Chapter 8 - A slave in prison - John's story
My first visit to the penal island was an event that I didn't know whether to
look forward to, or to dread. Even though I was almost exclusively forced to
serve only males sexually, I was still apprehensive about being used by so many,
and for such a prolonged period. When I was delivered to the island, after a
long trip by both car and boat, my fears grew and grew. The footman left me
tethered to a post on the dock in the wee small hours of the morning. I was
completely naked, my hands were cuffed behind my back, and my prick was bent
double, with its head locked by its ring to the one behind my balls, my normal
form of enforced chastity. I flushed with shame when the keys to my bondage were
hung from my right nipple ring, and an envelope to the King of the island was
clipped to my left nipple ring.
My heart jumped in fright when I saw two huge, muscular black men, dressed in
prison denim, approaching me. One of them untied my leash from the pier post,
and I was led away. Neither of the men said a word to me, or even inspected me
all that closely. I was led to a large building well back from the shore, and we
entered through large double doors. The next thing I knew, I was being prodded
into what appeared to be an ornately furnished apartment. I stood in the centre
of the room while one of the men disappeared through another door. He returned
after a few moments, and I was ushered into another room, this one well lit, and
occupied by two people. One was an enormous black male, dressed in black leather
from head to foot. His huge, muscular frame was beautifully proportioned, and
the enormous bulge between his massive leather clad thighs promised a penis of
truly monumental proportions and, despite myself, I found my mouth begin to
water with sexual longing.
Crouched at this massive male's feet was what I at first thought was a girl. It
could not be, of course, this was an exclusively male prison. On closer
inspection, however, I realised that the creature was a male. He was naked
except for sexy feminine lingerie, and I could see a set of male genitals
hanging between his legs. The boy's penis and testicles were the smallest I had
ever seen, smaller, even, than a pre teen male would normally possess. What was
even more bizarre was the set of full firm breasts that jutted out from his
upper torso. His hair was long and blond, and worn loose around his shoulders,
and his face was painted like a woman's.
I realised immediately, of course, that this creature must be one of the prison
bitches who had been hormonally feminised. The massive male dismissed the two
men who had brought me to him, then went about inspecting my trembling nudity.
"A fine specimen, don't you think, Trudy?" He commented to his feminised
companion, then, after unclipping both the keys and the note from my teat rings,
threw the keys down to the pretty boy still crouched at his feet, and suggested,
"Why don't you remove his bonds while I'm reading the Master's note, little
slut, then get him stiff so I can see what he has to offer."
The male, who I was to find out was the King of the island, then opened the note
and began to read. While he was thus engaged the creature quickly removed the
cuffs from my wrists then, crouching between my thighs, which I spread to
accommodate him, reached in and freed my cock. The thick stem flopped down from
my crotch, and the transsexual sighed with sexual excitement at the sight of it.
He grasped the thick shaft and began to slowly wank it, licking at its flaring
head with his soft tongue at the same time. In almost no time at all the sexy
creature had me stiff and throbbing. "Oh, Lord, he has a fabulous prong!" The
little transsexual cried, then he continued to tease and stimulate me while the
King finished reading the note, then he moved aside so that the King had an
uninterrupted view of my aroused sexuality.
"Lovely, just lovely, pig. The sight of that prick will have every bitch on the
island drooling!" He commented. "I hope you know how to use it." I blushed in
shame at his demeaning comments, but my blood was racing with submissive
excitement. I was further aroused, and shamed, when he asked me if I liked his
bitch, Trudy, and didn't I think he was pretty. I gasped out an affirmative
reply, not being used of course, to responding with anything other than the few
phrases I was permitted to use at the chateau. "Would you like to suck her
pretty little cunt, pig?" He asked, and before I could reply, he continued, "It
will serve to test your mouth's capacity to give pleasure, little piggy, and if
you manage to get her off she'll be so pleased that she'll beg me to make you
fuck her for my visual pleasure, won't you, you little slut?" He asked the
transsexual with a mocking grin.
The pretty little transsexual grinned lasciviously up at the King, and panting
with lust, replied, "Anyone with a prong as gorgeous as his must be able to suck
like an angel, I'm sure my lord!" Then, turning to me, he almost seemed to beg,
"You'll suck my cunt like it's never been sucked before, won't you, harlot!
You'll make me come, so you can fuck me for my King's pleasure, won't you?" I
smiled at the feminised boy with my own lust growing, and my stiff cock aching
with pleasure, and answered him, taking my cue from the King, and referring to
him in the female gender, "Oh, yes, Miss, I will suck your beautiful cunt with
all the passion I possess. I yearn to make you come!"
The King tired of our banter, even though from his expression, he was delighted
by our lewd exchange, and snapped with mock severity, "Well, get on with it! We
haven't got all day!" The transsexual, when he saw his Lord sit down on an
ornate throne like chair, moved over to him, and half laid between his wide
spread thighs, then spread his own slim legs wide, to completely bare his
smoothly shaven crotch to me. The King then unpopped a series of studs in his
own groin area, and the leather pouch that had hidden his own sexuality dropped
away revealing his massive penis and enormous testicles. I gazed at his semi
erect penis with almost painful yearning. It was at least as large as those
possessed by the chateau's male sluts.
The King allowed his bitch to rest his head on one of his mighty leather clad
thighs, so that the bitch could get his mouth to that fabulous log of male
sexuality, while I knelt between his wide spread legs. I wrenched my gaze away
from that magnificent black penis, just as the bitch's soft tongue lapped wetly
over its big juicy head, a surge of sheer envy washing over me and making my
cheeks flushing hotly. I dove my face down into the smooth crotch of the little
bitch and spread the plump cheeks of his arse open, baring his arse ring. With a
sigh of delight, I pressed my lips to that pungent little orifice, and speared
it with my agile tongue. I drove my long tongue deeply into the hot, spicy arse
pit, and lashed its writhing walls with feral passion.
"Oh, my Lord!" Trudy gasped, "The whore has driven his tongue up my hot little
cunt! I've never had a tongue so far up my cunt in my life. He's gone far deeper
than any bitch on the island ever has! I can almost feel its tip tickling my
tonsils! Lord, it feels so goooood! Sooooo gooood!" The transsexual squealed out
in sheer delight. I kept my eyes fixed on the limp little tube of the
transsexual's minuscule penis while my tongue lewdly washed out his hot arse
pit. It took a few minutes, but eventually I saw some movement in the tiny
prick. It twitched and, almost imperceptibly, began to swell just a little. It
was time to capitalise on what I had achieved so far.
I withdrew my tongue from the clutching arse ring of the young feminised boy,
and allowed my drooling mouth enclose his cock and balls completely. I sucked on
the soft prong with absolute passion, squeezing the tube, and the tiny head with
my soft tongue over and over, then lapping it insistently, and erotically. I
worked my mouth and tongue with single minded devotion. All the while I stared
up at the King's face, my eyes radiating with lewd depravity for his amusement.
Trudy's tiny shrieks of contentment soon became squeals of delight at the
exquisite sensations my submissive tongue was visiting on his quite
dysfunctional male sexuality.
"Oh, my King!" The pleasure filled bitch shrieked, lifting his head from the
King's almost fully erect penis, "The whore is sucking my clit like it's never
been sucked before. His mouth and tongue are so good! So clever! So divinely
sexy!" Then he dropped his head back down and engulfed the head of the King's
enormous penis completely in his stretched open mouth. I sucked and sucked, and
was rewarded by the tiny penis stiffening, slowly, but, never the less, surely.
I renewed the passion with which I sucked when I realised that I might actually
get the minuscule cock fully erect. My heart pounded with obscene lust. I
wallowed in the humiliation that filled me at the sheer perversity of my
actions. My heart soared with undiluted joy when, finally, the diminutive cock
was fully erect, and stood proudly, as stiff as steel in the transsexual's
crotch.
With sensations of sheer pride at my achievement washing over me, I allowed the
tiny prick to escape the hot wet confines of my mouth. While staring up at the
King with triumph in my eyes, I teased the length of the little cock, from its
base to its tip with the tip of my tongue, proudly showing off the stiffness my
talented tongue had aroused. My tongue lapped and flicked at the stiff little
prong, driving the transsexual towards unimaginable orgasm. I wallowed in my
triumph, pride filling my being. I would taste this creature's prick juice, and
would probably be the first, and only one to do so since he had been
transformed.
The tiny prick began to jerk and pulse under the relentless teasing of my
flicking tongue. I ensured that I gave the King an uninterrupted view of my
lascivious actions, and noted that his eyes were no longer staring mockingly
into my own, but were now fixed firmly on his bitch's cock, and were also
displaying wonder at what he was seeing. I smiled inwardly at this reaction, and
my own achingly hard stalk pulsed with the intensity of my burgeoning submissive
delight.
Trudy sucked on the King's huge prick head with unrestrained passion, mewled in
utter ecstasy when he climaxed. My tongue eagerly captured the tiny spurts of
creamy sex juice that gushed from the tip of his diminutive cock. His cock juice
tasted as sweet as ambrosia and, although he had precious little to surrender, I
surged with pleasure while I savoured the ambiance of the flow in my mouth
before drinking it down. My tongue teased the little pole of lust the whole time
that it gushed, my heart busting with pride at having caused it to do so. The
King expressed his utter amazement at the sight of his bitch coming. He, too,
thought that the days of such an event were over for the transsexual.
"By God, harlot!" He cried, "You must have the most talented mouth on earth. I
would have sworn that Trudy's little clit had spat for the last time months ago.
Amazing! Just amazing!" Before he could go on he was interrupted by his bitch,
just as I engulfed his rapidly softening little prick into my mouth, and sucked
for every last drop of the sweet elixir it had to surrender, "My Lord! My Lord!
Please let the marvelous whore fuck me! Please, my Lord! Surely his lewd,
lascivious mouth has pleased you! Please have him fuck my hot, aching little
cunt for you!" Trudy begged plaintively while I continued to suck passionately
on his now soft little cock, and tiny empty nuts.
"Fuck the little bitch, harlot! Fuck her deep! Fuck her hard! Fuck her until she
can't walk straight!" The King cried commandingly. I reacted to this with sheer
delight. It was so long since I had fucked an arsehole, that I had almost
forgotten just how pleasurable it was to feel a hot tight arse pit clutching at
my cock. I raised my face from the transsexual's sated prick, grabbed his ankles
in each hand, dragged his body back from his King's lap, pulling his mewling,
protesting mouth off the King's now strongly erect penis, and bent his shapely
legs back along his prone body. I reared up my own body and, with a squeal of
delight, drove my own pulsating prick through his hot, tight little arse ring,
and into the depths of his elastic arse pit in one full stroke, burying it to
the hilt.
I was mildly surprised at the ease with which my prick went in, then realised
that this creature was the King's personal bitch, so his arsehole was accustomed
to being reamed out by his monster penis, and mine, even though large, was no
match for the King's marvelous specimen. The bitch drew my face down to his, and
glued his lips to mine in a searing kiss. While our tongues dueled wetly, he
drove his round bottom up to meet each of my long full strokes. I pumped the
bitch slowly, his plump tits crushed into my chest, and gave him a taste of his
own sweet cock juice while our tongues entwined, while I delighted in the sheer
obscenity of my situation.
Suddenly the King grabbed a handful of my hair and dragged my head up until my
gaping mouth was a mere inch away from the juicy head of his fabulous, throbbing
penis. My eyes widened in wonder, and utter joy at the sight of his magnificent
penis, and my nose was filled with its manly aroma. "Suck on this, harlot!" The
King sighed, "Suck on this while you fuck my little bitch's brains out! I have
to feel the hot tongue that managed to bring the lewd bitch off! I have to!"
I leant forward, and kissed the spongy meat of the head of the King's wonderful,
manly penis with true love and devotion. I would give this man a sucking that he
would not soon forget, but more importantly from my point of view, a sucking
that would have him craving for more. I opened my mouth wide, and swallowed the
juicy penis head, thrilling to the rich flavour of the pre-cum seeping from its
dilated slit. Then I slowly began to consume the stalk of lust. My lips crept
slowly down its throbbing length and I swallowed and gulped wildly while its
massive span filled my mouth and throat to almost tearing point. My breath
became ragged, and I began to question whether I would be able to completely
swallow the huge slab, but this thought only spurred me on to even greater
efforts. I would not fail in my self appointed task. I would take it all in! I
had to! I longed to!
Stars of pleasure exploded in my fevered brain when my nose was finally pressed
firmly into the forest of crinkley hair at the base of the King's fabulous
penis, and its entire, throbbing length was buried in my madly convulsing mouth.
I stilled my mouth for as long as I could, and basked in the delicious obscenity
of my situation, before the need to draw breath overcame me,. My mouth and
throat filled to absolute capacity with hot, throbbing, black penis, while my
own achingly rigid lust stalk plunged back and forth, with sensuous slowness, in
a equally hot, tight arsehole. This was surely heaven for a submissive whore
like myself.
Little Trudy rolled and thrust his plump, round bottom up to meet each stroke of
my cock in his churning arse pit like a harlot, and I slowly plunged my mouth up
and down on the King's fabulous penis in perfect time. "By the stars of
whoredom, you lewd harlot!" The King cried in passionate excitement. "You have
the mouth of an angel! You suck like the hottest whore in history! No one has
ever taken my full length! It is impossible! But you, depraved bitch, have
achieved the impossible! My joint feels like it's being consumed by a pleasure
machine! The Master has instructed that you be contained to three spittings a
day at the maximum, lascivious bitch. And you can have one of them now! When I
feed your deliciously obscene mouth my load, you may flood my little Trudy's
wallowing arsehole! Fill the horny bitch to the brim!"
A surge of sheer happiness flooded me at the King's announcement. Knowing the
Master's sadistic nature, I had already steeled myself to a week of sexual
excess, despite which I would be probably denied any relief at all. I plunged my
pulsating prick in and out of Trudy's clenching arsehole with ever increasing
velocity, and my mouth sucked passionately at the King's rapidly peaking penis
while, at the same time, I fucked it passionately with my adoring throat. The
King began to cry out his pleasure as his orgasm began to build to the
inevitable explosion.
A roar of triumph was ripped from his gaping mouth when the first powerful spurt
of his rich creamy penis elixir splashed profusely into the back of my wildly
gulping throat. I was overwhelmed with the flavour of male sexuality, helplessly
basking in my lewd obscenity. I sucked on the spurting head of the King's
ejaculating penis in utter rapture. Then my own pleasure filled cock exploded in
the hot confines of Trudy's elastic arse pit. I gulped down an ocean of
gloriously delicious male cum while my gushing prick flooded Trudy. I lost
myself in my joy and elation while time seemed to stand still, and wave after
wave of perfect ecstasy completely consumed me. When the King's climax began to
wane I don't know how I managed it, but my lips plunged back down on his
softening pole of lust, and I milked the beautiful penis for every last drop of
its exquisite essence.
Trudy's hot arsehole also milked me completely dry, and my tight, smooth balls
softened slightly after the force of my climax had emptied them. Finally my
mouth merely suckled tenderly on the thick head of the King's spent penis, and I
wallowed in the divine sensations of his bitch's arse ring squeezing my own
sated cock, which, incidentally, had hardly softened at all despite the power of
my orgasm.
The King stood up, removing his cock from my mouth and leered down at us. "You
depraved harlots," He sighed happily. "It's time to introduce the debauched
harlot to the population, so that they too can sample his perverted talents.
Take him away, Trudy, clean him up, then dress him in his bitch's costume. When
you're ready bring him back to me, and we'll be on our way."
Trudy took me to a bathroom and quickly washed my nudity. By this time my cock
had softened, and he efficiently cleaned it after its visitation into his hot
arse. When he was satisfied he equally quickly cleaned his own body. Then he
placed a lacy garter belt around my hips, and smoothed pink silk stockings up my
legs. I thrilled to the sensual feel of the material on my skin while Trudy
clipped the garters to the tops of the stockings. A pair of high heeled shoes
were strapped to my feet, and Trudy giggled while he watched me teetering
around, trying to get used to walking in the ridiculous shoes. He then made up
my face with subtle professionalism, transforming it from openly masculine, to
almost sensual femininity. I blushed with delicious shame at the transformation
he managed in my appearance, but after all, I was a whore, and it was only right
and proper that I should also look like one.
We returned to the King's chamber and, after expressing delight at my
appearance, he led us off. We entered a large communal room, obviously the
prison's mess hall, and I was deposited on a small stage at the top end of the
room, and displayed to the hundreds of men seated at the tables, eating their
breakfast. In the short time that it took for the King to set himself up before
a microphone I was able to survey the room. Many of the men were dressed in
standard prison denim, and many were dressed as females. It appeared that the
majority, but by no means all, of the denim clad men were black, while the
opposite was the case with the ones in drag. Some of the men in female clothing
were obviously undergoing hormone treatment, although, from what I could see,
none of them were as advanced as Trudy. Others in feminine attire were quite
obviously completely male in every other respect.
I stood in the centre of the stage, my legs slightly parted, and my hips, almost
imperceptibly shimmying. My long thick prick swaying to and fro, ever so
subtlety, framed so sexily by pink silk and satin. The complete attention of all
the prisoners was now firmly fixed on the stage, and the King began to make his
announcements.
"Let me introduce this whore, supplied so kindly by the Master." He began, "As
could be expected, a harlot trained by the Master is likely to be completely
depraved, and wonderfully eager to please. I can assure you, my people, from
personal experience, this is true. To give you some idea of the harlot's supreme
talents, he has already managed to bring the Trudy bitch off with his mouth. I
had thought that this was now impossible for my little bitch, but the whore
managed it beautifully. So, my friends, the bitches among you who have chosen to
follow Trudy's example, and transform yourselves into femmes, will be in for a
treat, should your betters allow you to receive the attentions of the harlot's
supremely talented mouth."
I flushed with a mixture of deep humiliation, and deliciously submissive, wanton
lust while the King spoke to the multitude. I found my hips rutting and rolling
with increasing depravity. My own inherently lecherous nature was taking over
and, while my cheeks still burned with the flood of humiliation that swept
through me, my long thick cock stiffened and swelled until it was fully erect,
and arched out lewdly from my smooth crotch. I had no more hope of controlling
my prick's lewd reaction to my degrading circumstances, than of flying to the
moon. It was my nature to flaunt my lewd obscenity whenever I was the chance to.
The King, noting the wanton reaction in me to my shame, and the sheer depravity
of my circumstances, chuckled gleefully, "Just look at the bitch's perverted
display. He can't wait to get his mouth around a hot cock. He can't wait to have
his whore arse speared with stiff prick! And he'll soon get his wish. The Master
has permitted us to punish the whore should he not completely please us with his
obscene service. I don't, however, think this will become a necessity, given my
brief experience of his wanton perversity, not to mention utterly wonderful
skill at his job. I suppose, perhaps, that he might flag with exhaustion at some
stage. We shall see."
My mind was filled with conflicting emotions. My stiff, throbbing prick swaying
lewdly from my now lasciviously rolling belly, while I wrestled with my
submissive senses. I was caught in an impenetrative quandary. I yearned to be
punished! I didn't think that I could live for a whole week without being
punished! But I could never even contemplate deliberately lowering the standards
with which I would work for the prisoners' pleasure. I could not even conceive
that I might display anything less than complete and utter depravity in my
sexual service. I was too well trained for that to be even a slight
consideration. I would just have to take things as they came, I convinced
myself. In fact, as you will learn, I needn't have worried.
"The harlot will be installed in the theater each day, from ten in the morning,
until ten at night. He will be controlled by the Trudy bitch, who will ensure
that none of you try to monopolise his time. I don't want to hear of any
arguments in this respect. You will defer to my bitch, as if it were I making
the decisions. Now, one last thing, the Master has instructed that the whore
only be permitted to empty his nuts three times a day. In view of this I think
that we must make some of those events a spectacle, so that all can enjoy the
sight. Trudy bitch is charged with dreaming up suitable scenarios for these
spectaculars."
The King concluded his announcement by instructing Trudy to take me to the
theatre. He led me from the stage, my achingly erect prick swaying obscenely out
from my mincing groin, much to the amusement of the dining prisoners, and, of
course, to my extreme embarrassment. Trudy led me down a long hallway to another
set of double doors. He pulled these doors open and urged me into the theatre.
It was not a theatre in the normal sense, only in that, instead of rows of seats
the large viewing area was populated with couches and settees, and all of these
seemed to be upholstered in a rubber like material.
Trudy led me to one of the couches near the theatre's large stage, and drew me
down onto its smooth surface. He reached down and squeezed my throbbing prick,
and sighed, "Aren't you the hot one, whore? It was so deliciously wanton when
this lovely hot prick got stiff while you were on the stage." He cried, stroking
my cock tenderly. "What are you looking forward to most, darling harlot, all the
cocks you'll be sucking? All the cocks that will fuck you? All the arseholes
you'll be allowed to fuck? Or is it the mouths that might suck you?" He asked
with a grin. All I could do was to tell the pretty transsexual that I wanted it
all, and would not enjoy any one, more than the others, just so long as they
kept coming.
"You'll bring off all the femme sluts, won't you, darling whore?" Trudy begged.
"I've promised all I've spoken to that you will, and you will, won't you?" I
told him that I would, but I wanted to bring him off more than anything else. I
flushed with happiness when the little bitch informed me, with a chuckle of
delight, that the King had promised him the third orgasm of my allowable three
each day, and that he was going to suck it from me in bed each night after the
day's activities. I responded by telling him that I would also suck him off as
well each night. Trudy further raised my lust and yearning when he told me that
my first climax would nearly always be extracted by his hot little arsehole each
morning, for the amusement of the King.
My real surprise came, however, when Trudy informed me that the King had told
him that he too, was going to suck me off. He explained that the King rarely
sucked cock, and that I should feel deeply honoured. He explained that the last
cock he had ever heard of the King sucking off was, in fact, his own, and this
had happened when Trudy informed her royal lover that he wished to be feminised,
so that he could serve him sexually with more passion and submission, as a
female slut.
We talked on until the doors opened, and a bevy of prisoners wandered into the
theatre. Almost before I knew it my mouth was sucking at the tiny penis of a
transsexual, and a hot cock was sawing in and out of my pleasure filled arse
pit. I worked on the soft penis with all of my talents, and soon had it stiff
and hot, and the small titted bitch was squealing with pleasure. The massive
cock poured its juices into my welcoming arse pit while the little penis
surrendered its succulent juices to my overjoyed mouth.
A hot mouth sucked my cock passionately when another drove past my lips and
buried its drooling head down my gulping throat. I sucked, and was sucked until
this cock poured its cream into my adoring mouth. On and on it went. I was
passed from group to group, and served them all with joy and happiness. Each
time my arse pit became too sloppy Trudy supervised its cleansing, generally by
the eager mouth of a femme slut. I was lost in my wanton lust, consumed by my
lascivious excess. I fucked cocks with all the passion of a born harlot, sucked
stiff, hot penis with utter joy, and drank gallons of creamy, aromatic cock
cream, relishing every drop.
At one point, while I was being fucked by a large black man, whose white bitch,
not a femme, was passionately sucking my throbbing prick, another huge black man
mounted the stage, dragging a naked white femme slut with quite large tits
already evident on his slender chest along with him. He stood in the centre of
the stage and positioned the white femme so that his rounded arse faced the
crowd. The man then began to spank the femme's arse cheeks as hard as he could.
The femme cried out in pain and sobbed to her tormentor for mercy. This only
seemed to urge the man to even more cruel spanking, and his open hand was making
loud cracks each time it pounded into the reddened flesh.
"Do you like to have your little arse spanked, harlot?" The man fucking me asked
as he drove his long, thick, hot penis into my arse pit to the hilt, and his
thighs slapped into my bottom cheeks softly. "No, Sir!" I panted in my wanton
pleasure. "I don't like to have my arse spanked. I love to have it savagely, and
mercilessly whipped, Sir! Would it please you to whip my arse, Sir! Please, sir!
Please, Sir! Whip my arse hard with a heavy belt, if that would give you
pleasure. I would love to suffer at your hands, Sir!"
My lewd, and utterly submissive pleading soon had the man emptying his balls
into my churning arse, and his bitch sucking me so passionately that I had to
concentrate hard to prevent my prick from spitting into his hot mouth. The man
pulled his sated cock from my arse, and called to Trudy. He explained to the
beautiful transsexual that he would like to whip my bottom, and that, not only
had I agreed to this, but I had actually begged him to do it. Trudy was a little
skeptical, however, not knowing my masochistic urges. He looked to me to confirm
what he had just been told.
"Would you really like to be whipped, sweet harlot?" He asked incredulously.
"Oh, yes! Darling Trudy!" I gasped my excitement obvious in my pleading voice.
"I would adore it if you would permit this gorgeous strong man to whip my arse
to shreds. Please, sweet Trudy, let him whip me! Let him!" I begged with heart
tugging fervour. "I can't believe that you really want this." Trudy rejoined,
then continued, "But I will permit it, just to spite you, and to teach you a
lesson." He thought for a few seconds, "It's almost time to have you brought
off, little whore, so this can serve as the entree, so to speak!"
I had to convince the pretty little transsexual that I really did want to be
whipped. He had to be made to understand what exquisite pleasure I derived from
my pain, if I was to be able to continue to receive at least a little punishment
each day. I knelt before the delicious creature, and kissed his feet in utter
submission, then begged, "Do you have a cock softener, Miss Trudy?" She replied
that she thought that there was one about somewhere, and ordered one of the
other femmes to go and find it, and to bring the punishment strap, while he was
about it.
It took the femme a few minutes to return with the two instruments, and I used
this time to try to further convince Trudy that he was really acceding to my
fervently felt desire, and not punishing me unnecessarily. I don't know whether
I succeeded or not, but I can promise that after the event he certainly was
convinced. My heart was pounding with eager anticipation, and my masochistic
juices were beginning to run hot while I buried my face in his crotch and sucked
passionately on his soft little penis, sucking at it with such enthusiastic
emotion that he must surely realise that I yearned for the whipping I had
pleaded for with all my heart.
Suddenly my kneeling body jumped with shock. The freezing rod of the cock
softener touched my hot hard prick, and was run up and down its length firmly.
My aching prick reacted to the freezing rod by collapsing almost immediately. I
dragged my face from Trudy's delightful crotch when the femme wielding the rod
stopped as soon as he had seen my prick go limp, and pleaded helplessly, "Sweet
Miss!" I cried, "Don't stop! Don't stop! My prick must be rendered utterly limp
and soft. And my nuts too, treat the fat nuts with the rod. Make them soft and
slack as well!"
The transsexual re-applied the rod to my hanging cock shaft, and ran it over and
around my balls as well, giggling while watching my freezing cock get softer and
softer, and my balls to seem to shrivel up. When I was satisfied that my cock
and balls could not get any softer I called for the femme to stop, and stood up,
my prick and nuts hanging slackly from between my thighs. Trudy gazed in awe at
my crotch, and I could see the consternation on his face. He obviously enjoyed
looking at me when completely aroused, and was not too happy to see me in this
state. Or perhaps he was psyching himself up to punish me, for not being stiff
and proud in his presence, at least that was my opinion.
While, Trudy, and the huge black man who was going to whip me, and I mounted the
stage the word had obviously been spread around the prison concerning what was
about to happen, and many new prisoners were seen to be filling the theatre. I
got my first look at the punishment strap, and my pulse raced with fear, and
masochistic delight. The strap was six feet long with a grip at one end. It was
made of thick, but flexible leather, about a half an inch thick, and two inches
wide, and looked utterly brutal. I shivered with submissive lust, dreaming of
the beautiful pain that it would surely bring me.
Once on the stage I turned away from the growing audience, spread my legs wide,
leant my torso down low, and braced myself with my hands on the floor. This
presented my bare bottom as the highest point of my body. My utterly softened
prick and nuts hung loosely down from my splayed open fork. I peered from
between my legs at the sea of faces watching me expectantly, and flushed with
submissive pride. My pain and punishment was once again the subject of
entertainment. I loved it! Loved it so!
I glanced up at the huge black man casually swinging the brutal strap about. He
grinned down at his defenseless target with sadistic glee, obviously looking
forward to pounding the submissive flesh with the cruel strap. "Please, Sir!
Please, Sir!" I begged passionately, "Thrash my wanton arse slabs savagely! Make
the lewd mounds throb with pain! Beat my lascivious bottom hard! Please, Sir!
Please, Sir!" I pleaded with almost unearthly yearning. I needed to suffer! I
had been granted sexual excess without bounds, and I needed to feel the pain to
balance my lewd wanton depravity with the sheer masochistic nature of my
character. It was not right to be allowed so much pleasure, with so little pain
and suffering.
The massive man swung the brutal strap up, and brought it down, with a loud
crack, onto my swaying arse slabs. I let out a muted yelp as the fire of the
stroke spread across my firm meat. He quickly brought it down again, and I
wallowed in a fresh surge of burning pain. But it was not enough, so I decided
to goad the man administering the whipping. I cried out derisively, "It that the
best you can do, Sir! I've been whipped harder by girls! What are you, a wimp or
something!"
The huge man roared in anger, and his eyes blazed with rage. I was questioning
his manhood in front of his colleagues, and he would make me pay. He gripped the
whip handle in both hands and brought the strap down on my arse with such force
that my body actually jumped in the air, and the pain that assailed my tormented
bottom was truly awesome. I squealed in anguish when the following stroke was
delivered with even more power. I sobbed out my gratitude, "Thank you, Sir!
Thank you, Sir! Whip harder, Sir! Whip harder!"
The cruel man certainly answered my pleas with even more savage whipping, and
tears of pain and anguish were soon pouring from my eyes, complimented by a
constant stream of squeals being ripped from my gaping throat. The audience
watched me being savagely punished in almost complete silence. But it was not
only the erotic sight of a pair of up thrust arse slabs being brutally beaten
that was demanding their attention, but also what was happening between my
spread legs. Almost from the first stroke of the belt my prick had begun to
swell. By the time that the man had been goaded into really belting my pain
soaked cheeks, it had visibly grown, and now that my squeals were of real pain
and suffering, my prick was again fully erect, and throbbed wildly between my
shuddering thighs. My swollen nuts were also once again tight and full, and
stood out from the base of my rigid stem.
The cruel, and still enraged man whipped and whipped, until my arse slabs were
deep red in colour, and were becoming badly welted. Trudy finally called a halt
to my punishment, much to my chagrin, for I was just about to plead with the man
to change his target from my wealed arse cheeks, to my bulging balls. But, on
reflection, it was probably just as well, for I didn't know what the
transsexual's reaction to this might have been, but it would have probably been
too much for him, and broken the spell of affection that had grown up between
us.
I remained in my position after the whipping ended, reveling in the burning ache
in my arse, and the throbbing ecstasy of my fabulously stimulated cock. I waved
both erotically for the benefit of the audience who were now buzzing with
excitement at what they had just witnessed. Trudy was busy organising the men
she had chosen to assist in my sexual release. He had had a low slung chair, of
the laylo type, brought up onto the stage. One of the two denim clad males was
instructed to recline, on his back on this chair. The male was already pantless,
and when he lay down his long thick penis arched up from his crotch. I was then
led over to him and Trudy assisted me to lay down on top of him, on my back. He
guided my arsehole to the penis, tenderly petting my red, welted bottom cheeks
at the same time. I sighed with delight when the hot, fat head of the stiff
penis forced its way past my tight arse ring, and its throbbing length sank
deeply into my welcoming arse pit.
Looking out into the theatre, while savouring the delicious sensation of a penis
filling me so beautifully, I noted that the prisoner who had whipped me so
deliciously cruelly sat with his bitch kneeling between his wide flung thighs.
His hands were entangled in the bitch's long hair, and he was driving his
enormous, erect penis in and out of his bitch's mouth with long full strokes. I
sighed happily. Any man who whips arse so savagely deserves to have his penis
passionately sucked for him. I only wished that it was my mouth that he was
using, and not that of his bitch.
A pair of ebony thighs then completely captured my attention as they were swung
over my upturned face, and my wide, excited eyes were greeted by the gorgeous
sight of a lovely thick, stiff penis being brought into range of my mouth. I
couldn't stop myself, and reared my head up so that I could press my lips to the
satiny skin of the head of the penis. "Don't be so greedy, whore!" Trudy snapped
quite angrily. "Control your obscene lust, until I tell you you can go!" The
penis was raised slightly, so that I could no longer get at it.
While he was arranging the three bitches, Trudy also called for two more
prisoners to join us. There was a rush to comply, but he only accepted two who
had already removed their pants, and sported nice stiff erections. Trudy
arranged for two of the bitches, the femme ones, to kneel on either side of my
prone body. The third, a male in girl's clothing, knelt between my, and the man
whose penis was buried up my arse's, thighs. He then gave them explicit
instructions as to their duties. Instructions that had my own pulsing prick
stalk throbbing with eager anticipation. The final two men were instructed to
kneel on either side of me, but much closer to my head.
Trudy appeared to be ready and, after guiding each of my hands to one of the
kneeling males' stiff, hot cocks, announced, "Our well punished little harlot
will now receive his reward. He will display the rutting obscenity of his
spitting prick to us for our entertainment. Regardless of the teasing that the
bitches at his crotch inflict he will not allow his cock to spurt until his
whore arsehole has managed to milk a load from the cock buried up it. It should
be entertaining, and will certainly test the talents of his whore man cunt. You
may now begin!"
Poor, naive Trudy. Still annoyed at me forcing him to have me whipped, and
thinking that he would make me pay! I suppose, of course, by not having a cock
big enough to experience the skills of my superbly trained arse pit, he could
not know that I would have to control its ardor, so that I could even properly
enjoy the rest of the activities that he had designed to bring me off. I sighed
with happiness when the lovely penis poised above my face was once again brought
into the range of me eager mouth. I swallowed a third of the hot hard meat, and
sucked on its throbbing head with measured passion, savouring the rich flavour
of aroused male sexuality.
The muscles of my stretched, packed arse pit squeezed its erotic invader with
consummate skill, but not enough passion to excite it to explosion too quickly.
Then my cock and balls erupted with divine pleasure. A hot, wet tongue began to
wash over my swollen balls, and two others began to flick up and down the length
of my pulsating prick with delightfully sensual efficiency. I tugged softly at
the erections in each of my hands, and settled down to enjoy the depraved sexual
overload that I was being so lasciviously subjected to.
How deliciously debauched it was. To be so dominated by strong male sexuality. A
stiff hot cock for your arse pit to pleasure, another buried in your mouth
feeding you with its tasty flavours, and two more for you to caress and stroke
in your hands. And all the while, three soft wet tongues teasing and stimulating
your own stiff, throbbing stalk, and hot, sap filled balls. Oh what joy! What
utterly divine obscenity. And to have it all be witnessed by a crowd of other
males. I was in sexual heaven.
I worked my arse pit with slow, erotic skill for ages, before the sheer desire
to pleasure the penis became too much for me. The cock in my mouth had swelled,
and was throbbing wildly, so I knew that it was about to explode, and I wanted
all the pricks I served to erupt as close to the same time as possible, so I
began to work my skilled arse with all the passion at my disposal. The throbbing
penis buried in it soon exploded, and filled my churning chute with a veritable
ocean of creamy cock juice.
The prick buried in my sucking mouth bathed my gulping throat with scrumptious
prick cream, and the two in my hands jerked wildly, and spat copious quantities
of cum onto the floor below them. Then my own orgasm erupted! Stream after
stream of cock elixir gushed from the flared tip of my spasming prick. The
bitches fought with each other to drink my offering. Their mouths, in turn,
covered my pleasure soaked cock head, in time to receive a powerful spurt of its
aromatic cream.
My orgasm lasted for ages, and I completely lost myself in the ecstasy of it. My
aching nuts were milked completely dry by the eager bitches, and my own mouth,
hands, and arsehole worked to totally drain each cock that they served. After a
minute or so of complete sexual frenzy it was over. The well drained penis
slipped from my mouth, and the two my hands had milked were withdrawn. The three
bitches, after sucking up ever drop I had to surrender, moved, reluctantly away,
and finally the softened pole that my talented arse crater had emptied oozed
from that sated orifice, and I was pulled to my feet.
Trudy smiled at my sated nudity slowly, his earlier annoyance now a thing of the
past. He was actually much more interested to see that my prick had hardly
softened at all despite the strength of my climax. Pleased, I'm sure, that I was
saving some for him. A quickly blinking of the lights in the theatre signaled
that it was time for all to retire to their cells. Trudy dragged me off to her
cell, well hardly a cell in the normal sense of the word, more like a hotel
room, or more accurately, a hotel suite.
We quickly showered and were soon in a passionate embrace in Trudy's big bed,
our nude bodies pressed closely together with Trudy's lovely big tits squashed
against my chest. Trudy eventually broke our soul searing kiss and, reaching
down between our bodies, grasped the hot hard stem of my aching prick and
squeezed it tenderly while whispering in my ear, "Why, sweet whore? Why did you
make me let that man whip your darling arse so hard?" I sighed contentedly, and
explained it all to the lovely transsexual, while her other hand caressed my
slightly welted, and still quite heated arse mounds.
"I might be the hottest, most debauched harlot ever, Darling Trudy bitch," I
whispered, "But above all, and first and foremost, I am Master's slave. And
slaves, sweet Trudy, exist to be punished. Slaves must be punished! Slaves adore
being punished!" I explained, my hard cock pulsing at the memory of my
suffering, then continued, "Not only am I the most depraved whore immaginable,
but I am also the most submissive, servile slave ever seen. I live to suffer.
Master has reduced me to a pain adoring chattel, and I love it! I adore it! I
can't live without it! And now, darling Trudy bitch," I breathed, reaching down
and cupping his tiny penis, and minuscule balls in my hand, "I'm going to suck
your delicious little cunt until you squeal, in pleasure, just to express my
gratitude to you for having me so gorgeously, and beautifully punished!"
I rolled onto my back, grasped Trudy around his tiny waist and dragged his
wriggling nudity on top of me, then turned his body until his smooth crotch was
immediately in front of, and above my face. In the dim light of the room I
stared at his tiny penis and balls, nestled so erotically between his slender,
feminine thighs. I sighed happily as I closed my hot wet mouth over the
miniature set. I allowed the tip of my tongue to tease the limp little tube of
the transsexual's penis languidly. I intended to draw out his pleasure slowly
and sensuously, to prolong his delight for as long as I could.
A shock of delight flooded my body when his hot mouth enclosed the top third of
my own achingly stiff prick, and he sucked passionately on the flared head. The
hard tips of his rigid teats grazed against my belly while he shook his big firm
tits with pleasure while he sucked. I had to steel myself against the intensity
of the stimulation of my hot throbbing cock. I intended to feed his eager mouth
with my outpouring of juice only when he too was spurting his sweet issue into
my own adoring mouth.
It seemed like ages had past before my flicking tongue drew any response from
Trudy's shrunken penis. But it finally began to have its effect, and the soft
shaft began to stiffen. When this happened I re-doubled my efforts, and my soft,
insistent tongue stimulated the hardening pole until it was fully erect, and
throbbed wildly against my working tongue. The transsexual's reaction was
immediate. His wild sucking on my pleasure filled cock head became increasingly
more and more passionate, and I throbbed uncontrollably in his ardent mouth.
I fought gamely to control my cock, and to stop the surges of cum that
struggled for release from my flexing balls. My tongue lashed his stiff little
penis with relentless accuracy until his muted squeals of sheer rapture heralded
the arrival of his shattering orgasm, and his creamy juice poured out into my
delighted mouth. I sighed in ecstasy when the first little gush signaled his
surrender to his pleasure, and allowed my own prick to explode in unison. Stream
after powerful stream of rich hot prick juice flooded from the tip of my
ecstatic cock, and it filled the pleasure filled transsexual's mouth to
capacity. Trudy gulped and swallowed wildly, and his hot mouth sucked with
complete frenzy until the strength of my outpouring inevitably began to ebb.
I sucked strongly on his rapidly softening little penis while Trudy drained my
balls completely, then collapsed, completely sated, on top of me, his big firm
tits squashing onto my palpitating belly. I tenderly lapped at his sated prick
and balls for a few minutes, and he kissed and lapped at my own satiated, and
now limp tube in response, while we both slowly came down from our respective
sexual highs. After a while Trudy wriggled around do that he could kiss me. He
whispered delightfully, "You suck like an angel, sweet harlot! I came so hard
that I thought that I would die from pleasure. I though I would swoon completely
while your big balls were feeding me their fabulous cum. So much rich virile
cum, my darling harlot! So much for me to drink! So much gorgeous cum! I loved
it!"
We drifted off to sleep in utter contentment in each others arms. The next
morning, after we had showered together, and were dressing in our erotic,
feminine lingerie, I suggested to Trudy that I get him stiff, so that he could
enter the King's presence in that sexy state. Trudy giggle with glee, but
expressed doubt that he could hold it for long. I replied that that didn't
really matter. It would be the mere fact that he tried that would please his
Lord. I knelt behind him, parted his firm round bottom cheeks, and plunged my
eager tongue deeply into his hot arse pit. The tip of my agile tongue quickly
located his prostate, and I stimulated it madly, my fingers efficiently
masturbating his soft little penis at the same time.
It took five minutes to get the transsexual stiff and erect, but I managed to do
it, and a flush of pleasure coursed through me. By this time, of course, my own
huge cock was as stiff as steel, and pulsed with sexual arousal. It was in this
state that we entered the King's chamber. Trudy flaunted her tiny erection with
pride as we stood before the King. He smiled ruefully down at us from his raised
throne, and commented wryly, "I see that your clit is stiff, little slut. Did
the whore suck it off for you last night?" "Oh yes, my Lord!" Trudy replied,
"The hot bitch sucked it until I squealed my pleasure, then he fed me a load of
delicious cock cream, to complete my ecstasy!"
"Good, good!" The King rejoined, "After all that is what he is here for, isn't
it." He commented while coming down from his throne. The King's eyes gleamed
with sexual excitement while he announced his pleasure for the morning. My own
blood boiled with pleasure while he informed us of his wishes. "I'm going to
fuck your hot little cunt, Trudy bitch. And the whore can suck off your sexy
clit while I'm reaming you out. At the same time, I intend to suck the harlot's
cock until he feeds me a load of that cock juice that you seem to love so much.
You may assist me by sucking the whore's man cunt for his added pleasure.
The King dragged his feminised bitch around and drove the full length of his
fabulous erection into his hot little arse pit with one full plunge, causing the
bitch to squeal with a mixture of pain, and delight. I had already laid on the
floor beneath the kneeling bitch in eager anticipation, my face poised
immediately below his crotch. I watched in eager fascination while The King's
huge penis had stretched open the transsexual's tight arse ring, and marveled at
his capacity when the entire length of the massive black penis disappeared into
the hole. I raised my face, and my hot mouth engulfed the tiny erect prick, and
began to suck on it with all the passion I could muster.
My body jumped with pleasure when a soft tongue lapped wetly at my arse ring,
then speared it with casual efficiency. Pleasure flowed through me to the
sensual feel of hot, wriggling tongue in my tight arse pit. Then a fresh surge
of delight flowed though me when my hot, throbbing cock was swallowed into the
King's warm mouth, and he sucked on it like a man possessed. We went at each
other with such passionate ardor that it took almost no time at all before we
were all wallowing in ecstatic sexual climax.
The King's flexing testicles flooded his bitch's writhing arse chute with an
ocean of ball cream. The transsexual's tiny penis surrendered its small flow of
sweet sap to my flicking tongue, and my own pulsating cock poured its flood of
creamy juices into the eager mouth of the King. When it was over the King
dismissed us, and we were off for the day's service.
My days at the prison roughly followed the same pattern for the rest of the
week. Each new day began with a session with the King. I then spent hour after
hour, under the close supervision of the transsexual, Trudy, servicing prisoners
sexually in the theatre. And each night was spent in Trudy's bed where I fucked
and sucked him for his pleasure while he eagerly reciprocated.
On the last day I spent all my time being fucked by a succession of prisoners,
while my mouth brought off all the femme bitches. Trudy, of course, acceded to
my plea that I be arse whipped once each day, now realising that this punishment
only added to my pleasure, and by this time the lovely creature was hopelessly
in love with me, and would deny me no pleasure if I begged sweetly.
It was with extreme sadness that Trudy knelt before me on the dock, and sucked
me off one final time before locking my sex up. He kissed me softly, with tears
trickling down his cheeks, and whimpered his sorrow at my leaving. I tried to
cheer the lovely little femme up by reminding him that I would be returning in a
month, and this did cheer him up a little, and he left me after one final kiss,
to await the arrival of the yacht that would return me to the chateau. I must
admit that I was looking forward to returning to a regime of pain and
punishment, and to once again seeing female flesh instead of exclusively male
bodies.
