Whatever It Takes Pt. 05 - Late Night Tuesday

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Elaine learns how to maximize her earnings as a whore.
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Part 5 of the 8 part series

Updated 06/09/2023
Created 02/10/2019
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This is another part to the story of a beautiful American businesswoman (Elaine) who comes to Jamaica to relax and eventually ends up working in an island whorehouse to pay off a debt. The story began when her husband, Paul, and she arrived on a weekend to relax and enjoy time together before Paul left on a business trip that will require him to spend several days visiting other Caribbean islands. While he was gone, Elaine intended to relax and enjoy the sea, sun, and surf at their resort. She had not intended to leave the security of the resort and be exposed to the violent crime and brutal treatment of women for which the island of Jamaica is known.

However, on Monday (Pt. 02) she had been duped into leaving the resort. Then she had been drugged and gang raped, as well as publically and sexually humiliated in front of several prominent native island residents. To make matters infinitely worse, she had been photographed and videoed during the series of rapes and humiliations.

Elaine has learned (Pt. 04) that she has pay in cash and "services" to recover those photographs and videos. There is a time constraint imposed on the payment process since it must be completed prior to her husband returning to Jamaica. Otherwise her secure life as a banker, new-mother, and wife could end abruptly, if and when, the high resolution digital images of the acts she performed were distributed to her husband, family, and employer.

The prior episode ended with Elaine reconciled to working as a whore completed her first paid session with a client. The experience was degrading, but she remains committed to doing whatever it takes to pay of her "debt" and recover the incriminating images of her having sex with multiple partners while under the influence of alcohol and drugs.

To date, the major characters in this story are the following:

  1. Elaine Farrell - the gorgeous, busty American business woman who is the central focus of the story (for details on Elaine read Pt. 01); she intends to do whatever it takes to survive;

  1. Paul Farrell - Elaine's husband who is a brilliant, well-compensated engineer who is currently on business visiting other islands;

  1. Michael - a rapist and recruiter for a premier set of island whorehouses who delighted in humiliating and sexually abusing Elaine;

  1. Patrick - Michael's employer and a major local criminal with links to American enterprises, both legal and illegal;

  1. Mack - a bartender at the resort who works for Patrick, assisted to drug Elaine, and participated in her rapes;

  1. Heather MacDonald - a friend to Elaine and Paul who appears to be a vapid beach bunny but is in reality a tough ex-marine who is investigating financial irregularities at the resort where Elaine and Paul are staying; currently in Miami reporting to her father who is the principal owner of that resort;

  1. Jessie McKinnon - an American whore working her trade in Jamaica assigned by Patrick as Elaine's mentor with the duty to integrate Elaine as fast as possible into the cash generation process of fucking and sucking for money; Jessie despises Elaine, correctly believing that Elaine holds Jessie and her profession as a whore in contempt;

  1. Randy - the manager of the whorehouse who works for Patrick; negotiates prices with clients, collects money, and tracks the amount of credits that Elaine earns; regards Elaine as an asset and acts to maximize the return on that asset;

  1. Jason - controls the whores through intimidation and violence when required; also ensures that the johns do not damage the whores whose services the organization sell; and

  1. Danelle Accardi - also a 'workout girl' trapped into working as a whore at The Dolls' House; Ph.d. on the faculty of the University of Virginia; maybe a friend to watch Elaine's back, and then again maybe not...

WHATEVER IT TAKES:

WORKING OUT A DEBT IN JAMAICA

LATE NIGHT TUESDAY

We Gotta Get Out Of This Place

...My little girl, you're so young and pretty

And one thing I know is true

You're gonna die before your time is due...

We gotta get out of this place

If it's the last thing we ever do

We gotta get out of this place

Girl, there's a better place for me and you...

Written by Barry Mann and Cynthia Weil; recorded and popularized by the rock group The Animals

LATE NIGHT TUESDAY - The story continues...

I went down to the "reception area" and turned in the green ticket to Randy. He took it and winked at me. I asked for and got two fingers of Jack Daniels, and waited for my next trick. Lots of trade moved, and I began to realize that I was competing with younger and prettier girls - less educated but education meant nothing here. It was all about tits, ass, cunt, and making men willing to pay to fuck you-a distortion of what they taught in business school about marketing and selling.

The night began to move faster. More men showed up, and the number of whores on the floor decreased as more of them were 'engaged' upstairs. I was a part of this great game now - engaged in advertising and selling my body followed by delivering sexual services for pay to complete strangers who expect to cum in me and on me as a fair exchange for what they paid.

I sat there for a while. I did not project sexuality the way the other whores did. I was at a disadvantage in my new trade. I would have to learn on the job or I would be here for weeks. Time was against me. I had to get back to the hotel in less than three days so that my husband would never know what happened.

Jamaica was a black island, but only about 40% of the men that came to the house were black. White men - expatriates, pilots, tourists, and diplomats - all came for a quick fuck. I guessed most were married but bored with their wives or just horny away from home.

My second trick wanted a basic blow job and handed me a pink ticket to show me he paid. He was an older local Jamaican businessman who told me that his wife refused to suck his dick. So once a month he came here and liked to have the North Americans who were working off their "debts" to Patrick give him a blow job.

My experience with oral sex was limited. Although Michael had raped me orally yesterday, the only man with whom I had even experimented with oral sex was my husband, Paul. Every once in a while, when we were really drunk and/or horny, I had kissed him there several times. The only time we really did it was on our first anniversary when I kidded around and put it in my mouth. It did not turn out well. Paul twined his fingers in my hair and pressed my head down. I gagged when his penis hit the back of my throat. When I instinctively tried to pull back, his grip became unyielding, his fingers digging into my scalp. I felt as if I was suffocating and gave out a muffled cry of distress. I could smell his semen and panic rose like a tidal wave in my mind. With great effort I pulled my head up, partially aided by him easing the pressure on my head as he realized that I was not kidding. It got worse. I didn't know then how close he was to cuming. As I pulled my face up, he shot his load - some on my chin, and a lot on my breasts. As I wiped it off my face with the back of my hand and saw the rest on my breasts, I felt dirty. I was angry at him for being selfish and trying to force me to go somewhere sexually that I did not want to go. As husbands and wives do to avoid an argument, we laughed about it and did it only rarely, usually on his birthday.

However, two days ago on Sunday my new found girl buddy, Heather MacDonald, gave both Paul and me a lesson in how to give a world class blow job. She demonstrated all the tools necessary for giving memorable fellatio including lubricant (minimize friction), a scrunchie to keep a woman's hair out of the way, and breath mints to avoid cum breath for the rest of the day. We did have a good time giving a two-girl blow job to Paul who greatly appreciated the opportunity to serve as an instructional aid for Heather's demonstration. Despite my current situation, I smiled when an image of her pontificating to Paul and me that a male wanted a warm flesh tunnel of a woman's throat, mouth, and hand on his dick.

As the black man and I walked from my table, Jessie called me over to her.. When I got there, she reached up behind my neck and pulled my face down to hers. In a stage whisper heard by everyone in ten feet of us, she said, "Miss Pure, here's a tip for you. The most sensitive part of a man's cock is the underside, just behind the tip. If you rub it with your tongue while you suck it, it'll drive men crazy. They'll blow their load in a hurry so you can move on to another trick." With that she laughed, turned to her fellow professionals at the table and pantomimed sucking a penis, complete with her tongue waving in the air. I pulled away from her and continued the trek to my room. The old man, my "client", moved energetically, never taking his eyes off my ass as we ascended the stairs.

Trick #2 - Tuesday evening 22:30-22:50 credit earned: $50 + $50 tip = $100; cumulative $200; to go $9,800

The old guy watched me bemused as I struggled out of the shirtdress, bra, and panties. It seemed silly to disrobe in front of a trick who only wanted that for which he paid. The process of taking off one's underwear was kind of a special thing between lovers. All this man wanted was my mouth on his dick so he could dump a load of cum into my belly. There was no finesse or style required...strip, open mouth, lick, suck, swallow - all in a night's work here at the Dolls' House.

But I was wrong about him wanting to get down to business quickly. After I cleaned his dick, he lay with his back to the head of the bed. I was naked. When he was comfortable, he asked me to stand across the room with my back to the balcony door. He stared at my breasts and my waxed, nearly naked crotch.

"Why do you want me over here?" I asked.

He answered, "Now get on your hands and knees and crawl to me. On the way just keep telling me how much you want my cock in your mouth. Lick your lips as well. Make it special for us."

His use of the word "us" made me want to throw up. But instead I told him, "If you want to play fantasy games, it will cost you an additional $50."

"Fine with me. But make it good. I want to see submission by you tom...white to black, female to male. I am believe this is as it should be and is not 'fantasy'."

Slowly I crawled across the room, all the time pleading that "I wanted his big, black cock" and "please let me suck it." I smiled and debased myself all across the room. When I got to the bed,

I crawled naked between his legs and moved my head towards him. The whole thing revolted me, but I was determined to survive and regain my security and stature as a middle class, American, professional woman. I stuck my tongue out and licked the end of his black dick. The head flared and turned a darker color. I kept licking it with my tongue, coating his dick with my saliva. I could see the veins in it pulsating. I licked down the side to his heavy, black balls. I half hoped the oral stimulation would be enough, and I could make him cum without taking him in my mouth so I kept on licking. I ran my right hand up and down his fuck toy while lashing the purple head with my tongue.

He pushed my hair back so he could see my tits and tongue on his dick. He told me to "put it in your mouth...now." I had stalled as long as I could. I encircled the base of his penis with my left hand while using my right to gently stroke his black balls. For a moment, I contemplated biting down with all my might on the invading organ. Then I realized what a futile gesture that would be. This man thought I was a whore and only wanted what a whore was paid to give. Why hurt someone who did not understand that I was not there voluntarily. This was not my job, but it was my problem. In any case, pain I inflicted upon him would be repaid ten times over by me when Jason took revenge.

I did as I was told. I walked my tongue up his prick, and, when I reached the top of it, I opened my mouth reluctantly to take him inside. I ran my tongue circularly around the tip of it, spiraling it down the length of this cock until he was fully held by my tongue, lips, and the soft, wet walls of my mouth. Then I began to suck, moving my head up and down as I did, so as to bring him quickly to orgasm. He moaned with deep satisfaction and clutched my hair with his hands, moving my head up and down on his cock to the rhythm that he wanted. But his was a light touch, only guiding me. What I was doing, I was doing. There was no force. I could have stopped, but I couldn't have stopped due to the need to end this experience without being maimed.

He was solid as a rock now, his prick fully extended and straining. I was anxious to bring him off. I continued to suck, moving my head in response to his pressure on my hair, like a dog on a leash. I also ran my left hand up and down his prick as I sucked at the tip. Anything to accelerate the process of his release, even if it was in my mouth.

Up and down my head moved, I fondled his balls with my right hand as my mouth worked on his shaft. He was helping now, shifting his pelvis up and down to match the action of my mouth. I lashed his piss hole with my tongue on each up-stroke. I realized that the more I cooperated, the faster it would be over.

When things began to slow down, I heard him say, "Suck harder. Suck!!"

I drove my mouth down hard and began to choke. He was in my mouth and in my throat. Trying hard not to panic, I forced myself to breathe during the few seconds when he withdrew for the next thrust, desperately trying to suck air to my tortured lungs around his cock which never withdrew completely from my mouth. His cock glided over my tongue to hit the entrance to my throat before partially withdrawing to repeat the process again and again. My jaws were stretched to the limit to accommodate his dick. I was gagging involuntarily each time his cockhead forced its way to my throat. He began to move his hips and rotate his prick in small circles. I kept sucking, praying for it to end.

I sucked and sucked, even looking into his eyes while I was blowing him, using that as a turn-on. My jaw was aching, and I was getting desperate when he finally let out a long groan and began to hump my face in little short jerky moves. He moaned again and I felt his cock jerk in my mouth. Suddenly I was flooded with a jet of cum that splattered against the back of my throat. Finally, his hips began to buck, I locked my mouth on him, and he continued to ejaculate with some cum leaking out of my mouth onto the sheets.

I held most of his cum in my mouth and moved to get off the bed; I intended to go to the bathroom and spit it out. Surprisingly, he moved quickly for an older man. He grabbed my shoulder and held me on the bed.

"Swallow it," was all he said. When I hesitated with my mouth still full of his cum, he put his right hand on my throat and began to stroke it. Again he said, "Swallow it." Then he tightened his grip on my throat - the threat was implied. His left hand reached out, caressed my right breast, and then squeezed it painfully. We were a frozen tableaux - his cum in my mouth, his hand on my breast, both naked. When he pinched my nipple, it was so hard that it fired off nerves in little white sparkles all the way up to my neck. Now I knew that I had no choice. I swallowed his cum - the taste not really registering as he felt my throat muscles go through the swallowing motions.

"An black man like me gets a real thrill from seeing a young gorgeous rich American blonde like yourself swallowing my cum. It kind of makes my day and is as it should be. Now thank me for the privilege of sucking my black love rod."

His comment crystalized for me that this was not about sex but about power - the power that these tricks had over the workout girls. There was also elements of racism, class politics, and anti-Americanism all wrapped into the humiliation imposed by him on me. The last thing that really counted here was sex as sex versus sex as a means of domination.

Submissively, I said, "Thank you for allowing me to suck that black love muscle of yours. It was one of the largest that I have ever seen. I loved the taste of your cum."

He got off the bed to dress. I lay on my back on the bed staring at the ceiling, waiting for him to leave. As he began to exit, he ran his hand gently from my pubis to my left breast and said "thanks" before he walked out. I showered and used antiseptic mouth wash that was conveniently on the shelf in the bathroom.

The dreaded knock came, and I headed back to reception. My body and I had generated only $200 in two hours. I was too tired to run the numbers, but instinctively I knew that my pace was too slow. I had to fuck and suck harder, make the clients cum faster, and take on more highly compensated assignments like doubles and triples. I was a survivor and a competitor. I knew I could do whatever it takes to get out of this place before my husband came back to Jamaica. I had the rest of this night and three days (Wednesday, Thursday, and Friday) to pay off my debt.

Back to the reception area I went. As I entered, I heard Jessie yell across the room.

"Did you remember to brush your teeth and use the mouth wash?" Everyone laughed at my expense. I tried to avoid meeting the eyes of anyone in the room, including and especially Jessie.

I turned in my ticket and began to work on another two fingers of bourbon. I felt a real need for the alcohol. Somehow, it made it easier to perform and to forget. I asked for another drink. The bar tender said that was my limit because Patrick had passed the word that he wanted me to "perform" at my best and to "remember my first night" - as if I could ever forget this nightmare. The bartender added that I had to "hustle" against the younger competition and liquor would slow me down.

I took my usual seat at the same table for two. A red haired American came downstairs and sat with me. This girl looked like she was going for a workout in a yuppie gym in the suburbs. She wore a short white cotton cut off jersey, no bra, nipples visible, bare midriff with a pair of short shorts that tied in front and looked sexy and functional for a whore - easy on and off. She was tall - probably 5'10" or 5'11" - all legs with small boobs, maybe 34B/C-24-35 overall. But the red hair was what was distinctive; she was gorgeous, sort like a Playboy centerfold. She also looked like she was in shape - the kind of tomboy that was always playing beach volleyball with the boys.

She said that Jessie had pointed me out as a workout girl. Her name was Danelle Accardi from Mobile, Alabama. She was also a workout girl - but a smart one - Tulane University with a double major, Psych and Sociology, and a Ph.d. in Cultural Anthropology from Cornell. She was currently on the faculty of the University of Virginia and had come to Jamaica on a summer grant to do research, something to do with the long term effects of slavery on an island culture.

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