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K R I S T E N' S C O L L E C T I O N
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WARNING!
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The Tomboy Tapes
by Karen Elizabeth L. (address withheld)
***
One day I was reading a newspaper and suddenly found
myself drawn to an advertisement for girl's clothes. I
stared at that page for five minutes straight and when I
was finally able to put it down I had an overwhelming
urge to put on some of my sister's clothes! Luckily no
one was home and I quickly raced upstairs and threw open
the door to Cindy's closet. There, pushed to the back I
saw what I wanted, a simple, pink mini-dress that Cindy
had worn once when dad took us out to celebrate a
promotion at work. I grabbed the dress and quickly ran
back to my room and locked the door. (m-teen-cd, fetish,
tg)
***
It was going to be another one of those mornings at the
breakfast table, I thought as my mother and sister began
arguing.
"Why can't you dress up a little bit for school Cindy,"
Mom sniped. "It wouldn't hurt you to look a little more
like a girl now and then you know!"
"I look like most of the other girls mom," Cindy replied
in between bites of toast. "The days of wearing dresses
and heels to school went out with hoop skirts! Do you
want me to look like some kind of freak?"
"I just want you to look your best that's all," sighed
mom. "I want everyone to see what a pretty daughter I
have!"
"You're sweet mom," Cindy smiled as she chugged down her
juice. "Sweet but so old fashioned!"
As Cindy ran out the door mom had already turned her
attention to poor dad , hounding him about Cindy's looks
and grades. "She could do much better in school if she
were motivated, I know she could be getting A's and B's
instead of the C's she gets now. If I could just find
some way to motivate her to dress better and work
harder." Mom lamented.
"I understand dear but I can't suggest any new ways to
motivate her either," Dad was just as upset as she was
but Cindy remained cool and calm no matter how hard they
tried to change her. Sometimes it seemed as if they were
pushing a big mound of Jell-O, but that couldn't be
right, I thought, Jell-O could be molded!
Several weeks later I saw Cindy dumping several cassette
tapes into the garbage then trying to cover them over to
prevent their being found. "I've never seen you work so
hard Cindy," I joked walking into the room.
"What's up?"
"Motivational tapes," She sneered as she mixed up the
trash. "A little present from mom and dad. They figure
that if I listen to them I'll work harder in school and
it'll even spill over into my home life. I sort of hate
to disappoint them but they're not brainwashing me into
becoming some little "Goody Two Shoes!"
"Hold on a sec, I've heard a lot about those kinds of
programs and they're supposed to be really helpful! Why
not try them and see, what can it hurt?" I asked
eagerly. It wasn't so much that I was eager to help
Cindy, more that I saw a chance to be a real pain in her
side!
Cindy shrugged and pointed to the trash. "If you're so
thrilled about them, help yourself, have I mentioned
lately that you are such a suck up?" She called, leaving
the room.
"But a well motivated one!" I laughed as I cleaned off
my newly acquired treasures. Here was a golden
opportunity to show Cindy up, I'd just listen to the
tapes myself and when our parents see my report card
I'll tell them about the tapes! I put them in the back
of one of my desk drawers so that mom wouldn't
accidentally run across them, no point ruining my own
surprise! I put the tapes on before going to bed but
even with the volume nearly all of the way up I had to
listen intently to hear anything then closed my eyes and
went to sleep. The next morning I tried my best but just
couldn't remember much about the tape.
I did know though that it had been a very sound night's
sleep and that I was feeling very refreshed and anxious
to get started!
"You're looking good this morning Jim," commented dad.
"Ready for that big test today? You need an "A" to pull
your grade up for the year you know. "
"Studied all evening dad," I smiled wondering what kind
of an edge I'd get from that tape I had listened to. "I
can't wait to take it!"
"That's wonderful Jim," Mom said as she gave him a hug.
"I'm sure you'll get an A!"
"Suck up!" Scoffed Cindy as she came into the room. I
just smiled and stuck my tongue out at her, I enjoyed
being mom's favorite and I wasn't going to start an
argument with Cindy at breakfast, that was mom's job!
Mom started up right on schedule. "How were the tapes
Cindy, feeling more motivated today?"
"They were great mom, I can't wait to get to school!"
Cindy shot a quick look at me to see if he'd give her
away. We both knew the only motivation for her to get to
school was to see her friends but I'd keep quiet for
now!
"Gotta run, nice chatting!" She called on her way out
the door. Mom smiled broadly, "I think they're starting
to help her already," she told dad. "I can't wait to see
her report card! This is going to be a turning point in
her life, I just know it will"
"Yes dear, I'm sure they've helped," he mumbled through
his newspaper. "What was that about her report card?"
"Go back to your paper dear," Mom said with an
exaggerated sigh. "I'll let you know when your daughter
makes the Honor Roll!"
"Betcha I get there first!" I offered as I took small
bites of toast and sipped at my juice. Somehow I just
wasn't in my usual hurry to gobble down breakfast, must
be that tape calming me down for the test today, I
thought to myself.
Mom smiled sweetly and patted me gently on the back.
"We're sure you can make it dear, it's Cindy we're
worried about. Of course with those tapes she may just
pass you up!"
"Fat chance mom," I was suddenly defensive. " Cindy will
never be as good as me so passing me up would be a
fantasy!"
"Give your sister a chance Jim," Dad suddenly put down
his paper. "You'll feel awfully silly if she beats your
grades so don't start gloating." "Stupid too." I mumbled
under my breath.
Dad took a swipe at me with his rolled up paper. "I
heard you, now shut up and give the girl a chance. We
went through a lot of trouble getting her to listen to
those tapes and we're expecting to see results."
"All right, I'll keep quiet," I replied as I sulked out
the door feeling very let down. "But don't expect too
much, we all know there isn't that much to work with!" I
wanted to add; "Especially since she's not even
listening to them He thought to himself," but I'll just
bide my time!
"Thanks for not giving me away at breakfast," Cindy told
me later. "That was very sweet of you."
"I didn't do it for you," I insisted. "If I gave away
the story mom would've taken the tapes away from me and
I want to keep them."
"Hey I don't care either," Cindy shrugged as we walked
to class. "You're welcome to all the stuff mom and dad
give me. Maybe there will be lessons on being a better
suck up in one of them!" She laughed derisively.
"Suck up? Me?" I exploded angrily as my face becoming to
burn.
"Dad rushed to your defense at breakfast this morning,
so maybe you've been doing a little sucking up yourself?
Playing the old "Daddy's Girl" routine again?" Cindy
laughed and brushed her hair back with a quick flick of
her wrist. "A little kiss goes a long way with guys,
especially when it comes from their daughter!"
"I bet them that you'll never be nearly as good as I am
and kisses to dad won't make a difference," I scoffed
unable to help but feel that she was somehow cheating.
"I'm smarter, more motivated and with those tapes I'll
pass you in a flash!"
"Don't care, I'm still way prettier that you!" She
laughed as she threw back her head and fluffed her hair.
*
Weeks went by with Cindy and mom still occasionally
arguing over breakfast, Cindy was a slacker, there was
no doubt about that but her grades weren't that bad.
They both knew that the argument had deeper meaning for
mom, Cindy had never been the sweet little girl of mom's
dreams, she despised baby dolls, and fought being
dressed up in pretty outfits even as a child. Even if
Cindy had made the Honor Roll mom would not have be
satisfied unless Cindy accepted the award in a beautiful
gown!
"Are you doing better in school Cindy?" Mom would ask in
an innocent tone.
"School still sucks mom," Cindy would nonchalantly shoot
back to mom's horror.
"Sucked then, sucks now, and it will go on sucking
forever!" "I saw a really cute outfit at the mall
yesterday honey," Mom would venture in a vain attempt to
move the conversation around to what she really wanted
to talk about. "Maybe I'll pick it up for you, it would
make a nice school outfit."
"Got enough jeans and stuff mom thanks," Cindy would
shoot her down in flames. "Besides I'm not going to
school in one of those "Little Miss Muffet" outfits you
like so much. Too frilly for me!"
Suddenly a picture of a frilly dress with puffy sleeves
and a full skirt popped into my head. "Such a pretty
outfit," I found myself thinking. "Cindy's so lucky and
she just doesn't realize it! I'd kill for a dress like
that."
I nearly choked on my milk as I struggled to regain my
thoughts. "What made me think something that crazy," I
wondered. "Why would I want to wear a dress?"
"What's your problem?" Cindy asked. "Thinking of getting
one of the cheerleaders into an outfit like that? I'd
bet you'd love that!"
"I wasn't thinking anything at all!" I insisted, afraid
that somehow she knew about the words that wouldn't go
away. "But now that you mention it mom's right, you
would look nice in a pretty outfit like that. It
wouldn't hurt to look a little more like a girl you
know! Think of how nice you'd make mom feel."
"If you're so concerned about mom's feelings why don't
you take the job?" Cindy shot back maliciously.
"What job, what are you talking about?" I asked puzzled
that I had somehow lost track of the conversation.
"Daughter of the family!" Laughed Cindy as she waved her
hand towards me. "There you go mom, your very own sweet
little girl just waiting for you to dress her up in a
pretty little dress with patent leather shoes, a little
purse and gloves. You two could have a great time
shopping for cute little party dresses!"
"You're nuts!" I shouted ready to reach across the table
at her. "You're a sicko too talking about stuff like
that! It's just that... oh forget it!"
Cindy looked at me strangely for a second or two before
rushing off to meet her friends.
I suddenly had a terrible feeling in my stomach. How did
I let myself get involved in a discussion about my
sister's wardrobe, I must be losing my grip!
"Gotta roll," I blurted, grabbing my books and running
out the door. I pushed myself to think of an upcoming
trigonometry test to prevent those strange thoughts from
returning.
"Here ya go Jim," Cindy announced as she tossed several
new tapes onto his bed a few days later. "Mom's
motivational series, part two!" She laughed as she threw
herself into a chair.
"I don't know if I want these after our argument," I
said even as I pulled the tapes towards me.
"You were awfully nasty to me that morning you know."
"You're breaking my heart Jim," Cindy sneered. "I seem
to remember that you jumped on mom's side and took a
cheap shot at me! Now you've got the nerve to sit here
and pretend you're precious little feelings have been
hurt. Bummer!"
"But honestly Cindy," My voice took on a tone of
sadness, of being misunderstood. "I was really trying to
help you, you could look so pretty if you got dressed up
once in a while..."
Cindy dropped to her hands and knees and began scouring
the room. "Come on out, I know you're here," She called
out.
"I'm trying to have a serious conversation with you if
you don't mind!" I shouted as Cindy continued her
searching. "What in the world are you doing?"
"Looking for mom of course," She grinned. "I know she's
hiding here somewhere, I can hear her! I can't figure
out how she got your mouth to move as if it were really
you talking but I am impressed!"
"Get out of here you idiot!" I screamed as I finally
lost my patience. "You're too stupid to realize how nice
you could look and how happy you'd make mom!" Cindy
turned and smiled. "The jobs still open and you can help
yourself to any dress in my closet!"
As she slammed the door behind her I threw myself on my
bed and fought back the tears. Cindy was right, I had
sided with their mother against her but why? It wasn't
even my usual cheap shot at her, I was really trying to
help!
Now though Cindy thinks I should be some kind of sissy
running around pretending to be a girl and if that's not
bad enough there are those thoughts! The thoughts kept
popping into my head at the most inopportune times, just
that past week I had been in the middle of a History
test on Victorian England and couldn't seem to force a
picture of myself all done up in a pretty lace dress
with a floppy hat and parasol from my mind.
Not long afterwards I began to let my hair grow even
though my parents badgered me daily to get it cut.
"I think I look good with long hair mom," I patiently
explained. "Lots of guys wear their hair long and some
even pull it back in sort of a ponytail! It looks really
great and it's the latest style."
"The latest style for boys is to look like girls?" Dad
asked with barely concealed scorn. "Sounds great, first
you got an ear pierced and now you're letting your hair
grow. Are you nuts or what?"
"Gotta keep up with things dad or I'll end up as a
nerd."
"You already are a nerd," Laughed Cindy. "Now you're
just a funnier looking nerd!"
"Enough from both of you," scolded mom. "Jim, If you're
going to have long hair you better make sure it's kept
neat and clean or I'll cut it off while you sleep! And
Cindy, listen to those tapes, I don't plan on throwing
money away!"
"Don't worry mom, I'm making good use of them!" Cindy
assured her after a quick glance my way. I knew that I
wasn't about to call her a liar, I enjoyed the tapes far
too much to cut off my supplier.
"And I'll keep my hair nice mom, I promise," I added
feeling relieved that I could let my hair grow. Lately
having long hair had become very important to me but I
just couldn't seem to focus on a reason.
"Maybe," I thought to myself. "I'm just trying to outdo
Cindy again by showing her that I could look good in
long hair when she insisted on keeping hers short."
What I couldn't bring myself to admit though were the
thoughts I was having of how pretty I would look with
long curly hair! The arguments between my sister and
mother continued on as did the tapes which as far as I
was concerned kept getting better and better. The last
bunch promised motivational messages mixed in with songs
from some of the hottest rock groups, I would spend
hours playing the tapes over and over while studying or
drifting off to sleep.
I kept waiting for my grades to take a giant leap
forward, after all I played the tapes religiously and
mom had promised Cindy they'd make a big difference in
her life if she only relaxed and let the messages work.
I'd spent many an evening with just a small light on in
my room, headphones clamped to my ears, relaxed,
listening, absorbing, and waiting.
One reason I concentrated so hard on those tapes was
because those goofy ideas kept coming back to me, you
know the ones about wearing pretty dresses and having
long curly hair. No matter how much I concentrated on
those tapes though the thoughts kept coming.
One day I was reading a newspaper and suddenly found
myself drawn to an advertisement for girl's clothes. I
stared at that page for five minutes straight and when I
was finally able to put it down I had an overwhelming
urge to put on some of my sister's clothes!
Luckily no one was home and I quickly raced upstairs and
threw open the door to Cindy's closet. There, pushed to
the back I saw what I wanted, a simple, pink mini-dress
that Cindy had worn once when dad took us out to
celebrate a promotion at work. I grabbed the dress and
quickly ran back to my room and locked the door.
I swiftly removed my shirt, undid my belt, unfastened my
jeans and stepped out them. My heart was pounding and my
hands were shaking as I pulled Cindy's dress over my
head then tugged it over my hips. Just as I finished
adjusting it I was overcome with the most wonderful,
peaceful, feeling I'd ever know. I stared at myself in
the mirror, unable to move, unwilling to change. "This
is Heaven!" I thought.
I must have worn that dress for nearly half an hour, I
practiced posing in different positions, walking, and
sitting until just as suddenly as the urge hit me to put
it on I felt that I had to take it off. I couldn't stop
for a second until I had the dress safely back in
Cindy's closet and had my pants back on. My heart was
still beating wildly and my hands were sweaty and
shaking.
I couldn't believe that I had actually put on one of
Cindy's dresses but my unbuttoned shirt and loose belt
were proof that something terrible had happened. Or had
it? I just wasn't sure and it was driving me mad! After
that I found myself doing strange things that made me
think I was going nuts.
One day I was taking a shower and reached to shut the
water off only to pick up the razor Cindy used to shave
her legs. I stared at the razor and then at my legs.
Suddenly I was disgusted by the hair on my legs,
lathering up with a bar of soap I sat down on the side
of the tub and removed every strand of hair from my
ankles to my butt! Whatever demon was possessing my mind
wasn't satisfied though and without giving it a second
thought I shaved my underarms too!
I ran my hands along my now smooth legs and admired the
shapeliness I never before realized they had. They were
smooth, silky, very pretty and I was very happy! I
smoothed lotion over them to help keep my skin soft and
silky then carefully patted myself dry with the
fluffiest towel I could find before reluctantly pulling
on my briefs and jeans. It wasn't until I was sitting on
my bed putting on a pair of socks that I realized with
horror what I had done! "What's wrong with me?" I
wondered as I absentmindedly counted the strokes of the
brush through my hair.
After it happened I was sure that everyone I met could
somehow tell that I tried on my sister's dress,
fortunately I quickly realized that there was no way for
that to be possible. It happened in the privacy of my
room, I took it off and put it away again and there was
nothing left to show for it, I was safe. Or at least I
was until now! Now I'd be stuck wearing long pants even
though the weather was warming up and everyone else
would be wearing shorts.
I was stuck until the hair on my legs grew back, if it
ever would! If that wasn't bad enough there was always
the problem with my underarms, if I wore my favorite
muscle shirts, I couldn't raise my arms lest my girlish
underarms be seen. "Boy, I really screwed up this time,"
I thought as I began my hundred strokes on the other
side of my head. Once I finished my daily brushing
routing I gathered my hair and pulled it back into a
ponytail.
"Too bad I can't use one of Cindy's scrunchies to hold
my ponytail," I thought to myself as I put a rubber band
around it. "These rubber bands are giving me split
ends."
At school I tried to concentrate on what was going on in
class but I kept getting distracted by the girls in my
classes. I couldn't stop staring at some of them,
especially if they wore a skirt or dress! I didn't care
what Cindy said about not wearing dresses to school,
these girls wore them and they looked great! Judging
from the way they acted they really seemed to enjoy
being dressed up, they walked differently, they sat
differently, everything they did seemed so feminine that
it drove me wild and to my amazement jealous!
I had to be crazy! I'm supposed to be a normal teenage
boy lusting after pretty girls yet more and more I was
envious of their pretty clothes, the way they wore their
hair, and the way they moved. I wanted to be just like
them, to have long, pretty hair, to wear pretty dresses
and nylons, to tantalize with a slight scent of my
perfume. It was insane, positively insane but I couldn't
control the feelings building up in me, I wanted to be
the daughter mom always wanted Cindy to be! I wanted to
wear pretty dresses to school, to do my nails in pretty
colors, I wanted to experience the delightfully
wonderful world of a pretty young woman!
One day in school there was a pep rally and the
cheerleaders were allowed to wear their uniform's to
class. I was in Hell as I watched those pretty girls in
their short skirts walking down the halls laughing and
having the time of their lives. Why was I stuck in these
awful pants and plain shirt when I should be wearing
something colorful and pretty? I had to do something
about it but until I got home I would have to endure the
torture of seeing these girls so self confident in their
femininity practically daring me to join them!
I couldn't begin to figure out why I felt the way I did,
I never noticed those things before but suddenly they
seemed so important to me! I tried to force the thoughts
out of my mind but as before they came right back,
stronger each time. One day I walked into the house
after school and was relaxing with a sandwich and cold
glass of milk when I was overcome with a strange
feeling.
No one was home but I'm not sure that would have made a
difference, I had something to do and I'd simply die if
I couldn't get it done! I went straight to Cindy's room
and quickly pulled the pink dress from its exile at the
back of her closet. This time though I wasn't going to
rush back to my room to try it on as I had many times in
the past few weeks, this time I was going to do it
right, the way Cindy should!
I opened every drawer in her dresser until I found
exactly what I wanted, a pair of pretty satin panties
that still had the tags on them, a bra, white pantyhose
that Cindy had worn once, and a white half slip trimmed
in lace. Carefully cradling my treasures I hurried off
to my room before I came to my senses and put everything
back.
Just as I had done so many times in the last few weeks I
locked my door and carefully checked to make certain
that it couldn't be opened. I considered pulling my
drapes shut but there aren't any other houses close
enough for anyone to be able to see in my windows but
the possibility made what I was about to do all the more
exciting!
I quickly removed every stitch of boy's clothing I had
on then with trembling hands I pulled the satin panties
up to my waist. I had tried on Cindy's panties before
but they had all been cotton, softer than any of my
briefs but nothing special, just plain white cotton
without even a pretty little flower to brighten them up.
Of course it felt very exciting to wear girl's panties
but the feeling was nothing compared to what was
happening to me now, the satin was so soft, silky, and
cool against my skin that I had an instant erection!
What a contrast, pretty satin panties being pushed out
of shape by something that they were never meant to
hold!
I thought of an assignment I had recently done for
English class on contrasting things, too bad I could
never write about the contrast of the utterly feminine
panties and an utterly masculine erection! It took a bit
of work to get the bra on, this was to be my first time,
guess I was saving it for a special moment, but finally
I had it hooked in back and stuffed with some socks
until I had close to what I figured Cindy's bust size
was.
The pantyhose were tough, I'd seen commercials and
movies where a woman would start pulling on a pair but
once again it was my first time and I was scared to
death of putting a run into them, I'd never explain
something like that away. I carefully inserted my right
foot then slowly pulled them as far up as I could before
putting my left foot in.
When I finally had them worked up as far as my thighs I
hesitated for just a second feeling that I was on the
verge of taking a very important step. A deep breath and
I slowly worked them all the way over my thighs and
unrolled the waistband, my heart pounding in my ears,
goosebumps popping up on every piece of flesh!
"What was wrong with Cindy?" I wondered. "I'm only
partially dressed and I can't believe how wonderful
these clothes feel! How could she prefer cotton panties
to these dreamy satin ones I wore, why would she ever
wear socks when she could wear these stockings which
were making my legs look so pretty and sexy!"
The slip made me look much better hiding the unsightly
bulge in my panties. The pantyhose helped keep it in
check but now with the slip on I looked more like a girl
with my pretty, nylon covered legs extending beyond the
lace hem of the slip.
Even though I was still excited I was becoming much
calmer, more sure than ever that I should dress this
way! I lowered the dress over my head with all the
confidence and self assurance any girl my age would
have. Every part of my brain was now telling me that
this was natural, I was a young woman and this is how I
was expected to dress!
Completely dressed I was shocked to see Cindy's
reflection in the mirror, I nearly panicked until I
realized that Cindy wasn't in the room, I was alone, the
girl in the mirror was me! Sure there were a few rough
edges, Cindy had a few more curves than I did but I was
sure that with a little padding here and there I could
easily look every bit as pretty as Cindy did on those
rare occasions when she did get dressed up. I'd love to
have her see me now and tell me that although I'm
smarter she's prettier, I'd show her who the prettier
sister was in this family!
My time in Heaven ended all too quickly, I had to hurry
to undress and put things away before anyone came home.
I was sure of one thing as I put the clothes away,
something had gone terribly wrong, I'm supposed to be a
pretty girl, not an average looking boy!
From now on I vowed, I'd work harder until I could do
everything a girl did and do it the way a girl did. When
I was finished my family would realize that although
Cindy was just an overgrown Tomboy I was a young lady
and they'd treat me like the young woman I was meant to
be!
I admired myself for a little while until the feeling
vanished as suddenly as it had come on and I found
myself utterly disgusted by what I had done. I stripped
off Cindy's clothes as fast as possible then quickly
donned by own. After I finished putting my sister's
clothes back I returned to my snack but found it
difficult to eat with the tremor in my hands.
What had happened to me?
I had seemingly lost all control over my actions but I
was too ashamed to talk to anyone about it Things kept
happening more and more after that, I had an
unquenchable desire to dress in Cindy's clothes, to
shave my legs and underarms, and keep my hair long and
pretty and I wasn't feeling nearly as guilty about it
anymore! Keeping my legs and underarms smooth and silky
became a part of my daily shower ritual, brushing my
long hair wasn't a job, it was fun! I even graduated
from wearing Cindy's clothes alone at home to wearing
panties to school!
It was so scary yet exciting, I'd be dressing after a
shower and boom the urge would hit me! I'd wait until
Cindy was downstairs then sneak over to her room and
borrow a pair of panties. In school I had to be extra
careful in the way I moved, sat, or stood to prevent
anyone from seeing the waistband of my panties peeking
over my pants.
I was trapped, terrified that I'd be caught! Every
afternoon when school ended I breathed a sigh of relief
that I hadn't been discovered and vowed that I'd never
do it again but the next morning would find me once
again pulling on a pair of panties!
The feelings had grown so intense that I started to
dress more and more often and wanted to wear different
things other than Cindy's pink dress. I tried on her
jeans, her shorts, and her nightgowns, if it was in her
closet or her drawers I at least tried it on, sometimes
as I did with her panties, wearing them with my boy's
clothes.
It was nearly impossible for example to distinguish her
white socks from mine but it made me feel like I was
fooling people when I wore them instead of my own! I'll
never forget the first time I wore them instead of my
own, I was sure that mom, dad, Cindy, and the entire
world could somehow tell that I was wearing a pair of
girl's socks but no one said a thing or even looked at
my feet!
After going through Cindy's boring wardrobe I somehow
came up with the idea of checking out my mother's
clothes. She and Cindy were about the same size and
whenever she went somewhere special she wore some of the
most gorgeous outfits! I figured if she hounded Cindy so
much about wearing more feminine clothes mom might just
have some really pretty things stashed away in her
drawers and I couldn't wait to try them on.
I held out for over two more weeks before I finally had
to give in to the urges. Mom and dad were going to be
spending a Saturday visiting some out of town relatives
and Cindy would also be gone until late evening. The
instant I had the house to myself I locked all of the
doors then ran to mom's room undressing as I went. When
I reached her closet I had a strange feeling of
excitement seeing the dresses, skirts, and suits of
every color and style which called out to me to try them
on!
The first outfit I picked to try on was a dark blue
dress with sheer sleeves that mom wore when she and dad
went out for their anniversary dinner. The material was
very sheer but there was something like a built in slip
under it to keep it from being totally see through. I
couldn't wait to try it on but I wanted to check out
mom's lingerie first in the hope I'd find something
pretty to wear under the dress.
When I opened her dresser drawer I couldn't believe my
luck, instead of white cotton I was staring at satin,
nylon, and silk in so many different shades it was as I
was staring at a rainbow! Almost every pair of mom's
panties were lace trimmed, some were made of nothing but
a stretch kind of lace, while others were so sheer and
sexy I found myself blushing!
For a moment or two I was shocked to think that my own
mother wore these kinds of clothes then my heart began
to pound as I realized that soon I too would be wearing
such feminine and sexy items! I picked out several
different matching panty, bra, and slip sets to try on
but the one I couldn't wait to wear was black,
beautiful, shimmery, silky, black with lace at the
waistband of the panties, lace at the bottom and side
slit of the full slip, and if that wasn't enough to
drive me crazy the top part of the bra's cups were
nothing but lace!
I couldn't get out of my regular clothes fast enough, I
was all set to tear my shirt when my fumbling fingers
finally undid the last button. I pulled down my briefs
but instead of placing them on a neat pile with the rest
of my things I gleefully kicked them across the room, I
wanted to have nothing more to do with such ugly,
confining clothes, I was a young woman exploring my
femininity and boy's briefs had no place in that world!
If I still had any insignificant doubts about what I was
doing they were erased forever when I slid the dress
over my head, over my bra, panties and a pair sheer
black pantyhose. I wanted to run out into the street and
shout "I love being a girl" but I hadn't yet gotten the
hang of the black heels I had also borrowed from mom's
closet.
I found a string of mom's pearls and after a few seconds
work I managed to get them around my neck and fasten the
clasp. I slipped a delicate gold bracelet on my wrist,
fastened a dainty chain around my ankle, then set off on
wobbly ankles for mom's vanity and makeup across the
room. I reached the vanity without breaking an ankle
then smoothed out my skirt as I'd watched girls at
school do before sitting down.
My reflection in the vanity mirror was pretty good, I
looked a lot like Cindy might look in this dress without
makeup on, but that wasn't good enough for me. I wanted
to be the pretty sister and in front of me were the
tools I would need to complete my journey from plain to
pretty. I just hoped I could master them without anyone
discovering what I was doing, I wanted to surprise mom
with a daughter who was pretty and feminine, a poised
and confident young woman!
I spent the rest of the morning and the entire afternoon
in mom's room experimenting with makeup, clothes, and
hair all the while worried about the feeling that I was
supposed to have been a girl. Fighting the feelings
wasn't possible any more, I was caught in a web of satin
and lace and there seemed no way out. I began to think
of how happy I would be to let mom buy me skirts and
dresses to wear to school! Cindy might rebel at the
thought of wearing a pretty dress now and then but I
wouldn't!
I would learn the proper way to dress, do my hair, wear
makeup, and behave as a proper young woman and mom would
be so proud of me! I had so much to learn but I wasn't
finding a whole lot of time to study. Mom and dad were
staying home more on the weekends and with finals coming
up Cindy was actually coming straight home from school
to study.
Luckily I was able to sneak some of mom and Cindy's
things into my room where I hid them in the back of my
closet. In the afternoons I'd go to my room to study but
it wasn't school work I was studying, instead I was hard
at work trying to master makeup and hairstyling.
One Saturday afternoon after finishing showering and
shaving my legs and underarms I was sitting on my bed
combing out my hair as Cindy walked past my room. "Your
hair's getting pretty long," She laughed as she watched
me carefully pull a comb though his hair. "Almost ready
for some pretty ribbons and bows!"
Cindy's comments brought the old feelings crashing back
on me, I shouldn't want long hair and I certainly
shouldn't have been wearing the panties I had on. I
wanted to cut my hair off right then and there, to
change into a pair of boy's briefs and burn the panties.
I wanted to, but then I thought of how pretty my hair
would look tied back in a ponytail with a pretty ribbon
holding it in place. I thought of how smooth and soft
the panties were and how rough and heavy my briefs were
and it wasn't a contest. I couldn't do anything about
what was happening to me and I knew it. Lost in thought
I dropped the brush I had in my hand and bent over to
retrieve it.
"Those are my panties!" Cindy exclaimed as she spotted
her satin panties.
"What are you doing wearing my underwear you little
pervert?"
"I can explain Cindy, just gimme a chance," I begged.
What are you trying to pull?" Cindy asked suspiciously.
"What are you doing with these things?"
I spent a long time trying to explain things to Cindy
who seemed to have a hard time understanding what made
perfect sense to me, at least at that time. Cindy stared
at me as if I came from another dimension. "I don't
understand but I think you'd better tell mom. Dad's
gonna freak, that's for sure!!"
"I guess he will," I said sadly. "I can't help it
though, I should have been a girl, just like you. Only
thing is that I really like getting all dressed up and
wearing frilly stuff, I want to be the kind of girl mom
wants you to be, all satin and lace and stuff!"
"So what do you need from me?" Cindy asked cautiously.
"I can't do anything about dad, I'm sure mom will be
proud of you, surprised as all heck but proud!"
"I'm having a lot of trouble learning to apply makeup
and fix my hair," I told her. "I was hoping you could
help."
"But you're a boy!" Cindy exclaimed, exasperated. "Boys
don't wear dresses, they don't wear makeup, and they
don't run around in their sister's underwear! Look, you
and I weren't exactly close friends but I just don't
think I can handle helping my brother become a girl."
"Please Cindy, I'll be a great sister I promise," I
begged. "If you're that serious about being a girl, why
not ask mom to help? She knows more about makeup and
hair styling than I do." Cindy suggested. "You're going
to have to tell her anyhow you know, why not do it now
and let her help?"
"You don't understand Cindy, I want to surprise mom. I
don't want to say anything to her until I can do
everything any other girl can do, until I'm as much of a
girl as I can be!"
"But what if someone finds out about you? What about the
other kids at school?"
Cindy challenged, obviously trying to weasel out of
helping me. "I guess they're bound to find out," I
shrugged. "But that's not going to make any difference
at all. I'm going to be a girl whether they like it or
not! It took a lot of convincing before Cindy agreed to
help but it's not every day that a girl's brother asks
her to teach him how to be a girl.
She didn't wear makeup so she couldn't teach me much
herself but she did promise to pick me up a few
magazines and she even agreed to buy me my own makeup!
She was never this nice to me as her brother, it was
obvious that being her sister was going to be much
nicer!
Mom wasn't letting up on Cindy, the constant battle over
Cindy's dressing continued but Cindy didn't complain as
much anymore. She simply take the clothes, jewelry, and
makeup mom would buy her and put them in her room for me
to use. It was a good system, I got the latest styles,
makeup that was perfect for me and since mom
occasionally checked and found that the stuff was being
used she eased up on Cindy. Mom was happy, Cindy was
happy, and I was ecstatic!
After a few weeks had passed Cindy seemed to forget her
reservations about turning me into a girl and became
very helpful in my drive to replace my boy's clothes
with girl's clothes. The first thing to go were my
briefs of course, replaced by the prettiest, silkiest
panties Cindy could find for me. I replaced my white
sweat socks with girl's socks, bought several girl's tee
shirts like Cindy wore and even found a pair of girl's
sneakers that were plain enough to pass as boy's
sneakers.
It was so wonderful for me to go off to school wearing
panties, a girl's tee shirt, girl's socks and sneakers,
the idea that I was somehow trapped, that I couldn't
possibly change into boy's clothes was both scary and
exciting! No one ever batted an eye though, I was just
another long haired guy as far as my friends and family
were concerned!
One day after school had ended for the year though mom
started picking on Cindy wondering why she'd spend so
much money on makeup and pretty clothes then never wear
them out of the house. "Don't worry 'bout it mom," Cindy
replied trying to avoid ruining my surprise. "Maybe
someday when you quit bugging me about it I'll get
dressed up and let you take me shopping. Until then
don't bug me!"
That was the wrong thing to say to mom and Cindy quickly
found herself on the receiving end of a tongue lashing
that would have gone down in the history books as the
greatest of all time. She was being grounded for a
month, her phone privileges were being taken away, and
there was more to come until I spoke up.
"Please don't yell at her mom," I pleaded. "She's only
trying to help me surprise you."
Mom stopped suddenly, her momentum in the argument lost.
"You're not involved in this Jimmy, please mind your own
business."
"That's just it mom, I really am involved and I'll prove
it!" I told her as I left the table. I went to my room
and from a box I had hidden in my closet removed
pictures that Cindy had taken of me modeling different
outfits. returning to the kitchen I laid them in front
of mom and proudly announced, "This is my surprise, the
daughter you always wanted Cindy to be!"
Mom studied the pictures for a few seconds then smiled
broadly. "I'm sorry Cindy, you look lovely in these.
Were you planning on surprising me?"
"Not exactly mom," Cindy hesitated for a long time then
glanced towards me.
"That's not me those pictures."
"Of course it's you?" Mom seemed puzzled, glancing at
the pictures then at Cindy. Finally she took note of
Cindy staring at me. "If it isn't you then who is it?"
She asked looking straight at me.
"It's me!" I replied filled with pride. "I hope I look
good enough to make you proud of me!"
"T..t..this is you?" Mom gasped as dad pulled the
pictures from her hand.
"What in God's name are you up to?"
"Oh my Lord, " Dad uttered softly. "Tell me this is some
sick joke you're pulling Cindy."
"I thought so too at first dad but Jimmy convinced me
that it wasn't," Cindy explained, "Believe it or not,
that's Jimmy in those pictures."
Mom looked at me dumbfounded, "Jimmy?" She asked, her
voice strained. "You'd better have an awfully good
explanation for this."
"How can he possibly explain these!" Dad thundered as he
threw the pictures in front of me. "This is sick!"
"I don't understand," I said sadly. "It just seemed to
happen all of a sudden, I don't know why."
"Will everyone please calm down," Mom interjected
stepping between me and dad. She laid the pictures in
front of me. "Now young man would you please explain why
you're wearing girl's clothes in these photos?" I
thought for several seconds on just how to answer mom's
question before deciding not to drag things out. "I want
to be a girl, that's why."
"You what?" Dad asked seemingly stunned at my
announcement.
"Are you serious?" Mom gasped. "You can't be serious!"
"A girl, you want to be a girl?" Dad was obviously
shocked, his face had lost all color and his eyes were
bulging. "When did this happen? You've never mentioned
anything like this before."
"I can't remember wanting anything more than I want to
be a girl," I explained as best I could. "Maybe I didn't
realize it before but now I'm absolutely certain that I
want to be a girl."
"But why?" Mom asked trying to remain calm even though
she appeared to be on the verge of crying. "What made
you decide you want to be a girl?"
"I don't really know how it happened mom, I tried to
ignore it and be like any other boy but I couldn't help
feeling that something was wrong. I started trying on
Cindy's stuff and then I knew for sure, I should have
been a girl." By now I was on the verge of tears.
"Please daddy don't be mad at me, I can't help how I
feel."
Dad stared at me but the look of disgust was beginning
to fade. "When did you start thinking that you should
have been a girl? What could suddenly make a normal boy
decide that he'd rather be a girl?"
"I'm not sure," I said as I wiped a tear off my cheek.
"The idea of dressing up seemed to come a couple of
months ago and it just got worse and worse. I tried not
to give in but the feelings were just too much for me,
one day I was taking a shower and wanted to shave my
legs and underarms, before I knew what was happening I
was wearing Cindy's dresses then mom's underwear."
"Wait a second," Cindy announced, an odd look in her
eye. "Mom, when did you start getting those tapes for
me?"
"I don't know," Mom replied offhandedly. "Three, maybe
four months ago why?" "And they were just supposed to
motivate me more in school right, nothing else?"
Mom hesitated before answering. "Not exactly, school was
just a minor part of it, actually they were supposed to
make a young lady out of you but I guess they were a
waste of money."
Cindy started to laugh and soon had tears rolling down
her cheeks. "No, actually they would have been worth
every penny you paid for them, if I listened to them!"
"I'm confused," Dad said. "Those tapes were supposed to
make you act like a young lady but you never listened to
them, what's the joke? "I wanted to throw them away,"
Cindy laughed as she dried her eyes. "But Jimmy stopped
me, he's been listening to them all along! You got the
sweet young lady you wanted mom, it's just that she's
your son!"
I was wearing a big smile when mom and Cindy turned to
look at me, I was thrilled that mom had referred to me
as a girl and I knew I'd show Cindy that I was no bimbo!
"You're really getting into this aren't you? Cindy
prodded me. "The idea of having to spend the rest of
your life as a girl doesn't bother you in the least does
it?"
"I admit that it's a little bit scary but if I'm going
to be a girl at least I'm going to be pretty!" I smiled
as I tucked a strand of hair behind my ear. "Those tapes
worked so well that I'm really looking forward to
becoming a girl! I'll get to wear soft pretty clothes
like these, have my hair done, and I don't have to pay
to see a movie anymore!"
"That's a definite plus, I gotta admit," Cindy laughed
as she gave me a hug. "It's going to be different having
a sister around, mind if I borrow an outfit now and
then?"
"No sweat, you were nice enough to share your things
with me so help yourself to anything I get!" I felt a
closeness to Cindy that I never really felt before. We'd
always kept each other at arms length, I didn't
understand her world and she didn't understand mine. Now
our worlds would be the same! "Let's quit gabbing, dad's
waiting to meet his new daughter."
With that mom gently took me by the elbow and led me to
where dad was waiting. He seemed somewhat confused at
first but then he smiled and told me I looked very
pretty. That compliment from dad was the sweetest thing
he'd ever said to me, if he could bring himself to
accept me as a girl my life had just become so much
easier!
"Thank you daddy," I whispered as I kissed him on his
cheek. "I promise I'll make a good daughter for you."
The kiss seemed to cause dad to fall into a trance for a
few seconds. Shaking his head he snapped out of it and
sighed. "I love you very much Jamie but it's going to
take a little adjustment before I'll get used to your
calling me daddy and kissing me like that."
I kissed him on the cheek again then threw my arms
around him. "Tough daddy, you'll just have to get used
to it!"
Mom got all misty eyed and threw her arms around me. "Oh
Jamie, it's so wonderful to have a daughter that would
want to wear such feminine things! I can't wait to buy
you all sorts of pretty outfits and show you how to look
pretty and sexy!"
We had a wonderful time that evening, dad seemed proud
to have three lovely ladies for dinner dates and mom was
happy when Cindy relented and wore a dress too! I don't
remember having such a wonderful time with my family
before and knowing that it meant dad's acceptance of me
as his daughter just made things that much more
wonderful!
*
The next morning I wondered if I had been dreaming until
I noticed the nightgown and panties I was wearing. In
all of the months that I'd been dressing up I never had
the courage to dress up overnight but now I was wearing
a very cute little nightgown and if that wasn't proof
enough there hanging on my closet door was the dress I
had worn. It was true then, I really was a girl!
At breakfast everyone acted as though there was nothing
unusual for me to be wearing my pink babydoll nightgown
but I got a very rude surprise when I sat down on the
cold wooden kitchen chair. I always wore some type of
bottoms as Jimmy and it simply had never occurred to me
that the thinner fabric of girl's clothes would not be
much value against a cold chair!
"Now do you understand why I don't wear nightgowns to
breakfast?" Cindy laughed as my eyes grew wide with
shock. "Guess there's a few little tricks you still need
to learn, like making sure you're wearing something warm
in the mornings!"
"I'll make sure I remember that!" I laughed as I
struggled to pull my nightgown further down. "Gotta
admit, I never thought of that before!" After breakfast
I was thankful to change into a pair of cutoff shorts
which made me feel much more secure on cold seats!
Cindy reached down and pulled out a large brown envelope
she had been sitting on. "Here are a few other things to
get used to Jamie dear". I opened the envelope and
nearly fell off the chair when I saw a birth certificate
made out for a Jamie Lynn, with the sex clearly marked
Female! The surprise didn't end there because the next
thing to fall out was a temporary driver's license also
made out to Jamie Lynn!
"Put on something pretty Jamie," Dad said as he kissed
me on the cheek. "Once you get your picture taken you'll
officially be female!" I was sobbing tears of joy and
had to muster all my composure to thank everyone for
being so good to me!
It seems like so long ago that I became Jamie but
looking back it has only been months since I had the
final operation. I'm in college now having a wonderful
time and have no regrets over what happened to me within
the last year.
Dad has accepted me completely and has even managed to
be civil towards my dates when they pick me up. Mom is
thrilled to finally have the daughter she always hoped
for, Cindy and I have become much closer and to add to
mom's delight she has even begun taking an interest in
her looks, frequently borrowing my clothes!
It all worked out for the best, mom got the change she
was looking for in Cindy, I got a whole new lifestyle
that I've really come to love, and dad now has three
women to pamper him!
END
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Please keep this story, and all erotic stories out of
the hands of children. They should be outside playing
in the sunshine, not thinking about adult situations.
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Kristen's collection - Directory 66