The Dream Job

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"You know Ted?"

"I do. The movie he made was for me, to prove you could handle Victor, and don't be too hard on him, he really cares for you and I gave him about the same choice I'm giving you."

"But Victor likes young girls, he's not going to want me."

"No, Elaine, he sells little girls, you are exactly what he likes."

"Shit, can you ask the driver to pull over, I think I need to throw up?"

I got back in the car and Simons handed me a wet wipe and a bottle of water," What about Meagan," I asked?

"We have been watching her game for a long time, except for your involvement, it is perfectly legal, so if we ignore what you are doing, she will be fine, if not, well," he didn't have to finish the thought.

To say Meagan was surprised to see was a bit of an understatement, got a huge hug and spent ten minutes reassuring her that everything was going to be alright, I changed into my uniform just as our guests started to arrive. Meagan explained to them that the small room was off limits due to someone at the game talking too much to the wrong people, angry eyes darted around the room but everything was soon as close to normal as it could be once the first cards were dealt. Victor was impressive, a little over six feet tall, his aura dominated the room, definitely not someone to mess with. His skills at the table were equally impressive, he played the game like he was playing chess, I paid close attention, making sure I was always somewhere nearby when he stayed past the flop, trying to let him know I found his prowess very attractive. When he went all with three other players, I picked up one of his chips, kissed it and put it back on the table with the rest," for good luck," I smiled.

He stood behind his chair with his arm around my waist and watched as the dealer flipped the cards, the turn gave another player a flush, beating Victor's two pair. I put my hands on his face and kissed him, the river was the third ace, giving Victor a full house, aces over jacks.

He handed me ten thousand dollars in chips," you stay here with me now," he smiled. For the rest of the game, I only left his side to get him another vodka. When he took a break, I went with him, when he ate breakfast, I made his plate and served him. In these little capsules of time, he told me his life story, where he grew up, all about his abusive father and drunken mother, how he learned to be a hard man with little mercy, how he did what was necessary to survive; that I understood. Mostly I just watched as he eliminated player after player until there as just one. A failed bluff left the poor guy with next to nothing, his only option was to go all in; the cards weren't there.

I wrapped my arms around Victor's neck and kissed him as hard as I could, he picked me up and slid his hand under my dress, stopping and almost dropping me," you are," the look in his eyes confused me, "not what you appear to be," he set me down.

"I'm sorry, I thought you knew, everybody knows," I looked around the room forcing tears to my eyes.

"No, you misunderstand, it is not a bad surprise, just a surprise," he pulled me close and kissed me again.

"Meagan," Victor turned to her," this has been great fun. You have a wonderful game here and I would very much like to return. Please keep twenty percent for yourself,' he paused and looked at me," and give the same to my delightful good luck charm."

"Victor, no, that's too much," he cut me off.

"Trust me my dear, you will earn it tonight," I blushed, Victor's driver took the case with his winnings and Meagan offered to hold my tip for me until I could come pick it up. I grabbed my purse and went to change before following Victor out of the room to the elevator.

His penthouse was an exercise in excess, huge with a commanding view of the New York skyline, it had a full bar with only the most expensive liquors, the walls covered in art I'm sure was all original; I recognized a few Monet's and a Van Gogh I had only seen in magazines. Exotic animal skins covered the floors and amazing sculptures filled the corners and nooks and crannies; it was part museum and part hunting lodge, but it all seemed to fit Victor, he set the suitcase by the bar and poured himself a drink, taking my hand, he lead me to his bedroom. The bed was massive, four thick wooden posts rose from the corners, each with metal rings and ropes attached, he opened a cabinet in the wall, it was full of things I had only seen in porno movies, handcuffs and whips, chains and leather straps, he turned toward me and glared," do you begin to understand how you will earn your money?"

I just nodded.

"Good, now go clean yourself," he pointed to a door across the room. I took a quick shower, getting the smells of the game off my body and using the hot water bottle, made sure I was clean inside as well. When I came out of the bathroom, Victor smiled admiring my naked body," the contrast is intoxicating, your beautiful body, breasts so pert and firm, your hips so round and full, and in the middle of it all, a cock; se very feminine, yet not, don't you agree?"

"Yes," it was barely a whisper. I walked across the room on the balls of my feet, trying to be as sensuous as possible, running my hands up his chest, I started to unbutton his shirt exposing the muscular underneath. I ran my fingers through the hair, finding his nipples and playing with them, pinching them between my fingers.

I pushed his shirt off his shoulders and kissed him between his breasts, drawing circles with my tongue until I found one of his nipples, I sucked lightly as my hands made their way to his belt, slowly unfastening it, pausing to run my hand down to his crotch and rub his growing erection, Victor moaned; then the button and the zipper, then both hands to his crotch to free his beast from its prison, my gawd he felt good in my hands. Leaving a line of soft kisses down his stomach, I slowly moved to my knees until I was eye level with his cock. I flicked it with my tongue, realizing at the same time, I had left my purse, and Simmons recording device in the other room, I gave his balls a quick kiss, got up and ran to the bar, giggling like a school girl.

Victor looked a little dismayed, he obviously was not used to being kept waiting and his erection told me the need was eminent, I made an elaborate show of slathering my lips with the bright red lipstick before I got on my knees and crawled across the floor to him, making sure to leave the lipstick on the table next to his bed. Bright red lip prints soon decorated his manhood," you're going to have to clean that off, he smiled at me."

"My pleasure," I winked as I licked him from his balls to the tip of his cock, catching the first of his precum as it leaked onto my tongue. Taking my time as I worshiped his shaft, I alternated between licking and caressing his balls to taking him as deep in my throat as I could, the thickness of his cock, made it problematic but I let him know it was not for lack of trying. Victors moans grew louder and louder as I kept his orgasm at bay; I knew what I wanted, I just needed him to get there. Finally, he grabbed my head and shoved his raging hardon all the way down my throat, my body shuddered with pleasure and I spewed hot juice on the floor as he filled my throat with his seed.

"So, you like it a little rough, do you," he laughed as he softened in my mouth?

I just rocked back on my heels and smile up at him.

He cupped my face in his hand turning it one way then the other, "such a pretty little thing you are, it would be a shame to damage such a lovely face," he walked to the wall beside his bed and opened a hidden closet," let me see what other pleasures we can share tonight."

I just sat where I was as he chose the implements of his desire; handcuffs, nipple clamps, blindfold, and a flail; I was going to earn my tip and my freedom, but it was not going to be cheap. I offered Victor my wrists, he cuffed me and led me to the corner of the bed, attaching the cuffs to a rope, placing the blindfold over my eyes, and then the nipple clamps, shit they hurt. The rope pulled my arms over my head until I was standing on the balls of my feel, I cold feel the ache in my shoulders, when the flail stung my ass, I screamed.

"Now, now, my little one," Victor kissed me," If you make too much noise, I will have to punish you, just relax and enjoy."

"Punish me, what the fuck do you think you're doing now," the thought raced through my mind?

The flail bit me again and I muffled the scream, with the ache in my shoulders and the pain in my chest, I tried to keep my head clear, a third time, again I muffled my scream.

"Good," Victor kissed me again, "much better, just relax and you will learn."

My fucking cock started to get hard.

It went like this for what seemed like forever, Victor whipping me and then consoling me with a kiss, telling me what a good girl I was, I could feel the whelps rising on my butt and precum dripping from my cock. The flail hit me again and my mind started to get confused, was it pain or pleasure I was feeling? The line blurred and he continued. When he stopped, I was shuddering, his hands found my body spreading a cool soothing lotion over my aching ass, his hands were soft and gentle, I was so confused, it hurt but felt so good at the same time. His hand slid up the crack of my ass and his fingers inside me, I no longer cared what he had done, I just wanted him inside me; he obliged, shoving his cock into my aching ass fucking me hard. When he reached around me and removed the nipple clamps, I exploded. The pain, the pleasure, they were one and the the same; the intensity of the orgasm, my entire body shook with the overload of sensation, "Holy FUUUUCK," I cried as the aftershocks ripped through me.

Victor left me hanging there, his cum dripping from my ass, he hummed to himself as he moved around the room. I heard water running. He removed the blindfold, kissing me again, "you did well little one," he smiled, slowly lowering me into a puddle of mush at the foot of his bed, I couldn't move, everything in my body ached. Victor removed the cuffs from my wrists, picked me up and carried me to the bathroom, gently lowering me into a tub of heavily scented hot water, I recognized the subtle hint of lavender.

The feeling slowly returned to my arm and legs, I could hear Victors muffled voice in the bedroom, he seemed to be agitated about something. Climbing out of the tub, I found a big fluffy towel and patted myself dry. My nipples were still tender, and my ass was bright red, crimson lines crisscrossed my butt cheeks. It was going to be interesting sitting for a few days, I could tell.

Victor was standing by his desk looking out the window," Get down there and make sure everything is as it should be. Pier seven, Eastern Star out of Malaysia. If anything is damaged, you have my permission to cut off the captain's dick and feed it to him. I will meet you there."

I slipped my arms around his chest from behind as he hung up, kissing him between the shoulder blades, "you sound stressed Victor, maybe I can help you relax," he turned in my arms and brought his lips to mine.

Picking me up, he carried me to the bed, "you are good for me little one, I think I will keep you," his voice softened as he threw me on the bed, flipping me on my back and pushing my legs up to my shoulders, he fucked me long and hard, taking his anger with whomever had been on the other end of the phone out on my aching hole, we exploded together, his hot juices filling my ass as mine covered my stomach and breasts.

"Now rest, I will want you again when I return," he kissed me, got dressed and left. I took a quick shower, crawled into his huge bed, and fell asleep.

"Elaine, Elaine," a vaguely familiar voice was calling my name. I rolled over and opened my eyes, Agent Simmons was sitting beside me on the bed," you did good," he smiled at me. "We got him red handed. Because of you a dozen girls are safe. Now get up and get dressed and I'll buy you lunch."

I climbed out of bed and headed for the bathroom, picking up my clothes along the way, noticing the impact seeing me naked was having on Simmons, and smiling to myself. Simmons was admiring one of the Monet's when I found him, he smiled at me and headed for the door, I stopped and picked up the briefcase by the bar and followed him, he didn't say a word. It was a bit mercenary, but I figured it would make sitting down a little easier for the next week or so, and Victor wasn't going to be needing it where he was going.

Victor was convicted on a couple dozen counts of all kinds of stuff, he would probably die in prison; considering what he had been doing to those young girls, it wouldn't be from old age. The situation between me and Ted was strained to say the least, I met with him and his friends one more time and we all agreed it was time to move on. With the pass from the FBI, the game went on, and I continued to see three or four clients every week. My investment portfolio was growing as much from the bits and pieces of information dropped at the game as it was from my own research and intuition.

Dennis slipped his arms around my waist as I stood at the railing of his yacht, we were moored off the coast of Peru, the launch was almost ready to take us in to shore where the helicopter would take us to a place called Cusco, from there it was a very scenic train ride to Machu Pichu. Dennis kissed my neck and I laughed out loud.

"And what is so funny about that," he started to tickle me?

"It just hit me," I said, leaning back into his arms, as much to get him to stop tickling me as for the feeling of security it gave me," It has been almost three years since I moved to New York with a degree in finance and an MBA for my dream job, ready to conquer the world. Then my job collapsed and my entre word imploded; now here I am, a high dollar transgender prostitute with more money in the bank than I can count, I'm on the back of a multimillion dollar yacht with my billionaire boyfriend, being spoiled rotten, looking up at the most impressive mountains anyone has ever seen, as dream jobs go, this one is not too bad," I turned in his arms and buried myself in his kiss.

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11 Comments
Freebird6996Freebird6996over 1 year ago

Different, but still intoxicating...

FranziskaSissyFranziskaSissyover 1 year ago

Elaine has been through some hard times painful moments to become a pain loving whore ...... It's sounds like a normal work path for a whore ..... Interesting story, but im sure I don't wanna ever have an FBI Agent sitting at a dinner table close to me showing his badge talking business

AnonymousAnonymousover 1 year ago

You are an incredible writer, Thank you for sharing

AnonymousAnonymousover 1 year ago

Absolutely loved the story, as with all your stories . Can’t wait for the next one.

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