Joe turned and looked in the mirror. By now, he had grown accustomed to
how he looked with the wig. His short hair looked strange, and sort of exotic.
He touched his cheek, feeling the softness. His hand then went to his breast.
He cupped it, as if estimating its weight, then squeezed it slightly. The hand
then continued lower, and he carefully felt his pubic area through the dress.

“I really do look like a girl, don’t I?” He said, turning to look at
Linda. “I just checked, and I guess I feel like one now too. I don’t have
any choice in the matter, but that’s what I am. If tomorrow, next month, or
next year they tell me I can go back, then I’ll have a difficult decision to
make. Till then I guess this person in the mirror is what I am.”
GET MORE THAI TRANNY HOTTIES AT LADYBOY 69
“And I’ll help you.” Linda said. “However you want to handle it, I’ll
help you.”

“Should I wear this tomorrow?” Joe asked. “Can I wear it to get a hair
cut?”

“You can if you want to.” Linda said. “It’ll probably take less than an
hour.”

Joe thought about Sally’s…all the women just sitting
around…talking…gossiping…about god knows what. If they even suspected
that he was really a guy…a rooster in the hen-house…he could imagine the
disturbance it would create. Of course, there is no way he would be
detected…he may not always know precisely how to act like a woman, but
nobody could ever get him confused with a man. Not unless he told them. And
even then it’s doubtful they’d believe him.

The next day was Saturday. Dennis got up at dawn and was already possessed
by the question of what he would wear on his mall spree. He also had to get
out of the house without seeing his father. Around nine o’clock his mother
knocked on the door and delivered his breakfast. “You okay, honey?” she said.
He turned to her and smiled. “Yes, I guess. I’m supposed to go to the mall
today with Debby.”
“That’s great!” she said. “What are you going to . . .”
“I don’t know.”
“What’s wrong with jeans and a sweater?”
“Mom!” he said with exasperation, “It’s not what I’m going to wear. It’s
wearing a bra and stuff out there,” Dennis said. He turned his head to the
window, creating a curvy cameo against the blue sky. His mother put her arm
around his waist.
“It’ll be fine. No one will ever suspect.”
He spun out of her grasp. “No will ever suspect what?” he demanded.
She stepped back in alarm for a brief moment. Then regaining her composure
she said deliberately, “That you’re not a girl.”
“Even though I look like one?”
“Yes, a very lovely girl,” she added.
Tears welled up in his eyes and he said, “I’m scared, mommy.” She hugged
him.
“I know, honey. I know. It’ll be fine. Everything will be fine.”
An hour later the door opened and Dennis emerged like a shy butterfly. He
wore his old jean jacket over a tight black turtleneck sweater and a pair of
girls’ jeans that Debby had brought him. The jeans were so tight that the
outline of the credit card his mother gave him was clearly visible in his back
pocket. Furthermore, his sweater accentuated his bust in a way that both
embarrassed and excited him. His mother had brushed his hair out and pulled it
back in a ponytail, tying it up high on his head in a more feminine way.
Dennis protested but secretly he liked the way it made him look cute and
little girl-like.
They drove to the mall in silence. Dennis looked out the window and played
with the end of his ponytail. When they arrived his mother said, “You’ll be
fine. Try to have fun with it.” Dennis made an effort to smile. She watched
him walk across the parking lot, losing track of him as he blended into a
crowd of teenage girls headed for the mall.

Dennis arrived at the appointed meeting place early and sat down on a bench to
wait. His breasts felt bigger and more conspicuous than ever and he
unconsciously began to hunch over to hide his curvy, new figure. When he saw
Debby walking across the mall he straightened up a little.
“Hi,” Debby said quietly.
“Hi.”
“You look great.”
“Thanks.” He blushed. “Everything feels so . . . tight.”
“That’s because it is, dear. And that’s why we’re here. Are you ready?”
“Not really.”
“Come on, let’s go get you a bra that fits.” She pulled him up off the
bench and they headed off to the lingerie department at Dillards.
Debby took Dennis back to the dressing rooms, and said, “Wait here. I’ll be
back.”
He sat down and fidgeted, trying not to feel like this was the oddest thing
he’d ever done, trying not to listen to the sounds of dressing dropping and
bras hooking.
Soon Debby returned with several bras, slips and even a garter belt. When
Dennis rolled his eyes she said, “You might like it, you know. Now take off
your sweater.”
He spent the rest of the afternoon taking off his clothes and trying on
others. Debby was having a great time selecting things and then having him
model them for her. Soon he forgot who he was and where he was and began to
look forward to trying on the pretty blouses and skirts that Debby handed him.
By two o’clock he had discarded the turtleneck and jeans and was wearing
black tights, a black denim skirt and a white blouse with puffed sleeves and a
plunging neckline. By three o’clock he had replaced his mother’s low pumps
with a pair of shiny black heels and he carried a small brown leather purse.
He felt more at ease in his new role now and even a little proud of his
figure which Debby never stopped praising. “You’re such a fox,” she’d say or
with mock envy “You’re so stacked. I wish I had your figure.” Dennis couldn’t
help grinning when he heard these compliments. Even though he felt comfortable
walking along side Debby in his new skirt and blouse, he found it difficult to
take the larger step of enjoying his femininity. Debbie sensed that this
shyness might be shed if he could see his feminine loveliness reflected, not
in a mirror but in the eyes of his beholders.
“How about a makeover?” she suggested as they strolled through the cosmetic
section. Dennis hesitated and then thought why not. Moments later an
attractive young redhead in a cream colored lab coat was daubing bright colors
on his cheek and speaking in low soothing tones about contrast and shade.
Dennis found himself enjoying the attention. Especially when Carole the
cosmetician praised his cheekbones or his aquiline nose. When she finished he
swooned at the luscious girl who stared back at him in the circular mirror.
Carole had uncovered or rather created a glittering creature with her brushes
and paint and Dennis was amazed at this new level of transformation. He was
barely begun to admire himself when Debbie said, “Let’s get your hair done
now.”
Dennis went pale beneath his blusher. “Oh, I don’t know. Can’t I just leave
it the way it is.”
“Your hair is lovely but it needs to be trained. Just like your breasts
need a bra for support, your hair needs to be . . . tamed.”
“Tamed how?”
“You’ll see. Come on,” she said, taking him by the arm and leading him into
Hair Designs.
When he left the salon an hour and a half later the ambisextrous pony tail
was gone but you couldn’t really call what replaced it tame. The hairdresser,
obviously delighted to get her hands on Dennis’s thick, abundant hair, had
taken this raw rapunzel and worked his hair into a frothy bouffant. Parted on
one side it now sinuously fell over his face in a dramatic cascade which
culminated at his shoulders in a thick, bouncing wave.
Dennis was mortified when he saw what had been done to him. Debby couldn’t
stop laughing. He looked as though he should be wrapped in ermine and carrying
a chihuahua, a soap opera vixen at a supermarket opening. It was the worst
possible outcome: big, starlet hair which called attention to his burgeoning
femininity. In fact, it was the perfect complement to his glamorous makeover
and a small part of his girlish self was celebrating. The rest of him found
his new look, like his pouffy coif, to be an unwieldy burden, top heavy with
sex.
“You look faaabulous,” Debby said over and over in her best Fernando Lamas
ooze. People were staring at him. He could feel heads turning as he walked
past. And when they reached a knot of teenage boys his composure, already on
shaky ground, completely abandoned him and suddenly he was a teenage girl,
giggling with nervous energy, embarrassed and proud of his beauty, knowing and
innocent. It was as though he’d been handed a scepter that had compelling
power but he had no idea how to control it. And so he passed through the
crowded mall causing small whirlwinds of sexual confusion in his wake.
The two girls made their way out into the silent twilight and fell silent
themselves. Dennis felt his nipples stiffen in the October chill. He drew the
jean jacket tighter.
“How are you going to get all this stuff home?” Debby said finally.
“I guess I should call my mom but I don’t really want to.”
“Why not?”
“I don’t know. She’s never seen me like this.”
“Yeah. Well, I could call my mom, I guess.”
“Does she know?”
“Not exactly.”
“What’s that supposed to mean?”
“She knows.”
“Oh, great.”
“Hey, it’s not a big deal.”
Dennis exhaled a bitter laugh. “Okay, well let’s go call her.”

Debby’s mother was not discreet. She gawked, she stared, even her silence
was uncomfortably intrusive and Dennis was glad when they dropped him off at
home. He gathered up all his purchases and went up the walk. His mother opened
the door.
“Is that you?”
“Yes,” Dennis said, bowing his head so that his bounteous hair shrouded his
face in shadow.
“Let me take a look at you. Oh my God!” She reached out to hug him but he
pulled away. “What’s the matter, honey?”
He ran past her up the stairs to his room. When he got there he was shocked
to find the room had been transformed. Gone were the beige curtains, the brown
bedspread and the dresser he’d had since childhood. In their place, were pink
draperies, a chenille bedspread and a vanity replete with a tableful of
cosmetics. A long, rectangular mirror encircled by tiny bulbs completed the
picture. A note was taped on the mirror. It read: “For our new daughter, Mom
and Dad.”
Dennis didn’t know whether to laugh or cry. He did neither. Instead the
girl in the mirror beckoned. Finally alone, she demanded his undivided
attention. The androgynous jean jacket fell to the floor like a discarded husk
and her delicate hands covered her decolletage. It was a gesture of
instinctive modesty. Head tipped forward in shy retreat of her own loveliness,
hair spilling over her naked shoulders, she resembled a little girl
simultaneously chastened and adored for wearing Mommy’s good blouse. A
mischievous smile now overtook her diffidence and she swiveled in a three
quarter turn to see just how big her hair was in back and how much space her
breasts displaced in profile. The small smile turned big as she took note of
her own womanly grandiosity. Hands went to hips next and back arched, trailing
her mane down to her waist. The little girl had disappeared. A starlet was
emerging.
“Dennis!” his mother called from behind him.
He wheeled around and felt the free fall of his hair over one shoulder. The
little girl suddenly returned, blushing crimson.
“Are you okay, honey?” she said, unable to conceal an amused smile.
Dennis looked down. His mother gave him hug and it crossed his mind that
his breasts were bigger than her’s. “I’m so proud of you,” she said softly.
Dennis pushed her away.
“Let’s see what you got,” she said, trying to break the tension.
“Maybe later. I think I’d like to be alone.”
“Don’t you want to show your dad . . .”
“No!”
“Dennis, you’ve got to face him sometime. You can’t hide up here for the
rest of your life.”
His glittering eyes flickered with a laser beam of hatred and his mother
beat a hasty retreat. He locked the door, stripped his clothes off and looked
at his body in the full-length mirror his parents had installed on the back of
his door. His body was a conundrum with its voluptuous curves and a big cock
swaying between his legs. He touched it. Not with the manly intent of his pre-
girl years but daintily, gingerly, as though it were a foreign part of his
body, an incongruous artifact of a forgotten time. Amazingly, it sprang to
life in his delicate hand and the sight of his nodding tool in concert with
his swaying breasts aroused him. He began to play with his image in the
mirror. Legs spread and pelvis thrust out, he proffered his stiff rod with one
hand and gathered up a shock of brunette hair with the other while his lips
pouted with babydoll insouciance. It was an arresting image and one filled
with coarse sensuality. Suddenly a wave of enormous shame mingled with a
knowledge of raw, unbridled power swept over him and he lay down on the pink
bedspread to catch his breath. His head was swimming with strange hormonal
drumbeats and even though the blood drained from his cock, his mind retained
the image of the lusty androgyne for a long time after.
“Dinner’s ready, hon,” his mom called out from behind the door.
Dennis stood up and turned to look at himself once again. A strange and
mischievous smile overtook his mouth and he picked up his bra and twirled it
around his finger. Then he put the bra and panties back on, tucking his
maleness demurely between his legs. Pawing through the bags from the mall he
selected the tightest jeans and a red sweater with pearl buttons that
celebrated his new convexity to stunning effect. For shoes he chose a pair of
black heels with ankle straps. Glancing in the mirror he smiled at his kitten-
with-a-whip look, freshened up his lipstick, brushed his bounteous hair over
his shoulders and bounced down the stairs to dinner.
His mother raised an eyebrow as he plopped into his customary seat. He
smiled back at her, spreading his napkin over his lap with careful good little
girl aplomb. When his father finally emerged from his own hiding place he
turned white at the image of his son, whom he had last seen in uncomfortable
transition, as a red lipped little hussy flaunting her breasts like Lana
Turner.
“What’s the matter, Dad?” Dennis said in a breathy, Marilynesque whisper.
“I thought you wanted this,” he said, resting his hands modestly over his
breasts.
His father struggled with his emotions for a moment and then sat silently,
a frozen smile fixed on his face.
“Dennis went . . .”
“I’m Denise now, Mom.”
She nodded in his direction. “Denise went to the mall today.”
“Oh,” his father said, trying to seem interested.
“He . . . she bought all kinds of stuff . . . on your credit card.”
“Oh.”
They ate in silence. Denise watched them carefully. They didn’t look up
once for 10 minutes.
“Look! My nipples are hard,” Denise finally said, nonchalantly breaking the
silence. “What causes that, I wonder?” he said, throwing his shoulders back to
emphasize his bust. His parents looked up for a moment and then down
immediately at their plates. He toyed with a strand of spaghetti for a long
moment and then said, “Look, I’m a girl now. You’d better get used to it
because I have.” He got up suddenly and went back to his room.
“What was that all about?” his father said.
“I don’t know,” his mother said.
“Maybe you’d better go see if he’s . . . she’s alright.”
“Why don’t you. I think that little performance was for your benefit.”
“What do I say?”
“Just accept her.”
“But she’s so . . . whory.”
“Have you looked around lately? That’s the way girls are these days.”
“It’s hard to adjust to him that way.”
“Her. And you’ll just have to try.”
He got up and walked slowly up the stairs.
“Denise, uh sorry, Denise,” he called out. When no response came, he tried
the doorknob and finding it unlocked he opened the door a crack and poked his
head in. Denise was sitting at his new vanity. The sweater and jeans were
gone. He wore only a black brassiere, panties and heels. His hair was piled up
on his head casually in Gibson girl splendor. He turned to look at his father.
In his hand he held a mascara brush. “Hi, Daddy,” he said with a coy smile.
His father eyes dropped to Denise’s expansive cleavage and he withdrew
hastily. “Sorry, I thought you were . . .”
“Dressed,” Denise finished. “But, Daddy, I am.”
Hiding behind the door, his father grew purple with embarrassment and rage.
“Listen, Daddy, I’m not what I was. Physically or any other way. I’m your
little girl now with not so little breasts. And I’m pretty and I like it. So
you better get used to me this way because I’m not changing back again.”
Slowly the door closed and Denise smiled into the mirror for a moment before
resuming the brush strokes of his mascara.

* * *

On Sunday Denise went over to Debbie’s and the two spent the entire afternoon
trying on clothes and making up. He was an avid student, absorbing as much
information as he could about make up, clothes and hair. Debbie was surprised
at the new lack of self-consciousness about his femaleness. Though late in the
afternoon, as Debbie fussed over his hair, he admitted that he was worried
about school.
“Why?”
“Why? I left there six weeks ago as a boy and now I returning with this?”
he said, pointing to the the frothy pile of curls atop his head. “And these,”
he said, cupping his breasts.
“But everyone knows something happened to you.”
“They do?”
“Well, yes. I mean, it was happening before you left, you know.”
“What are they saying about me?”
Debbie stopped teasing his hair for a moment. Their eyes met in the mirror.
“They’re saying you’re a girl now, a beautiful girl.”
“How do they know that though?”
“I told them,” Debbie blurted out.
“What did you say?”
“I said that your body had changed and that you and your parents decided it
was best if you started wearing . . . girls’ clothes for a while.”
Debbie’s matter of factness made Denise blush.
“And I said that you were really pretty.”
Denise sighed, his bosom heaving beneath his blouse. “Do you really think
I’m pretty, Debbie?”
“Shut up, big tits and let me finish your hair.”
“I hate that word.”
“What? Tits?”
“Yes. Do you really think my breasts are big?”
“Oh, you just want to hear me say it. Yes, of course they’re big. 36 C cup
is big, darling. The boys are going to love you.”
Denise looked up at the mirror. “No, they won’t. They’ll think, ‘He’s a boy
who looks like a girl.’”
“How long do you think that will last?”
“Well, I’m not a complete girl, you know.”
“They won’t be seeing that though, will they. And besides how will they
know it’s still there?”
Denise smiled at his reflection. “It’s kind of like being a spy. Like Mata
Hari,” he said, covering his face like a veil with a thick coil of brunette
curls. Debbie casually recaptured them and resumed brushing.
“At least you won’t have to take P.E. anymore.”

* * *

The next day Denise and his parents met with the school counselor, Mr. Belson
and the school nurse, Miss Ashley, to talk about “Denise’s” return to school.
Denise wore a long sleeve ribbed knit dress that revealed the contours of his
new topography with such drama that Mr. Belson had trouble looking at the
statuesque young tart without staring in awe. It pleased Denise no end to see
that the slightest shifts in his posture reverberated throughout Mr. Belson’s
libido like tiny seismic disturbances.
“Denise seems to be adjusting to her new role very well,” Mr. Belson said,
looking first at Denise’s father who shifted uncomfortably in his seat and
then at his mother who beamed with pride at her son’s beauty and finally at
Denise himself whose demure lips opened and seemed to Mr. Belson to mouth the
words, “Fuck me.” Belson turned crimson and then said, “Well, I guess that’s
it unless you have anything else, Miss Ashley.”
“I’m just wondering what bathroom Denise will use,” Miss Ashley said matter
of factly.
“Well, I, uh,” Belson stumbled.
“Why can’t he use the girls’ bathroom?” Denise’s mother asked impatiently.
“She could but I’m afraid of what would happen if she was . . .
indiscreet,” Miss Ashley said, politely correcting his mother’s slip.
“Denise is a lady,” his mother insisted. His father winced.
“Well, I’m sure she is but some of the students know that Denise is not . .
. completely feminine. I would hate to put her in an awkward position.”
“Why don’t we try it for a while and see how it goes,” Mr. Belson
intervened.
Miss Ashley sighed and retreated. The meeting was over.
That night Denise stared at the ceiling and thought about Mr. Belson. “How
nervous he was. He couldn’t take his eyes off my breasts. I controlled him
just by touching my hair or shifting in my chair. These are powerful,” he
thought to himself as he cupped his heavy bosom in his hands. He decided to
experiment more with his new powers and when he appeared at the breakfast
table in the morning, his clothes were even more provocative. He wore an
ultratight v-neck red sweater and designer jeans which left nothing to the
imagination. He hair was tied high up on his head and bounced merrily against
his back in a thick spring-loaded ponytail. His adorable bangs belied his
tantalizing couture. He chose the brightest red lipstick he could find and his
alabaster cheeks were brushed dramatically with pale rose blush. He was ready
to turn heads.
First class was English with Mr. Bostick. The usual preclass din was in
full sway until he appeared in the doorway. Then the heads not only turned,
jaws dropped and tongues fell out as the prettiest boy in school took his old
seat. He waited for Mr. Bostick to make a speech about his return and it
seemed as though that might have been the teacher’s plan until he’d seen the
statuesque boy’s transformation. He was literally speechless before such a
bewitching metamorphosis. Denise breathed a sigh of relief (an event followed
by every male in the room) and felt secure in the knowledge that his imposing
beauty had helped him escape an embarrassing situation.
The rest of his classes followed a similar pattern. The few who weren’t
aware that he’d left school weeks earlier as a boy were soon apprised of the
fact and turned to stare with undisguised wonder. He smiled politely at the
girls and suggestively at the boys and basked in the reflected heat generated
by his homecoming. No one talked to him between classes and he spoke to no one
until he saw Debbie in the halls between classes.
“How’s it going?”
“Not too bad, I guess. Everyone thinks I’m a martian but I don’t care.”
“You’re too beautiful. That’s the problem. They can’t believe someone with
a set like yours was a boy a few weeks ago.”
Denise smiled. “Gotta go.”
“Bye.”
He walked down the corridor feeling the tightness of his sweater against
his breasts, the swish of his pant legs and the clicking of his heels. He felt
good. He felt alive. This feeling stopped abruptly when he pushed the heavy
door into the girls’ bathroom. A mangy quartet of tough girls fixing their
hair and makeup turned to look at him. He smiled and went into a stall and
shut the door. Like most stall doors the lock hadn’t functioned in years and
only gravity kept it shut.
They girls resumed their conversation in stage whispers.
“I don’t think he looks that great.”
“His bra’s gotta be padded.”
“I heard he still had his dick.”
“He’s probably standing over the john right now.”
“Hey, leave the seat down, will ya?” Laughter. They moved to the front of
his stall and began whispering in earnest.
“Hey, Denise.”
“What?”
“We want to see it.”
Silence.
“Come on, Denise, we’re all girls here right?”
Denise tried to move his knee against the door but it was too late. As the
door flew back he stood up hastily and made a futile effort to pull up his
jeans.
“Oh gross!”
“It’s huge!”
Denise tried to cover himself but it was too late. He burst out crying and
made the impromptu decision to cover his face rather than his privates. It was
a bad decision. One of the girls had a polaroid camera and flashed a quick
snap of the pretty girl and the unquestionably large remnant of her manhood.
“You won’t be so haughty after this gets around, Big Dick.”
“See if his tits are real,” one of the girls said. Another girl responded
by ripping Denise’s sweater open, exposing his pert 36 C cup breasts bouncing
in a lacy black brassiere.
The camera whined again capturing the conundrum of Denise’s body and her
anguish at its rude exposure. Denise took his hands from his face to scream at
his antagonists but that only served their interests better when a third
picture was snapped that showed the pretty girl with the bouncing ponytail
revealed, cock flopping and cleavage popping.
This was the picture that went into wide circulation throughout the school
the next day, reaching Mr. Belson’s desk sometime in the late afternoon. It
was a crude xerox of a xerox but Denise was still clearly recognizable.
Curiously, his look of anger had mutated in the copy machine into cartoonish
surprise giving the photo the look of a burlesque postcard, the kind where an
airbrushed cutie loses her bathrobe to an obliging gust of wind. The fact that
much more was revealed than a pair of white buns added a certain piquancy.
What remained in the viewer’s mind after the picture was gone was the
magnitude of both his male and female attributes and, of course, his stunning
face.
The next day when Mr. Belson called Denise into his office he expected a
somewhat chastened version of the vixen he’d met at the parent conference. He
was surprised to find that Denise was unrepentant. He wore a scooped-neck
leotard that exploited the fulsome beauty of his bust and a denim sheath skirt
fit tightly around his derriere. He wore his hair down and it framed his face
in soft waves of kittenish abandon. There was nothing about him that suggested
he had a secret surprise in his panties or that the humiliating events of the
past two days had daunted his hussy image.
“You don’t seem bothered by this, Denise,” he said, holding the picture up.
“I am but I can’t let it show or it will only get worse.”
“So you hide your true feelings.”
“I suppose.”
“Is that wise?”
Denise looked into his eyes. “Mr. Belson, I know I’m a girl now. I have
breasts and a girl’s figure. I also happen to have a penis. Now everyone knows
it. It’s not a big deal.”
Belson stared in awe at the lovely boy/girl’s insouciance. Then he looked
down at the key in his hand and said, “Well, I don’t think it’s wise to use
the girls’ bathrooms anymore. I’m going to give you the key to the faculty
bathroom. Do me and yourself a favor and keep the door locked from now on.”
Denise took the key and headed for the door. He turned round as he touched
the doorknob and said “Don’t worry about me, Mr. Belson. I know what I am.”
Yes, you’re a slut, Belson thought as the pretty boy/girl left.
The next few days were difficult ones for Denise as her notorious picture
circulated throughout the whole school. Taunts of “Big Dick” and “Cock Girl”
were whispered behind her back in the corridors and her old friends, including
Debbie, were embarrassed to be seen with her. She didn’t seem to mind much
during school but at night, as she sat before her vanity, she would burst into
tears when she scanned her lovely image in the mirror and saw her big cock
resting peacefully beneath her tricot panties like a python in repose.
Nevertheless she was determined not to back down and each day her
provocative clothes reflected a “Take No Prisoners” attitude that did little
to let the controversy around her subside. One day she arrived at first period
English class in a bustier and short black skirt with a bolero jacket that
mitigated her delicious cleavage but not by much.
“Denise, I’m afraid I’m going to have to ask you to go home and change,”
the principal had said after calling her into his office.
“Why?”
“I think that’s fairly obvious,” he said, uncomfortably.
“Not to me.”
“You can’t come to school dressed like Madonna and expect to get away with
it.”
“You don’t have to worry about the boys. Not one has even spoken to me
since I’ve come back to school.”
“It’s not just the boys, Denise. It’s . . . everyone,” he said, letting his
own eyes drop for a moment to savor those milk white doves cupped in black
underwired lace. “You’re here to learn not to . . . parade around in your
underwear.”
When his mother pulled up to take him home she feigned shock by his
brazenness. “Denise, you’ve got to tone down. For goodness sake, you look like
a whore,” she said laughing but Denise could tell she took great pride in his
“stop a train” figure.
When they got home he changed into a tight black sweater. “That’s better,”
she smiled. “Much more ladylike.” In fact, it was even more tantalizing than
the bustier but it didn’t get him kicked out of school.
* * *

Belson stood relieving himself in the faculty bathroom when the door lock
clicked and the knob turned. He glanced over to see Denise closing the door
behind her.
“What are you doing in here?” he yelled.
“Don’t worry, I locked the door,” she said, sidling up to him at the next
urinal and unzipping her jeans. He looked straight ahead, his face a pinkish
white as she made water next to him and the perfume of her hair filled his
nostrils.
“Am I embarrassing you, Mr. Belson?” she said huskily.
He stood silently as she studied his face. He could feel her eyes shifting
down to his cock, examining it. After what seemed like an eternity he
finished, zipped up his pants and turned toward the exit. But Denise turned
and stopped him. Her pink nailed fingers shook her big cock in his direction
“Look at it, Mr. Belson. I know you’ve wanted it since that first meeting.
Go ahead. It’s not a snake. It won’t bite.”
“Get out of my way, you little slut.”
“Look at it,” she screamed.
He glanced down.
“That’s it. Not so hard, was it? But it could be. Here, touch it.” She
reached out and grabbed his hand and placed it on the large tube of flesh. His
hand curled around it like a tendril on a vine.
He looked at her. She was never more captivating. The soft brunette hair
that framed her face, the thick bangs that fell just above her wide eyes, the
lovely innocence of her white skin belied the power of her spell, the cruel
womanliness of her demands. She was irresistible. A wave of yielding weakness
passed through him with a visible tremor and pulling her thick root like a
handle, he drew her close and kissed her lips.
As they kissed, she unzipped his pants and her hand slid through the
opening to retrieve his cock. It was hard. She was not surprised.
She pulled back and smiled at him. “Do you want me?” she asked, in a husky
babydoll whisper.
He said nothing but buried his head in her thick hair till he reached her
neck and let his tongue answer with a long kiss that made its way from her
neck to her mouth.
“Suck me, baby,” she said.
Now he pulled back and looked at her with faint apprehension. “You do what
I tell you, baby,” she said, in a soothing maternal voice.
He sank to his knees and looked up at her in helpless supplication. She
smiled down at him and hoisted her tube top and bra up over her breasts,
letting them sway above him like dark shadows. She smiled again. “Go ahead,
baby.”
She guided her big cock to his mouth and drew it across his lips a few
times before they opened and opened and opened and soon it was glistening and
gliding, in and out across his tongue, down his throat, over his lips and
back, swelling with each stroke until it threatened to choke him.
As he fell into the rhythm of the trancelike motion, Denise turned toward
the mirror and studied this strange tableau vivant. Her body now arched over
the supplicant, hands against the tiled wall, breasts spiraling over him like
heavy fruit and he below, shaking the tree by its thick trunk with drunken
abandon. The thrust of her round, white buttocks; the dark, shimmering hair
falling around her head, shaking with each lunge; the pouting, mocking lips,
the raw, redness of her glistening cock. Were these the devices that pumped
the blood to her groin or was it Belson’s unschooled lips, his untalented
tongue? No, it was her and her alone. The juicy vision of her contradictions,
the crucifying beauty of her womanly body and her red male member, the
sweetness of her face and the cruelty of her desire, the mingling of innocent
youth with ravenous lust. The puppet Belson. She smiled at the ease with which
she pulled his strings and her triumphant smile unexpectedly brought forth the
streaming, white gism that flowed out the sides of his mouth and spurted into
his damp hair and fell to the tiles in clotted, milky drops. Before the last
spunk was spilled Denise pulled away from Belson to face the mirror and
grasping her cock with both hands, she took aim at her own deliciously bawdy
image. A final shot, issuing from deep within her groin, arced and hit the
mirror, clouding the reflection of her face with hot, white cum.

–

It took four days to arrange for the movers to come and take
everything he couldn’t fit into his car. Then he went home. The
leave was less than satisfying; neither one of his parents were
supportive of his desire to stay on active duty. Anderson visited
his brother and left him the car and his personal gear (including
a fair number of firearms). He did a little bit of traveling, and
presented himself to the military air terminal at McGuire with two
weeks’ worth of leave remaining.
The Air Force sergeant who was at the receiving desk read
Anderson’s orders and then checked a file. She told Anderson to
go check into the transient BOQ and stay there; he’d be notified
when his flight was called. Anderson had taken MAC flights before,
one normally has to wait at the terminal for one’s name to move up
the waiting list. This treatment mystified him, but he just did
as she told him to.
The phone in his room rang a day and a half later. Anderson
switched on a light, picked it up and muttered his name into the
handset.
“Lieutenant Anderson? Master Sergeant Wilkes at the MAC desk.
Your flight leaves at 0430. A car will be at the Q at 0410 to pick
you up.”
“What time is it now?”
“A little after three, sir.”
“All right, thanks.” Anderson set the handset back into the
cradle. Fucking zoomies, scheduling a flight on the rev watch.
Oh, well. He rolled out of bed, shaved and showered. The desk was
open 24 hours, he was checked out by four and waiting for his ride.
An airman came over to him. “Are you LT Anderson?”
“Yes.”
“May I see your ID, sir?” Anderson handed it to him. The
airman looked it over and handed it back. “Come with me, sir.”
He led the way to a “blue steelie,” Air Force lingo for an issue
sedan. Anderson got into the right-side seat. He was a little
surprised when the airman passed by the MAC terminal and drove to
a hangar after passing a security check from the APs, who were
wearing woodland camo uniforms and carrying M-16A2s. The airman
drove out onto the ramp and up to an Air Force C-12, their version
of the Beech King Air. This one had seen better days, it was set
up as a cargo carrier (or “trash hauler”), complete with a load of
cargo. The pilot, a woman in a USAF pilot’s jumpsuit with
captain’s bars waved him on board. Anderson stowed his bag between
two crates and settled into the right seat.
“You might want to put on that headset,” she said. “This old
beast can get pretty loud.”
Anderson did so, adjusting the headset to fit and the boom
mike to almost touch his mouth. “Can you hear me?”
“Sure can.” The pilot ran through the starting procedure with
the economy of motion born of great amounts of practice. She soon
had both PT-6 engines turning. She received her IFR and taxi
clearances, then taxied out to the runway. They had to wait for
the wake of a departing C-5 to dissipate, then they were on their
way.
The flight went to Wisconsin, Anderson guessed. He could
recognize Lake Michigan and he did his best to follow along with
the air traffic controllers working the airplane. Dawn was
breaking when the pilot started her descent. There was nothing but
woods, then he saw a small town next to an airport. When they
landed, he looked with surprise at the collection of airplanes on
the ramp. He hadn’t seen so many tailwheel airplanes in one place;
everything from a few J-3s up to three Twin Beeches, a C-46 and two
DC-3s. There were a few tricycle-geared airplanes, but damn few-
- a couple Cessna 172s, a Mooney, three Bonanzas and a King Air.
Everyhting was painted in civilian schemes, complete with N-
numbers.
It looked like a civil airport in Alaska, except the man
coming out to greet them had an assault rifle slung over his
shoulder. He told Anderson to go to the line shack, then he
started talking to the pilot about refueling the C-12 and unloading
the cargo. Anderson trudged over to the shack. A woman with a no-
nonsense demeanor asked for his ID. She compared the card to a
list, then handed it over. She stuck out her hand and said:
“Welcome to school, Sherry. I’m Doris Stackpole. I’ll be your
training coordinator while you’re here at the school. Let’s get
you situated. Come with me.” Doris led the way out of the other
end of the building.
“What is this place?”
“It’s a training facility for all sorts of students. Some of
the students are training for covert ops, some are here above
board. First rule is: Don’t talk to anybody about who or what you
are or what you are here for. Everything around here runs on a
`need-to-know’ basis. Understand?”
“Sure do.” They had walked across the road to a small area
of townhouses. Doris led the way to one of them and opened the
door with a key, which she gave Anderson.
“This is yours for the duration of your stay.” She showed
Anderson around. The townhouse was on two levels; upstairs were
two bedrooms and a bathroom, downstairs was a kitchen, dining area,
living room, a study (complete with a computer with a 19″ screen)
and a half-bath. “You’re getting this place because it’s so close
to the field, most of your training is going to be in flying.”
“Which of those planes will I be flying?”
Doris shrugged. “If you complete the course, all of them.”
“Even the DC-3?”
“Yes, but you’ll have a few other things to worry about.”
Anderson didn’t like her grin, but he’d do a lot to get a DC-3 type
rating. Doris went to the door. “You have an appointment. Bring
your stuff, they’ll take it and issue you what you need.”
Anderson followed along. They walked to a building almost a
half-mile away. There they went into a room where Doris told him
to strip to his underwear. Anderson did, two women came in and
started measuring his body; one measured, the other recorded. They
traced the outlines of his hands and feet. The real surprise was
when they measured penis size, both flaccid and erect. Anderson
was embarrassed at that, but the two were just doing their job and
did it. Afterwards, Doris gave him a pink terry-cloth robe and
told him to take his underwear off. She collected all of his
things and marched out of the room.
For the first time, Anderson was scared. He had no idea where
he was, had no money, no ID, and all he had was a pink bathrobe.
Doris returned about forty minutes later with some clothes.
She handed him a pair of white cotton panties, “I think you know
how to wear them,” she said. Next was a yellow and black t-shirt,
a pair of white socks, women’s blue jeans and a pair of Reebocks
that were white with pink trim. “Other clothes will be sent to
your apartment. Now, let’s go to medical.”
“Another physical?”
“Not like one you’ve ever had before.” This time, they drove.
Doris had the keys to a jeep-like vehicle that ran on batteries.
She drove to a hospital that was a couple of miles away by road,
although it was right across the airfield.
Doris was somewhat right. It was a thorough physical; but the
difference came when they had Anderson lie down for a whole-body
CAT-scan. He almost freaked out; he had to lie on a very small
white tunnel while the machine hammered and whirred. He could have
sworn the thing was going to grind him up. After the scan, Doris
took him to the cafeteria for lunch. The food was about the same
as any other hospital, barely edible.
The PA system paged Doris when they had almost finished. She
left the table to answer it, then returned. “C’mon, Dr. Trotti
will see you now. We’ll find out what he can do for you.”
They finished quickly and left the cafeteria. Anderson wanted
to ask what was going to happen, but there were other people
around.
Dr. Trotti was in his late 40s. He shook hands and led them
into a darkened room. There was a screen on the wall and an
overhead projector that could project computer images. “Sherry,
my field is reconstructive surgery, though maybe should say
constructive surgery. Take a look at this.” He turned the screen
on.
Anderson looked closely. The image was of a woman wearing a
tank top and a skirt that came to just above the knee. Her breasts
swelled the top and showed a little cleavage. The skirt clung to
nice hips. Her face was not that of a raving beauty, but she had
nice cheekbones and didn’t look bad at all. “Who is she?”
“That’s you.”
“What?”
“Yes.” Dr. Trotti shifted to another screen. “This is your
skeletal structure..” He went into a lengthy discussion of how they
could modify Anderson’s skeletal structure to make him look like
a woman, followed by a discourse of what plastic surgery techniques
they could use. Anderson felt the MEGO (for “Mine Eyes Glaze
Over”) factor kicking in. Adding pieces here, taking pieces out
there. It wasn’t his body, it was a biological erector set.
After Trotti said his piece, Anderson asked the key question:
“How much of this is reversible?”
Dr. Trotti considered that. “Most of it is. We can change
everything back that required surgical techiques. You are going
to need a fair amount of electrolysis for us to be able to
accomplish what we need to do. That isn’t reversible.” The doctor
just smiled. Almost everyone he had worked on asked that question.
He had done the reversal surgery on about five percent of those he
had worked on. But he didn’t say anything.
“All right. When does the electrolysis start?”
“Right now,” Doris said. They said goodbye to the doctor and
went to another part of the hospital. There a nurse injected a
painkiller similar to novocaine inside his mouth. She had him lie
on a table, then after about 30 minutes, she started to work.
Another nurse came in and started on the other side of his face.
Anderson could hear the humming of the machines and the occaisional
`zap’ as a needle vaporized an oil pocket. The nurses would wipe
his face with an antiseptic every so often. He was very tired and
since he was feeling no pain, he fell asleep.
They woke him up four hours later. His lower face was wrapped
in a cold mask, it had tubing through which a chilled solution was
circulating. When they took the mask off, one of the nurses
closely inspected his face. “Not bad.” She gave him a tube of
antiseptic ointment and a small bottle of pain pills. “See you
tomorrow,” she said.
Anderson wanted to say something, but his face was numb.
Doris took him back to his townhouse. She showed him the clothes
hanging in the closet, mostly variations of what he was wearing:
jeans, different tops, several pairs of running and aerobics shoes.
There was an assortment of unisex-athletic gear.
“You get food by placing an order through your computer,
though you’ll have to cook it yourself unless you order the
microwavable dinners; I recommend them as you won’t have a lot of
time. The instructions are next to it, it’s fairly self-evident.
You can order any books, tapes, CDs or videos the same way. The
computer also ties into the training database for unclassified
material; you’ll be taught how that works starting tomorrow.
Anything you order will be placed on the living-room table, except
for perishables which will be put into your refridgerator or
freezer. There are some tapes by the VCR to start you off. I’ll
be by tomorrow at 0730. Any questions?”
Anderson made writing motions. Doris found a tablet and a
pen. “Toothbrush? Razor,” he wrote.
“Toothbrush is upstairs in the bathroom. No razor, it’s
easier to work with longish hair. See you in the morning.”
Anderson half-heartedly watched a video, then found a chicken
dinner in the freezer after his face denumbed enough to eat it.
He took a shower and rubbed the ointment over the areas where the
eletrolygists had worked. He soon fell asleep wondering waht
tomorrow would bring.
Tomorrow brought flight training. Doris took him to a
classroom next to the airport. She turned him over to an
instructor named Craig, who proceeded to start teaching him how to
fly by instruments. Classroom work was in the morning, simulator
work in the afternoon.
This routine went on for a solid month: electrolysis one day,
flight training the other. As Doris had promised, all the course
work was on a computer database, so Anderson was able to work on
the rating in the evening. The simulator gave way to an IFR-
capable Cessna 180; Anderson became able to fly an approach to
minimums and follow up with a good landing. “It’s a lot harder in
a taildragger,” Craig explained. The electrolyis was a lengthy
affair, Anderson sometimes had several techicians working on his
body: they removed all the hair from his face, the back of his
neck, his arms, legs, chest, and back. The process was always
accompanied by localized painkillers. They thinned his eyebrows
to ones that could be either masculine or feminine.

By the end of the month, Anderson had an instrument airplane
rating and the body hair of a woman.

Chapter One

As a hetersexual, who is also a secret transvestite with a raging
lingerie fetish, John’sactive sex life exists in two different dimensions,
mixing fantasy and reality. John loves women and worships their delicate
satin and lace lingerie.
None of John’s women would describe him as a hunk or stud, but all
find him to be a patient and skillful lover who attends gently to their
bodies and carefully to their sexual needs. He is slender and slight of
build, and always expresses great interest in the dress and appearance of the
women with whom he shared mutual attraction. His appreciation of their
femininity is always apparent.
It is that appreciation which provides a clue to the other John
perhaps better known as Jacqui who has a raving preoccupation with the
feminine undergarments of all women. His gentility with women is a direct
manifestation of his own frustrated femininity, relieved only when in
proximity to intimate feminine garments. Our hero(ine) is always on the
lookout for any opportunity to experience, no matter how vicariously, the
joys of sensual, sexy, feminine lingerie.
The sources of John’s arousal and satisfaction are far ranging: from
avidly reading brassiere and panty advertisements in newspapers, magazines
and catalogs, through careful but discrete observation of displays in stores,
to voyeurism, also discrete, in social situations.
John is always alert to every possible clue about the
undergarments, especially brassieres, of any women with whom he has contact.
Is there a peek at bra or breast because of the decolletage? Does a gap
between buttons reveal a glimpse of satin and lace? What can be deduced from
the bra outline traced under a blouse or sweater? Does an erect nipple
visible as it strains against bra and blouse? Is the lace trim visible
through a sheer blouse? Does the outline of the straps reveal a front
fastening bra, or a t)back?
But breasts and bras, while first in John’s interest, are not the
only thing to atrract his attention. The glimpse of a frilly slip, especially
seen because of a skirt slit or wrap*around is certain to be noticed, as is
the presence of a pantyline showing through skirts or slacks. Most entrancing
of all is the telltale outline of a garter and stocking tab indicating a
truly feminine woman wearing a garterbelt or bustier rather than pantyhose.
Each of these vicarious thrills, however, are only a prelude to
John’s transformation into Jacqui. Read on as Jacqui recounts the details
savoring her affection for each exquisite manifestation of her degenerate,
petticoated, sissy)status.
PANTIES
Nylon panties are a basic item of feminine apparel in Jacqui’s
transformation into a sissy who wants only to be treated as a sex object by
whatever woman allows him to provide her with sexual gratification. Most of
the time, however, Jacqui is not able to find a woman who can accept her as
the totally submissve transvestite that she aspires to be. Mostly, she must
rely on her own imagination and devices which are also satisfying and can
provide for long periods of intense arousal and self)release.
But, back to the details of Jacqui’s passion, starting with those
wonderful nylon briefs. Bikini panties are for cute, lithe little buns and
absolutely flat tummies. But, Jacqui must also be able to restrain her
pre)tumescent clittycock which is so easily aroused. That requires panties
with a wide crotch, not only to keep John’s ugly, hairly balls snugly
retracted in their scrotal sac, but also to keep Jacqui’s sanitary pad in
place. While a pad isn’t always necessary, there are times when it is
essential to keep from staining delicate panties. A panty liner is sufficient
to catch tiny drops of semen which may leak, in a most unlady*like
manner, from John’s naughty penis when he has been aroused for too long
without relief. Using a belt to hold a sanitary pad also helps to preserve
Jacqui’s flat profile by keeping John’s penis well contained.
BRASSIERES
As we already know, titties are at the absolute center of Jacqui’s
most exciting fantasies and so brassieres are almost her singular
preoccupation. The very sight of John’s Mistress in her bra reduces him to
begging for a feel of her wonderful globes encased in the heavy satin of her
exquiste brassiere. And, it creates an almost intolerable urge for
transformation into Jacqui as John is torn between desire and envy.
Any sight of Jacqui’s most favorite feminine garment is a thrill.
(S)he is never certain which is the more exciting, the titties or the
marvelous eroticism of that most alluring of garments, the brassiere.
Obviously a bra looks best on a slender, full) breasted woman, but John loves
to look at and study all bras.
It is always difficult for John when contempating Jacqui to decide
what was more pleasurable. wearing a bra with pretend titties or just by
itself. When wearing titties created from rice)filled nylon stocking bags
with the top knotted to created a nipple outline, there is the wonderful
tension of shoulder straps and the delightful weighted curve which feminizes
posture and shape. Without the inserts, she can caress, massage and pinch her
nipples which is also so exciting, even though they are pathetically small
even for a very flat)chested girl. Real women are so lucky to be able to
experience both sensations.
Small breasted women can wear a padded bra to increase their
contours, but only within limits because pads lack the natural shape which
makes tits so attractive. Tight blouses are revealing when breasts strain
against the fabric of the bra or the blouse to reveal the pert outline of an
erect nipple. But the effect of a loose, slightly open blouse which allows
both a peek at a lacy bra as well as revealing the breast contour is even
more erotic.
The advantage for small breasted women is that they can wear the most
delicate of bras with flimsy cups, extra lace and narrow, stretchy straps.
They also look wonderful wearing demi*bra styles with half cups on which
their delicate globes rest, nestled on a slightly padded shelf of nylon,
exposing the soft white flesh and perhaps an erect dusky nipple.
John’s ideal is a B)cup size which allows for almost any bra
selection including strapless and front closure as well as the newer y)back
back styles which he notices more frequently now as their outline is
distinctive. Jacqui recently bought one. Wearing it nicely filled with
pretend titties is delightful. It allows plently of jiggle when Jacqui walks,
but the slender straps stay nicely in place without slipping whether the cups
are filled with make)believe titties or not.
There is a problem for the she)male pretender which real girls don’t
experience. That is, without the weight of titties, bra creep can be a real
problem, especially when worn under male clothes in social situations where
weighted bra)forms can not be inserted. Then, straps can slip and the
frequent necessary adjustments create a real risk of detection of one’s
self*deception.
GARTER BELTS
Jacqui also has a red, lacy elastic garter belt which circles her
waist, just above her hips, with the garters stretched tautly over thighs and
buns, held in place by snug, satiny panties. Worn without panties, under a
slip and skirt, it allows freedom for John’s cock and balls, and access to
them for fondling. Panties are, however, usually necessary to restrain his
naughty male organ which has a tendency to bulge as a result of the
stimulation attendant to wearing feminine garments
WAIST CINCHER
John recently come yet another step toward feminization, but yet also
another step in being forced to the realization of how unfeminine a male
shape will always be. Having failed in courage on an earlier attempt, he
finally purchased a black, nylon waist cincher with stays and long black
garters.
On his first venture to the garish shop, John could only thrill to
the sight of so many pleasurable garments on display, all oriented toward
enhancement of the female form or feminization of the male. There were white
and red and black brassieres of every design and size. There were breast pads
with molded nipples.
The selection of panties was fantastic as was the array of garter
belts. There were costumes for maids and other servants, all on female models
but clearly available in larger sizes for sissy males such as Jacqui.
The clerks were all elderly and watchful but not in a threatening
way. On his first visit, John carefully examined the selection of waist
cinchers but was afraid to make a selection even though the price was modest.
On a return trip, however, he again carefully examined several with
growing but controlled excitement. Finally, John selected the one he thought
would most feminize his shape. As the clerk completed the sales slip, he
asked whether John needed stockings. John knew that he had taken another step
toward being comfortable with what he was. He felt no need to make excuses,
but only stated that he had an adequate supply of nylons.
Imagine his chagrin when, after driving home with great anticipation,
he discovered it to be too large. He clearly needed something smaller if it
was to create a properly constricted feminine feeling. It required some
resolve to go back because the sign in the store clearly stated “no returns
or exchanges.”
But, John’s needs for perfection and feminization won out. He
returned to the store, albeit with some trepidation, determined to achieve
goal. Without hesitation, John told the clerk that he had made a mistake in
the size; and that his Mistress demanded that he replace the garment with one
affording more control. John apologized, as instructed by his Mistress, for
not having tried it to be certain that it was tight enough. That was
important to remind John that becoming Jacqui required occassional public
humiliation by letting others know that he was only a sissy with a pathetic
clitty)cock trying to pass as a woman with real titties, smooth shapely legs
and round buns which deserved to be pampered in nylon and lace.

John selected a smaller size, but even though it looks and feels
snug, his Mistress has determined that if she is to tolerate this sissy who
wants to wear her clothes, he must be forced into still tighter corset
bondage. That is Jacqui’s next goal even though her black, nylon cincher gets
her very aroused when she is permitted to wear it and looks perfect with dark
nylons, pink panties and black pumps.
SLIPS
John’s Mistress has a wonderful wardrobe of petticoats all of which
fit Jacqui comfortably. Most are pettis, but she has one full-slip which is
large enough and heavenly to wear. It not only emphasizes Jacqui’s bustline,
but fits snugly over her torso as it flairs out from the waist. It delicately
swishes against Jacqui’s thighs when she walks while wearing her black
leather pumps with modest heels. It gently caresses her thighs when she sits,
especially while wearing her garter belt. And, it does cover John’s hairy,
and thus markedly unfeminine torso.
The only disappointment is that except for one very short petti,
which Jacqui adores because it is taffeta, none of Mistress’ slips are narrow
as she prefers the A-line style. Jacqui would be ecstatic to have an ankle
length straight slip which fit snugly. That would remind her to take short,
lady-like steps when she walks, and when sitting, would display her garter
belt tabs to remind Jake in another way of his feminized status.

CHAPTER 2

John and his wife had gone to a party at the home of Barbara, one
of their friends. Barbara was tall and statuesque. A very striking divorcee
who gave every indication of being eager for sexual activity. John had met
her before his marriage at a time when his finance was living in another
city. Barbara had come on strong at the time, but John hadn’t responded.

The party had gone on for several hours and most people had left when
John went upstairs to use the head. As was his habit, he quickly checked for
evidence of stray feminine undergarments which he might fondle. None were in
immediate evidence so he stepped into the bedroom and slipped open a drawer.
John had done this routine sufficiently often so that he had a sixth sense
for the location of the lingerie.

He was rewarded by the sight of satin and nylon in a profusion of
colors and styles. As he had suspected, this was a woman who pampered herself
with a delicate selection of panties and bras. As John had surmised from
hugging Barbara whenever they met, (this was always an opportunity to make a
cursory check of the type of bra being worn) there was a selection of front
and backhook bras. Most were very flimsy and delicate, and all were
underwired to support her luscious C)cup titties. Some were push*up,
demi)styles. Even better, all were in size 36, which meant that they would be
a perfect fit for Jacqui.

While the temptation to linger over this find was strong, John was
emboldened to try another drawer. Again, his desires were realized when he
found lacy slips and several garterbelts with real nylon stockings among the
pantyhose. Needless to say, John was rapidily transported into ecstasy as he
began to contemplate playing Jacqui with this treasure trove.

Unfortunately, his preoccupation was so complete that he failed to
hear footsteps coming up the stairs and into the room. His first clue was
when he heard Barbara’s husky tone saying, “Well, can I infer that you prefer
my lingerie to me? This will interest your wife and our friends.”

John could only throw himself on Barbara’s mercy, explaining about
Jacqui and begging her not to disclose his secret yearning for feminine
garments. “Very well she replied”, indicating her long held contempt for all
men which derived from her former husband’s behavior in leaving her for a
much younger woman. “I have always wanted a sissy male to serve me and you
should fit the bill nicely. I will make you sorry that you intruded into my
privacy and you can expect ample humiliation to be coming your way. I won’t
share this with your wife for now, but if you don’t follow my instructions,
you can bet your panty)clad ass she will find out about you quickly.”

“Tell your wife that you must work next Saturday and be here at 9 a.m.
Wear your bra and pink satin panties and be sure to bring along a waist
cincher, garter belt, stockings, heels and a butt plug. I will begin your
training as a humiliated sissy shemale. Don’t ever expect the pleasure of
wearing my feminine finery, although I may allow you to earn the privilege of
worshipping it as a symbol of my superior body and your weakness

Needless to say, John thought of Saturday with both fear and
anticipation, knowing that he could indulge his love of lingerie, while at
the same time he could be humiliated by this striking creature as she
feminized him still further.

Getting out of the house already wearing his bra and panties was a
problem because the bra was clearly visible through his shirt. However, he
quickly got to his car without being seen by the neighbors. On the other end,
he was not so lucky as he had to walk a distance. Of course he encountered a
group of teenaged girls who were chatting and giggling with youthful
exuberance. He could not avoid them and although it made him nervous he
wanted to see the outlines of their brassieres, even though doing so
increased his risk of exposure. How he envied their developing breasts,
swelling inside lovely lacy bras.

Barbara greeted John by demanding that he demonstrate that he was
wearing a bra and panties before she would let him enter her house. Although
John was certain that the teenaged girls could be observing him, along with
whoever else might be watching, he had no choice. He carefully raised the
front of his shirt, trying to keep the back in place until Barbara could see
the nylon and lace cups of his flimsy beige bra held snugly in place with
y)straps.

Far from being satisfied, her only comment was, “And what else are you
wearing? I want to see your pink little panties, now.” John fumbled with his
fly, but was informed that he was to open his belt and lower his trousers
before he would be allowed the safety of having the door closed behind him.
He could only comply.

Once she had him inside, Barbara instructed John to remove all of his
masculine clothing which she then locked away in a trunk. Tying his hands
behind him, she demanded that he present himself kneeling before her to
pledge obedience to her superior female titties and pussy. She demeaned his
pathetic little nipples and clitty)cock, reminding him that they were not
worthy of the nylon and lace lingerie that he so coveted. However,she
promised, in return for his devotion, to work on improving his worthiness.
John was then blind)folded and required to stand clad, only in bra,
panties and heels, without moving until Barbara returned. After a few
minutes, she returned to the room. To John’s surprise she began to rub and
squeeze his nipples. The effect on his cock was immediate. ” Shall I take
your panties down? ‘Oh yes’ “Yes is not acceptable, you will never address me
except as ‘Mistress’. “Yes Mistress, please.” John felt the panties being
slipped down to his knees. Next he felt something being tied around his erect
cock. When the blindfold was removed he saw a pink bow decorating his cock.
Almost immediately there was a flash and he realized that Barbara had taken
his picture. His erection quickly disappeared. “That, she announced, is for
documentation of your journey and as further insurance of your continued
obedience to my commands.”

Pulling his panties up tightly wedged into the crack of his ass,
Barbara untied Jacqui’s hands and directed him to don the rest of his
feminine attire. With trembling anticipation, Jacqui inserted rice)filled
nylon bags into the cups of her 36)C brassiere, carefully adjusting the
straps. The beige bra had been replaced with a black underwire with satin
cups to cover the pink balloons. Jacqui would have preferred a demi)bra, but
pushup styles don’t work well for shemales with pretend titties.

He often wore less sturdy bras which allowed his pretend titties to
jiggle, but had decided that this was likely to be a situation requiring some
restraint, especially if Mistress Barbara wanted to have him remove the bra
forms so that she could administer nipple punishment (which, of course,
Jacqui fervently hoped would be the case).

After requesting permission to remove the pink panties which Mistress
Barbara had pulled up to cover his clitty)cock, Jacqui next forced himself
into the black waist cincher to flatten his tummy and to shape his hips. He
then fastened the red nylon garterbelt around his waist. Sitting on a stool,
he drew each of his black nylons up his legs, attaching them carefully to the
garters. In front, the garters stretched tauntly down his thighs, framing his
pubic hair and flaccid cock. The back two suspenders curved over his buns.
Jacqui then stepped into black leather pumps with three inch heels.

Finally, before pulling up her snug satin panties, Jacqui squatted
down and inserted a gob of K)Y jelly, followed by a butt plug into her
puckered little asshole. Squeezing her buns together to retain the buttplug,
she stood and pulled her panties snugly over her buns. While the panties
would help to hold her plug in place, Jacqui knew that she would have to keep
her anal sphincter muscles tightly clasped around the plug and that doing so
would remind her to maintain a more feminine posture.
When Jacqui had completed that task, she pulled on a short black
half)slip which barely covered the tops of her stocking as she stood
uncomfortably before Mistress Barbara, not knowing what was next. Jacqui
hoped that her clitty)cock would behave and remain in a flaccid state. But,
she knew that eventually it would demand attention and Jacqui was
apprehensive about her Mistress’ reaction.

CHAPTER 3

“Well,” Barbara chuckled, “I can’t decide whether you look ridiculous,
pathetic or cute.” “I suppose you are a bit of each. Perhaps some make)up
would improve your appearance, but I think that will have to wait until you
earn it by taking care of my needs.”

“Now that you are all dressed)up, we’ll go outside so I can use the
remainder of this film in natural light. We do want to have an adequate
record of your progress.” John was terrified because although he knew that
the backyard was fenced, it was visible from the upstairs windows of
adjoining houses. His terror was heightened when they got outside and he
could hear voices from the next yard. But, he also knew that he had no choice
but to cooperate.

“If you want to pretend that you are a woman, I’ll want to see that
your posture and gait are feminine. I don’t want you to be an embarassment to
we genetic girls who have real titties to jiggle when we walk and long
shapely legs with well rounded buns for men to covet. Put some sway into your
walk so I can decide whether you are sexy enough to excite my lesbian
friends. Then perhaps we’ll see whether horny men notice you when I put you
on public display.”

Jaqui, of course, had often practiced walking in heels. She loved the
feel of tension in her calves when walking in heels, and adored the taut
garters snugly holding her stockings to her thighs. When Jacqui walked, the
butt plug wiggled, requiring strict attention to maintaining a tight grip
with his pretend pussy. And, he had to keep his thighs tightly clasped to
hold his clitty)cock and scrotum tucked away so that they would not create an
unsightly bulge in Jacqui’s panties. The result was short, mincing steps
which displayed an exaggerated femininity, and provided a delicate bounce to
Jacqui’s pretend titties.

“Well,” declared Barbara, “even though you walk like something is
sticking up your ass, the effect isn’t bad. Training you may not take as long
as I anticipated. If I allow you to remove your butt plug, will you still be
able to stand and walk like a sissy male doing an imitation of a real woman?”
“Yes, Mistress,” Jacqui replied. “Very well, you may remove it, but don’t
think that I’m finished with your little rosebud. If you want to have a
pretend pussy, I’m going to have to stretch your little hole so it can
accomodate my largest dildo.”

“First, I want some more pictures. Sit demurely with your ankles
crossed. Now, cross your hands across your breasts as though you were
shielding them from prying male eyes trying to undress you. Lift your slip so
I can capture your garter tabs and your bulging mound which is pretending to
be labia. Now turn around and bend down so we can see your panty covered
ass.”

“Now trot inside, remove your plug before you get too excited and get
yourself back here to me. If there is any evidence that you have relapsed and
done naughty little boy things to your pathetic excuse for a pecker while you
are out of my sight, you will be severely punished and our game will be over.
I have more plans for you and they do not include your sexual gratification
except under my control.”

Keeping her tightly puckered asshole clasped around the buttplug,
Jacqui teetered across the patio and quickly went to Barbara’s powder room.
Lowering her satin panties, and delicately lifting her slip, Jacqui expelled
the buttplug, carefully wiping her asshole so that no lubricant dripping from
her shemale pussy would stain her panties. She then pulled the panties snugly
up into her crotch so that her clitty)cock would be held tightly out of sight
and her scotal sac with its unfeminine balls retracted up into where her
pussy would be if only she had one.

Jacqui then washed her smelly plug with hot water and soap and put it
aside, wondering what was next in store. Jacqui didn’t have long to wait as
Barbara immediately summoned her with a brusque reminder that a Mistress must
never be kept waiting.

“You really are a titless, pussyless wimp who needs to be chastized
both for keeping me waiting, and for having the audacity to pretend that you
have breasts and a vagina as though you were a real woman. You aren’t
anything but a flat chested sissy shemale. Take that padding out of your bra
and get on your knees in front of me. I’ll see if you can get erect nippples
just as we ladies are expected to have when a man fondles us.”

Jacqui immediately kneeled in front of Barbara who was seated in a
lounge chair with her legs slightly spread and her miniskirt hiked up to
mid)thigh. Her creamy white thighs were visible beyond the exposed tabs of
her garters. She was wearing a gauze)like blouse through which the outline of
her sheer lacy bra and the brown circles of her nipples were noticeable.

“All little boys believe that girls titties grow from being fondled
and mauled. Do you believe that I can make your titties grow by playing with
them?” “Oh yes, Mistress, please do”, replied an ecstatic Jacqui. “You really
are a foolish twit,” replied the haughty Barbara. “You could’t fill that bra
even if you overdosed with hormones. What I will do is to make those nipples
so sensitive that you will know how it is for a woman when her breasts are
tender and distended because of the time of the month and some pig of a man
has mauled them thinking that it felt good for her. ”

“I know that is what you want, but first you must get me in the mood.
You can start by licking my thighs, above my stockings, until you have your
nose buried in my pubic hair and your tongue is licking my clitty. If you can
keep your hands to yourself, and away from yourself, you will be allowed to
suck my pussy for as long as I enjoy it. If you can get me hot enough so that
my nipples push against my bra, I’ll work on your pathetic titties until you
beg me to fuck your sissy shemale ass. Now get started.”

Jacqui was, of course, delighted at this opportunity to serve her
Mistress who already had Jacqui in an absolute state of internal arousal and
fighting hard to keep the excitement from causing her clitty to become
noticeably tumescent. She quickly began licking the inner aspect of Barbara’s
thighs. It was no time at all before Jacqui’s nose and lips were nuzzling
Barbara’s labia and tasting the moist nectar inside of her cunt. Jacqui knew,
that in spite of Barbara’s seeming indifference, she was becoming aroused
too. Not only was Barbara’s pussy getting more and more moist, but Jacqui
could sense the muscular quivers anticipatory to orgasm in a woman whose cunt
was throbbing from the attention it was receiving. There were some telltale
moans, as well.

Suddenly, however, Jacqui’s head was pushed away from that delectable
pulsing cunt so that her tongue was just out of reach of those luscious
labia, and she was gripped between Barbara’s powerful thighs. Simultaneously,
Jacqui felt Barbara’s long fingernails probing through the satiny fabric of
her bra, raking across Jacqui’s nipples. “Now, you sissy bitch,” breathed
Barbara, “you are about to experience the exquisite torment of nipple
punishment and pleasure.”

With that, Barbara pinched and rubbed Jacqui’s nipples until the
shemale was aroused almost beyond tolerance. Both Barbara and Jacqui were
wracked with great orgasmic convulsions as wave after wave of release swept
over them. The pressure of Barbara’s thighs, the taste of her pussy on
Jacqui’s lips, the stimulation of her nipples, and the gentle friction of
stockings and panties caressing her genitals were causing Jacqui to cum in
the satiny panties even though no one had touched her clitty)cock. She could
feel the sticky exudate collecting in her crotch. It was warm and wonderful,
and Jacqui knew she would still be horny after her satin panties had turned
damp and sticky.

As they both lay exhausted, Barbara reclined in her chair and Jacqui
kneeled on the ground awaiting further instruction from her Mistress. Barbara
informed Jacqui that while she had made a good start, it would be necessary
for Jacqui to exercise bettter self control during future sessions. “You may
leave now. Change into the bra you wore when you arrived, but leave those
panties on so that you will be reminded of how a woman feels when some man’s
cum is dripping from her cunt after she has been fucked. And, be back here at
9 next Saturday. I’ll have some new adventures for us. You know the rules so
dress accordingly.”

“You also have an assignment. I expect you to spend at least one hour
a day with that plug inserted deeply into your virgin asshole. I want it to
be well dilated next week for you to feel what it is like to be be on the
receiving end of a hard prick, or to wear a tampon as genetic girls must.”

“I also expect you to be wearing a training bra. You don’t deserve the
luxury of satin cups, a firm underwire and delicate lace. I saw you admiring
those teenage girls outside and I just know you were thinking about their
cute little bras and panties. I’ll bet you were wishing that your titties
were growing just like theirs. Perhaps I should invite them in to show them
how ridiculous you pathetic men are. They should be learning how to
appreciate their soft downy pussies and tender young titties which are
superior in every way to male bodies.”

“I am going to give you more nipple training. Your pathetic pretend
titties certainly need it. And one other thing, except for a sanitary belt
and napkin to keep your butt plug in place, you are forbidden to wear any
lingerie until you dress to come here next week. I don’t want you getting
aroused and wasting your cum. I have plans for every drop that you can store
between now and your next training session.”

“Oh Mistress,” pleaded Jacqui, “please don’t make me wear my bra when
I leave here. I will wear my cum filled panties, but how can I get into the
house wearing a bra without Mimi detecting it?”

“You should have thought about that before you went rummaging into my
underwear and agreed to have me give you petticoat training, you pathetic
pussy. You should be pleased that I am permitting you to wear it for a few
more minutes. Remember, its going to be a long week before you are to be
allowed the pleasure of a bra with the feeling of nylon and lace around your
tiny nipple)buds, and that will be only a flimsy teen bra and not an
exquisite creation of satin and lace which molds and caresses the breasts and
nipples of a real woman.”

“I will see you next week, and be prepared for more petticoat
training. I want those nipples and that hole ready.”

CHAPTER 4

Mimi had been asleep when John left the house that morning. He could
only hope, as he drove home, that she would be distracted when he got home
long enough for him to remove his bra and cum filled panties.

When he enterd the house, however, Mimi greated him with a smile and a
hug. “My,” she whispered as she traced her finger over the outline of his
bra, “what is this?” Jake gasped and replied, “I felt sorry that I had to
leave you this morning so I wanted to be thinking about your titties snuggled
in your bra all day since I didn’t have an opportunity to fondle them this
morning.”

Pushing John away, Mimi said softly, “Dont lie to me you sissy. You
wore this bra all day because you wanted to pretend you had luscious tits
like mine. Now drop your trousers so that I can see what you have under them.
Have you been wearing my panties again?”

John knew she suspected something so he decided to respond directly,
“You know that I’m wearing the panties that you had around your pussy and
buns yesterday, dearest.”

“I want to see them,” insisted Mimi. “I want to be certain that you
have’t stretched them with a naughty erection.”

With great trepidation, not knowing how accepting Mimi would be, John
turned around and dropped his trousers so that Mimi could see his buns but
not the damp stain in his crotch. “Turn around,” Mimi demanded.

When John didn’t respond, Mimi slapped his ass with her hand. “Barbara
called me, and I know all about your day and what led up to it. She and I
have discussed your behavior and training and I have decided to help her. I
know that you have been wearing my panties without permission and stretching
my bras by wearing them without my permission. I’ve found your cache of
undies, your heels, buttplug and fantasy articles. I want you dressed in your
sissy clothes now so that you can demonstrate what you have learned and I can
determine how best to continue your training.”

“It would be good punishment for you to follow Barbara’s orders and
not wear lingerie for a week. But, we have discussed a better arrangement.
You will remain dressed as a sissy shemale, including a plug up your ass and
a sanitary napkin, at all times in my presence. That way I can be sure that
you are punished if your clitty gets hard and you are tempted to play with
it. If you are not with me, you will wear male clothes, including baggy
cotton underpants.”
“Now,” she continued, “take off those disgusting, soiled panties and that
bra. Go to the bathroom and shave your legs and body including your balls. I
want you to trim your pubic hair so it is nice and feminine. When you have
removed all the ugly male hair that you can reach, I will inspect you and
shave your back.”

Even though he was uncertain as to where this would all lead, John was
excited and pleased, although hoping that his clitty)cock would behave. At
least he would be able to continue to wear nylon panties and bras, even
though he would have preferred real brassieres to a skimpy training bra. John
had also long secretly fantasized about shaving his legs and trimming his
pubic hair. He looked forward to smooth legs so that he could try stockings
other that the dark ones he customarily wore to hide his shapely but hairy
legs.

John quickly went to the bathroom, relieved that his secret was in the
open. Although he was somewhat apprehensive about the future, he quickly
decided that if he behaved, he could expect to be treated as a female and
would have two real women with wonderful tits and pussys and a whole new
supply of lingerie to adore. He stepped into the shower and began his
transformation.

When he had finished shaving, including his face so that he would be
smooth all over, Jacqui (for he was now feeling very feminine) shyly and
demurely called to Mimi. She inspected him carefully and pronounced her
satisfaction. Reaching into the vanity, she produced a large buttplug which
she lubricated.

“It’s time we got you accustomed to the experience of having an object
inserted into your most intimate body cavity. Real women spend almost 25 per
cent of their time wearing a tampon and are expected to accept male cocks at
other times. Since you only have one pathetic hole, it will have to serve
both functions. Until we can get you some tampons, a sanitary belt and pads
to chafe between your thighs, and a dildo for me to use on you, this will do.
Bend over so you can start to feel filled while I finish shaving you.”

Jacqui obediently bent over, gratefully accepting the plug into her
(for she was now ecstatically into her female self) puckered rosebud. She
immediately and reflexively tightened her anal muscles and squeezed the
buttplug with her buns so that it would remain in place. She then kneeled in
the hard tub while Mimi shaved the remaining hair from her back.

“Now go to the bedroom and put on the pink panties and pink training
bra that you will find there. Put on the white shorts and knit shirt and wear
the low heeled shoes I have purchased for you. Then we are going shopping to
buy sanitary supplies for you and a variety of dildoes for me to use in
converting your tight asshole into a usable cunt for Barbara and me to use at
our pleasure. We may find other uses for it as well.”
“But Mimi,” cried Jaqui, “I can’t go out that way. Everyone will see the
outline of my pink panties and bra, and what will they think of a man wearing
heels?”

“In the first place,” replied Mimi, “you will address me as Mistress,
because that is what I am. I do not intend to permit my pussy)worshipping,
sissy)slave to be on a first name basis with a superior female person.
Second, you have always enjoyed secretly observing panty and bra outlines on
real women. It is about time that you were the object of lewd and rude stares
from men and women.

“If I hear one more word of argument, you will have some cute red
polish for you fingernails and toes so that you will be even more obvious as
a sissy. To make certain that you receive enough attention, you had better
work at putting a seductive wiggle in your ass when you walk. Barbara tells
me that your are skilled at wiggling your ass especially when your are busy
trying to retain your tampon. Now get going. I am impatient to get you to the
Mall where you can be seen.”

Under Mimi’s watchful eye, Jacqui went to the bedroom where she found
the panties, bra and low heeled shoes laid out. Although she was disappointed
to see that the panties were cotton rather than nylon, they were a feminine
cut and their snug fit carerresed Jacqui’s buns. The bra was nylon. It didn’t
really have defined cups, but only simple nylon triangles held together with
thin elastic bands which Jacqui knew would not be nearly as enticing as the
underwire bra with satin cups and a wide band that she preferred. The silky
nylon did rub gently against Jacqui’s nipples which were still erect and
tender from Barbara’s earlier teasing.

Mimi sensed Jacqui’s reluctance to wear these plain garments,
commenting “You will have to earn the right to wear truly feminine
undergarments just as little girls must go through the uncertainty of waiting
to see whether their little nipple buds will grow large enough to require
sexy brassieres. Now get dressed.”

“You will need some careful training before you get into nylon, satin
and lace. We are prepared to share our female hormone pills with you. They
won’t give you wonderful titties like ours, but they will enlarge your
breasts. Better still, your nipples will become engorged and sensitive just
as ours do before our period. Then some nipple training will lead you to
appreciate a real brassiere. Perhaps you need some silicone implants.”

Jacqui dressed quickly for going out in public where everyone would
know that he was not a real woman, but a sissy*shemale as they noticed the
outline of his feminine panties and pink teen bra. Jacqui hoped that she
would soon be allowed to make a more complete female appearance with real
lingerie and makeup including nail polish and a wig.

–