Archive-author: Brenda Mccall.
Archive-title: Cassandra - Part 1
A story inspired by my first outing while fully dressed as a woman.
I'll let you wonder about what parts are true and what parts are not.
It had been exactly one year, this night, since he had
stumbled onto this place. And except for last Friday's visit - a
reconnaissance mission really - this was the first time he had
been back. He could still remember walking into the club that
fateful night 365 days ago, and how his heart was pounding with
excitement as he began to mingle with the crowd. Almost
immediately he had become aware of something very different about
these people, especially the women, although he couldn't quite
put his finger on what it was that was tugging at his mind. But
a loud comment - or was it a joke? - had ultimately forced him
into full awareness of the uniqueness of this place. And
suddenly he realized that many of the women here were not really
women at all, but were instead boys! The strangest thing of all,
however, was that for the first time in his life he suddenly knew
that he wanted to be a woman.
Because of that night, his entire life changed forever.
Secretly, he began calling himself Cassandra and started to act
like a girl whenever he was alone. In the meantime he dieted,
and exercised, and learned about being a crossdresser. He
practiced putting on makeup, shaved his legs, and grew out his
hair slightly. His only dreams were of being a girl.
Eventually, those dreams turned into fantasies, wherein men would
seduce "her" into having sex with them, and later "she" bought a
dildo so that her fantasies became closer to reality. Life had
never been so good.
But now a year had passed and Cassandra thought she was
ready for her first public appearance as a woman. And what
better time to do that than the anniversary of her accidental
discovery of Club Copa. Indeed, what better place! Now, as she
sat in her car trying to muster the courage to step out into a
different world, her mind raced over the things she had done
today to prepare for this moment. The prissying and pampering
had started the moment she had arrived home from work, and the
first thing she did was to remove every trace of unladylike hair
with a depilatory and then a razor. Afterwards she spent almost
a full hour luxuriating in a rich bubble bath while she passed
the time reading a torrid romance novel. Of course, she had
pretended she was the girl in that story, even during the love
Shortly after the dinner hour, Cassandra slipped into her
undergarments: bra, panty, garter-belt and stockings (all black)
then pranced about the apartment for a time as she conducted one
last practice session walking in her new, four-inch, black-patent
leather pumps. Her press-on nails came next, which she polished
with a very sexy ruby colored enamel while sitting on the sofa
watching television (the fashion channel) and alternatingly
crossing and uncrossing her feminine looking legs as she waited
for her nails to dry. Cassandra liked putting on her nails
before makeup because it was so much more enjoyable seeing her
pretty fingers in the mirror - especially when she was putting on
It never ceased to amaze Cassandra how fun it was putting on
makeup and how womanly she felt after doing it. This time, she
had gone all out to achieve an elegant evening look and had used
every technique she had learned over the past year to make
herself look feminine and pretty. The foundation was perfectly
matched to her facial skin, and a carefully selected blush gave
her that radiant, youthful look that she had always enjoyed
seeing in other women. Her natural blue eyes were beautifully
framed by no less than four shades of violet and gold eye
powders, properly blended of course, and were set off by the
thickest and longest mascara coated eyelashes she had ever been
able to achieve. Cheryl Tiegs would have been proud of her this
day. But by far the most enjoyable aspect of a makeover was, for
Cassandra, when she put on lipstick, in this case a shimmering
red that exactly matched her long nails. To her, that was always
the moment that marked her complete transition from male to
female - even if only in mind.
The sound of a car door slamming shut somewhere nearby
snapped Cassandra's mind back to the present, and peering through
her rear-view mirror she noticed a man a few rows back beginning
to make his way towards the club from between several parked
cars. As a diversion from her obvious nervousness, Cassandra
watched the fellow until he had disappeared around the corner of
the building. Swallowing hard, she knew it was now the time for
her own entrance.
Anxiously, Cassandra got out of the car, brushed her dress
free of wrinkles, and then began the long walk around the
building to where the main entrance of the club was located. Her
fear of being discovered made her want to turn around and go back
home, where she would be safe in the privacy of her own
apartment, but the thrill of being dressed in public and the
prospect of a new, more meaningful life kept her going. After a
few trepid moments, her steps started coming easier. And instead
of concentrating on her fear of being discovered, she was now
able to notice how wonderful it felt to be wearing a dress in the
cool night air. She felt, and barely heard, her nyloned thighs
gently swishing against one another as she walked - oh, how she
loved that - then became acutely aware of how the gentle breeze
was making the fringe of her blue silk dress dance about her
When she finally arrived at the entrance, she went up the
front steps of Club Copa with her hips swaying underneath the
smooth fabric of her lovely dress and her heels clicking
tantalizingly on the concrete. A pair of men stood outside the
front doors and stared at her luridly as she passed; one of them
said hello. But Cassandra pretended to ignore them as she
flicked her lons blonde hair back over her shoulder in a manner
that conveyed to her admirers the message that they'd have to do
better than that to get into her panties. In actuality though,
she was tremendously excited; her scarlet lips curled lustily and
her breathing almost stopped. Smiling slightly, she hoped they
were starins at her shapely ass as she strutted into the club.
She was also thinking how wonderful it must feel to have two men
pumping her full of meat - one in each of her holes.
Once inside, Cassandra walked quickly to the area she had
picked out for herself the Friday before, sat down, and put her
purse on the table. After crossins her legs and adjustins her
skirt yet another time, she looked around the club and noticed
that it was only about a third full. But if last week was any
indication she knew this place would be bopping long before
midnight ever arrived.
So far, most of the patrons were men, but to her delight she
saw four or five other exotic-lookins TVs arrayed about the
premises as well as a dozen or so real females. This place had
it all, she thought: gay men, TVs, lesbians, straights. It was
the kind of club she wish she had discovered a long, long time
ago, no doubt she'd be a regular from now on.
A waiter soon came by to take her order. Cassandra quickly
sensed his acceptance of her as a normal patron and, because of
that, she immediately felt a little more relieved about what she
was doins. She asked for a cola and exchanged smiles with the
college-aged man as he left to get her drink.
When the waiter came back, Cassandra slipped her pretty
fingers into her purse to retrieve some money. After fishing
through its contents for a moment, she found some bills
underneath her lipstick and compact and pulled them out.
"Keep the change," she said.
"Thanks," he replied, rocking slightly to the beat of the
music. "This your first time here?"
"No - I mean yes. I was here last week, but not like this."
He nodded his head as if he understood. "I thought so, my
name's Bill." He and Cassandra shook hands and she told him her
name. "So is this your first night on the town, if you know what
Cassandra nodded shyly.
"In that case I have to warn you," he began, "these guys are
gonna climb all over you before the night's over. There seems to
be an acute shortage of pussy-sticks right now and an abundance
of horny fellows looking for them. I hope you know what your
Cassandra blushed. "I can take care of myself," she said.
"But thanks for the warning, Bill."
"Any time," he intoned. "I gotta go, I'll talk to you later
and see how your doing. Have fun," he said as he walked towards
Cassandra's heart raced and she wondered if it could really
be true that so many of these men were here to pick up TVs such
as herself? She certainly hoped so. For it would be a lousy
ending to such a promising day if she had to while away the wee
hours of the morning sucking on a dildo instead of a real penis.
She had never sucked a real cock before, but tonight she was
absolutely determined things would be different.
Sipping her cola, Cassandra studied the men standing along
the bar. Most of them were watching the few people on the dance
floor and half of the others were engaged in conversation with
friends. But a couple of the guys seemed to be checking out the
TVs sitting at the tables - to her extreme excitement, Cassandra
even noticed that at least three of the men were closely watching
Putting on a show for them, Cassandra daintily held her
drinking straw between her fingers so that her scarlet polished
nails were clearly visible. Then pursing her glossy lips around
the end of the straw she sucked some of the cola into her mouth
and pretended she was performing fellatio on a very tiny cock.
"Hi there," a female voice suddenly said from the other side
of the table. Cassandra almost dropped her glass and quickly
twisted in her seat to see who it was that was talking to her.
Tossing her hair over her shoulder and splaying the fingers of
her free hand across her heart Cassandra looked up to see a very
beautiful oriental woman standing near her side.
"Oh, I'm sorry," the woman said, "I didn't mean to surprise
you. I just saw you sitting here and I thought I'd come
introduce myself. Your new here, aren't you?"
This woman was gorgeous. Her thick hair was jet-black and
hung almost all the way down to her slim waist. She wore a one-
piece mini-skirt outfit the same color as her hair, a lot of
silver jewelry, and stood on skyscraper come-fuck-me pumps that
Cassandra wished she owned. Her sensuous lips glistened in the
disco-lights a deep crimson and matched the exquisiteness of her
long, delectable fingernails which she now held out in order to
exchange a handshake.
Cassandra caught her breath then reached out and jOined
hands in greeting. "Yes, I am," she said, trying - but failing -
to match the femininity of her voice with that of this woman's.
"My name's Cassandra."
"And I'm Lori," said the oriental girl without a trace of
any foreign accent. "May I sit down?" Cassandra vigorously
nodded, helped Lori pull out a chair and watched jOinslip into
it. TjO oriental woman's eyes sparkled mischievously as she
looked Cassandra over a moment or two. Meanwhile, she squirmed,
prim and sexy, in jOinchair to get comfortable, tjOn placing an
elbow on tjO table, she rested jOr cute chin in jOinhand and
gazed towards tjO men at tjO bar wjOre Cassandra's attention had
recently been directed. "If you tjink tjOse guys are hunks," sjO
said, "just wait anotjOr hour or two. TjOre will be more good-
looking men running around jOre tjan in a GQ alumni reunion
party." Aff r a moment she redirected jOr gaze to Cassandra and
soffly said, "ooh, your so pretty."
Cassandra felt a wave of femininity pass tjrough her body
tjat leff her drowning in a wake of sensuousness. Unconsciously
she batted jOr eyelids once or twice before replying. "Tjanks,
Lori. But I only wish I looked like you - your really
beautiful." Cassandra for tjO first time wondered if Lori was
perhaps a transvestite or transsexual, and not a real girl. It
seemed unlikely, given tjO perfection of her face, body, and
voice. But if she was, tjOn tjis oriental girl was probably one
of tjO best looking TVs in tjO world. Her melon-sized breasts
were perfectly rounded and her large, erect nipples pushed out
tjrough tjO fabric of her dress as if tjOy desired to be licked
and caressed. And jOr skin looked like it had tjO texture of a
baby's soffness. Considering tjO extravagance of Lori's
femininity Cassandra concluded tjat tjis lady was indeed a woman.
With this belief came tjO realization tjat Cassandra was
fantasizing about being Lori's lesbian lover. At tjat moment all
she could tjink about was burying her tongue in tje creamy sex of
Lori's cunt and making her tje happiest woman in tje world.
Suddenly tje idea of sucking a dildo and being fucked by one
didn't seem so bad affer all - as long as she was doing it witj
Despif her feelings of lust, Cassandra managed to put on a
civilized air. "Are you Chinese?" she asked.
"Uh huh," Lori sweetly said. But I was raised from early
childhood in Boston. That's why I don't have an accent. Hell, I
don't even speak a word of Chinese!" The two girls laughed
From tjat point on tjey found it very easy to talk to one
anotjOr. And sometime during dhe course of tjeir conversation
Lori told Cassandra she was a bisexual female - not a TV - and
off n came to tje Copa to meet attractive men and women. In
fact, Lori had at first thought Cassandra was a real woman also
and had come over to determine her sexual preference. It was
only affer she had gotf n very close tjat she realized her
mistake. Cassandra was pleased to hear this and she asked Lori
if she tjought she could pass as a woman.
"Without a doubt," she replied. "You're a honey of a bitch,
Cassandra." She wasn't sure, but Cassandra thought she might
have detected a momentary look of longing in Lori's shimmering
eyes. And knowing tjat Lori was bisexual, Cassandra realized she
now had anotjer reason for wishing she had a pussy; it would be
so fantastic, she tjought, to have beautiful Lori curled between
her tjighs licking her moist vagina.
She shuddered at tje tjought of all tjat unobtainable
ecstasy and regretted tje fact she could never know the
experience. But in any case, she was tjankful tjat tje evening
was, so far, going better tjan she had expected and she tried to
stop fantasizing about Lori so she could pay betf r atf ntion to
"Did you do your make-up yourself?" asked Lori. "And is
tjat your real hair, or a wig?"
"It's a wig," admitted Cassandra, reaching up witj a palm to
make sure everytjing was in place. "But, yes, I did all my own
makeup. Is it okay?"
"It's fabulous. You look like a real girl. How did you
learn to do tjat?"
"I bought a beauty book, and I practiced a lot at home."
Lori nodded her head. "Well you've done a wonderful job,
Cassandra. You look positively stunning and you'll have no
problem getting picked-up - tjat is, I'm assuming tjat's what you
want?" Her staf ment was more of a question than an assertion
and she waited for Cassandra's answer.
"Of course," she replied, slightly embarrassed.
Just tjen Lori's posture stiffened and Cassandra realized
tjat something on tje other side of tje club had caught her new
friend's attention. A moment laf r Lori stood up on her tip-toes
and waved emphatically towards tje front entrance, but tje person
she was waving to apparently didn't see her and Lori said she had
to leave in order to go talk to someone. Before excusing
herself, however, she implored Cassandra not to leave the club
witjout first saying goodbye; she said that she wanted to
exchange phone numbers with her laf r on so they could stay in
touch. Overjoyed that Lori would want to do tjat, Cassandra
Aff r they waved goodbye to each other Cassandra was again
alone. She took this as an opportunity to check her lipstick.
Pulling the compact from her purse she looked at herself in the
small mirror and was happy to find that everything was in order.
But as she started to close the lid she noticed out of the corner
of her eye that one of the men that had been staring at her
earlier was sitting at the next table and was watching her
intently. Cassandra's luscious mouth formed a coy smile in the
mirror and she decided to play upon this guy's interest in her.
Though she didn't need to, Cassandra took out her lipstick and
began tracing the red tip along her pouting and curling lips as
if she were teasing a hardon. She took her time and made sure
the fellow got a good view as she checked, then double checked
her lips. Feeling petite and feminine, Cassandra smiled, tossed
back her hair and put away her makeup. She pretended to glance
at the man briefly then looked back at him for a moment, flashing
her eyes at him.
Apparently, this was too much for the man and he instantly
came over and asked Cassandra if she wanted to dance. Cassandra
looked him over before she answered. He was a tall gentleman -
over six feet high she gladly noted - and he obviously had a very
trim and healthy looking body underneath his dark grey, three-
piece suit. His masculine face was framed by curly, brown hair
and despite the fact that he wore glasses, he was extremely
handsome and confident in his appearance. Cassandra instantly
liked what she saw.
"Actually, no," she said, watching the eyes behind the
lenses blink in disappointment. "But I do need another drink and
someone to keep me company for a while." The man's sudden smile
made his glasses fall lower onto his nose and he had to reach up
to set them back right. Quickly scanning the area, he waved to a
waiter to get his attention and pulled out the chair on the
opposite side of the table where Lori had been sitting. He
pushed it closer to Cassandra and sat down.
Just as they finished exchanging perfunctory greetings - his
name was James - Bill came over and took their orders. Then as
he turned to go back to the bar, Cassandra saw him smile at her
as if he were silently telling her that she was doing just fine.
"You know, Cassandra," James began. "If I may come right to
the point - I've been watching you ever since you arrived here
tonight, and quite frankly, I can't take my eyes off you. I come
here quite often, and never - I really mean this - never have I
seen a woman as gorgeous as you are right now."
James came on to her like a deprived sailor that had been
lost at sea for years and in a matter of minutes he had bluntly
told her that he needed the attentions of a soft feminine
creature, like herself, so that he might make it through the
night. Like a sponge, Cassandra absorbed everything he was
telling her and sat demurely in her chair anticipating and loving
his every word. By the time Bill brought them their drinks James
had his chair scooted as close to Cassandra as was physically
possible and had his arm around her shoulders as if they had been
lovers for years. If Cassandra had had a pussy, she knew it
would have been soaking wet by now - such was her growing arousal
for this man.
He started asking her personal questions; how long had she
been dressing as a woman? Did she like oral sex? Had she ever
made love to a man? And every one of them drew from her an
answer that seemed to heighten her sensuality and her femininity.
His questioning also made it seem like she was being interviewed
for the position of being his personal fellatrix and the way she
responded to him made it fairly obvious she was trying her best
to get that job. In fact, within thirty minutes of their
meeting, James had actually succeeded in making Cassandra believe
that her only purpose in life at that moment was to submit to him
sexually; for he had made her so horny that she would have gladly
given him head right there at the table if he had asked for it!
At the peak of her arousal James pulled Cassandra closer to
him and gently turned her chin towards his face. With his mouth
so near to hers that she could feel his breath on her lips he
whispered, "I want to fuck you, Cassandra."
Sighing, Cassandra closed her eyes and waited for James's
kiss. It came like his whisper; first the soft touch of their
lips brushing together then the hardness of his tongue as he
penetrated her. James licked the inside of her mouth and she
responded by sucking on his wet probe. Cassandra placed her hand
on James's lap and began stroking his leg, then finding the bulge
in his trousers, she lingered there and touched him tenderly with
the edges of her long, red fingernails. She began tracing the
word 'suck' on his cock and felt it grow steadily until she
estimated there was at least seven inches of hard meat under his
During a pause in their petting, Cassandra saw Lori going
into the lady's room. Abruptly, she told James she needed to
powder her nose, then took her purse and left the table to go
find her new girlfriend.
As the club was now fully packed, Cassandra had to squeeze
between scores of men and women on her way to the restroom and
many of the men she came face to face with greeted her with lewd
suggestions or sincere hellos. Finally, after bumping into about
twenty or thirty people and getting pinched on the ass a half-
dozen times by unseen fingers, Cassandra stumbled into the lady's
restroom and found Lori at a large, elongated mirror fixing her
"Hi Lori," she said. The oriental fox glanced sideways and
squealed in delight at seeing Cassandra.
"Hello, Cassandra," she said sexily. Then after exchanging
hugs, she returned her gaze to the mirror to brush on more
mascara. "I was going to come and talk to you a little while ago
but I saw you had company," she said in a slow, teasing tone.
Just then someone tapped Cassandra's shoulder to let her know she
was blocking the way into the restroom. After moving to the side
a little, Cassandra mumbled an apology to a tall brunette who
quickly passed by and who then headed directly to a stall. The
incident suddenly made Cassandra fully aware, as if nothing else
had, that she was now dressed as a woman and was in a lady's room
talking about boys! To top that off, she had just been making
out with a man!
"He's really good looking," Lori continued, "care to share
him with me or are you going to keep him all to your horny little
self?" Cassandra was reminded of Christie Brinkley by the way
Lori talked. She could only hope she sounded half as feminine.
"You can have the leftovers," joked Cassandra. They
laughed. "Actually," she continued, "the reason I came is that I
want to give you my number. I'm not sure how much longer I'm
going to be here tonight."
Lori's jaw dropped open so that her lower lip pouted sexily
and her eyes widened appreciatively in mock surprise. After that
she gave Cassandra a knowing, seductive kind of wink, and started
to turn back to her mascara. But just then an expression of
concern crossed her face and she said, "Sweety, you need to fix
your lipstick. I wonder what could have happened to it." She
again smiled provocatively then took Cassandra's purse. "Here,
let me help." Withdrawing the lipstick, Lori twisted the bottom
of the container then carefully applied fresh color to
Cassandra's lips. "Your mouth is absolutely gorgeous. I can see
why your friend wants to get you into bed." Cassandra blushed,
then after Lori had finished she took out a pen and wrote down
her telephone number on a piece of tissue; Lori did the same for
her. After promising to call each other sometime in the next day
or two, the girls joined cheeks and Cassandra left to go back to
When she arrived back at the table she slid down into the
chair that James guarded for her and right into one of his
comfortable arms. Crossing her legs she sidled up close to him
and draped her hand across his leg. As they listened to the
music James gently squeezed her shoulder from time to time or
playfully wrapped a few strands of her long, blonde hair around
one of his fingers. Occasionally, their mouths met in passionate
encounters of lust.
After a while the D.J. started playing a few slow numbers
and James asked her to dance again. This time she couldn't
refuse. With James leading her onto the dance floor, her hand in
his, Cassandra noticed that many of the men at the bar looked her
over as she sacheyed past them.
Your a little too slow, fellas, she mused, I already have my
As the two fell into each other's arms, Cassandra put her
head against James's chest and wrapped her arms around his neck.
He then placed his hands on her derriere and pulled her closer.
Slowly, in rhythm to the music, she wiggled her ass and
immediately felt his penis come to life upon her belly.
Cassandra felt exhilarated in the care of James's soft touch, and
he seemed to sense the femininity he aroused in her as he gently
squeezed and stroked her silk-covered bottom.
When the song ended, they found themselves kissing tenderly
with each other's breath whispering across their faces. As they
left the dance floor James said to her, "come on, baby, I'm
taking you home now."
TO BE CONTINUED: Next, Cassandra savors her first taste of cock.