Date: Fri, 15 Aug 2014 13:17:25 -0700
From: Victoria VanDersuk <victoriavandersuck@yahoo.com>
Subject: Candy 2 (Transgender Teen)

Candy 2

For the next few weeks I was a pretty happy guy!  I was able to access
silky lingerie and while Mom was clueless Dad knew all about it, and if he
wasn't outright encouraging me he was at the very least supportive.  He
would come into the kitchen in the evening, when he and mommy were watching
their television shows and slide his hand down the back of my shorts or
jeans to see if I was wearing panties.  It seemed like it pleased him so
much to find his boy in panties that I started wearing them every day when
I got home from school until bedtime, when I would change into the nightie
he gave me without mommy knowing about it.  He would lean in close to my
ear and say something like "panty boy" or "my little sissy" or "very nice,
Candy" and then go back to watching TV, I just went to play in my room.

You can probably imagine the way I play in my room, can't you, you naughty
man!

It's hard to describe how I feel when I wear panties or other girly things,
the things are so sensual, so slippery and cool on my skin.  I guess it's
weird to wear them, but why can't boys wear silky underwear too?  It
doesn't seem fair I to be doomed to spending the rest of my life in
scratchy cotton boys and men's underwear, all bulky and sweaty.  Yuck.  The
thing is I know the guys at school wear stuff like that, and I guess it's
all right for them, they don't think of feeling sexy like I do.  I like
panties...and other girly stuff too, actually, the girlier the better!

The experience I had with Daddy with the vibrator from mommy's dresser
drawer kept popping up in my head, and I found that not only was I plunging
that buzzing white vibrator into my butt more and more, like every day, but
I was also sticking other things up there.  As usual these butt packing
events happened after school, but a few times he caught me in my room with
a candle or a cucumber from the crisper in the refrigerator.  The cucumber
incident was particularly embarrassing, especially because he seemed so
shocked and after pushing it in and out of me telling me how naughty I was
while I creamed out another load of juice, the cucumber appeared on our
dining table the next day, sliced and in a cream sauce in a pretty floral
dish.  When mommy put it on the table we looked each other in the eye and
both started to giggle.  Mommy didn't understand, she never understood the
relationship between me and Daddy, and feeling somewhat left out she began
to drink a little more each and every day.  Mommy liked her wine, and while
in the past Daddy rationed her glasses of wine, lately he has encouraged
her to drink and then go to bed early, and she typically passes out
watching the Real Housewives from bed.  Her favorites are the housewives
from Beverly Hills but she also likes the crazy screaming and fighting
Italian housewives from New Jersey.  I don't get it.

At the time of the evening I am usually finishing homework and preparing
for bed and since Mommy is on her way to wine induced dreamland it gives
Daddy the opportunity for what he calls "Daddy time" with me, and I love
the attention.  He has always been such a loving father, and he has taught
me so many things...like how perfectly normal it is for a boy to like
slippery cylindrical objects repeatedly thrust into our tight bottoms, the
magic of the prostrate button, and how a boy needs to cum as much as
possible so his system doesn't get backed up.  He also told me that men,
even daddies, need regular release too.

Daddy really respects a boy's need for privacy, he bought me a locking
footlocker to place next to my bed.  He told Mommy that all boys need a
private place for their things out of the snooping eyes of females.  Mommy
just rolled her eyes and poured another glass of cheap merlot.  The
footlocker is made of baby blue metal with aluminum accents, and has a
combination lock.  Daddy set it up for me and gave me the combination but
told me not to share it with anyone else including Mommy.  As soon as I got
it I put the clothing inside that I had been trying to hide from my mother,
the pretty nightie and the pairs of stained panties I had accumulated.  It
was such a relief to feel secure and share this secret with Daddy, who
loves and understands me.

Every few days since he gave it to me I have opened the locker to find new
things he has placed inside of it for me.  One day it was a tube of KY
jelly, another day there was a tube of lipstick. That was something I
didn't expect, the color was bubble gum, and it felt really neat to paint
my lips with it and I enjoyed wearing it when modeling a corset or pretty
outfit, it made me feel so girly!  I even kissed the bathroom mirror a few
times real sexy like and it was fun.  It really surprised me when I opened
the locker to get out a pair of panties so I could jerk off and I found a
magazine inside called "Daddy's girl" with naughty pictures of a boy in
lingerie being fucked in the bottom by Daddy's big hairy cock.  I shook a
little when looking at the pictures, the boy in pictures looked very pretty
the way he was dressed, in a corset and stockings, along with big flouncy
petticoats and a pink little girls dress.  I was fascinated by how cute the
boy looked, he had makeup on, a blonde wig, rosy cheeks and red lips and
even colored powder above his eyelids!  I noticed how happy the Daddy was
in the pictures fucking his little boy.  Oh, I am sure they were not really
father and son of course, right?  There were also pictures of the boy's
lipsticked lips wrapped around the Daddy cock, and the boy's eyes were big
and bright and full of love and devotion as he serviced him.  I knew about
blowjobs from what the boys on the bus said all the time, bragging how they
loved getting blown.  I must admit it made me wonder what it would feel
like to have a cock in my mouth, I was already getting used to eating cum
since Daddy had ordered me to start eating my own to cut down on the mess
in my room.  I'm always getting hassled about what a mess my room is, but I
know where everything is, and it's my room, isn't it?

At first I thought it was weird to eat cum but then I realized I liked the
taste so it wasn't too bad, and I began to eagerly catch as much of it as I
could in my palm when I came.  Daddy also taught me to cum while stroking
and looking at myself in the mirror, and I liked that almost as much as
humping my little pillow!

I never mentioned finding the magazine in my footlocker, I just didn't
acknowledge it, and Daddy never spoke of it, but I looked at it like every
day and every day it made my little cock hard.  I started to wonder if all
cum tasted the same, like what did Daddy's taste like, or my best friend
Justin's juices.

My birthday was just a few days ago, and it was pretty awesome!  As it
turned out I kind of had two birthdays, the first one with my folks and my
uncle and cousins, and I got some pretty cool stuff, some games and a few
gift cards.  The second birthday I didn't expect and came after the party
was over and everybody went home, Mommy had her fill of partying and wine
and merlot and had passed out in my parent's bedroom.  During the party
Daddy seemed kind of nervous and I kept catching him looking at me funny.
I figured he was trying to figure out what kind of underpants I was wearing
so when he looked once I pulled down the waist of my shorts a little bit so
he could see the elastic waist of a pair of pink panties.  Hey, it was my
birthday, and I wanted to do what I want, and I have grown so accustomed to
how awesome nylon tricot felt against my skin.  It just made my butt and my
cock and my balls feel so good to be surrounded by that sexy material.
When Daddy saw I swear he blushed and turned away.  I was very careful as I
hung around my cousins that no one saw my panties.  My cousin Bart would
love to get something on me, he's a little older and always picked on me,
and his two sisters were both pretty girly girls.  I couldn't help but
notice the pretty petticoats and panties under their dresses. I just seem
to have more fun with the girls, and Bart gives me dirty looks.  I don't
like to be alone with him because he can be kind of mean.  He even called
me a sissy a few years ago when he caught me hanging around with his
sisters while they were playing barbies, but we all yelled at him and he
went away.

So after they all left and we were alone Daddy told me that he had some
special presents for me, just between us.  I was intrigued as he pulled out
a shopping bag with three or four decorated packages.  I got kind of
excited when I saw that the packages were all wrapped in pink floral paper,
girl's paper, with bright pink bows on the top.  Each package had a white
gift tag on it, and in Daddy's handwriting they were for "Candy" which made
me blush.  The deviant side of me was really excited I guess, because I
went over to Daddy on the couch and sat on his lap, like I used to do when
I was littler.  He was beaming, and told me that I was very special to him,
and that he knew what made me happy.  I just shook my head and leaned in on
his strong shoulder as he caressed my leg.  It sure is cool when a boy can
count on his Dad to be there for him!

I hurried to open the first package he gave me, it looked like a clothes
box, and that was what was inside it, but not what a Dad would give his
son.  Instead of a football jersey or a pair of cool board shorts there was
a corset, in the prettiest shade of pale blue, with several pairs of
stockings and the tiniest pair of matching panties but they looked pretty
skimpy.

"It's from our new Teen Princess line, Baby.  Do you like it?  The lingerie
companies are marketing to younger and younger girls these days since
everyone is growing up so much quicker.  Girls spend small fortunes on
dates, especially special days like prom or quinceanera.  This garment is
made of the finest silk in their blue skies color with tapestry embossed
accents of teal and black on the garter straps and lacing, oh and the
pretty black lace around the bustline.  The matching stockings are black,
and the panties are really something...crotchless!  My but the girls are a
lot racier than when I was a young man!  Imagine the excitement of
presenting yourself to your young man in such a beautiful outfit!  It's a
different world isn't it, with gay boys and the transgendereds and god
knows what all?"

"Umm, yeah I guess so Daddy", wondering what I was.

I blushed as my fingers held the corset and I felt the fabric.  I was
excited, aroused, hell I couldn't wait to try this thing on...and unlike
the things I found in Mommy's drawers this corset seemed to be my size.  I
knew he was watching me, and not sure what he expected of me I decided a
mild protestation of some sort on this assault on my masculinity must be
expressed.

"Umm Daddy it's really pretty, but it's um so...feminine!"

"Well honey of course it is!  It's for a Teen Princess after all.  I did
buy it for you in blue... you should have seen the baby pink one!  Pink is
for girls and blue is for boys, isn't that the way things work?"

My hands were shaking as I thought about wearing this thing, about the
strings being pulled tighter and tighter on my frame, about what it would
do to my figure and how it would feel to have my stomach pulled in and the
flesh pushed around in a feminine shape.  Daddy must have sensed I was
zoning out a bit and gently took the corset from my shaking hands.

"Here sweetie, open another present and Daddy will hold onto your pretty
lingerie for you.  It's so nice to have you on my lap again, you weigh a
lot more now but Daddy doesn't mind, after all he's a big strong man."

He handed me the second package and I opened it.  I had guessed from the
shape and size of the package it was shoes, and sure enough there was a
pair inside.

Heels!  Black heels!

"Daddy why do I need these?"

"Well you can't be walking around here in those dirty old sneakers of yours
while you're having your girly time.  I don't want anyone saying I can't
afford to properly clothe and shoe my offspring, remember I am in the
garment business, I have a reputation to uphold! "

Well, that was true.  Dad had joined the lingerie company about three years
ago, it was a career shift for him, and afterwards he always noted what we
were wearing, whether or not it was a quality garment, and we were told to
give clothes away to charity at the first sign of wear.  Of course the
lingerie samples were off limits as they were special.  They sure make me
feel special!

Dad's hand was on the inside of my leg, boyishly smooth, and he gently
stroked it as my fingers caressed the shiny black leather, tracing over the
pointy spike of the heel.  As I examined my new shoes I wondered how on
earth I could walk in them!  Daddy shifted, forcing me even further down on
his lap.

I guess he was right about grown men having boners too, because I could
feel his poking at my bottom!

"Sorry sweetie had to shift for a minute.  Say what do you say you put on a
fashion show for me?  Let's see if your old man guessed your sizes
correctly.  You know women's sizes and men's are not the same, it takes a
professional like me to properly fit a foundation garment, let alone a
shoe!  Women's shoe sizes are impossible!"

Daddy was so wise, and well I really did want to try these things on, I had
a boner of my own!  I hopped off his lap and pulled the navy blue t shirt
over my head and hurriedly undid my board shorts and let them fall to the
ground.  I was reminded of my panties when I heard Daddy gasp at the sight
of them...they were from one of his collections...pale pink and fairly
sheer, sheer enough to show my equipment.  They were already stained with
my jizz and I had moved them to my private collection a few weeks ago.

"My but those are pretty panties!  I thought I recognized them earlier when
you so naughtily made sure I would notice them!  Aren't those the panties I
gave her for her birthday last year?  I so wanted your mother to model them
for me, but I must say you look adorable in them.  Did you know there is a
matching brassiere to those panties?  What am I talking about? I remember
your eyes were bugging out of your head as she opened the package and held
them up in front of us!  Such a shame all the beautiful lingerie I have
bought her through the years, and I've only gotten to see her in it once in
a while, like on my birthday, or when I bought her the Buick!  I'm so glad
this is something we can share together and you appreciate the finer
things.  No cotton panties for my boy, that's for sure!"

"Well Dad I really want to wear this stuff, I like the way it feels... all
funny and tingly inside and I just feel awesome.  Are you sure this is OK,
I mean I am a boy and all."

"Well let's not get tied into labels... boys, girls, straight, gay, men,
sissies...let's just have fun and do what feels right.  Now strip off those
clothes and into your pretty corset.  You know the blue matches your eyes
Baby, and the black accents make it look so sophisticated!  We've sold a
whole bunch of these!"

I had to admit it was awfully pretty!

I saw Daddy rubbing his pants as I casually let my panties drop to the
floor and stepped out of them. I blushed and started to pull the garter
belt up my naked body.  It was a little tight, and Daddy had me come close
and turn around so he could adjust the straps that crisscrossed the back of
the corset.  He loosened it here and there, pulling and straightening it,
and when I was properly in it he told me to hold my breath and he pulled
tight on the laces."

"Daddy!"  Whew, I can't breathe!"

"Nonsense, every girl thinks that!  You want to be pretty, don't you?  Let
the corset give you a nice girly shape!  Beauty is hard work, isn't that
what your mother says?"

We laughed as he pulled my straps tight and then made a big bow in the
back.  I reached down and felt how the boning in the garment pulled in my
waist and redistributed body mass up to my breasts and down to my hips.
Daddy had me sit back on my lap.  It was kind of embarrassing because my
cock was pretty hard and bouncing around, it was like 4 inches of needy
pink flesh.  He taught me how to roll up stockings like a lady and helped
me attach the garters to the top of the stockings.

The feeling of that sheer nylon on my legs was such a turn on, I felt
so...so...girlish.  I guess that was it.

"Now son the panties, I know there's not much to them, but then that's what
you need so your little clit is able to be exposed and thrusting when you
masturbate.  Men call these crotchless panties so they can get at a girl's
pussy.  Say a man wanted to eat your boy pussy, now he doesn't have to wait
until you remove your panties for him, he can be spontaneous and you can
submit to his needs and present your hole to him."

Present my hole to him?  Weird.

I've heard the boys talking about pussy eating but I thought it was a joke,
does anyone really do that?  And besides my pussy was really my ass, would
a boy really want to put his mouth on that?

I sat down and couldn't bend over to try on my new shoes, the corset was so
tight!  I asked daddy for help and he was eager to help me into the heels.
They looked so cool, the heel was high and there was a thin black strap
around the ankle which made me feel like I was trapped in them or
something!  Daddy said they needed to be tight so I had proper ankle
support.

It was an incredible experience, wearing this outfit, knowing it was mine,
intentionally for me.  The corset was tight and I loved the feel of the
garter straps that went from the corset to the top of my stockings, which
felt totally awesome!  The black crotchless panties were mostly lace, and
the harshness of it felt weird around my crotch, I was completely exposed
and getting super horny!

"Now Honey I have one more present for you.  You look so sweet and cute, do
you know that?  I always wanted a daughter and now I have one, at least
some of the time.  Will you be Daddy's girl?"

"Umm sure Dad, I guess so."

I couldn't let him know how much I was enjoying this, could i?

"Good girl!  Now here's your last present."

I stood before him in the pretty corset and stockings, the crotchless
panties allowing my painfully hard little cock to stick out obscenely,
wobbling on the heels and not daring to move.  He handed me another gift to
open and I opened it quickly, terribly excited.

There was a lot of chartreuse colored tissue paper and I reached my hand
into the box and jumped!  What the...?"

"It's a dildo of your very own, and a tube of lubricant.  Isn't it nice!
It can't be a birthday without giving my boy a toy, would it?"

I shakily held the flesh colored rubber dildo in my hands, it was thick and
veiny, about 7 inches long.  It was much fatter than the white plastic
vibrator that I had been using to pleasure my hole.

"Isn't it pretty?  I ordered it special for you, if you're going to fuck
your boypussy it should be a quality sexual appliance.  This one is a
sensafirm and I carefully selected it to match my own penis. "

I shook a little as I held the lifelike dildo, feeling the veins protruding
on the underside, and the big head of it.  I had been putting a plastic
vibrator inside me, also a cucumber and whatever else I could find around
the house.  But this was different, this was shaped like a cock, it was
flesh colored and knowing it matched my Daddy's cock made it extra weird!

"Gee Dad, thanks...it's awfully big.  Are you sure it will go in me?"

I shuddered at the thought of what it would feel like.  The thickness of
it, the thick veins on the underside of the shaft and that big mushroom
head...whew!  I bet it would hurt!

"Well sure it's big, son, we've got to train that hole of yours if it's to
be of any use!  Now you get down on all fours there on the carpeting and
Daddy will help to demonstrate it.  You know how important it is to provide
a product demonstration to the skeptical consumer.""

I carefully got into position, truthfully glad to be off those heels and on
my hands and knees, my little cock all stiff and pointy, and waited as I
felt Daddy fidget behind me.  I hear Daddy dig around in the crinkly tissue
paper, didn't he say something about lubricant?  shuddered at the feeling
of cool gel on my butt hole, and when I felt first one, then two fingers
diddling my hole to prepare me.  It felt nice and I spread my legs further
to invite him in.  My little cock was incredibly hard from and thrusting
into the air, nothing to touch it to relieve the pressure inside.

"Always remember to use plenty of lubrication when inserting this quality
latex instrument.  You already know how to take a cock in there, err I mean
a vibrator...so push out a little and prepare yourself as I insert it
inside you.  Try not to make a mess honey and blow your load, hold it until
I tell you.  I know you can do it."

I sighed and pushed out as Daddy's fingers escaped my hole.  I know this
was obscene, so totally out of the norm for a father and son talk, but I
wanted to feel what it would be like to have that new toy inside me.  Could
I take it?  I squirmed as I felt the big mushroom head of it poke at me and
with persistent prodding and poking Daddy pushed the head inside me!

Fuck, did it hurt!  Oh shit, did I say fuck?  I am not supposed to swear!

"Oh Daddy!  It's so big!  Stop for a minute!"

"You bet it's big!  That's what your mother used to say until I broke her
in.  Now just relax for a minute and let your hole accept the cock and push
back on your hole on the count of three!"

I took a deep breath, and tried to use my ass muscles to flex my hole, and
push outward.

"One...Two...Three!"

I squealed in pain as I swear another three inches of my new birthday toy
penetrated me!  I felt so incredibly full, so full in fact that my cock
went a little soft I was focusing on it so much.  But then I felt it start
to go in and out, in and out, and it became easier and I couldn't help
myself I was moaning and squirming, trying to get more of it in me.

"That's it princess!  Let yourself go and cry out if you need to, your mom
is out cold.  I want to make sure you experience the features of this
finely crafted instrument of pleasure.  Any boy can stick a banana or a
cucumber in his butt...well, not most boys I guess but you always were very
creative!  I guess what I'm saying is son you have special talents, so use
them, let them grow.  You have an amazing pussy hole son, it's so small and
pink and hairless.  You know you work on those pussy muscles of yours and
you'll really have something there!"

It sounded like Daddy was proud of me, and I felt warm and happy.  The pain
in my butt wasn't bad at all at that point, my dad sure knew how to work a
dildo! Whew!

"Yes Sir, you were always a boy with potential!"

Daddy started pulling the dildo out of me and then reinserting it, going
all the way in and then almost all the way out with each thrust.  I grunted
and moaned with each thrust and must admit I did squeal a little bit when
it went especially deep.  I was loving how wonderfully this new toy made me
feel!

"You have such a pretty little boypussy son, it's so smooth and pink!  We
won't let any hair grow back there will we?  That won't look pretty at all,
will it?  No sir, my Candy is going to remain nice and smooth back there,
just like he is now.  I must tell you honey that your pussy looks awfully
pretty as it swallows up that cock."

I was just mumbling and moaning at this point, focusing on the way he
plunged it in and out of me, and then pulled out for a minute.  I heard
something... was it a zipper or something?  Anyway, after a minute I felt
the dildo pushing into me again, this time it just felt different, the
pressure felt different from his hand manipulating a dildo.  I pulled my
head from the pillow and looked back to see Daddy with a smile on his face
and he was holding my hips, as my hole continued to swallow up the
hardness.

"Just close your eyes and think about spreading your hole baby, and take
what you are getting, that's what girls do, they endure. "

I felt the pressure pick up, what was inside me was thrusting harder and
harder and it seemed incredibly hot.  Daddy was starting to moan as the
thrusting became more frantic.

"Daddy please, my hole is getting sore, and my cock isn't hard at all now,
all I can feel is pain."

"Just a minute or two now, and then we will be all done.  Your boy pussy
feels really nice Candy.  Don't be a selfish girl now honey, think how good
it feels to bring someone else pleasure.  You can't always think of
yourself"

"Daddy's girl, Daddy's sissy girl.."

"Almost there...almost there..."

Did I know my own father was fucking my young ass with his real cock, and
not the fake one?  I don't know I suppose I did, but the need inside me for
penetration was so overwhelming I just didn't care.  It felt good, I felt
girlish and submissive, I felt like myself.  I learned something about
myself that day, the craving was confirmed, the need to be penetrated and
submissive.

With a great shove I felt fuller than I ever had and then I felt the thing
in me pulsing and shooting inside me, it was such a weird feeling.  Daddy
groaned loudly and I felt him shaking behind me.  I was barely breathing I
was so excited.

The dick in my bottom slid out of me and I got up off my hands, but I was
still on my knees.  I was shaky and fell back into my dad's arms as he was
still behind me.  I felt secure in his arms and felt my little cock getting
hard.  Daddy noticed it and used his own hand to masturbate me, and with
his left hand he pinched my left nipple a bit.  He jerked off my cock while
he whispered things in my ear...telling me how pretty I was, and how
special I was to him.  It felt so good to have another person's hand on my
penis, and i barely had time to get my own hand into position so I could
catch my cum in my hand, well most of it anyway, and not leave semen stains
all over the carpeting.  Mommy is a stickler at having a clean carpet, you
should see her with her Electrolux!

It was a birthday to remember!  I kissed Daddy on the cheek and thanked
him.

"It was the best birthday ever, Daddy!  Thank you for my new clothes, and
the shoes, and of course my new toy."

"Son, it was my pleasure!"