Whatever It Takes Pt. 04

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Elaine has to pay in services to settle the debt.
18.8k words
4.31
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7

Part 4 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 will soon learn 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.

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);

  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; and

  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.

WHATEVER IT TAKES:

WORKING OUT A DEBT IN JAMAICA

TUESDAY

The Show Must Go On

Empty Spaces.

What are we living for?

Abandoned places.

I guess I know the score.

On and on.

Does anybody know what I should be looking for?...

Show must go on.

Show must go on.

Inside my heart is breaking.

My make-up may be flaking.

But my smile still stays on...

On and on.

Does anybody know what I should be looking for?

I guess I'm learning.

I must be warmer now/

I'll soon be turning

'Round the corner now.

Outside the dawn is breaking,

But inside in the dark I'm aching to be free.

Show must go on.

Show must go on.

Inside my heart is breaking.

My make-up may be flaking,

But my smile still stays on...

Show must go on.

Show must go on.

I'll face it with a grin.

I'm never giving in -

On with the show.

I'll top the bill,

I'll overkill.

I have to find the will to carry on with the show.

On with the show.

Show must go on.

Written by John Richard Deacon and Brian Harold May; recorded and popularized by the rock group Queen

MONDAY NIGHT'S DREAM

Knowing that I had been raped and humiliated and put my whole life at risk, I fell into an uneasy and shallow sleep. The nightmare began in the darkest part of the night. I was naked standing beside the bed in our home in New York. All the lights were on, and it was very dark outside. Michael, was on his back on our bed, also naked. His penis was erect and pointing to the ceiling. He motioned to me to climb on top of him. As if I had no will of my own, I crawled over the bed and straddled him. I felt him raise up as I slid down. He slipped into me like a finger in a silk-lined glove. We began to move together slowly. He looked up at me, wide-eyed, then put his hands gently on my languidly-moving breasts. "Elaine, you are a whore," he said, as if only to explain the obvious. We moved more rapidly now, slipping and sliding as I bent forward to rub my breasts on his chest.

He pulled my head forward toward his. His tongue slipped into my mouth and began to search for mine. I felt sexual electricity flowing up his rigid flesh and into my body. My mind was disengaged as I ground my pelvis down on him. We began to move in unison as he sucked on my tongue. I heard myself wailing. My whole womb was on fire! I thought I had been split wide open. His fingers dug mercilessly at my ass-cheeks, and he bit down and made me wince with pain, proud of his total mastery over my mind and body. He freed my tongue and lifted his head to watch his hardness as it fucked in and out of my body.

I concentrated on the erupting passion that coursed through my body. I forgot everything - who I was, my husband, my baby, my life. All that counted was my own wild desire and the pulsating shaft that would soon bring me relief. I was no longer in control. I was a frantic sex machine riding a magnificent penis. I craved the pleasure, the lust that incited me was the only thing about which I cared.

"Fuck me, you bastard, fuck me!" was the message I screamed out to Michael.

Then I became aware that we were not to be alone. The door to the room had opened. My husband Paul now entered. He was naked too and came toward us on the bed. I tried to rise but could not make myself move. Then Michael reached up and pulled me flat against his chest. My buttocks waved in the air. My body was slick with sweat, and I still wanted Michael to finish what he had started.

Paul then joined us on the bed. I heard him say, "Elaine, you are a whore. You deserve to be treated as one."

Then he was behind me, poking between my buttocks with his engorged penis. I knew what he wanted - what I had not let him have on the beach. I felt Paul press his cock against my anal ring. I opened my mouth to protest, but Michael gripped the back of my head and pulled my face to his. His tongue was forced into my mouth while my husband kept probing at my rear channel.

In my mind I said to Paul, "I am so, so sorry." The words were framed in my mind but never spoken as Michael's tongue in my throat suppressed all coherent speech. I felt Paul move forward, and the head of his cock began to bore into me. Then I felt him break through and enter me anally. It was painful. My own husband was sodomizing me - he kept pushing forward, going a little deeper each time. It went on and on - deeper and deeper. With declining strength, I fought to keep him out, but he sank further into me. As I clenched my muscles to repel him, I knew that by squeezing his cock I gave him pleasure and only encouraged him. It was deeply humiliating, but I deserved the pain and the humiliation. I betrayed Paul and put the lives we had jointly built at risk. Finally, I felt his public hair on my buttocks; he was in as far as he could go. It felt as if he might split me in two, as if he had shoved his arm not his cock up my ass. Unlike the other night at the beach, in this dream I did not resist him. For some reason, I accepted the dominance of these two men over me.

Michael and Paul began to move together. I was caught in between and had no control over when or what was done. Paul went very deep; I felt his thighs press against my buttocks. I wanted to protest, but the pain and shock of being raped anally by my own husband left me unable to speak. He drove at me harder. The pressure in my butt grew as the piston of his prick increasingly drove as deep as it could. All the time my hips were making little movements, enjoying Michael who remained deep in me.

"Christ, she is tight," my husband said to Michael as if I was not there or could not hear. Paul withdrew his dick slowly, until just the head remained in my rectum. The he drove back into me, and my ass hole screamed from the searing fiction. His balls slapped my buttocks on the inbound stroke.

He pounded deep into my rectum, stretching me to the maximum. He was humiliating me in front of Michael, the two them in some kind of macho boy-thing about who could do it deeper and harder. I tried to relax my muscles, but it did not help; the pain did not diminish. I could feel the two pricks inside me, sliding against each other. Paul and Michael started to pull back in unison, until they were both barely inside me. Then they would shove all the way back in until they almost met somewhere deep inside me.

I was stunned at the feeling that they began to stir up. I began to be aroused, so incredibly sexy. Everything in this dream began to spin around. I felt pleasure, like I was an animal that was in heat. I was building to a climax like none I had ever had before.

Then in unison, they began to chant:

"One, two, three, four,

Let's fuck the dirty whore.

Five, six, seven, eight,

What a slutty date.

One, two, three, four,

Fuck her front and rear doors.

Five, six, seven, eight,

She deserves her filthy fate."

The dream seemed so real that I could feel their organs penetrating me. I could feel every blood-swollen ridge line as they sawed in and out of me in unison, keeping up the stroke to that god-awful chant..."whore...slutty...filthy"...went through my mind over and over and over again until I began to believe it.

I could feel my body begin to betray me. I was on fire. I tried to suppress a moan. I was trying to hold back, but I had lost control. I allowed a prolonged moan to escape me. I arched my back to allow Paul to go deeper in my bowels. My toes curled, and I wrapped my fists in the sheets. I began to move with them faster..."one, two, three, four...fuck her front and rear doors." Then the whole world exploded in an orgasm so deep and strong that I thought it would simply tear me apart. My snapped my head up like a man being hung, and I screamed a long throaty cry. The two of them also shouted and climaxed inside me. I could feel their cum spurting into me while I twisted and moaned between them. I felt their fluids mixed with mine running out of me onto the sheets. My face was beaded with sweat, my body as wet as if I had stepped from a shower.

When I came down from the orgasm, it was still a dream. But now I was in a different bed. The bed was warm from being used, and the musky smell of sex emanated from the sheets. I was still naked. Every muscle in my body was aching. All I wanted to do was wash and wash and then wash again. But I could not move off of the bed.

I looked around the room and recognized it. I was in the bedroom of the house where Michael took me I was on the bed where we had sex. Then the door opened and three naked men entered the room, all in a state of erection. One was black, the other two white. One of the white men was Mack, the bartender from the hotel.

Then began a kaleidoscope of sex acts. It was like a video tape on warp drive. I saw and felt myself penetrated every which way. I was pushed and pulled into positions I had never even conceived of as they slipped in and out of me, always leaving copious amounts of cum in me and on me. Eventually, I was a willing and learning participant. By the end, I was like a tame wife gone mad - oral, anal, scratching, cursing, legs around backs and shoulders, the whole whorehouse works. At one point I thought how little I had previously known about certain kinds of sexual performance. How much quick pleasure they brought, but then how few of them were ultimately worth knowing.

The last sequence in the dream had Mack on my chest, his buttocks resting on my breasts. His penis was in my mouth. I was performing fellatio. I must have been doing well because Mack was smiling. "Suck it, little Miss Rich Bitch, suck it." And I sucked and sucked, finally he came. Some went down my throat, but a lot leaked out of my mouth and down my chin. He withdrew and rested his soft organ on my face. I could smell the pungent odor of both him and me on his organ. "Nice job, Rich Bitch, nice job! You are a good cock sucker." He smiled, and I smiled back.

Then the scene faded to black.

TUESDAY MORNING'S REALITY

How long was it before I realized that I was no longer asleep? How long before I realized that I had fallen out of bed at some point and had crawled across the room in my sleep? I found myself on my hands and knees in a corner, butting my head against the place where the walls came together, doing it over and over again like a lunatic in an asylum.

I knew it was dawn because light had begun to filter into the room. I could not move out of the corner because it felt safer than the wider room would have done. For a long time the dream's force held me even after I knew that I was fully awake. I know that I was shivering all over and that I was cold even though the room was warm. I was wet from the waist down because my bladder had let go. I stayed there in the corner, gasping and wet, staring at nothing, just staring. I felt as if I had had a night of awesome sex. But I knew that was impossible. I wondered if you could have a nightmare powerful enough in its imagery to drive you insane. I thought then that I almost found out last night.

Finally, I was able to leave the corner. I crawled rather than walked, consistent with the dream everything below my waist hurt. At last I ran shoulder-first into the bed. I stood up, yanked the pillowcase off the extra pillow, and wiped my groin and upper legs with it. Then I crawled back into bed, pulled the blankets up, and lay there shivering on a hot day in the tropics. I listened to the resort start to come to life all around me. I stayed that way for hours - not sleeping, almost afraid to sleep, but not moving either. I kept trying to sort out what had happened to me. My head something awful, and I felt nauseous, as if I had overdosed on cocktail of drugs.

At some point (it turned out to be 10:00 am) I turned to the night stand to see what time it was, I saw was the two $100 bills that the son-of-a-bitch Michael had given me - two tangible reminders of how stupid I had been. I kept thinking that I could not have been so careless as to have gone to a "party" with some guy (a black guy, no less!) that I never met before, got drunk, did drugs, had sex with him, then let him continue to abuse and fuck/rape me in the limo ride home. I was educated and smart - too smart I always thought to let something like this happen. I was too depressed to move and lay staring at the ceiling with alternating waves of anger and depression cycling through my mind.

After about an hour of lying through fighting off tears and intense rage, trying to achieve enough mental stability to just get out of bed, I heard pounding on the hotel room door. It was a bellhop with a package that he said someone gave him in the lobby to bring immediately to my room. I was distracted and leapt out of bed thinking that Paul had returned. Why he would have knocked instead of using his key never crossed my mind. When I opened the door, the black bell hop's eyes nearly opened wide, and a big grin crossed his face. Instantly I remembered that I had worn Paul's pajama top to bed, and now I was standing nearly naked top-to-bottom in the door to my room. The pajama top gaped open exposing the areolas of my 36DD breasts as well as my blonde stubble public hair and naked shaved crotch showed. I grabbed an envelope from his hand and slammed the door in the guy's face. Drooling over my body was tip enough. I figured my office had sent something to me for my concurrence or insight. At least it would re-focus my mind off the events of Monday afternoon and evening. I could not have been more wrong.

The package contained an un-labeled USB drive and more than a 20 high resolution 8x12 color photographs. The photos were from various times during the prior day. My face was clear in every shot; anyone who know me would know it was me. The first showed me drinking in the bar with Michael, maybe taken by the bartender, Mack, when I was not looking, using high speed film so no distracting flash was required. Most were from the ride home. Two showed his dick in my mouth, my lips squeezing down on him and his dick wet from saliva and secretions. Another one contained the dildo shot, my self rape done for the camera. Other highlights included the spread cunt "backdoor" shot, the "show pink" to the camera shot, and a best and final one showed me pulling on the miniskirt with his cum dripping out my pussy and down my legs.

With trepidation I inserted the USB drive into my laptop. It contained rolling unedited footage of sex acts with men that I did not remember except from the dream that was not a dream but had actually happened. One was on what appeared to be the same bed on which Michael and I fucked. It showed a young black guy wearing nothing more than a ski mask, maybe 20 or 22, on the bed with me. Both of us were naked. I was on my right side while he had his left hand on my left knee, lifting my leg so that the camera could focus on his dick pounding into my cunt from the rear. I had no recollection of this happening. He had turned my face to the camera so that it was clear my eyes were open and a stupid, blissful grin was on my face.

It got worse. Now I was on my back, my head turned toward a white guy who had a couple inches of prick in my mouth while between my spread legs, a the same black man held my legs in the air by my ankles and fucked into my cunt. Then I realized that the man in my mouth was Mack, the bartender at the hotel. I felt sick and ashamed that I could be so stupid. There I was having sex with two guys at once. I remembered none of it. Maybe it was one of those digitally "enhanced" things, but somehow I doubted it. I knew it was me; last night's dream seemed real because it was real - just a replay of what had happened only hours before in the house where Michael took me. The next video shot showed a close up of a white dick (Mack's?) ejaculating onto my face and open mouth; the resolution was so good that the ripples in the cum in my mouth and on my chin were visible. The tape's audio was not the best, but it was clear that I made no protests and moaned and groaned as if I was enjoying my gang rape. The opioids they fed me turned me into participant rather than a victim and destroyed any hope of using the video to show the hell that they put me through.