The Gambler


What a vicious bastard, I thought. I can't let him whip her for a week because of something I did.

"OK," I said, defiantly. "Let's get this over with."

He smiled again and turned to the girl. "You got yourself a real champion here, Jess. Man's willing to put up a hundred thousand dollars to keep your pretty ass from a little punishment."

He was absolutely gleeful. "My name's Max, by the way, Max Springer," he said as he held out his hand. "...and this here is Jesse. I don't like to gamble with strangers."

"I'm Howard Lowe," I said, returning his handshake with a limp wrist. My face was ashen and despite my earlier resolve, I was afraid.

"Howard," he repeated, turning the name around scornfully in his mouth. Now, he was really enjoying himself. Then he pulled the Piranhas out of his pocket and held them up for both of us to see. "These little babies are amazing," he said, pushing on the side tabs and demonstrating the pinching movement of the inside points. "And the name really fits. They can really bite."

He slipped Jesse's dress down to her waist. She sat on the floor half naked, bound, and gagged. We both looked down at her from our plush seats. She starred back at us unashamed. Grabbing one of her breasts, Max held it tight as he pushed the Piranha over her nipple and slowly released the tabs. Jesse closed her eyes and absorbed the pain. I could see that it was a lot worse now since her nipples were already sore. Max would have known that.

He watched her anguished face for a moment and then did the same to her other breast. Pulling her dress back up, he muttered, "We'll leave that up. Don't want upset that stewardess, now do we?"

He whispered to the girl loudly enough for me to hear, "You'll be okay, Jesse. Just keep thinking about how much worse it will be when we get home. She held my eyes. I could see fear; this was no idle threat. The man really was a sadistic pig, just as she had said.

"I hate to see her cry," he said then he smiled.

That was when I lost my nerve. "Let me ask you a question," I said with a shaky voice. "Suppose I just buy out her contract. You said you were thinking about selling it anyway, this way we both end up with what we want." This wasn't true at all, I thought. All I wanted was my hundred thousand dollars safely back in my account and to be free of this mess.

He looked at me like the street fighter that he really was. "That might have been OK before, kid, but then you and Jess here went and made this personal. Personal is no good. This girl is my property. You fucked with her head without my permission. Now she's goin' have to pay for her mistake and yours too."

His arrogance put some steel in my back. I looked him in the eyes and even managed to exhibit a bit of bravado, "Well then, all that's left to do is cut the cards." It was all show; I was scared and I knew he was going to win.

Placing the cards down, he gestured with his hand for me to take my cut. I managed to nod in his direction—you first.

Smiling, he reached down and cut the deck—a Jack. He just smiled, leaned down, and showed the girl the card. Her eyes rolled and I thought she had fainted, but then her eyes opened and she looked at me. It was the look of someone condemned; I had sent her to Hell. "I'll charge up the whip's batteries as soon as we get home, Jess, so you can start your week right." He was enjoying every moment of this.

Then he looked over at me, "Your card, How-word."

I ignored his jibe, but my hand was shaking so badly that I had trouble cutting the deck. I didn't even look at the card I'd drawn, just faced it towards him. He looked down from my eyes to the cards, smiled broadly, and leaned back in his chair happy. I had lost!

I was devastated. Three year's savings gone in a second and a week of vindictive torture for a girl who had just asked me for a little help. Surprisingly, the money didn't seem all that important anymore as I thought about Jesse's beautiful body writhing at the end of this asshole's whip.

Oh man, what had I done? I felt sick.

Numb, I checked the card in my hand to see how close I had come. It was the queen of hearts. The queen of... THE QUEEN!

Max looked at me unfazed. "Looks like you won, Kid. Congratulations." He picked up the contract, wrote in my name as owner and signed it. Then he put it back in the bag and gestured for us to change seats. Once he was settled, he casually rolled over and went back to sleep. Gamblers don't linger at a losing table.

I was dumbfounded and sat there for some time enjoying the relief that coursed through my body. Then I remembered the girl and moved to her aid. I swore to myself that she would never suffer in my hands.

Reaching down, I removed her gag and then as gently as I could I took off the Piranhas and put them back in the bag. I tried not to touch her breasts, but of course that was unavoidable. She was crying softly. I wiped her face and untied her hands and ankles. Still crying a little she moved in between my feet and rested her head on my lap. I could feel her arm inching forward to find a secure place between legs. I pushed the hair out of her face and then got instantly hard when I saw her mouth so near my cock. She probably noticed, but I didn't care. We had won!

When we started to descend, she turned around and positioned herself for the belt. I put it back on and gently moved her halfway under the seat. Of course, I didn't use the hood.

Max, who had slept for most of the trip, finally woke up as we were landing and watched us with his now-famous smirk. When the plane arrived at the gate, he stood up and gave me a quick goodbye handshake. "You are the man, Howard," was all he said. Then he was gone.

At the time, I thought it was just a Max-like dumb thing to say. Later, I would regard those four words as precious wisdom ...most precious wisdom.


"May I change my clothes, Master?" she asked.

We were standing outside the arrival gate at JFK. With the sundress exposing her bare shoulders and long legs, she was getting lecherous stares from the male passersby. I was embarrassed. "Look, ah...Jesse, please don't call me that; my name is Howard. And you don't need my permission to change your clothes. That life is over for you. I'm a decent person, I don't treat women badly."

She looked at me with a strange expression. "Thank you, Ma... Thanks, Howard. There are some jeans and a top in this bag. Maybe I could wear them?"

"That would be fine," I said. She just stood there holding the bag. I was confused. "Go ahead," I urged.

She glanced at my shyly and said, "I'm not permitted to open it." It was ridiculous, but I guess once you've been whipped for something, you learn.

"Look, I said, you don't..." then I stopped, frustrated. This wasn't the place to have this conversation.

Bending down, I opened the bag and handed her a pair of jeans and a top. She walked off to the ladies room. In a few minutes she was back. I held my breath. She looked like a New York fashion model, totally unapproachable. I could see that people were still staring at us... at her. She was movie-star gorgeous.

Quickly, I steered us to a cab line and we jumped in. "Twenty-Eight East 79th Street," I said to the driver, then added a "please." He nodded and drove off. We sat in total silence for the entire trip, both of us overwhelmed by the events of the last few hours.

I live in a Manhattan townhouse. When we arrived, I saw that she was surprised. She had expected an apartment. I turned on some lights and directed her to the library and a wooden chair in front of my desk. I took the seat behind the desk.

"Let me explain a few things to you, Jesse. I was trying to be very businesslike. I'm not rich. This is my Grandfather's house; it's owned by a family trust. I have the right to use it, but not to sell or rent it. I also have a small trust that pays me a little allowance each month. That's all my Grandfather left me. In other word, I'm not rich." I paused and let her absorb what I'd just said. "Do you understand?" I didn't want her to think I was...a mark.

She nodded.

"I live here alone, by choice," I continued. Actually, the choice part wasn't really true. "I don't socialize much... too busy at work." ...this was getting too personal. "I just don't have that many relationships," I said, stupidly ending my clumsy explanation of why a 25 –year-old, townhouse-owning, reasonably good looking, tall, eligible man was living alone in Manhattan.

She nodded again, while she looked around the room and then asked the obvious question, "Are you gay?"

"No," I replied, a little hurt for some reason. I hurried on. "You can stay here while we take care of the legal work. There are plenty of extra bedrooms. Tomorrow, I'll call my lawyer and get him started on your emancipation."

"Emancipation?" she asked.

"Yes, emancipation. There's no way that I can hold on to your contract. I work in a bank, a vice president. It wouldn't look right. Not that I wouldn't want to be...associated with you, any man would, you're beautiful. It's just that in my position, with my would just be, well inappropriate. Even though what happened tonight was all innocent, it would be just too hard to explain. Don't worry; I'll make sure that you get paid the full amount agreed to in the contract."

She was quiet for a moment.

"I'm sorry about what I said before in the plane, Master ...ah, Howard," she was looking down. "The pain was getting to me. Thank you for your help in working things out with Mr. Springer. I know it's inappropriate to say such things, but he was an animal. It was a brave and generous thing to do."

We both knew that this little speech was bullshit—for the most part, I had let her down time after time—but it was easier for us to accept the picture the way she had just painted it. If I had just left it there, things would have worked out much differently, instead my mouth began again.

"I'm not sure how long the legal work will take, but if you're okay with it, we can just pretend that you're my live-in girlfriend for a few days. This way, when you leave, I can just say we broke up. As I said, I haven't had much time for girls, but people will accept this explanation. The last thing I want is for anyone to know that I owned a CELT contract. Even though I didn't do anything wrong, I don't want to have to explain this, ever." I paused again.

"Or, if you'd rather stay at a hotel, I can make a few calls and we can move you in tomorrow. You won't need to worry about the expenses; I'll pay for everything."

"In either case, I'll treat you with the utmost respect and, of course, there won't be any physical abuse. I find that reprehensible. Hopefully, Max is the last man who will ever... Anyway, for all practical purpose, we can consider your CELT contract ended right now. You are my guest."

I smiled in what must have looked like a self-righteous way and sat back in the chair. She looked at me with a strange expression and in a matter-of-fact tone said, "Won't we need to fuck, Howard, if we're going to be boyfriend and girlfriend?" Was there a hint of sarcasm in her voice?

Her directness surprised me, and I needed a moment to recover. Don't forget, I told myself, she's little more than a street whore even though she looks like a model.

"No, we don't need to do that, Jesse," I said slowly, thinking that she may be relating to this kind of decent treatment after what she'd been through. I also had the idea that she might not be that bright. "We're only going to act like lovers, but in truth we'll just be employer and employee. You're an escort, remember? Someone people hire because they don't want to go places alone." We both knew that that was also bullshit; CELT escorts were sex-partners, mistresses.

"Do you understand what I've told you?" It was almost the tone one would use with a child. Maybe she was stupid?

"Yes I understand, Howard," she began with equal patience. "It's just that people always seem to know when a couple is fucking... someone might suspect something. Maybe you should think about it; fucking me might actually be the safest thing, reputation-wise." She was copying my parent-child tone; she also sounded a little angry. Why?

"And when you say, 'no physical abuse' though," she continued, "you mean, unless I deserve it, right? It wouldn't make sense for you to allow me to go without any discipline. Didn't you and Max agree that the best way to handle one of us was to, and I quote, "put them up by their wrists and get them on their toes....shove in a good gag and you're in for some real fun. This one...will kick and jerk for half-an-hour..." You seemed to be listening very hard. Oh, and I almost forgot his most important suggestion, 'fuck her while her brain is still sparking.' Isn't that what you and he agreed?" She was definitely angry now. This was not going at all the way I expected.

"Look Jesse, I don't think you understand..." I started again.

"...and by the way, Howard," she interrupted; "I fast-tracked my way through high-school and college, graduating from NYU at 20 with a bachelor's degree in psychology. So, don't keep asking me if I understanding you. I said my family was in trouble, I didn't say that I'd been poor and dumb all my life."

"Let's be honest with each other," she continued, clearly angry now. "You didn't have the nerve to help me when I needed you, but now I'm supposed to believe that you're going to do the right thing for the sake of your reputation ...your family; you're going to throw away a hundred thousand bucks."

"And what makes you think I want to be emancipated?" she asked. "Don't you think the next man who buys my contract is going to wonder why I was set free early? Are you going to give him an affidavit attesting to your good will? CELTs are worth a lot, people don't just give them away without a good reason."

"You didn't act out of honor or sympathy, Howard; you were distracted by that bulge in your pants and acted impulsively. It's that simple. Once you had backed yourself into a corner, you just followed the path of least resistance. It was all an accident that worked out okay for you. Once you have had some time to think it over, you'll come to your senses about me." She was calming down.

"It's not that I don't appreciate what you did, Howard. Some of it truly was brave and Max really was a pig." She paused and looked at me.

"Take my advice," she leaned forward as if to emphasize her next words. "Tie me up and hurt me a little over the next few days...just so you can see what its like. I'm sure you'll like it. If you want, you can fuck me as well or I can suck your cock. Then, when you've had your fill, sell my contract. That's what most men in your position would do. Believe me, I know. You won yourself a contract-girl worth a hundred thousand dollars tonight, Howard, enjoy her. As for the contract itself, I agree that it would be impossible for you to hold on to it, someone of your standing, but don't give it away."

She leaned back and smiled at me with a now-doesn't-this-make-sense expression.

I was hurt. I guess I had started to think of "us" as a team. She was right to set things straight. I would never hurt her, of course, and there was no way that I would force her to do anything sexual, but she was right about the money. Holy shit, in the last few hours I had doubled my net worth. Tripled it really if you adjusted for the taxes I didn't need to pay. (I knew that Max wasn't going to claim any of this on his taxes.)

I was also extremely tired. "I'm not exactly sure why I did any of the things I did tonight, Jesse, but I'm not the kind of man who would take advantage of such a situation." Let me take you to your room," I said this last with finality. "We'll straighten all of this out tomorrow."

I left the house the next morning early, before she was awake. I wrote her a brief note saying that she should make herself at home and that if she wanted, we could go to dinner that evening and talk. I also left her some cash to do some shopping. (She didn't seem to have many clothes.)

I put the evening's discussion to the back of my mind. She had been tired and stressed. I should have waited to talk to her. She seemed like a decent person in a bad situation. We would get it all worked out tonight. In the meantime, I'd get things started by talking to my lawyer about her contract. Once she really understood the kind of person I was, it would be easier for us to talk.

The office was in chaos over something or other and I was in meetings for the entire day. It was a blessing in a way to be distracted from the "Jesse problem." Unfortunately, I didn't get a chance to calling my lawyer.


That evening when I got home, she met me at the door dressed in black pants and a white silk top. The pants hugged her behind, highlighting her long legs. The outfit included a short jacket that made her small waist look tiny. She was a classy dream... a Park Avenue debutant... no one would ever guess that she was a CELT.

"Is this okay, Howard?" she asked innocently.

"It's perfect," I replied enthusiastically. My relief was enormous. I wanted to kiss her and more, but held back. We hardly knew each other.

She waited and then leaned over and kissed me on the cheek. "Thank you, again," she said. Then she began to describe her day as we walked to my bedroom. She was effervescent, bubbling over with enthusiasm, talking lightly all the way to my door where she waited modestly while I got dressed.

Being in New York City with time and money was an exciting experience, especially for a stunningly beautiful young girl. I knew that she would have been propositioned at least half-a-dozen times. In fact, a part of me thought that she might be gone when I got home, contract or not.

For the next hour we talked continuously without saying anything important. I forgot that she was a professional escort and despite my clumsiness around women, I felt a real rapport growing between us. She made everything easy and fun and there was no mention of yesterday's events or the prior evening's discussion. It was as if we were old friends.

Dinner was even better. We talked about everything and nothing; it was a real date. It turned out that she was 22, three years younger than me. Her family was from California with Russian roots. She had originally come to New York to get the East Coast educational experience. It was fun to talk about the stuff we'd done in college, and to exchange opinions on just about everything. She was incredibly sharp and smart, much smarter than I had imagined. For the first time in a long time, I was having fun.

Later, over coffee we discussed her "situation." She was open and unembarrassed. After college, she had been looking for a job when her father had been accused of embezzlement. Between the legal fees and fines, the family, which had been reasonably well off, lost almost everything. He went to prison for eight years. Two month's later her brother was diagnosed with cancer. The treatments needed to keep him alive were costly. She tried everything, but the only way she could get enough money for him was to become a CELT. Even then, the non-transferable contracts didn't pay enough, so she needed to agree to the more lucrative transfer clause. Such a contract had come easily with her looks.

The only sad moment in our conversation was when she talked about her mother and brother, who she had not seen for two years. Apparently, both had naturally fought her decision to become a CELT, calling his illness "God's will." When she refused to listen, they broke all contact with her. Her money was now funneled to them through a charitable foundation which, on her strict orders, took full credit for the charity. There was no bitterness in the explanation. "Just my bad luck," she said with a sad smile.

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