Date: Fri, 14 Oct 2022 15:35:35 +0000 (UTC)
From: Rachelle Naughty <rachellenaughty@yahoo.com>
Subject: A Career Change Chapter 1

This is a work of fiction depicting sexual acts between consenting adults,
aged eighteen and over. There are no similarities to anyone real or living,
other than myself who is the main character, set in deep running fantasy.
There are depictions of unprotected sex and smoking. I do not condone
either, as each is an individual's choice. Constructive feedback welcome at
rachellenaughty@yahoo.com. Also, support Nifty with a donation if you are
able.


A Career Change
Chapter 1-The Offer

Why was I here? What could they offer me in a job at a hotel I thought to
myself? I made the effort to get there so I may as well see what they have
to offer. The instructions to enter were specific, park around the back, go
to the door on the left and ring the bell. The door buzzed open almost
immediately. I was supposed to be there at ten in the morning and I was
five minutes early for once. Once inside the instructions said to go left
to the elevator and take that to the third floor. Off the elevator to the
right and go to the primary office.

I introduced myself to the receptionist and she offered me a drink and gave
me paperwork to fill out. She would let Mr. Hutchins know I was there. I
took a seat and filled out the paperwork. I sat with a water and within 15
minutes the receptionist's phone buzzed.

"He is ready to meet with you now," she said, "this way please," as she
escorted me through the door to her right. Mr. Hutchins was on the phone
seated behind a large desk. He smiled and motioned to have a seat. I drew
up one of the leather chairs in front of his desk as he finished the call.

"Welcome. Thank you for coming to speak with us. Make yourself comfortable"
he said.

"My pleasure. I am curious when your assistant called and said you have a
job offer for me. I do not know anything about the hotel industry" I
replied.

"Yes, well this job is not exactly in the hotel industry per se though you
would work out of this building. We have several other lines of business
that we run from this building" he said. "Let me get to the point because
there is no straightforward way to get there. I understand you have a
penchant for older cock," he said with a sly smile.

"Ok...." was my only reply as I started to blush and squirm in the chair.

"We understand from online informants that you also like to dabble in
crossdressing" he said. "You go by the name, Rachelle?"

Wait, online informants I thought to myself. Does this guy call me here to
see if I will suck his cock while wearing lingerie? Rachelle? How did he
know? I started using that name as part of my want to be more femme, and I
used it with only a few men online but that was a year ago. I must have
looked very confused to him because I was.

"Let me explain" he said.

Mr. Hutchins went on with a detailed explanation of what one of their
businesses entails. At some point I zoned out but what I took from it was,
they employ a handful of crossdressers to work at various positions in the
business which centers on "entertainment" for their club members. There are
other businesses as well including an alcohol and tobacco business, high
end used cars, real estate, and various other entities. I came back to the
conversation after running through my head all the men I had met online and
who may have been an informant.

"So let me see if I understand this correctly, I come to work for you as a
crossdresser doing what type of entertainment exactly?"

"Well to be blunt, entertaining our older members. We need someone who
enjoys pleasing the older group. Then we would fit you in to one of the
other business lines. You can't submit on your tax forms you are paid to
have sex now can you. That would be questionable and illegal" he said with
little chuckle. "You could have multiple jobs depending on how motivated
you are. We would pay for all your transformation needs, your meals, and
lodging here at the hotel, you would live expense free. You would be an
in-house worker with some occasional outside work assignments, again,
depending on how far you go with it and how motivated you are. And your
salary would be genuinely nice, plus tips earned which are cash."

"May I call my transformation assistant in to do a quick meet and greet
with you?"

"Ah ok....," I stuttered out as I was having a tough time wrapping my head
around this concept let alone entertaining the idea of becoming an actual
crossdresser. Yes, I had a penchant for mature cock and yes, I sucked a few
while dressed up like that one guy who I wore panties for and blew him in
his shed. I tried makeup, a wig, and a dress at one point. I even had two
pairs of heels. It was difficult to pull that off at that time because I
was married. She didn't know. I gave it up because I was tired of trying to
hide it, and then we were divorced two years later. These days I have a
handful of panties and lingerie that I wear around the house.

"What do you have for me Jerry?" I heard from behind as I turned to see an
attractive girl walk through the door. Nice cleavage, short skirt, and big
hoop earrings. "This is Carla" Mr. Hutchins said.

"Hi...." I said as I stuck my hand out for an awkward handshake.

"We offered Rachelle a position. What do you think it will take to get a
basic transformation on her?"

"Stand up please" she said to me, "Turn around and walk away from me and
then back, please."

She said please, and I was stunned by what was taking place, but I obliged
her request. I thought about getting up and walking out but I did not. Was
I seriously thinking of this? Why was my little cock twitching?

"She needs a full and complete make over. The scruffy beard needs to go,
but it isn't that long anyway. Heel and makeup training as well. When was
the last time you took a big cock or dildo in your ass?" She asked.

I blushed when she asked me that.

"I don't think I ever had a big cock in my ass, but I have been using a
dildo on myself" I replied.

"We need to train that as well. I would say two weeks to get her to a
better than she looks now. Being closer to passable......longer than that,"
she said.

I knew that was true. I was never passable when I dressed in the real
world. Even with a clean-shaven face, I have a male body, I cannot deny
that.

"Thank you, Carla. Rachelle and I are going to talk some more and if she
takes the position, which I hope she does, then I will send her to you"
Mr. Hutchins said.

With that Carla said, "It was nice to meet you," and walked out.

"What do you say Rachelle? Stay for two or three months, let Carla work
with you and transform you. She can bring the girl out in you. You can live
your fantasy here and earn an income. We will pay you from the moment you
say yes to staying. Safety is a number one priority for all our girls. The
members are tested regularly so you need not worry about STDs, and we have
a doctor on call for health issues. We cover all your medical needs,
including vision and dental" he said.

"What are we talking about salary wise." I blurted out. What am I saying I
thought to myself? Was I seriously considering this?

"Well, the last girl in this position I know made six figures in her first
year. She was motivated and worked hard. Her part time job here was eight
hours a week and she worked in our cigar bar. She worked happy hour and
lunch time even after being here for five years. She developed quite a
following and had a few regulars who were well off. After she had implants,
she left us to do movies. We were sad to see her leave" he said.

Implants I thought. "Happy hour and lunch time?" I said quizzically.

"Yes. Lunch time and happy hour. It is amazing how many members need a
quick relief when they can't get to the club. We have an impressive set up
on the first floor, where you entered the building. Clean, discreet, and
safe. You would love it I am sure and do quite well at it. From what our
informants tell us, you love to suck cock. When was the last time you
sucked a cock, Rachelle?" he asked.

I had to think, but it had been sometime. "I don't recall, at least two
years" I replied.

"Don't you miss it?" he asked.

I do but I put it out of my mind. I thought. I didn't answer him, other
than shrugging my shoulders.

He called out to the receptionist. "No calls or visitors for an hour. Come
with me, let's have a real talk." He motioned me to get up and following
him. We sat on the large leather couch at the far end of his office.

I was nervous and he sensed that.

"Do you mind?" he motioned as he pulled a cigar from a humidor sitting on
the end table.

I shook my head indicating I didn't mind. The aroma of a good cigar drove
me crazy. I had fantasized about blowing a guy smoking a cigar. I had
smoked several of them myself in the garage back in the day wearing
lingerie or torturing my nipples. I would usually drop a big load that
way. Soon the pleasant aroma of cigar smoke filled the air.

"I understand that all of this is a lot to take in" he said

"To say the least" I said with a chuckle.

"I think you could do well here. Try it. Give us two or three months and if
you don't like it, you can leave whenever, but after that time I think you
will enjoy what we offer, and you will be very satisfied" he said with a
wink.  This offer, along with the aroma of a good cigar, had my little cock
twitching.

"What about the legality of it?"

"No worries at all, it is a private club, and we have politicians, judges,
and police who are members" he replied.

"What about my townhome, my car, everything in the outside world" I
asked. Granted, I had no kids, no pets, no spouse, or significant other.

"Well, your car is here, and you can use that whenever you like. You could
even go home and work from here, but I don't think you are ready to be
Rachelle out there" he said, motioning to the window. "We can take care of
all that. Don't worry about it" he said as he moved closer to me.

I didn't really get a good look at his body before as he was seated behind
the desk. He was attractive, and certainly a man I could be attracted
to. He was in his late fifties or early sixties I guessed, graying hair and
short trim beard, not fit but not too heavy. I felt extremely nervous as he
took my hand and put it on his crotch.

"Why don't you show me what you like?" he said.

My hand squeezed his cock through his pants. I did not say anything as I
was in a trance. It had been sometime since I had a cock in my mouth. I
slowly sank to my knees in front of him. He was wearing suit slacks, shirt,
and tie. My hands undid his belt and zipper, I unbuttoned his pants, and he
raised his hips as I slid his pants and briefs down.

His cock popped out from under his briefs. It was semi erect, cut and a
nice looking one at that. I took it in my hand and stroked it a few times.

"Lick it" he said, "You know you want to."

I moved my head towards his cock as it began to grow. My mouth
instinctively moving towards it. This is what I love, this is what I need I
thought to myself. This is where I belong. My tongue contacted the mushroom
head. My mouth was dry from being nervous. Mr. Hutchins could sense that,
and he stopped me. He spat into his hand and rubbed it on his cock.

"Now suck it," he commanded.

His spit was very slick from the cigar smoke, and it tasted just like a
cigar. My cock twinged when I tasted that. I moved my head slowly further
down his shaft. I heard a slight moan from Mr. Hutchins. At least I knew I
still had it.

After a minute or two of sucking and bobbing up and down on his cock,
Mr. Hutchins said, "You are good, I would love to have the real Rachelle do
this, and more. What do you say, give us a chance, stay and let's see where
you can go with this. Like I said, you can leave whenever."

"Ok, two months sounds reasonable" I replied. I could use the money I
thought since I have been out of work for three months and unable to find a
job. I continued with the task at hand, satisfying Mr. Hutchins until his
creamy load filled my mouth.

"Swallow every drop Rachelle" he said. And I did.