When I left school the orphanage found me a job as an office
boy, where thehs. boss had a spare room that I could lodge in for a
couple of mont

When I started work I found out that all the rest of the office
workers were women. I soon settled down and found that they were
all nice to me.

There was one woman Marie who was slightly older than me,
we chatted at lunchtime and during tea breaks. As I was the only boy
the talk soon got round to as to whom were the brightest and
cleverest boys or girls.

One day the subject got round to how cleaver women were to be
able to suddenly walk correctly in high heel shoes, and that boys did
not have the balance or dexterity.

We bantered about this for a couple of days until Marie said that
a boy could not learn to walk in heels, in their defence I said that
they could if they wanted to. She then bet that I could not learn to
walk correctly in heels before their next office party. Marie said that
every two months they all went out on a Friday evening for an office
party and they were going to one this Friday.

Marie then said if I could walk correctly in 4inch heels by the
time of the next party then they would all pay for my meal, if I could
not walk correctly by the time of the party then I would have to buy
them all drinks.

I took on her bet not knowing how far it would go.
The next day she appeared with a pair of 2inch high heel shoes
saying I would need to learn in lower heels before trying the 4inch
heels. Marie then gave me a pair of knee high stocking to wear with
the shoes. When the tea break came they got me to take off my
shoes and socks. I then put on knee high stocking and shoes. When I
looked round they had taken my shoes and socks saying they would
give them back at the end of the day. They then had me try to walk
around, I staggered around for a while and the sat down to finish my
break. After the break all my jobs seem to entail standing filing or
walking around. As I passed anybody they kept making remarks that
they were looking forward to their free drinks.

Marie told me during the lunch break that my problem was that I
was trying to walk as a man with large steps and not small steps that
are required with high heels. They then all kept on to me to take
smaller steps, as much as I tried after a couple of small steps I was
back to larger ones. During the afternoon a noticed that they all
seemed to be discussing me. At the end of the day they returned my
shoes and socks and enquired if I thought that I would be able to win
the bet. As she left Marie said that she might have the solution to my
problem and she would try to help tomorrow, She said that I should
get to work a few minutes earlier.

When I arrived the next day Marie and a couple of the others
were already there and the told me that there solution was that I
should wear a straight skirt with Hold up stockings instead of my
trousers. I was to go behind the filing cabinets and take my trousers
off and put the stockings and skirt on, I tried to protest but they said
they would remove my trousers themselves if I would not.

I went behind the filing cabinets and did as they suggested. I
came out with the straight skirt, stockings and shoes on, they took
my trousers shoes and socks away and said I could have them back
at the end of the day.

I did find that having the straight skirt stopped me from taking
long steps and I was getting better at walking in the shoes. After a
couple of hours the boss came out and saw me and told everyone
that she could not have a boy walking around in a skirt and heels
with customers coming and going.

I was then made to stay in the filing room all day so that
customer could not see me. At the end of the day they all asked if
the skirt had helped with keeping my stride correct, I had to agree
that it had. Marie then said that they had all been thinking and had
come up with a solution. I was told to get there early again
tomorrow.

When I arrived the same people were there and I was told to
change as I did yesterday, after I had changed they told me to
remove my shirt and tie. They then gave me a Bra and fitted it on
me. They padded the cups and gave me a blouse to wear, after I had
put the blouse on the produced a wig and fitted onto my head. They
then put some lipstick on my lips. They then took me to the toilets
were there was a long mirror to show me how I looked, I did look
like a woman.

They then said to the boss that there were now all women
working in the office and showed me to her. She said that it looked
better than a man with a skirt did and as long as I did not talk or
approach the customers it should be all right. She had been told why
I was wearing the heels and she wished me good luck. She also said
that they should find a woman's name for me as they could not keep
calling me Fred the way that I now looked. They all went away and
then they told me that they had now renamed me as Ann.

I was then stuck in a blouse and skirt for the rest of the day. At
the end of the day they asked me how it had been being Ann for a
day, I told them that in the end it did not seem too bad as no body
had taken the Mickey out of me. As it was Friday they said it was a
pity that I had started too late to come to this Fridays Night Party but
they had booked a place for me next time. They gave me back my
clothes and said that they would see me bright and early next
Monday with some more clothes.

During the next week I had worn dresses, blouses and skirts and
they had also got me to wear ladies knickers underneath. They had
also started to bring in jewellery for me to wear, I told them that the
clip on earrings hurt my ears but they said that you need to ignore
the pain to look good. At the end of the week they all commented
that I had done better with the 2inch heels than they could have
imagined and starting next week I would be trying the 4inch heels.

The boss commented to me that I had made a better woman than
she could have imagined and I could do all of the office jobs now
even being seen by the customers. The next week when I arrived
they had brought the 4inch heels and the 2inch ones so that I could
change during the day if I found the higher ones difficult.

They had also started to put more makeup on me and taught me
how to do it my self. At the end of the day on Tuesday I went to get
my normal clothes but they said that I should go home as a woman
and that they would give me some makeup so that I could come to
work without changing.

When I got back to the boss's house that night I found that some
of them had been there during the lunch break and my wardrobe did
not have any masculine clothes at all. A note was left saying that
they thought that I still needed some more practice so I should be a
woman all the time and they would return my clothes after the party.
I was therefore now stuck being a woman for another 6 weeks.

During the next week I had to take the mail to the post office and
the cheques to the bank with Marie. I was starting to get more
confident until the fateful day when Marie was out and I had to go
on my own. After that I became more confident, then one lunch time
Marie said that I should get my hair done so that I did not have to
wear the wig all of the time and she had booked me an appointment
for that evening straight after work.

I did not want to go but two of them walked me to the salon and
told the stylist what she should do. When I left my hair had been
dyed a light brown and extensions had been added so that my hair
was now shoulder length. They had also pierced my ears and I now
had studs in both ears. They then took me to the nearby nail bar
where I had extensions added to my nails and painted a bright pink.

I then carried on until the day before the party when they took
me out at lunch time to buy a pretty party dress with matching shoes.
As I now had pierced ears I could wear a nice earrings and necklace
set.

On the night of the party Marie came round to help me with my
makeup and to get ready. During the party after much wine and
spirits had been drunk they all commented that the enjoyed it now
that the office was all women again and said that they did not think
that I could pull it off for another 2 months until the next party.

With the amount of spirits I had drunk I said that I could if they
would pay for half of the next meal for me. They said if I did then
they would pay for my meal again.

One thing lead to another and it has been 3 years since I joined
the office, three years of being Ann. I now have breasts of my own,
as little did I know that all of the women went on the pill but I
consumed them and not them. They are now talking about me
having the operation to get rid of my male parts and become Ann
completely. The change would not be to much as I now have a bank
account in the name of Ann and my own flat.