The Dream Job

"What do you do," he asked as I closed the door?

"Whatever you want," I smiled at him," But I should warn you, I'm trans. I hope that's not a problem."

"Not at all, in fact I prefer it that way, fewer unplanned issues down the road, if you know what I mean," he unzipped his pants and moved closer to me. I dropped to my knees, reaching out and pulling his cock from his pants," that will be perfect for starters, maybe later we can explore more," he smiled at me as I took him in my mouth. I had planned on taking my time, letting him relish the experience, but soon realized all he wanted was to get off and get back to the game. I changed my tactics and it was only a few more minutes before he filled my mouth with his juice, I squeezed the last few drops from his cock and licked them of with my tongue, being sure to let him see me swallow. He went back to the game while I refreshed my lipstick, there was a thousand-dollar chip on the table by the door.

By Saturday night, when the game was finally over, I had spent as much time in the small room as I had the poker room, every man there had cum in my mouth at least once, if not two or three times, several had fucked me, a few had sucked my cock and one had asked me to fuck him, When I cashed in the chips they had paid me, including the very generous tip from the man who won, Meagan handed me just over twenty thousand dollars, after keeping ten percent for herself, I wasn't about to complain. The men in the game had each paid one hundred and fifty thousand dollars to buy in for the game, several buying in multiple times, the chips they used to tip me was money they had already spent, it didn't even exist as far as they were concerned. The winner left with over two million dollars.

I had paid meticulous attention to the conversations at the table, noting a handful of companies I needed to check out. Several of the men had asked for my contact information and I had agreed to let Meagan give it out. She invited me back for upcoming games, the second weekend of every month, in the same place. There would be a group of regulars, all of whom had liked me very much, and a rotating group of fillers that she assured me would be just as generous. I agreed to give her the same ten percent of any outside earnings that came through contacts I made at her game, it was all highly illegal and was going to be very profitable.

Going forward, I would 'officially' be Meagan's financial advisor and any payments she made to me would be considered payments for consulting services. I would need to open a few bank accounts and stagger my deposits, above all I wanted to appear legitimate to the IRS. With the information I gathered, my investment portfolio should do very well and that would make the payments seem legitimate, too.

The cab was still three blocks from my apartment when my phone buzzed, the number was on the list Megan had given me,"2 pm, tomorrow..." there was the name of a marina and a slip number," dress casual, I have a suit for you to wear?"

"Yes," I smiled at myself as I typed the reply and hit send.

It was the man that had sucked my cock, his yacht was huge, over 200 feet long. One of his servants directed me to a cabin where I found a selection on bikinis laid out on the bed. I chose one that didn't require my forms and showed a bit too much of my ass and went to join my host.

We spent the afternoon lounging on the deck of the yacht, he rubbed lotion all over me for the pleasure and to make sure I didn't burn, and I did the same for him. He had what you might call a 'dad body,' not fat but not too fit either, probably twice my age, the hair on his chest reminded me of Sean Connery, with just a smattering of grey. I decided I liked him.

Before dinner, we showered together to get the lotion and sweat off our bodies, washing each other I ran my hands through the hair on his chest," May, I kiss you, Elaine," he actually asked me?

"I think I'd like that," he pulled me close and kissed me sweetly, sliding his hands down my soapy body and fondling my erection, as our lips parted, he turned me around and moved his hands to my hips, I knew what he wanted and bent over, spreading my legs just enough to allow him entrance. Dennis reached around me and started to fondle me once again as he began to thrust inside me, I remembered his gentleness from the poker game, he matched the pace of his hand with his cock, timing it so we came together, my knees got week as my orgasm ripped through my body, I could feel him shudder deep inside me, pulsing as he filled me with his seed.

After dinner, Dennis and I just talked, sitting on the top deck of his yacht, sipping wine, he told me about his late wife, how she had been the one that had introduced him to sex with men and how she had died from cancer just a year ago. I told him how I had started doing what I was doing, readily admitting that it had been very recent and that I was enjoying it far more than I thought I would. When we started to run out of words, he took me to bed and made love to me, his hands played my body like a Stradivarius, gentle touches and caresses, I felt like his universe revolved around me and did my best to make him feel the same way, we kissed and fondled each other, taking turns sucking each other but neither letting the other finish, finally Dennis rolled me on my back and lubed my ass, using his fingers to prepare me for his cock. I moaned softly as the orgasm I knew was finally coming started to build deep inside me. Dennis slid into me and took his time working all the way inside me, rubbing my chest with his hands, and pinching my nipples as he kissed my neck.

"God, just fuck me, please," I finally begged him.

"That's my girl," he let out a chuckle as he began to pound me as hard as he could. It ripped through me like a hurricane, an orgasm like I had never felt, spasms shook my entire body, my legs and arms cramped and my toes curled as my body shook and Dennis exploded inside me, "FUUUUUCK!"

Dennis just laughed, lying beside me, dipping his fingers into the gooey mess on my stomach and feeding me the salty residue, I sucked eagerly at his fingers until there was nothing left. He kissed me sweetly, like you would a small child. I fell asleep in his arms, awakening to the smell of the sea, his hand on my cock and his hardness against my back.

We made love again, and again until I finally begged him to stop, I could barely move. We showered together taking our time making sure nothing was missed. Dennis was hard again so I dropped to my knees and took him in my mouth, twirling my tongue around the head of his cock and slowly sliding him deep into my throat before I pulled him out, licking my way down his shaft, I took one and then the other of his balls into my mouth, and then both, sucking gently until he started to moan. Working my way back up his shaft to find a gift of hie precum, I eagerly dove onto his cock, taking him as deep as he could go. His balls against my chin, I held him there, slid my fingers up the crack of his ass and slipped a finger inside. When I found his prostate, he erupted down my throat. I pulled him free and kissed the tip of his cock, rocking back on my heels as he smiled down at me.

We dried each other off and I chose a different bikini as my uniform for the day. His butler had lunch ready for us on the rear deck, we sat and ate in silence, taking furtive glances at each other and grinning broadly at what had transpired.

"You make a very beautiful woman," he finally broke the silence.

"Thank you, I enjoy being Elaine, and she makes better money than Evan," I laughed.

" If this is what you really want to do, have you considered more permanent changes?"

"I'm not sure what you mean."

"Hormones, to start with," he was serious," Of course, we would want to keep that gorgeous cock of yours, wouldn't we?"

I blushed and he laughed, "and when the hormones begin to do their job, we can talk about some minor reconstructive surgery on your face and perhaps enhancing your breasts if you are not happy with them. I can help you with the surgery; it is what I do after all, perhaps in exchange for more of your time," he put his hand on mine.

The speed at which things were moving bothered me but it had all felt so right? A week ago, I was a promising young broker with a prestigious Wall Street investment firm who hadn't even thought about dressing in almost five years, now I was talking about female hormones and surgery with a man paying me for sex.

"You seem to have thought about this a bit. What did you have in mind?"

"I manage your hormones and do your surgery and while you recover, you come with me, on my boat, to Jamaica, we cruise the Caribbean for a while and then back, we would, of course, enjoy each other on the way."

"Hormones, and surgery too? I don't know, this is all happening so fast," Dennis pulled a photo album from somewhere and showed me pictures of his work with transgender women, it was impressive; all of the women were attractive, most were stunning. We spent the afternoon, sitting in the sun, talking about what he was suggesting, and I tried to wrap my mind around the whirlwind I had stepped into when I had accepted Ted's offer to go back to his room. I knew I liked the sex. I finally admitted to myself that what Dennis was suggesting is what I had wanted since I was probably seven. When I left, Dennis had given me prescriptions for hormones and I scheduled my surgery for two weeks from Monday, we would leave for Jamaica, two days later.

Dennis' investment in my fund was significant and I saw two more clients before my date with Ted. It was the same as before, Ted came in my mouth, made me drink his urine, and then tied me down while he and a few of his friends used me, there had been four of them this time not counting Ted and the stack of hundreds had increased in size accordingly. I talked to Ted about my proposed agreement and he was on board, we made a standing date for every other Thursday until he told me otherwise, except for when I would be on the cruise with Dennis. The number of friends he invited would vary but would never be more than the four I had entertained tonight, he also asked about referrals, it was an emphatic yes, especially since the one he had already made was working out so well.

The work on my face turned out to be minimal, tracheal shave, lightening my brow a bit, altering my hairline, and a little touchup on my nose, I pretty much looked like I had lost a fight with Mike Tyson. We deferred our departure for a week so I could get my sutures out and there would be no blowjobs from me until I was completely healed. Dennis understood because they were his orders, the trip was wonderful anyway, he treated me like a princess, making love to me every night, each time like it was the first, making it feel new and fresh and exciting as he explored my body finding new and more intense ways to bring me pleasure. He spoiled me with shopping and gifts once we got to Jamaica. The other islands and the return trip were much the same. We ended up spending a full month on his boat. I used the lessons in tenderness and compassion Dennis taught me to make my time with my other customers even more special for them which in turn increased their investments in my fund.

The next few months proved that Dennis had been correct, all my clients appreciated his work and what he had taught me during our cruise. Only Ted and his friends didn't find value in what I learned from Dennis, but their need had never been connection or compassion, to feel wanted, or needed, or appreciated, it was primal, power and dominance, they only wanted sexual gratification and the opportunity to humiliate someone they perceived as weaker than themselves. In response, I started dressing less provocatively letting their fantasy evolve to one where I was less and less a willing participant in the game and more their prey, struggling as they tied me down and begging for them to stop and even forcing myself to cry as they used me over and over. It worked, their investments in my fund grew each time as the level of violence I allowed intensified, the information they shared with each other about their business dealings was even more valuable. The hard rule was no visible marks, they would only cross the line once and the man that had given me the black eye was never asked back. Dennis had checked to make sure no real damage was done and Ted compensated me for the inconvenience.

With the information I was picking up, my fund was exploding in value, my stock in Ted's business alone had gone up four hundred percent when the deal had been officially finalized and had been climbing ever since. There were others that had done even better, in less than six months, I had accumulated close to two million dollars in the fund, and it wasn't showing any signs of slowing down. My breasts had started to grow and what little fat I did have was starting to redistribute to my hips, I had finished electrolysis and was completely free of hair from my nose to my toes, except for a small tuft I kept above my cock.

With two or three clients a week, every other Thursday with Ted and once a month at Meagan's game, I was pulling in over fifty thousand dollars a month, life was good.

"12:30 this afternoon," with the name of a restaurant, was all the text said. I didn't recognize the number, but Dennis had taken me on another trip and my calendar was empty for the next few days, so I accepted with a simple, "Yes."

I got there early, taking a seat on the sidewalk patio, and ordering a cup of tea, watching the crowd, and trying to guess who was going to join me. 12:30 came and went and I was just about to leave when a voice behind me said, "Elaine?"

I turned and smiled, he was handsome, wearing a mid-range blue suit, not expensive but not cheap, definitely not one someone that could afford my time would be wearing," Yes, I'm Elaine, you're late, now how can I help you?"

He pulled his ID out as he sat down, sliding it across the table," an acquaintance of mine said you might know a Meagan Cross."

"Shit," I almost said it out loud, opting to take a sip of my tea instead; someone had given my personal business number to the fucking FBI, and I had thought Jenkins and Jacoby had been in deep shit. I did my best to keep my composure.

"I know Meagan, she is a client of mine. I'm not really at liberty to discuss my dealings with my clients, the SEC gets picky about that," I studied his face, trying to get a feel for what he was after.

"So, you're a securities broker? That's not what I expected, how did you meet Ms. Cross?"

I picked up his badge," More of a consultant, I research investment opportunities for a very exclusive group of clients and I am currently doing quite well, Just tell me what you want Agent Simmons, and as I said, I am not at liberty to discuss my dealings or my relationships with my clients. If you are interested in investing advice, there is a very extensive vetting process. As for how I know Ms. Cross, a mutual acquaintance introduced us, she pays me fairly well to serve drinks and flirt with men who have more money than sense."

"So, you have you been to Ms. Cross' poker game?"

"On several occasions, as I said, I help out by acting as a hostess, I find it a fascinating dynamic and I like Meagan, what's your point, Agent Simmons?"

"Have you ever seen or experienced anything inappropriate, or illegal?"

"I know the laws around securities, not poker games so illegal is out of my purview, as for inappropriate, unless you consider me letting one of the regulars hug me and grab my butt at the end of the night, while he slips a thousand dollar chip into my bra because he thinks I brought him good luck to be inappropriate instead of good marketing, I think you're wasting your time."

"What can you tell me about the men who frequent the game?"

"Not much really, a few are also clients of mine, most I only know from the game and it's not really my place to talk about Megan's business. If you'd like more information on her business, I suggest you ask her, and if you'll excuse me, Agent Simmons, I have things I need to be doing this afternoon."

I left him sitting there and did my best not to run to my car. My first step was calling Meagan filling her in on the entire conversation as I drove to the marina to see if Dennis could help me figure out what the hell to do.

Dennis offered to make some calls to people he knew and suggested I lay low for a while. I took his advice and spent the next week going through my notes from my clients looking for opportunities I hadn't acted on, I found a few small opportunities and shifted some money around, took a drive upstate, found a great antique fair and bought a wonderful armoire for my guest room.

Thursday was Ted and I was really looking forward to the distraction, it had been over a week since Agent Simmons had called and hearing nothing was far worse than finding him on my doorstep every day. Dennis had called to check in on me but hadn't heard anything from his contacts.

I knocked on the door and Ted opened it, letting me inside, once I was past him, he shoved me onto the bed and his friends grabbed me, holding me down. I did my best to fight them off, or pretend to, but they were too strong. One of the pulled out a knife and started cutting my clothes off and I started crying. There was no harness this time as they took turns holding me down and using me. They were a lot rougher than usual and I began to worry that things were going sideways until one of them raised his hand to hit me and Ted grabbed his wrist. The roleplay continued until they were all completely spent.

The next morning, I found a change of underwear and a nice simple dress on the dresser. There was a flash drive in the envelope with my money, in addition to a nice bonus, Ted had videoed the entire thing, I had to admit it was fucking hot. I wasn't too worried about him spreading it around because out of context, it looked like he and his buddies forcibly raped some poor college girl.

"Thanks for the surprise, and for stepping in," I texted him.

"You're welcome. Thought you'd like that, and nobody ever hits you again, got it?"

I was just finishing my makeup to head to Meagan's game when my phone buzzed," Just cooperate, it will be alright," it was from Dennis. Before I could hit dial, there was a knock on my door, I dropped my lipstick in my purse, grabbed my jacket and went to find out what was going on.

"I thought you might like a ride to work this evening," It was Agent Simmons, "we can talk on the way."

I locked my door and followed him to the elevator. When the door closed, he handed me a folder, I opened it and started looking through the papers; names, dates, financial transactions, they had everything, this was a detailed analysis of my life for the past nine months. He held the door to his car, and I got in, completely numb.

I closed the folder and handed It back to him," what do you want me to do," I could feel the color drain from my face?

The driver pulled away from the curb and Simmons handed me a second folder full of pictures, it was a man I had never seen before, someone named Victor with a last name I couldn't pronounce. Behind the pictures of him were more, gruesome and grotesque, young girls, some looked like they weren't even teen aged, most had been beaten or brutalized in some form or fashion, almost all had track marks up and down their arms.

"He will be at the game tonight. All I need you to do, is do what you do, flirt with him, get him to call you and make an appointment, get him to invest in your fund," the sarcasm in his voice was palpable," he handed me a lipstick, when you get him alone, get him to talk to you like Ted and his friends do. I'll be recording everything. You help me with this folder," he held up Victor's," and this folder goes away," he raised mine," forever. Elaine, this guy is as bad as it gets, child trafficking, drugs, weapons, you name it he's involved. I won't lie to you, there is risk, but It's my job to make sure you're safe, just like Ted did."