Mom and I moved to the edge of a large city so she'd be
able to find work. She did, but the pay still wasn't enough.
She decided I would have to find something also. The trouble
was, there were more boy's in our area than girls, and jobs
for boy's weren't to be found. When shopping one morning Mom
noticed the store's notice board was full of babysitting
jobs. She wrote several down and called them. It was a dead
end, all said they didn't really want a boy baby-sitter.
The next day when Mom was telling Mrs. Dorn, (our next door widow
neighbor), about it, Mrs. Dorn looked at me, smiled and
whispered something into Mom's ear. Mom looked at me, shook
her head, and said she just didn't know. Mrs. Dorn then said,
" He look's to be about the right size. I have several
closet's full, I've kept practically everything I had for my
child, and I would just love to help." Mom didn't seemed
convinced, so Mrs. Dorn continued, "Sometime's we do what we
have to." Mom shrugged her shoulders, and told me to come on.
We went into Mrs.Dorn's home. She led us into an upstairs
bedroom that was once her daughter's. It was a pretty pink,
very femininely decorated room with an interesting roof.
It had a large closets chocked full of girl's dresses, skirts
, blouses and shoes, etc. With a dresser full of lingerie
between two windows on the end. I loved the feather bed,
so incredible soft.
The bathroom was also in pink with lots of mirrors all around.
It was all a beautiful white tile and the vanity was built in.
While thinking about all this I decided I loved it..and I also
thought..I am not a girl even..well..not yet! and giggled at
myself. Giggled? good Grief..whats happening to me?
I looked at a glass animal collection while mom and
Mrs. Dorn looked in a closet. They brought out several
dresses and shoes and laid them on the bed. Then they went to
one of the dresser's and pulled out some girl's underclothes.
I was looking at a shelf full of dolls, when mom softly
called my name. Mrs. Dorn had left the room, and mom told me
to strip. I protested, when I saw the bra and panties in her
hand, but she told me again in a firmer tone, so I did. I put
on the panties, and she fastened the bra on me and adjusted
the straps. To my own amazement, I found I it not so bad
wearing girl's clothes. Mrs. Dorn came back in and slipped
some padding into the cups of the bra. Then a slip, followed
by several of the dresses to determine what my size was, and
what looked best. They decided that everything looked nice
on me, and that indeed, this was going to be easier than they
thought. My hair is long enough that a little styling,
curling, and a clip on fall gave me a very feminine look. Mom
put a touch of blush and some lipstick on me. They gave me
some ruffled socks at first, but decided they made me look
too young. So a pair of shiny pantyhose I wiggled into, and
then strapped on some 1 inch pumps. They decided to make some
outings to familiarize me and coach me in feminine ways and
manners.
We went to a mall to get my ears pierced, since clip
on ones hurt, and many boys wore the studs nowadays anyway.
They were watching me constantly, both noticing things and
instructing me to; walk this way, hold your hands like this,
keep your legs together, don't sit like that, pull your bangs
back like this, never stand like that, do this, do that, I
thought I was going to go nut's. We window shopped for
awhile, went to a restaurant and ate, then back to Mrs.
Dorn's. Mrs. Dorn and mom had me put on some large heavy
earrings and try on several more dresses. They did the old,
book on the head trick, to help me with posture and poise.
The next morning mom called her brother's wife and asked if
we could practice babysitting the baby for a couple of days.
Mom taught me about baby's, how to feed, change, and
entertain them. I wore my girl clothes the whole time so I
would get used to them, as moom said. When she went to work,
little Cindy and I went next door to continue my education.
Mrs. Dorn was constantly telling me something about
babysitting, not just for baby's, but also toddlers, and
older children. We went over what would be needed to take
care of them, and keep them real happy, so the parents would
call me again. So, she learned me how to be a good baby-
sitter, and instructed me in the art of being a very feminine
girl at the same time.
Mom and I assembled a kit to take with me. A flashlight,
first aid kit, some toys and games, emergency phone numbers,
and a couple pieces of bribery candy. I decided it was easier
to change a skirt, or blouse than a dress, and I would take a
spare of each. All of this went into a large shoulder bag.
Mom got me one of her purses, and put a hairbrush, some make
up, a coin purse some money, and a little package of
Kleenex's in it. Mrs. Dorn handed me a little mace canister
and instructed me on how to use it. She said there are some
bad people out there that a pretty girl might need to protect
herself from. Mrs. Dorn and mom talked, and they decided it
would be easiest to have me come over to Mrs Dorn's House,
whenever I needed to become feminine. That I was to consider
her daughter's room as my own. She gave me a key that fit
both the side and front door to her house. There was shrubs
and a fence that hid the space between our houses, and so
also my entry. She said I could come anytime, that she would
tell everyone that I was a daughter of her sister and that
she was boarding me for awhile. This way I could come and go
from her house as a girl, and from my house as a boy, and
none of the neighbors would hopefully not know the
difference. She said to call her anytime, for anything I
needed. It didn't matter if it was for a ride, money, advice,
or just wanted to girltalk. She wanted me to feel free to
call her, and to please treat her as family. I nodded a yes
and smiled. Her daughter's name was Wendy, and she asked if I
would go by that name. I said sure, and that made her real
happy, and she hugged me. She then asked me to call her Aunt
Patty instead of Mrs. Dorn. That will be easy, I smiled, and
she gave me another tight hug.
Friday morning, mom called one of the numbers and got me a
job on the first call. She made more calls and had a job for
every night of the week. She was smiling broadly when she
told me, I'd be making $6 an hour, almost what she made. She
looked like a tremendous load had been lifted off her
shoulders, and I made a mental note that I must succeed for
her, no matter how bad things seemed. I tried to look for a
bright side .. The clothes were comfortable, and I wouldn't
be getting hot and sweaty, like when I mowed lawns last
summer.
The night of my first job came. I crossed to Mrs. Dorn's ..
er .. Aunt Patty's house. She wasn't home so I went back to
MY Room. It was strange walking into this pretty ruffled and
lace room. I was a bit scared as I stripped, and showered. I
walked to the closet and picked a nice blouse and skirt,
shiny pantyhose, and high 3 inch heels. I fixed my hair and
make up and doubled checked my sitter bag. Mom came over to
see how I was doing, and asked why I was wearing high heels.
I told her I wanted to make a good first impression, that
they helped make me feel feminine, and besides I had my
tennies in my bag. It was funny, this feeling I had, like I
really might feel if I were a girl. Mom drove me over, even
though it was only two blocks. She helped me with my purse
and bag, hugged and kissed me, and wished me good luck. I
thought about my heels clicking on the concrete, and the way
my pantyhose felt on my smooth legs inside that silky slip. I
flipped my hair and looked over my shoulder at mom. She was
smiling as she watched me walk up the sidewalk. I rang the
door bell, and turned and waved at mom. She blew me a kiss,
and drove off.
Mrs. Laten was fastening an earring when she opened the
door. She smiled, I introduced myself as Wendy, and she
ushered me in. She gave me a quick tour of the house,
bathroom and kitchen, introduced me to Annie, (who is 13
months), and excused herself to get ready. I was playing with
Annie and didn't notice the father had come up behind me. It
startled me when he suddenly said, "Well, it looks like Annie
likes you. And I can see why, you are quite pretty!" I
blushed, and it made me uncomfortable the way he looked at
me. Mrs. Laten came in and said, "She's just a child, save
your charm for someone nearer your age, (then to me), Here's
our cellular phone number, and a neighbor's. It's 6 now and
we'll be back at 10 p.m. There's some snacks in the fridge,
the remote is on that table. Annie will probably sleep the
whole time. Any questions?" "No maim, I said, No problems,
I give you a call about 9 to let you know how it is going."
Mr. Laten laughed and said, "That's good," then to his wife,
"now maybe you won't have to call every thirty minutes." They
smiled and left. The night was uneventful, the baby slept,
and I watched T.V. She awakened once, I gave her a bottle,
changed her, and she dozed back off. I called the parents at
nine, they seemed pleased to hear no crying in the
background. At ten promptly, they arrived home. Mrs Laten
gave me a ride home. She paid me $24, thanked me, and said
they'd call again.
My next 4 jobs, went similarly. I decided this wasn't bad
at all. The hair fall was troublesome, but my hair is growing
longer. I started taking care of my skin and mom said I
actually seemed to glow at times. My fingernails were long
and I kept them and my toenails polished a pretty candy
red, most of my time at home. I slept in a baby doll nighty,
Aunt Patty gave me, and now instead of running around the
house in my BVD's, I wear a bra and panties,and a baby doll
nighty.
One night a regular customer called before I was due, and
requested I come early to help her. She was wearing a fuzzy
bathrobe when she let me in.
Her name was Nina, she was quite beautiful, and seemed
in an awful hurry. She told me
Angie was in her room asleep. I was to keep an eye on her,
and come help her whenever she called. I set my purse and
bag in Angie's room and checked on her. Nina called me and I
walked down the hall. She opened a door and spun away. She
was only wearing a sheer pair of bikini panties that I could
see completely through. She walked to the bed, held up two
dresses, and asked my opinion. I was having trouble trying
not to stare at those magnificent titties, tiny waist, and
well proportioned hips. I picked the little black dress.
She smiled and agreed. She picked
up a strapless underwire bra, that pushed her mounds together,
and asked me to fasten her. She then pulled a slip over her
head, and I helped pull it down and smoothed it over her
hips. I lingered, touching her hips, and smoothing her slip.
Next was the shirred tight, clinging dress. I zipped her, (my
hands lingering on her tiny waist,)_and I complimented her on
her figure. She smiled, sat at her vanity, and asked me to
brush her hair. I took one hand and slid it under and eased
out a section and smoothly brushed it. I have done my moms
many times, and did her's expertly, no pulling, just smooth
strokes. Nina was cooing and purring like a kitty, she loved
it and didn't want me to stop, except that she was late. She
fastened some dangly earrings, touched up her makeup, checked
herself, and jumped up and practically ran out the door. It
was a good thing too because I had my very first true hard
on. It was sticking straight out, and my skirt material was
straining. If she had looked at me, she would have known I
was definitely not a girl. It was very large and hurt real
bad, and took at least 5 minutes to go down. The rest of the
night was uneventful. When Nina got back, she told me she
really appreciated me helping her out, and tipped me $10.
Back home, I told mom everything. She said that situations
like that might arise, no pun, and they were to be expected.
I appeared a girl, and women would be treating me like one.
There was nothing she could do about that. On the other
matter, she got me a panty girdle with a reinforced front
panel. "Won't happen again," she said.
Things went well. I soon had so many regular customers,
that I could work every night. About once a week, one of the
ladies would call to ask me to come help her get ready for a
special event. The word got out on my Pre- Babysitting
Abilities. I would go early to help my lady customer's get
dressed, give them advice on clothes and cosmetics. Mrs. Dorn
taught me several different ways to make Formal Hairdo's, and
several different ways to fix hair, whether it is short,
medium, or long. I have also gotten quite good at makeup,
colors and usage. I love to use hair jewelry and have so far
managed to make each lady's hair look special, they love it,
and they always tip a $10 or $20 dollar bill extra. I earned
enough money to catch up the bills, and buy a new car for
mom, and a scooter for me. I bought a cute one I couldride
while wearing a mini skirt.
I started a baby sitting club, because business has gotten
too good to handle alone. I have three girl's helping me. I
am trying to teach them how to do hair, but they seem to have
some trouble with it. So I only, continue to do my special
customer's. I run my little business out of Aunt Patty's
house. I bought a computer with Voice mail to take my calls,
and organize my schedules, if I'm away or currently a boy,
each of the girl's can retrieve their messages from the voice
mail.
I have exercised my waist down, arched my eyebrows, and my
hair has grown in length to my shoulder blades. My appearance
is becoming a problem. I have to braid my hair up tight, and
wear a cap to be a boy. I just don't look right as a boy,
anymore. Stuff like arched eyebrows and lingering mascara.
It is easier to appear as a girl, and besides, I enjoyed
wearing the pretty clothes, and smelling of perfume. I told
Mom, but she insisted we had to keep "the Boy". I went next
door and got dressed in my frilliest outfit. Aunt Patty came
in, looked at me, and asked if something was wrong. I nodded
no. She sat on the bed, patted it next to her, and said,
"Please sit with me." I did. She took my downturned chin and
gently pulled me to face her. "Tell me please, I would like
to try to help." I busted out crying, and she hugged and
comforted me. I blurted out about how mom wanted to keep the
boy. She held me, stroked my long hair, and kinda gently
rocked back and forth. It felt good, and she said she had
been thinking about something which might solve my problem.
She said I should try to calm down, and let her talk to my
mom. She asked if I would like her to go talk to mom now. I
nodded a yes, and she dried my tears, and smiled. She
started to stand, but I grabbed her and hugged her, and told
her I loved her. She flicked my nose, kissed my forehead,
and was absolutely beaming when she walked out the door. I
laid on the bed and was quickly asleep.
I awoke to mom stroking my hair. Her and Aunt Patty were
sitting on the bed, smiling at me. Mom talked softly. She
said, "Honey, if you want to dress as a girl all the time,
we'll work it out. Aunt Patty has the idea of telling
everyone that because jobs are scarce, that you,"the boy, I
mean," went to another town to stay, and work with your
Uncle. I sat up and hugged mom, Aunt Patty winked at me. I
was so happy I started to cry again.
I now go with mom to the beauty shop to get my hair fixed
when she does. I have noticed my breast developing and my
hips and legs seemed softer.. Also my voice seemed a little
higher. When I asked mom about my "worries", she said that
Aunt Patty had obtained some Estrogen for me, and she had
been giving it to me in my meals. I asked why they had not
told me. She smiled and said she wanted to surprize me. And
she was sure I wouldn't mind, seeing as how I was wearing
only girl's wear and acting so ultra feminine anyhow, they
just wanted to help. "Beside's," she said, "It will help to
not have those terrible cases of blueballs when you are
around all those beautiful undressed women." I smiled, agreed
that it indeed did hurt, and kissed and hugged her. We went
to my room. I stripped to my panties. Mom showed me some
exercises that would help make my breast even larger, and I
started doing them everyday. It seemed like no time at all
and I decided I no longer needed to wear my false titties. I
could fill a B cup, and Mom and I bought some nice sexy bras
to wear while I strived for a C cup. Aunt Patty said she had
long ago stopped thinking of me as a boy. Mom agreed that
only at occasional moments, did it occur to her that I was a
boy. It occurred to me that I myself, often no longer thought
of my self as a boy. I looked like a girl, I reacted
naturally to things like a girl, the clothes gave me some of
the feelings of a girl. Mom said I was emotionally a girl,
and I truly love the way people treat me. Yes, it is true, I
have actually become comfortable with the feminine me and
yes, even the way men look at me, no longer bothers me,
actually I kinda like it. So much so, that on occasion I will
wear something provocative. Perhaps a low cut blouse, a tight
waist, and a high cut, tight skirt. I'll walk with an
exaggerated wiggle to my hips, a bit of an extra jiggle to my
tits and perhaps a tease of a glance. On bolder occasions, I
have even did a little bit of flirty talk, to see if I can
get an Erection going, and then leave. Mom memtioned, said
she had noticed my game occassionally. She said it was a
perfectly normal thing for a beautiful girl to do. And by
that I felt encouraged. My mom saw nothing wrong in me
acting, appearing, and perhaps being a girl.
Soon, however I was going to have to face the fact that I
am still male. Next year in school, I would have to take PE.
I would no longer be able to fool all my new friends and
teachers. Alas, we worried for nothing. We toured the
school. They have private stalls, and if I were careful, no
one had to know. Aunt Patty signed me up, telling them the
records would be transferred later. She obtained some forms,
filled them out and faxed them in to the school. Some were
her daughters records. She told me all about her daughter, so
I could answer any questions I might be asked. When she told
me how her daughter died, she broke down in tears. It was my
turn to comfort her. I hugged her and talked softly.
School is lovely. I have two good girlfriends, Cindy and
Sheri, and wonderful teachers. Ever one is nice and I am
making good grades. There is a boy, John, that keeps smiling
at me, opening doors for me, and carrying my books, and well
stuff like that. Cindy and Sheri keep giggling about it, and
asking why I don't talk more to him. I shrug my shoulders,
flip my hair, and change the subject. Finally, they pinned me
down on it, and I replied, "My babysitting was taking up all
my time."
And indeed it was, one of my special regulars begged me to
take on a friend of hers. I resisted, due to lack of time,
but finally relented. I told her I would work something out.
I got a call from my new customer for Friday night, she
asked that I come extra early.
Friday Night:
I rang her doorbell. She was wearing a shorty bathrobe,
said she was Misty, and to follow her. We walked to the back
of the house. As we walked, I thought about how young she
looked, maybe about 20, 21 at the most. She told me she had a
late dinner date, and wanted me to help her get ready. She
showed me the baby's room. "Kristi" was 11 months old. I
looked about, these people were obviously rich. Misty
checked Kristi and we walked to the Master bedroom. She
slipped off her robe, turned to me and said, "What shall we
start with?" She was wearing only a pair of Thong panties,
and fuzzy slippers. She had a great body, I looked far too
long at her large, firm titties, her small waist, and well
proportioned hips. She was smiling as I motioned her to sit
at her vanity. I started by combing her hair. It was already
shiny and perfect, but she apparently wanted me just to comb.
I did and she soon exclaimed that I was indeed good at this.
She said, "I'm thirsty, would you like something to drink?" I
nodded Yes, and she wiggled her hips and jiggled her tit's,
in all her magnificient nakedest, and, noticing my stare,
seemed delighted. She came back with a fruit drink that
tasted good and made me feel warm and good. I sipped it and
continued brushing her hair. She patted the vanity bench and
told me to sit with her. I asked her if she had time, but she
told me to let her worry about time. We drank, combed, and
she asked if I had any boys enter me yet yet. I said not yet
but there was a boy at school that was paying me a lot of
attention. We giggled, and she asked for me to comb her hair
on the bed, because the bench is too hard. When I stood to
walk to the bed, I was lightheaded and giggling. She bumped
into me, and spilled my drink on my blouse, she apologized,
turned me around and unbuttoned and removed my blouse. She
put it in the sink in water. She took my elbow and steered me
to the bed. I sat down, and she sat close, facing me. She
took my hand and placed it on her breast. She just looked at
me and smiled. I traced around her nipple lightly. She laid
back, pulling me with her. She removed my bra and started
tracing around my nipples. They become larger, she smiled and
leaned to me and kissed my cheek. Then she dropped to my
tit's and started to kiss and lick them. Golly, it felt so
good, I didn't want her to stop. But she did. She said, "No
shoes in bed" and removed my high heels. Then she started
working on my titties again. It felt so good, I didn't even
notice she had unfastened my skirt, till she was passing my
knees with it. Nor had I noticed her own panties were
missing, till my hand accidently brushed her pubic hair. I
was unconsciously caressing her all over. She laughed and
asked why the girdle? She started to remove it but I
protested. She started French Kissing me and caressing my
titties, shoulders and waist, I relaxed into near oblivion.
Suddenly she pulled my panty girdle, panties, and pantyhose
off, in one quick jerk. My huge erection pointed to the
ceiling. Her eyes were like golf balls, and she fainted,
falling off the bed. I jumped off, ran around, picked her up,
and put her back on the bed. I slipped my panties back on,
and ran to get her a glass of water. As I ran, I thought-What
if the man of the house walked in, what with me running
through the house with my titties bouncing, and the wife in
there naked. So I really hurried. I sprinkled some water on
her, and I held her head up to drink some, then the baby
started crying. She weakly said, "Please check Kristi." I
went to Kristi, and changed her diaper. Then I went to the
fridge, got a bottle and warmed it. While waiting, I though
about my nakedness, there was an ruffled apron hanging, so I
tied it on. I took her to a rocker, sat, and tried to bottle
feed her, but she kept trying to suck on my titties. I
softly told her I wished I could, but that I had nothing for
her. I was trying to think what to do when she clamped down
on a nipple and started sucking. It was a strange sensation
and I let her suck for a few moments. I liked this feeling, a
maternal type instint perhaps. Then I eased the bottle into
her mouth and slowed worked her off my nipple. She hollered.
So I went and washed my tits real good, and went back to the
rocker. I then held the bottle above my tit, let a little
milk out to run down my tit to the nipple and let her suck my
nipple. It was a little messy, but Kristi was happy.
Besides, I was now doing something some women never even do,
I was breast feeding a baby. It was a wonderful feeling, and
Kristi was soon sound asleep. I looked up and there was
Misty, leaning in the doorway, smiling at me. "Very
ingenious. You are more woman than some women I know. Yes,
You are very special indeed." She walked over, picked up
Kristi and put her to bed. Then she walked back to me and
took my hand. We walked back to bed. I thought she was weak,
but she pushed me onto the bed, and jumped on top, pinning me
down. She laughed and removed her apron and my panties. She
started kissing my belly, thighs, titties, and then my
enlarging prick. She played me like a violen, soon she deep
throated me to a massive first explosion. Then was a new
experience, I wanted more. She took me and had me kiss on her
belly, thigh, titties, and soon she buried my face in her
pussy. I kissed, licked, tongue fucked, and soon sucked her
to an Orgasm. She rolled me over and mounted me. She slowly
started working her hips up, down, sideways and around and
around. She was tightening and loosing her grip on my penis
with her cunt lips. I didn't know it, but she is what you
call a -Once In A Life Time Fuck! She knew when to slow down
to keep you from exploding. And she wouldn't let you till
she was ready. But you didn't care because you were on the
edge, and the pleasure was almost painful, it was so good.
We collasped in a heap. I mentioned it was getting late, but
she said she had no dinner date, that she wanted to see how I
was with Kristi. Also she admitted, she had a bet on whether
or not I was a Lesbian. She quickly told me she would tell
no one my secret. (That I was a boy that loved to dress as a
girl.) That what she would tell them, is that I am a very
proper young lady, and excellent with babies. I leaned over
and kissed her. Then she said, "Besides, I want to keep you
all to myself. Now, we need to hurry and get you dressed, my
husband will be home soon." We both had no more than pulled
on our high heels, and undies, than he walked through the
door. Misty introduced me as the New Baby-sitter, and told
him how happy she was with me. He was quite handsome and very
nice. I called Aunt Pattie and he saw me to the door. We
stood on the porch waiting. He made small talk, but was
eyeing me pretty heavily. He seemed to be mentally undressing
me. I wondered what he would think if he knew I was a boy and
had just bounced his wife's bones. Aunt Pattie drove up, he
carried my bag and opened the car door for me. I smiled and
thanked him.
Soon, another mother with a newborn called for my services.
I told Aunt Patty about my nursing experience. She said
wonderful. We went right out and bought 2 blouses that were
flowing, loose and unbuttoned easily. Also 2 bras, that had
panels that opened, exposing my nipples. She also bought
some clear tubing, with one sealed end. She fixed it to a
standard bottle nipple. She cut the nipple wide open, and cut
a small slit in the tubing. Now I could affix it to the
bottle of milk, let the baby suckle my tit, and she could get
her milk at the same time.
I called my "Special Customers" and explained I was
overbooked and sometimes I would have to send one of my
girls. All said they understood except for three. They said
they would pay double, (WOW, $12 Dollars an hour!!) because
of my dressing help. I told them I would do the best I
could.
(continued on next page ....*smile* ) |
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