Whatever It Takes Pt. 06 - Wednesday

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Elaine's first full working day "servicing" clients.
17.7k words
4.47
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Part 6 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 (Pt. 01) 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 (Pt, 05) ended with Elaine reconciled to working as a whore and delivering multiple paid client "service sessions" that included the full range of oral, anal, and vaginal sex. The experiences were 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. Her total debt amounts to $10,000. At the end of her first working day on Tuesday, she had accumulated credits of $980 and still had to work off the remaining $9080 over Wednesday, Thursday, and Friday.

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 and protect herself and her family;;
  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; he enjoys taunting Elaine while he fucks her;
  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 prostitute working her trade in Jamaica and 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 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 intends to maximize the return on that asset;
  1. Jason (nicknamed "Animal")- 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 -

WEDNESDAY MORNING

A Girl's Gotta Do (What a Girl's Gotta Do)

...A girl's gotta do,

what a girl's gotta do.

Too bad I gotta do it

With someone new.

But a girl's gotta do,

What a girl's gotta do.....

Written by Rick Bowles and Robert Byrne; recorded and popularized by the American country singer Mindy McCready

WEDNESDAY MORNING -- The Story Continues.....

I never dream but here in this Jamaican whorehouse "never" has become its opposite -- now I dream every night. The dreams come into sharp focus suddenly and always involve the sexual slavery into which I have been forced to descend. Even in sleep, I cannot escape incessant penetrations, violations, and humiliations. The differences between the dreams and the reality is that in the former I am usually fucked by men that I know and in the latter by strangers. I do not know which is worse.

The dream opened with me in the "reception room" of the Dolls' House. I was standing at the bar with my usual two fingers of Jack Daniels. The music was the repetitive, thumping beat favored by disc jockeys in clubs all across the US. I wore a transparent, sexy, sheer black sleepshirt that buttoned down the front and dropped half way down my thighs. It hung loose on me with only one of the buttons buttoned. The effect was to draw attention to my breasts since the garment was unbuttoned above and below my bust. I sported no bra so that my dark red, erect nipples were prominently displayed through the gossamer nightshirt. To complete the outfit I had donned a black lace G-string thong bikini and stood on four-inch heels. It was an outfit that roared 'Come and fuck me!'

As the music built in volume, two women appeared on a stage at the rear of the room. The stage had two stripper poles, space for girls to maneuver around, and one queen-size bed One of the women was Jessie, the other looked like one of the "girls" that sat with Jessie in the bar last night. They wore nothing but red thongs which quickly came off as they assumed the classic 69 position on the bed -- Jessie on top with her face buried in the crotch of her companion with the other woman assuming a mirror-like position with her mouth locked on Jessie's crotch. The audience hooted and hollered.

After a bit more kissing and breast-rubbing, the performers were joined by four muscular men in nothing but T-shirts. One of them was Michael; I recognized the others as men who raped me on Monday evening at Patrick's party. The men stroked their cocks, looking like weapons pointed at the women who feigned indignation at being interrupted in their lesbo activities. Each woman was then "grabbed" by two men, pulled off their female partner, and forced into the doggie position. Within seconds, each of the women was penetrated, vaginally and orally -- one man in front and the other behind. Six people on the bed -- sweating, grunting, and rutting. Rather than recoil, the women appeared to be enjoying it if their moans, groans, pants, and gasps were to be believed. But somehow I was not convinced. It was too orchestrated; the looks in the women's eyes too vacant, too I-am-not-really-here.

But the crowd loved watching the sex show, and the whores worked the crowd, giving blow jobs and soliciting trips upstairs. The show successively raised the sexual intensity in the room and generated erections that would end up in mouths, cunts, and/or ass holes of the whores working the crowd.

I remember being mesmerized by the scene before me, horrified that this is what I am being paid to do. I would have to do all the things that the women on stage were doing and pretend to enjoy it, just like they were. On the other hand, I knew that I had to fuck and suck enough men to generate another $9,000+ in credits. I would have to do what I had to do to hit that target.

"Hey, Rich Bitch, you are not looking too good anymore." The voice of Mack, the bartender who assisted to recruit me into this mess, broke through my reverie, and I turned to look at him. In the mirror, I caught an image of my face, on the right side of which there was a Lang slash from my below my eye to my top lip.

I stared and stared, not able to tear my eyes away from the horrible vision that was me. I thought it was a dream. It was wasn't it? This really had not happened to me, had it? I cooperated, didn't I? Everything was all right, wasn't it? Was I alive or dead or neither? What was going on? I had difficulty breathing.

My mind was frozen in panic when all of a sudden when someone grabbed my arm and pulled me from my bar stool. I turned around to see Patrick.

"Get off your ass and fuck somebody. I got plans for you! I can't use you on stage. You are too old and too ugly, but you got two big tits, a blonde pussy, and half a face. I got customers back here that need to be satisfied, and that is your job."

Then, in my head as if from a great distance, I heard the chant from my dream the night before:

"One, two, three, four,

Let's fuck the dirty whore.

Five, six, seven, eight,

What a nice slutty date."

He laughed crudely and led me to a small room off the main bar. The only furnishing was a mattress on the floor next to the wall. He threw me down on to the mattress. Patrick then grabbed my right ankle and put it in a clamp above the ankle the clamp was at the end of a six foot chain that attached about to the wall about 12 inches above the mattress. One leg and both arms were left free. The mattress was filthy. I noticed a huge stain in the middle and recoiled. Before I had time to think about the stain, Patrick came back with a man that I knew, or thought that I did.

"Your first client, Elaine. He is an old friend, and you had better be nice to him. You only have half a face left -- and you'll lose that if the customers are not satisfied."

A tall handsome man looked down at me. His name was Louis Kenna. He was a vice president at the bank; I reported to him. I considered him a mentor and a friend. He stared at my body but refused to look at my slashed face.. Suddenly, he bend over me and grabbed the front of my blouse, with incredible force he pulled it apart with two hands, leaving my breasts exposed. As he stripped, he grinned a maniacal grin at me. His dick was hard and stood straight out.

"Louis, why are you doing this? Stop! We are friends."

"You don't get it, do you? Every guy at the bank wants to fuck you, and you prance around with those big tits like you are oblivious. Do you think that your career is moving ahead based on brains? Stupid Bitch! It is your tits and ass that got you where you are. Now I want to collect my reward for mentoring you for the last two years."

I tried to hold my legs together, pathetically covering my breasts with my hands. Louis shouted to Patrick, who in a rage raced over to the mattress with a white bamboo cane. H reached down, grabbed away one of my hands, and lashed the cane across my breasts I screamed in agony, like a wild animal caught in a trap. But I knew that the force of the lash could have been much more. He was scaring me not trying to really hurt me. I got that and knew that talking was over and fucking had to start.

Louis grinned as I lay there sobbing. Next he pulled my panties down and stared mindlessly when my crotch came into view. Louis grabbed my unchained leg and pushed it toward the edge of the mattress as he rushed into position between my legs.

I felt his penis enter me immediately, no warning, no lubrication. Dry, it plunged right inside me and started to thrust. He was rough, like an animal. He wanted his satisfaction immediately, as if he had been waiting a very long time. He pounded my body so hard into the mattress that I could feel the floor underneath. He was fast, hard, and rough. I lay there, my body bouncing with his thrusts, my legs moving due to him not to anything I consciously did.

"One, two, three, four,

Fuck her front and back doors.

Five, six, seven, eight,

She deserves her filthy fate."

My vagina burned with irritation, the pain intense. My body tried to defend itself by tensing up every muscle in an attempt to escape the bodily invasion. The chain on my leg kept me in place as he pounded away. His prick was scraping my insides. Then I felt the spasms of his cock as he began to ejaculate inside me. With horror and relief all mixed together, I lay there feeling his cum seep out of my cunt adding to the stain on the mattress. Louis continued to move inside me for a moment, and I thought he was trying to go again. But he was just squeezing out every last drop. He quickly withdrew and was gone from the room like it never happened. The event had not lasted ten minutes from entry to exit, and Louis had never looked into my face. He had just put his dirty meat inside me, on a filthy mattress, and used my hole until he came. He wanted to humiliate and fuck me, and he accomplished both. Louis dressed quickly and left me lying there wide open and leaking cum.

Patrick appeared, "Whore, put more into it with the next guy, okay? Elaine just relax and enjoy or it -- or act like you enjoy it. I don't give a shit which, got it? You are going to do this 30 or 40 times a day, every day that you work for me. You hear me?" For emphasis, he wacked the mattress with his cane.

"I don't want to hurt you no more than I must. You do it the nice way, my way. If you don't, maybe we slash your other check then tie your legs wide open -- maybe 80 or 100 men a day use your cunt you decide, OK? Fuck like a good whore, or be fucked to death. Your choice!"

I lay whimpering on the mattress as tears ran down my face. "Okay, okay," was all I could say, nodding to Patrick as he stood god-like above me.

The next man was there in a flash. As he swaggered towards me, grinning from ear to ear, I recognized him also. He was my first college 'love'. Johnny Houser, now a lawyer with some well-known firm in Chicago. We were even Facebook friends, exchanging photos of spouses and kids. He was wearing a three piece $1500 suit; his wing tips glistened as he walked.

I learned my lesson well. I opened my legs wide this time. He just smiled looked down at me and undid his belt. First the pants were neatly folded and put on the corner of the mattress. Then his underpants were put on top of the pants, very neat and precise, just the way I remembered him.

Naked from the waist down, he signaled what he wanted by ordering me to crawl over to him and get up on my knees. Again I heard those rhythmic words:

"One, two, three, four,

Let's fuck the dirty whore.

Five, six, seven, eight,

She deserves her filthy fate."

"Elaine, you know what I want. Just like the old days, but now you want it just like I do."

What he wanted was oral sex. When we dated, we rarely had occasional quick, sloppy intercourse, and I would never give him a blow job -- an occasional him-on-top straight fuck, but never in my mouth. Out of the past came the memory of a fight we had over this subject, with me walking out of his dorm room, slamming the door, and shouting over my shoulder, "in your dreams, ass hole!" Now he was in my dream -- or I in his -- and he would get what I had denied him ten years ago.

I capitulated without resistance. I opened my mouth wide. He did not move. "Come and get it, Elaine." Pathetically, I stretched against the chain, my mouth puckered and searching for him. I used my lips to pull him into my mouth. He laughed and moved his hips slightly, signaling me to get on with it.

I could see his veins bulging out, all the blood in his body must have been shifted to his dick from his brain. He was uncircumcised so the crown looked huge with only one eye from a distance of six inches. I moved forward and used my tongue to lick the end. The helmet head flared, and turned a still darker crimson. Slowly, I inched forward and, opening my mouth wide, guided his prick between my lips until I could suck on the head. I felt it growing rapidly in my warm mouth, swelling and extending. Using my lips, I gobbled all the way down the shaft until my nose was buried in his public hair.

"That's it, Elaine," John said. "Suck it for me just like you should have ten years ago. Use your tongue."

I wrapped my right hand around the shaft. While I continued to suck and lick the head, I stroked his cock with my fist. I looked up above the suit and tie and saw his head loll back, mouth open, eyes locked on the point where his dick entered my mouth. He was fully extended and straining. I began to work on him, giving him the best blow job I could, using my newly learned oral skills. I wanted to get it over with as soon as possible. Borrowing a technique I saw used in a frat house party porn flick, I began to moan in my throat and plunge my head back and forth, continuing to pump his dick with my hand while I kissed and liked his balls.

He was helping now, shifting his pelvis back and forth to slide his prick through my grip and in and out of my sucking mouth. "Why did you make me wait?" I grabbed the shaft as tightly as I could, letting it slip through my fingers on the lubricating I was applying with my lips and tongue. I lashed my tongue back and forth each time his engorged tip poked through my tight grasp and in to my mouth.

"Stop. Let me recover. We do not want to rush this, do we? I have waited so long! Now press your lips together but leave enough distance so I can slide my dick into your mouth. Put pressure on my dick with you lips as I move in and out. Do not use your hands at all. Now do it."

Anxious to end the rape of my mouth, I nodded, took my hand off him, and pursed my lips. He drove forward into my mouth and drove it to the entrance to my throat. I avoided gagging as he withdrew through my pressing lips. Then he rubbed his slimy prick on my face.

"So good, Elaine. You are a whore for real now. Now keep your mouth hole tight on the way in and the way out. Let's do it again."

He put his cock against my lips, inserting only the head around which I pressed tight with my lips. Then he slowly pushed himself into my mouth. I avoided gagging as he reached the entrance to my throat. He sawed it in-and-out several times, then again pulled it free.

"Sweet. You have a honey mouth. Again."

This time he rammed his dick into my mouth with more urgency. The in-and-out sped up as he moved closer to cumming. But again he stopped to rub his joy toy covered with my saliva and his pre-cum all over my face.

The he grabbed my hair and pulled my face back so that I was staring at the ceiling. He moved forward so that he towered above me. He kept one hand on my hair to hold my head in place and then guided his meat so that he could push down vertically into my mouth.

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