The Dream Job

Another story of transition, this story is not as much of a love story as most of my others, it contains some graphic elements including a little bondage, so if that's not your thing, you will want to be aware. As always, please let me know what you think as your comments are my inspiration. Thanks

*****

It had been my dream job, an entry level broker with no clients of my own, yes, but at a prestigious Wall Street investment firm, Jenkins and Jacoby wasn't the largest by a long stretch, but it had a very impressive client list including high-ranking government types, business moguls and even some Hollywood names you would recognize. I had a degree in finance, my MBA, my securities licenses, excellent grades and had nailed the interviews with the recruiters, selling everything I didn't want to take to New York, I had moved halfway across the country for the opportunity. There had been a very nice signing bonus and It even came with a two-bedroom apartment in Brooklyn about two blocks from the subway in a building the company owned.

"Mr. Thomas, Evan Thomas, the FBI agent called my name, I hadn't been there two weeks when the raid had happened, there were charges of money laundering, embezzlement, and fraud, the owners of Jenkins and Jacoby had been stealing its clients blind for years and had taken to laundering money for a cartel to cover the losses, I had hired into a veritable shit show. After four hours of questioning, they had decided there was no way I could have known anything about what was going on, less than two weeks after landing in New York, I was jobless with my only reference all over the front page of every newspaper and on every news website in the country. The only good news was I got to keep my signing bonus, that combined with what savings I had would keep me afloat for a while, assuming I got to keep the apartment.

"Happy fucking Friday," I laughed because the only other choice was to cry as I got off the subway and made my way up to my apartment.

Elaine hadn't crossed my mind since I started grad school. Her name was written in big block letters on two of the boxes stacked against the living room wall of my apartment. She had always been there for me. Since before I was even in middle school and a friend had helped me discover her, Elaine had calmed the stresses of my life even softening the curves of my parent's divorce. She was the reason I had grown my hair out in the first place. My dad didn't know, my mom understood, helping fine tune a few details, and even took her shopping from time to time. I pulled the boxes from the pile and carried them into my bedroom. Familiar feelings and urges bubbled to the surface as I pulled the bright colorful fabrics from one box and the lacey lingerie from the other.

A long hot bath was in order, I poured a few capfuls of the scented oils from one of the boxes into the tub before I climbed in. I took my time relishing the feeling and reliving the memories as I shaved my arms, my legs, under my arms, and got rid of the small amount of hair I had on my chest as the soft scent of the lavender oil relaxed me even more. The routine came back to me, the garter belt was first, it always was, and then the stockings, I chose matching panties and bra, tucked my bits out of the way and slid my forms into my bra, the adhesive on the forms held them in place as I adjusted them.

My face was next, I shaved twice to get it as smooth as I could before I sat down to apply my makeup, focusing on the lessons my mom had taught me, Elaine slowly appeared before me in the mirror. I used my curling iron to give my hair some shape and slipped on a simple pink top with a floral skirt and stepped into a pair of black low heels. Moving my wallet and keys into my purse, I dropped my lipstick and compact into the bag, smiled at myself in the mirror and headed for the door. I had forgotten how wonderful this felt.

"Someplace nice, and quiet," was all I told my cab driver, he dropped me at a small Irish pub next to a hotel that belonged to a national chain servicing mostly business travelers, I ordered a pint of Smithwick's from the bartender and found a seat in the corner where I could watch the word go by and try to figure out what to do next.

I could tell by the way he scanned the room; he was looking for company and I did everything I could to not make eye contact. All I needed now was to have to fend off the intentions of some guy that, even if I were interested, would probably not be looking for what I had to offer. I smiled at the thought of what he would think when he found out, and that was my fatal mistake. "Hi, I'm Ted, can I join you?"

He had a nice face and an honest smile, so I said," Sure, have a seat, I'm Elaine."

"Look, I usually don't do this, it's just that I closed a huge deal today and I'm looking to celebrate, and I hate drinking alone. Is that OK?" I nodded and smiled, "so what brings you out, you here on business?"

"No, just looking for a quiet beer, so tell me about your deal, you sound excited."

Ted went on for hours, going into detail of the deal he had just closed. I understood a lot of what he talked about and could see the significance of what he had accomplished, it also occurred to me that his sharing his excitement was probably violating several facets of the non-disclosure clause of the deal he had just signed. I just smiled and listened, asking him to explain some of the more complex issues in language I could understand. He bought me dinner and the conversation turned to his life, he was divorced and didn't get to see his kids as often as he liked, so he was also lonely and admitted that celebrating his big deal wasn't the only reason he had sat down with me.

When he asked me to go back to his hotel with him, I put my hand on his arm," Ted, you're a really nice guy, but you should know," I paused, I had never opening outed myself before and I had no idea how it was going to go," I'm a guy, trans, a cross dresser, I don't think I'm what you're looking for."

"That doesn't have to be a problem," he blushed as he smiled at me," for what it's worth, you are stunning, I didn't even put it together until you told me and I go both ways, so," he left the question hanging of the thick air."

A million reasons why this was a bad, no, an absolutely horrible, idea raced through my mind. I had done it before, and it hadn't been a bad experience. It had been with a roommate in college, we had been out drinking and when we got back to the dorm, he had climbed in bed with me and started kissing me; I just went with it without thinking about it. He had sucked me and then I him, "That was kind of nice," I remembered thinking. Then he had turned me over, spreading lubricant over and in my ass, he entered me from behind, it hurt a little at first, by the time he pulsed inside me, I was enjoying that, too. The next day he had apologized profusely, I told him how much I enjoyed it and we became lovers. By the end of the semester, I knew more about how to please a man than I did a woman. It had never happened again. To say I hadn't thought about it several times since would be a lie.

I smiled at Ted as I picked up my purse and slid out of the booth," why not, the distraction might even help," I thought to myself as we walked out of the pub and across to Ted's hotel. Ted took his time seducing me, while I played them a bit, my nerves were very real and I let him feed off of them as he slowly undressed me, touching and caressing each new spot he uncovered, nibbling at my neck and kissing my collar bone as his hands slid down to my breasts, then to the hem of my blouse as he pulled it slowly up my body, exposing my trembling stomach, "You've done this before," he asked as I bit my lip and looked into his deep brown eyes.

"I have," I smiled, leaning forward and kissing him as he dropped my blouse and drew delicate lines down my arms with his fingers, sliding his hands around my waist and pulling me tight against his body. I could feel his erection between us as I pulled his shirt free from his pants, his hands found my hips and he smiled as I slowly unbuttoned the shirt, biting my lip again and drawing just the tip of my tongue across my upper lip as I slid it back off his shoulders and let it fall to the floor next to my blouse. My hands found his chest, Ted was very fit, his chest and abs tight with not too much muscle, not a body builder but he did something to stay in shape. I ran my thumbs across his nipples, kissing him again as my fingers traced the outline of his muscled stomach, making their way to his belt. When his pants fell, I slid my hands to his crotch, inside his boxers to his waiting manhood, grabbing the shaft gently with one hand as the other continued down, fondling his balls. He wasn't shaved but the hair was short and a contrast to his smooth chest, it felt soft against my hands. I slowly dropped to my knees, pulling him free and admiring the perfect symmetry of his member. Smiling up at him, I waited for his permission, he nodded and smiled and I drew a wet line from the base to the tip, eagerly accepting a small flow of precum as I closed my lips around the head of the warm gift in front of me. Tracing circles around the tip, I slowly drew him into my mouth, closing my eyes and imagining how it would feel if it were mine, I took him deeper and deeper until there was no more to take, he had slid completely down my throat, his scrotum nestled gently against my chin.

Ted took control, placing his hands on either side of my head, he began thrusting, at first his aggression bothered me but as he started to moan, I found it a little exciting and I focused my attention on fondling his balls and caressing his tight butt, sliding my hands up the small of his back and down again until he shoved himself as deep as he could go and exploded down my throat. He softened and I found I could fit him entirely in my mouth, enjoying the feeling for a minute before I tried to pull away," I have another gift for you," he help me tight against his pelvis and laughed softly as I felt the warm liquid course down my throat and into my stomach. When he was done, he pulled himself free. I looked up at him, a mixture of confusion and satisfaction on my face," that wasn't so bad now was it," he stepped out of his shoes and trousers," now get undressed," he said it almost matter-of-factly as he walked over to his suitcase.

Picking up all the clothes from the floor, I folded them neatly, placing my skirt and underwear with them on the small dresser across from the bed, Teds clothes in one neat pile and mine in another. I could have just as easily put my blouse back on and left, especially after he peed in my mouth, but I was entranced, I wanted him to treat me like this and I didn't know why. Ted was unfolding some sort of leather harness, laying it out on the bed, I walked up next to him and pout my arms around his chest, kissing him on the shoulder, "thank you," I whispered.

He helped me into the harness, laying me across the bed so my head hung down on one side and making my ass accessible from the other, he fastened straps to the base of the bed and I found I could not move. My hands were tight at my sides and my knees at my chest.

"Are you comfortable," Ted smiled as he admired his prize?

"Yes," my senses were on fire with a mix of fear and excitement. I was completely helpless. I could feel tears starting to well behind my eyes.

"Now, now, nothing to worry about, I'm just going to invite a few friends to come join us. That will be fun, don't you think?"

The tears were openly flowing now," what the fuck did I get myself into," I thought as he took out his phone and made a quick call.

He slid the blindfold in place and began applying lube to my hole, sliding one then two fingers inside me; I heard the door open and three voices entered the room. If I objected, he never heard or cared. The four men took turns using me, filling my throat and then my ass with their hot seed. I lost track of how many times someone came inside me. I was tired and sore and humiliated and ecstatic by the time they were done, my stomach covered in my own juice, I had experienced one orgasm after another as the men used me. Ted unfastened the harness and helped me to the bathroom and into the shower," the room is paid for, you can stay here tonight if you like."

"I'd like that, I don't think I could make it home right now anyway."

The hot water cascade down my body as I sat in the shower trying to wrap my head around what had happened; had I been raped, not really because I had let him tie me up willingly and even though the other men were a surprise, I had not objected and had in fact enjoyed what they did to me, the cum all over my stomach reinforced that. I finished cleaning myself off and climbed into the clean bed, Ted had gotten dressed, packed his things, and left.

When I woke up in the morning, I noticed an envelope on top of my clothes; there was money, a note, and a business card inside, he had thought I was a prostitute and I guess I had done nothing to disprove his theory. I read the note first," I'll be back in two weeks, text me if you're available," I counted out the stack of hundreds, what they had done to me was worth five thousand dollars.

There was a breakfast bar just off the lobby, I made myself a waffle and got some eggs and sausage as I thought about what I had done, looking around for Ted and listening for the other voices I had heard in the room, they were not here and possibly weren't even staying in the hotel. I thought about the soreness in my legs and in my butt, what it had felt like to be used like that and how I had cum over and over again while they did it. I counted out the money one more time, putting the business card in my purse.

The cab dropped me off at my apartment and I took another long hot bath, letting the lavender waft over me and sooth my sore muscles, I started doing the math in my head, if I could do this twice a month, that would beat my take-home income at the firm, and what if Ted had friends that liked the same things? I tried to chase the idea from my mind, but it just wouldn't leave me alone, it hadn't been that bad, after all and even Ted peeing in my mouth hadn't been totally gross. I refused to let myself acknowledge that I had enjoyed it, that was a step too far, at this point anyway.

The information Ted had shared ran through my mind, if that deal had come across my desk, I would have recommended it to every one of my clients, all one of them, and taken it upstairs to the partners; it was a great opportunity. I spent the entire weekend doing research on Ted and his company, finding that they were in fact in talks concerning a merger. It took an hour or so to find a low cost brokerage I felt comfortable using; I bought twenty thousand dollars' worth of Ted's company from my signing bonus and waited to find out if he was for real.

Monday, I polished off my resume and started trying to make contacts for a new position, nobody had any openings even though some of the companies had several openings listed on the job boards. Thursday, I had lunch with the handful of brokers from Jenkins and Jacoby that weren't under indictment discussing possibilities for employment. The new wasn't good, Even James, who had a ten-year track record, was getting shut down by his personal network; we were all effectively unemployable.

When I got back to my appointment, I took a hot bath and unpacked Elaine again, took out my phone and texted the number," This is Elaine, Yes."

The response was almost immediate, "Good, Thursday, 8, same hotel, I'll text you the room number."

I spent the entire week as Elaine, nerves from not being able to find work as a broker, bundled with more nerves for what I had agreed to do with Ted, I was actually relieved when his text came," room 308. See you tonight."

I spent the rest of the afternoon getting ready, long hot bath, shaving everywhere I thought there might even be the thought of a hair, makeup, and a slightly slutty outfit. When I knocked on the door, Ted smiled at me and led me to the bed. His friends were already here this time and there were five of them, six counting Ted. I could feel my stomach in my throat as I slowly undressed and slipped into the harness, Ted slipped on the blindfold and lubed my ass and it began, one after the other, they used me, filling my throat and my ass with their hot cum, these men were not being gentle and I began to realize this wasn't just about sexual gratification for Ted and his friends, it was about power, control, abject humiliation.

I started to focus on the conversations of the men that didn't have their dick in me at the moment, taking copious mental notes of the companies they talked about and the deals they were working on, smiling to myself as detail after detail of their busines dealings was offered freely. When they were done fucking me, Ted again helped me to the bathtub and again, was gone when I finished cleaning myself off. When I woke up the next morning, there was seven thousand dollars in the envelope by my clothes.

The talking heads on the TV were giving the financial news as I filled my plate with bacon and eggs, the story of the day was the merger between Ted's company and the mega conglomerate that was purchasing it. I checked my account and my shares were now worth over one-hundred-thousand dollars, I just smiled and enjoyed my breakfast.

The cab the doorman called for me had a sign on top for a fairly upscale spa, figuring I had earned it, I told the driver that's where I wanted to go, four hours later, I had enjoyed a full body massage with a body wrap, my eyebrows being shaped, the first course of electrolysis on my legs and arms, a delicious lunch, and had a recurring appointment every Tuesday and Thursday until there was no hair anywhere on my body below my eyebrows. Elaine had far more earning potential than Evan and I was discovering I liked the work a lot. It wasn't just the sex, I liked being dominated like that, besides, with the information I was collecting, it wasn't going to be very long before I could do whatever the hell I wanted. I spent a couple of hours perusing the shops near the spa and bought Elaine some nice outfits and several pair of new heels.

I was walking up the stairs to my apartment when my phone buzzed," Ted gave me your number, are you free tonight?"

"Yes, when and where," I had replied before I had even tought about it, the memories of how I felt as Ted and his friends used me excited me, I wanted more.

I knew the hotel, it was in Manhattan, very nice, and very expensive. I had three hours to get ready and get there. I opted for a traditional business suit, pencil skirt with a matching jacket, a see-through blouse underneath, and my sexiest lingerie under that, a professionally dressed woman met me in the lobby. A security guard at the elevators had to enter a code to get us to our floor, I stepped out into a large room with two poker tables in it, a large group of men milled around waiting for the game to start, my job was to serve as a hostess, making sure the players had fresh drinks and ashtrays were never too full, providing snacks and flirting a little for as long as the game lasted. Meagan provided me with a uniform, a halter top and a very short skirt, with garters and stockings, my black heels would work fine; should one of the players want anything else, that was between them and me and Meagan did not want to know about it, I could cash out any chips the players tipped me at the end of the game. There was a small room down a small hallway for the more intimate requests.

At first, nothing out of the ordinary happened, then a player at one of the tables went all-in, asking me to come stand by him for luck. I stood behind his chair and rubbed his shoulders as he waited for the others to respond to his bet, when no one answered, he slipped me a five-hundred-dollar chip as he stood up and kissed me, I wrapped my arms around his neck and responded, taking his hand and leading him down the hall to the small room. I saw Meagan smile at me as we walked by.