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Last winter I moved
back in with my parents after a bitter divorce and losing
my job. My stepfather and sister were not all that pleased
with the situation but I had little choice and little
money. For the first few weeks I regularly went out job
hunting but as the results were a constant stream of no's
and the weather grew inclement I began to stay home.
Wandering around the place where I had grown up brought
back floods of memories, behaviors and feelings.
Recollections of the fantasies that I had designed
resurfaced and daydreams wandered daintily along
suppressed ways. The finished basement where I was living
also stored all the old family belongings. One day, having
received two rejections on early job interviews, I began
to browse through the boxes in the basement. The pain of
having been turned down brought back the memories of the
times I had been rejected in high school. Back then my
solace was to change reality and to become someone whom
everyone desired to be around. Shaking with excitement I
stripped down and began to decide what I was going to
wear. The lime green French cut panties went on first and
within moments I was fully excited. I began to ooze and
knew that unless I addressed this quickly there would be a
mess. With rapid strokes I climaxed and then wiped myself
clean, every so often squeezing out a lingering droplet
until I was flaccid again. This time I slipped myself
between my legs and snuggled into the panties. White
opaque pantyhose rolled down and onto my slender legs. The
tight material wrapping around my calves and thighs,
further hiding and securing me. A white bra with lace
scallops along the tops of the cups gathered in my meager
chest but gave me no cleavage. Two rolled up panties
fitted into the cups gave the illusion of a bust line.
This was enhanced when I pulled on a clingy black jersey
top. The cool fabric molded itself around my bust and
waist. The sleeves did little to hide my thin arms though
the open neckline gave a hint of Cleavage. Next I shook
out the black sateen hot pants before drawing them over my
legs and around my hips. Compact and smooth the zipper hid
any lingering trace of who I was and showed instead who I
dreamed of being. Finally I sat on the edge of the bed and
unzipped the side of the boots. The vinyl crinkled as I
pointed my toe and arched my foot inside. Delightfully
tight the boot painted itself over my foot. The long
zipper pulled the vinyl to my leg and quickly I stepped
into the other boot. As I stood and swayed for an instant
over come by the sensation I felt the exquisite tension
inside my hot pants. Looking down at my long booted legs I
wanted to see how good I looked but the only full-length
mirror was in the upstairs bathroom. A quick look at the
alarm clock told me that I had plenty of time before
anyone came home from work. So I strutted upstairs and
posed for myself in the mirror. From the neck down the
illusion was passable but as I looked at my face I felt
let down. So I went into my sister's bedroom and found a
chintzy blue-black pageboy wig. The cap was so cheap that
it took forever to get the wig to stay in place. The face
in the small mirror as closer to fitting the clothes on my
body. Then I began to dabble with her make-up. Blush,
mascara, eye shadow and liner and lip gloss. My face
looked uneven but that did not stop me from going back
into the bathroom. Again I posed and smiled and felt
myself ready to burst through the sateen hot pants. The
last time I'd done this I had fantasized that Mike who
lived down the block would find me dressed like this and
that we would make out and he would treat me like a real
girl. I gave one last look at myself and started down the
stairs to relieve myself. At the bottom of the steps as I
turned to go into the basement the front door opened. Cold
air swept in with my stepfather. For a long instant he
simply stood there as if trying to recognize who was
standing in the hallway. With no place to hide I merely
stood there and waited for the reprimand. Slowly and
silently he closed the door. "Don't move," he
said softly and shuffled into the living room. His anger
trailed him. A moment later I heard a muffled voice and
then the phone being replaced. Shaking with fear and
anxiety I remained in place for long minutes.
Then the
doorbell rang. My fear escalated and my heart was about to
rip through my blouse and I felt sweat trickle down my
back to the top of my pantyhose. What was my stepfather
doing? I wondered as he stepped into the hallway and
pulled open the door. Marie, our next door neighbor,
entered. She looked from my stepfather to me a small smile
growing with every second. "I came home so that we
could be together and this is in the hall," my
stepfather spoke quietly as he closed the front door. In
shock I was still standing where my stepfather had found
me. "You've got to admit he's got a cute
figure." Marie took a few steps forward. "I'd
kill for legs like that." She stopped a few feet
away. "Turn around honey." In mute response I
swiveled on the balls of my feet. "Look at those
cheeks Tom. Round and firm." Suddenly I felt a hand
caressing the curve of my right buttock. I shuddered. Hot
breathe blew over the back of my neck. My eyes shut in
ecstasy. The hand sweetly kneaded my flesh drawing ever
closer to the center. Another hand was on my waist, along
the belt of my hot pants, beginning to dive lower and
lower. Slowly my flesh began to melt. I twisted my neck to
meet the source of that now panting breath. Glossed lips
found damp hungry lips. Tongues entwined. Fingers began to
push up the center of my rear. Hand circled my zipper.
Beneath that hand I felt a tortured need for release. Then
the hands moved and rested on my shoulders. Turning me
around and forcing me down to my knees. The white vinyl
boots creaked as I knelt. Opening my eyes, I looked up.
Aflame with lust and desire my stepfather began to
unbuckle his pants. The moments of pleasure turned to fear
and loathing. What was I doing? What were we doing? The
sound of the zipper crashed through the hall. From under
his white boxer shorts my stepfather pulled out his
pulsating member. I tried to back away. Hands on my
shoulders prevented me from moving. "Relax
honey" Marie whispered from behind me. "Just
think of it as a big lollipop." My head still tried
to retreat but my stepfather's hand grabbed me and brought
me head to head. Salty ooze touched my lips. Heat radiated
from the pointed flesh. Marie pinched my arm and my mouth
opened. My stepfather pushed his in and began to rock back
and forth. Gagging I fought to find my breath. Panic
flooded me until my nostrils flared with breathe. As I
started to breathe I was able to control my gagging. By
now I could sense that my stepfather was ready to explode.
With one last long thrust my stepfather plunged into the
back of my throat. The explosion gagged me again. This
time I was forced to swallow. As quickly as it had begun
the act was over. "You're a quick learner,
honey." Marie was lifting me off the floor. My
stepfather turned away as he pulled himself together.
"You'll do fine at tonight's party." I looked at
her in the eye for the first time, she was smiling broadly
now. "What party? What are you talking about?"
My stepfather walked back into the living room. "Tom,
your Dad thought since you like dressing as a girl he'd
have a little coming out party for you." She placed
an arm around me and began to walk me to front door as she
talked. "I've got this sweet little red leather dress
that you'd look hot in. Not that you don't look good now,
though you need to work on your make-up. But I can do that
for you tonight." As she went on she'd opened the
front door and directed me outside. Panic erupted. I
couldn't go out like this, someone would recognize me.
Someone would know that I was a man! Yet Marie rattled on
about foundation and winter colors as we walked over to
her house. The cold air slipped over and passed my booted
legs and sent a chill through my jersey blouse. Boot heels
sounded on the sidewalk and then we were inside where I
felt a sense of calm. That calm lasted only for few
minutes when I heard Marie mention who was going to be at
this party. Mike!
The first thing Marie had me do was strip down. My shamed
resistance was laughed away as Marie took me by the hand
into her bedroom. "Honey, you've got to relax, enjoy
yourself." She pulled up my hand and turning the palm
upward she softly kissed my hand, her tongue lightly
running the length of my middle finger. With a hungry look
in eyes she dropped my hand and took off her top, her firm
breasts erect and taunt. She smiled and slid a hand into
her waistband, "You want to see more you'll have to
match me piece for piece." Quickly I drew the jersey
blouse over my head, the wig coming loose and falling to
the floor with the blouse. Marie smiled and wiggled out of
her jeans, and I tugged away at the sateen hot pants. She
kicked off her loafers and I sat on the bed to tug away at
the vinyl boots. As I struggled Marie stepped over one leg
and pulled away the boot and then she straddled my other
leg and pulled off the other one. But instead of moving
away she back her full rear into my face. Clad in royal
blue silk panties her cheeks poked into my nose. Her scent
was intoxicating, rapturous me as my hands held her wide
hips. She switched her rear a few times as my tongue
flashed out. Then she in one quick movement she stripped
off her panties and turned to face me her knees near my
ears. When I moved to remove my panties, she leaned
forward, her hands on my shoulders forcing me down onto
the bed. Oozing she lowered herself over my face and I
breathed in the musty aroma. Then her soft, quivering lips
were on mine and like a drowning man I lapped away at her.
Time seemed to stop as my tongue moved and circled and
darted around and around and around. From far away I could
hear gentle moans and then Marie was grinding her hips
into my face as I desperately tried to match her tempo.
With a last powerful thrust Marie nestled herself onto my
face. The dark black hair tickling in the inside of my
nose. For a long while we remained that way until Marie
finally rolled away. "Honey, you have one mighty
tongue. Where did you learn to do that?" I blushed as
I recalled the first time I'd done something similar.
"From my wife," I replied softly. Marie's hand
brushed at my face. "Is that where you learned to
dress up too?" My face went even redder.
"No," my voice seemed to be stuck in my throat.
"I use to do that when I was just a teenager."
"Well, Honey." Marie paused for a minute.
"I can't keep calling you that, do you have a name
for yourself?" She sat up on the bed and I followed
suit. "Kerry," I said in as feminine a way as I
could and Marie smiled. "I always liked the way
Keri-lotion felt, soft, smooth, sensual."
"That's something we can make you into." She
stood up and pointed to my bra and pantyhose. "Get
rid of those and join me in the bathroom. We've got some
work to do, Kerry." She left the room and I was alone
for the first time in what seemed like a lifetime but was
really only a little over a hour. There were a thousand
different feelings racing through me as I tried to adjust
to the changes that
were rapidly occurring. Most of all I was amazed at how
natural, though a little scary, this experience felt to
me. As I began to undo my bra and then strip down my
pantyhose, the same way I had seen my wife undress, I
began to feel more feminine. Standing up I looked down at
my body and frowned at the thin roll of flesh around my
navel. If I wanted to look really good I would have to
begin to exercise much more I told myself as I went into
Marie's bathroom. Hot steam wafted from the shower stall
and Marie's bare arm waved me into the streaming jet of
water. She lathered my body and toyfully pulled at my
withered member, cupping her hand around my plum-sized
testicles. Marie said nothing as the sweat and dirty were
washed away. Then she stepped out of the shower and pulled
me with her, handing me a big fluffy terry-cloth towel.
"Just pat yourself dry," she instructed me,
"And sit on the throne." From her vanity she
produced a can of shaving cream, a pink razor and small
pair of scissors. "Just sit still," was all
Marie said as she began to first trim the dark hair from
my legs and under my arms, then to lather my body and with
short strokes to shave me from neck to toe. She used two
different blades and she must have used the entire can of
shaving cream before she finally told me to go back into
the shower where I rinsed away cream and hair. When I
stepped out again my body looked very different and much
more feminine. Marie handed me a bottle of Jasmine-Scented
Body Lotion and left. As I started to apply the soft gel I
could feel how smooth and delicate my skin now felt.
Rubbing in the lotion with the scent tickling my nose and
the sense of achieving a level of femininity I had never
reached before, I felt a twinge of excitement and began to
stiffen. When Marie came back she saw what was occurring,
with a wry smile she said, "That would distract
everyone. Let's take care of this for now." She
dropped a tiny bundle and plopped a blob of Body Lotion
into her hand and reached for me. She handed me a pair of
panties. I held it out to see which side was the front and
then placed my feet inside the legs. The cool material
swiftly warmed to match my skin as it slid on. Marie had
me turn around and encased my torso in a red and black
satin corset with six suspenders. The hard fabric
constrained my ribs as Marie tightened the laces. The roll
of flesh I had seen disappeared and the little flesh
around my breast formed the illusion of cleavage. The
suspenders slapped against my legs as Marie had me take a
deep breath and pulled on the laces. After I exhaled I
found that I could not breathe as deeply as before. Taking
my hand, Marie turned me and took me back into her bedroom
where she had me sit on the bed. A pair of black silk
seamed stockings lay beside me. "Try to get the seams
straight," Marie, asked as she went into her closet.
I rolled down one stocking and pointed my foot into it.
Silk slithered up my now bare leg, the sheer material and
hairless flesh sending a surge of lust into my cocooned
member. Struggling to keep the seam in line I tussled with
the garter snaps but soon had all three secured and then
did my other leg. Finished with the garters I ran my hands
over my legs, turning my calves and looking at the line of
my leg wallowing in the sensation. Marie was smiling at me
from the closet. She was holding a red leather dress in
her arms. "Kerry, your legs are going to get you
anything you want. And with this," she extended the
dress, "You'll look hot." Unzipping the back she
motioned for me to stand and as I did I felt the blood
rush away from my head. Swaying for an instant I panicked
when I realized I was not breathing the way I was used to.
Marie's hand steady my arm and I found a new pattern to my
breathing. She directed my arm upwards and like a child
she slid the dress over my arms, head and shoulders. My
somewhat large hands popped through the sleeves as my head
emerged. Marie tugged the leather down over my corset,
behind and thighs. She zipped me in and the leather fitted
itself to me. The butter soft fabric caressing my bare
shoulders and held my thighs tightly. I thought that with
every tiny breath that I took that the leather would
explode. Instead the dressed warmed to my excitement and
enhanced my body. "Now," Marie placed her hands
on my shoulders and steered me to her bedroom's vanity.
Seated, Marie turned the chair so that I was facing her.
She frowned, "That wig you had was awful and would
ruin the look. We'll have to do something with what you
have." My chestnut brown hair was fairly short and
Marie stared at my head for about five minutes before she
took brush and comb in hand. Her hand then flew over my
head as she fought to find the look she sought until she
finally grabbed a scissors. Before I could say no, Marie
had started to cut. The snip of the sharp steel echoed in
the room and in my ears when suddenly it stopped. Now
Marie took some gel and combed out my hair. As she stepped
back to look at the effect, I went to turn to face the
mirror. But Marie prevented me, "When we're done you
can look. Not before." "First things
first." Marie took up my hands and cleaned my nails
and with an emery board gave them a more delicate shape.
Then she applied ice pink nail polish on each finger.
"Let those dry for now," she said as she took up
a handful of brushes and crafted my face. I closed my eyes
and relished the scent of foundation, blush, shadow and
gloss. A sharp pain above my eye caused me to open my eyes
and look at Marie who had a tweezers in her hand.
"Your eyebrows are little too thick. I'm just going
to thin a bit." For long minutes Marie plucked me and
the pleasure of the surcease of the act was marvelous.
Then I was turned around and from right behind my ear
Marie whispered, "Take a look at the new Kerry."
The face in the mirror was mine, but I looked the way I
had never been able to acquire on my own. Satiny honey
brown eye shadow and long black mascarered lashes brought
attention to my shining brown eyes. Rosy pink blush
created a hollow and defined my cheekbones, while velvety
pink lips quivered with joy. My hair was cut to pointy
ends around my ears and short bangs dangled onto my
forehead, with swirls of hair around my long neck. The
face in the mirror was me, and I was Kerry. "Just
some last touches." Marie's voice was now across the
room. I turned again to face her with tears behind my
eyes. "I think that with your legs, these will look
great." She held up a pair of black patent leather
spike heeled ankle boots with a tiny silver strap across
the instep. Still sitting I took them from her and pointed
my stocking foot inside. Silk and satiny liner allowed my
foot to glide into the boot that formed itself around my
toes. With the second boot on I turned and twisted and
admired my legs, Marie was right about them.
"Here," Marie slapped playfully at my legs.
"Stop looking at yourself and put these on." Her
hand deposited a tangle of silver and I placed three
bracelets over my wrist and two plain rings on my left
pinkie and right index finger. Marie was spraying me with
Charlie as I looked down at my hands. Just then the front
doorbell rang and I remembered what this was all about.
There was going to be a party and I was going to be the
star. Marie smiled at me, "You look more like a woman
than most women. And those legs!" She tossed aside
the perfume and took my hand. I stood and staggered for a
few moments unused to wearing heels and having such a
tight skirt encircle my legs. Marie helped steady me and
with short steps I left the bedroom and went downstairs.
My breathing was shallow and I could feel my heart
starting to leap out of my red leather dress. Marie
squeezed my hand and left me standing at the foot of the
steps as she opened the front door. I wanted to scream, I
wanted to run, I thought that I was going to be killed, I
trembled and asked myself what I was doing. Swallowing a
hard lump I tried to stop my knees from knocking. A gust
of cold air swept into the room. I thought my heart would
stop beating from fear. Suddenly I heard a long breathe
escape and a voice say, "Tommy!?" It was Mike,
staring at me wide-eyed. "You're beautiful!" He
took a few steps forward and I quivered, trying to find my
voice. Mike paused before me, his eyes ogling my legs.
Without a thought I spun on the balls of my feet to show
him all of me. The heels pushed out my tightly leather
clad rear and I raised one hip to enhance the effect.
"I can't believe it." Mike's voice was husky.
Turning towards him again, I kept my eyes downcast and saw
a swelling in the crotch of his Levi's. He took a step
forward and I quickly looked up in time to see his
voracious lips descending. They wrapped around my
glistening lips and our tongues shyly danced. His left arm
went around my shoulder and his right followed the curve
of my torso to my hip. I shuddered and ground my groin
into his. The swelling in Mike's jeans was growing and as
it built up his right hand started to caress my leather
bound rear. Sensations cascaded through me and I almost
felt as if I was about to faint. Suddenly our lips parted
and Mike's hands were wrestling with the fly of his
Levi's. A step backward and I knelt in front of Mike as he
peeled away the denim. Ice pink nails ascended to white
briefs. From beyond the cotton a large lump appeared and
for a moment I thought about how it compared to my
stepfather's and how it shamed my small member. But that
thought was fleeting as Mike half-stepped towards my
waiting lips. Eye half-closed I fully open my mouth and
began long luxurious licks of my tongue. Soon I felt a
pulsing on the inside of my mouth and from above heard
moans. My nails were biting into the hard flesh at his
hips. Mike was now pushing his hips into my face as he
held the sides of my head. Then all at once a spurt hit
the roof of my mouth. For a second I gagged and then
swallowed and kept on swallowing and milking Mike until he
finally extracted himself. From the front door I heard a
hard sardonic laugh. My stepfather stood there, an arm
draped across Marie's shoulder. "He's all yours Mike.
For tonight." He leered at me. "Tomorrow tonight
he'll start to earn his keep." A hand disappeared
into my stepfather's pocket; "Here's a hundred."
He stepped away from Marie, "Take my 'son' out and
show him a good time. Make him feel like a woman."
Slightly embarrassed, Mike pulled up his jeans and zipping
himself he took the offered money. I came to my feet
staring at my stepfather who would not look at me. From
the hall closet Marie took out a long white rabbit fur
coat. She smiled ruefully and giving Mike the coat
scurried upstairs. Mike held out the coat and I slipped my
arms inside. Seconds later Marie was back with a small
black velvet purse and pair of cashmere lined winter white
leather gloves. As I pushed my hands into the gloves, Mike
was taking me by the elbow and walking me out the front
door. "Bring her home by midnight. She's going to
have a hard day tomorrow." My stepfather's rough
laughter followed us down the walkway to Mike's car.
"I'm sorry about that," he said under the
streetlight as he paused in front of the car. "But
not about you. You probably didn't know that I was bi, did
you?" He kissed me again and I melted into his arms
not caring that I was a man standing on his tiptoes in a
pair of high-heeled ankle boot dressed like a sexy woman.
All that mattered was Mike's warm tongue and he sure
hands. Tomorrow would be later, but tonight was now.
Part
2 >>
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The
Transformation of Kerry