The
Adventures of Jessica Part 1: Discovery
By
Unholy1
I walked
briskly down the street, school had just gotten out and I knew that the sooner
I got home, the more time I would have to spend in my own secret fantasy
world. Mom would be home just a few hours
after me, as she should have left just recently to go to the airport to pick up
my older sister Cate who was returning home from spending the past year in
Arriving
home, I quickly slipped the key into the lock and opened the door and let
myself in, being sure to lock the door behind me. I turned and disarmed the security system
which also confirmed that I did in fact have the house to myself. Dropping my backpack on the floor next to the
door, I made my way upstairs to my room.
Once inside I shed all of my clothing, grabbed a towel, and made my way
to my Mom’s personal shower in her room.
Normally I would have used the other shower that was for my use, and
when my sister was home, her use as well.
This time however I used Mom’s shower because all of her feminine
hygiene products would be there.
Turning on
the shower, I held my hand underneath and adjusted the water until the
temperature was to my liking, normally I would have liked to of taken a nice
bubble bath as I’ve done in the past, but that was time consuming, and today I
didn’t have that sort of time. Hoping
into the shower I took my Mom’s shampoo and squirted some in my hand and began
scrubbing it into my hair, as the scent of fresh apples from the shampoo wafted
in the air. After scrubbing my hair clean
and rinsing out the suds, I reached for the bottle of conditioner and, after
reading the instructions on the bottle, squirted some into my hand and scrubbed
it into my hair. While waiting the
recommended 15 minutes for the conditioner to do its thing, I reached over and
picked up my Mom’s razor and shaving foam, and proceeded to work up a lather of
foam on my legs. I had done this plenty
of times before, so shaving my legs came natural to me even if I was a
guy. A lot of people had questioned me
as to why I did this when they first discovered my hairless legs. Lying to them I told them that the hairs
caused my legs to itch immensely, so I had shaved it all off, but in truth I
had done it to enhance the smooth look of my legs when encased in a pair of
stockings or pantyhose, which would come later.
Once I
finished with my legs, I proceeded to rinse them off as well as rinsing out the
conditioner from my hair. Once that was
finished I reached over for the body wash and proceeded to give my body a good
scrub down, once again, the smell of fresh apples could be smelled in the air,
obviously my Mom liked the smell of fresh apples. Once I was satisfied that my body could not
be any cleaner, I rinsed off under the water and turned it off, stepping out of
the shower I grabbed my towel and began to dry myself off.
Once I was
dry, I made my way back to my Mom’s room and over to her dresser, opening up
the first drawer, I was greeted with the site of a vast selection of different
colours and styles of panties and matching bras. Reaching in selected a black lace bra and the
matching panties, which I laid out on my Mom’s bed. Walking back to her dresser, I opened up the
next drawer and pulled out a black lace garter belt, and a pair of black
stockings, and laid them on the bed with the bra and panties I had already
picked out.
Having
finished with the dresser, I walked over and into Mom’s walk in closet, and
browsing through the racks, I selected a short black mini-skirt, a white
blouse, and a pair of 2 inch heels that I hoped would fit. As I walked out of the closet I noticed a
small box similar to the one I owned pushed back into the corner almost as if
Mom was trying to hide it. With my hands
full I submitted to the fact that I would have to return at a later time to
investigate the box and perhaps its contents.
Walking back over to the bed I picked up the rest of my choices and went
back into my own room and laid the items of clothing I had selected out on the
bed.
Kneeling
down on the floor, I pulled out my own box from beneath my bed and, after
fishing my keys out from the pocket of my jeans that I had left on the floor; I
unlocked the box and removed the contents.
A blonde wig which I had purchased online a few months ago, and a set of
fake breasts which had been my most expensive purchase, and also the one I was
most afraid of being discovered with when it arrived, I had had to order it
under a fake name, and when it arrived, I was fortunate enough to be the one to
receive the package since it surely would have been sent back if anyone else
had been there instead of me.
Once I had
everything I needed in front of me, I proceeded to start to put it all
together. I started by hooking the
garter belt around my waist, lining up the garters properly, then sat down on
my bed and carefully rolled a stocking up each smoothly shaven leg, then
hooking them up to the garter belt and insuring everything was still
straight. Once that was done I spent a
moment to admire the smoothness of my legs, before reaching over to the bed and
picking up the pair of panties and stepping into them one leg at a time and
pulling them up to my waist. I then
picked up the bra, and proceeded to hook it together around my body so that the
hooks were in front at first, I never really understood how women could put
these things on with the hooks at the back, and then spun it around on my body
until the cups were properly positioned on my body. I then picked up the fake breasts one at a
time and slipped them into the cups of the bra before slipping my arms through
the shoulder straps.
Turning to
look in the mirror, I examined my reflection to insure that everything was
properly aligned, and then just for the heck of it, gave my false breasts a
quick squeeze which looked rather funny to me.
Turning back to my bed, I picked up the skirt and held it so that I
could step into it and pull it up around my waist, I noticed that it hung a lot
shorter then I had first realized as it was about half way between my knees and
my waist.. Once that was done I picked
up the blouse and slipped my arms through the short sleeves, and buttoned up
all but the top two buttons, leaving some cleavage exposed.
Turning
back to the mirror I again examined my reflection, it wasn’t bad but I still
needed some work, first I picked up the wig, put it on over my hair, and pinned
it down so that it wouldn’t come loose. The
reflection in the mirror looked good, but it was still missing something. So after slipping on the two inch heals, I
hobbled my way back to my Mom’s room, I had practice on heels, this wasn’t the
first time I had worn them, but I still didn’t have it down perfect just yet.
Once back
in my Mom’s room, I sat down at her make-up table and started to work on my
face. I had nearly perfected this from
watching my Mom and sister doing this, and from trial and error. So a little while later, after some lipstick,
blush, eye shadow and mascara, I was almost done, and after a coat of nail
polish, the job was complete. One day I’ll get a set of fake nails to put on as
well I thought. Looking up from my hands, I examined the reflection in the
mirror which barely resembled my former self.
Instead there was an attractive young blonde staring back at me. I smiled, and she smiled back at me.
Looking at
the clock on my Mom’s bedside table, I noticed that I still had about an hour
until Mom and my sister were expected home.
So I decided to go downstairs to get myself a drink and maybe something
to eat. Once in the kitchen, I opened up
the fridge and pulled myself out a cold coke.
Standing at the back window, staring out into the clouds, I daydreamed
about my future, of what would happen to me if I was ever discovered. It wasn’t until it was to late though that I
realized I wasn’t alone anymore. As I
heard my Mom comes walking in the door, and into the kitchen, where she found
me
“Oh hello
there, I’m sorry I didn’t realize that Jason had a friend over” My mom said,
for a moment not realizing who it was, and reaching her arm out to shake the
hand of what she thought was a friend of her son’s, before pulling it back to
her chest with a gasp.
“OH MY
GOD!” she screamed “JASON?”
I went to
speak but was interrupted by my sister coming into the kitchen to see what was
wrong.
“Mom are
you al…oh my god, Jason is that you?”
I could
only nod my head in embarrassment. For
my life as I knew it was over.
“What are
you doing in Mom’s clothes” my sister asked, I wanted to answer, but I was
still unable to find my voice.
“Go upstairs
to your room Jason, and wait for me there, I need to talk to your sister” My
Mom stated. I could barely walk on the
heels that I was still wearing because my legs were still shaking from being
caught.
“Don’t
bother to change” I heard my Sister add as I made it to the top of the stairs.
When I made
it to my bedroom, I threw myself down on the bed and started to cry, my Mom and
sister probably thought that I was some sort of pervert for doing this. They were probably discussing right now what
sort of help I needed. I wanted to run
but I didn’t know where I’d go. So I
just lay face down on my bed crying into my pillow. I don’t know how long it was, but I must have
fallen asleep, because when I came around my Mom was sitting on the side of my
bed gently stroking my shoulder, and my sister sitting in the chair next to my
computer desk. It took me a minute, but when I remembered what I was wearing, I
broke out into tears again.
I guess now
would be as good a time as ever to tell you about my family. My name, as you’ve probably already figured
out, is Jason, I’m 21, I’m only 5’7” tall, I have sandy blonde hair, brown
eyes, I weigh in at a measly 122lbs, not much muscle on my body, but I’m not
fat either. My sister Cate is 22, a
brunette, with baby blue eyes. She’s
taller then I as well at 5’10” and I know from having borrowed her stuff as
well in the past that her measurements are 32b-24-30. She could almost be Mom’s twin, who even at
the age of 41 still had the looks that turned men’s and women’s heads in
college. The only difference between my
Mom and my Sister was the fact that Mom is a voluptuous 44dd. Mom had always told my sister that her bust
size would increase once she found the right man and had a few kids, to which
my sister would always respond by saying that there could never be a man that
could keep up with her busy lifestyle, which led me to believe that my sister
is a lesbian.
I never
knew my father, but Mom had told me that I wouldn’t want to, she said that he
was a drunken louse and not the romantic gentleman that she fell in love with
in college. My parents met in their
first year of college, both wanting to become Phys Ed teachers, and fell in
love, and after a brief courtship, got married, and had Cate, it wasn’t an easy time for my Mom, she said
she would constantly be spending time with her parents away from our father
because he just refused to do any sort of work around the house unless he knew
that she wasn’t going to do it for him, which was when she left for her parents,
taking Cate with her after she had been born.
He did shape up, for about a year, which is when they had me. It was after I had been born that everything
fell apart at the seems, Dad started drinking again, worse then ever, and when
he lost his job as a teacher at the local elementary school because he had
shown up drunk one day and passed out in the hallway, that Mom divorced
him. But that was 18 years ago and
doesn’t have anything to do with the situation I find myself in now.
Finally
when I had calmed down enough, Mom was the first one to speak to me.
“Jason
honey we need to have a talk” she said.
“Can you
sit up and look at me baby?”
I wanted to
say no, but I knew that I was already beyond the point of no return; I had gone
past that point when I decided to get dressed this way. I sat up anyways though, but was greeted with
the one sound that I didn’t want to hear, a giggle from both my Mom and
Cate. I knew that they thought I looked
stupid dressed up like this, and I knew it as well. Surely they we’re just waiting to lecture me
on not doing this anymore, and even without the lecture, I knew this would be
the last time anyways.
“I’m sorry
baby, it’s just that, you look rather silly with your mascara running down your
face from the crying, come with me, why don’t you come with me and I’ll get you
fixed up.” She said, taking my hand in
hers and standing up next to my bed.
Looking into her eyes, I could see that she wasn’t mad at me, or
disgusted with what I had been caught doing.
I stood up on wobbly knees, and remembering the shoes I had on, sat back
down and removed them, before following my Mom off to her room. She sat me down at the make-up table which I
had been sitting at alone a while earlier, and picking up a small container,
proceeded to wipe down my face. I
noticed in the mirror, that it was removing all the make-up that I had applied.
“You did a
good job on your face surprisingly, but you still need some improvement, so
I’ll show you where you could improve okay hun?” All I could do was nod.
“We’ll use
what we have here for now, but soon I want to take you to a consultant and have
them help pick out some things that would be better suited to your skin type,
but there’s one condition you have to agree to.” Mom stated, her voice getting
a bit more firm then the soothing voice she had been using since my room. Finally I was able to find my voice again and
spoke up for the first time since she had found me like this.
“What
condition Mom?” I asked, afraid of what
the answer might be.
“I’ll
explain, after sending you off to your room, your sister and I sat down at the
table and discussed what we had just discovered, at first I was intent on
coming up here and forcing you to undress in front of me, hopefully
embarrassing you and causing you to never want to do this again, but you owe a
great deal of thanks to your sister, because she talked me out of it saying
that if I did, I would most likely warp your perception of sex, either causing
you to be more private about your sex life, or causing you to think that sex in
general was something wrong, this is a sexual thing for you right hun?”
“Uhuh” I
answered
“Okay then,
there’s nothing wrong with that, so instead of scolding you for this, your
sister suggested that we should support you in this, whether it be just a phase
in your life, or if its something more permanent.” She explained
“Thank you
Mom” I blurted out
“Oh you’re
welcome dear, but don’t forget to thank your sister as well later on, now let
me continue telling you what happened before I forget where I was. After your sister and I agreed on the fact
that we would support you and help you with this part of your life, we began
discussing how we would help you with this.
As you already know, you’re going to see someone who will help you to
pick out some make-up products that will better suit your skin type, also,
since borrowing our clothes all the time just wont due, since your obviously of
a different stature then us, we’re going to take you shopping for some women’s
clothing of your own”
A look of
fear came across my face, one that Mom obviously picked up on.
“Don’t
worry, I wouldn’t send my little girl out into the world without making sure
she looked good. You’ll borrow an outfit
from either your sister or I, and wear that while we are out shopping, and yes
you heard right, from now on when you are dressed like this, you will be
referred to as my daughter, now have you chosen a feminine name for yourself?”
“No Mom, I
haven’t” I said, the small details of picking a girls name for myself never
having crossed my mind.
“Well then,
I guess we’ll just have to decide on one now won’t we?” she said, as more of a
statement then a question.
“How about
the name Jessica, at least then your initials will still be the same”
“Yeah, I
like it” I responded with excitement in my voice.
“Okay then,
from now on, whenever you are dressed up like this, you will be my youngest
daughter Jessica. Now why don’t you look
at yourself in the mirror dear and tell me what you think” Mom said, placing
the brush she had been using on me down on the table.
Looking
over at the mirror, my breath caught in my throat, Mom was right, I did need
some work on my make-up application skills, for the blonde haired girl who I
saw in the mirror, looked nothing like the one I saw when I had done this
myself.
“Well I
don’t know what you two think, but I’ve always wanted a little sister to play
with, and I think she looks absolutely gorgeous” My sister said, she had been standing in the
doorway to my Mom’s room watching us silently until now.
Walking
over to me, my sister reached out her arms and pulled me against her, hugging
me up to her body. I could feel her
breasts mashed in against the false ones I had inside the bra that I was
wearing.
“You look
absolutely wonderful Jessica, and I’m glad to have you as a little sister, and
here I thought that I was the one who would be giving the gifts upon my return
home” she continued, placing a kiss on each side of my face, and playfully
giving the false nipple a tweak.
“Oh, I
think our little girl is getting aroused, feel this Mom, her nipples are hard”
my sister joked, taking Mom’s hand and placing it on my left breast, while her
hand remained on my right. I felt a
smile creep across my face and my Mom and sister openly fondled my breasts.
“God I
never thought I’d be saying this to a daughter of mine, but let us see your
tits Jessica, I want to see how you make them look so real” my Mom said, trying
to hold back a laugh at the same time.
“Um, they
only stay on because of the bra, if I take that off, they go with it” I stated,
informing them of how it all worked.
“Well okay
then, just open your blouse and let us see, you can leave the bra on for now,
but we’ll have to look into a way of keeping them on your body even without a
bra, right Mom” my sister suggested
"Right,
now let’s see how Jessica's tits compare to her older sister's and Mom's" My
Mom said, reaching up and beginning to unbutton the blouse of hers that I was
wearing.
I couldn't
believe what was happening, here I am standing in my Mom's bedroom with her and
my sister, dressed in my Mom's clothes, and she's unbuttoning the my blouse,
slowly revealing the lacy black bra of her's which encased my breasts.
"My
what beautiful breasts you have dear, in fact, I think there almost as big as
your sisters, Cate dear take off your top so I can compare them"
"Mom
are you serious, I can't let Jason see me without my top on” My sister retorted
"Nonsense,
all I see here are three women and not to mention that we're all family!" My Mom stated it was obvious to me that she
was taking this whole Jessica thing serious.
"Oh
all right Mom” My sister said, submitting to Mom's request. It was then that it hit me, I was about to
see my sister in her bra, as she undid the buttons on her blouse, I noticed
that there were no straps over her shoulders where her bra straps would be, I
barely held back a gasp as I began to realize that my sister wasn't wearing a
bra, but was greatly surprised when I saw a lacy white bra that wrapped around
her breasts. I could barely take my eyes
off of my sisters beautiful cleavage, her breasts were firm and without a hint
of sag, even if she was wearing a bra.
"Wow
Cate dear, what a lovely bra, I've never seen one like that before; it looks
absolutely wonderful on you!"
"Thanks
Mom, it’s a strapless bra, I bought it while in
"Its
okay Sis, I hadn't planned this either” I responded, looking up at her or
realizing that she had seen me looking at her chest, but she was smiling.
"Well
then, I think a celebration is in order, so I'm taking my two daughters out to
dinner tonight, so you two put your tops back on, and we'll all go out and get
something to eat" Mom announced
"But
Mom! I cant go out like this, what if
someone I know sees us, they'll certainly know that I'm just male in women's
clothing" I jumped, scared for my
life at being exposed, since I had already 2 people to many in on my little
secret. Mom simply walked over to me,
put her arms on my shoulders, and turned me towards her full length mirror on
the wall.
"Jessica
dear, look in the mirror, what do you see?" She asked
"Me?"
I asked
"I'll
tell you what I see, I see my beautiful young daughter Jessica, now obviously
people who know me know that I only have one daughter, so if anyone that we
know spots us tonight, we'll simply tell them that you are my niece visiting
from out of town, okay?"
"But
what if my friends see me? They'll
certainly recognize me” I responded
"I
highly doubt it, in fact I wouldn't be surprised if you did see any of your
friends and all they did was hit on you."
My sister replied, drawing a giggle from Mom.
"But
if you feel that uncomfortable, we can
simply tell them that you have strep throat and cannot speak, but you'll have
to trust us" Mom put in
"Okay,
if you say so" I responded dejectedly, obviously I wasn't getting out of
this so easily.