THE FIRST DAY OF THE REST OF MY LIFE
By Anonymous (Larry Wand)
==================================
I didn't write this story (I just wished I had). It was posted
to a Usenet group a couple of years back; the person who posted
it said that he had seen it on a web site and wondered if anyone
had the completed story.
I have just made a number of small grammatical corrections but
the story is essentially the same as I found it. In my humble
opinion, this story rates up there with Rhonda Wagram's
"Baroness Gloria," Kate's "Sissy Therapy," and Bea's "Maid
Machiavelli."
As Nostrumo would say, enjoy.
Chrissie LaFemme (author of "Prairie Girl" and "TV Summer Camp"
and editor of Rhonda's "Fashion's Slave")
==================================
Sitting on a low bench near the mirrored wall of the dance
studio, the sweet young thing gave a tentative, nervous smile at
the pretty vision in the mirror staring back. Dressed in a knee
covering black velvet dress with lace collar and cuffs, and
admiring shapely legs clad in the sheerest white hose with a
circle of tiny pearls woven around the left ankle, and black
suede mid-heeled pumps with gros-grained bows whose pearl
buttons twinkled in the light, there was every hope that the
dance lesson wouldn't last more than an hour.
The white satin bow cocked pertly on a head of nearly shoulder
length dark tresses, became the focus of a daydream. Lori Wand,
slim, seventeen, prettily groomed, glanced at sparkling pink
tinted nails, smooth un-veined hands, and licked at the pink
tinged lip gloss that smelled vaguely of cotton candy, applied
only minutes before, in her mother's car. No need for blush on
the high cheek-boned oval face, though mom had made a big to-do
about helping put a touch of mascara on Lori's pretty, curled
lashes.
It was Lori Wand. It usually was Larry Wand, although, as he got
older it was more often Lori than Larry. Just a few hours ago,
he'd gotten home quickly from school, as mom had ordered. The
optional ballroom dancing lessons were expensive. Twice weekly
ballet lessons gave a small discount, but then mom believed in
getting her money's worth out of everything.
Larry reddened, remembering the giggling, squealing delight that
both mom and sister Jane derived from dressing him in Jane's
hand-me-downs. Although, over the past six months mom had
allowed, that is ordered, some frocks for Lori's own. And heels
too. Oh how Larry squirmed everywhere that people suspected or
guessed or knew that Larry and Lori were the same.
At school, most peers dismissed him as a sissy or swish because
of the careful grooming mom insisted on, more and more of late.
If they knew that he really wore dresses more often than the
last few Halloweens, he'd be figuratively dead. Completely
ostracized.
At the dance studio he was known only as Lori. Gratefully, it
was in the city, far from the suburb where he lived. The stylist
at the hair salon knew him only as "Larry," who always came with
his mother, who was very precise about the ambisexual style that
she wanted his hair trimmed to. He was one of many that the
young women called "gender benders," after he left the salon.
Once he'd had his nails manicured and covered with clear polish
to his great humiliation. Lately, the stylist noticed a tinge of
make-up from time to time, and a hint of girlish cologne. She
swore, to the others that he wears french cut bikinis from the
line of his pants.
Larry feared that one day mom might make a promise of her threat
to send him to school in nylons, skirt and heels, made him very
obedient and complying. The ritualistic shaming and
embarrassment never wore off. It's not that he didn't make a
pretty girl, he was a heartbreaker in a frock, it was that fear
that others might be told, or worse shown, that this was just a
pretty, androgynous, young, swishy-boy.
Mom and Jane loved the convincing charade that they created, and
never failed to remind Lori, that very little difference made
him Larry--very little. In his boy clothes, he was a boy.
Effeminate, but a boy. The difference was so slight that the
slightest change could change an observer's opinion. Sock-less,
in loafers and jeans, a girl. Socks, a boy. Shorts and gym
shoes, a boy. Flat heeled sandals, a girl. Full cut shirt and
shorts, maybe a boy. Sandals, dressed the same way, definitely
a girl--from more than ten feet away.
On those particularly embarrassing shopping trips that mom and
Jane had started insisting on, a boy-girl. Or was it girl-boy?
Dressed in thin cotton pants; blousy print camp shirt that
buttoned boy style; sock-less; in delicate loafers of equally
dubious gender; and often at their insistence, with a hint of
blush, a feather's dust of shadow, clear pink-tinged lip gloss
and lashes just tipped with matching mascara, well, poor Larry
got his share of stares, leers, giggles from salesladies, "oh,
misses," and an occasional whistle that kept mom and Jane
giggling for hours. It was especially bad if they gave him a
small matching belt purse, with lip gloss pot and silk hankie,
a thin gold necklace, and serpentine bracelet.
Once recently, they'd made him put on a pair of matte finished
ultra-sheer nude panty hose with a high french-cut lace brief
under his pegged and pleated silk blend slacks, and a thin
serpentine ankle chain with two tiny hearts. A first glance
might not reveal neutral hose, but the ankle chain made people
take a second look. Hanes didn't always make this sissy-boy
"feel good all over."
Few of the other girls and boys had arrived yet, giving the
pretty boy time to recall that fateful summer ...
Young Larry Wand first discovered the delights of silk and satin
at the tender age of thirteen.
At a time when most boys start to discover the changes that will
make them men, Larry noticed that he was soft and round. At five
feet, six inches, and 120 pounds, when he looked at himself
naked in a mirror, a soft curvy image stared back. Long slender
calves and shapely tapering thighs; a slightly rounded tummy and
smooth, tapered high waistline; Round orbs with nipples that
jutted outward in opposite direction when he folded his arms; a
slender neck with no Adams-apple protrusion; and a high
cheek-boned face with a vaguely oriental cast. His dark hair was
bluntly cut near the bottom of his neck.
Staring in a full length bathroom mirror he was struck at how
feminine and masculine he was. Musing slightly, he tucked his
small tool between his legs, holding tight with his thighs, and
quickly got an erection when he raised himself on his toes to
mimic a girl in heels.
At gym class in school, aside from not being very athletic,
girls teased him and called him "Legs" for the nearly hairless
shapely stems he sported in gym shorts.
Frequently when shopping, or on the telephone, strangers would,
to his blushing embarrassment, call him "miss" or "young lady."
It was particularly unnerving when in the company of his older
sister or mother who would catch the error and smile. He often
shamefully recalled walking home with a grocery bag in his arms
in the summer dressed in shorts to the sound of a whistle or a
horn toot and leer of a teenager who would quickly slump in
embarrassment at Larry's glare that spoke "I'm a guy."
It was just one of those summer days, with no one home, nothing
to do and the whole day ahead of him that he spent several
minutes staring at himself in the mirror before showering. " Am
I a boy or a mistake? Will I ever develop like my friends? Why
can't I sprout sideburns?" In the shower he mused and fantasized
and wondered whether some great biological pendulum was swinging
the wrong way or stopping cold. Thinking of the shame it would
cause if he didn't develop, he imagined his mother or a teacher
eventually saying "well, looks like a mistake, better put him in
a dress and bows." He wanted to be a boy--authoritative,
serious, reliable, and cringed thinking that he might have to
start acting like some of the girls in his class--giggling,
worrying about their appearance, acting delicately, without any
strenuous activity. He imagined himself in a pleated skirt and
thin cotton blouse, in penny loafers, cooing about his first
bra, as the girls did, and the embarrassment gave him an
erection.
Stepping from the shower, he dried himself quickly, and shook
off the shameful yet oddly pleasurable day dream. Resolving to
get dressed and go out to find some chums, he went to the
kitchen for a drink and fell into the newspaper on the table.
Side-tracked, after turning several pages he found himself
staring intently at the ads for women's clothing and suddenly
was fascinated by the ad-copy that continually emphasized
"sleek, smooth, shiny, bold, daring," and on and on. The
pictures and drawings were equally captivating, of undressed
women in only a pair of panty hose and heels called "nude 'n
naughty," "barely there," "bewitching black." Shoes called
"strappy sandals in lipstick red." Bras called "frothy lace
confections." The words were all very "positive," it seemed, and
he liked the idea of smooth, seamless, glistening, on anything.
Turning another page he saw a full page ad of young girl's
lingerie, with ad copy that shouted "a young teen's training
bra," "pink and lacy" "proper fit" and further reminisced about
"a young girl's first set of nylons," and the great build-up of
mother surprising her daughter on a shopping trip with her first
pair.
In one way, he was no different than any other twelve year old,
he liked gifts and the attention of adults and thought jealously
that he never really noticed any ads that said anything special
about boys. And so was planted the first seed.
Larry quickly scanned the newspaper for other ads for women's
and girls clothes and mentally compared the copy with ads for
men's and boy's. A lot of "sturdy" and other utilitarian
adjectives and none of the dreamy aspirational words of the
dress and shoe ads.
Suddenly he became chilled and his hands became cold as he
fantasized that he was in "glistening ultra sheers" and a "cool
silky, full skirted" summer dress that "peeked" and "flowed" in
a "luscious pastel print" while "striding along" in "peek toed,
pastel slinged sandals" in "the new soft pink" for summer. It
occurred to him that his sister had lots of clothes that could
be described in those terms, and he trembled and shivered at the
thought of their presence in her room ...
Larry dropped the paper and quickly bounded up the stairs to his
sister Jane's room. His hand shook as he fumbled with the door
knob. No one was home, but he felt that if he were caught "just
looking" at her clothes and personal things he would be sternly
scolded.
Against that fear he entered his sixteen year old sister's room.
He'd been in there before, but as always felt slightly
uncomfortable around all those seemingly delicate things.
It reminded him of the shame he always felt when he went
shopping with mom and sis, and found himself waiting in the
girls department while they shopped. Fidgeting, he would
carefully prepare and mentally practice his reply to the first
stranger who would dare to call him "miss" or say "can I help
you?" as if he naturally belonged there and needed directions to
a fitting room with a chiffon party dress.
He remembered once when an older saleslady noticed that he was
becoming quite bored waiting for mom and Jane and loudly
suggested to them with a wink and giggle, that maybe "your other
young little miss would like to try on that shirtwaist too. We
have it in aqua, and it would look so pretty with her dark hair
and matching open toed espadrilles." Larry had wanted to die and
melt into the floor then, but spun and got lost in a rack of bra
and panty sets. Mom and Jane had giggled at the saleslady's
remark, and treated it as innocent. He had hoped mom would have
shouted "he's my boy" or even "little man," instead of just
ignoring the need to set the record straight.
It was the memory of insignificant incidents like that, that
made the young boy wonder if he really was a mistake and that
sooner or later would be surprised by mom and Jane with an
armload of girls clothes and a new name. He mused they would
name him "Lori," and tell everyone that Larry was really too
much of a sissy, and so now would become their little girl and
sister. The thoughts of shame and excitement flowed together and
Larry soon found himself staring at a drawer full of panties. He
pulled a sheer pink pair from the pile that announced on the
label that they were "John Kloss Glossies." That was another
thing, why were men's names all over woman's clothing, he
wondered. Do they wear them too? Is it really okay, and just a
big secret kept from boys. Trembling, Larry spread the thin
waistband of the sparkled garment and stuck through a leg. The
soft elastic leg opening hugged his calf and spread open easily
up his tapered calf and thigh. He instinctively knew it would be
his size and as he slipped his other leg through his small
hairless tool grew. Pulling it up to his waist it contracted to
fit snugly around his derriere and held the small erection
against his tummy. The slipperiness and snugness of the garment
made him tingle and he felt his engorged penis throb
involuntarily, suddenly bursting with his first ejaculation. The
sensation made his knees weak as it continued to throb and shoot
semen throughout the panties soaking them immediately and fully.
He was in shock. He'd heard about this but didn't know how to
cause it. Here it happened involuntarily, and he panicked about
what he would do with sis's soaked panties. A wave of shame
overwhelmed him as he shucked out of them and ran to the
washroom across the hall. Quickly washing himself of the sticky
fluid, his mind raced for a solution to the obviously soiled
undergarment. With renewed fright he rinsed them as well as he
could and dried them before hiding them under his mattress.
Larry dressed in shorts and shirt very quickly. Guilt ridden, he
didn't want anyone to suddenly come home and find him even
partially undressed. He was sure anyone would know by the look
on his face that he done something shameful.
In the kitchen, he opened a coke and drank thirstily to wash
away the dry mouth that all that involuntary pumping had caused,
and he noticed that his penis tingled pleasantly and dripped.
Larry glanced at the clock and realized that only twenty minutes
had gone by since he first ascended to Jane's room. He felt as
if it had been hours and was quite relieved. Upon reflection,
he'd really liked it, though oddly shamed at his sexual release.
He started to think how he would have looked if he'd gone
further, imagining himself in one of Jane's dresses and heels,
and was convinced her clothes would fit as well as the panties
had, before he realized that his penis was erected again.
Stroking it through his shorts he felt the tingling throbbing
return, and pulled down his pants. Taking it in his hand he
gently pumped and the sensations increased. Larry closed his
eyes and pretended he was clicking down the sidewalk in a denim
mini-skirt and Jane's red slides and suddenly he shot the second
load of his life across his belly and chest. This time he
reveled in the sensation, forgetting for a moment the fantasy
that had propelled his hand and quickly went to wash away the
evidence.
It was only eleven thirty. No mom or Jane at least until four
thirty. Why not prove . . .
Before the thought was completed, he was bounding up the steps.
Carefully, he hung his shorts on Jane's door knob and entered.
It was thrilling, exciting, and he reminded himself, dangerous.
Sex was involved, and Larry sensed that somehow, if he were
caught, they would KNOW, that it wasn't just some innocent play
acting by him. The strong positive physical and psychic
sensations churned and led him on. He could have been
hypnotized, and hoped that if he were, god forbid, caught, that
he could argue that it was involuntary, he "didn't know what he
was doing," it "just happened." The thought comforted him. He
acted out the scene in his mind as he drew on a pair of white,
lace edged tap pants.
"Why hello, dear," mom would say, "I'll bet you had nothing else
to do and wanted to play a little dress-up. That's okay, I
understand."
But his mind raced ahead to the opposite conclusion as he
imagined being slapped, shamed, berated and threatened for his
little charade.
"My, my, Jane, your little brother is as cute as a bon-bon in
that swishy little silk of yours," she would say, "As pretty a
sissy as there ever was. Could Jane and I help you with your
make-up?"
Imagining that Jane would answer, "Mom, Larry would like to be
called Lori when he's wearing open-toed heels. I can't wait to
take him by my girlfriends in a strapless sundress!"
His hands shook as he drew on a pair of his "first nylons." They
were "nude sandal foot, garter less thigh-hi's," the package
said. Opening another drawer, he gently sorted through Jane's
bras until he found one in white lace with soft cups that seemed
to match the lacy tap pants. He stretched the stockings and
pointed his toes, marveling at he snug slippery fit and length,
and the way the knitted nylon bands hugged the top of his thighs
and brushed against his hairless balls. With a pounding heart he
tiptoed to Jane's full length mirror and swooned as he
pirouetted, noticing the lace edge of the tap pants flutter,
mesmerized by the glistening stocking slipped beneath. Hadn't
the ad said, "Hanes--Stockings for Men"?
The "getting caught" scenario continued to play out in his mind
with mom ordering, "Okay Lori, let's see whether you know how to
match lingerie. Slip out of your little frock for us, darling."
While Jane would squeal, "Oh, mom, can we take little Lori for
a perm before school starts?"
Larry imagined that if the clothes indeed fit too well he might
find himself in a dress on the first day. Somehow he felt more
shamed at the thought of wearing a pair of red open-toed low
heeled pumps like Jane's, and rather mollified by the
sub-conscious fantasy that it would be okay and unnoticed if he
came back to school as Lori in a modest skirt, blouse and
penny-loafers.
The thought of that happening made him shudder as the thin
strapped white lace bra encircled his chest for the first time.
"Titties," he thought, "lovely small mounds covered in lace,"
that would make others notice. Surprised at himself, he
wondered, "What's so wrong with that if no one knows you're
really a boy?" He carried that thought as he made his first
inexpert tries at connecting the back hook. His buds filled the
stretchy garment, and when he turned for a profile in the
mirror, he was mesmerized by the delicate protrusion, added to
by standing on his toes again, which caused a small arch to his
back and curve to his butt. "I could pass for a sixteen year
old," he marveled.
It suddenly occurred to him that "where were his heels!?" Never
feeling so naked with so many garments on, he slid open Jane's
closet and scanned the floor for sandals. Shaking and giggling
he removed several pairs, amazed at their simplicity and deft
design. He slipped his foot into a pair of white quarter-straps
on a medium heel and tottered to the mirror to strike poses he'd
seen in the newspaper. The heels fit so right and snug that he
again wondered, "Do I look better in these than in gym shoes?"
Breathing heavily, with the panties tented out on his small pole
Larry walked several times around the room, imagining the way a
girl would, adjusting his stride and maintaining balance. The
way the nylons swished as his thighs rubbed together sent a
positive signal to his brain. He loved that sound whenever a
girl walked by.
His erection continued to wax and wane with every new or
purposely repeated sensation. He wanted to try on every pair of
Jane's sandals, all her lingerie, and every color of nylons, but
he had to know how a dress would fit. Checking his watch, it was
only one.
He minced over, as he imagined models did, to Jane's dress rack.
Enveloped in the faint smell of some girlish perfume emanating
from the rack, he quickly saw a pretty pastel dress that
wrapped. Jane had worn it at Easter and he remembered how he'd
kept stealing glances at her as the dress threatened to open and
the flash of nyloned knee that she exposed with every step. Had
he been envious of her, he wondered? The label said "pure silk,"
and as it fell over his shoulders, he trembled at the way all
the slippery fabrics moved against each other, overloading his
senses.
"A very pretty dress," he mused as he swished to the mirror,
trembling with the shame of being found out. A slim willowy girl
smiled back from the mirror and he parted the dress to stroke a
throbbing cock. When he exploded for his third time, the
experience and the heels cause him to titter back and fall on
the bed. Being careful to catch the sperm, he guided himself to
the washroom to clean up.
It was there he saw the coral lipstick tube and his hands went
to it before he could think. The smell and the color flooded him
with fear again as he slipped it open and slowly applied it they
way he'd seen mom and Jane. He imagined being forced to go to
school dressed this way and some older boy who might know him as
a sissy, forcing him to kiss after applying lipstick in front of
him. Something in his mind nudged him "I like being told what to
do. I want to obey and be good." Slowly, the fantasy-idea
sprang, "I'm doing this because I was told to. I'm obedient.
It's not my fault. I don't want to wear dresses and heels. They
made me wear panties and nylons." Larry wanted to know, more
than ever, "Am I a girl? Am I a pretend boy? Or am I just a
sissy?" and he flushed a hot red at the word, shamed to his
core. Larry loved the feeling of all the silken garments,
especially the way the dress hem tickled against his stockinged
legs and the feeling of running his hands over his tush and lace
covered buds through the slippery dress.
The lipstick was moist and smelled faintly of perfume. It was no
wonder to him that girls spent so much time applying it.
He really admired the look in Jane's mirror and like the way his
bangs and hair hung from a few brush strokes. It appeared to be
a page-boy, and clearly feminine as it framed his high cheeks
and coraled lips.
Stepping lightly to the dress rack, he removed the dress and
slipped into a slim gabardine skirt, slit front and back, and
buttoned a thin camp shirt that he tucked inside. Posing in the
mirror, he winked and beamed at the girl who deftly flipped the
collar up and unbuttoned the blouse's top button to flash a
little lace. The cross-strapped lizard slings looked very smart
and Larry mused that he was dressing for work as he admired
himself. His small tool was hard again as he wondered how coral
painted toes would shimmer through the nylons. The strain of the
posture of three inch heels delighted him and he wondered
whether he might venture down the sidewalk in them.
Some time and several dress and heel changes later he suddenly
realized it was after four o'clock. Panic electrified him as he
quickly pulled off the dress and lingerie. The panties had a
small wet spot in the crotch but otherwise looked unused, but
the nylons kept his shape, obviously worn. Larry speculated that
with a drawer full, Jane would never miss one pair and stole
them away under his mattress with the morning's panties.
When the bell rang he jumped in fright. He was just finished
arranging the last of Jane's shoes, stark naked and wearing
lipstick. Larry leaped to the washroom to wash it off, grabbing
his shorts on the way, before running down stairs to answer the
door.
It was his mother, who was quite surprised to see him indoors at
that hour on such a nice day. "Marty and Pete had to be home
early today, mom," he offered. Satisfied, she went to prepare
dinner.
Larry was relieved at the glibness of the explanation, but was
fear struck when Jane arrived a few minutes later, bounding up
to her room. His fear mixed with jealousy when he saw her in a
skirt and matching sandals.
She was upstairs a long time, worrying him, that she might
notice her things had been tampered with. After what seemed an
hour, she came down dressed in shorts and t-shirt for dinner.
Nothing was said, nor any particularly probing questions asked
about his day, to Larry's relief. Without thinking of the
stashed lingerie, he swore to himself that he would never go in
Jane's room again.
The next several days passed uneventfully for him, though the
memory of the day in Jane's clothes flashed in his mind
frequently. With his friends, he would cringe at the thought of
their knowledge that he was different. At home hope mixed with
fear of being seen in a dress and casually accepted, or being
severely punished. Was it worse to be caught in Jane's room or
in her panties and heels, the young boy mused.
On Thursday morning, alone again, he took out the panties and
nylons from under the mattress. He was hard before he could draw
the first stocking up his leg and by the time the panties were
in place, a few short strokes brought him to a spouting orgasm.
The power of it caused him to relax and drift off, allowing a
rivulet to run across his belly and down his hip. Awakening, the
brush of his legs together caused a slippery tingling and he
went to wash himself off. He wanted to stay in those nylons and
hold that sensitized feeling. The extremely pleasant sexual
tension of the stocking's confinement reinforced the flowering
idea of more experimentation. Larry's heart leaped at the
fantasy of being accepted by his mother and Jane and going out
with them in a skirt and heels, to shop and then lunch, the way
mom and Jane often did together.
Mom was a real estate broker, which allowed her a fairly
flexible schedule and Jane could always count on her for lunch
and what Larry presumed was "girl talk." He wanted to be part of
the group. Was that it? Or did he want to wear dresses? Larry
wasn't sure, although he knew that if he wanted, he was always
welcome on their excursions. Before now, spending time shopping
with them was an unwelcome chore. Now he somehow wanted to let
them know that he understood, or thought he understood, why they
were so preoccupied with clothes and appearance.
Subtly, over the course of the summer, Larry started changing.
He paid closer attention to his appearance. He lessened his
involvement with friends; fairly easy when you're not too
athletic, and always the reluctant last choice in a pick-up game
of baseball or other sport.
At home his dressing fantasies became very mercurial. Some days
he plunged at Jane's clothes, prancing and masturbating until it
hurt, and hoping the day wouldn't end. On other days he felt
guilt ridden and unclean and worried that the things he'd heard
about masturbation might be true and might show on him.
His greatest fear was the uncertainty of his family's and
friends reaction if they discovered his secret. Of his friends
there was no doubt. The slightest effeminate trait in his peer
group was ostracized with chants of "sissy, lacy-pants, femme,
faggot, homo, pussy" and other words too numerous to mention.
Not to forget the drubbing a boy might likely get from his
friends for showing up at the park in too new gym shoes, shirt
or pants, or anything other that jeans or shorts. God forbid a
dress shirt and tie on a week-day. Or a pair of shined loafers
and khakis with a clean pullover shirt.
He was less sure of his mom's and Jane's reaction. His parents
had divorced many years earlier, so he was relieved that as he
imagined, there'd be no father to bully him and disappoint. He
was sure there wasn't a father alive who'd rather see his boy in
a dress and sandals with bows in his hair.
As for Jane, at her age, he guessed from her dating and
conversations that she wanted masculine images from all men and
would tease and shame him mercilessly if she saw him in training
bra and panties. Mom, he was sure, or at least hoped, would be
understanding and forgiving. At least so long as he wasn't
caught sneaking among her and Jane's private possessions.
Personal privacy was respected in their house, and he knew any
seeming transgression would be dealt with sternly. So how could
he dress, without girl's clothes of his own? Could he dare ask
them to try something on? "Oh mom, do you think Jane would mind
if I tried on her yellow chiffon prom gown to see how it looks?"
he thought, and was sure mom would faint before showing him the
business end of a belt. Could he spring it on them one
afternoon, by greeting them in a dress and hope they took it as
a light hearted try at comedy or fun? Would they both want to
shame him? He sensed it was wrong, and if they made him undress
after caught in a frock and heels that they'd send him to a
doctor. The fear of rejection and the probable humiliation
forever after, kept him cautious and discreet. If he could only
gauge their reaction. To Larry, it was obvious that there was a
strong sexual undertone to wearing sheer black stockings and
ankle strap sandals. At times he dreamt he had his own that mom
would admire him in, commenting on his pretty legs. Other times,
the realization of their effect on him, he guessed his mom could
easily "read" and would die sooner than having him go out in
public that way. "How do you please everybody?" he speculated.
At times, lying on his bed, dressed in hose, he mused that he
should spring it on them, but that fear of rejection, and
subsequent shame held him back. Few of the twelve year old girls
he knew wore nylons. How could he? Even, as he thought, his legs
looked better than most sixteen year olds.
Early in July, in the jumble of summer, some weeks after that
first taste for nylon and heels embedded itself in his mind
Larry felt that, if he at least had his own dress and heels,
there'd be no problems with the issue of privacy if he were
caught. "Could I go to the mall and buy a dress? Nylons, heels,
panties, bra, lipstick and eye shadow?" Jane had only started
wearing make-up a year earlier. What would mom say about him if
she knew? He had some of his own savings and practiced the
scenario over and over in his mind. "I'll just go in and buy one
item in each store." I'll say that the nylons are a gift. The
dress is a birthday present for my sister. The sandals ...," he
knew it would be unbelievable. Maybe just some nylons.
"My mom got a run and wants me to buy three pairs of Christian
Dior Ultrasheers in 'Barely Black', sandalfoot. Uh, I think she
said sheer to the waist, size C." That's what Larry blurted to
the saleslady at Saks. She winked and smiled but gave him his
purchase and asked, "Maybe your mom would like some stockings
too?"
Flushed with embarrassment, he said, "What colors do they come
in?" And the saleslady knew she had him hooked. She was in her
thirties, it seemed, close to his mother's age. Tall and smartly
dressed, the tinge of irony and sarcasm in her voice was gentle
enough to keep Larry from bolting from the store. "Well dear,
they come in many colors, from a neutral shade that's nearly
undetectable to that naughty black color in your bag," she
smiled. "Let me show you," she said to the entranced and
embarrassed boy. "These taupe shades--a sort of brownish gray,
are very becoming with your dark hair," she grinned. "Oh, I'm
sure your mother must have a very similar color," she quickly
added, to save him the sudden red-faced shame. Adding, "I'll bet
you look a lot like her."
Larry was already frozen with fear and desire and whispered
dryly, "Yes, I do, I mean, we both look alike."
The saleslady smiled back, "I thought so dear," knowing that the
slim young boy in front of her was buying nylons for himself.
She was intrigued, and not the least surprised, since many men
and boys came to her counter to buy stockings for "others" all
the time. She'd met and knew any number of sissies while working
as Saks, and somehow felt a sympathy for her regulars, whom she
sold stockings to without ever flinching or revealing her
knowledge. Larry struck her with his politeness. He acted rather
submissive and demure and was not the least defensive, though
probably out of fear and some "first time" buying guilt. "Why
don't you just step back here," she motioned to a remote corner,
"and look this selection over. I'll be right back to show you
some different styles."
CHAPTER TWO
*******************************************************
Numbly, with trembling hands, Larry picked through the gossamer
samples, as the saleslady walked to the counter. She busied
herself and glanced at the boy from time to time, noticing that
from different angles he seemed all that he was, rather
androgynous, a pretty boy from one angle and a cute young miss
from another. She mused to herself that he probably dresses
every chance he gets, and approvingly observed very shapely and
nearly hairless legs in the boy-cut shorts he was wearing. His
thick dark hair needed little touching to create a feminine
style she thought, and guessed that with a little padding he
probably looked very pretty in a size 8 dress.
She walked back to him, "Have you found some colors that you
like?" adding hastily, "for your mother?" He whispered, "Yes" at
several shades of grey, blacks of varying intensity and some
neutrals. The woman thought, "Pretty sophisticated tastes for a
boy. Dear, let me show you the very wide variety of white shades
that are popular with young women" ever careful to not directly
confront him with their secret. "I really think this ultra sheer
white is a very pretty summer shade, don't you agree?" Larry
nodded. "Of course, these come in panty hose and gartered as
well as thigh tops. Does mother wear garters?" she grinned.
Larry was stunned and tried to stutter an answer, but how could
he tell her he liked garters and thigh tops? She saved him from
an answer. "Why don't I just give you two pairs of these lace
topped stockings? They are just divine with a summery dress and
sandals, especially if your legs are tanned," she smiled,
obviously looking at his legs. Larry regretted that he was in
shorts, and suddenly felt she was ogling him. "Now, dear, here's
a pretty little set that we sell in the hosiery department. It's
a sheer lacy tube bra, high cut french panties to match and
silvery black lace topped garter less stockings. Do you think
she'd like those? They're on sale for eight dollars. Why don't
I give you a set, okay?" she encouraged. Larry faintly smiled
his appreciation, though her eyes bored humiliation right
through him. As he paid, she thanked him and suggested, "Now,
dear, if you ever need any help picking something out for your
mother come see me. I think I can pretty much guess her size.
I'd be happy to help you," she winked, as she handed him the
package. Striding quickly from the store he noticed the bulge in
his pants and wondered whether she'd noticed. Oh, she had.
When Larry got home he hid his purchases in the back of the
closet except for the teddy hose set. Stripping down, he
trembled as he rolled the stockings up nearly smooth tanned
legs. The high cut bikini panty came next and then the stretchy
tube bra, whose smooth elastic pushed his fleshy buds up to fill
the fabric. Entranced, he found a pair of black patent pumps
with grosgrain bows in Jane's closet and pumped and shot several
loads of pubescent semen on the bedroom floor before dosing off
on his bed to daydream of wearing the pretty little set
outdoors.
How could he ever wear this in front of his mother and Jane he
shuddered.
Changes at the Wand home never went unnoticed. Linda Wand,
although divorced, was a parent who didn't let business and her
personal life get in the way of raising Jane and Larry. She'd
begun to notice the subtle shift in Larry's habits, he was
neater; home more often when she returned for dinner as well as
occasionally when she stopped at home for lunch. Jane worked at
a beauty salon for the summer as a shampoo girl, contenting Mrs.
Wand that her time was occupied. Larry, on the other hand, had
his morning paper route and was then free for most of the day.
Subtly, she'd noticed personal items in their washroom had been
moved, and had heard from Jane that personal items were
misplaced or missing. This was rather unusual only because Jane
was fairly fastidious, although Linda dismissed this to Jane's
working a full time job for the summer. It was only after a
particularly long day when Jane was almost in hysteria that she
couldn't find a new pair of stockings that she was sure she had
and simply couldn't go out without that Linda became concerned.
She resolved that she needed a few days off to catch up on
housework and clear up the mislaid and missing clothing as well
as to check on Larry's habits. It was while cleaning the
upstairs bedrooms that she noticed Jane's sandals behind the
hamper and her own things scattered and mixed with her
children's that she thought a thorough cleaning was needed. And
it was in Larry's room that she was struck with the incongruity
of Jane's panties lying on the floor of his closet. "Hmm, this
family is scattering its possessions far and wide. How could
Jane's underwear find its way into Larry's closet?" That evening
at dinner she mentioned what she had found very casually in the
course of reminding her children that summer vacation wasn't a
vacation from tidiness that she was struck by the look of
embarrassment that swept over Larry at the panty's mention. And
she started to wonder. Larry had become very fastidious of late
and was at the threshold of manhood. Like many boys his age he
had an angelic, androgynous, no girlish look to him, and she
wondered whether he had too much free time and was trying on her
clothes or Jane's.
The next morning she decided to make a careful search of the
house to see if there was something amiss. It was in the
basement that she noticed the pair of worn thigh top stockings
balled up behind some boxes. They hadn't been dropped there,
they'd been hidden. The idea that sprang to mind was quite a
shock. "Larry? It couldn't be. He did have that vague girlish
boy look to him and not a very muscular body. Smooth and
hairless, except for sprouting leg hair. Could it really be
him?" Linda imagined that he might have tried out the stockings
purely out of childish curiosity. No harm in that. She rather
fondly recalled dressing Jane and Larry in matching pink
Southern ante-bellum dresses for Halloween, when Larry was five
and Jane eight. He'd been rather embarrassed then about putting
on the new white tights and bowed white patent pumps that Jane
had grown out of. That was the last time she was ever able to
coax him into a frock. Linda had really loved their appearance,
and had fantasized that she had two daughters. She treated Larry
softly and gently during those years out of love and that
sub-conscious wish that he was really a daughter too. Every
Halloween she and Jane would ask if they could dress him up as
a girl and every year, the ensuing teasing shamed and
embarrassed him to tears as he steadfastly refused their offers.
She wondered and thought that maybe she should test her theory.
That evening at dinner she said, "Children, I've been doing some
housecleaning and want to send a number of boxes to the Amvets
Store. Could you please box up anything you want to give away.
Larry, be sure to bring down your old winter coat and the gray
suit you've grown out of as well as that hockey game. Jane,
don't you have a number of dresses and shoes that you're not
wearing this year?" Don't forget that junior prom dress. You'll
get a new one for the senior prom, and there's probably a needy
girl who'd love to have one." She stole glances at Larry and
noticed how he perked up at word of Jane's clothes. She'd
guessed right.
A few days later, as she packed the boxes she loudly announced
that they would be picked up the following Monday and asked
Larry to take them out to the garage. He was only too happy, she
noticed. On Sunday afternoon an inventory while her children
were out revealed the prom dress, a pink shirtwaist and several
pairs of Jane's shoes were missing. Linda expected that she knew
where to find them.
Early Monday, as she and Jane left for work, she smiled and said
she'd be late that day, and that Jane and Larry should eat
dinner without her. Larry sat and trembled with anticipation.
The yellow strapless chiffon gown that Jane had worn in May was
his, safely hidden in the attic. As soon as they left, Larry
made the ritual rounds of the house to check that the doors were
locked and the shades to his room drawn. Linda in the meantime
planned to send someone over that morning with a package
delivery, as soon as she thought Larry might be dressed in his
new finery.
Larry bounded to the attic. Stripping off his t-shirt and
shorts, he wore no underwear. He slid the white sheers up his
legs and stepped into the full skirted gown. Failing with the
zipper, he turned it backwards, zipped up and twisted it around.
It fit very nicely as his hard cock revealed to him, though it
was well hidden under the voluminous layers of chiffon skirt.
Taking some socks he filled out the vacant cleavage and
carefully stepped into a pair of white sandals that he'd gleaned
from the box.
Linda was in action too. Waiting for twenty minutes (that should
give him time to parade down the stairs), she told the office
messenger to deliver a set of blue-prints to her home. Someone
would be there to accept them. When she was sure that the
messenger was within a few minutes of arriving she rang home.
Larry was in the mirror and froze in fear. Should I answer?
Well, why not, no one could see him over the phone, and if it
was mom, she'd get angry if he didn't answer.
Linda knew that if her timing was right the doorbell would ring
while they were on the phone and Larry would have no choice but
to answer the door. Stepping to the phone in the high heels,
Larry answered on the fourth ring, "Hello?"
"Hello dear," his mother answered. "Larry, have the Amvets been
out for the boxes yet," she asked.
Fear-struck, he'd forgotten they were coming, he said, "Why, why
no mom, not yet," and thought he better peel out of the gown
quickly before they came.
"Now listen carefully, dear, a messenger will deliver some
blueprints this morning that are very important to me. Be a doll
and wait until noon for them would you?" she pleaded.
"Oh sure mom, happy to," he nervously replied, thinking, well,
no panties for me today.
Suddenly the door bell rang impatiently.
Linda heard it over the phone, "That might be him now dear,
wasn't that the bell?"
Larry froze in shame and animal fear: twenty feet from the door
in a chiffon strapless dress and mom on the phone.
"Please, dear, I'll wait, see who it is."
Larry was numb.
The doorbell rang again. "Larry, dear, put the phone down and
answer the door," she smiled, knowing what Larry's dilemma was.
The fear struck panty-waist felt as though his spiky sandals
were cemented to the floor. There wasn't time to shuck hose,
heels, bra and dress. The sissy's mind raced. Although no one
could see him--yet--he slowly felt himself becoming shamefully
red-faced.
The door bell rang again.
"Larry! Please, darling, go answer the door. And, oh, dear,
please ask the messenger to the phone, I'll want to ask him
whether they're the right prints," Linda added, cleverly
calculating that this should cure her son's panty passion.
Shock struck the trembling sissy boy. "Mom, I'll just ask him
for you," he snapped, thinking quickly, that he could just have
the messenger pass the blue prints through the door.
"I'm sorry, dear," Linda smiled wickedly, "I really need to ask
several details." She wondered whether his dressing was still
rather tentative, and guessed that he was wearing the pink
striped oxford cloth shirtdress. Linda had recognized his
effeminate features and thought his legs probably looked rather
pretty in the knee length frock, especially with the tan open
toed slings that she'd noticed missing from the Amvets box.
"Dear! Quit jabbering and answer the door before he leaves," she
ordered.
THAT thought really made Larry quake. He imagined running down
the stairs in daylight and out to the street to call back the
messenger. One of the neighbors was bound to see him. And with
the way his luck was going, it would probably be that sixteen
year old muscle bound bully Tony, from across the street. He'd
been very interested in Jane and would probably recognize that
it was Larry and not Jane in the strapless chiffon. That would
be the end for life. Tony didn't particularly like him and Larry
imagined that word of his tripping down the sidewalk in heels
and hose would pass like wildfire through the neighborhood. What
to do?
"LARRY!" a rather eager Linda scorched at him.
"I'm going, mother!" Linda recognized his voice of exasperation
and held the phone away as she tried to stifle a giggle and
mused that he even spoke girlishly. She was dying with curiosity
to see her son's transformation to part time sissy, and wished
she was there. "Maybe when I get the car phone ..." she thought.
Larry was not yet very expert with heels. It required all his
concentration to stand in the stiletto sandals, as he weak-kneed
his way to the front door. "I'll just have to act like I know
what I'm doing," he weakly hoped, as he opened the door.
"Well, hello there, miss," the young messenger grinned, as he
gaped at the pretty, sweet young thing who answered the door.
Larry just then understood what his sister meant when she'd say
to mom or her girlfriends that someone was "undressing her with
his eyes." He felt very naked. His small roundish orbs jutted
out and up from the padding he'd stuffed below them. The heart
shaped neckline happily revealing an expanse of soft hairless
chest and more than half of the orbs that protruded above his
chiffon swathed nipples.
"Gee, I'm sorry," the messenger grinned, staring at the pretty
legs and slim ankles that peeked out from under the mid-calf
length of sheer chiffon. "I'll bet I caught you dressing,
right?" he said with a wink and apologetic voice.
Larry shifted in the sandals, wishing the dress would somehow
grow a turtleneck, sleeves and a floor length hem. This guy just
smiled and never looked you in the eyes. Larry's face reddened
shamefully with understanding. The young sissy spun on his
spikes, surprising himself with unexpected deftness. Trembling,
and dry mouthed, he said, "My mom's on the phone and would like
to talk to you before you leave. The phone's by the stairs."
Larry minced into the living room a few feet from the phone,
hoping to stay a bit out of the young man's eye sight, but near
enough to step over quickly if he was wanted on the phone. The
messenger's eyes tried to follow, but he quickly fell into
conversation as Linda asked questions to keep him on the phone
for a few minutes. She hoped Larry was squirming. The sissified
lad stood trembling with his back to the messenger. He could
feel his heart pound and ears ring and burn with shame. As a
cool breeze from the partly open door licked his ankles and
drifted up his thighs the coolness made him realize that he was
starting to perspire from his embarrassment. Trying to collect
his thoughts, it suddenly struck him that the fear of being
"read" shamed him and uncontrollably excited him. "Is she or
isn't he?" He trembled in fear, and felt his cock rising in
excitement. "Is this right?" It really worried him that as small
as he was, it might show a bulge in the chiffon. It would only
be after the messenger left that Larry, standing in the open
door way with the sun shining in would realize the show the
young man got from the sun-light silhouetting his shapely gams.
The sight would give him a new erection.
Linda wondered what he might be doing and said to the messenger,
"Would you ask HER to come to the phone?" It didn't occur to
Larry then that mom had used the feminine pronoun. But he did
cringe when the young man said, "Miss, your mom wants to speak
with you." He prayed that she hadn't heard, but Linda had, and
was beside herself with glee. "Now Larry," she said when he was
on the phone, "is Jane there with you?" She smiled as he
stuttered a, "Nuh-nuh-no, mom." The little swish had wasted no
time at all, she thought. She wouldn't press it for now, but had
to know whether her hunch had been correct. Did the little panty
waist favor gown or shirtwaist? "Okay then, dear. Just listen.
Can you bring those prints down to the office for me later?"
"Yeh-yes, mom," he replied in a quavering voice that he hoped
didn't sound too boyish to the messenger or sissyish to mom.
"Okay then, dear, let me speak to Jim again," she said. He
handed the phone back to the smiling messenger, who'd had a long
look at his bare back, derriere, and pretty, tapered calves.
"Yes, Mrs. Wand?" he asked. Linda became conspiratorial and
nearly whispered into the phone, "Now, Jim, just tell me one
thing, with a "yes or no" answer. I don't want my daughter to
know, but is she dressed in a fairly pretty ball gown?"
"Oh, yes, Mrs. Wand, yes indeed," Jim replied rather too
enthusiastically. It worried Linda, as she stifled a laugh, that
maybe the young man might want to press his advantage, "Well
tell me, Jim, is she in heels?"
"Oh yes, ma'am," he smiled into the receiver. "Thank you, Jim,
you may go now," she replied, feeling safe that the messenger
would just stop for one last long panting look and nothing more.
"Larry, sweet, please bring the prints over before noon love,
okay?" she said as she rung off. It wasn't until Larry stripped
out of the nylons that he realized that the messenger hadn't
flinched when mom asked to call him to the phone. She knew.
When he got to her office he wanted to drop the plans with the
receptionist and run, but mom expected him, and wanted to watch
him squirm for a while. "Well, dear, how was your morning," she
smiled, almost laughing.
"Fine, mom," he said, averting her eyes.
"Larry, was there a girl with you this morning?" she asked in a
friendly voice.
"No-no mom!" Larry sputtered, turning beet red.
"Well, that's odd, I thought Jim said 'Oh, miss' to someone,"
she grinned broadly, carefully dancing around the discovery. The
confrontation could wait for a day when she could find him at
home, and as she imagined, probably just pirouetting in front of
a mirror. No harm in that. "If I handle it right," she thought,
"he might be our occasional 'dress-up doll'. I might even be
able to handle him better in a dress. Might make him a little
neater and obedient, if he knew there was a dress for
punishment--or reward," she mused, "No need to rush into this
now."
Larry stopped trembling enough to squeak, "Can I go now mom?"
"Well, Larry, wouldn't you like to have lunch with me?"
thinking, it would be exciting to watch him squirm for a half
hour of innocent questioning.
"No-no, mom. I'm not really very hungry," he smiled wanly. "I'll
just get going, to meet the Amvets guys when they come."
Linda smiled as he nearly tripped, beating his retreat from the
office.
Larry's embarrassment was numbing. What had mom said on the
phone to Jim? "Call Him to the phone?" No, that would have
startled the messenger, and his surprise would have shown. "Let
me speak to ... her? My daughter? The girl? The young lady." Try
as he might the panic-stricken boy couldn't think a single way
mom could have avoided using a feminine pronoun. By the time he
reached the house, Larry mind was churning dozens of
explanations. But, "How had she known?" What had tipped her off?
The young boy's mind raced. His stash of nylons? He was sure
they were safe at the bottom of a box full of old family albums.
He was sure that she hadn't been to the attic. Had they noticed
that their make-up had been used? "No, it couldn't be that
subtle." Then suddenly, it occurred to him. He sat down
trembling and nearly on the verge of tears. It must have been
the saleslady at Saks. "She must know mom or is a friend of
hers. So mom would know that he'd spent thirty dollars buying
pairs of panty hose, stockings and that "teddy hose" set. Once
irresistibly attractive to him, he wished that he'd never been
to Saks. He wanted to go to his hiding place and tear the
gossamer garments to shreds. He imagined mom saying at dinner,
"Larry, after dinner, please go put on the pretty little bra and
panty set, and the matching nylons, dear. Jane and I want to see
her new little sister." He shivered thinking of parading in
front of them in lingerie. Worse yet, it was all so sheer that
they'd see his penis and nipples through that glimmering fabric.
Jane didn't have anything so blatantly sexual in her dresser.
And mom, well he never thought of her in sexual terms. She was
pretty, tall, and well dressed, but even she didn't have
lingerie like his. Larry wondered when the "boom would fall,"
and dreaded dinner that evening. Then he remembered, mom would
be home late and dinner was on their own.
That evening as he and Jane sat down to burgers and fries, Larry
uncomfortably thought that mom might have already said something
to Jane, and waited with fear to hear Jane make a remark.
Nothing happened. Depressed, Larry stayed in his room after
dinner with the television on to keep him company as he thought
of how he would explain the lingerie purchase to mom when she
asked. But that couldn't explain the phone conversation that
morning. Did she think he paraded in front of a stranger in bra
and panties? He wondered what she thought of him now. At eleven,
he was startled by his mother, who knocked and stepped into his
room. "Hi dear. I'm home. Have a good day?" she smiled. "Oh sure
mom, fine," he replied, dreading the ax fall. He averted his
eyes when she enthusiastically asked, "Do anything interesting
today, love?" "Oh, no mom, just a lot of the same," he blurted.
Linda Wand smiled and wondered, "Well then, good night, love."
"G'night, mom," he said, relieved. For the moment.
At breakfast, the next morning, mom told Larry to pack some
clothes to visit his uncle and aunt at their summer cottage for
a week. A very relieved Larry Wand, enthusiastically sprinted to
his room, thinking that in a week this should blow over. "She'll
forget, and I'll promise to start over and be good," he thought.
Linda Wand had planned this at work the day before. There was no
forgetting.
Packed off for the week, Linda started her search in spare
moments. By Thursday, she'd not only found the gown, shirtwaist,
five pairs of shoes, and to her gleeful surprise, two of Jane's
old training bras, but the wickedly sexy "teddy hose" and
stocking collection. The stain on the lacy, high cut black
panties worried her. "He's becoming a man," she thought, "but
what kind of a man? This boy wasn't just innocently play-acting.
There's more to him than prancing in the mirror in a pair of
spiked sandals." Slowly the plan evolved. She'd have to be slow,
patient, and firm with Larry. "Not Larry, my darling, dear,
sweet, swishy, effeminate, sissy boy ... Lori," she gleefully
mused, "my little doll. My primping prima donna in ballet class.
A delicate little wisp to tease boys with. Jane's dress form. My
little tart in mini and red, spiked mules. Our little deb, ...
all with time." Linda resolved that there was still the whole
summer. That this could be done slowly and gently. Fire and ice.
Assurance and teasing. Humiliation and reward. It would be fun.
For now, Jane had to be kept out of the little secret. In fact,
Linda thought that she'd probably have to cover for Lori, if he
kept trying and wearing Jane's things, until the time that she'd
share his secret.
Back home after a week, Larry felt refreshed and cleansed.
Swimming, boating and playing with new friends for a while who
accepted him uncritically, drained him of the previous week's
heavy psychic baggage. He was eager to be alone in the house and
invade his secret cache. The next morning, without skipping a
beat, mom and Jane left for the day. After the careful check for
dead-bolted doors, he took the stairs two at a time to the
attic. Nothing was out of place. The pink stripped shirtdress,
still hidden under a winter coat in the hanging garment bag,
came out first. Larry had ironed it after taking it from the
Amvets box, and the shirt tail hem and side slits invited him to
slip in. Undergarments first, though. He was sorry now that he
hadn't asked the lady at Saks whether the "teddy hose" came in
other colors. It would show through the dress. Slowly, fighting
a looming erection, he slid the panties up, and fantasized that
he was dressing for a day of shopping. Sitting on a trunk, he
carefully rolled a pair of neutral hose up his legs, admiring
their form as he held his leg out and arched his foot, the way
he'd seen models and women in movies do it. He hastily drew on
the lacy strapless tube bra and massaged his throbbing organ
through the nylon and lace. Peeling down hose and panties to his
thighs he reclined and let his hardness subside. He really
wanted to slowly savor this first session after the week's
vacation.
As he tucked the flaccid organ down to minimize the bulge he
accidentally brushed a box aside, spilling it on the floor. He
was awe-struck. Make-up! Larry couldn't recall seeing it in the
attic before. Here were used lipstick, mascara, blush, gloss, a
large palette of eye-shadow, and he excitedly saw, pale pink
nail polish! Without thinking of anything, he peeled off the
hose and slowly painted his toe nails, as his small tool
throbbed its approval. It didn't occur to him, then, that mom or
Jane had anything to do with the box of old make up. But Linda
had. Larry rolled the stockings back on admiring the twinkle of
his double-coated toenails and couldn't wait to see them sparkle
in the pretty white sandals he'd worn with the gown. Slipping an
arched foot into them as if being helped at a shoe store, he
swooned at the way they commanded his concentration. Thighs and
calves responded with unused muscles as he put his feet together
to admire nylons, heels and polish. "As pretty as any girl," his
mind soared, blocking out the negative. Carefully, he unbuttoned
the dress to below the waist and stepped each sandaled foot
through. It slid onto his shoulders perfectly, he thought as he
left a few top and bottom buttons undone to provocatively flash
the bra and his shapely nylon clad legs. Make-up! It took all
his concentration to keep from shaking at his good luck. He felt
his tucked tool ooze and hoped he could try a few things on in
the mirror before he exploded with passion. He was indescribably
in love with himself. Stepping carefully down to the bathroom,
he swooned with envy at his sister who wore clothes like this
every day. The image in the full-length mirror winked its
approval at the pretty teen in pink stripped shirtwaist, whose
knees sparkled in the light with every step and pose. He opened
the tube of lipstick and slipped it across his mouth.
Remembering Jane at the mirror he tried to deftly touch his
cheeks with pale blush. It was the mascara and eye-shadow that
he knew he'd have to be careful with. Choosing a light dusting
of gold, he followed over it with a soft pinkish color. "Not too
bad," he thought, "plenty of room for improvement, but at least
it wasn't hookerish."
He fantasized himself a high school girl. Done, he went to the
long mirror for approval before going down stairs to walk about
and practice the heels on the carpet and hard floors.
Shamefully, a thought came to mind. Practice what? He knew he
could never go outside like this. His neighbors would see him.
Anyone could tell he was a young boy in a dress, he thought. It
was almost noon. He realized he'd been dressed for nearly two
hours. As much as he enjoyed the recurring throb and tingle of
his little tool, he really wanted a release. While he had been
mincing over the carpet and through the house, practicing in the
slippery heels ("how were girls able to do it? Slip and slide in
sandals, wearing nylons"), he imagined being at school, working
at a job, and suddenly, uncontrollably, out on a date, like his
sister Jane, with a boy. He shook his head to clear the thought
but it continued to press, and he noticed to his alarm that his
tool was really becoming hard. The fantasy washed over any guilt
or shame that called from his subconscious as he let himself
imagine holding hands, being kissed and held, and dancing in his
heels and dress. As he ascended the stairs to his room he
imagined an arm around his waist.
Larry sat on the edge of his bed, smoothing the dress beneath
him. He undid the three remaining buttons from hem to waist.
Lifting his legs onto the bed he crossed and uncrossed them,
delighting in the nylon's slipperyness. "Where did this boy come
from?" he dreamily wondered, imagining that his slow strip was
for the dream boy's benefit. It was this young man's hands and
not Larry's that cupped nubile breasts and petted his pantied
tummy and inner thighs. Larry rolled the hose to his thighs and
pulled his hard sticky tool through the black lace panty's leg.
He rubbed the clear fluid over the shaft and shot a burst over
his left shoulder into the headboard on the third stroke. He
mewed as his hips bucked and he kept rubbing the slick shaft
spurting now onto his hand. Spent, he laid back and closed his
eyes. Suddenly, he felt shame. The nylons and sandals were
constricting. The make-up felt like clay and he wanted to tear
off the dress. Springing from the bed, he slipped off the
garments and sprinted to the shower. "That was it. No more.
First chance I get, all this gets carried out to the trash," he
resolved. Dried, and dressed in shorts he hurried to the attic
with his things, carefully replacing everything, before going
out in the sun to burn off the shame of the morning
That evening, after dinner, with both Larry and Jane out of the
house, Linda inspected the attic and delighted to find that
Larry had found the make-up. She giggled looking at the wrinkled
shirtdress, imagining Larry prancing about in the sandals that
she noticed had been moved. She wanted to see him dressed,
unnoticed and planned to pretend leaving for work the next day.
The following morning, with Larry still upstairs, she shouted:
"Bye, Larry, see you tonight!" and loudly shut the door. The car
had been parked in the garage the night before.
Hearing his mother leave, the compulsion to slip into nylons
overcame the budding sissy. But no dress today. Just hose and
heels to relieve the tension growing in his shorts. Slipping
into the lace panties and bra that he'd carried down to the
living room, he now carefully rolled the matching thigh top
stockings up his smooth shapely legs. Linda watched from the
quiet of the darkened kitchen, careful to make no noise. In the
sexy little ensemble, Larry made a very pretty girl, she
noticed. She was especially struck with the way his longish hair
looked really feminine when he had the bra and panties on. Those
legs were really pretty in the sparkling nylons. When she saw
him slip on the white spikey sandals she was amazed at their fit
and made a mental note to plant a pair of her old asymmetrical
strap black patent slings in the attic. The way he tried to
mimic swaying hips almost made her laugh as he strode toward the
stairway in the nearly transparent panties. He slowly walked up
stairs and Linda followed from a safe distance on stockinged
feet. He never heard her as he lay down on his bed in the heels
and hose, caressing his scantily clad body and stroking his hard
penis through the sheer lacy panties. Linda stood mesmerized,
peering through his door, as she watched him get obviously
excited and moan from his own caresses. When he withdrew his
tool from the panties, she was struck with its delicate,
diminutive size. She was dry-mouthed and breathless as she
watched his hips buck to his hand's rhythm and his back arch as
he shot several waves of pubescent semen over his chest. She
quietly retreated to her room to reflect on the little tableau
and wait until he left the house. It was clear to Linda that
Larry didn't spend as much time