#1303 - Sissy Story 42 - The Countess and the Contest

Again here for our sissy appointement.. with stories..
today, with one.. a really well written.. that remembers me Marquis de Sade..
not really for the cruelty of his tales... but for the mood of this situation..
anyway.. we missed, on our collection, a sissy maid chapter..
so i'm sure you will be delighted by this wonderful tale..
written with a sublime taste about details..
enjoy the sissy story number 42! ;)
with love

Anna Malice




The Countess and the Contest




"Heathyr." The haunting, melodic tones of the Countess' voice rang out
through the cold, silent house. Even after months in her service, I still
couldn't get over the way the exquisite marble floors and twelve-foot
arched ceilings managed to create seemingly impossible acoustics. It was
as if the entire house was built to obey her beck and call -- which
probably wasn't that far from the truth.

I froze in place, carefully bent at the waist, with my ass in the air.
My tight, binding corset did not allow for much freedom of movement. Even
if it had, I was too well trained to allow myself to ever relax my posture.
"Your presence is requested in the parlour."

A sudden chill trickled down my spine. The only time she `requested' my
presence was when there were guests to be served, or if she was
particularly angry with me. Since I had not been summoned to attend to the
door, I had to assume it wasn't the former. However, I couldn't recall
doing anything to prompt such anger in the usually serene Countess.

Regardless, it was my duty (and my pleasure) to obey.

With only the briefest hesitation, I gave the mahogany bookcase one last
wipe with the pink feather duster, and then hurried downstairs. The sound
of three-inch, silver tipped stiletto heels upon the marble stairs
announced my presence long before I arrived.

"You called, Countess?" I halted just inside the door of the parlour and
curtsied deeply. As my training dictated, I lifted my leather skirt high
enough to reveal the black satin panties beneath and waited. It hadn't
been easy earning the privilege of satin, so I was especially careful not
to give her cause to take them away.

"Hmm . . . smooth, no bulge, but I do believe that you are wet."
Despite the darkness, I couldn't miss the dangerous glint in her eye. "Is
it fresh, Heathyr?"

I blushed deeply as my own professionally manicured fingers brushed
against the damp spot. While I was prohibited from pleasuring myself, a
small measure of excitement was allowed in her presence. "Yes, Countess."

I held my finger up for her to lick the spot of pre-cum from the tip,
proof that it was indeed wet and fresh. "Good." She nodded sharply, and
then dismissed the issue with a wave of her velvet-gloved hand. "You may
enter and prepare for our guest."

It was a struggle not to let my relief show. "Thank you, Countess."
It's not so much that I feared punishment, but that the thought of
disappointing her - in any way - made me physically ill. I was almost
orgasmic in the knowledge that I had not angered her.

The first step in my carefully laid-out ritual was to make sure the
heavy, black velvet curtains were securely closed and fastened along the
seams. Even the smallest shaft of sunlight piercing through to strike the
antique, hand-woven carpet would mean twenty lashes. At least I assumed
that was the prescribed penalty for such an offence - I had only made the
mistake once.

Next - and this was often the most difficult step of all - I had to
guess the Countess' mood, based on nothing more than a few words and a wave
of her hand.

Guiltily, I risked a quick glance back towards the couch and confirmed
my immediate impression upon first entering the room. The Countess was
dressed primarily in a dark burgundy this afternoon, with black lace
accents. That alone told me this was to be a casual affair, as did the
unusual absence of her thigh-high leather boots. For that matter, she
didn't appear to be wearing any leather at all - a definite first in my
experience.

Anxious, as always, to get it right the first time, I risked another
glance towards the Countess. Her velvet dress was full-length with a high
neckline, revealing only a glimpse of alabaster flesh where the sleeves
ended and her matching gloves began. Her makeup was sparse, yet elegant as
always, but her jewellery was rather . . . subdued.

Not only was this to be a casual affair, I guessed, but presumably a
familiar one as well. Carefully, following the prescribed ritual, I began
setting the blood red candles alight. As always, I started in the far
corner of the room, banishing the darkness there, and then ushering the
flame into the Countess' glorious presence. As my hand hovered above the
final candle, though, I froze. The Countess chuckled softly. "Is there a
problem, Heathyr?"

"I . . . please forgive me, Countess. I did not realise your guest had
already arrived." With shaking hands, I quickly lit the last candle and
laid the box of matches on the mantelpiece. I stepped forward and curtsied
before our guest.

"Please accept my apologies, Sir. I had not meant to be rude. May I
get you a drink, or - oh!"

The stranger laughed as he gave my imprisoned penis another squeeze.
"So, there really is a boy under that sexy costume!"

Despite my training, despite my submissive nature, I wanted to protest.
I wanted to cry out that he was wrong, to deny his crude comment.
Fortunately, the Countess spoke up and chastised him herself.

"Nathaniel, really . . . I thought I already made that clear." There
was a dangerous edge to her voice that told me this was not to be the
friendly affair I had expected. "As we discussed earlier, the genetic
remnants of Heathyr's past are completely irrelevant to me. SHE is mine,
and SHE is precisely what I need HER to be." There was a long pause.
"Understand me - there will be no more of this boy talk."

He just laughed. "Then perhaps we should get this show on the road and
put her to the test, hmm? Let the little slut taste a real man?"

The Countess released a bored, drawn-out sigh - something I prided
myself in not having heard for months. If she really held her guest in
such disdain, though, why the casual, familiar mood? Something strange was
going on here, but I sensed that things were going exactly as she had
planned.

They always did.

"Very well. If that is the proof you desire, so be it." She pointed
towards his blue-jeaned crotch and waved her fingers dismissively. "If you
would, please, Heathyr?"

"Of course, Countess." I knelt carefully before our guest, arranging my
skirt around me. As I stared at the man before me, I blanched. Even
without the benefit of a mirror, I knew I must have looked more like one of
the wannabe-vampires that the Countess so disdained, than the artful,
elegant goths she embraced. There had been a few, completely minor, things
in my training that I'd been reluctant to accept, but nothing I'd felt the
slightest inclination to refuse. I truly believed in the path I'd had
embarked upon - with her stern guidance, of course - but this . . . my
feelings about this confused me.

There was no denying the fact that I wanted his cock. Such a thought
would have never entered my mind prior to coming to the Countess, but she
had trained me well. She had taught me all about what would be expected of
me as a woman, and had thoroughly trained me to take pleasure from my
duties. Not that pleasure was ever to be my primary concern, but she
firmly believed that the best slaves were those who took satisfaction in
their work.

Still, this man was not the Countess, and his cock was not one of her
strap-on dildos.

"Go ahead, Heathyr, and make it quick. You know very well it's nothing
that I haven't enjoyed before."

Strangely, that was all it took to resolve my confusion. If the art of
fellatio was good enough for the Countess, then I would consider myself
privileged to enjoy the pleasure myself. Of course, I would have obeyed no
matter what - I could think of no greater shame than disappointing her -
but the thought of growing one step closer to her idea of perfection was
extremely arousing.

"Yes, Countess." When I turned back to face our guest, I saw that he'd
already freed his semi-erect penis.

I placed my dark red lips around the shiny head and kissed it softly,
leaving a ring around the top. The taste was a little strange, but not
unpleasant. It was certainly softer, with a different texture than a
dildo, but the shape was one my mouth had long become accustomed to. I
made a loose `O' of my lips and slowly took his cock into my mouth, coating
the shaft with saliva. Once he was all the way inside, I began gently
sucking while slowly pulling away.

When I was done, a fully erect, hard, swollen cock popped out of my
mouth and sprang up to smear a drop of pre-cum across my nose. For a
moment, I stopped and stared in wonder. I had done this. I had made him
hard.

For a moment, I wasn't sure what to do next, but the Countess' training
soon took over. I dropped my head down and took his balls into my mouth.
They were hairy and hot, something I wasn't sure I liked, but I knew how
important it was to worship all aspects of his manhood. After a few
moments of gentle sucking and licking, I let the fall away to bounce
against my chin as I began licking my way back up the shaft.

Fully erect, I gauged his cock to actually be a bit shorter than my own
sissy clit, but easily three times thicker. It reminded me of the strap-on
dildos the Countess had first trained me on, before graduating me to the
monsters she enjoyed herself.

Upon reaching the tip, I gave his cockhead another kiss and swirled my
tongued against his piss-slit. Keeping a tight seal around his cock, I
plunged my head down and took all of him into my mouth. Much to my
surprise, I found myself disappointed that his cock wasn't long enough to
force its way down my throat. As much as I had gagged - and, on one
humiliating occasion, even thrown up - while deepthroating the Countess'
collection of dildos, I had come to love the feeling of utter submission it
gave me.

"Hmmm . . . yes . . ." His voice dropped to a low, satisfied growl. He
grabbed a handful of bright red locks and forced me to suck even faster. I
began bobbing my pretty head up and down in time with his thrusts. "Ohhh .
. . very nice . . . you learn fast."

From her seat across the room, the Countess laughed. "You don't know
the half of it, my dear Nathaniel. When Heathyr first showed up on my
doorstep, she was wearing black jeans, a black T-shirt, black sneakers, and
these oh-so-tacky sunglasses. I half-expected her to ask if I needed my
driveway paved or my lawn mowed."

I blushed red in embarrassment at the memory, but continued working to
please our guest.

"You can imagine my surprise when she dropped to her knees and begged
the honour of serving me. To start with, I insisted she rid herself of
that drab little outfit, which she did - right on my front step. I was
impressed by her eagerness to please, so I allowed her inside."

Suddenly, just as I felt the warm penis begin to swell beneath my
tongue, our guest pushed me way. Not sure what he expected by way of a
response, I giggled demurely and lunged forward for another taste.

"Hey!" He slapped my cheek hard enough to leave a mark. "I'm curious to
hear the rest of your story. You can lick me until I tell you to
continue."

The Countess continued. "By then end of that first day she'd shaved
everything from the eyebrows down, dyed her hair my favourite shade of red,
and adopted her first set of nail-extensions. I think it was the hair that
convinced me of her sincerity - men are so skittish about dying their hair
-- but I chose to . . . toy with her a bit."

"While she finished cleaning the bathroom I laid out three complete
outfits upon her bed. The first was a velvet dress of black and red that
matched my own; the second was a black latex minidress with red PVC
waist-cincher; and the third was what you see her wearing now - the black
leather dress and red leather corset. The poor thing must have fretted
over the decision for a good half-hour, but she proved her taste by making
the right decision."

The Countess smiled as I self-consciously adjusted my corset. "After
that, I let her guess how I should be addressed. Her first choice,
predictably, was Mistress. That earned her a slap. Her second choice was
Milady. Amusing, but it earned her a second slap. There were a few more
after that, Goddess among them, each of which earned her another slap. By
the time my Heathyr finally stumbled upon Countess, her face was nearly as
red as her corset, and her mood as black as her nails!"

Our guest growled. "Amusing, but hardly a test of a slave's devotion."
Suddenly, he grabbed my head again and forced me to swallow his entire
penis. A part of me thrilled at being used to roughly, even as I lamented
the fact that he wasn't bigger. "What did you do to break her?"

She smiled. "Take that nasty thing out of her mouth, and I'll show
you."

Instead, he began thrusting into my mouth again and again, never
releasing his hold upon my head.

"Nathaniel."

I felt his cock begin to swell. I panicked, but his grip was too firm
to allow me to pull away.

"Nathaniel." The Countess didn't need to raise her voice. Her tone was
enough to convey her anger.

At least, it should have been. Our guest just ignored it and began
fucking my face.

"I thought I made myself clear." I couldn't see, but it sounded as if
the Countess had stood up from the couch. "The last thing she needs in her
condition is to be subjected to your testosterone laden sperm."

When I looked up into his eyes, I saw the anger . . . the defiance . .
. the challenge in his glare.

"My boys always swallow."

"Heathyr is NOT one of your boys. She is mine, and you would do well to
remember that."

Our guest's only response was to hold the Countess' gaze as he exploded
inside my mouth. I knew this was forbidden, but there was nothing I could
do. He held me there, pressed tight against the base of his cock, forcing
me to hold my breath or swallow. I nearly blacked out from the effort, but
only the barest trickle slipped down my throat.

"You will release her. Now."

The moment he let go of my head, I pulled my head from his cock and
turned to face the Countess.

"My sweetest Heathyr." She came over to stand before me.

Kneeling before her, my mouth nearly overflowing with another man's cum,
I discreetly wiped my lips clean, being careful not to ruin my makeup.
Applying my foundation was a skill I'd mastered early, but matching the
right shade of lip-liner to my lipstick was still something I still fretted
over. While the Countess limited me to only the darkest shades available,
she always left me enough choice to make me work at making a decision.

Since I couldn't speak without swallowing, I nodded instead.

"I am so proud of you." She crouched down beside me and licked the trail
of cum running from my mouth. "Give it to me," she commanded, "that you
might be spared the contamination."

The Countess pressed her lips against mine and pulled my head forward. I
felt every drop of hot, salty man-cum slide across my tongue, over my lips,
and into her mouth. As we kissed, she probed my mouth with her tongue and
licked the remnants of cum from inside my cheeks. When she broke away from
our kiss, I found myself wanting to cry out for more.

She stood up to face our guest. I watched as she pushed three fingers
deep into her mouth, coated them with her second-hand cum, and then wiped
it across his face.

He laughed. "I guess I deserved that."

The Countess spat the rest at his feet, but otherwise ignored him.
Instead, she looked down at me and smiled. She began tying back her long,
lustrous black hair and nodded softly.

"You know what to do."

I felt a thrill of nervous anticipation run through my body as I rose
slowly to my feet. Although I'd participated in the ritual dozens of times
since the Countess first initiated me into her world, it never got any
easier. I truly was a little sissy girl when it came to anything
pain-related, but I would do as I was told, and take pride in doing it.

Before I could present myself to her, I had to struggle out of my tight,
binding, body-hugging leather skirt, without disturbing the equally binding
corset I wore overtop. Although it flared dramatically about my legs, the
high waistband was laced as tightly as my corset. Once I was free of the
soft, supple leather, I returned to my knees before the Countess.

Hands clasped behind my back, I lowered my head and stared at her feet.
"If it pleases you, Countess, your slave presents herself for inspection."

The only indication I had that she'd heard me was the touch of her
riding crop on my back. The Countess traced circles across my body with
it, teasing and tickling me, then gave me a solid `whack' when I wasn't
expecting it. It was the same with my legs, my arms, my front, and
especially my tiny, imprisoned penis. She loved to stroke and fondle it
with her crop, to make me gasp in pain/pleasure as prison grew too tight,
then slap me hard and watch me flinch.

"Hmmm . . . adequate, pleasing almost . . . but disappointing in one
tiny area." Even though I knew what was coming next, I'd never found a
suitable way of preparing myself. "Those nipples are far too tiny for
slave of mine, Heathyr. You should know by now that I like them big and
round."

"Yes, Countess. Please forgive - ah!"

As the hot wax began dripping from the candle onto my right nipple I
held myself rigid. If I was perfectly obedient, and kept my back arched
just so, the blood red wax would seemingly enlarge my nipple by three or
four times it's original size. The Countess was, among other things, an
artist, and her wax nipples were nearly indistinguishable from the real
thing.

The second nipple involved less pain than the first, but far more effort
on my part. By now the strain on my body was near the breaking point, and
I just wanted to scream in release. However, even the shallowest breath
could foul the Countess' masterpiece, so I literally had to place my life
on hold until she was finished.

In the end, though, the triumphant smile on her face made it all worth
it. As our guest looked on, she motioned me towards the floor. "On your
back, please, Heathyr - we don't want to mess your pretty new nipples."

I took my place on the floor. She stepped forward and placed her legs
on either side of my face. I watched, breathless with anticipation, as she
slowly lowered herself towards me. From my angle, the dark burgundy velvet
of her dress was like an erotic mask, ready to swallow me into its
mysterious darkness.

Once she came to rest upon my face, I knew I had but seconds to perform
my duties.

Using only my mouth, I had to coax the red satin panties from the
Countess' pussy and hold tight as she stepped out of them. I had no idea
whether it was the material, or whether she preferred them that way, but
they always seemed to be lodged deeper inside her slit than you would
expect from normal wear. As a result, it took a great deal of careful
licking, kissing, and biting to perform my task - and the intoxicating
aroma made for a difficult . . . distraction.

As she began to rise, I used my tongue as an anchor until I could feel
the first bit of space opening between us. Then, when I knew her tender
labia were safely out of harm's way, I bit down and helped the Countess
remove her panties.

"Very good, Heathyr. It's not often that you're successful on the first
attempt."

Her smile of pride was like the most potent aphrodisiac. No matter how
much I enjoyed a particular duty, it was her pleasure, her satisfaction
that I craved. Before I had time to return the smile, however, her naked,
dripping pussy was rapidly descending once again. The Countess would be
looking for pleasure this time, for the kind of oral worship that only a
helpless slave can provide. By alternately smothering and riding my face,
she was often able to coax out a string of orgasms to last the afternoon.

Our guest cleared his throat. "Really, Countess. This all seems pretty
tame." "Hmmm. There was a time that Heathyr thought so too." Suddenly, she
reached down, grabbed hold of my head, and pulled it into her sex even as
she forced herself down onto my face with all her strength. As I clenched
my fists and held my breath, I heard her tell our guest, "She knows better
. . . now."

With that, she released her grip and spread her legs so that all of her
weight was resting upon my face. Even though I knew what was coming next,
there was no way to prepare. My entire body snapped rigid as she began
dripping hot wax along my sissy-clit, causing me to squirm and struggle
beneath her. She was devilishly clever in the application, spotting me
randomly with the hot wax so as to keep me off my guard. At the same time,
she continued to enjoy my oral worship, which she always maintained was
more pleasant because of my squirming.

Even then, the Countess was not done. During a particularly long bout
of smothering, she snapped the blood red candle in half and began inserting
it into my sissy-pussy. I wasn't expecting the final intrusion to come so
quickly, and didn't have time to prepare myself. Instead of relaxing my
muscles and welcoming the assault, I was thrown into a renewed series of
near-panicked struggles and muffled cries that had the Countess chuckling
in dark delight.

"Mmmm, you squirm soooo well for a slave, Heathyr!"

I felt her thighs begin to quiver against my cheeks and knew the end was
near. Desperate to bring her over the top, I ignored everything else and
focussed on her pussy. I was completely immersed in the smells and tastes
of her sex, and there was truly nothing more exquisite in all the world. I
began licking and sucking like a madwoman, forcing my tongue so far inside
her that it hurt. My lips were swollen where I'd bitten them, but still I
continued to strain upward and coax her closer to climax.

That was when she upended the candle and literally began raining hot wax
down upon my penis.

"Unnngghhhhaahhhhhhh!" I screamed into the Countess as my own orgasm
crashed into my penile prison, only to be stopped by a seal of wax. That
prolonged my orgasm painfully, making it feel as if the cum was washing
back through the rest of my body.

"Yes! Yes! Yes!" She literally shrieked as her own climax washed over
her. Again and again she ground herself against my face, prolonging her
own pleasure while rewarding me with the explosive spray of her forbidden
juices. By the time her orgasm exhausted itself, the Countess had sheathed
my entire penis on hot, red wax - a feat that seemed to impress even our
guest, if his low chuckle of approval was any indication.

Although I was nearly rendered senseless, I could hear her breathing
heavily above me. "Now do you understand, Nathaniel? Breaking Heathyr is
not like breaking one of your pathetic, mewling boy-slaves. Pain and
pleasure . . . male and female . . . submission and reward . . . there
are so many more facets involved."

"It's still not quite heavy enough for my tastes, but I can see your
point." The Countess shook her head and laughed. "You still do not see it,
Nathaniel." She stood up from my face and smiled down at me. "You know
what to do, Heathyr."

As their conversation continued, I dug my nails into the exposed based
of my sissy-clit until it hurt. As it softened within its wax prison, I
felt the rapidly cooling wax give way with a series of snaps and tears.
Once I was completely soft, I pushed it down, as if I were going to tuck it
between my legs, and slowly pulled the wax sheath away from the head.

"When I take Heathyr this way," the Countess continued, "there is a
spiritual and emotional bond formed between us. She is a slave remade in
my own image - nourished by my sweat, my sex, and my golden wine."

I felt the dammed reservoir of cum drain out of my sissy-clit into the
wax sheath. It never ceased to amaze me how oddly submissive it felt to
just allow it to drip from sissy-clit, instead of having it forcefully
ejected in orgasmic spurts.

The Countess came over to take the perfectly formed wax cock from my
hands. "Thank you, Heathyr. You always do make me quite thirsty."

With that, she tipped her head back and let my spent sissy-cum flow into
her mouth. She made quite a show of enjoying it, even going so far as
break the wax in half and lick the insides clean. This was definitely
something new, but I recognized that it was all for our guest's benefit.
She had, after all, spit his own cum at his feet in disgust.

I nearly fainted in ecstasy as I watched her tongue lick the last
remnants of my sissy-cream from her full, red lips. She then returned her
attention to our guest. "It's something that no amount of physical pain or
pleasure could ever achieve in your . . . boys."

"You can stop now, Countess. I am convinced." As our guest rose from
his chair, he propped a small, black business card upon the mantelpiece.
"I am sure Francis will not like it, but you have won. Congratulations."

That said, he took his leave of the Countess' presence.

I sensed I was missing something. The Countess' affairs were none of my
business, but the strangeness of the encounter had made me curious. I, of
course, knew better than to ask, but she saved me the trouble.

"Heathyr? Join me on the couch for a moment." She certainly didn't need
to ask me twice. I beamed with delight as I crawled onto the sprawling
leather couch and snuggled up beside her. Tender moments like this were
far and few between in our relationship, but that only served to strengthen
the bond between us. I loved her as much for who she was, as for who she
was allowing me to become.

"You made me very proud today, Heathyr. When I first came to Francis
with my . . . request . . . he insisted that you weren't ready. He
refused to accept how far you'd come in such a short time." She chuckled
softly. "I offered to prove him wrong."

As she stroked my hair and kissed the back of my neck, the Countess
filled me in on the details of her wager - and the prize. The wager itself
was simple: all I had to do was prove my femininity to a neutral observer.
It had taken a long while to agree on Nathaniel, but his reputation as one
of the best slave-trainers around sealed the wager. Of course, the fact
that he only trained slave-boys had seemed to give Francis the edge, but
the Countess was confident I could convince even him.

"Then I did well, Countess? I made you proud?"

"That, and more." She grinned as she pushed me to the edge of the couch.
"Fetch me the card he left on the mantelpiece and return to my embrace.
Quickly."

I scurried to do her bidding, and then settled myself down in her arms
again. "Originally, Heathyr, I'd only approached Francis about fulfilling
one of your immediate desires." She caressed my chest, my face, and my
throat. Although the hormones - natural, prescription, and second-hand
from the Countess herself - were slowly working their magic, I still had to
do a lot of work to help nature along.

"Thanks to his own stubbornness and your delightful performance," she
told me, "we need not settle for just one." The Countess rolled atop me and
began slowly peeling the wax from my nipples. "We can discuss that in more
detail tomorrow, though, when we pay Doctor Francis a visit in his office."

With a nervous smile on my lips, I looked into her eyes and asked,
"Doctor?" "Yes, a Doctor." The Countess turned herself around and began
lowering herself over my face again. "Doctor Francis, plastic surgeon."
She pressed the damp lips of her pussy to my face, then suddenly pulled
away. "Oh, and did I mention he is the leading specialist in sexual
reassignment surgery in all of North America?"

My startled gasp was swallowed by her vagina.

"Hmmm." The Countess chuckled softly. "Didn't think so."