The Tomboy Tapes (TG) Part 2

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 it's 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 everyday
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!”