Little Miss Sissy Whore
by A. Boychick, July, 1995
A man "on the make" has his tables turned, permanently, by a
dominating female. There are potent elements of f***ed feminization
(including cross-dressing, exhibitionism and humiliation), strong
discipline, harsh bondage, severe punishments, coerced male-to-male
contacts, non-consensual watersport activities, and the f***ed
wearing of a special chastity belt.
Chapter 1 -- The Pick-up -- His fascination with her handcuffs
leads to his introduction into a regime of strict bondage and
Chapter 2 -- Intensified Training -- Certain parts of his anatomy
are taught new respect, and he is made to suffer intense
Chapter 3 -- Metamorphosis -- He is inexorably turned into a sissy
whore, through harsh training, in his new specially-chosen wardrobe.
Chapter 4 -- Out on the Town -- He comes out into the public and
his new skills are tested in a "rough trade" bar.
Chapter 5 -- Now and Forever -- Events following the establishment
of his new role in life.
Please do NOT email me, asking me to send missed postings by return
email. I WILL REPOST chapters missed to this newsgroup, but can
only do it in small parts (chapters) due to the limitations of the
Of course, I would appreciate positive comments and suggestions,
but not flames, which will be ignored.
* * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *
Chapter 1 -- The Pick-up
Every year I waited eagerly for the three days when PC-Expo
was back in town. In the past, I was always able to find
some willing and naive out-of-town female to pick up, "do the
nasty," and say my hasty good-bys. Most of them were from some
small hick town and were entranced with the Big Apple. In
fact, that was both the nickname for the city, and for me.
Most women just couldn't wait to sink their teeth into me.
So there I was, looking for some love, on the last day of
the three-day convention. I walked up and down the aisles,
past many displays, until I spotted my newest target -- my
conquest to be. I stood back for a while and carefully watched
I couldn't keep my eyes off her as she smiled sweetly and
greeted her visitors. She stood about five and a half feet
tall, had flowing black hair, and a great body. What I loved
most were her lips, which I could imagine encircling my cock
and then slowly and wonderfully slurping up and down on it.
She was wearing an almost see-through white no-sleeve blouse
and a short white skirt. When she turned around and bent over
to find some literature -- I made sure to position myself so
that I could watch -- I licked my lips when I noticed a bit of
visible panty line. This is going to be great, I thought. I
didn't want to appear as though I was loitering, so I found
every excuse I could to walk up and down the aisles past her
company's display before I would make my move on her.
I swaggered over to her and began asking some innocuous
questions about memory management and the speed of data
transfer for her company's products. I didn't bother to listen
to her answers as I glanced down at her neckline. I made some
small talk about the hot and humid weather we were having, and
then I asked her to join me for some coffee at the end of her
day. I tried to sound understanding as I facetiously mentioned
that it must have been just "wonderful" for her to have had to
stand on her high heels all day, and I joked that what she
really needed was a foot massage. Her eyes lit up when I said
this and she agreed to join me for coffee, and the way she
answered me made me assume that there was more than coffee in
store for the evening. She told me not to wait there for her
since she didn't want her coworkers to know about our "date,"
but, rather, to wait outside at the main entrance to the
About 30 minutes after the end of the show, I was still
standing impatiently outside and I hoped I that I wasn't being
stood up, since all my time and efforts would have been
wasted. I never liked waiting for anything -- especially while
buses, taxis and truck rumbled past, spewing out their noxious
fumes -- and I was getting angrier by the minute. Then, I
spotted her, finally, coming out, and I greeted her rudely,
and stupidly, it turned out, saying, "It's about time you
showed up." She looked surprised, as though I had slapped her,
and quickly apologized to me. However, her bouncy smile turned
to one of caginess and wariness.
"Why don't you hail a cab. I want to go back to my hotel
to clean up first," she told me. Now this sounded much more
promising. I stepped out into the street, raised up my hand,
and within 15 seconds, a cab stopped next to us. "Penn Hotel,
please," she told the driver.
She was sullen and silent for several blocks, and then
whispered to me that she wanted to pay me back for having to
wait. I again got my hopes up as the cab stopped in front of
We rode up in the elevator to the fifteenth floor, got
off and walked to the end of the hall. Finally, we were alone
in her room, which was more like a suite, since there seemed
to be a separated sitting room. "Why don't you make yourself
comfortable," she said as she led me over to the couch. As she
sat down next to me her skirt hiked up almost to her crotch.
As she turned towards me, I quickly got a glimpse of the top
of her breasts and her silky white bra through the top two
open buttons of her blouse. Out of the corner of my eye, I
caught her glance at me. I knew that she caught me looking and
she smiled seductively.
As we sat together, I couldn't help noticing what looked
like strange-looking handcuffs on the coffee table. They
looked like large figure-eights. There were rubber gaskets
attached to the steel; the rubber would serve to encircle
one's wrists. I was curious but fascinated about why she would
have left them out like that. It excited me to wonder if this
chick was into kink. She watched my eyes focus on them and, as
if she were reading my mind, told me that she always brought
them with her when she traveled in case she couldn't at first
trust someone she met. She explained that they were specially
made in Europe for prolonged wearing and were very tight-fitting,
yet comfortable. "Here, let me try them on you," she said
enticingly as she picked them up.
I was hesitant. I didn't even know her name. She turned
to me and began kissing me. She ran her hand softly over my
chest and then, slowly down towards my crotch. I was starting
to respond. "C'mon, I won't bite." I was getting more turned
She told me to stand up and face her. I felt my penis
becoming more aroused and I hoped that she wouldn't notice.
She quickly flicked her hand down over the bulge in my pants
and, at almost the same instant, snapped the handcuff around
my left wrist. As the ratchet tightened, I felt my wrist being
encased in its pliable, yet inescapable, rubber grip. Holding
the handcuffs with her right hand, she told me to turn around,
again very lightly sweeping her hand over my bulge. She
reached out, grabbed my right arm, and quickly fastened the
other cuff around my wrist. "There. How does that feel?" she
asked with a chuckle.
The rubber was tight against my wrist. It didn't cut into
my wrist, yet I couldn't move my wrists up and down inside the
cuffs, either. "Okay, that's enough," I said with alarm.
"Unlock me NOW!"
Holding onto the cuffs and ignoring me, she continued,
saying, "These cuffs have another feature. I can also lock the
swivel into any position. Let me show you." She stood up and,
using unexpected strength, pushed my elbows closely together.
She quickly reached down, adjusted the handcuff mechanism, and
it clicked into place. My elbows stayed painfully close. I
could hardly move my arms at all. I stood there, with my chest
jutting out and my wrists and arms fastened together, and
despite my sudden fear during all this, I was becoming even
"Stay right where you are," she laughingly said, as she
went into the other room and came back with a duffel bag and
an ominous looking device, a 10-inch long black rod with a red
button on the end. My eyes bulged with fear as she walked
slowly over to me, obviously relishing the moment, put the
duffel bag on the coffee table and placed the prod lightly on
the swelling in my pants, and then pressed the button. The
pain was incredibly intense! It felt like I got kicked in the
balls and I started to topple over.
She caught me as I started to fall down and told me to
stay on my knees, or else she would use it again. With tears
in my eyes, and the pain still in my gut, I asked her why she
was doing this to me. "I don't need a reason why. And you are
to remain silent unless I allow you to speak -- or else I'll
use the cattle prod again on you." Needless to say, I didn't
need a reminder.
Then, she opened up the bag and pulled out what looked
like a very wide dog collar, except that hers had several
rings fastened to it. "This is a posture collar, my dear," she
explained as she fastened it tightly around my neck. "It will
hold your head proudly up and will stop you from turning your
head at all. Then, I heard a click and she said, "There,
that's done. You're not going far with that locked on."
"Now, stand up," she ordered. "Step up on the coffee
I had only a little trouble standing up and then stepping
up onto the coffee table since the pain in my groin was
subsiding. "Turn and face me," she ordered. "And don't make
this difficult for us!"
She unlaced and removed my shoes, and then my socks. She
reached up and unfastened my belt buckle, pulled down my pants
and my white cotton briefs. My cock had started to become
erect again. "You pig," she said disgustedly. "Look at these
stains in your underwear." She stood up with my briefs and
roughly wiped the remains of the day's sk** marks all over my
mouth and face. "You will have to be cleaned out later," she
Then she reached once again into her duffel bag and
brought out two larger single cuffs, several lengths of chain,
and a small whip. "This is a dog whip," she explained. After
I fasten you securely to this table, and do what I want to
you, I am going to teach your penis some respect." With that,
she reached down, locked the cuffs around each ankle, locked
a chain onto each of the cuffs and then ordered me to lie
down, face up, on the coffee table. My arms ached as my weight
bore down on them and she made sure that my legs were spread
wide as she fastened the chains to the legs of the table.
She took out a large pair of scissors and pointed them
right in my face. She brought the sharp point right down to my
eye and then laughed. "Don't worry, I won't blind you just
yet," she said threateningly. Then she proceeded to cut off my
shirt, and pulled it out from under my body. "You won't be
needing this rag again."
She brought out a large black strap and buckled it
tightly around my chest and underneath the table. "I'm glad
the furniture is well made," she laughed. And then, abruptly,
her tone changed and she said, "Now, please thank me for the
punishment that you are about to receive."
I didn't know what to say. So I just repeated her and
said, softly, "Thank you for the punishment that I am about to
receive." She smiled, and answered, "You're welcome. You have
certainly deserved what you're going to get."
With that, she walked around and stepped over my head so
that I could see right up her skirt. "This is what you were
after, wasn't it?" she demanded. "I know what you want. I know
what all of you want. And I will now get what I want."
She pulled her pantyhose down, and then slowly pulled her
panties down. I smelled her musk; she must have been aroused.
She lowered her body down on me so that her pussy was right
over my face. I could hardly breathe. I couldn't move my head
at all because of the posture collar. My face was imprisoned
by her legs and cunt. She ground herself down on my mouth and
nose. "Make sure you keep your mouth open and your tongue out,
or else," she commanded, though I could barely hear her. She
rubbed her cunt up and down and around my face, mouth and
nose. She was rubbing rhythmically for a while and then her
movements became more frantic. I made sure to keep on tonguing
her, and I even nibbled when I could. Suddenly, she spasmed
and I knew she had gotten there. She stopped churning and then
raised her body onto my chest.
"Now, I want to give you something to wash that down
with," she said wickedly. "Make sure you drink down every drop
or your punishment will be even more severe." With that, she
once again moved her body down on my face and clasped her legs
tightly against my ears. She pushed her slit down on my mouth
reached down and closed off my nose with her thumb and
forefinger, and started to pee into my mouth. I gagged and
swallowed. I could hardly breathe. I swallowed as fast as I
could. Finally, it was over. She pushed her body back up so
that she was straddling my chest as I was gasping for breath.
Once again, she smiled maliciously at me.
"That was for my pleasure. Now it is time for your
punishment. I want to now make sure that we won't be
interrupted if you scream and somebody then hears us. And you
will scream. I'll make sure of it."
She reached over for her pink panties, and felt the
crotch part. "Good, they're still wet from today," she said.
She then rubbed the wet part over my nose, and made sure to
stick them into my nostrils. "Now open your mouth wide." I
obeyed and she stuffed her panties into my mouth. She then
picked up her panty hose and wrapped them tightly several
times around my head and mouth, which held the panties deep in
my mouth. She tied a knot in the pantyhose and the gag was
complete. Then, once again, she pinched my nose shut with her
thumb and forefinger and laughingly said, "See...I even own
I couldn't breathe and I started to struggle against my
bonds. She slapped my face with her left hand. I was startled.
And then she slapped me with her right hand. "Your punishment
collar will stop your head from moving and will stop me from
doing any permanent damage...unless I want to. Now make sure
to keep your eyes open. I want to watch you suffer and I want
you to watch me punish you. If you disobey me, I'll stick that
cattle prod right up your ass, and if I do that, I might even
ruin you for life." She smiled malevolently at me, and just as
suddenly, her smile turned back to sweetness.
And then the punishment began in earnest. First she
slapped one side of my face, and then the other. I was made to
watch her hands swing down and strike my face. I was f***ed to
look at her face, which metamorphosized from demonic to
angelic. I was f***ed to watch this satanic angel hitting me.
Again and again. Inexorably. Left, then right, then left, then
right. It wouldn't stop. She couldn't stop, for she looked
transformed. My face was burning. I could feel my cheeks
puffing up. I could feel bl**d in my mouth. And then, a
gyration from her loins and it was, finally, over.
A sigh, an exhalation, and I could hear her whisper to
herself, and maybe to me, "Oooh, that was nice...that was so
nice." She must have orgasmed just from inflicting pain on me!
I was hurting, and hurting badly. My cheeks felt like
they were on fire. My neck was stiff and sore. My arms hurt
dreadfully since they were locked together behind my back and
I was lying face up on top of them. My mouth was filled up
with her used, wet panties and the sides of my mouth were
distended by the pantyhose tied around the back of my neck. My
legs were stretched over the sides of the coffee table and my
maleness was exposed and vulnerable.
She stood up, pivoted off me, and sat down on the couch.
She promptly placed her feet up on my stomach. I became her
footstool. It felt somewhat better to have her weight off my
chest, but I still couldn't move. I could only look up at the
ceiling, since the posture collar made it impossible to turn
my head. I couldn't believe what was happening to me.
After several moments, she started to explain softly, "I
haven't forgotten about punishing your nasty penis." That will
come next. "But I first want to tell you about your helpless
situation. First, no one knows that you are here. If, for some
reason, you were asphyxiated, or were injured, or I no longer
had a need for you, I could leave you right here, dead or
maimed, in this room. No one in this city knows my name, for
I paid cash for this hotel room. Even you don't know my name.
And that would be the end of that."
I did not know how demented this woman was or could be.
All I knew was that I was in some serious trouble.
"I'm going to give you some time to think about that."
She rose to get up, reached once again into the duffel bag,
and pulled out and showed me what appeared to be a large
leather hood. "This is a punishment hood. It will form-fit
tightly around your head, and once I lock it onto you
punishment collar, it will be much harder to hear anything. To
keep you breathing, there are nose holes, and if I want to, I
can simply close them up. Just make sure you don't make me do
that," she ended up warning me.
With that, she pulled the leather mask over my head,
tightly zipped it and then locked it to the rings on my
collar. I couldn't see anything. I could barely breathe. She
positioned the nose holes carefully over my nostrils and I was
finally able to take in some air. She waited several seconds,
and the she said, "Let me show you the power I have over you."
Suddenly, I couldn't breathe! I felt myself starting to pass
out in the darkness of the hood, and then, mercifully, she let
me take in some air. "You see, all it takes is two fingers,"
Abruptly, she said, "I have to to clean up. And then I've
got to get you ready for more of what's in store for you. I'll
be back with you soon. You stay right there."
Chapter 2 -- Intensified Training
My mouth was gagged. My cheeks, beaten and puffy, were
hurting even more, encased by the leather hood. I could barely
breathe through my nose; I could not avoid smelling the
remnants of her piss and her love juices. I was tied tightly,
face up, on a coffee table in an anonymous hotel room. My legs
were anchored to the legs of the table and stretched apart. My
arms were locked by those devilish cuffs behind my back. I was
totally in her power. And she had gone away. She could have
gone anywhere. Or she could have been sitting right there
watching me. There was no way for me to know.
My wait seemed interminable until I once again heard her
rummaging through her bag. I felt her pulling up on my dick,
and then I felt something pushing against my ass. "I love to
make a man suffer for what gives him the greatest joy," I
heard her say, muffled through my hood. "I'm going to push
this large vibrator way up your ass and turn it on. Then I am
going to stimulate you. Every time you get hard, I am going to
whip your hard penis until it gets soft." And with that, I
felt her starting to slowly push the vibrator into my ass. I
tried to tighten my sphincter, but I could not stop her, for,
after her incessant efforts, it went deeply into my ass. And
then, I felt it start to vibrate.
I felt her sit down on my chest. She must have still been
naked. She had grasped my manhood and waited. Without even
wanting to, I felt myself becoming erect. She wrapped her
thumb and middle finger around the base of my dick, and
reached down and turned off the vibrator. Then I felt a
searing pain. She was slowly whipping my penis! My eyes
started to tear, and I couldn't help screaming, but the scream
turned into a moan inside the gag. The burning pain continued,
for she was relentless. Finally, thankfully, I felt the
hardness in my penis subside.
I heard her say, "I know you men love being hard. But I'm
going to change your mind. Now, let's do this again," as I
once again felt the vibrator begin to buzz. She started to
move her hand up and down on my prick. I think she even used
some lubrication. Her hand went up and down over the burning
welts. Up and down. And my maleness once again hardened. Oh
no...oh no. I couldn't stop it. I felt her weight shift again,
and the buzzing stopped. I knew what was in store for me. And
I couldn't avoid it. Again, she wrapped her hand around the
base of my dick and started to slowly whip it. Again, the pain
was intense and brutal. She waited between swings so that I
could feel the impact of each swish of the whip -- and so I
could experience the fear of waiting for the inevitable flash
of pain. I could hear her chuckle to herself as I became
eventually became flaccid.
And this cycle went on. I lost count of how many times.
Sometimes, I could feel the whip strike my balls. Other times,
she left the vibrator on while she whipped me, and then it
took even longer for my erection to subside. She was truly
Finally, it was over. She pulled the vibrator roughly out
of my ass, and I could feel her get off of me. My dick felt
like it had been turned into chopped meat.
I could feel my bindings loosened from my ankles and the
chest strap holding me down was removed. "Stand up!" she
ordered. As I did so, she helped me regain my balance and I
felt her hands moving over my body. My arms were still locked
behind my back and the hood was still in place.
Then, I felt cold metal being wrapped around my waist.
"This is a custom-made chastity belt," I heard her saying. "It
is made with specially hardened stainless steel, and it cannot
very easily be cut -- not very easily at all. It can only be
removed by someone using very high temperature welding
equipment. And you wouldn't want anyone to try that, I'm
sure." She pushed my bleeding dick down between my legs, and
tightly drew the hinged codpiece down over my pubic area.
Straps of steel were pulled up from the end of the codpiece
down between my legs and then up again, and were locked onto
the waist band in back. "There. Now no one will know you once
had a dick. And it will certainly not get hard and erect for
a long time to come."
She then unlocked and unzipped the leather hood, but left
me gagged with her panties filling my mouth. "I want you to
see this," she said excitedly.
"Your new chastity belt has two special features," she
continued, as if with glee. She sounded as if she were
demonstrating a computer part. "It contains a miniature radio
transmitter and receiver, which can serve as a homing device,
and it also has a special training device, similar to what
disobedient dogs wear around their necks. Let me demonstrate
this for you."
With that, she picked up a small device, which was the
size of a telephone pager, and had a small screen and a red
button. "See and feel what happens when I press this button,"
she said as she showed it to me more closely. Immediately, I
felt a dull ache in my groin, which started to grow in
intensity until I was bucking furiously. I almost toppled
over. She smiled at me and then removed her finger from the
button. "It's great how it works. The more I press it, the
more pain you feel. It's such a wonderful device!"
"There is also an additional switch next to the button."
She continued to explain, "If I press that button, flicking
her finger onto it, it will switch a relay in your chastity
belt which will continue to shock you, even if you somehow get
out of range. That means that you'll end up being damaged
beyond repair. Just think about that for a moment...I don't
think you'd want me to demonstrate that for you." I shuddered
She then untied my gag, but left the collar and cuffs on.
"We don't want you going anywhere while we get you cleaned
up," she said, and led me into the bathroom. She pushed me
into the large stall shower, took out a rough sponge, turned
the water on, and rudely sc****d my skin with the soapy sponge
and finally rinsed me off. After she turned off the shower,
she opened a large bottle of Nair, spread it all over my body,
all over my head, under my arms, into the crack of my ass, and
she even got some behind the cod piece, and told me to wait
right there. I stood in the shower for about 15 minutes.
Finally, she came back and rinsed me off. As the water rand
down over me, I saw my hair all over the bottom of the shower.
I had become almost hairless all over!
She smoothed some feminine-smelling oil all over my body.
"This will soothe you." She paid particular attention to
getting some of the oil on my burning dick, and it wasn't easy
for her to do that, since it was encased by its stainless
"Now it's time to clean you up inside, too. You wouldn't
me to forget that, would you?" she asked teasingly. She led me
back to the coffee table, and it was then that I noticed that
it had been previously bolted to the floor. She had been
preparing for this, and I had fallen into her trap! She took
two of the couch cushions and placed it on top of each other
on the table. "Lie down, face down, on top of the cushions,"
she ordered. Without arms to guide me, she had to help me get
down into position.
I was lying face down, with my ass up in the air. My
head, still unmovable, was pointing downwards. Once again, she
locked on my ankle cuffs. With what must have been the
strength of someone truly driven, she pulled the chains
attached the ankle cuffs and pulled my legs far apart. I heard
another click of a lock and I was secured. She attached
another long chain to the front of my collar, drew it down
under the table and locked it to the chains holding my legs
apart. I was once again helpless, fastened down, unable to
She walked over to her closet and took out a cane. "I
carry this with me because sometimes my sprained ankle hurts,"
she explained. "But mainly because it won't raise any
suspicion." She came back, swinging it in the air. Whish,
whish. Back and forth. I was terrified. She positioned herself
standing at my side. She brought the cane slowly done to my
ass, as if to measure her swing. And then, out of the corner
of my eye, I saw her lift up the cane and she brought it
crashing down on my ass. It sounded like a firecracker. I let
out a yelp. "Stay silent or else," she ordered.
Then she walked around to my other side, again measured
her swing, raised the cane high above her head and then
brought it down on my ass with that horrible loud noise. I
struggled to not scream out. "Good, you stayed quiet," she
said. "Now only two more strokes...but a dozen more if you
dare to utter a sound."
She walked around to the first position, slowly raised
the cane and brought it down. I bit my lip to stop from crying
out. Then, she walked around to the second side and struck me
again. "I do love symmetry," she said.
With that, I could hear putting on rubber gloves and
then, opening a tube of lubricant. "We have to examine you
now, don't we? Answer me."
"Yes, you have to examine me," I replied mechanically. I
would hardly want her to repeat her caning of me.
"You must call me Mistress from now on," she commanded.
"Now answer my question the right way."
"Yes, Mistress. You have to examine me," I said.
"Why must I examine you?" she demanded.
This was so humiliating. I thought for an answer that
would satisfy her. "Because I was dirty, Mistress. Because my
shorts were dirty, Mistress."
"And why must I clean you out?" she asked.
Again, I humbly answered. "Because I was dirty, Mistress.
And you want me to be clean."
"Good. You are learning quickly."
She started by pushing one finger into my ass, which had
already been distended by the vibrator. "How many fingers are
inside you?" she asked.
"One finger, Mistress."
"Should I put another finger in, Sissy?" she asked.
I was confused. She called me "Sissy." "Yes, Mistress,"
I quickly replied. Why would she call me Sissy?
She slowly placed her second finger in and started to
move both fingers in and out. Despite the burning feeling in
my manhood, I knew I could not get hard because it was locked
in its stainless steel confinement.
"Sissy, would you like me to place another finger in you
ass? Please remember to use polite words such as, please, very
much, and thank you when you answer me."
"Yes, please use your third finger, Mistress," I replied --
how could I possibly refuse her.
It was harder and more painful when she started to f***e
her third finger into my ass. She was fucking me in my ass and
I was being f***ed to ask her for more. I tried to raise my
legs and open up my ass so that I would be able to take in her
three fingers. "I see that you're enjoying this. Aren't you,
"Yes, very much, Mistress," I said as she continued to
ream me with her fingers.
"Good, Sissy. Would you now like me to use all four
"Yes, please, Mistress...please use four fingers," I said
with respect, although I was shouting inside, to myself, "No,
no! Please stop!"
Her fourth finger joined the others as she continued to
pump them in and out and round and round. "Sissy, please thank
me for using lubrication," she told me, "for next time you
might not be so lucky."
"Thank you very much, Mistress, for using lubrication."
I could hardly imagine how painful it would be without it.
She couldn't -- wouldn't -- be stopped. In and out, again
and again. My ass was becoming raw inside, despite the
lubrication. "Would Sissy like me to use my thumb?" she asked
Oh no! She was going to put her whole fist inside of me.
I couldn't answer her the way she expected. "Crack!" the cane
sang out twice on my ass. "Don't make me have to use on the
cane on Sissy's ass, again," she warned.
Her threat to use the cane even more made me quickly
answer her. "Yes, Mistress. Please use your thumb and your
She pulled her four fingers out, put some extra
lubrication on her gloved hand, and then started pushing her
fist up into my ass. I squirmed. I couldn't take it all in. I
tried to resist but she kept on pressing. Finally, her entire
hand went in! She pushed it further in, then out. "Say you
love being fist fucked, Sissy. Admit it to your mistress."
I was groaning. I couldn't help it. "Yes, Mistress, I
love being fist fucked. Please don't stop."
And she didn't for a long while. Her fist went in and
out. Sometimes she flexed her fingers. Other times she rotated
her fist as it went in and as it was pulled out. "I just love
fist fucking sissies," Mistress explained. "I love to see them
squirm and suffer."
Finally, she pulled her fist out and it was over. "Now
thank me for fist fucking you."
Although I was inwardly thanking her for stopping, I
replied, "Thank you, Mistress. Thank you very much for fist
"Why, Sissy...you're very welcome," Mistress answered.
Mistress sat down on the couch and rested for a while.
She then said, "I am going to have to gag you now. I'm tired
of hearing you."
She brought a rubber gag attached to a belt over to me.
"Say ahh", she joked, and then she pushed it into my mouth.
She stretched the belt around the back of my head and fastened
and locked the belt buckle. "This is an inflatable gag," she
explained. She brought over a small hand pump, attached it to
a nozzle in the rubber, and started pumping. I felt my mouth
expanding. My mouth felt like it was going to split open.
"There, just a little more and Sissy's mouth will be nice and
quiet." "And full," she added.
She let me lie there, to let me experience my
As if she were reading my mind, she then once again squeezed
my nose tight and I couldn't breathe. "You see, I can do
anything I want to you." I couldn't even shake my head to make
her remove her fingers. She drew her fingers away from my
nose, picked up the cane, and gave me six quick whacks on my
ass. All I could do was to moan into my new gag.
"See? Now I don't have to listen to you any more."
"Now, I am going to give you the large enema I promised
you," she explained. "I am going to let just a little bit more
than two quarts of liquid fill you up and I am not going to
let you expel it until I think it's the right time. It will
probably be much longer than you can imagine, though."
In her saleswoman's voice, she continued. "I will be
using what is called a balloon enema tube. It will allow me to
fill up your ass with an expandable bulb. Then, after I fill up
your insides with our nice, warm, soapy liquid, all of it will
be held nicely inside of you. You won't be able to expel any
of it until it's time to let it out."
She pushed the end of the enema tube deeply into my ass
and then slowly inflated the bulb that would keep all the
contents in. She walked into the bathroom and came back with
the bag filled up. "This soapy water will fill up Sissy quite
nicely," she exclaimed. Then she attached the tube from the
bag to the tube in my ass and opened the valve to start the
"I know that will feel nice and silky," she said. "But
after holding it awhile, it won't be so pleasant."
I could feel the warm liquid entering my bowels. I was
being filled up. There was nothing I could do. She reached up
to hold the bag higher, and the inflow of water sped up. I
started to cramp. How was I going to hold it in? How was I
going to bear it?
Finally, she said, "There, it's all in you now." With
that, she removed the tube, tied off the end, and once again
picked up the cane.
"And now, an even dozen more strokes of the can for you,
Sissy, for being dirty and for making me clean you up inside,"
she declared. And this time, as before, she slowly measured
her swings and brought the cane down full f***e on my ass.
Every time she struck me, I could feel the liquid swishing
around inside of me. I was beginning to cramp more horribly,
and I knew that was what she had wanted -- to be doubly
punished and to suffer as much as possible!
After the twelfth crack on my ass, it was over. "I'm
going to go out now, Sissy, because I have to pick up a few
extra things. I'm going to have to lock you back into that
nasty hood, though. And this time, I am also going to control
your hearing." She rolled up several wads of cotton and f***ed
them into my ears. Then, she carried over the black leather
hood and pulled it over my gag and over my head. Once again,
she tightly zipped it up and locked it even more snugly to the
posture collar. "Oh, it fits you so much better now that all
of your hair is gone," she remarked. Thankfully, she
remembered to adjust the nose holes so that I could breathe.
I was totally isolated. I couldn't see. I couldn't hear.
I couldn't move my mouth. But I could certainly feel. I could
feel my cheeks, which were swollen and inflamed. I could feel
the burning from the welts on my ass. I could feel the pain
from the repeated whipping on my steel-encased manhood. I
could feel the soreness inside my ass, and I could feel the
cramps getting stronger. I couldn't let the liquid out! My
insides were in turmoil and I was helpless. How long was she
going to leave me? What if something happened to her and she
didn't come back? I started to moan into my gag. I couldn't
stop moaning in pain. There'd be no end to this!
* * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *
Chapter 3 -- Metamorphosis
It seemed and felt like forever. There I was, locked down
onto a coffee table in an anonymous hotel room by a woman
whose name I didn't even know. My wrists were tightly bound
behind my back by those infernal cuffs that were, at first, so
interesting to look at...my arms held at almost an impossible
angle by those same custom-made cuffs...wearing a posture
collar which made me unable to move or turn my head...f***ed
to hold inside more than two quarts of enema by a huge
inflated thing in my ass, my insides bloated and
cramping...moaning desperately into an inflatable rubber gag,
my mouth bulging, overfilled...wearing a leather hood pulled
over my hairless head...unable to see or hear...suffering from
numerous huge welts on my ass, made by that horrible
cane...and wearing that unforgiving steel chastity belt, which
f***ed my maleness down and back between my legs.
Will she ever come back, I wondered. And what would she
do to me next?
Finally, after what seemed like hours -- who could tell? --
I felt movement in the room. I could sense, rather than
hear her, or whomever it was, approaching my bruised, abused
I could feel the flaps being opened on each side of my
hood, and then the cotton wads were removed. Thank goodness I
could hear again! "I went out and bought you some things," I
heard her cheerfully say. "Actually, I used up all of the
money in you wallet...I knew you wouldn't mind."
Damn. She robbed me! She took all of my money! I had
almost $300 in cash and she spent it all. I wondered on what.
I couldn't stop from moaning. "Oh, do you hurt inside?"
she asked placatingly. Then, abruptly, I felt her strike my
ass with the cane. "We wouldn't want those nice purple welts
to heal up too quickly, would we?" she said. She took her time
between each stroke and struck me six times in all. Throughout
this, as I was once again made to move involuntarily with each
crashing of the cane on my ass, I could feel the liquid
sloshing inside of me, thus making me cramp and ache even
After several more fear-filled minutes, I could feel her
unlocking the chains holding my collar and ankles down. "It's
time to release your enema, but you're going to have to
promise not to try anything silly, or you'll be even more
severely punished. And do remember that special device on your
chastity belt. Moan twice loudly if you understand me." I
She made me stand up, again, stopped me from falling
over when I wobbled as I stood up, and made me walk into the
bathroom. "Wait just a minute," she ordered. She reached
behind me, unlocked the cuffs and told me to turn around. She
then proceeded to deflate the bulb holding in the enema and
then pushed me down on the toilet seat. Almost immediately,
the liquid started gushing out, and I was gasping for air as
the cramps slackened. The inside of my ass was on fire. Could
she have put something else into that liquid? And then another
gush. Eventually, it was all out. I was emptied out.
"There. That's not so bad, is it?" She stood over me as
she unlocked and unzipped the hood. She pulled it up over my
head. She deflated the gag in my mouth, and unlocked and
unbuckled the belt holding it in. She then unlocked the
posture collar and I flexed my neck and turned my head, hoping
that there wasn't any permanent damage.
"Stay seated right there on the seat. Now, just in case
you have forgotten, let me remind you about our chastity belt
training device." She picked up her device and pushed the
button. Once again, I felt the relentless buildup of pain, and
I couldn't stop from bucking my hips as I sat there on the
bowl. I looked up at her pleadingly, and I started to beg for
her to stop. "Please stop, Mistress," I cried. She slapped me
across the face with her free hand and said, "Another five
seconds of pain for speaking out without permission. Now count
slowly to five."
And out of my mouth from far away, I heard myself saying,
"One mistress...two mistress...three mistress...four
It was over. I instinctively grabbed my crotch, bending
over. If I could have, I would have laid down in a fetal
position. I was totally in her control.
She then allowed me several minutes to "come to" and then
made me stand up, and walk to the stall shower once again.
"Now that your hands are free, you can clean yourself up. Make
sure to wash yourself all over. You must be clean when you
I showered and soaped myself up. The soap had a very
flowery fragrance. I washed all over my body and I very
carefully and soothingly washed between my legs, up and down
my butt crack, and over my ass cheeks. I could see drops of
bl**d washing down with the soapy waste water. I then examined
the chastity belt. It wrapped around me so tightly I couldn't
even get my little finger between it and my skin. I felt
around for the locks and felt that they were recessed and were
simply part of the straps locked around my body. I knew I
could never get this thing off without her permission. What
had she done to me? What WILL she do to me?
I heard her tapping on the glass. "You've had enough
time. Turn off the water, dry yourself off and then come out
here. Move it." I could feel just a slight punctuation of pain
in my groin. She must have pressed that damn button to remind
I got out of the shower, picked up the large towel that
she had left for me, dried myself off, and walked into the
sitting room. I saw that she had removed the cushions from the
coffee table and that she had placed some women's clothing and
frilly underwear out on it.
"First, let's put some nice powder on your sissy body."
She dusted me all over, and I felt the powder soothing those
very raw parts of my ass. Powder got all over the floor and,
once again as if she were reading my mind, she said, "Don't
worry, we won't be back here after tomorrow."
"Second, I want to make you much more aware of your
nipples. That's what you like to look at in a woman. Admit
"Yes, Mistress. I love women's breasts. Very much." I
hadn't forgotten my manners.
Her hand was never far from that fiendish button as she
placed a nipple clamp on my left nipple and started to tighten
the thumb screw. The tightening started to pinch, and then to
hurt even more. "Don't worry, the pain will go away after a
while -- after the nipple is fully pierced by these clamps"
she laughed. When she was done, she started to work on my
right nipple, slowly tightening the thumbscrew until it, too,
was so very tight. I started to squirm. "Stand still!" she
ordered, and I saw her press the button that emphasized her
order with that pain in my crotch.
"This is going to be a very long and painful night,
unless you obey. Promise me that you will be good."
"Yes Mistress, I'll try. I'll do anything you want.
Please make the pain stop."
Holding the button down, she slapped me twice on the
face. "You'd better do better than try."
She picked up what looked like breast-shaped skin colored
rubber falsies and placed one over the left nipple clamp. She
began to screw the falsie onto and down a pre-threaded post
extending outward from the clamp so that it completely covered
the clamp. The falsie had the shape of a real breast. She
screwed it on even more, which started pulling the clamp
inside of the form. As she did, the nipple clamp that so
tightly held my nipple was pulled away from my body and into
the rubber breast. The base of it, which must have been
wrapped around semi-elastic wire, fit snugly against my chest.
"A couple of more turns, and then we'll take care of the other
It was agony. The sharp points on the nipple clamps
started immediately to work their inevitable way through my
nipples, while at the same time, my nipples were being pulled
away from my body. As she finished tightening the second form,
she slapped each of my "breasts." I almost fainted from the
pain. "Now thank me for giving you breasts so that you can be
my special Sissy."
"Oh, oh, Mistress. Thank you so very much for giving me
She then picked up the light pink-colored corset lying on
the table and drew it around me. She made sure it covered my
breast forms, started to lace it up, and said, "This will give
you a nice hourglass figure." She continued to tighten the
laces, yanking and pulling. She made me raise my hands so that
she could tighten the lacing even more. It was getting more
and more difficult to breathe, and, yet, she kept on
constricting me. "There, almost done, and then we'll lock it
on" she said, and then I felt and heard her fasten and close
two locks -- one at the top and one on the bottom.
"It's so nice what a tightly-laced, well-boned corset
will do to a woman's figure," Mistess remarked. She then
picked up a matching pink pair of satiny panties and held them
in front of me. "Take these and put them on now."
I bent over as much as the corset allowed me and slipped
the panties onto my legs. "Go ahead, pull them up -- that's
all you'll be allowed to wear from now on."
I pulled the satin panties up my legs. They fit snugly
over my chastity belt as the waist band snapped against my
skin. Even though my manhood had been whipped and beaten, I
still felt a stirring. But I knew it could never become erect
unless Mistress allowed it.
"That's good. Now step back. I want to take some pictures
of my Sissy."
She picked up a Polaroid camera and aimed it at me. After
several flashes, she put the camera down. "These will be look
great in our picture album."
She then told me to sit down on the couch. She directed
me to apply pink nail polish to my toenails, the same color as
my pale pink panties and corset. It wasn't easy, since the
corset made it hard to bend over and my breathing was already
labored. As my toenails dried, she had me file and then apply
the pink nail polish to my finger nails. "You're going to be
such a beautiful Sissy," Mistress gushed.
She then showed me how to roll up each pink stocking and
pull them up over my toenails, ankles and legs without
snagging -- and then to make sure that they were straight, and
without wrinkles. Finally, I had to stand up and I was taught
how to attach the stockings to the tabs hanging from the
corset. I had to then pose for yet another picture.
"Put on the your skirt," I was directed. It was white
leather and was extremely short. As I pulled it up over my
stocking-covered legs, again I felt the stirrings. I zipped it
closed and she came over and placed a little silver lock
through two eyelets and the zipper. The skirt barely covered
my panties and my ass! The bottom of my crotch was only inches
from the bottom of the skirt. "If you bend over at all...and
you will," Mistress added, "anyone will be able to see your
fine purple welts through your thin pink satiny panties."
She held out what looked like a silky camisole. I pulled
it over my head and it floated down over my shoulders. It had
thin white spaghetti straps and barely covered the top of my
corset. The pink corset stays and laces could be seen through
the thin silky camisole. "Time for another picture," Mistress
said. And I posed.
I was then told to turn around and face away from her.
She picked up the custom-made handcuffs and quickly fastened
them around my wrists. "I won't pull your elbows together this
time...unless you give me some cause," she warned.
I was made to sit down in a chair. She quickly pierced
each ear twice, without using any ice or pain killer. She
dabbed the holes with alcohol and then inserted two pairs of
large gold hoop earrings. I could feel them flapping against
my neck whenever I moved my head. She placed a blond wig on my
head and glued it to my scalp. She then used shaving cream on
me and carefully shaved my face. "We're going to have to do
some electrolysis on you."
She then applied eye liner and eye shadow. and followed
with deep red lipstick. She finished up with some blush and
face powder. "Now stand up," she said, as she took several
"Oh, you can't very well walk around in stockinged feet,"
Mistress warned. "Here, try on these shoes. They ought to fit
She picked up a pair of white high-heeled shoes which had
four-inch long spiked heels. How was I ever going to walk in
these? "Stand up on the coffee table and let me get them on
you," she commanded.
I stepped up on the table and then lifted my right leg.
I thought momentarily of rebelling, and I realized that even
if I could have kicked her, my arms were still locked together
behind me and the chastity belt had its special punishment
device. I knew that I would be severely reprimanded if I had
tried. She slipped the right shoe on my foot, fastened the
strap and locked on another tiny silver lock. I stood up on
that one shoe and almost teetered off the table. She held me
as I regained my balance. She then put the left shoe on my
foot and locked it on. My pink toenails showed through my
stockings at the front of my shoes.
"Now stand straight and turn around." I faced away from
her. "Bend over and touch your toes...quickly, now!" I did the
best I could; with the constriction of corset, I could hardly
reach my knees. "Grab your knees and stay still! Keep your
balance!" My ass was directly in front of her and my pink
panties showed below my skirt. She lifted my skirt back over
my waist and then pulled my panties down to my stocking line.
This was so humiliating.
"I want to examine you. Reach behind you and grab your
ass cheeks and spread them for me." I could hear her snapping
on a rubber glove, and I watched as she slowly applied some
lubrication on her fingers. Then, I felt two or three fingers
enter me -- I didn't know how many -- and she moved them
around and in and out. "Good, you're clean and you're still
wide open. We'll have to make sure you keep it that way."
She picked up a large 6-inch dildo with a knob on one end
and a metal loop on the other. "You will be locking this dildo
inside of your ass every day from now on. It will only come
out when I say it should." She instructed me to put a generous
amount of lubrication on it, and then to reach around and
insert it in my ass. I must have taken too long, for I felt
the now familiar pain in my groin for just a moment. I quickly
pushed in as far as it would go.
"Now feel for two tiny holes on the steel straps that
pass right near your ass." I found each hole. "Take this
special lock," she ordered me, "run the hasp through the hole
on the strap on the right, through the eyelet on your dildo,
and then through the hole in the strap on the left strap." I
fumbled several times to find the holes since it wasn't easy
to do this without seeing what I was doing. I hoped that she
wouldn't repeat her reminder of pain. "Are you done, now?
Close the hasp into the lock."
"Click!" She had made me lock my own 6-inch dildo inside
my ass. "You'll get much better at doing it in the future,"
she noted evenly. The dildo was deep inside of me, but it
couldn't go in any further and it certainly couldn't come out.
"Now stand up, pull up your panties, and turn around and face
Then, she brought over the dog whip that had so severely
bruised my manhood, and warned me not to move. She told me to
spread my legs apart and make sure to keep them that way. "I
want you to look down at you nice new clothes, your pink
stockings and your high-heeled shoes as I punish you." She
lifted up my skirt, and very slowly and deliberately whipped
the inside part of each thigh, on the skin between my panties
and my stockings, causing thin red, oozing, welts to appear.
After twenty wicked slashes -- I had been f***ed to count, and
to duly thank Mistress for each one -- I was allowed, and
helped, to step down off the table.
As she unlocked my cuffs, she announced, "Now it's time
to learn how to walk like a sissy whore." I looked at her in
surprise. She smiled. "That'll be your new name from now on.
And that's the service that you'll be performing for me. And,
from now on, in your speech and in your thoughts, I am, and
will forever be, your Mistress."
She once again picked up the device. "I want you to walk
like the sissy whore that you have become. When you walk, I
want you to place one foot in front of the other and I want
you to swivel your hips, and I want you to make sure you feel
that nicely greased dildo moving around inside your ass. I
want you to feel your thighs rubbing against each other, and
I want you to feel those nasty welts I just gave you. I want
you to stick out your new breasts and be proud of them."
I could barely stand up and felt the familiar tingling
reminder between my legs as I saw her press the button. "Hurry
up and do it," Mistress ordered. Stumbling and staggering, I
started to walk slowly to the end of the room. "Turn slowly
around and walk back towards me. Hold your head proudly and
high or else we'll use something that will."
I remembered wearing the horrible posture collar, and
vowed to myself to please her. I just couldn't stand any more
So I walked back and forth in the room. Away from her,
and then, turning slowly around, back towards her.
Occasionally, when I displeased her, I felt the familiar
tingling, and then pain, in my groin.
After an hour of walking lessons, Mistress had me open
her door to go out into the hallway of the hotel. "Walk all
the way down to the end," she ordered. When I got to the end,
I felt the pain in my groin and started to double over when it
wouldn't go away. I knew that she wanted to show me how far
the radio device could reach, and to realize that there was no
way I could get away. When the pain subsided, I walked back
towards her. Back and forth. How long could this possibly
* * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *
Chapter 4 -- Out on the Town
My feet and legs were sore. I was laced and locked into
an overly tight pink corset, which was holding in, in turn,
rubber breast forms that covered sharp nipple clamps which
were inexorably piercing my nipples. I was being made to walk
in 4-inch stiletto heels...showing my stockinged feet and
painted toenails...to walk like a cheap whore on the make...
up and down a hotel hallway...dressed in the shortest white
leather miniskirt which barely covered my crotch and my pink
panties...and which barely hid the welts of the ruthless
beatings of her harsh cane. I was wearing my new white satiny
camisole top with its spaghetti straps......my new blond
wig...my newly pierced ears with the flapping hoop
earrings...my painted eyes and face and my grotesquely-painted
red-lipsticked mouth! And under it all...under that entire
visage...the huge dildo inside my ass that was locked to that
horrible chastity belt with its electronically activated
The elevator stopped. Out came a well-dressed elderly
couple. They looked at me in wonderment. Mistress quickly
announced, "He's a sissy whore in training."
"Walk, Sissy Whore. Show them your stroll." I began
walking, as ordered, and they watched me for a while and then
laughed. Then, they walked on towards their room.
"You see, no one cares about you. No one knows who you
are...or were." I couldn't believe that in the space of an
evening, she had transformed me into what I had become -- a
fully cross-dressed, totally enslaved, sissy whore.
"It's time to go and earn your keep. Stay out here and
don't move." Mistress went into back into her room. I was left
standing in the hallway. I could try to run, but I knew I
wouldn't get far. I had no money, and no identification. How
could I quickly get away? How could I explain what happened to
me? How would I be able to get out of the chastity belt?
Minutes passed. Doors opened and closed and other hotel
guests passed by me. Some looked at me as if I were a carnival
side show. Two men stopped near me and leered at me. One
whispered, "Cheap whore" to me and reached out and grabbed my
breast. A sharp stab of pain, and I almost fainted! I realized
the nipple clamps were going to be working their way all the
way through. They laughed, and then they walked on.
Embarrassed, I looked quickly down at the floor, but then
remembered Mistress's warning. I quickly held my head up high.
Mistress finally opened the door and came out, holding
her cane. She was dressed all in black. How appropriate, I
thought! She was wearing tight black leather pants, and a
black leather studded vest. She was wearing 2-inch high heeled
black shoes. It was obvious that she wasn't wearing a bra. On
her black studded belt, she had attached her dog whip on one
side and her cattle prod on the other. In the back, she had
placed the handcuffs in a leather pouch. She was wearing her
infernal button device like one would wear a beeper, hooked
onto the edge of the pocket on her pants. She had made herself
up so that the skin on her face was porcelain white, and she
had red lipstick on, just like mine, except that hers looked
ladylike. On top of her head, she jauntily wore a black
motorcycle cap, with her hair flowing out from the back. She
was gorgeous. In other circumstances, I would have wanted to
fuck her right then and there, except for my unfortunate and
"Okay, it's time for some fun," she laughed. We went down
in the elevator and when it stopped on the ground floor, she
grabbed my hand to walk like teen-aged lovers, or, more aptly,
like a mother and c***d, through the lobby. Heads turned and
people stared. "Remember how to walk," she said loudly to me,
loud enough to be heard by all. "Rotate those hips...keep your
sissy whore head up high." I heard murmurings and then
laughter. I saw some people shake their heads in disgust.
Then, we were out the door and into the street. I heard
lewd catcalls as the city's "worst" turned to watch me stroll.
Mistress smiled at them and shook her head up and down
approvingly. I knew she was pleased.
She ordered me to stop and stand right there on the
corner. "Don't dare move." I had to endure more catcalls and
insults. Several teen-aged boys stop to watch. One of them
came over, reached under my miniskirt, and grabbed and
caressed my ass. I couldn't do anything to stop them.
Meanwhile, Mistress walked to the other end of the block,
turned around, and waved at me. She raised her hand and
extended a finger and then I felt the familiar pain in my
groin. I almost bent over double. She then turned, and walked
another block away and did the same thing -- arm up, finger
extended, and then the pain. I then saw a taxicab stop next to
her and she got in. The taxicab disappeared from view.
Meanwhile, I had suffer through more name calling. Other
men came over to stare at me and to feel my body all over. One
of them walked right up to me, and grabbed at my crotch, while
trying to kiss me with a beery, smoky mouth. At that moment,
a taxicab pulled up next to me, and Mistress got out. "That's
enough...get in," Mistress said in a dominating tone. "Sissy
Whore belongs to me." Mistress then took me by the arm and
helped me into the cab. I was terrified and shaking.
"West Street," she said to the driver. I could see him
looking back at me in the rear view mirror, and then
chuckling, almost silently, to himself.
"I just want you to realize, Sissy Whore, that all that
you have in the world, now, is me." I wanted to cry; I was so
afraid. "All you are, you must realize, is a piece of meat
that I own, and can do with whatever I please."
"Now compose yourself," Mistress ordered. "Take some deep
breaths." I sat there in the cab, trying to get hold of
myself. It was difficult to take in more than half breaths
because of the corset.
The cab stopped and let us out. I saw prostitutes -- men
and women -- and men dressed like women -- and some dressed
like me, I horrifyingly realized -- walking up to cars that
had slowed down and stopped. I saw several talking to the
drivers of the cars, obviously negotiating and transacting
business. Others got into the cars, which drove away to do
what they were going to do. We watched for a while, and then
Mistress turned to me and said, "This is where you will end up
if I become displeased with you."
One of transvestites came over to me, and looked me over.
In an effeminate drawl, he/she asked, "Oooh, is this a new
girl out to make some money?" Mistress laughed and replied,
"Not yet...not for a while, anyway."
After a few moments, we walked down the block to a bar.
"It's time to for you to make some money for me," she said. I
had to carefully walk down several stairs to get to the front
door and then through the door into the darkness. My eyes had
to get accustomed to the dimness and then I looked around.
This was one very rough trade bar. All eyes turned to us.
Mistress stood there until she had everyone's attention
and then loudly announced, "My virgin sissy whore will blow
anyone in this place for five dollars." I was mortified. There
was a murmur of reaction. She made me stroll to the back of
the room and had me get down on my knees and turn face the
crowd. "Who's first...step right up." There was a jostling and
one guy, dressed in a black t-shirt, jeans and combat boots,
strutted over to us. All of his buddies were watching.
"Since this is Sissy Whore's first blowjob, this one'll
be free," Mistress again announced. The men started to laugh
"Come on over...don't be shy," she told black shirt.
Mistress positioned him so that his crotch was right in front
of my face. She turned to me and instructed, "Okay, roll down
his zipper and pull out his dick."
I reached towards him, opened his zipper and reached for
his maleness, which was becoming aroused. It was becoming even
more erect in my hand. I pulled it out. "Give the tip of his
dick a nice kiss with your juicy red lips," Mistress directed,
and I did. I had never done this kind of thing before and,
yet, I couldn't stop what she was doing to me.
"Now grab his ass and pull his dick into your mouth. Make
sure to make it really wet as it goes in. Don't you dare gag
when it goes all the way in."
All eyes were on us as I slowly drew his manhood into my
mouth. When it got far in, I couldn't help gagging and
everyone laughed. Mistress laughed, too. She must have let
that infraction pass by because and I was really glad that she
didn't press the button to activate her pain maker.
"Now that you know how far is too far, I want you to give
him the best blowjob of your life," Mistress demanded. "I want
you to keep his dick nice and wet as it goes in and out of
your sissy whore mouth. And, I want you to swallow his cum
when he's done."
I looked up at black shirt and he smiled to me. Everyone
was watching with rapt attention. He grabbed the back of my
head to more quickly control my head and to move it back and
forth. I was f***ed to service him, on my knees in my new
sissy whore ensemble. His dick went in and out. I grabbed his
buttocks to hold on to him. I could feel his gyrations
increase and he finally held my head tightly as he came deeply
in my mouth. I swallowed down the salty, slimy liquid as
quickly as I could. I heard applause and cheers.
"Now lick him clean and again kiss the tip of his dick as
a thank you," Mistress ordered.
Mistress took lipstick out from her pocket and again
painted my lips with the grotesque red color. You'll redo your
own lipstick next time. She then announced, "The next one will
cost five bucks...who's next?"
Another man came over, and handed her a five-dollar bill.
"Introduce yourself to the man," Mistress directed.
"Hello, my name is Sissy Whore, and my Mistress would
like me to give you a blowjob," I said.
I felt the pain in my groin. "YOU want to give him the
blowjob...now say it!" Mistress warned.
It was bad enough being f***ed to do what I was doing,
but I so humiliated, being chastised like that. I complied by
saying, "Yes, I want to give you a blowjob. Let me open your
zipper and kiss the head of your penis."
I went through this exercise countless times during that
night. So many different anonymous dicks...being f***ed to
have them move, wet and slick, in and out of my
mouth...holding on to their asses...having them hold my
head...having them ejaculate deeply in my mouth...and then
having to swallow their cum.
After hours of this, I heard the bartender announce,
"Closing time." It must have been approaching four in the
morning. How long would this go on?
Mistress said, "You did nicely for us. We made almost one
hundred dollars. Now, we'll give you something to wash that
taste out of your mouth."
She made me get up. My knees and legs were sore. My mouth
and jaw were throbbing in pain. She walked me into the men's
bathroom. "Don't you worry...this is a liberal sort of place,"
Mistress reached around to her pouch and took out the
handcuffs. She then made me kneel down on the wet floor in
front of the urinal. She locked my left wrist into the cuff,
pulled my wrist under my legs, inside the fold of my knees,
and then held down my right wrist and attached it to the cuff.
My locked wrists held me in a kneeling position. She then
pushed me back and positioned me so that the back of my neck
was right up against the bottom lip of the urinal. She took a
length of cord out of a pocket, drew it under my chin, and
pulled it up and around the piping above the urinal,
stretching my head up and back. Then she tied it off in a
knot. A feeling of dread was quickly enveloping me. "There'd
better be no complaints," Mistress instructed.
"Please, Mistress. Please don't make me do this," I
"Nonsense. This is all that you're good for," Mistress
said as she sneered at me. "After all, all you are is a
worthless piss-drinking sissy whore."
Then she smiled and said, "Oops, I almost forgot." Out of
her pocket she drew out a metal ring, surrounded by rubber,
which was about two inches in diameter. "Open your mouth
wide!" she commanded. She positioned the ring inside my mouth
so that my teeth fit into grooves in the rubber. She then
inserted what looked like old roller skate keys into each side
of this ring and started to turn the keys. As I heard what
sounded like ratchet clicks, my jaws were f***ed to open even
wider. I was helpless... I couldn't move my head; I couldn't
close my mouth. "Good, that will keep your mouth wide open.
Now don't forget to swallow!"
And then she walked out, leaving me there, unable to
move, on my knees on that dirty, urine stained tile floor.
A few minutes later, a man came in, looked at me and
laughed. He came over to me, opened his zipper, pulled out his
dick and stuck it deep in my mouth. I felt a stream of his
hot, salty piss going down my throat. I could hardly breathe
and I swallowed as fast as I could. When he was done, he
patted the side of my cheek, saying, "Good girl," and left.
After that, there was a steady procession of men into the
bathroom. Some came just to watch and cheer. Some of them
purposely pissed all over my face. Some of it went into my
eyes and stung; other piss went up my nose. A lot of it was
sprayed all over my clothes and down under my corset. My
aching nipples stung from the salty liquid. Even though I was
becoming sick to my stomach, I proudly held my head up high,
as Mistress commanded, and took in all that I could.
Then, abruptly, it was over. Mistress came in, looked at
me and laughingly said, "You smell like piss. and you look
like shit. Your makeup and lipstick are all smeared." And she
slapped me twice on my face to emphasize her point. "C'mon,
it's time to go back." She cut the rope, unlocked my wrists
and helped me get up. But she kept that horrible mouth dilater
fastened inside my mouth. She hailed a cab for us and we went
back to the hotel. The driver almost refused to drive us, but
relented when Mistress promised to double the fare. He had to
open the windows wide because of the reeking odor.
The few people we passed remaining in the hotel at that
early hour all turned around, to look at Mistress and her
sissy whore, and to also find out where the stench was coming
from. I saw many of them turning away in disgust and revulsion
after also seeing me with my mouth kept wide open, like a
Finally, we were in the elevator on the way up to
Mistress's hotel room.
* * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *
Chapter 5 -- Now and Forever
Thankfully, nobody rode up with us in the elevator.
Mistress used her passcard to open the lock and we entered her
room. "I'm so excited about tonight and turning you into my
sissy whore that I can hardly sl**p," she exclaimed.
Mistress walked over and sat down on the couch. She
directed me to take my special cuffs from her, fasten my
wrists behind my back and to then stand before her, with my
mouth agape. "I'm not going to tighten your elbows together
this time. But do not dare to turn away from me, or interrupt
Then she began, in an officious, yet ominous tone:
"Here's what's going to happen to you, and to us. As you
already know, you are only a worthless, piss-drinking sissy
whore. You're dressed in the clothes of a whore and you made
almost a hundred dollars for me, as a whore, servicing the men
in the bar. You avoided unimaginable punishment from me by
learning quickly how to satisfy them by giving them blowjobs."
"Consider what you have on right now," Mistress
continued. And she enumerated: "You're wearing a very short
white leather miniskirt that hardly covers your ass and
crotch. You're wearing a white sexy, silky camisole that
barely hides your cleavage. You're wearing four-inch spiked
heels that are locked onto your feet. Your pink stockings are
attached to that very tight pink corset that is laced severely
and then locked on you. That pink corset is holding in two
very pretty breast forms that are hiding those wonderful self-
tightening nipple clamps. When I take them off, and it won't
be for a while, your nipples will be well pierced, and then
I'll attach internally locking rings to them."
She gave that some time to sink in before she continued.
"And you're totally in my control. You're wearing a chastity
belt that cannot be removed without my approval. If you
misbehave, or simply for my own amusement, I can cause you
ever-increasing exquisite pain by pressing this little
button." She picked up her device, placed her finger on the
button, and I tightened by legs in horrible anticipation. She
chuckled. "You see?"
Then she laughed. "Oh, poor thing. You're trying to
answer but you can't." She undid my mouth extender. I could
barely close my mouth. It felt paralyzed. "Close your mouth.
Do it now," Mistress commanded.
And then she continued. "You were made to insert a
wonderful six-inch long dildo that will keep your asshole
nicely open. And is that dildo still inside you, locked to
your chastity belt?"
"Yes, Mistress. It's still inside me," I replied.
"And what are you wearing over your chastity belt?
"Mistress, I'm wearing my silky pink panties."
"And do you love wearing them?"
"Yes, Mistress, I love wearing my panties," I replied.
After all, how could I refuse?
"Good. Because from now on, you will be wearing only your
sissy whore clothing. And you're going to provide for us by
being turned into my own wonderful sissy whore sex slave.
You'll do whatever I want to whomever I say -- whenever and
"You see, I'm sick of smiling sweetly at horny, conniving
men at computer shows who ask insipid, stupid questions about
my company's products when the only thing on their minds is
getting into my pants." Her words stung as if she had slapped
me on my face. "And I knew I'd be able to find a dumb,
thoughtless little shit like you at the computer show to turn
into my new sissy whore."
Mistress went into the bedroom, and brought back a huge
heavy cloth sack, which looked like an oversized mail bag. She
placed it at my feet. "Lift up your right foot," Mistress
commanded. "Don't you love it when your pretty pink nail
polish glistens through your stockings?" Mistress asked.
I replied immediately by saying, "I love my pink nail
polish that Mistress makes me have." With a nod of approval,
Mistress unlocked the tiny silver lock on the shoe buckle and
took off my shoe. Then she did the same for the other foot. My
feet felt so relieved, now that they were out of those hideous
high heeled shoes.
Mistress bent over to open the bag. "Step quickly into
the bag," she ordered. "C'mon, left foot up, then right foot.
Don't make me punish you!"
She worked the bag up over my legs, my waist, then up to
my shoulders. She loosely tightened the drawstring at my neck.
I looked at her in horror when she picked up another gag. This
time, it wasn't the inflatable rubber gag, but, instead, a
penis gag. "Since you love sucking cock, you should be used to
this by now," she said, laughingly, as she pushed the rubber
penis into my mouth and buckled the strap around my head. "We
don't want you crying out, do we?" Mistress said rhetorically.
I moaned in desperation.
Mistress then went back into the bedroom and dragged out
a black steamer trunk with a large red and white "books" label
pasted on the side. Its dimensions were about four feet by
three feet by two feet. As she opened it, I could see shiny
black material lining the insides. I was startled. Oh no! She
couldn't...she wouldn't! She wasn't going to put me in there!
But I was wrong. With my wrists locked behind me, I
couldn't even begin to struggle. Mistress had planned this
well -- too well. I would only hurt myself if I had tried.
And, then, she could always press that horrible button.
Mistress pushed over the trunk and smiled up at me. She
then loosened the drawstring on the bag and quickly pulled it
over my head. She tightened it and then I heard the click of
a lock. I was plunged into total darkness.
I felt her push me backwards into a sitting position onto
what must have been the coffee table. With surprising
strength, she then maneuvered me down and into the trunk.
Bending my legs and folding down my neck, I was f***ed into a
fetal position. Then, I felt the trunk being closed, and I
heard it being locked.
After what seemed like hours, I felt the trunk being
lifted up, and I heard my Mistress say, in a very muffled
voice, that there were only books in the trunk. I felt the
trunk being dropped to the floor and then, shortly after, I
was suddenly at an odd angle, since the trunk must have been
uprighted and placed on a hand truck. I sensed movement and
the whoosh in my stomach as I assumed I was being taken
downward in the elevator.
More movement...a sense of being lifted -- into a car? --
a truck? -- a van? I was in darkness; I was breathing rancid,
piss-filled air -- the piss odor coming from all over me.
Despite the agony of my torturous cramped position...of my
bindings...of my penis gag...of my cruel chastity belt...of my
locked-in dildo...of my aching nipples...of my bruised and
battered body...I eventually fell into a fretful, troublesome
sl**p. I couldn't begin to recall the fearsome images and
nightmares that plagued me.
* * * * * * * *
The alarm clock went off, as it did every morning at
eight. I had been allowed to sl**p in my own bed last night,
though each nipple ring was chained and locked to its own side
of the bed and my arms were fastened to their loops tied to
each side of the chastity belt. Mistress was becoming more
intent on keeping absolute control over me and continued to
find numerous ways to enslave and dominate me.
Mistress came in cheerily, which might or might not be a
good sign for today. She gushed, "Do you know what today is?"
I looked up at her. I had no idea what she was getting
at. "It's our first anniversary," she replied. "A year ago
today, I began turning you into my little sissy whore."
Was it that long? Could that much time have passed? And
then the memories came flooding back at me:
During the first few days with her, there was an almost
unending round of chastisements and punishments. Mistress
worked hard to train me to please her without question, and
without any hesitation.
I was f***ed to urinate sitting down, for Mistress
refused to remove the chastity belt. I was taught to apply my
own makeup and nail polish, and to clean and care for our
"fine washables." It was my job to do all the housework and
cleaning. I learned what Mistress's schedule for me was, such
as what time I had to insert the dildo into my ass and lock it
to the chastity belt...such as when I was scheduled to orally
please her...such as when I had to prepare to receive a
whipping or caning, by fastening my own bindings, chains,
handcuffs or locks, just because she enjoyed inflicting pain
Mistress had made me sign over all of my possessions, my
bank accounts, and the few stocks which I had inherited from
my parents. She made me sign a power-of-attorney allowing her
access to my safe deposit box, which contained very little
besides a returned engagement ring and some gold jewelry. She
threatened to request a credit check to make sure I wasn't
holding out on her. She made me type up and send off a letter
of resignation, for personal reasons, effective immediately,
from my job. I hadn't had a high-ranking job and I didn't
think that I'd be missed much, anyway.
I remember spending hours in the afternoon basking -- or
should I say, "basting?" -- in the hot sun in her front yard,
in plain view of all passersby, wearing a bikini bathing suit
so that I would develop indelible tan lines -- and the color
of the suit always had to be the brightest pink so that I
could not fail to attract attention. Or the nights I had to
sl**p nude on the hard concrete floor in her basement, or
shivering in my sissy whore clothes while tied to a tree until
I remember being left for hours on end, hanging by my
outspread arms from rafters overhead, with my feet pulled
apart from below. Often I was whipped or caned or flogged
unmercifully while tied up, before being tied up, or after she
let me loose. Other times, I was f***ed to hold in an enema,
while I cramped and moaned in pain into my gag, as my stomach
became horribly distended.
I remember having to repeat, on countless nights, my
first unforgettable experience in the rough trade bar of our
first night together -- of having to give blowjobs at five
dollars a pop, and then being trussed up in front of the
urinals afterwards -- to have to accept, without question, the
debasement of being urinated upon.
I remember being dropped off on more than several late
evenings to be put out on the "stroll," which meant that I had
to earn money working as a street walker in my sissy whore
clothes down near the docks, or near the busy interstate, or
by turning tricks at a truckstop. I was made to suck
innumerable dicks of all sizes and colors until I earned my
keep and Mistress relented and picked me up. Sometime she
punished me severely for not earning "enough."
I remember being leased to a group of Asian "businessmen"
who found extra pleasure in hearing me scream from the
unendurable pain they inflicted on me from the "wonderful hot
kisses," as they put it, of American cigarettes. I found out
later that Mistress accepted extra money so that they could
permanently burn their brands onto my ass and the bottom of my
feet. I couldn't walk for days after that.
I remember visiting the petting farm, a tourist
attraction, which belonged to one of Mistress's friends, and
the humiliation of being fastened down in the breeding barn in
order to suck a bull's huge penis until he ejaculated in my
mouth. Another bull was brought over for me to orally excite,
and after, he was turned around and then I had to endure the
pain of having him impale me deep in my ass.
I remember the many "parties" I was brought to, where I
was rented out to act as hostess, French maid and all around
playtoy, and where I was f***ed to sexually service guests of
both sexes in the most denigrating, degrading and humiliating
And I remember, too, the hollow feeling in the pit of my
stomach when Mistress had gone out for the evening and left me
fastened to any one of her infernal devices -- her whipping
post, her exercise horse, or even stretched out on her rack --
and to know that she would be pleasuring, or be pleasured by,
someone else. And then later on, and often much later, I was
made to service her -- to worship her -- by obediently and
reverently lapping at her cunt with my tongue, and cleaning
out the cum left in it by her lover.
Mistress slapped my face and I returned from my reverie.
"Today's a special day. You've done well for us and I'm going
to reward you."
She unfastened my cuffed wrists from my chastity belt but
then used chains to attach them to the top two corners of the
bed. She locked leather cuffs to my ankles and used chains to
draw them to the other two corners. She then unlocked my
I was stretched out, face up, spread-eagled, on the bed.
Mistress got on top of me, straddled me, and started to twist
and manipulate the nipple rings. It had been obvious for a
while that my nipples had gotten larger, as well as my
breasts. I needed progressively thinner breast forms to fill
out the cups of my corset or my bra. "Those hormone pills have
been working miracles on your body," Mistress said as she
looked down at me. "Aren't you glad that I've been taking care
of you so well?"
Indeed, she had. She had made sure that I was well fed
and that I had properly taken my vitamins, as she put it. She
had made sure, all along, that my welts, my cuts, my abrasions --
all of the injuries that were inflicted on me by her and by
myriad others -- were cared for and treated. And she had
dressed me in the softest leather and the silkiest
Mistress dismounted, reached around to my waist and
slowly unlocked my chastity belt. She pulled it out from
behind, lifted it up closer to her face, and carefully
examined it, saying, "It looks like your steel chastity belt
has held up really well. It's certainly worth what we paid for
it." She pulled my penis out and up from the place between my
legs where it had been f***ed to remain for the past year and
started to caress it lovingly and tenderly. I felt a yearning
in my loins, but my manhood stayed small and shriveled. "I see
I'm going to have to cut down on those pills," Mistress noted.
She then opened a tube of lubrication and began to rub me
up and down. I started to become erect. "I want to feel you
inside of me." She then reached over, picked up a small
leather strap and tied it tightly around my cock and balls and
this made me much more erect. "Mmmm...that'll keep you
erect...just the way I like it."
She then mounted me, warning me not to get there until it
was time. The strap kept me hard as she began riding me. She
yanked and grabbed at my nipple rings until I screamed at her
for mercy. She slapped my face, though more lightly than
usual. I felt the heat growing between her legs and I felt her
increasing sense of urgency. Then she started bucking even
harder, and then she yelled, "Now!" and we both came --
wonderfully and explosively -- together.
I lay there, spent. Even as Mistress swivelled around on
top of me so that I would be compelled to service her orally
and to lick out my cum, I felt sated and, I have to admit,
loved. Despite all the indignities, despite the pain and the
humiliations and the degradations, I loved my Mistress. I
provided for her -- for us -- and, in return, she loved me in
her own special way. She took care of my needs and all I had
to do, in return, was to subjugate myself fully to her. All I
had to do was to give away my will to her.
"Happy anniversary, Sissy Whore," Mistress said, as she
loosened the strap around my penis, which slowly shrank back
to its former state. She waited a few minutes and then, once
again, picked up my chastity belt. I begged her to let my
manhood stay free and unencumbered, but I knew, down deep,
that she wouldn't.
Mistress's mind was unchanged. "You know you really need
me to lock you back into your chastity belt. I know that you
cannot live without it. Admit it to me!"
I was f***ed to say it out loud to my Mistress -- I was
obliged to say I wanted and needed to wear the chastity belt,
my ultimate sign of subservience -- and then I had to thank
her once again as she dragged my penis down between my legs
and locked it back onto me.
And it was then that I knew that she had, indeed, taken
my will -- and my soul and my heart and my love -- and that I
had allowed her to do it -- willingly, fully and without any
remorse. And we kissed.