James' New Job Ch. 01

Employment prospects for a newly graduated media studies student weren't good. It was a cliche, I know and everyone I knew had joked about my employment prospects not extending much further than Starbucks or McDonalds once I left university but I had remained ridiculously optimistic and after three years of racking up eight thousand pounds a year of student debt something had to give.

I had finally given up on finding something actually in media and was now looking for anything that would pay a half decent wage. After a day's fruitless job hunting I was on my way home when I noticed a very upmarket looking hotel hidden away, just off a main road. I was pretty knackered and decided to pull into their car park for a ten minute rest. I got out of my car and strolled into the bar area and my jaw hit the floor. It was probably the classiest looking place I had ever been in with cool designer furniture and smoky, low lighting. I walked over to the bar and ordered a coffee (I probably couldn't afford much else) and settled down.

The barmaid who served me smiled and went out to the back to make my drink. As she walked away I admired the view. She was gorgeous, very trim figure but with a very generous and slightly out of proportion bust and nice tight arse with lovely copper, red hair, tied up in a loose ponytail. As she went out the back her male colleague appeared and if she was attractive, he was her male equivalent. I'd never looked at another man that way before but, honestly, he looked like he'd been chiseled out of granite with what looked like a rock hard body under his uniform. The two of them conversed with each other in hushed tones, occasionally looking over at me.

He caught me staring and smiled and asked how I was. I mumbled an embarrassed reply and went back to inspecting my fingernails!!

The barmaid brought my coffee back and laid it on to the bar with a smile that had me melting inside. "So, what brings you here then?" She asked.

Christ, she was talking to me, "I've been job hunting all day and I'm pretty knackered so I thought I'd have ten minutes and saw this place. I've never seen it before, it's pretty impressive."

"We've only been open six months, we're very exclusive, rooms here cost a fortune, how did the job hunting go?"

"Not very good I'm afraid," I replied, "lucked out all over, I've only recently left university and my great career plan hasn't exactly worked out so I'll pretty much take anything at the moment." The barmaid looked over to the other guy and gave a barely perceptible nod and he disappeared into a room behind the bar area, I could see him pick up a phone and have a conversation with someone then hang up. He came back out to the bar area and approached me.

"I'm Daniel," he said, extending his hand, "I couldn't help but overhear, we might have something here if you're interested, it comes with accommodation and the pay's pretty decent as well, I've just spoken to the manager if you want to meet him?"

I was so shocked I nearly fell off my chair, "really? I mean that would be great, er, what is the position?"

"Bar work mainly, but it's best if you speak to David, the manager first, although I think you might be just the person we're looking for."

A day earlier.

David, Daniel and Samantha were sat around a beautifully ornate, teak desk in David's office. David was busy on a laptop while the other two waited patiently for him to finish whatever it was he was doing.

"Ok, with you two and Rebecca and Paul we've bought in twelve grand this week, three customers each. Good work, but it could be better. I can't help but think we're getting a bit stale, vanilla. Samantha, remember that S&M party you organised three months ago? We made twenty four thousand in one night. That's what I'm talking about. The investors loved it and want us to do more of that, exploring different themes plus they want to maybe attend a few which would be interesting, I've never met any of them." He stopped and looked expectedly at the other two, "well?"

Samantha sat up, "Paul can do bi and gay if he needs to, Rebecca & I can do girls, but there is something we don't have."

The two guys sat forward.

"A tranny, chicks with dicks. She males or tranny's are a certain porn sites most popular search. Some straight guys travel thousands of miles to visit Thai ladyboys."

David interjected, "you're right, but they don't come cheap. Either of you know any? Cause I sure as hell don't."

Daniel shook his head, he didn't like the way this conversation was turning out.

Samantha saw the look on his face and laughed. "don't panic big boy, we need someone a tad more feminine than you. Right idea though, instead of forking out big bucks for the finished article, we'll just make our own, you watch, something will turn up."

Present Day

A few minutes later an impeccably dressed man in his late thirties came over to me with his hand outstretched. He took my hand in his in a firm but friendly grip and we shook briefly.

"Hi," he said, "Daniel tells me you might be looking for work."

I nodded my confirmation and proceeded to tell him about my lack of work opportunities, the student debt and my willingness to try anything. When I said that he looked up at me with what could only be described as a wicked smile. "Anything?"

I blushed "well, anything legal" and forced a rather pathetic laugh.

He looked at the other two (I'd learned that the girls name was Samantha), "well, these two love it here, Samantha was in a very similar situation to you three months ago but now she's earning over four hundred pounds a day and has nearly paid off all her student debt."

I nearly choked on my coffee, "four hundred quid a day? For bar work, really??"

David looked slightly guilty, "look, it's not all bar work, I'm not very comfortable discussing this here, why don't we go back to my office, Samantha, come with us."

The three of us walked through the hotel, past reception where another male/female couple, again looking like they'd just stepped off a catwalk, were checking in a very wealthy looking middle aged man.

We went into David's office where he went to sit behind a beautiful teak desk and Samantha and I sat opposite him.

"James, isn't it?" I nodded nervously, I didn't want to fuck this up.

"Ok, here's the deal. We cater to a very wealthy carefully selected clientele. Every single employee here including Samantha and myself are here to offer 'personal services' to the guests, if you know what I mean."

The penny dropped and I gulped and stared back at David, "you mean you're prostitutes?"

David smiled, "that's a very crude way of describing it, but yes, I suppose we are. The hotel is owned by a group of very wealthy investors but is more of a side business. The restaurant does very well, we have one of the best up and coming chefs in the country working for us and we have a three month wait for a table at weekends. There are other employees working here that don't do what we do, obviously, but the five of us bring in a very tidy sum for the owners. With the business being a hotel it's perfect for entertaining clients." He smiled warmly at me.

This is where I should describe myself. I was eleven stone wringing wet and about five foot nine so compared to the men I'd seen here so far I just didn't stack up, and that is what was bothering me. "David, look at me compared to Daniel and the guy on reception, what possible use could you have for me."

David smiled across at Samantha then back to me. "Recently, we've been looking to broaden our horizons and offer some other, more specialist services."He seemed to be struggling so Samantha stepped in.

"James, have you ever had gay sex?"

"What?? No, I haven't. Is that what this is? You want me for that?"

David came in then, "not strictly, Paul takes care of that for us, your slight build is what makes you perfect for this role. You see, more and more people, men and women, are asking us for sex with crossdressers or transvestites. The money they are willing to pay for the right person is staggering. We would like to discuss this with you." He could see I was in a state of shock so he didn't pause but carried right on, "We will offer you accommodation, a complete wardrobe, any assistance you might need plus," and here he paused for dramatic effect, "four hundred pounds a day."

I still couldn't speak. These freaks and perverts wanted to dress me up as a girl and have me fuck random strangers. I looked over at Samantha, "I'm sorry, but I really do think you've got the wrong guy, I'm sorry."

She smiled sweetly at me "I understand, I hadn't considered this line of work before I came here, I wanted to be a lawyer, but the conditions are great, they really check the customers and there's never any trouble."

"That might be," I said, "if I was going to be having normal sex with women it wouldn't be such a big deal, but you want me to have sex with guys, while I'm dressed as a girl, that's totally different."

"Not always with men," said David, "you'd be surprised how many women like their girls to have a bit extra. Look I'll tell you what, give it a go for a week, we'll only fix you up with women at first, if you're ok with it we'll introduce a guy or two towards the end of the week. If you're cool we'll carry on. If not we'll pay you two grand and we'll go our separate ways."

Two thousand pounds, WOW, that would make a big difference to me.

I looked over at Samantha who smiled encouragingly.

"Ok," I said, "one week, then we'll see."

David looked delighted. "Great, do what you have to do, then report back to Samantha here in a couple of hours, she'll get you settled in and get you ready. You're starting tonight."

Samantha looked me over, "when you get home, shave yourself all over, I want you totally smooth. You won't need many clothes, we'll have everything you need. You won't have any clients tonight but you will be getting a full makeover and, since it's my night off, we'll have a girly night out, just to see how you handle it."

She looked me over, weighing me up,I couldn't help but feel a bit intimidated, she rested her hand on my thigh and leaned in close, "I've always wanted to fool around with a girl like you," as she said 'you' she squeezed my thigh, "I think we're both going to have an evening to remember."

David stood up and ushered us both out, "see you in a few hours, I can't wait to meet, hold on, he needs a new name."

Before I could say anything Samantha chimed in, "Jennifer, Jenny, she's Jenny now."

Next chapter sees James become Jenny and she meets her first couple of customers.