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The Nanny
Alyssa Davis
The ad said: child care person wanted, full-time, live-in position,
private quarters, use of car, light housekeeping, salary commensurate with
experience. This sounded like an ideal position. I would have a place to
live, a place to continue work on my book, and the easy duty of taking care
of a small child. The benefits sounded good...this is certainly worth
investigating.
"Hello Mrs. Duncan...my name is Terry Parson. I'm calling in response
to your ad for a child care person," I said trying to sound interested
though apprehensive about applying for a traditionally female position. I
wondered what her reaction would be.
"Hello uh Terry...yes, well...the position is open if you'd like to
come and interview. I'm available this afternoon at 2PM," she replied.
She wasn't expecting a male to call but she was obligated, by law, to
consider me. I confirmed the time, got her address and made the
appointment.
"Hi Mrs. Duncan...I'm Terry Parson. I'm here about your ad for the
child care position."
"Oh yes...come in please," she offered, "and my name is Pam. We want
to keep this very informal."
She was an attractive woman, tall and slender, about my age, very well
dressed for a housewife, in my opinion--casual but expensive casual. Her
hair was well coifed, her makeup, perfect. I felt an immediate attraction
to her. I was escorted into the family room of this beautiful home. It
was well furnished, comfortable, a brick fireplace in the corner, and a
wall of windows overlooking a wonderful view of a tree-filled well-groomed
backyard. We sat down and began our discussion of the advertised position
as Pam poured two cups of coffee which had been previously prepared and
sitting on the appropriate coffee table. It was difficult to concentrate
on the purpose of this visit, but I was to learn that she wasn't a typical
housewife.
"I have to admit, Terry, that I was surprised to hear a man inquiring
about this position. I expected only women would apply. So, have you had
much experience caring for children?"
"Ah...Well not exactly, Pam...not as a nanny, but I come from a large
family where I was the middle child and had to share in the care my
siblings while my mother worked to support us. But I'm confident I can
care for your child as well as a woman and perform other duties equal to,
or maybe even better than most women, especially when it comes to
housekeeping. I've done more than my share of that too."
"Hmm, interesting point. However that remains to be seen. Really,
why do you want this job?"
"To be perfectly honest, Pam, I'm an aspiring writer, and I'm working
on a book. I figure I can work on it in my spare time, while this job
would give me a place to live and especially a quiet place to write, and a
little income to top it off. I think the domestic environment would be an
excellent opportunity for me, and I know I would be a capable and
responsible person to care for your child."
"An interesting attitude...I thank you for your candor, Terry. There
are several points of view here. On the plus side, my child is a male, and
it wouldn't hurt to have a child care provider who is also male since he
doesn't have a father...I'm divorced and a single parent. So you would be
a good influence on him. But, on the other hand, you don't have any
experience as a Nanny, therefore you don't have child care credentials or
references for me to check. Also, it is a live-in position and I think it
may be a little awkward for me to have a man living here. However, let me
consider the situation and get back to you. Please fill out this
information form and let me review it. Thank you for stopping by."
When I completed the prepared form, Pam escorted me to the door, we
shook hands, and I departed. It was a short interview so I had no feelings
one way or the other about it's success, so all I could do was wait, but
now I was anxious to move in with this beautiful lady. Work progressed
slowly on my book, and I was running out of funds so I would need to find
some form of employment very soon. After a week had passed, Pam called and
invited me for another meeting.
"Hi Terry....I called you to return here for another discussion about
the Nanny position and have you meet my son Jerry."
We went to his playroom and I sat with him for a little while to let
him warm up to me which he did immediately. Pam observed our interaction
and was impressed. After some story telling and a little playful romping,
we distracted him and quietly departed.
"I'll be up front with you as you were with me. I haven't had a great
deal of success with applicants. The few that applied were not eligible
for various reasons I won't go into. And, I don't have a lot of time to
pursue this selection...I have a busy schedule and a career to manage.
I've checked your past employers and the references you gave me. In spite
of the lack of formal child care experience as a Nanny, you are the best
candidate so far, and Jerry seems to like you. Let me lay the position out
for you in detail to see if you're still interested."
She was all business, yet I found her demeanor intriguing and still
physically attractive.
"The job involves taking care of my son full time, he's a year and a
half old, and can be a bundle to handle, as well as managing the
household...some cooking, and outside work as necessary. I have a
part-time housekeeper for cleaning. You can hire people to help with the
outside services if you wish. So, in general, you'll be expected to
completely manage the house as well as provide child care. You'll get your
room and board of course, free use of my cars, re- reimbursement for any
household or child care expenses...just about complete autonomy, since my
business requires a lot of travel and long hours away from the house, so I
have to trust you. You'll get a salary of $250 per week plus medical
insurance. Oh, and we will take occasional family vacation trips, at my
expense, with you in charge of Jerry, my son. Does it sound OK so far?"
"Yes it does, Pam...it's a very generous offer." Too good, I
thought...too good to be true, which meant there had to be a hitch.
"Now as I told you, I'm a single parent so it would be just the three
of us here, and there- in lies a bit of a problem. I had expected to hire
a female Nanny. I run the business out of my home and frequently have
clients visiting. I obviously can't afford to tarnish my reputation by
having an unmarried man living here with me so for the sake of appearances,
if you accept the position, you will be required to wear a Nanny's uniform
and appear as a woman at all times. No one must ever know you're not an
actual female. Looking at you, I think that wouldn't be too much of a
problem...you have very fine features, almost effeminate.... another
reason I even considered you. If it was ever discovered that you're a
male, it would mean a lot of embarrassment for me resulting in instant
termination for you. I realize this is a strange request but it's the best
I have to offer. What do you think...are you still interested?"
Everything was sounding great until she laid that last part on me.
That was the hitch. Dress and pass as a woman in a full time position?
First the job sounded too good to be true-- good salary and benefits-- then
comes another side I hadn't exactly planned on. This was not a game...she
was serious. But it was an ideal job offer otherwise. So what did I have
to lose besides my identity, my gender, my.....?
"Gee--I don't know about passing as a woman, Pam. I...I've never even
dressed as a woman."
(Well, almost never, I thought...a half truth, but it was along time
ago.)
"I expected that...I'll help you with the transformation if you're
willing. I'm pretty sure we can do it, with your cooperation. It's very
important to me that you pass completely because you'll be in contact with
other Nannies in the neighborhood as well as my clients, service people,
and merchants, so you'll have to convince everybody that you are a real
lady. On the other hand, you will have time to work on your writing as
well as enjoy the benefits of this position," she offered as an incentive
to sell me on the idea. "You might actually enjoy living as a woman," she
added, smiling.
I had to make a decision so in an impetuous action I responded,
"Well, Okay, I guess...I'll give it a try. The position sounds
wonderful, but I don't know about this female impersonation thing." I had
to refrain from biting my tongue as I had a memory flashback. I hoped my
nose wasn't growing longer.
"Very well-- it wont be so bad... I'm confident we can pull it off,"
she repeated. "I'll advance you your first month's pay to buy you a
woman's basic wardrobe, but I'll provide the uniforms I want you to wear.
In this neighbor, the Nannies wear uniforms. Yours will be a black
polyester dress with a white collar, black hose, and black flat heeled
shoes. One other thing, Terry. You must sign an employment contract with
me as protection for both of us. I had one drawn up in case you accepted.
It states that you will be employed by me only as long as your identity as
a woman is maintained and kept secret to only you and I, as I mentioned.
Also, you must remain in my employ until my son reaches the age of six and
can start school full time. In the event of any violation, your employment
shall be immediately terminated and you shall pay the balance of any salary
you will have earned up to the end of this contract. On the other hand,
you are guaranteed a job for the next four and a half years."
Now I was to be indentured to live as a woman for the next four and a
half years! Again, it was good job security for what I considered to be
ideal conditions for a writer, but under very unusual terms. With mixed
emotions, I signed the contract.
With my only possessions packed into two suitcases, I moved into my
new surroundings the next day and the transformation began immediately.
After taking measurements of my body as a dressmaker would, Pam, little
Jerry, and I went shopping for my new wardrobe. Pam selected some basic
items of assorted underclothing, narrating as we went along although I was
too busy with Jerry to pay her much attention. Assorted underpants in both
cotton and nylon so I could decide which I prefer, bras with padded cups,
slips, both half and full, hosiery in different colors but mostly black,
pantyhose, gartered, and thigh-highs. A wide variety intended to exposed me
to feminine attire so I might choose my favorites later. It felt as though
she was buying these things for someone else so I went along with her
selections rather disinterested. We went into the ladies dresses area
where she picked out several styles of dresses, skirts and tops, jeans, and
shorts, occasionally asking my opinion of things. I just agreed with
everything she said. I had no idea what she was muttering about. I was
attending to Jerry and keeping him content. He required all my attention.
Our next stop was the shoe department where she purchased some women's
canvas shoes for casual wear as well as some medium heeled dress pumps and
my uniform shoes. She commented that we both wore the same size in many
items...which might prove convenient. We finally ended up at the cosmetic
counter. Pam picked an assortment of cosmetics and makeup items for me. I
had no idea what she bought, but she knew and that was all that mattered.
Leaving the mall, we made one more stop at a wig salon. Pam told the sales
associate that I needed a wig for a woman's part in a play I was to be in.
I was fitted for a suitable wig in my own hair color. She chose a style
that would be easy to maintain; a page-boy cut, short, with bangs. The wig
enhanced the feminine features in my face....Pam was right. Back at the
house, we unpacked our purchases and found places for everything in the
closets and drawers in my room, a spare bedroom Pam had furnished as a
Nanny's quarters. Expecting a female Nanny, the room was decorated
effeminately. All in pink and white colors, ample lace and chiffon...lace
trimmed bedcovers and skirts on the bed and furniture, chiffon curtains and
lampshades. Pink flowered wallpaper with little red roses...I thought,
'how appropriate for my new lifestyle'. Even my bathroom had pink fixtures
and gold trim. All rather nice. It gave me a sense of deja vu.
Prior to my gender swap, Pam advised me to bathe, shave my body hair
and change into my new clothes. I was to call her if I needed help with
anything but I didn't think that would be necessary since I had been raised
with sisters. I took a long hot soaking bath, during which time I shaved
my legs, arms, underarms, and chest clear of what little hair I had. I
also shaved my face taking pains to get a very close shave. I knew she'd
want me to do that in preparation for some makeup. When I was done, I
gently dried myself off and applied body powder to my now baby soft skin.
It felt kind of strange being so hairless again, but that was only the
beginning. I stepped into a pair of nylon panties and pulled them up. The
cool, smooth fabric felt good against my skin. I next selected a pair of
nude colored pantyhose and, sitting down, placed a foot into one leg,
gathered up the material and rolled it up my leg half way. Then, I
repeated the same maneuver for the other leg, at which point I wiggled the
remaining part of the hose up to my waist. I didn't remember pantyhose
feeling so good, and they made my legs so shapely. I took a padded bra
from the drawer and, placing my arms into the straps, gathered it around me
and hooked the closure. Pam had the foresight to buy me front closure
bras. Even though the cups were padded, there was still a need for more so
I filled them with the breast enhancers she provided. Now I had a more
feminine form and I can't say I didn't like it. I eagerly stepped into a
half slip and pulled it up to my waist, followed by a skirt and a rayon
blouse. The uniform dress would come later. I had no problem with the
buttons on the blouse although they were backwards for me. The way the
blouse conformed to my breasts excited me to a bulge under my skirt urging
me to rub my sensitive manhood but I didn't want to start something I
couldn't finish. Fortunately the skirt was full enough to cover it. I
next stepped into a pair of pumps with 2" heels, and placing the wig on my
head, I checked myself in the mirror before presenting myself to Pam. I
was satisfied with my appearance...at least I was presentable. I not only
looked good, but I felt good. I loved the sensation of these garments. I
thought I'd be shy dressed this way in front of Pam...but, strangely, I
wasn't. Having to wear these things all the time isn't going to be bad, I
thought. With a few practice steps around my room, I walked out to show
Pam.
"Wow Terry...you do make an attractive woman. I knew you could do it.
How does it feel to be wearing a skirt and all the other things?"
"Surprisingly comfortable, Pam. I think I can learn to like this," I
replied convincingly.
"Well, I'm glad you feel that way...you're going to be wearing those
things for a long time," she said, smiling. "Let's get some makeup on you
to complete the look."
We went into the master bathroom which was a large room with a
separate tub and shower stall and a large vanity with a lot of lights. Pam
sat me down in front of the mirrored wall where she had an assortment of
cosmetics arranged. She complimented me on my fresh shave as she began to
apply a foundation creme with a small sponge. As she applied each item,
she described what she was doing and why. She worked on one side of my
face and let me do the same to the other side so I'd learn how. I tried to
be amazed at the metamorphosis that was occurring. When she had finished,
I was looking at a beautiful woman! I felt delightfully feminine.
"You're a natural, Terry. You're very pretty as a woman! You'll have
no problem passing and I think you'll enjoy it. We don't even have to
change your name. So, how do you like your new look?"
"What can I say, Pam, it's not bad...not bad at all," I said as I
viewed myself from all angles. I found myself speaking very softly. Pam
sensed the change in my tone of voice.
"Let's begin work on teaching you the basics," Pam said as we went
into the family room. She proceeded to instruct me in how to sit properly,
walk graciously, how to gesture like a lady, how a lady speaks...voice
control, eye movements, facial expressions, and feminine vocabulary. I
didn't remember there was so much difference between genders. Like all
men, over time, I had taken women's actions for granted. But now I had a
vested interest to learn, actually contractual. I made a conscious effort
to practice everything Pam taught me since I looked and felt so feminine.
Wearing a skirt was very different than pants. It patterned my behavior.
I had to keep my legs together while sitting out of sheer modesty, and it
governed the way I walked...the way it swirled around my legs. I enjoyed
it. We practiced until late that first evening. At bedtime, Pam reminded
herself that she had forgotten to buy me nightclothes so she loaned me a
nightgown to sleep in. It was pink nylon with lace trim and a perfect fit
as she knew it would be. I removed my makeup and hit the pillow. That
night, I slept like a baby in this free-flowing, soft, and comfortable
garment. This new lifestyle was going to be all right, I thought. For the
next two weeks, each morning, I eagerly got dressed, applied my own makeup,
and while taking care of Jerry, continuously practiced Pam's instructions
of how to properly walk, sit, gesture. She constantly reminded me if I
slipped up on anything until it became instinctive. When the specially
ordered uniforms arrived, I willingly wore the new dresses. By that time I
was accustomed to maneuvering in a skirt and I found them to be quite
comfortable. Worn with my padded bra and black hose, they were indeed very
stylish and feminine. Pam had good taste.
Pam stayed with me during that indoctrination period so we got better
acquainted with each other and she established a higher level of confidence
with me. We related to each other as two women as I worked to forget my
recent past and concentrate on the present. Very little progress was made
on my book while I focused on my transformation. I found myself really
getting into learning to be a woman...wanting to be a woman--again. Pam
had become very persuasive about my transition--it was total immersion.
She was a good salesperson.
Finally, Pam had to go to visit a client for a meeting and I was to be
alone with Jerry for the first time. That didn't bother me, but, I
thought, what if someone came to the door. Was I ready? Was I passable?
That concerned me because I didn't want to jeopardize my position. Pam
reassured me that there would be no problem. She felt I was completely
passable as a woman. As it turned out, there were no visitors that day, but
all afternoon, while Jerry napped, I practiced my acting as a lady
pretending I had guests. I knew I should have used the time for writing
but I was too preoccupied with my appearance to concentrate on anything
else. But it was paying off...my confidence level of being a new gender
was rising. One afternoon, I was preparing lunch when the doorbell rang.
It was a salesman for a lawn service. He was very courteous and not the
least bit suspicious, but then why should he have been. My first contact
with another person as a woman and I passed. I was pleased and relieved.
I told Pam what happened and she suggested we go out in public, perhaps to
dinner. I changed into something appropriate, freshened my makeup,
prepared Jerry for the excursion, and we went to a restaurant. Things went
very well, I tried hard to be a lady, which was now easy, and didn't get a
second glance from anybody, including the waitress. Pam was very pleased.
I knew it was important for me to pass...in my mind, the contract was
hanging over my head. As luck would have it, Sarah, the Nanny of Pam's
neighbor spotted us and came over to say hello. Pam introduced me and
invited her to visit us at the house. Sarah was pleased to meet me and
promised to do so. This was to be my real test...to be accepted by a
genuine, unsuspecting, woman. After dinner, we returned home to put Jerry
to bed and review my evening. I got a glowing report from Pam. She said I
was doing a great job with my transformation, better than she had expected,
and she was pleased with my Nanny performance. She had absolutely no
remorse about hiring me for the job. We were becoming good friends, but it
was a woman to woman friendship. She treated me as a sister as we
discussed feminine things such as makeup, styles of clothing,
children...girl-talk. I never burdened her about household things. I just
took care of them on my own.
Within a week, Sarah came to visit with Jamie, her charge. We spent
the afternoon talking and getting acquainted while the children played.
She gave no indication that I was anything but another female...it was all
girl-talk with her also. At first, I was a little nervous, but I soon
relaxed and enjoyed her company. For someone who had not worn women's
clothes for a long time, I was now able to be in the company of another
woman, as a woman, and feel like a real woman. It seemed so natural. For
a few fleeting moments, my thoughts turned to wondering what she'd do if
she knew what was under my dress, but those thoughts quickly disappeared as
I mentally accepted that I was a lady. We became good friends, and through
her, I met the other Nannies in the neighborhood. I was totally accepted
by all of them, and in their company I honed my skills of presenting myself
as a genetic woman. We met frequently for coffee and gossip which provide
me with the opportunity to learn the art of communicating as a lady. I
continued to make a conscious effort to learn. Sarah accompanied me to get
my driver's license in my new gender . I told her I was new to the state
and needed it. She never doubted otherwise....nor did the officials at the
license bureau.
Within a few months, my hair was long enough to rid myself of the wig
and maintain the same pageboy style. With Pam's assistance, I had groomed
my eyebrows to a feminine shape. She asked me if I'd consider permanent
removal of my beard and other masculine body hair, at her expense. I
readily agreed to it so she arranged laser treatments for me. In one
month, my beard was completely gone, my eyebrows were permanently arched,
and they were working on my chest and legs. In time for a summer vacation.
I was completely acclimated to the job of managing the household and
caring for Jerry as well as to my new identity. My effeminate actions were
instinctive now...I think I had completely forgotten how to be a man
anymore and I didn't care. Pam was right...I was quite comfortable living
as a woman. So when Pam invited me to accompany her and Jerry on a trip to
Cape Cod for two weeks, I eagerly accepted. Of course my Nanny duties
continued, but it was still a vacation since Jerry was so little trouble.
He was like my own son and I was like his mother. And I was to travel in
regular street clothes.
We stayed in a hotel in Provincetown, spending time shopping, browsing
the antique stores and walking on the beaches. During Jerry's nap time, I
continued work on my book. Pam cared for Jerry for a few nights while she
let me attend some female impersonator shows which were prevalent. The
boys were quite accomplished in their presentations as women, singing,
dancing, and generally enjoying themselves in their pseudo gender.. I
could appreciate what they had to do to look like that, but I had no
regrets about the effort I had to go through. I had the advantage of not
having to switch genders every day. Even the transvestites recognized me
as a genetic woman...I had fooled everyone. When I told Pam, she was
delighted...and so was I. She said I had passed a test by masters of the
craft of transgender.
I mustered enough confidence to purchase a swimsuit and wear it while
walking on the beach. It was a rather a conservative design with a little
skirt, but was still somewhat revealing...a big step for me. I had to fill
the bust cups with foam forms but it looked very authentic. Pam said I
looked perfectly lovely and I had to believe her. I did get a few admiring
looks from men along the way, and that pleased me. I would have been
disappointed if they hadn't looked. During this trip, Pam and I had a
chance to talk about our pasts. I learned that she had been the victim of
a bad marriage and a bitter divorce. She was really down on men now. She
vowed never to have anything to do with them again. She had been burned
once and that was enough. When I asked how she felt about me, she replied
that she didn't see me as a man anymore and felt very comfortable with me
in my new persona. She accepted me as a woman. She proved it by changing
clothes in front of me in the hotel without any display of modesty. My
femininity came forth when I could view this beautiful lady in her undies
and not get aroused...after all, I was now wearing the same clothing as she
was. I lusted for her but not as a man for a woman but as a lesbian.
I finally disclosed to Pam the secrets about my past. I was the only
boy in a family of eight kids. Being a middle child and my mother being
the sole support as a widow, we had limited income so I was forced to share
my sibling's clothes as much as possible. For the most part, I was raised
as a girl since I spent most of my early childhood in girl's clothes, going
to parties, church, social events in dresses and to school in mostly
androgynous attire...my limited boy's things on the outside, girl's
underneath. I grew to accept being a girl since I knew no other way of
life and had only girl playmates until I was too old to conceal my
maleness. I even dated a few boys with my older sister's help. They had
made me very effeminate. The transition to manhood was difficult. I took
to writing because I had limited skills in other areas. This domestic
position was a natural for me so I applied and fortunately got the job.
The requirement to live as a woman was a bonus I hadn't expected. I admit,
I love living as a woman again.
"I noticed you took to the transformation easily and you were a very
fast learner," Pam admitted.
"I'm happy you've found yourself...I'll do whatever I can to help you,
Terry."
My admission drew our friendship even closer. The second week of our
stay in P-town, Pam canceled my hotel room and had me share her room and
her bed. It just seemed so right. We slept as sisters...no...lesbian
lovers. We kissed, embraced, and made love with no penetration other than
orally. It was fulfilling to both of us...it was beautiful. Our vacation
ended too soon but our relationship didn't.
Our bond became intense. At home, Pam was the husband and head of the
household, while I assumed the role of the wife, and of course Nanny to
Jerry. I moved in with Pam, shared her bed, and satisfied her any way a
wife should. It wasn't a business relationship anymore...it was a marriage
and I was the bride...I loved it...I loved Pam. She shared her entire
wardrobe with me, dressing me in many of her fancy dresses which I modeled
for her. I was completely comfortable while attending her parties wearing
a short cocktail dress with high heels and dark hosiery as a maid to serve
her guests. It was at one such party that a gentleman client approached me
and asked me out for a date. Pam urged me to accept...it would be
favorable for her business...so I did. I had been living as a woman long
enough so I wasn't worried about being discovered...in fact, I was very
relaxed with the prospect of dating a mature man. He made me feel very
feminine, extending all the courtesies a gentleman does for his lady. I
loved the attention. The evening ended with a warm kiss, my first adult
kiss by a man, and I enjoyed it! That was the prelude to another date and
more kisses and some petting. I liked the experience of being held and
kissed by a man...but knowing it could go nowhere, I ended it before we got
emotionally involved. But I did continue to casually date other men. I
loved being the object of men's affections, being pursued, romanced,
seduced. It was wonderful. I learned to pleasure a man in a very womanly
fashion, after all, only a male knows what pleasures a man the most, and I
got very good at it. And I could conceal my maleness well enough to allow
them some liberties. I was very careful about that.
After my first dating encounter, I asked Pam if there was anything I
could do about enlarging my breasts. I was becoming self-conscious about
wearing breast forms, especially when a man was holding me. Even the good
silicone forms were not enough. She suggested breast implants. We talked
to her doctor friend who agreed that was the best way. Hormones were slow
and critical. So the procedure was scheduled and I received a set of
breast implants which allowed me to amply fill my bra's C cup with my
natural breasts. They looked wonderful and I was proud of my new figure.
Especially since there was so little discomfort with the surgery. Now I
had genuine cleavage...not just an illusion! Pam was as happy as I was and
couldn't leave her hands off of them as much as I loved her touch. I could
now wear her dresses with the lowest necklines...a whole new part of her
wardrobe. I loved my new body. I did start a regimen of hormones.
Jerry was getting big now, almost 4 years old. One day, I noticed him
playing in our room. He was walking in my high heels, with a nylon
stocking around his neck as a scarf, and had lipstick on his face. He said
he was playing mommy. I asked him if he wanted to look like a little
girl...like Nanny, to which he replied, yes. I cleaned his face of the
smudged lipstick, removed his boy clothes, and fashioned a dress from a
blouse, using a stocking as a waistband. I carefully applied fresh
lipstick, blush, and eye shadow, making him into a darling little girl
completed with a ribbon in his long curly hair. He happily stayed that way
until Pam came home. When she saw him, she laughed and hugged him.
"I didn't know I had a little girl. You're beautiful, Jerry. Do you
like those clothes?"
"Yes Mommy. Nanny dressed me. Now I can be like you and Nanny."
I apologized to Pam for doing that but she smiled and said it was
clever. It made me happy wearing those clothes...maybe Jerry would be
happy, too. She was in no hurry for Jerry to change. She let him play it
out, but he stayed that way till bedtime. I told Pam it was Jerry's idea
to cross-dress. He had played with my things before, but this time he
dressed himself so I helped a little. We wondered if he wanted to do more
of it. The next morning, he asked me if he could do it again, but I told
him my clothes don't really fit very well and that we'd buy him his own
things. He accepted that. Later, I again found him wearing my lipstick
and shoes. I called Pam to tell her what happened. When she came home
that day, she had bought Jerry some things. She figured he would just
secretly wear our clothes anyway so let him get it out of his system now.
She bought him little girl's panties, petticoats, a dress, hose, and shoes
which he immediately put on and came out to proudly model for us. With his
long curly hair, he did indeed look like a little girl. He continued to
dress that way for the next few days and played as a girl until I was able
to discourage him by making him do girl's chores.
I talked with the other Nannies, during our routine coffee sessions,
about Jerry's behavior towards cross-dressing. Some of the others had
heard of it, but none had first hand experience. They thought maybe
because there were no male figures in the household. But then some had
girls who never wore dresses and played with boy's toys and games and never
thought anything unusual of it. So why were we so disturbed about Jerry?
He'll likely outgrow it as the girls will. Somehow, I wasn't so sure....I
never did.
Pam wasn't helping...she continued to buy Jerry girl's clothes. She
thought it was fun, the things being so cute. Jerry loved them...I'm not
sure whether because they were just new items or because they were pretty,
and he continued to wear them and slowly began to act very effeminate while
Pam encouraged it.. My threats of doing girl's work no longer worked...he
jumped right into the tasks at the mention of it. I think Pam was allowing
this to happen as her way of getting back at men. She had made me into a
woman, now she was doing the same to her son, and I was helping her.
For Jerry's fifth birthday party, we invited the neighbor's female
children and their Nannies, of course. Jerry was now wearing girl's things
routinely and behaving accordingly. Since all of the other children were
girls, he fit right in with them and they played together so well. He was
receiving no male role model support...certainly not from me. Trying as
hard as I could, well, not too hard, I couldn't prevent Jerry from wanting
to be a girl so I gave up completely. Pam and I discussed taking him for
counseling as a last resort to ease my conscience, but she wanted to wait
until it was closer to him starting school....another year. At that time,
my contract would be up and I could leave, although I don't know where I'd
go. I was happy here, I loved Pam, and I loved being a woman...I knew I
couldn't be a man anymore nor did I want to be one. We continued to let
Jerry behave as a girl or a boy, whichever he chose, not unlike the genetic
girls. He played only with the other girls and they treated him as one
especially when he dressed the part. Pam let him...encouraged him to wear
makeup and play dressup, complete with jewelry, nylons, pretty dresses.
she bought him everything including feminine toys and games. She was
completely feminizing her little boy, I think to get back at Jerry's
father. Whenever I'd remind Jerry that he was a little boy, he'd cry, deny
it, and if I pushed it, he'd say he wished he was a girl...he didn't want
to be a boy. I knew we were in trouble.
I finally convinced Pam to take Jerry to a counselor who decided,
after extensive testing, that Jerry was indeed confused about his gender.
Of course I didn't mention about Pam's encouragement for him to be a girl.
He had developed all the characteristics and attitudes of a female, and to
regress back would be very difficult and harmful to his interpersonal
relations with other children of both genders. Pam talked to her Doctor
friend about Jerry, seeking medical advice...perhaps a sex reassignment to
make the body fit the mind. The Doctor said that because Jerry was so
young, nothing radical should be done now except to continue raising him as
a girl. When he approaches puberty, they could block his male physical
development and cause him to develop as a female. Later, surgery would
finish the re-assignment. So, Pam agreed to that and made plans for Jerry
to attend private school as a female.
In the Fall of Jerry's 5th year, Jerry was enrolled and started a
private school as a little girl. His name was changed to Jeri. My
contract with Pam as Jeri's Nanny was finished and I was free to leave.
Pam extended the offer for me to stay with her as her female assistant in
her business with the same terms as before, which I readily accepted. I
would have married her but she would have no part of that so we stayed
together as lesbian lovers. I was a total woman and would never change
back to life as a man.
Jeri developed into a young lady and, upon reaching puberty, was
started on hormones to allow her body to become that of a woman. She
became a beautiful teenage girl. After high school, she had sex
reassignment surgery to become a legal female. She never learned my true
gender, but always considered me a woman....her Nanny.
I never did complete work on my book.