The Office Swap
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The Office Swap free porn video
I hung up the phone and exhaled. Another disaster had been averted. It
seemed my days were filled with solving one crisis after another. It
wasn't really what I had planned when I started my business, but it was
my reality. I owned a Porsche, lived in a penthouse condo, and my
venture had enjoyed four straight years of double digit profit
growth...and I didn't enjoy any of it.
"Jacqueline, can you bring me the Cooper file?" I called out to my
secretary.
"Of course, Mr. Jacobs," she replied and quickly entered my office. As
always, I tried to make my ogling not obvious. She was not a dainty
woman, but god could she package it. Today she had a tight white skirt
that ended just above her knees, a navy blue satin blouse unbuttoned
enough to show the lacy bra beneath, shiny pantyhose, and sky high white
pumps. As usual, she caught me looking, and I quickly turned my gaze to
her face as my own flushed. She smiled. She knew what her wardrobe
did.
She handed me the file and paused.
"Mr. Jacobs, is everything okay?"
"Just the normal chaos. Why do you ask?"
"Well, you seem so stressed. Is there anything I can do?"
"Thank you, Jacqueline, but it's just the nature of the job." I paused.
"There are days when I just don't want to put out fires. Honestly,
there are often times that I'm envious of your job."
She laughed. "I'll trade you any time, sir."
"I didn't mean to insult....."
"No, I understand. Have you considered selling the company or hiring
someone to run it?"
"I have, but I do like what I've built. I'd like to stay involved, just
not making all the hard decisions. I hadn't thought of bringing someone
in...it would be a huge learning curve for someone unfamiliar with our
process and clients."
That was when the idea germinated. Jacqueline had been with me almost
since day one and knew as much about the business as I did. I owned a
shipping brokerage. I arranged for large freight to be moved around the
world. As such, I had a very profitable business with just one
employee. Dealing with shipyards, dock workers, and such, my business
partners were very blue collar. Most of my clients were eastern
European and not overly "enlightened." You wouldn't find them at a
gallery opening or wine tasting.
The next morning I called Jacqueline into my office. Her attire was a
black sweater dress that hugged every curve and a pair of knee high
black boots with a five inch heel. I asked her to sit.
"Jacqueline, how would you like to be president of this company for two
years?"
She stared at me for a moment then said, "Sir?"
"I'm serious. You know all our clients and contracts. It would be an
easy transition, but there is a substantial challenge."
She was a smart woman. "Our vendors and clients would not accept
dealing with a woman."
"Correct."
"But you're offering me the job any way?" she asked.
I was silent and let her figure it out on her own.
"If I were a man....." she said.
"Yes. I'm not saying sex change. Just live as one. Essentially take
over my life, and I'll take a vacation from...me. Some minor and
reversible surgery, hormone treatment, and there are services to teach
you the skills." She looked down at her spectacular breasts when I said
"minor surgery."
"I'm asking you to do something huge and life changing so take all the
time you need to consider it."
"I'll do it," she said.
"That quickly?"
"You're offering me your 'life' of business owner, fancy car, great
home, and I do the books. I know how much money you make. If I have to
be a guy to get all that, then sure. What are you going to do while I'm
being you?"
"Well, as I said, I want to remain involved so I figured I'd be your
secretary."
She was quiet for a moment, and I could see she was thinking.
"Sir? You mentioned our vendors and clients?"
"Yes?"
"They'll only accept doing business with a man, and they're not going to
accept me as man enough if I have a male secretary."
She was right. As sexist as it was, it was the reality. I hadn't
considered that. Plus, I'd closed more than one deal because the client
was staring at Jacqueline the whole time.
"Well, I guess that won't work then," I said.
"Why not?" she asked. "You're asking me to be a man...."
"You want me to live as a woman?" I asked.
"Seems fair," she said. She had a point.
"Okay then. It's worth it for a break from my life. Plus, it should be
an interesting sociology lesson."
"When do you want to start this?" she asked.
I stood and gestured toward my plush leather seat. She rose and came
around the desk and eased into the chair. She sat for a moment then put
her feet up on my desk.
"I could get used to this," she said.
"May I get you anything Mister Brady?" I asked with a smile.
"A cup of coffee would be great......Brandi." My first name was Brandon
so I guess I was going to be Brandi.
There were arrangements to be made for the gender swap, but we traded
lives that day. She drove my car home to my house. I took her little
compact to her apartment. I wandered around "my" apartment looking at
the makeup and hair care products, the closet of dresses, skirts, and
blouses, and all the shoes. It didn't seem she, or now I, owned a pair
of flat shoes. And the drawers of lingerie I would kill to see her in
were now...mine. I had never had a crossdressing thought or urge in my
life, but I was mesmerized and more than a little turned on by the
thought of wearing all these things. Might as well get used to it, I
thought to myself.
I undressed and picked a pair of blue satin panties. They were so cool
and soft as I slid them on. I found a nightgown and shivered as it
cascaded down my body. I sat down at her computer and got to work
researching male to female conversions. While I found a lot of porn, I
discovered some useful sites and information. By the end of the
evening, I had a plan and several reservations for both of us. I also
found a site that sold hypnosis tracks to help ease the stress of
transition. I downloaded all of them.
I fell asleep, in my satin nighty, listening to a soft soothing voice.
"You are a woman. You are beautiful and love your femininity......"
The next morning I was sure to get to the office early. Didn't want to
be late on my first day as secretary. It was such a relief entering the
building knowing I would not be dealing with crises or irate clients. I
made coffee and was sitting at Jacqueline's former desk outside my
former office. I was dressed in my normal attire of slacks and button
down shirt.
Jacqueline came through the door, and my mouth fell open. She had cut
her beautiful mane of hair. It was buzzed on the sides and the longer
top was parted to one side. She was wearing one of my suits and a bold
red tie. While she did not look like a man, she certainly looked
masculine. Her bountiful breasts must have been taped down or something
because there was only a slight indication in her crisp white shirt.
She walked right past me into her office.
"Bring me coffee, Brandi," she called.
"Right away, Mister Brady."
She was looking at the daily reports when I brought her coffee in.
"Thanks," she said without even looking up. I lingered. I could smell
her cologne.
"Do you need something, Brandi?" she finally asked. I felt very much
the subordinate.
"Well, I, uh, was wondering how your first night as a man was." I
stammered. I was suddenly nervous standing in my own office.
"It was great. I love my new place." She took a can of chewing tobacco
out of her pocket, put a big dip in her lip, and grinned at me.
"You can go now, Brandi."
"Uh, yes, sir." I returned meekly to my desk.
Later in the day, she summoned me in. Her feet were up on my desk. She
casually leaned over and spit in the garbage can.
"Have you made all our arrangements, Brandi?"
"Yes," I replied.
"Yes, what?"
"Yes, sir, Mr. Brady."
"I expect a proper degree of professionalism in the office, Brandi. Now
refill my coffee."
I had always treated her with respect and courtesy, and I was being
chastised now. I wanted to put my foot down and say I could stop this
charade at any time, but I felt....submissive. She was so forceful. I
brought her a fresh cup of coffee.
We did this for a couple weeks until everything was ready. I would go
home at night and put on nylons and practice walking in heels. I sent
an email to all our clients announcing that I was taking a leave of
absence and that my associate Jack Brady would be operating the company
while I was away. I also informed them that, given it was our slow time
of the year, the offices would be closed down for a month for holiday,
but that Jack would be available by email if they had need. Each night
I fell asleep listening to my files....."You love being a woman. You
love fashion and makeup and high heels."
We each checked into a private medical facility. It had taken some
"funding" of their research, but she was getting a mastectomy, and I was
getting breast implants. We would both be put on hormone treatments.
From there, we would each go to what amounted to a finishing school.
She would learn to be a man; although she seemed to have a pretty good
start. I would learn to be a woman.
I arrived at my school dressed and appearing as a man except I had a
pair of D cup breasts I was so self-conscious of. I was greeted by a
very attractive woman. Her hair and makeup were flawless, and she was
dressed in all black.
"Welcome, Brandi. I am your Mistress."
"Hello, uh, Mistress. Pleasure to meet you." I extended my hand, and
she ignored it. I was led to my room which was decorated in all pink
and lace then immediately taken to a room fully equipped as a salon.
After undressing, as ordered, I put on a pink satin robe. My whole body
was waxed. My hair was colored and given extensions. My ears were
pierced. My nails were given a long, French tipped manicure. Makeup
was applied, and mistress explained each step as she did so. Finally,
mistress ordered me to stand in front of a mirror.
I gaped at the goddess staring back at me. Her honey blonde hair hung
down well past her full breasts, and her face was gorgeous. I raised my
hand to my mouth, and my reflection did the same. I looked at my
slender hand and my elegant nails.
The next weeks went by in a blur. I spent each day doing my hair and
makeup, walking, sitting, learning to hold my hands out with bent
wrists, picking out outfits, looking at fashion magazines, and
practicing speaking in a high, breathy voice. Each day I donned a
corset, and mistress tightened it until my figure was a perfect
hourglass. The hormones were beginning to take effect, and my butt was
becoming plump and curvy. My appearance, movements, and mannerisms
became that of a woman. I felt confident that I would be undetected
during my two year sabbatical.
In the third week, mistress summoned me to her office. I entered,
strutting confidently in my five inch heels. She inspected me as she
often did. My hair was in a soft updo, and my makeup was perhaps a
little dramatic for daytime, but it was expertly applied. My outfit was
a sheer white blouse that clearly showed off my lacy black bra, a tight,
above the knee, black pencil skirt, shiny black stockings, and black
patent pumps. My jewelry was big silver hoop earrings, and a diamond
pendant that nestled in my ample cleavage.
"Well done, Brandi," she said.
"Thank you, Mistress."
She gestured for me to sit. I did so, smoothing my skirt and crossing
my legs, being careful not to snag my stocking. Mistress smiled.
"How do you feel, Brandi?"
"Good. I'm confident I can pass as a woman."
She frowned at that.
"Do you feel feminine, Brandi?"
"It's hard not to looking as I do, Mistress."
"No. I mean do you feel that you are a woman?" she asked.
"Of course not, but that's not my objective," I replied.
She congratulated me and wished me well. We hugged and air kissed so as
not to smear our lipstick.
I returned to my apartment and went thoroughly through all of my
clothes. I was a little smaller than Jacqulyn so some would need to be
tailored. Her tastes were a bit more provocative than I would have
preferred, but on my new secretary salary I couldn't really afford a new
wardrobe. I giggled at that thought. I was just a secretary now. No
more constantly checking email and taking calls at all hours of the day
and night. I put on some satin pajamas, poured a glass of wine, and
binge watched Real Housewives. I had become a fan while at Mistress'
home.
My alarm went off early. I had learned how long it took for a woman to
get ready in the morning. Hair and makeup finally done, I stood in my
closet pondering what to wear. I decided on a coral skirt suit I had
always liked on Jacqulyn. The skirt went to mid thigh and the jacket
had just two buttons so it did little to cover my cleavage. I put it on
over lacy white lingerie and suntan pantyhose. Pearl earrings,
necklace, and white pumps completed my look. I confidently walked out
the door with a strut in my step.
A man was coming up the walkway, and he stopped and stepped to the side
to allow me to pass. He was wearing a golf shirt, and I noticed how
muscular his arms were. I found it odd that I would notice that.
"Thank you," I said in my breathy voice.
"My pleasure. I saw you coming out of Jacqulyn's apartment. Are you
staying with her?" he said.
"I'm a friend of hers. She's traveling for an extended period and said
I could stay here so she doesn't lose her lease."
"One beautiful neighbor replaced by another. I'm a lucky man. I'm
Rob." He extended his hand. I placed mine softly and horizontally in
his as I had been taught.
"I'm Brandi. Nice to meet you, Rob. I've gotta get going. Don't want
to be late on my first day."
I could feel his eyes on me as I walked away. I knew I was attractive
and that I was dressed how a man wants a woman to dress, but it still
was a strange feeling to be an object of desire. My next lesson in
womanhood came when I discovered how difficult it is to drive in five
inch heels. I ended up taking them off and hoping I wouldn't get a run
in my nylons. Note to self, I thought, put spare nylons in purse.
I entered the office almost giddy. All I would have to do today was
answer the phone, file, and maybe type some reports. The coffee was
ready, and I was sitting at my desk filing my nails when he arrived.
There was still the basic look of Jacqulyn, like he could have been her
brother, but he was all man. He had a five o'clock shadow on his strong
jawline, and his tailored suit showed off his broad chest and big arms.
He also had a substantial bulge in his pants. I blushed and looked
away.
"Hello, Brandi. Welcome back," he said in a deep voice.
"Thank you, Mr. Brady," I said and looked demurely up at him.
"Grab me some coffee and come in so I can get a look at you."
I brought his coffee in and stood while his eyes roamed up and down my
body. The way he looked at me, as if he had every right, was so
assertive, so masculine.
"Well, I have to say, Brandi, you are one gorgeous woman."
"Thank you, sir." I could feel my face flush.
"Blushing. Cute," he said and laughed. He was so condescending, so
self assured.
I went about my secretarial duties, refilling his coffee, bringing in
files, and such. It was such a relief to hear him on the phone with
angry clients and know I didn't have to deal with it. Yet, he seemed
perfectly fine with it. He was so in control.
In the afternoon, a big, fat man with tattoos up and down his arms
entered the office. He was the foreman of one of our dock crews. He
openly stared at me, fixated on my breasts. I self consciously tugged
at my suit jacket, but it could not cover the lacy bra or my breasts
spilling out of it.
"Hey there, sexy. Is Jack in?"
Did he just call me "sexy?" I was furious, but I knew it was not my
place to challenge him. I stood and went to Mr. Brady's office.
"Mr. Brady, Carl from the docks is here to see you."
"Send him in, Brandi."
Carl slapped my ass as he walked past me. Mr. Brady didn't reprimand
him. He just laughed. I returned to my desk. I could hear them
talking about what a fine piece of ass I was.
At the end of the day, he called me into his office. He had removed his
suit coat and loosened his tie. His feet were up on his desk. I
considered how quickly my frame of reference had shifted that I
considered it his desk. He was sipping a glass of bourbon.
"Please, have a seat, Brandi."
I sat and crossed my legs. His eyes were drawn to my sleek legs, and I
coyly ran my nails up my nylon. I knew the power beautiful women had
over men, but I was surprised I was having the effect on him. Was he
attracted to women now?
The answer to my question walked in the door. An attractive brunette
woman in a chartreuse silk wrap dress and fabulous strappy heels stood
there. He rose and went around the desk to greet her. He wrapped his
arms around her and kissed her deeply. I stared, unable to look away.
"Carol, I thought we were meeting at the restaurant," he said.
"I was in the area so I thought I'd surprise you, darling."
"Carol, this is my secretary, Brandi."
I rose and extended my hand.
"Pleasure to meet you, Carol. I love your shoes!"
She surveyed me then ignored me. I was just a secretary.
"We should go, darling. We have reservations."
I was left to straighten up the office and lock up. My head was
swimming. Jacqulyn was dating a woman? I guess the testosterone was
really working on him. While I had noticed my new observations of men,
it had not crossed my mind to date one.
At home, I kicked off my heels and prepared a salad for dinner. I had
quickly learned that keeping a figure like mine required constant
attention to my diet. The new issue of Cosmo had arrived, and I was
flipping through the pages when my doorbell rang. It was Rob. He was
dressed in tan slacks, a crisp white shirt, and a navy blazer. I was
again confused about my attention to wardrobes. He grinned and I could
see his pearly white teeth.
"Hey Brandi. How was the first day?"
"Oh, it was fine, thank you." Standing in just my stocking feet, I
noticed how much taller he was. I felt small and vulnerable.
"I'm going down to the pub for a drink and thought I'd see if you'd like
to join me."
"Thank you, but I'm pretty tired."
"Aww, c'mon. Not like it's a date or anything...unless you want it to
be." He grinned again and winked at me. I didn't want to, but he was
so confident, so assertive, and I submissively nodded.
"Let me get my shoes and purse."
It was just around the corner so we walked. My heels clicked on the
sidewalk. I could tell Rob was quite pleased at the looks I received.
My second night living as a woman, and I was already someone's arm
candy.
In my tight skirt and heels, I could not figure out how to get onto the
bar stool. Rob put his hands on my waist and effortlessly lifted me up.
I tugged at the hem of my skirt that had ridden up. He asked me what
I'd like and ordered for us, a dirty martini for me and a scotch on the
rocks for him.
Holding up his glass, he said, "Cheers and welcome to the neighborhood."
I touched my glass to his and took a gulp to calm my nerves. I left a
pink lipstick stain on the glass. After a few sips, I relaxed a bit,
and we chatted. He was funny and charming, and we laughed through two
more rounds of drinks.
With my decreased body mass, the three martinis had me a bit drunk. Rob
offered me his arm, and I held it to steady myself as we walked home. I
could feel his bulging bicep. At the door to my apartment, he turned to
face me. Even in my heels, I was still a couple inches shorter than
him, and I looked up into his blue eyes.
"Thank you. I had a wonderful time," I said.
He leaned close to me. I could smell his musky cologne. I knew what
was about to happen, but I made no effort to stop it. His arms wrapped
around my waist, and he firmly but gently pulled me against him. His
lips touched mine, and he kissed me softly and then more forcefully. My
lips parted, and his tongue entered my mouth. I was standing in a skirt
and heels kissing a man. What was I doing?!
I pulled away from him, stammered a good night, and quickly went inside.
What was happening to me? I stood in my little apartment and started to
cry. I'm Brandon Jacobs, I thought to myself. I'm a heterosexual male,
and I'm a successful businessman. The image in the mirror suggested
otherwise. I decided my vacation from my life was not such a good idea
and that I'd end it tomorrow.
The next morning I put on one of the few pairs of slacks I owned. Even
those hugged my curves and flaunted my plump ass. I did not own any
flats so I still had to wear black stiletto pumps. I put on a white
cotton blouse and buttoned it all the way up. I pulled my hair up into
a tight bun. I didn't want to, but I still put on my makeup. I was
conditioned.
He was already in the office when I arrived. I walked in his office
determined to end the charade, but he looked up at me and spoke before I
could.
"Brandi, what are you wearing?"
I wanted to say "whatever I damn well please," but under his stern gaze
I stopped and crossed my arms across my breasts.
"Brandi, you represent my company, and I and my clients have
expectations about how a secretary should appear."
"But...." I began to say, but he interrupted me.
"Go home and consider if you want to be a proper secretary or if I need
to find a new one."
Find a new one? My company? Who the hell did he think he was?
"Do you need money for some new clothes?" he asked and pulled a few
hundred dollar bills from his pocket. He slid them across the desk. In
his expensive suit, power tie, and gold cufflinks, he looked every bit
the successful businessman. I was just his secretary.
I meekly picked up the money.
"Thank you, Mr. Brady."
I parked my little car at my apartment complex and sat in it sobbing.
Finally, I got out and headed for my door. Of course, Rob came out of
his apartment right at that moment. I was a mess. My mascara was
running down my face, and I was wearing that hideous outfit. I rushed
inside, avoiding eye contact.
I completely undressed except for my panty gaff, let my hair down, and
looked at myself in the full length mirror. Even with my messed up
makeup, a beautiful woman with lustrous hair, full breasts, an hourglass
figure, and sleek legs looked back at me.
"I'm Brandi Jacobs. I'm a beautiful woman. I'm a secretary."
The phone rang. I answered, and it was Rob.
"Hi Brandi. I had Jacqulyn's number. You seemed upset just now. I was
worried. Are you okay?"
He was so sweet.
"Thank you so much, Rob. Just a problem at work. And I'm sorry about
last night."
"No need to apologize. I rushed you," he said.
God, he knew exactly the right things to say!
"Uh, Rob, would you like to come over later?" I asked in a sultry tone.
We agreed on six p.m. I hurried to get dressed. I had some shopping to
do. I strutted out the door in a white mini skirt that barely covered
the lace tops of my suntan stockings. My yellow spandex blouse flaunted
my breasts and perfectly matched my yellow platform peep toe pumps. My
long blonde hair flowed as I walked.
"I'm Brandi Jacobs. I'm a beautiful woman."
The doorbell rang at promptly six o'clock. Rob stood there in black
slacks and a powder blue shirt with open collar holding a dozen roses
and a bottle of wine. I smiled as his mouth fell open looking at me. I
had spent Mr. Brady's money well.
My beautiful hair was piled on my head. My long false lashes drew
attention to my smoky eyes, and my deep red lips were pouty and
kissable. My lacy black bra and matching garter belt were not at all
hidden by my sheer, feather lined black robe. I could feel the tug of
my garter straps, holding up my silky black stockings, as I went to him
and kissed him deeply, sucking on his tongue.
"Thank you, darling," I said and took the roses to put in a vase. He
stood in the doorway still stunned. I smiled at my feminine power.
"Do come in, darling. Open the wine for us."
I curled on the couch and sipped my wine. Rob sat next to me softly
caressing my stocking covered legs.
"Kiss me," I ordered him, and he quickly complied. His hand slid up my
silky body to cup my breast, and I let out a small gasp.
"You are so incredibly beautiful," he said as he nibbled my ear. I
moaned softly, and I could see the erection build in his pants. I
reached out my hand, in its elbow length satin glove, to softly caress
his crotch. I was a goddess, fully in control, and I wanted him aroused
beyond the point of no return when I told him my secret.
We kissed for a while as his hands caressed me. I unzipped his pants
slowly, teasingly slowly as I looked in his blue eyes. I pulled his
hard cock out and stroked it softly with my satin glove. He groaned. I
smiled. I did know what men liked.
"I want you so bad, Brandi."
"I know, darling, but there is something I have to share with you." I
stroked him some more. It was the first time I'd ever touched a man's
cock, and his was big, but it felt natural and normal to do so. After
all, I was a woman.
I continued to stroke him as I leaned in and whispered in his ear.
"Rob, darling, you should know that I am a trans woman."
He pulled away, looked at me, and laughed.
"Yeah right," he said. I continued to stroke him.
"It's true," I said and slowly stood. I slid my hands over my breasts
and down to my panties, letting him soak in my beauty, then slowly slid
them down over my hips. They fell to the floor, and my small but
aroused cock sprang up. He stared at it then looked up at me. I batted
my lashes, and the expected response came.
"Brandi, you are the most beautiful, sexy woman I have ever met. I've
never been with a trans woman, but there is a first time for
everything."
I sat on his lap, feeling his hard erection on my ass, and I wrapped my
arms around his neck.
"Make love to me," I said.
He lifted me and carried me to the bedroom.
The next morning, I was at my desk when Mr. Brady arrived. He looked so
handsome and authoritative in his suit and tie. He paused to inspect
me. My breasts strained against my tight pink satin blouse and my
nipples pressed through the flimsy material.
"Come in my office, Brandi," he said, and I wiggled in my tight little
skirt behind him.
His eyes roamed over me with approval and a hint of lust. I posed with
my hand on my hip for him.
"I approve," he said, and I beamed.
"Thank you, Mr. Brady! I love being your secretary." It was not long
after that my duties were expanded to "providing stress relief" as he
called it. As he would bend me over his desk and lift my skirt, I would
wiggle my ass for him. He was such a strong and important man with such
a demanding job. I was very happy I could provide him with relief.
Cathalina
- 26.09.2020
- 16
- 0
