Test Driven
By Gingerfred Man
A Pantyboy Profile
INTRODUCTION
My name is Cheryl. I'm 20 years old and I'm a
pantyboy.
My best friends, Judy, Amy and Sandy, are pantyboys
too. Simpering little sissies made for the pleasure of
nice men who treat us well.
Pretty little angels with mouths and bottoms eager for
cock.
We've all been featured in our favorite magazine,
Panty Boy, a celebration of all that is sissy and
wonderful in the world.
I know it's your favorite publication too, Honey, or
you wouldn't be reading this story.
I hope you've read "Service," where I told you all
about my friend Amy and how she got to be the object
of millions of men's stroke fantasies. If you didn't,
that's OK, because this story about Judy stands alone.
Just like your cock when you read my stories. But I'm
assigning "Service" to you for homework.
My friends gave me the task of writing one story about
each of us, then one about our lives together as VERY
popular sissies in New York.
You'll love this story about Judy. She's so sweet and
pretty. Like me, Judy is a blonde. Her hair is long
and straight, all the way to her shoulder blades. She
has the prettiest three-and-a-half inch cock in the
world and perfect erect nipples, framed by her
bra-shaped tan lines.
But she wasn't always beautiful and desirable. Like
the rest of us little cock-hungry pantyboys, Judy
started life as an icky boy. Her name was even icky ?
Harold. If any of you readers named Harold are mad at
me for saying that about your name, maybe I can make
it up to you.
Anyway, let me tell you all about Harold the Dull and
how he became the little sexpot angel Judy. Get your
tissues ready because it's a very stimulating story.
Chapter One ? Dull
Harold's life before his 18th birthday was very dull.
Contrast that with Judy's life, where she's being
squired around the world by rich, beautiful men who
give her things ? expensive jewelry, bearer bonds,
real estate, big cocks in her tight pussy. Being Judy
is way better.
Harold Strokewood lived with his mother, his father
having run off with his secretary or someone when
Harold was quite young. His mother tried hard, but she
couldn't seem to jump start Harold. He wasn't
interested in girls, boys, men, women, school, movies,
video games, sports or even recreational drugs. He had
no friends to speak of and no ambition. Mrs.
Strokewood hadn't even caught Harold whacking off or
reading porn or sniffing her panties or anything that
a normal boy does. A psychologist who knows which end
of the telephone to talk into will tell you that there
are two possible diagnoses. Either Harold had
"pantyboy malaise," which meant he ached for the
pantyboy condition, even though he didn't even know
such an exalted state existed, or he was a jerk. Since
Harold's mom didn't know about pantyboy malaise, she
had concluded that the second diagnosis applied.
Harold graduated from high school the day before his
18th birthday and, since he rarely planned beyond his
next meal, had no idea where he was going in life. And
didn't seem to care.
Thank goodness for Mr. Stiffman.
Gerald Stiffman actually approached Harold's mother at
graduation and asked if Harold would like to work for
him. Mrs. Strokewood looked over her shoulder to see
whom Mr. Stiffman could be addressing. Surely he
didn't want Harold.
But he did. And he was insistent.
"Young Harold would be a great asset to my store,
Stiffman Intimate Apparel, Mrs. Strokewood. Harold has
a future in lingerie."
Well, no swami could have made a better prediction
than that statement. But Mrs. Strokewood thought Mr.
Stiffman was hallucinating or something about her
Harold. When she realized that he was serious, she did
what anyone would do when dealing with a rich person
who was being careless with his assets. She took his
money. Stiffman offered Harold's mom an employment
package for Harold that made her eyes bug out. Though
Harold was to reach his majority the next day, she
knew he would do whatever she directed. Harold always
took the path of least resistance, so he never argued
with his Mom.
Chapter Two ? The Job
The next day, Mrs. Strokewood packed Harold a baloney
on Wonder Bread sandwich and drove him to work, since
Harold had never gotten around to learning to drive.
She kissed him on the cheek and said, "Happy birthday,
Honey. Don't' screw this up."
Harold said, "OK, Mom." But what he was really
thinking was, "Yeah, yeah, whatever," which is what
all teenagers, pantyboy-malaised or not, think
whenever a parent speaks to them.
Harold left the car and entered the store for the
first time. And looked around. And felt a twinge in
his gut. He didn't know why, but he was paying
attention, full attention to his surroundings for one
of the first times in his life. The store was immense.
One floor, but as big as a city block. Like a Home
Depot in size, but all girlie frillies.
Harold's cock was stiff. "How did that happen?" he
thought idly as he scanned the huge room. On the left
was ladies underwear ? rows and rows of bras and
panties and slips and camisoles and corsets and
teddies. In every girlish color of the rainbow. On the
right was ladies nightwear ? dozens of racks of
nighties and peignoirs of every size, shape, style and
length. The middle was for stockings. Fully-fashioned,
lace-top, patterned, fishnet, modern or traditional.
With at least 100 different garter belt styles and
colors. Not one pair of pantyhose. The back wall of
the store was lined with shoes. The highest, spikiest,
sexiest, girliest shoes on the planet.
Oh. Harold was perspiring and he didn't know why. Why
was it so hot in the store? Wasn't the air conditioner
working? Why did he have a funny feeling in his
stomach?
His eyes weren't focusing either and he was trembling.
Was he sick? He hadn't been sick before he entered the
store.
He was about to run out of the store and see if he
could catch his Mom for a ride home when Mr. Stiffman
spotted him.
"Harold! It's wonderful to see you. Welcome to my
store. Have you ever been here before? I guess not.
You seem a bit overwhelmed. That's OK. Most new
employees feel that way. Let's get your lunch in the
refrigerator and I'll get Nancy to give you a tour.
Harold hadn't said a word. He wanted to leave.
Feelings were unfamiliar to him. He rarely had
feelings and they were very scary. But he wanted to
stay too. He had never seen anything one-millionth as
exciting as Stiffman's Intimate Apparel.
He gulped. Apparently, Stiffman was not put off by the
lad's reaction. Had he seen it before?
Harold believed at that point that, as a young man at
Stiffman's Intimate Apparel, he would be working on
the loading dock or something. Wearing a belt with
tools and a big ring of keys. He guessed that Nancy,
whoever she was, would take him out back and introduce
him to a burly guy named Jack or Juan, who would call
him "Bud," complain about the "idiots" who ran the
store, and make him do all the difficult work.
Not so. First there was the matter of Nancy.
Nancy.
Nancy was simply the most beautiful human being Harold
had ever seen. His throat constricted when Stiffman
introduced him to her and he was humiliated when he
couldn't speak.
Nancy took it good-naturedly, saying, "That's OK,
Harold. I get a lot of that."
Harold's eyes drank Nancy in. Long, lustrous red hair.
Emerald green minidress that barely covered her
stocking tops. Fabulous, long legs encased in silky,
black stockings. Barely-there, strappy, black, mule
sandals with an enormous spiked heel. The face of an
angel. Harold's stiffie was still teeny, but it was
hard and angry.
"I'm in charge of the sales staff, Harold," Nancy
said. "I can see that you're going to be a valuable
addition to our team."
Sales staff? Harold couldn't sell ice water during a
drought. And he didn't know anything about lingerie,
other than it made his dick hard. Where were the tool
belt and keys? And the guy who called him "Bud?"
Harold managed to squeak out a "But, I?" but Stiffman
interrupted.
"I'll leave you to Nancy now, Harold. You'll be happy
here. I guarantee it.
"Follow me, Harold," Nancy said.
Nancy gave him a tour of each department, introducing
him to magnificently feminine and beautiful sales
associate after magnificently feminine and beautiful
sales associate. Harold was reeling. How could he sell
anything with them around? Customers would avoid him
like nuclear waste. Was he the only man in sales? Was
he an affirmative action case or something?
Despite the assault on his senses, Harold noticed two
things that puzzled him deeply. First, maybe it was
the time of day or something, but Harold only saw male
customers. Second, Harold wasn't sure, but $175 for a
bra seemed like a lot. Yet, the store was packed with
customers.
When the tour was finished, Nancy asked if Harold had
any questions. In response to his first concern, Nancy
said that their clientele was mostly male because Mr.
Stiffman had built a reputation by helping men pick
out lingerie for their wives and girlfriends.
Regarding price, Nancy said, "We stock only
top-of-the-line merchandise here, Harold. Plus men are
always willing to pay top dollar for service and
consultation. Any other questions?"
Those answers sort of satisfied Harold. But there was
something odd about the whole deal.
The rest of the day, Nancy spent with Harold, teaching
him about the merchandise, showing him how to work the
cash register and computer, and filling out his
employment papers. Harold wasn't stupid, just
malaised. And the new job seemed to be breaking that
malaise up a bit.
Harold wasn't sure whether he preferred malaise to the
sensory assault he underwent at Stiffman's. Being next
to Nancy all day had him flushed and feeling a need he
never knew he had. Or so he thought. Perhaps what had
really excited Harold was the?merchandise.
From what Harold was able to observe, Stiffman's
Intimate Apparel was a very successful enterprise.
Salesgirls treated gentleman customers warmly and the
gentlemen responded very well, by purchasing armloads
of wildly expensive lingerie. The girls were all very
beautiful, but would that be enough for all those men
to open?and empty their wallets so willingly?
The last stop on the day's orientation tour with Nancy
was the panty department. Thousands of panties in
every size, style and color. Harold was feeling clammy
and his digestive system seemed to be stirring his
baloney sandwich the wrong way. Nancy was nattering on
about stock and reordering and sales technique, but
Harold could barely keep himself together.
The panties were wonderful!!!!
Being at the epicenter of world pantydom hugely
excited Harold. In ways he could hardly imagine.
He held a gauzy little black pair in his hand and felt
their silky texture. He saw the tiny red ribbons that
adorned the waistband and noted the $150 price tag.
And he quivered.
He heard his name and thought that a higher being was
telling him something. "Harold!"
Oh. It was Nancy. She had caught him daydreaming and
worse, being a little faggot who got excited by
panties. She would fire him and he would never be
allowed in this paradise again. For the first time in
his life, Harold had recognized something he did not
want to lose.
But he was wrong. Nancy was smiling. "Do you like
those, Harold?" the beautiful angel said. "They're an
excellent choice. Why don't you take them home? And
these too." Nancy was holding up a pair of
simple-but-perfect, pink, bikini panties trimmed with
white lace (only $125).
Harold froze. On the one hand, he was thrilled to be
able to take the panties home and "investigate" them.
On the other, he was humiliated to think that Nancy
would believe his first-hand thoughts were true. Did
she think he was some kind of gay little dress-up
princess? Well he wasn't, he thought.
Nancy seemed to be reading his mind. "It's OK to take
the panties home. It's part of the orientation for new
employees. We want you to be?familiar?with the
products. In fact, we recommend that you try them on.
Please take the tags off and use them as you see fit.
They're yours. We want you get an idea of what you're
selling. If you like the panties, I can fix you up
with other lingerie."
Harold shuddered at the idea of wearing panties. His
cock, which had been in major distress all day, was
sending him a signal that he didn't recognize, but he
liked very much. Still, his masculine self was obliged
to say, "But I'm a man."
Nancy smiled. "Yes, but you're a Stiffman's Intimate
Apparel sales professional too. And we expect you to
be familiar with what you sell."
Poor Harold. He took in his breath and cried out
softly. Harold didn't know what was happening to him,
but Nancy did. Nancy looked away, busying herself
folding panties as Harold shuddered through the first
orgasm of his life. The agony almost equaled the
ecstasy. He saw a bright light and walked toward it.
He had no idea what happened to him or why, but he
knew he liked it a lot.
Harold almost doubled over as spurt after sticky spurt
drenched his underpants. In a fleeting thought, he was
grateful that his mother had insisted that he wear
dark trousers that morning. She couldn't have known he
would??
Harold fought to regain his decorum. The last thing he
wanted was to appear to be a nerd to his boss, who was
also a world-class babe. Nancy seemed to be fascinated
by the prospect of rearranging the panties on a rack
several feet from where Harold was soaking his
drawers.
Harold dried his watering eyes. There was nothing he
could do about his soaked, sticky crotch except hope
it wasn't too obvious. Nancy noticed when Harold was
back among the living and said, "Let me wrap these
samples up for you, Harold. Then you can go home.
You've had a lot thrown at you today." Then she handed
him her cell phone to call his mother for a ride home.
Poor Harold did so. He thanked Nancy for the
"samples," then rode home with his Mom, answering her
questions with the usual grunts. When they got home,
he hurried to his room and locked the door. It was
time to examine the samples.
Chapter Three ? Sampling
For the first time that he could remember, Harold was
truly excited about something. So excited that he
couldn't decide whether he should first clean up the
mess he made in his trousers or devour his panty
treasures with his eyes.
Harold's curiosity about what had happened in his
pants won out. He stripped off his trousers and threw
them on the bedroom floor. He looked at his
underpants. Beige, thick stains covered the front of
his Jockey briefs. How curious, he would have said if
his name were Alice. He hooked his thumb in the front
of his briefs and pulled the elastic forward, giving
him a full view of his little, drooping cock. His
pubic area was drenched with a sticky fluid that
matted his hairs and made his cock look slick. He
reached in and felt himself. Harold knew the mess was
what other teens called "cum," but until that day, he
hadn't given it much thought. Harold rubbed his wet,
sticky cock with the fingers of his right hand.
Surprisingly, it felt very good. Exploring some more,
he combed his fingers through the wet pubic hairs,
then reached down to see if his balls were wet. They
were. And the act of rubbing his cum-slick fingers
against his little bag was exciting him very much.
Eager to see and experience the panties and confident
that he had done himself no harm by cumming earlier,
Harold stopped feeling himself. He did pull down his
underpants, however, becoming naked from the waist
down. He knew he would have to hand-wash his gooey
Jockeys so his Mom didn't see them, but that was for
later. For the moment, he was the consummate panty
professional, examining the merchandise so he would be
able to perform his professional tasks professionally.
Harold considered getting a washcloth and cleaning
himself off "down there," but instinctively, he knew
that there would be further messes that day. And,
perhaps that night.
Harold's fingers quivered as he opened the bag of
panties. He saw the black teasers. Ohhhh. Then he
spotted the pink ones. They were delicious too. But
then he saw?..oh. Nancy had slipped in a third pair ?
white, satin and thronged. $195! Had Nancy said he
could take the tags off and do whatever he wanted with
them? She had.
It's safe to say that at that moment, Harold had never
been so excited in his life.
He arranged the three pairs of panties on his bed,
pink, black, white, left to right.
They beckoned him.
His cocklet had pushed through the nest of sticky,
matted hairs and straightened itself again. His balls
were aching. What was happening to him?
Nevertheless, he made his decision. The black panties
were going on first. Right after he took off his shirt
and got naked.
Harold didn't have a full-length mirror in his room.
Above his dresser, he had sort of a half-length one
that his Mom had insisted he have. Had he looked in a
full-length mirror, Harold would have seen a fine,
potentially girlish body. Slender, with slim hips and
good, shapely legs. A fine bottom that was plump in
the cheeks and tight in the middle. A general absence
of body hair. Long, straight, naturally blond hair
tied into a ponytail. Lovely, dark, large nipples that
would later be the object of many men's affection. But
at that moment, Harold didn't even look at himself. He
was fixed on the black, bikini, see-through panties
with tiny red ribbons along the waistband and leg
holes.
Carefully, he removed the tags. So expensive, yet the
men in the store were making them fly off the shelves.
Tags off, the panties were in their natural state. And
so was Harold ? naked and as rampant as anyone with a
three-inch dick could be.
Harold held the panties in front of him and felt their
cool caress on his naked popsy. Ohhh. He felt a thrill
of sexual pleasure. What would happen when he put them
on?
Harold removed the panties out of "harm's way," away
from their friction upon his prick, before "that
thing" happened again. But he just HAD to try them on.
He sat on his bed and, for some reason, pointed his
toes as he slipped his right foot through the opening
in the pretty panties. Then he slid the left foot in.
Harold's legs were practically hairless, which made
the voyage of the panties from his ankles to his
privates and bottom a very smooth ride. Harold
shivered as the wispy black treasures passed his
thighs. He looked down at the waistband front's six
tiny, red roses as the center two rosettes tenderly
scraped the sensitive skin of his little ballbag.
Ohhhh.
Pressing on, Harold eased his first panties to the top
of his scrotum, then along the short, but tender
length of his red, fiercely throbbing prick. With one
ecstatic pull, he encased his bottom, prick and balls
in gauzy, silky elegance.
Harold breathed deeply, closing his eyes and trying to
regain some measure of self-control. When he had
calmed a bit, he crossed the room to his mirror.
Harold was drawn to his own image. A pretty boy in
black panties. The panties were so sheer that he could
see his erect penis, which was so red and hot that it
was almost burning a hole in the panties. He turned
his back to the mirror and saw his pink bottom through
the black gauze of the sweet knickers.
Harold's life was divided into the times before and
after that moment.
He knew that things would never be the same for him.
Thank goodness!!!
Looking at his own bottom had him frantic with
excitement. If he just petted his cock a little, maybe
that would help. Harold kept his eyes on the mirror's
lovely rectal reflection and softly slid his
fingertips up and down the gossamer material covering
his drippy, mushroom head.
An image flashed through Harold's head. Someone else,
of undetermined origin and gender, a dream person, was
stroking his penis through his panties. It felt
wonderful!!! Then, in a flash of insight unparalleled
in most lives, Harold realized that, any time he
wanted, he could put on panties and, with little
effort, find someone who would be more than willing to
stroke his penis. And kiss him. Willingly. All day if
necessary.
And that thought made him gasp, then cum until his
beautiful first panties were filled with hot, sticky
goo.
Harold's toes curled. His pretty nipples erected and
he saw colors he didn't know existed. He saw himself
as a sexual being for the first time in his life. And
suddenly, his life was ablaze in possibilities.
As was his penis. His panties were simply DRENCHED
with hot, sticky juices and, wouldn't you know it, his
mother was banging on his door telling Harold that
dinner was ready.
Harold croaked out, "I'll be there in five minutes,
Mom," in a throaty, sexy voice he never knew he had.
Had Mom noticed?
Harold was breathing in little gasps as he put his
thumbs in the panties' waistband and slowly eased them
over his spent prick and balls and down to mid-thigh.
He considered his pubic area. What a gooey mess! What
a wonderful mess. Globs of cum stuck to everything.
The beginning of a journey Harold was eager, for once
in his life, to take.
Hurriedly, Harold stripped off his panties and went to
the private bathroom connected to his bedroom. With a
soft washcloth permeated with warm water and soap, he
gently cleaned his prick and balls. Oh, he was getting
stiff again, just from that. After dinner, he would
put the pink panties on and see where that took him.
Harold filled his sink with warm water and soapsuds
and lovingly hand washed his black panties. The cum
seemed to be dispersed easily, but where would he hide
the wet frillies from Mom's nosy eyes? Under his bed
wasn't a great solution, but it would do. He dressed
quickly and joined his Mom for dinner.
Mom seemed to notice that Harold was a bit flushed. Or
maybe she didn't. She asked her boy some questions
about his day at work and, shockingly, he gave her
some answers. Already things were better, Mrs.
Strokewood thought.
Harold was a bit surprised when Mom said, "Mr.
Stiffman is a wonderful man. And so handsome. Don't
you think he's handsome, Harold?"
"Why would Mom ask that?" Harold thought. "Does she
think I'm gay or something?"
His reply to Mom was, "I guess." But then he began to
think that Mom was right. Mr. Stiffman was handsome.
Harold blamed Mom when, after dinner, he put on the
pink panties, lay in his bed rubbing himself and came
four times thinking not only about how beautiful Nancy
was, but also about how handsome Mr. Stiffman was.
Chapter Four ? First Day in Sales
Harold awoke the next morning in pink panties that
were stiff with multiple cums. He rushed around
cleaning up the evidence, hoping that the black and
pink teasers would be dry for his "pleasure" that
evening after work.
Harold was apprehensive about being discovered when he
slipped the white pair on to wear under his boy
khakis. But no one would know he was wearing them.
Right? And he just couldn't bring himself to wear
men's underwear that day.
Mom drove Harold to work and she was pleased to see
how eager he was to get inside the store.
Harold put his meat loaf sandwich with ketchup on
white bread into the refrigerator in the break room,
then reported to Nancy for his first real day of work.
Since he had taken panties home the night before, he
assumed he would be working in that department. But
Nancy had other ideas.
"Did you have a good evening, Harold?" Nancy asked, as
they walked to the stockings and garter belt
department.
Was that a little smirk on Nancy's gorgeous face?
Harold said he had checked out the panties as she had
asked him to do. Then he thought he saw that smirk
again.
"You'll like the stockings department, Harold. Jane is
in charge and her sales are fantastic. As I told you
yesterday, we don't work on commission, but Mr.
Stiffman gives big rewards to the best producers."
Harold shuddered at the thought of a "big reward" from
Mr. Stiffman. What was happening to him?
Nancy introduced Harold to Jane, who was another
absolute feminine knockout. No wonder men shop here,
Harold thought. And he was partly right.
Jane was sweet too. During the half hour before the
doors opened at 10, she patiently explained the
various merchandise to Harold. Then things got
interesting.
Jane said, "Our top-of-the-line brand of fully
fashioned stockings is called "Girlish Dreams. It's
our house brand and you can see that the name and logo
are at the top of each stocking."
Harold could indeed see because Jane had lifted her
skirts to expose her stocking tops, garters and
panties to Harold's stunned gaze. He looked away, but
Jane giggled and said, "Don't be squeamish, Harold.
Take a good look at what you'll be selling."
Harold looked. He saw a set of long, perfect legs,
encased in the silkiest tan stockings he had ever
seen. He saw a long seam along the back of each
stocking, ending in a reinforced heel. The toe was
reinforced as well and each dainty foot, with its
perfectly polished and painted toenails was enclosed
in a black, five-inch-stiletto-heel sandal mule. He
saw white, creamy, hairless thighs bisected by slim,
black garter straps. And he saw opaque, pink panties
that looked odd to him for a reason his mind couldn't
grasp.
Harold took a long, good look. Then he looked at Jane
and gulped, "Thank you. I see what you mean."
Jane smiled and lowered her skirts. "Wear this for the
next few days, Harold," she said, handing him a badge
that said, "Trainee." "We don't want the customers to
be confused. Speaking of customers, the doors are
opening. You stay with me today and I'll show you the
ropes."
Harold thought that Jane had shown Harold quite enough
already, but he did exactly as he was told. He WANTED
this job like he had never wanted anything in his
life.
At 10:10, Jane said, "That Asian gentleman is Mr.
Hung. He's a Stiffman's Gold Card customer working his
way to Platinum."
Gold? Platinum? Nancy hadn't told him anything about
that.
Harold watched Mr. Hung pick out several pairs of $150
stockings. Over his arm, he also had a $395 black
babydoll nightie and two $175 garter belts.
At 10:22, he brought his selections to Jane, who
smiled brightly and greeted him. "It's wonderful to
see you, Mr. Hung. You haven't been in the store in a
whole week. We missed you. I missed you."
There was a thin layer of sweat on Mr. Hung's upper
lip as Jane continued. "This is Harold, Mr. Hung. He's
our new sales trainee."
Harold felt very strange when Mr. Hung looked at him.
As if he were appraising him somehow. It wasn't
unpleasant. Just strange.
Then Mr. Hung said, "Very nice. Welcome to Stiffman's,
Harold. Very nice."
What did "very nice" mean?
Anyway, Jane said, "So, do you have some things picked
out for your girlfriend, Mr. Hung? She's a very lucky
girl. Isn't it wonderful that we're exactly the same
size?"
Mr. Hung smiled. "Yes, wonderful. Can you try these on
for me now?'
What? Harold did a double take. He wanted Jane to
model the lingerie he was thinking about buying for
his girlfriend? Was that done?
Yes, but, with a few important differences from most
retail operations.
Jane took Mr. Hung's purchases and said, "These are
some lovely choices, sir. Let's just ring these up,
shall we?"
Another double take for Harold. Pay for them before
Jane tried them on and modeled them? With a strict "no
returns or exchanges" policy posted prominently all
over the store? Huh?
Jane and Mr. Hung appeared to know the drill. "That'll
be $1,938.60, with tax, sir," she said. Hung handed
her his platinum Amex, then said, a little sheepishly,
"May I purchase the panties and stockings you're
wearing now too?"
Jane smiled a "you naughty boy" smile, then said, "Of
course, Mr. Hung. Let me just add that to your total.
Oh, Mr. Hung. Just $2,848.96 and you'll be a
Stiffman's Platinum Club member. Won't that be
wonderful? I hope you'll remember little old me."
Mr. Hung was smiling broadly at the thought.
When Jane had rung Mr. Hung's purchases up, she asked
him to sit down. She stood across from him, out of
Harold's direct view, then lifted her skirts and
pulled down her panties, giving Mr. Hung an excellent
look, Harold imagined, at her pussy. She handed Mr.
Hung her pink panties, still warm from her body. He
accepted them as if they were the crown jewels. Then
she unhooked her garters and slowly rolled her
exquisite stockings down as Mr. Hung held Jane's
panties to his nose and deeply and unashamedly
breathed in their aroma. That didn't gross out Jane at
all. In fact, when she handed Mr. Hung her stockings,
she gave him a little kiss on the cheek. Then she
grabbed his purchases and took them to the dressing
room to in preparation for a show worthy of his status
as a Stiffman's Gold Card member.
Harold watched discretely, but with fascination as Mr.
Hung again smelled the crotch of Jane's panties, then
the feet of her stockings. The poor perv was so stiff
in the crotch area, Harold wondered if Mr. Hung's
trousers were made out of some rubber alloy.
Within moments, Jane emerged wearing the black
babydoll, a pair of the panties and a pair of the
fully-fashioned stockings. She was so sexy that Harold
thought that he and Mr. Hung would be riding in the
same 9-1-1 van to the hospital.
For the first time, Harold noticed that there were
large boxes of Kleenex next to all the seats in the
store. Mr. Hung was well aware that they were there,
because the customer's stiff, appreciative cock had
made its way through his fly and was standing bare and
proud as he watched Jane model.
Mr. Hung stroked himself softly, not wanting to cum
until Jane had tried on all of his purchases. Harold
watched the appreciative customer stop and take deep
breaths several times as Jane turned this way and that
for him in his new purchases. Jane announced when she
was wearing the last outfit, so Mr. Hung began to
stroke himself in earnest, assisted by a sweet,
tonguey kiss from Jane, who touched Mr. Hung only on
the lips and tongue and only with her lips and tongue
(befitting, as it turned out, Gold Card status). When
he blew his goo all over the nightie Jane was wearing,
Jane didn't mind at all. Harold wondered how Mr.
Hung's girlfriend would like getting a new nightie
that had been creamed on. But then Harold thought,
"Hey, maybe there is no girlfriend." Maybe not.
Jane scooted to the dressing room, letting Mr. Hung
clean up his mess and put his big boy back in his
pants. They had hardly noticed that Harold was there.
But Harold was processing what he had seen.
Mind whirring.
Figuring out.
What did it mean to him?
The first thing it meant was pain. The stiffest and
most painful erection he could imagine.
The second thing was sexual fear. Would they want him
to do things like that for customers? Wearing girl
clothes and kissing big, manly customers? Harold
already adored panties and was thinking about cumming
into his black and pink friends that night. But how
could he, a man, show himself in public like that? And
how could he kiss a man? With tongue?
The third thing he felt was fear for his job. The
worst thing that could happen to him would be to lose
the job that had given him the only reason to live he
had ever felt. But, as a man, he knew he could never
measure up in job performance to the set of 50+
ultrababes who worked at Stiffman's Intimate Apparel.
Out of the corner of his eye, Harold saw Jane kiss Mr.
Hung goodbye, hand him his big shopping bag and
approach Harold. He thought she was going to ask him
for his reaction to what he had just witnessed.
Instead, Jane said, "Let me show you the dressing
rooms, Harold. Follow me."
Numbly, Harold complied. He noticed that Jane was
carrying packages of black and tan, fully-fashioned
stockings, as well as a ruffled, black garter belt. He
also noticed that the dressing rooms were unlike any
he had seen at a store.
Each dressing room was soundproof and had a double
bed, two wing chairs, a nightstand, a large closet,
and an adjoining full bath with shower.
Jane led Harold into Dressing Room Three, leaving the
door open as she said, "You need to try the
merchandise, Harold. Take your pants off." She began
to open the package of black stockings.
Harold shook with fear. He couldn't remove his
trousers in front of this beautiful woman! But even
worse, he was wearing those white panties and she
would??..
"Come on, Harold. Don't be afraid. I know you're
probably wearing panties. It's OK. You're just
learning the job. Now I don't have time to waste,
because the noon rush will be in and you need relief
desperately."
Relief? Ohhh. Harold was distressed and blushed
fiercely, but he removed his pants. "What Jane must
think of me!" he thought. "Wearing white panties and
my tiny, unmanly dick is stiff and dripping."
The panty issue was short-lived, because Jane insisted
he remove his panties too, thereby permanently and
totally humiliating him. And darned near completely
emasculating him as well.
Which, as we know, can be a good thing.
Jane said, "You poor boy. I thought you were in this
condition. Why didn't you say something? No one can
work like this. Now come over here."
Jane sat in a wing chair and Harold stood in front of
her. She turned him so that he was perpendicular to
her, then she began to make him quite happy.
"You should never allow yourself to stay in this
condition, Sweetie," Jane said. "A young man like you
needs regular milking." To prove her point, Jane began
to feel and cuddle Harold's privates with her right
hand. Harold whimpered ? something he could never
recall doing before. Jane began to rub the drippy goo
all around his pretty pink mushroom. "You could injure
yourself. Does that feel good?"
Harold moaned.
Jane stroked Harold's pricktip sweetly for about five
minutes and then, with a tiny, unmanly squeak, Harold
began to ejaculate into a Kleenex Jane had positioned
perfectly to catch the young man's sticky cream.
Harold was in heaven. He was orgasming while engaged
with another person for the first time. And it was a
job benefit.
Who needed a dental plan anyway?
Harold's face was flushed and his demeanor compliant
when Jane had him sit in a chair. She instructed him
in the proper wearing of stockings, including the
sexy, teasing ways of rolling them up while a man is
watching. "Why do I need to know that?" Harold
wondered. But he did as he was told.
It put the poor, overloaded lad "on the verge" again.
Rolling on, wearing and admiring one's own stockings
constitute a sensual feast. And Harold was being
nourished for the first time in his life. When he
donned his garter belt and hooked the six straps to
his stockings. Harold was needy and whimpering once
again.
That time, he needed no encouragement when Jane
offered relief.
Jane made things extra sweet by taking things a little
further. As she caressed his tiny pole with her right
hand, Jane wet the middle and index fingers of her
left hand with her saliva and gently inserted the
manicured digits, one at a time, into Harold's tight
bottom.
Jane didn't even get to run her fingers in and out of
Harold's pootie. The first anal visitors of his life
threw him into a high elliptical orbit and made him
cry out girlishly as he evacuated the boyish toxins
from his body, awakening him to a whole new set of
possibilities.
Harold loved cumming. He loved the tingles he got when
sexual activity began. He loved the excitement of the
acts themselves, the dirtiness of it all. He was
flattered that another person would see him as worthy
for a partner, especially one as dishy as Jane. He
loved the warning pangs when his crisis was near,
followed by the near-death experience of a
full-throttle cum. The French call cumming, le petit
mort, or the little death. And they would know about
stuff like that.
What Harold didn't like was the way the events of the
past two days seemed to be affecting his masculinity.
Wearing panties and stockings, practically cumming
just from putting them on, then cumming for real when
he rubbed himself up a little while wearing girlie
things. Those were unsettling to Harold's sense of
masculinity. Even worse, he had sort of decided that
he wanted to wear stockings and panties 24/7 for the
rest of his life. Even in the shower.
That couldn't be a good sign that he would be the next
big action hero after Arnold, Bruce and Sly were in
the nursing home.
Then there was the matter of squealing when he came.
Another bad omen. Real men don't squeal and cum in
their panties, letting it dribble down onto their
fully-fashioned stockings. Do they?
Still, even though it was emasculating, he had REALLY
enjoyed every millisecond of what had happened to him
thus far.
And he had a feeling that it was only the beginning.
While Harold was in his reverie, Jane wiped up his
gooies and pulled his panties up. "I hope you're
feeling better now, Honey. Don't you dare let yourself
get so agitated without relief again. Just let me or
one of the other girls know if you need a milking and
they'll do it cheerfully and very skillfully. Now, get
your pants back up, Harold. We have customers and
there's lots more for you to learn about sales."
Submissively, Harold pulled his pants and panties up
and over his stockings and followed Jane back onto the
floor. The silky material of his stockings caressed
his legs. The panties gently scraped his prickhead and
balls. So far, he loved his job.
Harold watched Jane flirt and tease and sell a ton of
merchandise to the lunchtime crowd, none of whom had
achieved gold or platinum status yet. Jane and Harold
took a late lunch, at 1:30, and returned to the floor
by 2.
At 2:20, Harold met his first Platinum Club member ?
Mr. Rammer.
Jane treated Mr. Rammer as if he had just landed on
the deck of a carrier and declared the quest for the
perfect panty over. Mr. Rammer was clearly a VIP at
Stiffman's Intimate Apparel, and he was gracing Jane
with his purchases that day.
Harold was fascinated.
Mr. Rammer had a shopping cart filled with stockings,
panties, garter belts, high-heeled shoes and
"sleep"wear. Rammer was clearly a high roller.
Jane rang up his purchases (in excess of $4,000) then
introduced Mr. Rammer to Harold.
Mr. Rammer looked Harold over very carefully, much as
Mr. Hung had. But more as if he "owned" Harold or
something. Harold shivered with an unknown emotion
that he later understood to be sexual attraction to a
man. The whole idea was so foreign to Harold that when
it entered his head, his brain rejected it. But not
his prick. His prick liked being looked over "that
way" by a man.
Jane seemed to be wavering about something. Harold
didn't know what it was. Mr. Rammer did.
"Bring your trainee along, Jane," Mr. Rammer said.
"He'll learn something about sales."
Even Harold knew at that point that they weren't going
to be in the back room discussing lingerie fashion
trends.
He wanted to be there when whatever would happen would
happen.
Harold carried the just-purchased lingerie, following
Jane and Mr. Rammer to Dressing Room Five, which was
an even nicer version of the room where, before lunch,
Jane had made him cum and squeal ? twice.
Jane felt she had to explain a bit of what was
happening to Harold, so she did. Mr. Rammer seemed
amused as she said, "Mr. Rammer is a Platinum Card
member, Harold. That means he gets to "test drive" his
new lingerie. Gold Card members get to see it on the
salesgirl and they get a nice kiss as they're ready to
cum. But the test drive is much more?extensive. For
one thing, the member gets to watch the girl undress
and put the clothes on. The rest, I think you'll
figure out."
Harold was shaking visibly and he felt the beginnings
of a cold sweat. He was going to see beautiful Jane
naked? And so was that Rammer guy? Oh no. That feeling
of intense need was back and Jane was too "occupied"
to do anything about it.
Rammer said, "Try these first, Sweetheart," and he
handed Jane a beautiful, wispy pair of pink panties
with white lace. Suddenly, Rammer and Jane seemed to
forget Harold was in the room.
Jane did an exquisite strip tease for Rammer (and
almost made poor Harold, the innocent bystander,
explode and implode simultaneously). Jane stripped to
just her bra and panties. At that point, Rammer
removed his pants and underpants, exposing a thick,
wet, hard, muscular cock almost eight inches long and
fiercely erect. Harold's throat went dry. But that
wasn't the highlight of the interlude.
Rammer sat in a wing chair and considered the
beautiful Jane. She was slowly, teasingly removing the
tags from the panties Rammer had designated as her
first costume. Poor Harold could have used a case of
smelling salts.
Jane turned her back to Rammer and Harold, unhooked
her bra, and then teasingly turned around.
The bra had been filled with forms! Jane was
completely flat-chested, except for some lovely, puffy
nipples that were erect with her girlish excitement.
Rammer didn't appear to be disappointed at all. In
fact, it seemed to be exactly what he expected.
But then came the really big surprise.
Jane turned her back again, this time to remove her
only remaining garment ? the black panties Jane had
put on after Mr. Hung bought the pretty things she had
worn to work. Poor Harold was trembling as his mentor
wiggled out of her pretty panties, revealing a bottom
far beyond the dreams of mortal man. It was a perfect,
heart shape, firm but promising soft delights. Harold
thought, "Omigosh, she's going to turn and I'm going
to see her pussy.'
Harold was only right about the turning part.
The beauteous Jane turned and Harold saw?.her cock!
Her cock!
Jane had a cock. Just like Harold's except, perhaps
even smaller. With a pretty, girlish bag of pearls
dangling saucily below.
Harold cried out and Jane and Rammer turned their
heads toward him. Harold was scared and humiliated.
And full of apologies.
"I'm sorry, I didn't know," he said to first Rammer,
then Jane.
Rammer looked at Jane, who nodded in confirmation to
Rammer, who smiled at the thought.
Then the two went back to ignoring Harold. Jane
slipped on the pink dazzlers Rammer had bought, then
sissied over to his naked lap. The two entered into a
deep kiss and Jane placed her soft hand on Rammer's
huge cock. Harold was biting his lip to avoid crying
out again, trying desperately to process what was
going on.
Rammer's cock was leaking sticky fluid as the couple
broke the kiss. Rammer drew the almost-naked Jane to
him, then kissing licking and sucking her right
nipple.
Harold couldn't help it. He made the tiniest whimper
and Rammer stopped sucking.
Would Rammer complain to Stiffman and have Harold
fired? Tears formed in Harold's eyes at the thought.
Apparently, Rammer had other intentions. He reached
over and grabbed a pair of purchased black panties and
held them out to Harold. "I have another knee and
plenty of panties, little one," he said in invitation.
Harold gasped. He was being invited to strip nude, put
on a fresh pair of panties and then sit on a naked
man's hairy thigh. A rampant, naked man, upon whose
other naked thigh rested a panties-only-clad
co-worker, just revealed to Harold as a male wearing
women's clothes. And "pretending" to be a woman.
Pretending very well, actually. She was gorgeous. So
many things to process and understand. Were some other
saleswomen at Stiffman's really "pretty boys?" Were
they all pretty boys?
Questions for later. At the moment, Harold had to
decide whether he wanted a man kissing him and
stroking his little popsy.
Harold was certain that he wanted that very much. He
didn't know why. But he knew.
So he stood and, as the amorous, kissing, caressing
and licking couple resumed their affections, Harold
stripped naked.
Harold was afraid, but resolute. When he was
completely naked, he realized that Rammer and Jane had
stopped their fun and were looking at him. Rammer
looked as if he were very attracted to Harold, who
remembered from his mirror examinations the evening
before that he had a body made for panties.
Harold blushed, but he was flattered too as he rushed
to get the replacement panties on.
Jane's make-up was smeared and she seemed very heated
up when Harold caught her eye. She smiled and nodded
at Harold, giving him some needed affirmation.
Harold sighed deeply, then sat his pantied bottom on
Rammer's hairy, right thigh.
"You're very pretty," Rammer said. Then he kissed
Harold deeply.
Holy, wet tongue! Harold loved that kiss. The first
kiss of his life. And it was a man who was kissing
him.
Was Rammer gay? Was Jane? Was Harold? Did it matter?
Harold listened to himself. He knew that he wanted
men. He knew that, like Jane, he wasn't a man. He
couldn't define himself yet, but he knew who and what
he was.
And he knew he liked the feelings he was getting as
Rammer held his naked torso and kissed his face, neck
and shoulders.
Where was Jane?
Oh.
Harold saw that Jane was on her knees between Rammer's
legs. She had Rammer's big cockhead in her mouth and
she was giving it a good polishing with her wet
tongue.
Would Harold have to do that as part of the job? He
hoped so.
Ohhh. Rammer's right hand was caressing Harold's back
and his left hand had entered the front of Harold's
panties. Rammer's huge hand was cuddling Harold's
prick and balls as their tongues dueled.
Harold was totally enraptured. He held his head back
and surrendered completely to Mr. Rammer's lust. The
man was a great kisser. Harold was so excited and
needy. Rammer's big hand was so gentle and loving.
Rammer was so excited by Jane's tongue on his cock.
Involuntarily, Harold arched his back, squeaked and
began to spurt his cream into Rammer's hand, drenching
his panties in his ecstasy. Rammer kissed Harold and
then grunted, launching his own, debilitating orgasm.
Jane's face took rope after rope of the Platinum Card
holder's hot man juice. Jane, like any self-respecting
pantyboy, wore her facial frosting with pride.
Harold was in love. With Rammer. With Jane. With
Nancy. With his life from that moment on.
And well he should be.
Chapter Five ? Judy at Last
After their little m?nage a three-way, Harold looked
to Jane for direction.
She sweetly told Harold to get dressed in his boy
clothes (with the enchanting addition of panties,
garter belt and stockings) and get back to the floor,
since their department needed staffing. She also
whispered to Harold that she was pleased with his
development, but she needed some quality "sales" time
with Mr. Rammer.
Harold wasn't sure what he should do about the
cum-drenched panties he was wearing until Rammer
reached his hand out and said, "I'll have those,
Sweetie. Just as they are."
Oh my. Mr. Rammer certainly had his appetites! Harold
pulled his cummy panties down, exposing his naked
charms to Rammer and Jane. He blushed fiercely, hoping
they would draw him into their naughty business once
again.
Alas, Rammer was completely focused on Jane, whom he
was kissing and feeling up with some relish. He seemed
to be delighted at the prospect of some time alone
with Jane, whom he was to "entertain" that day until
just before closing time at six.
Out on the floor, Harold was visited by Nancy, who
said she had been "signaled" by Jane, who had given
her a very good report on Harold.
Harold looked critically at the beauteous sales chief.
Was Nancy a man? Harold was too much of a gentleman to
ask, though the gentleman part of him was withering
quickly.
Then Nancy cleared some things up for the girlish boy.
"We all started out like you, Harold. May I call you
Judy, which is Stiffman's name for you? He names us
all, once we accept our femininity. Recruits us all
too. The man's a genius at spotting pantyboys."
"So that's what I am," Harold/Judy thought. "A
pantyboy." He/she liked that name. And the name
"Judy."
"May we call you Judy?" Nancy asked again.
"Oh yes, please," Judy said.
Harold had had nothing going for him. Judy would have
the world at her feet. The men in the world at least.
Nancy told Judy that for the next few days, her work
time would be split between working on the sales floor
and learning how to project her feminine self to the
world ? hair, make-up, clothes, manners, voice. The
morning would begin with a makeover and the day, and
every day, would offer all the milkings she needed to
calm herself.
Nancy added, "This will be your last night as a boy,
but maybe this will make it easier." And she handed
Judy a bag filled with clothes and "other things."
Judy did what girls do when they're happy. She cried.
Starting the next day, she would be one of the girls.
Taking care of customers. Making money for Stiffman.
And for herself.
It sounded wonderful to Judy, whose personality was
developing along a completely different path from
Harold's. Judy was happy and optimistic. And chatty.
And eager to please. Especially men .
Ninety minutes later, when her Mom picked Judy up,
Judy was hesitant to tell Mom that her son had become
her daughter. Forever.
She saw Mom's car in the parking lot and scurried
over. She got inside and said, "Oh, Mom, I have so
much to tell you. I?.."
Mom was crying. She reached out her arms, hugged Judy
and said, "Oh, Judy! I'm so happy! I'm so happy that
you're happy! Stiffman called and told me everything!"
Judy was stunned and delighted. She added a tributary
to the river of happy tears. For the first time in
many years, mother and child loved each other
completely.
They yakked like girlfriends and didn't even eat their
macaroni and cheese dinner until nearly 8:30.
Then Mom said, "I'll clean up, Dear. I imagine you
have 'needs' to take care of."
Judy blushed. Had Stiffman told Mom to expect that
Judy would be "milking" herself as well?
Oh, well. There wasn't much Judy wanted to hide from
Mom at that point, but she still locked her bedroom
door.
For the first time, Judy opened the bag of femmy
goodies that Nancy had given her.
Oh, such lovely things! Three pretty nighties. Eight
delicious pairs of panties. Four garter belts and six
pairs of fully-fashioned stockings.
And at the bottom of the bag, a wrapped package that
said, "Open me when you're dressed."
What could that be?
Judy washed herself up and sat to tinkle. Then she
walked around the room as sissily as she could manage.
Make-up was not in her playbook yet, but she did pick
out and put on the sexiest pink stockings, garters,
panties and babydoll.
Oh, what a babydoll! Judy's first nightie reminded her
of a strawberry ice cream soda. All pink and white and
frothy. Her little clitty was so hard and needy just
looking at herself, but when she started imagining a
man in her bedroom with her, admiring her, then
kissing her all over like Mr. Rammer did! Ohhhh. The
poor pantyboy was "on the verge" again.
Then she remembered the package. Harold thought
packages were stupid. But Judy decided she liked
packages. So she opened it. How curious. It was a
magazine in a brown wrapper that said, "Open me first,
read me, then open the rest." The other stuff was
wrapped in a second package.
Hmmm! Judy decided to play along.
Then she noted that one item was already unwrapped ? a
tube of personal lubricant. Even Judy knew what that
was for.
Judy took the book and the lubricant and lay on her
back on her bed. Was it porn? To some, perhaps. To
others it's a book of dreams.
Judy peeled off the wrapper and saw her future.
It was a glossy, 80-page publication called "Panty
Boy." The "P" in the logo had a single pair of pink
panties draped over it. The issue was Volume 4, Number
11: April 1-15, 2001. The cover photo was a stunner!
A lovely panty boy was wearing an ensemble of white
lingerie that would have cost almost $1,000 at
Stiffman's. She was made up to bedroom-seduction
perfection, and lying on her back atop a frilly, girly
bed. Her delicious, red, bee-stung lips were parted
and her darkly made-up eyes were closed. Her adorable
panties, made entirely of the sheerest, white lace,
were down to mid-thigh and her itsy-bitsy popsy was in
mid-cum. Her perfect tummy was a lake of hot, sticky
cream, and the photographer had captured her last,
curly, gooey, string of cum in mid-air. He had also
captured the panty angel's expression of tortured
ecstasy as her "pink purse" emptied its girlish
contents for the "reader's" delight.
Poor Judy! Like ten million regular "readers" of Panty
Boy magazine, Judy discovered that no one could gaze
upon that picture for the first time and keep his or
her cum in its bag.
The sweet angel heaved her cummy load from her little
balls, soaking yet another pair of expensive panties.
She whimpered and moaned as she thought about the men
who would look at that picture and lose their manly,
liquid cargo. At that moment, Judy formed the intent
to grace the cover of "Panty Boy" magazine someday.
Which, as we all know she did. OK, twice. To my once.
But mine was a lot better. All the men I take to bed
say so.
Anyway, Judy's little nutsies almost blew off and she
hadn't even opened the magazine or used the lube yet.
The lube turned out to be superfluous, because, after
the first cumstorm of the evening, there was plenty of
moisture to go around.
When Judy had calmed herself a bit, she looked at the
cover picture again. The magazine's sissy doll was
doing something extra naughty. In her right hand, she
was holding one end of a long (two feet, at least)
cylindrical object that was made out of clear,
gelatinous, and firm-yet-supple material. Judy looked
closely. The end she could see appeared to be shaped
like a cockhead! She couldn't see the other
side because it appeared to have been pushed into the
pantyboy's pretty bottomhole! Judy gasped! How was
that possible?
Judy remembered fondly how Jane had put two fingers
into her bottom earlier that day. It had been
delightful and it made her cum hard. But Jane's
fingers were slim and that "thing" appeared to be
about the size of Mr. Rammer's cock!
Maybe it was an illusion. Maybe it was only in her
bottom a little bit. Did men put their things into
pantyboys "back there?" Did it hurt? Did the pantyboys
like it?
Aside from being terrified that she would be halved by
an overenthusiastic lover who wanted to run his
business in and out of her "dirty place," Judy was
very excited by the idea. Pantyboys could be fucked
like women! On their backs with their men rutting and
grunting. Surrendering to their men.
Oh.
She was stiff again.
Judy opened the magazine. The first "pictorial" was
called "Your Cheatin' Heart." Yes, it was a Hank
Williams song, but it was an odd name for a pictorial.
It was a story in pictures, beginning with a young man
who was a college student, sitting in class, then
going home to an apartment no college student could
afford.
Slowly, lovingly, the pictorial showed the transition
from 18-year-old male student, to the dazzling
pantyboy depicted on the cover. Picture by picture, it
showed him strip to a lovely nude, then sit at a
vanity table and make himself up into a pantyboy the
magazine called Anne. Even nude, Anne oozed
femininity. The first full-frontal shot where a
stockinged, heeled and gartered Anne is hooking on a
white, lacy bra, the reader could see the girl's tiny
tinkler. It looked erect and needy to Judy, who was
finding that she was attracted to her sister
pantyboys, though not nearly as much was she was to
men.
Judy, who had yet to suck a cock, ached to do so.
Anne dressed completely in a white lingerie ensemble.
Judy thought that Anne must be about to "entertain" a
man, since it seemed like a lot of trouble to do all
that for oneself (notwithstanding the fact that Judy
was guilty of that, less the make-up, that evening).
But Anne seemed to be meeting another friend. A
plastic one. The huge, long cock-substitute from the
cover photo appeared and Anne took it to bed with her.
After carefully lubing seven inches of one end, Anne
gave clear evidence of the disappearance of all seven
inches.
Judy's eyes were wide as she saw Anne take the entire
business with ease. No, beyond ease. With relish.
Could Judy do that? With a man's real cock?
The next six photos showed the gut-busting orgasm
depicted on the cover, spurt by cummy spurt. Then Judy
added four thick spurts of her own. Thank goodness she
had removed her panties. They were already at maximum
permeation.
Judy's head was filled with visions of real men with
real cocks putting them into her ? to their mutual
delight. If it didn't kill her first.
Judy moved on through the magazine. After the monster
cum, the phone rang and dialogue was added to the
story. Using a "split screen," Anne was on the left
and a strikingly handsome and manly fellow was on the
right. The man was in what was obviously a hotel room.
He was wearing blue silk pajamas, but had fully
unbuttoned the top, revealing a hairy chest and
six-pack abs. He had unbuttoned the crotch of the
pajama bottoms to reveal ? oh my ? a painfully erect
cock that went up to and PAST his belly button. His
hairy balls were almost the size of a brown lunch bag.
And he was seriously CUTE!
Whew! Judy was erect again. "Shouldn't this magazine
come with a warning label?" she thought.
The panty princess in the magazine asked, "When are
you coming home, darling? I miss you so much."
The man said, "Day after tomorrow, Honey. I miss you
too, Baby. I love you so much. All I can think about
is making love to you."
The two engaged in some mild phone sex for two pages
and then, "Wham!" Anne spurted her cream all over
herself, as she professed her undying love for "Brad."
Then Brad winced and flung man-sized globs of thick
juice all over himself. Judy, of course, joined them.
If she could only meet someone half as cute as Brad,
she thought. (Later, when she did her first shoot for
Panty Boy, she and Brad had a white-hot, little,
three-week affair. So did I. He was great, but Judy
and I knew we could do better.)
The picture story concluded with a lot of phone kisses
and promises. Anne hung up the phone and the full page
went back to pictures of her. She removed the big toy
from her bottom and threw it away. She held her arms
open and?..[turn the page], was joined by a very
good-looking, very naked gentleman who climbed atop
Mount Anne, hoisted her legs and gave her what
pantyboys crave. A good, stiff fucking! Judy wondered,
where did that "Brad pinch hitter" come from? Did Anne
have men lined up around the block, waiting to fuck
her should the opportunity arose? Apparently so. And
how did she get mystery man's huge cock into that tiny
hole. And why was she cumming all over herself as he
fucked her?
Questions that Judy was pretty sure she would enjoy
answering as soon as possible.
She turned the page and saw that Brad was also a
cheater! A tasty little Asian doll with a stiff,
two-and-a-half-inch popsy, a lovely smile, miniscule
black babydoll, and black, fully-fashioned stockings
had joined Brad on the bed. In the next picture, she
was kissing him and her petite bottom had consumed the
entirety of Brad's fat friend.
How was that possible?
If she could do it, couldn't Judy?
The other package!
Judy got out of bed, drooling cum down her belly as
she crossed the room to retrieve the package from the
box. It was flat and long. Judy opened it and saw ? a
replica of the two-foot-long, dual-headed, prick-like
toy from the magazine.
She could lube it up and slowly insert it into her
tight, pantyboy-virgin pussy. Just to see if it fit.
Sort of a science project.
What if it didn't fit? Judy would be drummed out of
pantyboydom. Her panties would be confiscated and she
would have to wear cotton Jockey briefs for the rest
of her miserable, manly life.
Maybe not, but Judy knew she would feel a lot better
if she could get about five inches or so of that
sissypleaser into her pootie.
Judy was trembling a bit when she washed the whole,
big sausage in the sink, with soap and water. One must
take some precautions with what one sticks into one's
"special place." She dried her imminent deflowerer
with a towel, then took the "instrument," the tube of
lube, and "Panty Boy" to bed, placing them at her side
after she lay down on her back.
Judy set up the pillows just as she liked them. Her
room had to look its best for the crime-scene photos
and the nightly news: "Pantyboy halves self with
ridiculously long, ersatz cock ? film at 10."
Judy lubed about six inches of the end with the
smaller "cockhead." Then she opened the magazine to
check out the positioning and grip Anne used to impale
herself.
She placed the intruder at the wrinkled gate to
heaven, drew her breath in, then eased the head past
the tight ring.
Not bad.
Kind of nice.
She pushed in an inch and gasped a little. A little
discomfort, no pain.
Another inch. A big pinch. The first real
unpleasantness. Judy rested. Her cock, which had
drooped from her fear, was starting to twitch in
appreciation.
Slowly, Judy pushed with steady pressure, embedding
the other three lubed inches. That hurt a bit, but it
passed. Judy held the other end of the penile
simulator and decided to do her own test drive. She
pushed and pulled the hard-gelatin material in, out
and sideways, simulating a good fuck as well as one
can without a man in the room.
That, she liked. So did her pricklet. It stiffened.
Her breathing quickened. She closed her eyes and
pretended that a man like Brad was on top of her
girlish body, pushing and grunting as he worshipped
and adored her. She was close. Her dream man was
close. Her dream man cried out! Judy screamed! Loudly
and shrilly. But her sticky juices didn't come out.
Had she broken something down there? She was in sexual
distress but wasn't cumming. Where was ?..ahhhh?..the
big thing in her bottom, rubbing on her prostate, had
delayed the juices. But hadn't abated them. All of a
sudden, the impediment collapsed and her cum was
gushing as Judy doubled over in sweet anguish.
Actually, in one way, the timing was perfect. Judy's
mother, who responded to Judy's orgasmic scream,
thinking that she was being murdered, flung the door
open just in time to see her "son" in full pink
lingerie, anus stuffed with a cock-like device,
gushing cum from a tiny, stiff prick.
We all need material to tell our psychoanalysts. Why
should we bore them?
Chapter Six ? Employee relations
Judy's career and the "real' part of her life began in
earnest the next day.
Mom kissed the still-boy-dressed Judy as she dropped
her off at work. Judy had no regrets about the fact
that she had put on boys' clothes for the last time
that morning. When the boy clothes came off, the whole
lot was going to charity.
Judy was tingling with excitement and curiosity. How
would she look after the makeover? Would she be up to
Stiffman's Intimate Apparel standards?
Oh yes, ladies and gentlemen.
Stiffman's ran a beauty parlor operation for its
"girls." Open two hours before work and four hours
after, it was an employee benefit that had a direct
impact on how many customers came through the door and
how much they spent. So it was a first-class
operation.
Delma, one of Stiffman's ace beauticians, was on
overtime duty (during Stiffman's retail hours) to do a
makeover for Judy, the new girl. Delma gave Judy "the
works" and instructed her in how to do her make-up and
touch up her new, blonde hairstyle. It took five
hours, but the results were spectacular.
Judy herself was astounded at her girlish beauty. She
was made-up, manicured, pedicured, ear-pierced,
powdered, perfumed and dressed in a perfect little
black dress that highlighted her body's assets. Judy
could only manage two-inch heels at that point, but
they still made her bottom begin to jut out the way
men adore.
When Judy stepped out on the floor, even her coworkers
stopped what they were doing to admire Judy's beauty.
I'm not exaggerating. Only four gi