Transgender story

SHEMALE MAID

Colleen rushed through the mansion's open gate and headed towards the main
door. She opened her mini leather bag and searched frantically for her keys,
although she knew she was hopelessly late. Was it her third or fourth
unsuccessful attempt in a row to get there on time? Or had there been more?
Oh, how could she answer that question when she had been at a complete loss
for more than a month? Her boyfriend, Tom, who was a marine, had been sent
to Iraq, as a member of an elite force assigned to seek and destroy
missions, and since he left all she could do was to cry and pray for his
safety. He had promised to write to her every day but, alas, she had never
received anything and what is more, she was afraid of the worst.

Colleen, at her twenty four, was a very pretty and graceful girl, standing
5' 9'' tall, with such perfect curves that every time she walked down the
street the crowd filled the air with cheers and whistles as if they were
watching the grand parade. A cascade of shoulder-length straight hair,
parted in the middle and blonde as a hay-field during summertime, framed her
oval pale face and her delicate petite nose stood out as a masterpiece of
unsurpassed craftsmanship. The deep blue color of her eyes could easily make
the sky hide in shame and her thin, but burning, scarlet lips would set on
fire even the most unwilling flesh.

Her 36-full-C tits were as much round and firm as big inflated balls, with
big aureoles and dark brown nipples which always stuck out like huge
doornails- as we shall see there was a reason for that. She had a thin
ring-like waist and full hips which gave her figure the shape of a cello.
Her legs were long and slender and her ass cheeks small and muscular. The
only hair that covered her body was in her pubic area trimmed in the shape
of a wide `V'.

However, a nasty or welcomed surprise, depending on one's point of view,
waited the unsuspecting. Instead of having a blooming flower surrounded by
delicate pinkish folds between her legs, she had... something extra. A tiny
spear made of flesh accompanied by a hairless pair of small balls. Yes!
Colleen was a shemale heartbreaker of untold beauty.

As far back as she could remember she always acted like a girl by playing
with dolls, wearing dresses, using lipstick and rouge, flirting with boys
and etc. Was it because her parents, deep in their hearts, wished to have a
daughter instead of a son because they thought she would be looking after
them, when they grew old, as well-bred daughters ought to do? Had the
balance of her hormones been disturbed during her mother's pregnancy somehow
by that secret desire of her parents? Or was it simply that the fact of
being constantly dressed as a girl throughout her tender years had played a
significant role in changing her attitude and bringing out her feminine
side? And who would blame her parents for that? She would never do that,
that's for sure. Why? Because she was happy with her sexuality and despite
her gender she never felt otherwise.

Before turning nineteen, Colleen had already decided to undergo an operation
that would transform her into a real woman. For that purpose, she had
visited Dr. Harding's clinic, one of the most eminent surgeons at that time,
and asked his advice. He had told her that three stages needed to be
completed: first of all, she had to undergo a hormone therapy, then a breast
surgery and finally, the removal of her genitals would ensue.

On hearing the amount of money it would cost she had broken down and burst
into bitter tears, and Dr. Harding, feeling sorry for the unjust fate of the
poor girl, had kindly offered to complete the first two stages for free on
condition that she would be working for him as a maid until she repaid her
debt. As for the third stage, they would surely think of something in the
near future. She had gladly accepted and attempted to kiss his hands but the
good doctor had gently sent her away, giving her the address of his mansion.

Dr. Harding kept his promise and she, eventually, undertook the
responsibility of all household duties and expenses. Of course, besides
being conscientious, clean and honest, she had to be always punctual and
`well-dressed'. `Well-dressed' meant that every day she had to choose her
maid outfit from a collection of fifty, more or less, unique pieces and
accessories, which had been especially designed for her size.

Dr. Harding was at his fifties and was a highly respected surgeon who had
devoted his life to the glories of his science. He was kind at heart,
generous, open minded and extreme intellectual. With height over 6 feet,
weight 180 pounds, strong legs and body well built, he looked as much
imposing and fearsome as a professional wrestler. His silver-like grey hair
was cut short and he had a narrow sharp face with coarse features, blue
eyes, a rather big arched nose and thin lips- you could easily mistake him
for some kind of gunfighter of the eighteenth century.

He had been neither married nor engaged, although he had had many female
pursuers. Just the same, he preferred to lead a solitary life devoided of
any trivial concerns which might disturb the state of his everyday life- he
was a pure Stoic, as most people would say. Besides being in love with his
profession, he was also an avid collector of Chinese porcelain vases, many
of which belonged to the Ming and Qing dynasty, and he was very proud of it.

Colleen, at last, found her keys and opened the door. She ran through the
hall like a 100-meter-athlete and entered the lounge... only to find Dr.
Harding at his office, reading the `Nature' magazine. Colleen froze at her
position and remained silent, waiting for his reaction; only her fingers
were showing signs of life as they were nervously clenching and unclenching
the straps of her bag.

He lifted an eyebrow and inspected her from head to toe, for some time,
before he spoke.

Dr. Harding: "Good morning Miss Colleen. Might I ask you where have you
been? You are late again. I have lost the count of how many times I have
caught you belated during this month. You do know how much I hate delays,
even though you have been forewarned many times."

Colleen: "I know... I know Mr. Harding. You have always been kind to me... It's
that I worry about my boyfriend. I haven't heard from him since the day he
left and... I promise I will never be late again."

Dr. Harding: "Very well. Go upstairs, change your clothes and come back. I
want you to take care of my collection... My poor vases never looked so dirty.
When was the last time you dusted my vases? A year ago?"

Colleen: "Oh, NO! I dust them every week... I'm very sorry Mr. Harding. I'm
going upstairs to change and I will have them cleaned in less than ten
minutes."

She ascended the stairs as fast as she could and entered the dressing room.
Feeling guilty about her behaviour, she stripped naked and opened the
built-in wardrobe. She knew she had to choose something really nice if she
wanted to distract his attention. He seemed to be extremely upset and she
was afraid that he might be considering of firing her.

She searched through the wardrobe until she found what she was looking for.
The maid outfit she chose consisted of: a pink fishnet dress, with very thin
shoulder straps, which barely covered the middle of the thighs; a white
collar and a red bow tie; a white apron with a big red heart in the middle;
a scandalous tiny pink g-string; red stockings and 5 inches stiletto heels
made of glass.

She got dressed, took a black feather duster and descended the stairs very
carefully, trying to keep her balance after each step. Dr. Harding looked
absorbed in the reading of his magazine but every time she wasn't looking at
him, she could feel his eyes glued on her back. So, she started cleaning
vase after vase, assuming lewd stances which would give him an ample view of
her amazing curves.

She would completely bend over, bringing the upper body in a horizontal
position, and dust the vases smoothly and slowly, swaying her marvellous ass
cheeks with the grace of a cat. Sometimes, in order to reach the far side of
a bookshelf, she would balance on one foot and put the knee of the other on
a convenient spot so that the thighs would form a 90-degrees angle, causing
the disappearance of the string between her smooth orbs. If the height and
width of a vase were appropriate, she would rest the bulk of her tits on its
top and her delicate fingers would caress its surface as if it were her
baby.

All was going well until disaster struck. She was knelt on an armchair, with
elbows resting on top of its back, waving playfully her shapely calves up
and down, when a clumsy movement caused a vase to fall off a bookshelf and
smash into pieces. Upon hearing the crash, Dr. Harding threw his magazine in
the air and rushed to her. He moved so fast that even before she could utter
a single word, he had already grabbed her from the nape and was pressing her
face against the chair, forcing the arching of her back and ass.

Colleen: "What... What are you doing to me Doctor? You are... hurting me!
Please... Please... STOP IT!"

Dr. Harding: "You... You wretched imitation of an unworthy female... How did you
dare to break one of my vases? Do you think that I am going to let you
destroy the efforts of a life without doing anything? I would rather KILL
YOU!"

Colleen: "Oh NO! Please...You are scaring me! I didn't mean to do it... It was
an accident! I beg you Mr. Harding... Show mercy to a hapless poor girl who is
haunted by the cruelest fate... A girl, who would never dare to dream of
becoming a real woman if it weren't for your great tolerance and kindness...
I'll do anything... anything to make up for your loss... Please... just don't kill
me..."

Dr. Harding: "Bah! You aren't worthy of my respect and generosity. It would
be ridiculous to stain my hands with your unworthy blood. Instead, I'm going
to teach you a lesson you will never forget. I should have done it since the
first moment you set foot on my noble house. You are nothing but a filthy
whore and henceforth I shall be treating you the way you deserve."

So spoke Dr. Harding, and with extreme haste, without relaxing the grip on
her neck, he denuded her bubble buttocks, by folding the fishnet fabric
around the waist, and put aside the red string, uncovering the puckered
entrance of her narrow canal. Then, he unzipped his trousers and drew out
his throbbing sword which looked incredibly thick and angry.

He guided the bruised head of his member to the threshold of her undefended
opening and without warning he thrust it inside. By sheer reflection, she
bucked her hips like an untamed mare and pulled her joined calves as much
closer to her body as she could, letting out a desperate whine which could
afflict even the most ruthless criminal on earth.

Dr. Harding passed the bulge of his cock-head through her tight ring hole
with extreme difficulty and proceeded in pushing the rest of his organ
inside her unwilling path without remorse. His iron grip had pinned down her
beautiful face on the back of the armchair and the only thing she could do
was to wiggle her body, like a fidget child, and cry. Tears of desperation
bedewed her cheeks as he was inexorably filling, inch by inch, the void of
her virgin entrails with the burning flesh of his manhood.

It didn't take him too long to bury all 7 inches of his old cock inside her
bowel and having achieved his goal, he stood still in order to give her some
time to adjust to the new situation. Her body started to shiver
uncontrollably as her ass muscles were making the necessary adjustments to
contain the mass of the rude intruder as a whole, rendering the pain inside
her guts unbearable. Dr. Harding couldn't ask for more as her delicate
membrane, being warm and clung around his inflated tool like silky tights,
was giving him the most intense and exquisite massage he had ever had.

Colleen thought that the worse had passed when he started to pound her
stretched rim with lightning speed. His battering ram was tearing the jelly
walls of her back canal to shreds and his hands were pushing her shoulders
down, forcing her buttocks to rise up. She had embraced the back of the
armchair and was clenching her fists in agony as she was being pushed
relentlessly against it, yelping like a b-movie starlet in distress. His
violent attacks to her bottom were so powerful that the coarse fabric of the
chair was scratching her face like razors, her tits were bouncing like
soccer balls, while her semi-erected dick and bald balls were swinging
freely between her milky thighs.

Dr. Harding was working his blunt `weapon' into her neglected bum very fast
in and out and every time he thrust it inside her glassy heels would hit him
on the butt in response. He had already reached top speed some time ago and
was nearly exhausted- he was panting like a hound dog and thick beads of
sweat were dripping from his forehead on her back.

Drawing upon his last ounce of strength, he grabbed a handful of her hair,
pulled her head closer to his and lunged forward in a desperate attempt to
reach the deepest point of her battered rectum. He roared his victory like a
mountain-lion and began spurting his thick white cream inside her raped
bowel like a painting pistol. After a while, he withdrew his dripping dick
and tried to catch his breath, wiping away the sweat from his forehead with
the back of his right hand.

With hot semen still trickling from her abused hole down to her balls,
Colleen turned around and knelt before him. Very carefully she put his spent
cock into her mouth and went on to suck him gently. After sucking him for
some time she passed her tongue many times along the shaft and around the
head, licking and swallowing everything she could. She even squeezed the
head with her fingers in order to accept in her willing mouth the last drop
of his orgasm.

Having licked him completely dry, she put his veteran cock back into his
pants and zipped up the trousers, looking pleadingly at him as devoted
housekeepers always ought to do. Obviously, his anger had disappeared
because he immediately smiled and patted her on the head as if she were his
favourite pet. By sheer gratitude, she embraced his thighs and started
playfully to rub her nose and cheeks against the bulge of his trousers, like
a well-fed kitten, when the doorbell rang.

Dr. Harding ordered her to answer the door and headed to his room. She stood
up and quickly collected the semen from her sore anus and hairless balls
with her right hand. Without forgetting to destroy all evidence of her
indecent behaviour by licking clean her hand, she brought her string back
into place, straightened her fishnet dress and off she went.

Colleen: "Who is it?"

Postman: "Hey Colleen! It's John! The postman!"

Colleen: "Oh! And what brings you here John? I think it was yesterday when
you delivered our mail."

Postman: "I bring you great news Colleen. A letter that will shake the
foundations of your entire world! Make a guess!"

Colleen: "Oh my God! I don't believe it! At last, the Merciful God answered
my fervent prayers and sent me his most beloved messenger. I'm shaking all
over! John, please, insert the letter through the door's special opening, I
can hardly wait."

Postman: "Not so fast Colleen. If my memory serves me right, a month ago,
you promised to do me a great favour if I brought you the letters of your
boyfriend as soon as I could. So, are you going to keep your promise or
not?"

Colleen: "Oh, okay... okay. Just give me the letter and I'll keep my promise
provided that everything you have told me is true. Come on, hand me the
letter."

Postman: "I may be young but not stupid Colleen. First, open the door and
let me in and then I'll tell you what I want from you. Only when I have
finished, shall I hand you the letter. I can't wait to feel your velvet lips
around my cock and I promise to severe punish that audacious tight ass of
yours. Oh God, I have never had such erection in my whole life. I have
always been dreaming of sticking my rigid member in your sweet ass while you
are lying naked on the kitchen's table with your legs around my waist and..."

Colleen: "Stop dreaming, you moron. Mr. Harding is inside the house and as
you know I'm not allowed to open the door to strangers. But even if he
wasn't inside I would never let you in; not that I would ever make love to
you. You are disgusting me!"

Postman: "In that case... I could destroy the letter and nobody would ever
learn..."

Colleen started to bite her nails as she had to decide whether to let him in
or turn down his offer. Letting him in, wasn't really an option because if
Mr. Harding caught them inside his house she would find herself in great
troubles. On the other hand, if she rejected his offer she would never hear
from her boyfriend and that was out of the question too.

On top of that, she despised him so much that wasn't sure if she could
endure a sexual intercourse with him without emptying her stomach the very
first moment. He was an ordinary 29-years-old red hair man, 5'8'' tall,
overweight, glabrous and freckled like leper, with dull small green eyes and
pointed chin. The worst of all was that he always stunk like a pig as if he
had never had a bath in his whole life.

Things looked quite ominous and grim and it seemed that there was no way out
of her troubles. If she wanted to find an acceptable solution she had to
change her point of view entirely and think in a roundabout way by making
use of the female qualities of her brain and intuition. Sometimes, if you
find yourself limited to only two unacceptable options and you have to make
a decision in very short time, you can always turn the tables by choosing a
third one that suits you best, regardless of the consequences, for you are
in dire straits in any case; and that was exactly what she did.

Colleen: "Listen John. We can settle this matter immediately only if you
accept my offer. I can neither let you in nor let you go without getting
that letter. The only thing I can do is to suck you off through the door's
special opening. As you see, the dimensions of the slit are large enough and
you can safely insert your dick without fear of hurting yourself. But it
must be done now. I'm sorry there is no other way. You can take it or leave
it, it's your choice. This is the best offer you can get. So hurry up, for
we are running out of time."

Postman: "But... but... Damn you girl! You are driving a hard bargain... Umm...
I don't know... What if someone comes through the gate and catches me doing
that? That would be so embarrassing! Damn..."

The postman shook his head in disbelief. The situation had radically
changed, putting him at a great disadvantage within less than a minute, and
he couldn't understand what had gone wrong. His slow mind couldn't conceive
the fact that he had been outsmarted by that girl, the very moment he was
sure he would triumph.

Time was flying like a tsunami wave and he couldn't make up his mind-he
could lose his job for something like that! But he was so aroused that could
hardly control the desires of his body. "To hell with all of you!" he
thought as he was checking nervously for any passers-by. "I'm going to do it
and... come what may!"

He checked behind his back once more, unzipped his trousers and pulled out
his aching dick. It was 6 ½ inches long, 2 wide and sweaty, with a big
purple head which smelled urine. Quickly he inserted it into the slit,
bringing his body closer to the door, and with a trembling voice informed
Colleen that he was ready.

As soon as she saw his dick coming in, Colleen squatted behind the door and
touched it. Her right hand embraced the thick shaft and began to stroke it,
gently moving the skin back and forth. The postman sighed as she was jerking
him off with great skill, sweetly covering and uncovering the head of his
cock without haste.

He stuck completely his body and hands on the door in a spread-eagled-like
position so as to give her more of his flesh to play with, although his fat
belly was getting in the way. Colleen squeezed his shaft hard, forcing the
bulbous head to swell more, and started to brush its sensitive flesh with
the soft underside of her thumb, slowly drawing nerve-racking circles around
the hole.

Colleen was feeling reluctant to put into her mouth his sweaty dick because
it looked dirty and smelled urine but she couldn't avoid it in the long run-
she had to keep her promise. She brought her mouth closer to his bulky
spearhead and stuck out her little pink tongue. Hesitatingly, she touched
the foreskin with the tip of her tongue and began to tickle it, holding
still the rest of his member with her right hand.

After a minute or so of sweet torturing, she swirled her tongue around the
head a few times and then decisively took it into her mouth, sealing her
lips around the base. The moment he felt the warmth of her mouth around his
cock-head he went crazy and started to rock his pelvis back and forth,
slamming his obese body and balls on the door like a lunatic.

Colleen sat on her heels, resting the palms on the thighs, and held her head
still, tightening only her lips around his moving piston. With eyes wide
shut, mouth half-opened and right cheek stuck on the door, he was sweating
and breathing heavily as he couldn't stop plunging his unwanted dick
relentlessly into her divine mouth, enjoying the ultimate pleasure a mortal
could ever feel- he didn't have to sell his soul to the Princess of
Deception for that! He was ramming his mast into her wet nest as if there
were no tomorrow, sometimes hitting the roof of her mouth and other times
the velvet opening of the throat, while she was standing obediently still,
working only the muscles of her mouth.

Soon he got exhausted and his momentum subsided without having relieved
himself. Was it because he noticed someone passing by? Or was it the fact
that being there for so long had finally upset him so much that he just
couldn't concentrate? Anyway, that was too annoying and Colleen decided to
help him.

She grabbed his dick, crammed her mouth with his raw meat and went on to
suck him. Like a wild animal, she was sliding her mouth back and forth along
the head, inflating and deflating her cheeks accordingly, while her hand was
squeezing and jerking the shaft with rage, but to no avail. Even the
deliberate loud slurping noises she was making didn't help at all.

Her jaws and knees were aching like hell and weren't sure if she could
produce any more saliva, let alone continue any longer. That guy was so
scared that even Goddess Venus wouldn't succeed in getting him off in time-
he could torment her all day long. Colleen, with saliva dripping from the
corners of her mouth and chin, was standing there like an idiot, firmly
holding his slippery dick in her right hand, not knowing what to do next.

Tired and frustrated to the point of no return, she put the swollen head on
her left breast and began feverishly rubbing it over the fishnet fabric,
bringing it into contact with her protruded nipple as well. The feeling of
his sensitive skin being brushed against the fishnet's threads and her hard
nipple was so effective that immediately brought the desired result.

The postman plunged his fingernails into the wooden door, threw his head
back and howled his orgasm aloud like a starved wolf. He was spurting... and
spurting... his hot semen endlessly, splashing it all over her neck and
breast, flooding and covering the whole nipple with a thick crust of his
sticky milk, while she was jerking him violently off on her soft skin.

After emptying literally all of his fluid on her perky tit, he tried to
withdraw his cock but Colleen didn't let him.

Postman: "Hey Colleen, let it go... I've got to zip my trousers... Please you
are hurting me..."

Colleen: "Give me the letter and I'll let you go, not before."

Postman: "Someone is coming! Let go my dick Colleen... Please! I'll give you
the letter, I promise."

Colleen: "Give it to me now or else I can keep you here forever."

Postman: "You filthy witch... Take it... Are you happy now?"

Colleen took it and let him go. Without caring about her aching knees and
the semen which was trickling from her breast down to her tummy and thighs,
she opened the letter with trembling hands...