Chapter 2
The next morning training began in earnest. Pete/Alice ate breakfast by sucking
a thick liquid out of a dildo mounted on the wall and after breakfast his
insides were cleaned out by five very painful enemas. Then his corset was
tightened to make up for the slack coming from his body adjusting to the corset
and Pete/Alice received his daily hormone shots. The training started with
walking again and any transgression was punished severely. Mistress Angela
oversaw the training, looking absolutely stunning again. She wore black, leather
boots, thigh-high and laced up the front, with seven-inch heels. Her perfect ass
was held in a very short and very tight leather mini-skirt and her breasts,
equally perfect, were held in a black, leather bustier. Her long, blonde hair
was gathered in a ponytail and on her hands were short, black leather gloves.
Even now, as she ordered him around and punished every little mistake,
Pete/Alice couldn't help but think that she was the sexiest being he had ever
seen.
After several hours of training Mistress Angela commanded him to stop. His bonds
were the same as the day before and his shoulders felt like they were ready to
pop, his feet were killing him and the ball-gag made him drool. He vehemently
hoped this meant that she was giving him a break. But of course there was no
such luck. She stood very close to him and as he stood completely still, holding
the slave posture he had been taught, she gently grabbed his member. It was
still sore from all the abuse it had been subjected to the day before and
Pete/Alice drew a sharp breath in anticipation of the pain to come, but to his
surprise none came. Instead she gently began to stroke it and it quickly became
erect. As he stood there enjoying the sensation, his hips involuntarily making
small thrusting movements, his breath becoming shorter, his eyes became glazed
over with lust Mistress Angela asked in a low, husky voice: "You like that don't
you, you filthy slave-bitch? You would just love to cum, wouldn't you, you
disgusting sissy-slut?" Pete/Alice nodded and tried to say, "yes" as the
stroking picked up in intensity and he approached orgasm. Just as he was about
to cum, his head thrown back in ecstasy, she shouted into his face: "Sluts like
you are not allowed to cum without permission!" and squeezed his balls
viciously. The pleasure was immediately replaced by intense pain and he doubled
over in pain, too much pain to even scream. He would have fallen over had she
not gripped him tightly, one hand holding him by the neck and the other still
squeezing his balls tightly. She repeated into his ear: "You will not cum
without my permission - if ever." Then she allowed him to drop to the floor.
While he lay on the floor, curled up in pain, she went to fetch something. When
she came back she ordered his to stretch out and lie on his back. Pete/Alice had
no interest in being subjected to more pain and instantly complied, in spite of
the pain. Mistress Angela spread his legs and knelt down between them. In her
hand she held what looked like a pouch made from a fine metal mesh. She grabbed
his now limp cock and his tender balls and stuffed them inside the pouch. It was
a very tight fit and more than a little painful. The pouch had a drawstring
around the opening and she now pulled it so that it sat tightly around the base
of his scrotum. The effect was to reduce his genitals to very small ball in his
crotch, the flesh pressing painfully against the mesh. The drawstring was
secured in a special eye on the rim of the pouch and locked in place with a
small padlock. There was no way Pete/Alice would get out of it without the key.
Mistress Angela explained: "This is a very useful device and you should be happy
that I choose such a fine thing for a worthless slut like you Alice. It insures
that you don't have unauthorized orgasms, thereby improving your behavior. It
can stay on almost indefinitely since your pathetic, filthy and useless little
thing can be washed and dried through the mesh. At the same time it offers up
your balls nicely for punishment." To underline her words she stood up and
kicked the ball hard with the pointed toe of her high-heeled boot. After a
second to catch his breath Pete/Alice screamed in pain behind the gag. As he lay
there screaming Mistress Angela used her sharp heel to step hard on his tightly
compressed genitals, further increasing his pain.
The torture had clearly excited her and she dropped to her knees, straddling his
face as she removed his gag and ordered him to eat pussy. After she had cum a
couple of times, she stood up and used his leash to drag him to his feet.
Instead of re-gagging him she led him to a door at one end of the dungeon.
Pete/Alice, his mouth free for the first time in a day, tried to plead with her:
"Angela, please let me go. I promise I'll never bother you again. And I'll pay
you. Please." His words were cut short as Mistress Angela yanked his leash. She
didn't even shout at him before she launched into a furious whipping. When it
was finally over Pete/Alice lay on the floor covered in red welts, emitting
small, breathless screams. He decided to never speak again unless ordered to.
Mistress Angela allowed him to recover on the floor for some time before she
dragged him to his feet and led him through the door.
Inside were two men waiting on a couch in a small, ordinary looking room. As
Mistress Angela and Pete/Alice entered they stopped their conversation and
turned their attention to Mistress Angela and her slave. "I'm terribly sorry to
have kept you waiting gentlemen, but you know how it is with new slaves. They
have to be reminded of their position constantly." One of the men, a tall
muscular guy with curly brown hair and a moustache, smiled and said: "Yes indeed
Angela. I presume that we are allowed to remind her of her position as well?"
Mistress Angela beamed a brilliant smile at the man and said: "Not only are you
allowed to Richard, you are encouraged to do so. You gentlemen are an important
part of her training."
Mistress Angela and the men engaged in a bit of small talk while Pete/Alice
stood silently by. The other man was also tall and muscular, but with light
blonde hair and piercing, blue eyes. He wore the same outfit as Richard; that is
leather boots, leather pants and leather jacket with nothing underneath, all of
it black. After a few minutes of chitchat Mistress Angela left Pete/Alice in the
hands of the two men and sat down in the couch to watch. After a few minutes
Mistress Janice joined her and they say gently fondling and kissing each other
while the men took care of Pete/Alice.
The man called Richard looked at Pete/Alice and said: "Well Alice, you little
slut, I'm Master Richard and this is Master Anthony. We are here to teach you
how worship a cock properly. We will tolerate no disobedience and no hesitation.
Let's get started." Both men now dropped their jackets and stood with bare upper
bodies in front of Pete/Alice. They removed his armbinder and he now stood with
his arms free for the first time in over 24 hours, but he didn't try to resist.
There were too many against him, they were too strong and he was still wearing
the mittens rendering his hands useless. Master Richard commanded him to kneel
and Pete/Alice complied. He now looked directly into Master Richard's crotch as
he undid his fly and took out his massive member. Pete/Alice knew what was going
to happen and it filled him with revulsion, but he knew that he could not
refuse. When the cock hung out Master Richard instructed him in how to lick and
suck it. Pete/Alice hesitated here and this was instantly punished by Master
Anthony as he caned Pete/Alice's bare ass. He quickly began performing his
duties and with a bit more encouragement from Master Anthony's cane he even did
so eagerly, if rather ineptly. Soon he was sucking Master Richard's huge, rock-
hard cock, looking Master Richard in the eyes as he had been instructed, never
looking away. He felt Master Richard's orgasm build and prepared himself to
swallow the cum, knowing that he mustn't spill a single drop. This proved beyond
his capabilities as Master Richard's cock sprayed its huge load into his mouth,
and a thin stream of cum ran down his chin. After swallowing Pete/Alice had to
fight off the urge to vomit. This combined with him spilling cum definitely did
not go down well with two masters, who started hurling abuse at him as they
punished him, Master Anthony caning him while Master Richard whipped him with a
leather strap. Soon he was reduced to a sobbing wreck and promised to do better
next time. He was given the opportunity to prove this as Master Anthony stood
before him and commanded him to suck his cock. His dick was at least as big as
Master Anthony's and soon Pete/Alice was sucking this too. When Master Anthony
came he was more prepared for what was about to come and almost succeeded in
swallowing all the cum spewing into his mouth. Of course his repeated failure to
perform his duties properly resulted in yet another round of whipping. By now
his body was covered in welts and there wasn't a singe spot on his body that
didn't hurt. It was especially painful when the cane struck his balled up
genitals.
When they had finished punishing him, Pete/Alice lay in a crumpled head crying,
but of course this didn't stop them from continuing the training. Master Anthony
addressed the slave: "Now its time for the one thing I know a virgin like you
have been waiting for your whole life. Its time to pop that cherry." Pete/Alice
began to scream and beg. Getting fucked up the ass was the worst thing he could
imagine and he actually tried to escape in panic. All he accomplished was to get
smacked around some more before Master Anthony twisted his arm and forced into a
kneeling position, his ass pointing up. Master Anthony knelt down so that he
held Pete/Alice's head between his knees, while Master Richard knelt between
Pete/Alice's legs, spreading them wide as he undid his pants. Pete/Alice cried
and begged but there was no stopping Master Richard who applied a generous
amount of some greasy substance to Pete/Alice's ass. "Don't you dare fight me
now, bitch," Master Richard said, "Fighting will only make it more painful."
With that he pressed his rock-hard cock against Pete/Alice's tightly clenched
asshole. He screamed in pain but could not stop Master Richard's thrusting and
soon Master Richard's cock was pumping in and out of his ass while he cried. It
took forever for Master Richard to cum, filling Pete/Alice's ass with hot jism.
He was inconsolable as Master Richard withdrew but he didn't have time to cry.
Master Richard shoved his cock in Pete/Alice's face and ordered him to clean it.
Pete/Alice was broken by now and could not refuse. He licked Master Richard's
cock, coated in a mixture of shit and jism, clean as he felt Master Anthony
position himself between his legs. As small scream escaped him as Master
Anthony's cock entered his sore ass, but he didn't have time or opportunity to
scream or cry as Master Richard now ordered him to suck his cock.
Watching Pete/Alice being fucked in both holes had made Mistress Angela and
Mistress Janice horny and sounds of furious lovemaking could now be heard coming
from the couch. The pain and humiliation was devastating as Pete/Alice stood on
hands and knees sucking a man's cock while being fucked up the ass by another at
the same time his wife made love to another woman. Something snapped in
Pete/Alice's mind, pushing him a good deal further towards accepting his status
as a slave. This would not be happening unless he somehow deserved it.
When Master Anthony had cum, he switched places with Master Richard so that
Master Richard now fucked his ass again while Master Anthony had his cock licked
clean and received a blowjob. Both masters had by now had more than one orgasm
so this time they fucked Pete/Alice for what seemed like ages, their huge, hard
cocks pounding both his holes.
When they finally came and he had swallowed Master Anthony's jism, Pete/Alice
collapsed on the floor completely spent from the pain and humiliation. As he lay
there, he could feel the cum running out of his abused ass, adding further to
his humiliation. He heard footsteps and saw Mistress Angela's high-heeled boots
in front of his face. Her voice came down from above his head: "Get your lazy
slave ass off the floor and stand up," she commanded. Pete/Alice was almost
broken and the last thing he wanted was to give Mistress Angela an excuse to
punish him again, so he obediently stood up. Wasting no time, she tied his arms
with the armbinder and reapplied the ball-gag. Then she led him out of the room,
thanking Master Richard and Master Anthony for their help on the way out. She
led him back to the dungeon and another session in proper walking and posture
training. He tried hard to obey, but the pain from his abused ass made him
waddle strangely and Mistress Angela had to whip him into shape before he was
able to perform somewhat satisfactorily. After training for hours she led him to
his feeding dildo in the wall and while he ate she gave him another round of
hormone shots. Finally she locked him in the cage and left him to rest. This had
been the worst day of his life, even worse than the day before. He hated sucking
cock and he hated being fucked up the ass, but he found himself becoming ever
more the slave, unable to do anything but obey. He even found himself responding
to the name Alice. He cried himself to sleep.
The next day proved to be an exact repetition of the day before, with a few
exceptions. As he woke up he felt an unusual tightness in the skin across his
chest and when he looked down he saw the unmistakable first signs of a pair of
tiny tits. He almost panicked at this and Mistress Angela had to whip him
soundly to focus him on his new training.
His balled up genitals provided him with yet another humiliating surprise. After
his morning feeding from the dildo and the series of horrible enemas, he had to
pee quite urgently and from behind his gag he tried to make Mistress Angela
understand this. Upon hearing his helpless gurgling and seeing him make
desperate facial expressions, Mistress Angela feigned a complete lack of
comprehension: "What is it you useless sissy-slut? Speak up!" She kept this up
until he finally gave up and pissed on himself. Because of the compression of
his genitals, urinating was very hard and when he finally managed to squeeze it
out, the urine sprayed in all directions. Mistress Angela laughed a great deal
at this before punishing him for pissing on the floor. "Looks like you will have
to pee sitting down, just like bitch should do," she said. She washed his legs
and rubbed his skin with the cream, which made his skin softer, before
administering his hormone shots. Then training began. First walking and posture,
then cock sucking and ass fucking before finishing with some more walking and
posture training. He was locked in his cage after eating and promptly fell
asleep.
For four weeks this was the routine: eating and morning enemas followed by
hormone shots. Then training: walking, posture and sex training with minor
variations, before being locked in his cage after eating.
The amount of food he was given had been greatly increased. He was now force-fed
every evening, swallowing a great deal of the fatty, semen-like substance. The
reason for this was soon apparent as he began to grow not only tits, but also
developed the beginnings of a nicely rounded ass. The training was intense and
although he didn't feel feminine yet, he had to fight not to think of himself as
Alice instead of Pete.
Every three days his clothes were changed and he was washed all over, before
being redressed and re-tied. As he was washed his cock was released as well.
While he hung by his wrists from the ceiling, Mistress Angela would play with it
for a long time, bringing him close to cuming before pulling away, always
holding him on the edge. After playing with him in this way, his genitals were
balled up inside the metal-mesh pouch and locked away. The teasing combined with
the effects of the hormones made sure that after the fourth day he was in a
state of perpetual sexual excitement, always horny, never getting any release.
His corset gradually reduced his waist to sixteen inches and his high-heels had
increased in height to six-inches. Walking in an ultra-sexy manner soon became
second nature.
Mistress Angela broke his final bit of free will with a cruel trick. While in
the process dressing Pete/Alice she would leave him almost untied, faking being
called away on some imaginary emergency. The first time it happened Pete/Alice
stood dressed only in his corset and a pair of six-inch high-heeled ankle boots
locked on his feet. Mistress Angela had left him and he could clearly see the
open door to the dungeon. At first he stood still looking at the door,
contemplating if it was a trick. Then he decided that is was worth the risk and
ran for the door. By now he was quite proficient at walking in high-heeled shoes
and he didn't even think about taking then off as he ran for the door, something
Mistress Angela pointed out with great delight after he had been caught. He made
it all the way up the stairs and out the front door before he was stopped.
Outside Mistress Angela was waiting together with Master Gonzales and Mistress
Janice. Seeing that he was defeated he tried to plead and beg, but nothing
helped and he was dragged down into the dungeon to be punished. Mistress Angela
made a point of punishing escape attempts more severely than other
transgressions, so Pete/Alice was soon tied to an upright, padded cross or more
appropriately and an X. Mistress Angela concentrated on his most sensitive
areas: his testicles and his small, new breasts. First she whipped his tits with
a thin, leather strap. Then she inserted a bunch of sharp, thin needles in them
making Pete/Alice cry and beg, much to Mistress Angela's amusement. After seeing
to his tits, she went on to concentrate on his balls. By now Pete/Alice had been
fearing this moment for hours and his crying and begging reached a new high. But
Mistress Angela only laughed: "You worthless sissy-scum! This is a lesson you
had better learn, Alice. You are a slave and slaves obey, no matter what the
consequences are. If I order you to jump in front of a buss, you will do so
gladly, because there is some small hope that it will actually please your
Mistress. Now you will take your medicine and learn to obey every time!" With
that Mistress Angela picked up a pair of alligator clips with wires attached.
The clips were quite large, so large in fact that she could fit one of
Pete/Alice's testicles in each clip. Just having the clips bite down on his
balls made him thrash and gasp with pain, but the real pain came when Mistress
Angela applied electrical current to the wires. The pain was unbelievable and
after screaming his head off for almost a minute he passed out. Mistress Angela
then stopped the torture, woke Pete/Alice up using smelling salts before
continuing the torture. This went on for some time, reducing Pete/Alice to a
twitching crying wreck before Mistress Angela released him from the cross. By
now he knew what was expected of him and he dropped to his knees thanking
Mistress Angela profusely for the lesson, promising to be a better slave from
now on.
Although the punishment had exhausted him completely, Mistress Angela insisted
that he complete the days training program. Disobedience should never be an
excuse for slacking off, not even after a severe punishment program.
Three more times Mistress Angela allowed Pete/Alice to escape only to catch him
and punish him. By the fourth time he was broken and had no fight left in him,
no will to try and escape. Instead he walked up the stairs, closed the door,
walked back in the dungeon and took up position waiting for Mistress Angela. He
knelt down, head bowed down and his hands offering up a riding crop for Mistress
Angela to punish him. He waited so long that his arms were trembling when
Mistress Angela returned: "Better Alice," she said, "I think this calls for a
small reward of sorts." This made him tremble with a mixture of fear and
anticipation. He feared the pain, which was bound to come, but he also hoped
that the reward would be an orgasm.
His orgasms were few and far between and he was given them in a manner that
disgusted him. He was constantly horny and Mistress Angela teased him
constantly, but she only allowed him to cum while he was being fucked by Master
Richard and Master Anthony. Every three or four days, when he thought that he
would go out of his mind from unfulfilled lust, his imprisoned member would be
released while he had a cock buried in his ass and he was giving head. Only when
he was being fucked at both ends would Mistress Angela allow the master fucking
him up the ass to give him a hand job. Pete/Alice still disliked having sex with
men intensely, but he was gradually beginning to look forward to being fucked
because it was the only time he was allowed to cum. He would cum screaming and
thrashing while his mouth and ass were packed. He was gradually reaching the
point were the prospect of having sex with another man turned him on and he
hated it as well as loved it.
But now there was the slim hope that he might actually have an orgasm not given
to him by a huge master pumping his cock in and out of his ass, but by a
beautiful, if very cruel, woman. It turned out that both his hopes and his fears
were true. After handing over the riding crop he was ordered to kneel in front
of a low, wooden table. The table was just high enough for his cock to rest on
its surface. He now knelt in front of the table wearing only ankle-high boots
with seven-inch heels and a corset, which constricted his waist to fifteen
inches, his hands clasped behind his head. His cock strained against its prison
in anticipation of a reward. Mistress Angela, who wore a black, leather bra,
crotchless leather panties and black, leather Oxfords with seven-inch metal
heels, started by planting one heel on his balled-up genitals and stepping hard.
The pain made Pete/Alice gasp with pain, but it didn't go on for long.
Accompanied by his ragged breathing she freed his cock, which instantly sprang
to life, in spite of the abuse it had been subjected to. "I think I'll grant you
an orgasm slave," Mistress Angela said, whereupon she brought the riding crop
down on the head of his cock. The blow was neither very hard nor very soft and
the net effect was to increase his excitement, while causing him pain at the
same time. Then she stepped on his cock, rolling it roughly against the surface
of the table. Again the effect was both painful and pleasurable. She alternated
the two for a log time, several times stopping her manipulations just before he
came. When he finally did cum, his cock was red and bruised and he screamed as
he came, shooting his load as her foot stepped down on the head of is cock. The
orgasm had to be one of the best, if most painful, he had ever had and he
thankfully complied when he was ordered to lick up the cum and clean the sole of
her shoe before commencing training.
Towards the middle of the fourth week of training Mistress Angela had
effectively made him her property, an obedient and docile sissy-slave. The Pete-
persona was rapidly fading, the slave-girl Alice replacing him. Her figure had
become very feminine indeed, with a nice round ass and a pair of perky, if very
small tits. The last week of training had been conducted without bonds on her
hands and had included such things as feminine mannerisms and application of
makeup.
So there was no hesitation when Mistress Angela arrived one day in the dungeon
with two lawyers to have Alice sign away Pete's fortune and sign the divorce
papers. Both lawyers were men in their thirties wearing obviously expensive
suits. The only mishap in the proceeding was when Alice had to be reminded that
she had to sign Pete's name on the papers. As thanks for their efforts Alice
gave each of the lawyers a blowjob, crying a little as she dutifully looked them
in the eye while sucking their cocks. She cried because she realized that this
meant that the last, weak hope she had had of escape was now gone. She was now
irrevocably Alice, the sissy-slut. Only her imprisoned member, her squeaky male
voice and a few of her facial features now remained of the man she had once
been.
Mistress Angela soon set about correcting this too.
