The New Secretary

By: Anonymous


I had been looking for work in the want ads and noticed there
weren't many choices. Most of the jobs were menial labor or fast
food types and didn't pay much. But I did find a job opening
listed at a local law office. I circled the ad then drove down
to apply.

I entered the small out of the way building and noticed a stack
of papers and books on a couple desks in the main office. After
asking if anyone was in I heard a ladies voice. She told me to
come into her office. I entered to see her moving about the
paperwork while she talked on the phone. After she motioned for
me to take a seat I waited until she was done with her call.

"Can I help you?" She said with a smile. I showed her the ad she
had placed in the paper for a legal secretary. She took her seat
and looked me over as I handed her my resume.

"I do need a secretary very badly as you can probably tell from
the mess of papers and books in here" she said. "I know these
days that there are a lot of male secretaries out there and you
seem well qualified" she continued "but I am more in the market
for a woman secretary, it's more traditional, you understand."

I told her that I had a degree and would rather use my brain
than have to twirl either a spatula or a shovel. She seemed to
understand as I continued about really needing a job and after
I nearly begged for the chance she finally relented.

"You don't mind doing what is usually women's work then?"

I told her I didn't mind. With that she hired me and had me
report bright and early the next day.

It didn't take long to get the place in shape and within a
couple weeks I pretty much learned all I needed to know. I
worked at my desk answering the phone and typing reports in the
outer office and Donna worked in her private office. She was a
good lawyer, was in her early 50's or so and had a bit of a
buxom build. She was larger than I was and with me being
slightly built and short as well she was also a couple inches
taller. She often teased me that I should maybe wear high heels
around the office so I could be taller than her! I then thought
it a bit strange as I noticed that her clothing seemed just the
slightest bit masculine in appearance.

I passed the comment off until a couple weeks later. I had been
working there for a month and everything was rolling right along
when one Friday afternoon Donna called me into her office. It
had been a bit slow that week and it was nice to not have to
hustle quite so much and I thought that after the work got down
to a routine it would be a pretty good job, especially since I
was making about ten bucks an hour more than most any place else
in town. I went into Donna's office and after closing the door
behind me took a seat and awaited what she had to say.

I figured it might be some extra work, or maybe her thanking me
for getting everything caught up or maybe even her telling me I
could leave early for the weekend but that isn't what happened.
She rummaged through her desk drawer then brought over a small,
paper bag package and handed it to me. I opened the package and
reached in to feel something slippery and silky then pulled the
material out and noticed I was now holding a pair of ladies
panties! They were full cut, white nylon briefs and very
feminine all done up with lace and bows!

"What's this!?" I questioned with a funny look on my face.

"Just a little something for you Dennis" she said with a smile.
"I'd like you to start wearing them under your suit when you
report for work. And don't worry, I will pick up enough of these
pretty, feminine panties to keep you properly dressed from
Monday through Friday. You don't have to pay me for them,
consider them a bonus." She said as she returned to her desk and
took her seat.

I folded the panties and put them back in the bag. "I don't
think so Ms. Roberts."

She didn't like my apparent stubbornness.

"What did you say?" She said.

I repeated that I wasn't about to wear women's panties but she
only giggled slightly as she continued.

"I told you this was traditionally women's work didn't I?" She
said.

I said that I remembered that but continued on thinking she was
joking. I got out of my chair saying I had work to finish before
five o'clock but she replied by saying "you're not dismissed
yet! Pick up that package," she said with a demanding tone.
"Monday morning you will come to work and I will check to make
sure you are properly dressed."

I told her I wouldn't do it! She then ended the argument.

"You'll report to work on Monday wearing these panties under
your suit or you'll look for another job!" She said with
authority.

She relaxed a bit by telling me it really wasn't that big a deal
and that I would get used to it.

"I just like knowing my little secretary is dressed just a
little feminine underneath. And what's the worry? Who's going to
know?" She finished, then said I could return to my work.

I didn't know what to think! If I didn't do what she said I
would be out of a job and in a real jam! I quietly gathered up
the package then left her office closing the door behind myself
as I left.

I dreaded the following Monday morning. I got up, showered and
got ready for work. I took my suit off the hanger and grabbed a
fresh shirt and tie then noticed the package Donna had given me
sitting on the dresser. With no way out at least for the moment
I took the package, reached into it then took out the panties
and began putting them on! I finished dressing as usual and then
drove to work.

I entered the office and had just started for the coffee machine
to make coffee when I heard Donna call me into her office. I
entered the office and as I closed the door she was already
moving towards me asking how my weekend was. She then moved in
close and reached for my pants! I startled back. "Just relax
now, I'm not going to bite!" She said as I stood there.

She reached over and holding my belt with one hand unzipped my
pants with the other. She then reached in and felt the front of
the panties I was indeed wearing. She felt the creamy smoothness
and could feel the lace trim at the front and the little bows at
the front of the lace trimmed legs.

"Feel good don't they?" She said with a wicked smile as she felt
me through the panties.

Just as she started to stroke my member I pulled back and she
withdrew her hand and returned to her desk. I could feel my face
redden with embarrassment as I quickly zipped back up then
mentioned that I had coffee to make.

The morning went as usual until after lunch. Donna got back
about a half hour late and after hanging up her coat she smiled
and put another package on my desk as she left for her office.
I could tell the package was from one of the local lingerie
stores. I couldn't believe she was serious but realized she was
as soon as I looked inside and saw another dozen or so pairs of
ladies panties! They were in several pastel shades and all the
full cut type and all had lace and were adorned with appliques
and other lacy trim and little bows. I quickly closed the
package and put it in one of the desk drawers realizing that I
would now be wearing panties to work every day! I was a bit
sickened to see that the days of the week were embroidered on
one set of the panties as well when I got them home and took
them out of the package!

The next morning I was back in Donna's office for inspection.
She had me take my pants down this time and then rubbed her
hands over the cool, slippery pink fabric.

"My, you seem to like the pink ones hummm?" She said with a
giggle as she looked me over then pulled them up tight on my
waist and squeezed and rubbed my bottom through the shiny nylon.

I asked how it could possibly matter which color I wore and she
giggled, satisfied I was still following her orders.

"But there's one thing though," she said as she looked me over.
"I'd like to have you start shaving," she said as she saw the
sparse but noticeable hair on my legs. I felt shocked!

"Shave?" I said with a gasp.

"Yes, you'll look so much better in these when you are properly
shaved," she added as I pulled my pants back up.

"How much to I have to shave?" I asked in quiet terror.

"Everything silly!" She said with a giggle. "Tomorrow morning I
will expect to see you nice and smooth all over without a hair
below your eyebrows except for your 'bikini cut' down below" she
giggled at allowing me to keep a little hair.

I pleaded with her to not make me do this but she was insistent!
It was either that or get ready to start looking for another job
with what most likely would be a menial labor one with a lot
less pay! I quietly returned to my desk and finished out the
day.

The next morning it was inspection time with Donna again in her
office. This time she made me strip down to my socks and panties
while she looked my now totally shaved body over! Later that day
she called me in to her office once again and this time handed
me several pairs of nude, support pantyhose! I knew what was
next. Now in addition to wearing panties to work I would now be
wearing women's hosiery to work too! And the next day it was
another inspection. Donna noticed my panties under the shiny
nylon pantyhose as she fondled my now shaved and nyloned legs!

"Mmmmmmm, don't they just feel delicious?" She said as she
marveled at how the nylons shined in the light and how they felt
under her hand as she rubbed the material against my legs! I
started having second thoughts about continuing working for
Donna and even though I needed the job I thought about just
quitting while the quitting was good.

But as I finished pulling up my pants and tucking in my shirt
once again Donna told me she was giving me a raise for my being
a good secretary and such a good sport. She then handed me
another package and told me how nice I would feel with a
pedicure! Then once back at my desk I noticed the nail polish
and other do-dads in the package!

The days went by and with the workload I found I actually forgot
about the panties and pantyhose from time to time, just like
Donna had said by saying "don't worry, you'll get used to them
in no time."

With another week came another feminine addition to my lingerie
wardrobe, and then another, and another! The following Monday I
was standing in Donna's office before starting work while she
looked me over once again. By now, she really had me decked out!
I was wearing my panties and pantyhose complete with my now red
nailed pedicure done up in a bright gloss red that showed
through the toes of the stockings. She had also added a tight
girdle briefer panty to my wardrobe and showed me how she wanted
me to "tuck" myself so I wouldn't show a bulge. Finally, she had
me wear a pair of white nylon pants liners and finished the look
with a matching, lace trimmed nylon camisole! I was now,
underneath, totally dressed!

I begged her to let me take off the camisole saying the straps
would show through my shirt but she wouldn't have any of it! She
said if I was worried I should start wearing T-shirts and / or
keep my suit coat on at all times. I thought the next step was
the last straw though because the following Monday, she brought
a pair of high heels to work that were in my size!

The shoes were black patent leather pumps and Donna made sure to
get a pair with open toes to show off my painted toe nails! I
was grateful that most of our work was corporate and didn't
involve a lot of walk in traffic but I drew the line at wearing
high heels and complained immediately!

"What are you doing to me Donna!?" I asked with a quizzical
glare as I stared at her. But she only smiled with her usual air
of authority knowing full well who was in control.

"I thought you said 'who'll know' and that nobody could tell I
was wearing ladies lingerie? If I wear these shoes around the
office what happens when somebody comes in!?" I said in a
terrified tone. "They'll freak out!"

"Don't worry!" She said. "You just get yourself a pair of
loafers and keep them under your desk. Then, if someone comes
into the office you can change shoes without them knowing."

"But what about these nylons?" I said pointing to my ankles.

"Your pants are long enough, just put your dress socks in the
drawer until you leave at night."

She had it all figured out and even though I tried to argue
further it did no good. Then she told me If I could learn to
master the heels in a week she would give me another raise!

It became very strange almost surreal. She watched as I went
back to my desk and took off my wingtips and black dress socks.
My nyloned feet complete with red nail polish were now clearly
evident! And worse now because I was stepping into women's high
heeled shoes! Donna smiled with satisfaction at seeing them on
me.

She had to help me stand at first and giggled as I wobbled on
the five inch stiletto heels as I moved around the office doing
nothing more than trying not to fall. She had me continue to
practice and coached me how to step until I started walking a
little better. She then returned to her office. An hour later I
heard her ask me to bring her in a fresh cup of coffee. I knew
what she wanted, she wanted to see me mincing on the heels and
did just that as I carefully made my way into her office with
the hot coffee. Donna thanked me then watched as I teetered, the
heels forcing my hips into a slight wiggle as I moved back to my
desk. And that's how it went.

As the days went by I would put on the high heels immediately
after arriving to work and leave them on until my lunch break.
After lunch however, it was back in the heels! The following
Thursday I was just finishing putting away some files in the
cabinet and walking back to my desk. It wasn't five minutes
later that a gentleman came into the office wanting to talk with
Donna! I managed to slip out of the heels and put my new slip on
loafers on and then escort the man in to see Donna! After he
left I had to put the heels back on but I was shaken from the
incident and complained to Donna about it.

She then said we were taking the next week off! I asked why and
she replied "if you are worried about wearing the high heels we
can do something about it so you won't look or feel so out of
place. And since you're getting so good in walking in them it'll
be easy." She said with another of her smiles and finished by
telling me that I would be spending the entire week at her home.

I had an inkling of what was going to happen but not to the
degree it happened! I threatened to quit and didn't really care
but Donna was insistent and with an even larger raise being
offered I felt almost stuck somehow. The job wasn't that hard,
even in the heels but I knew after I was told the rest of
Donna's plan that I could never pull it off.

The first thing I was to do was pack up and move out of my
apartment. I would be living with Donna now and after she was
finished with me there would be no way I could really go back to
my place anyway. Then the next week passed, and with the fifteen
hour days and all the work it passed slowly! But soon it was
Monday morning and the start of another work week.

I was terrified to get out of the car when we pulled up to the
office but Donna insisted that I could make a go of it and that
no one would even notice my changes. I was just the "new"
secretary. I was nervous as I opened the car door and felt the
click of my high heels as they hit the pavement. I took my purse
and after leaving the car I made my way up the sidewalk with
Donna. I could feel my new bust jiggling and feel the cool
morning air swirling around my nyloned legs! And could hear the
swish of my nylons brushing my calves and thighs with each step
as I minced along in my tight, satin lined skirt on those five
inch heels! I saw a few people moving about and driving past on
the street but nobody pointed, or laughed or yelled out. I did
notice a few women give me a passing glance as they went about
their business and a few men looking me over as we made our way
to the office door.

Once inside I was now the "new" secretary and would be known as
Deborah. I hung my car coat up, set my purse on my desk then
went about my regular duties by making coffee. Donna looked me
over.

"Yes, you're a proper little secretary now, very nice, very
ladylike." Then, issuing a satisfied smile she went into her
office.

In being off for a week there was a lot of mail and paperwork to
file and catch up on. I finished with the coffee then swished
into Donna's office to deliver her cup. She noticed me mincing
on the heels, my shiny nylons swishing under my tight pencil
skirt and my bust jiggling under my satin blouse as I set the
cup on her desk.

"Thank you Deborah dear" she said as she casually went back to
work.

"Yes ma'am" I replied as I returned to my duties.

I sat down at my typewriter and was glad that Donna didn't have
my salon nails made that long. This way they were short enough
so I could still type. And I had a lot of correspondence to
answer and a lot of typing to do. So I set to work. A couple
hours later Donna left for downtown on a couple errands and I
decided to stay through lunch to stay safe at the office on my
first day totally dressed as a woman, and to get the extra work
done.

I took phone calls, answered letters and did my filing as usual
then noticed myself in the mirror at the new look Donna had
helped to give me. I ran my hands over my feminized form and was
astounded! She had dressed me from head to toe and from the skin
out! She had gotten me a complete new wardrobe so I would be
able to look like the perfect little feminine lady every day
around the office. She had corseted my waist, and gotten me a
well padded girdle that really widened my hips and rounded my
bottom, and I could feel the weight and jiggle from the silicone
breast forms that now sat snugly in the cups of my satin
brassiere under my lacy, white nylon full slip and my blue, long
sleeved satin blouse with high collar and large satin sash bow
at the front.

My eyebrows had been plucked into a high and feminine arch now
and my ears had been pierced. I could feel the gold hoops as
they dangled against my neck from under my long hairdo that was
now dyed a bright blonde and fixed in a feminine style that
parted in the middle and feathered away from my face in large
sweeping curls. I was slightly built and small in stature to
begin with but looked nothing like a man anymore and any
masculine nuances I had were now hidden by Donna's intensive
week long training session and any left over manly traces were
now totally muted, covered up and totally concealed by the
ladies clothing, hairstyle, makeup, perfume and jewelry.

The days and weeks passed. And although we had little walk in
traffic, no one ever suspected that I was a man. They simply saw
the name plate "Deborah" and behind the desk a feminine, shapely
lady going about her secretarial duties as the scent of perfume
hung in the air and the sound of swishing nylon echoed through
the office whenever I moved in my seat or crossed my legs!