stood beside her, where she could see me. "You agreed to serve for one year in exchange for a rather generous compensation package. As long as you serve me, I expect total obedience. It's simple. Do as you're told, and we both win. The happier your clients are, the happier I am. You make your clients happy by doing exactly what they want you to do and being exactly who they want you to be. Willingly." I lifted the flogger. "This is the flogger," I said. "You have earned 50 lashes on the ass."

Surrender was the key. If she surrendered now, the rest of the week would go smoothly, and I would anticipate a high earner and satisfied clients. If she resisted, she would suffer. I still wasn't sure what she would do. It made me uncomfortable.

I positioned myself behind her and wielded the flogger. It struck with a pleasing thwack. She jerked, cried out. I kept a silent count, red splotches blooming on her white ass. Whimpers and sobs turned to screams. At 25, I paused.

"Take a moment," I murmured. Her sobs quieted.

She wasn't begging yet. Surprising. She hadn't spoken at all since the shot, in fact. Unusual. What was in her head?

I resumed without warning.

"Please!" she shrieked. "No more!" Ah, finally, a reaction.

I continued to 50 at the same steady rate. She pleaded with me just once more. Maybe she knew it would do no good.

I put the flogger away while I waited for her to calm. Now the test. I returned to her side.

"All done," I said. Her hair was mussed and tangled. I combed it with my fingers, kind, compassionate, caring. When her crying stopped, I let my hand linger on the back of her neck. "Good girl."

I held her gaze as my hand inched down her back. A firmer touch, more deliberate. She quivered. She tensed as I neared her ass, but I stopped just above the highest red mark. I didn't want to hurt her. Quite the opposite.

"You did very well," I said. Praise. "Very well." She stared up at me, licked her lips. I lifted my hand, ceased contact. The muscles of her back rippled, her hips moved. The question in her eyes, Why aren't you releasing me?

I stepped out of her line of sight, behind her again. I ran my hand up her inner thigh, dipped into her pussy with one finger.

Wet.

I smiled. She would do just fine.

She bucked her hips, whimpered. They were always so confused at first. How could they be aroused after they'd just been whipped? How could they crave my touch when just moments ago they were begging me to stop?

My thumb found her clitoris. She inhaled, held her breath. Light circles, then firmer when she moaned. I slipped two fingers into her pussy. So wet, so ready. Her breath exploded out of her then. "Let go," I murmured.

I wanted her. It was always this moment, just before they came for me, just before the surrender, that affection was born. She was mine now.

Her breath was coming in sharp gasps, her moans grew louder. I kept up the steady pressure. She rose up on her toes, as much as her restraints would allow, and then she let go and came with a guttural shout.

I released her ankles and wrists, let her catch her breath. "Good, Emily," I said. "Very, very good." I helped her up, led her back out to the office. Her knees buckled, and she grabbed my arms for support.

Time to fuck.

"Go lie on the couch," I said, pointing to the chaise. That's where I always started. Right here in the middle of the office.

She lay back, gingerly, but without hesitation. Much better. Those eyes, full of questions, but she was too afraid to speak.

"It is my privilege to be the first to have sex with each new girl who comes to me. I understand you have had three sexual partners, and that one was a woman?" That little tidbit had nearly slipped by unnoticed. She was certainly not the first girl to come to me who had experimented, but it did make that aspect of her training much easier and much more interesting.

"Yes, Sir," she said. Her voice was hoarse.

"But none of your sexual relationships was long-term."

"No, Sir."

Relatively inexperienced. "I will use all three of your holes, starting with your mouth and finishing in your ass." Sometimes I let the anal sex be a surprise, and sometimes I gave warning. I had found it didn't really matter whether they knew it was coming. This time, I felt like telling her. Her eyes widened, her mouth opened.

"I've never done that, Sir," she said. I had expected a protest. Good girl.

"I know. You will learn. Don't be embarrassed. It is fairly typical for my girls to have their first anal experience with me." I didn't think she was embarrassed about it. More likely, she was either scared or disgusted, but if I told her she shouldn't be embarrassed, then she'd think she should be. I went to the cabinet and chose a butt plug and some lube. I showed it to her. "This is a butt plug. It would be very painful for you if I tried to fuck your ass without some preparation. This will help to relax and stretch your sphincter." I let her measure it with her eyes, clench her ass. She shook her head ever so slightly. "Pull your knees up to your chest and hug them," I said.

She responded slowly, but she did it.

"Just try to relax," I said. I meant it, but I was certain she wouldn't be able to. I knelt beside her and put lube on the first two fingers of my left hand. A little pain was unavoidable, but I didn't actually want her to suffer. It was best just to get this part over with.

I pressed against her asshole with one finger. It puckered, she sucked in, tried to keep me out. It was mostly involuntary. She'd have to learn to fight that instinct. Now a distraction. I pinched her nipple. She forgot about her anus briefly, and my finger slid inside. A little gasp. The first finger never hurt, but they always thought it would. She relaxed, just slightly.

I pushed in up to the second knuckle, wiggled my finger, felt her sphincter pulse. I used my other hand to stroke her clit now.

The second finger, and this required an unnatural stretching, mild pain, but unexpected.

"No, please," she whispered.

She had been forced to do quite a few things already that she didn't want to do. She had been touched, groped, and fondled. She'd been paraded around naked. She'd been whipped. She'd given a blow job to a man whose name she didn't even know. But she hadn't had to have sex yet. And now the full realization would hit her, that a relative stranger was about to put his cock in her, whether she wanted him to or not. But this is what she had agreed to. This is what I was paying her for.

She squirmed, started to cry. I waited for a full count of 60 before pulling my fingers out. I lubricated the butt plug quickly, then continued my attention to her clit while I very slowly inserted it.

Some girls whined. Some protested. Some screamed. Some cried. None of them liked this part. Emily sucked in her breath and held it, tears coursing down her cheeks. It was the worst when they cried. The pain would fade, but she didn't know that yet.

It was in.

"Breathe, Emily," I said. She hadn't exhaled yet.

She breathed out slowly, eyes closed. A slow breath in, then out again. She relaxed.

"Good girl," I said.

My cock twitched, swelled. Soon.

"Now you'll give me your best blow job." I undressed and sat beside her. "Kneel in front of me." She was still hugging her knees. She wouldn't sit up, instead opting to roll over and slither backward off the couch. Almost all of them did that, too. I suppressed a smile.

Moment of truth. There was nothing more disappointing than a bad blow job.

I smiled down at her. She really was adorable. I touched her cheek, wiped away a stray tear.

She studied my cock, wrapped her hand around it. Just the right amount of pressure. She knew what she was doing. She adjusted her position, probably trying to find a way to kneel without sitting on the butt plug. Her hair fell forward around her face, and her lips closed around my cock. Oh, did she ever know what she was doing! She took me deep, almost all the way. "You can deep-throat!" Highly unusual, but a most welcome development. She came up, flicked her eyes up toward me, a faint smile on her lips, then plunged down again, this time all the way. Her throat massaged my cock. "Oh, Emily!" I said. "You do surprise me."

I let her continue for three or four minutes, but then I had to stop her. As much as I would have enjoyed letting her finish me off, we had more to do.

"Okay, stop now. That was excellent." Praise where praise is due. "Lie back, let me try your pussy." That wiped the smile off her face. Too bad. Maybe she'd thought if she could make me come in her mouth, she could avoid the rest. She would not be the first to try it. None had succeeded.

She obeyed. The little black knob of the butt plug poked out between her butt cheeks, enticing. Her nipples were rigid. I palmed them, then leaned over her to suckle one. I hadn't allowed myself that indulgence yet. She grunted. I sucked hard, tonguing the tip of her nipple at the same time, pinching the other nipple in parallel. She lifted her ass, pressing her hips up to me.

I entered her slowly. I'd had girls who truly wanted me, and with them, I could fuck hard. But when there was reluctance, I had to take my time, let them get used to the idea. Her pussy embraced me, slick and tight. Her hands went to my shoulders, pushing me away at first, then gripping, fingernails digging into my skin. "Good girl," I said. She closed her eyes, parted her lips. Good girl.

I thrust gently, picking up my pace steadily as she bent her knees and hooked her legs around my waist. "Not so bad, is it?" I brought us both almost to the brink, then backed off. She cried out in frustration. No, I'd let her come, but not until I was in her ass. She had to learn to like it, and this was the best way.

I pulled out. "Turn over now. I'll come in your ass."

She opened her eyes, a mass of confusion, fear, arousal, uncertainty, almost everything a person could feel.

She rolled over after a hesitation a little longer than I would have liked. "Tuck your knees under you."

She did as I said. I smeared lube on my cock, then tugged on the butt plug. She had to figure out how to let me remove it, but it popped out with a little encouragement. It was my turn to take a deep breath. This took control.

She dug her fingers into the cushion, teeth clenched, toes curled. This would be agony if she didn't relax a little. The fear would feed on itself, and the pain would be a self-fulfilling prophecy. I shook my head and aligned my cock, pushed the head in.

"No. No, I don't want to do this," she whined.

"You have to relax, Emily," I said. I massaged the back of her neck, pushed forward another half-inch. There was nothing, nothing like an untried ass. I wanted to plunge in, bury myself in her ass in one stroke, but I wouldn't do that to her.

She coughed, choked. Her anus tried to close, a vise around my cock. I gritted my teeth and waited.

"Breathe, Emily. You're doing so well."

She took a nice, deep breath, and I opened her more, taking a couple of inches all at once this time. I reached under her and pinched her nipples, and on her next intake of breath, I was in.