What the Outlaw Keeps

by Samantha Leal

  My sucking grew too aggressive, sending my body into another dizzying spin. Again Drake's gentle touch stopped the whirling. This time he was behind me, fingers probing my sopping wet pussy.

  "Oh god," I moaned, overwhelmed, "Please Drake, fuck me!"

  "If I do that you'll feel guilty later… won't you?"

  No… no guilt, never again!"

  Drake pressed the head of his cock against my pussy, allowing the tip to slide in. With my amplified senses that inch might as well have been a foot.

  "Oh yes, yes," I cried out, thrilled that Drake was finally inside me.

  He shifted gently, slipping another inch into me. He grabbed my upturned ankles, rocking my suspended body back and forth, sliding in more cock with each swing. Sheer inertia drove his cock in deeper, his thighs pressed against me as he thrust. My body shook, spasms of pleasure firing through every muscle of my body, every synapse of my brain.

  How long did I hang there, feeling orgasms roaring through me? It was a transcendent experience… then it stopped. His still hard cock slipped out of me. I hung there, listening to the sound of my breathing.

  Drake knelt down in front of me, his face inches from mine, "Do you understand why guilt is such a destructive force?"

  "It robs you of your pleasure," I gasped. Being suspended and helpless made honesty a reflex.

  "Exactly," He replied. Drake was holding a riding crop. Was I about to be spanked again? Could I endure any more stimulation? But the end of the riding crop wasn't hard leather; it was an array of soft feathers. Drake began to run it across my body. He wasn't tickling me; it felt more like soft caresses. Each one went through me like a string of firecrackers exploding.

  "I promised to teach you Rebecca, so listen closely," He said, running the feather across my back. "Guilt will rob you of more than pleasure. Let me give you an example. Right now I'm preparing to take over the New England Tool Company. I quietly bought up all the shares of stock and did everything possible to inflate its value." He continued stroking me with the feather, breaking down my will with each stroke, "Now I'm going to sell all those shares and break the company apart. I'll sell its assets and make even more money. Most people would experience guilt, worrying about all those people's jobs and pensions, about all the shareholders that will get stuck with nothing. But that's weak thinking… poor man's thinking. By eliminating guilt I can succeed."

  Drake knew I was a "power groupie" who loved hearing these stories. To me this was hot dirty talk, enhancing my pleasure even more. Drake continued talking, each story giving me warm chills.

  He became silent and stepped out of my limited line of sight. Oh god, I thought, is he going to leave me here? But I felt my body lowering, until I was lying on the bamboo mat listening to Mahler's symphony draw to a close. Slowly and methodically he untied the ropes. With each loosened knot I felt my body going limp, exhausted. Totally spent from an overdose of pleasure. He gently picked me up and carried me to the couch as he had the day before. We lay there for a few minutes, saying nothing until I slipped into a deep blissful sleep.

  I woke up alone. Lying there naked I remembered that my dress had been shredded early in the "Lesson." But a beautiful designer ensemble hung by the door… dress, shoes and even a matching handbag. I took the lack of underwear as a hint. Pinned to the hanger was a handwritten note reading "Noon tomorrow. PS - there is another gift waiting at your apartment."

  CHAPTER SEVEN

  I arrived home an hour later, exhausted but curious about the gift that supposedly awaited me. Nothing unusual was in my mailbox, only my phone bill and monthly crippling student loan payment. I entered my apartment cautiously, wondering if I'd find some insane gift only a billionaire could conceive. But I didn't find a polo pony grazing in the kitchen. I sat back on the couch eager to fall asleep again. Apparently Japanese rope bondage is a very relaxing experience.

  Since childhood my grandmother had drilled fiscal responsibility into my head, which included opening your bills the day they arrived. I still did it even though I'd committed the amounts to memory. My phone was the usual eighty-nine dollars and my student loan payment was… zero. I looked again, assuming they had made a mistake, but according to the statement, the balance due on my education was paid in full.

  "Holy shit," I muttered, Drake had made this Moby Dick sized monkey on my back vanish.

  The phone rang. It was David, again, but this time I answered.

  "Where have you been, I called five times?"

  "Sorry David, it's been pretty crazy."

  "So tell me, how did it go?"

  I glanced at the paid off student loan, but decided not to share that milestone, "He's an amazing man, even more fascinating in person than I imagined."

  David was silent for a moment, "Did you fuck him?"

  I shook my head, "David if I say I didn't fuck him, you'd still think I did… so what's the point? Do you want to know the interesting stuff?"

  Silence again, then, "Yeah sure."

  I told David some of Drake's fascinating tales, including the illegal ones. It was telling tales out of school but it was better than saying I hung from the ceiling sucking Drake's cock. Plus, I had other, personal motivations for sharing.

  "Holy crap," David said, "I never realized he was so hands on. Drake must really trust you to share this stuff, I mean if the press ever got a hold of this. "

  "If the press ever got a hold of it Drake would have me killed," I interjected, "Remember that."

  "How many more visits are you making?"

  "Tomorrow is the last one."

  "I bet your really going to miss him when he's gone, aren't you?"

  "Goodbye David," I replied, hanging up the phone. I knew I had to cut things off with David. It was a dead relationship. But, like I said, it's more complicated than you think.

  I slept peacefully that night, dreaming of my final lesson.

  CHAPTER EIGHT

  "Are you ready for our final lesson?" Drake asked as I got off the elevator.

  "Yes I am," I replied, without a trace of the previous day's anxiety. The final lesson would be the most challenging, but I was eager.

  "With each lesson I've pushed your boundaries further. Do you understand why?"

  I thought for a moment before answering, "So I'll recognize that my boundaries are limitless?"

  He nodded, “As is your potential… come with me."

  Once again we were in the Rumpus Room. I paused, surprised at how different it appeared. Drake had altered the lighting to something less foreboding. The room seemed warm and inviting, despite the array of S&M equipment still on display. He unzipped my dress, letting it slide to the floor, leaving me naked once again.

  We embraced, kissing passionately. Drake's hands explored my body delicately, finally sliding between my legs. I was already wet with anticipation, wondering what new challenge waited.

  "I have something to show you," He said, handing me a sheet of paper. "I spoke to an associate of mine and he's made you that offer. It’s a prestigious position, high salary and unlimited potential for advancement. I believe it's exactly what you've been after?"

  I stared at the paper. Drake was telling the truth, it was a Fortune 500 company, with a phenomenal salary and profit sharing. "But Peter, this is one of your competitors."

  "Good," He said with a grin, "Your being there will keep me on my toes."

  I set the paper down. It was a dream offer, but my dreams were changing. "Peter, I thought I would work with you, keep learning at your side."

  "This is the same offer I've made every woman, and they've all accepted it. You see the third lesson is the most challenging, and if you fail you get nothing. I think you'd be a fool not to take this offer instead."

  I thought for a moment, "No, I want to take the final lesson if that means being at your side."

  "It's your decision Rebecca, I won't force you."

  But I'd made up my mind.

  Drake led me to a single post standing in the
corner. He leaned me against it, and placed straps across my chest and waist, securing them tightly. I was completely immobile, but my arms were free. Peter walked to a small table where a bottle of champagne and two glasses waited.

  "We're going to toast your success," He said, popping the cork, "Now hold your arms out, palms up."

  I held them out, forming a human t-shape. Drake poured two glasses of champagne, filling each to the brim. He set a glass on each of my upraised palms.

  "We'll toast your success, unless you spill a drop, at which point you get nothing."

  I stood there, balancing the two glasses, my hands already quivering. Drake undressed with his usual precision. Then he leaned forward, kissing me, our tongues locked together passionately. My hands trembled, but I didn't spill a drop. But he wasn't done. Slowly he kissed my neck, moving down my chest, his tongue lightly dabbing my red-hot skin. He reached my breasts and his tongue encircled my hard nipples. He took each one into his mouth, sucking them gingerly.

  My body shivered in delight, my hands trembled, but nothing spilled.

  Drake's kissing moved lower, down my belly, the tip of his tongue licking my naval. Oh god, is he going to eat my pussy? I wanted him to do it even if it meant losing everything. I wanted to feel his hot tongue on my hard clit.

  He got closer, running his tongue along my inner thighs. The sensation was delirious.

  But nothing spilled.

  Drake stopped for a moment, "I want you to confess something to me Rebecca. Why is it a woman who graduated at the top of her class was stuck in a low, entry level position?” His tongue came even closer to my pussy, "Confess your sin to me."

  And then he licked my pussy, running his tongue along my labia.

  I gasped, shivers racing through me, "I was arrested in college… I helped someone who was running a pyramid scheme. I didn't know what they were really up to, but the cops busted me anyway." A rush shot through me as Drake's tongue encircled my clit, "Because I had a criminal record no good firm would hire me… Oh God!"

  I was cumming, my toes were curling, my breath heaving. The combination of restraints, pressure, his expert pussy eating and the confession were intoxicating.

  But nothing spilled.

  Drake stopped his licking for a second, "I knew about the arrest, I just needed to hear you confess." And with that he dug in again, feasting on a banquet of my juices.

  I was cumming again. This was madness- every time I climaxed it placed my future at risk, but that only made it more exciting. "Oh god, Oh Peter please, it's fantastic." My hands trembled, every muscle and sinew straining to remain outstretched. I could feel myself building to another thundering orgasm. I couldn't hold the glasses up this time. I felt my arms shaking, weaker as I climaxed harder than ever before.

  My arms dropped… just as Peter plucked the glasses off of them.

  "You did it Rebecca, you passed all three lessons," He said, handing me a champagne glass.

  I struggled, finally raising my almost numb arm to accept it. We clicked glasses and sipped the cold champagne. Nothing had ever tasted so good.

  Drake kissed me deeply, the expensive champagne passing from mouth to mouth. He unstrapped my restraints and led me to couch. But this time we didn't sleep. He laid me down and climbed on top of me. There were no mind games and all traces of dominance were gone. My hands roamed down his body, past his solid chest and abdominals until I had his stiff cock in my hands. Our breath came in short gasps as he dug his face into my neck kissing me. I wrapped my legs around his back, guiding his cock towards my pussy.

  "I want you so badly," He moaned, "I held back before, but now I must have you."

  He pressed his hips forward, finding his way into my pussy. My back arched as he slid inside.

  "Oh god, that's so good," I panted.

  Within seconds our bodies were tightly entwined, hips thrusting back and forth in perfect rhythm. I was already cumming, the muscles in my pussy throbbing around his stiff manhood. Then his body tensed and his hips froze.

  "Oh yes!" He yelled, "I'm cumming Rebecca."

  My body responded in kind, hips pumping like a jackhammer to squeeze out every drop he had. Then he sank down, out of breath, kissing me gently. We lay there feeling warm and wonderful.

  I didn't wake up alone this time. Peter was still contentedly wrapped around me until my moving woke him.

  "That was amazing," He said, smiling. "Rebecca I want you to be at my side in business, and life."

  "What are you saying?"

  "Well, for years I've never had a relationship, certainly not one I acknowledged in public. I want you to be that. People will talk, and the press will write about it, so it won't be easy. Would you be willing to be my…"

  "Girlfriend?" I asked.

  "I suppose that's as good a term as any. I also want you to take the lead on this New England Tool Company takeover. It will be a good chance to use what you've learned. I have things to do tonight, otherwise I'd ask you to stay."

  "That's okay, there'll be plenty of nights."

  He walked over to the shelf of offerings and picked up my grandmother's vase, "You should take this back, consider it my first offering to you."

  He sat back down on the couch and gave me a kiss. We held it longer than expected… it turned out he wasn't in such a hurry after all.

  CHAPTER NINE

  A few hours later I was back at my apartment, placing the replica vase back on my mantle… next to the identical original. I was too exhausted to sit and ponder my future; all I knew is that I was free. I went to bed, knowing tomorrow would be a busy day.

  By 9:00AM the media was buzzing with news of Peter Drake's arrest on charges of larceny and stock fraud. The FBI refused to comment on the evidence, but promised it was quite damning.

  My little vase full of audio and video surveillance equipment had done its job well, recording all the details of Drake's vicious and totally illegal takeover of the New England Tool Company. He'd manipulated the stock prices with the intent to defraud… a major felony.

  David rang my buzzer a few minutes after nine. I had no choice but to let him in. After all you can't keep your FBI handler waiting. He'd been assigned to my case a year earlier when the FBI planted me in my old job as an informant.

  I hadn't been lying to Drake about my arrest, but I had left out one key detail. Like an idiot I mailed some documents for the pyramid scheme people and that instantly made me guilty of mail fraud… a very serious charge. I licked one forty-nine cent stamp and became Ma Barker overnight. I got probation for the pyramid scheme but the FBI left the mail fraud hanging over my head to get my cooperation. The feds placed me at my old job to look for evidence of illegal trading. But when Drake suddenly contacted me the feds were over the moon. They'd been trying to get evidence of Drake's illegal activities for years. The FBI's lab even created a replica of my grandmother's vase overnight, believing that Drake's people might be scoping out my apartment. It sounds paranoid but they were probably right.

  David came in, thrilled to have been part of a major bust. It was, in his words, a career maker.

  I only cared about one thing, "Does this mean I'm free?"

  "Probably," He said, "You did your job so any criminal record will be cleared and you can start over again. Of course you and I can still spend some time together," He added, putting his arm around me.

  I pushed him away, When he came on to me a year ago I didn't have a choice, but that had just changed, "Now that I'm an honest woman are you going to invite me over to meet your wife?"

  David looked angry, "You leave my wife out of this."

  "No, I want to leave me out of it! I couldn't say no to you before, but I'm a free woman now… so why don't you get out of my apartment and my life."

  "We'll see about that," David said, glaring at me, "Remember I'm the one who has the last word about your freedom!" He stormed out, slamming the door behind him.

  I had endured so much shit from David, so why couldn't he jus
t walk away and leave me alone?

  A few hours later the SEC received an anonymous email informing them that one of the agent's working on the Drake investigation had purchased stock in the New England Tool Company. He was using confidential information for personal gain, intending to dump the stock right before Drake tanked the company. It was unethical for an agent to do that… almost as unethical as forcing your informant to sleep with you. David's days with the FBI were numbered. I always knew David was corrupt, which is why I feed him so much confidential information. His own greed did the rest. I didn't do it out of vengeance for his taking advantage of me… I just wanted him to leave me alone.

  Around noon I placed a call to my grandmother. Being a newly retired woman she was almost always home.

  "Have you seen the news Rebecca?" She asked, excited, "That billionaire Peter Drake guy was planning to ruin the tool company. If the FBI hadn't caught him I would have lost my pension! It's a miracle!"

  "Well grandma," I said, "Sometimes miracles do happen."

  THE END

  Another New Holiday Billionaire

  Pamela Avery

  Copyright ©2016 by Pamela Avery. All rights reserved.

  No part of this book may be reproduced in any form or by any electronic of mechanical means, including information storage and retrieval systems, without written permission from the author, except for the use of brief quotations in a book review.

  CHAPTER ONE

  Caitríona Michaels snapped her pencil in two  actually snapped it in two equal halves as she glared across the large expanse of her office at the two junior executives shuffling their feet and staring, in obvious dismay, at the floor in front of her large desk. They reminded her of her little nieces, but she didn’t find them half as endearing.