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The Trouble with Fantasies
by Puppy Girl
Chapter 2
I couldn't think of any reason to argue, and I certainly had no place other than home to go.
Dressed as I was, I couldn't exactly go to the office or the health club after all. So I followed
Juan's instructions and went directly home. I wasn't really surprised to see in the driveway the
BMW that I had rode in from the club to the hotel, but I was still scared by it. For the first time
ever I entered my house not as its lord and master, but as a scared sissy, completely unsure of
what to expect.
Master Robert was sitting in a chair reading something and when I walked in he looked up and
smiled, "kneel, sissy."
I knelt immediately.
"Very good, I assume you understand why you should do everything I tell you."
"Yes"
Master Robert leaned over and slapped my face so hard I nearly fell, "What!?!"
"Yes, Master."
"Better, I had hoped when I read the letter you showed me in the bar that I had found a whore
who was already trained, but I guess not. What is your name, sissy?"
"I am sissy sabrina, cock sucking whore, Master"
"And I am?"
"You are my master, Master."
"Tell me your password to your email account and then go to your room and clean up. When you
are done bathing and shaving all hair except that on your head, put on the clothes I have laid on
your bed. I will come get you when I want to see you again."
I was very nervous as I went back to my room; I had never shaved my legs before, counting on
my choice of opaque tights to hide the little bit of hair that I had. So I was very happy that
Master Robert had expected this. Along with a scented bubble bath, he had provided a Lady
Venus razor and sensitive skin leg shaving cream as well as a pamphlet on shaving legs and
pubic area that had obviously been written for girls who were being raised by single fathers who
had no way of helping with this issue. I giggled as I shaved and wondered if I should call Master
Robert "Daddy", but then the seriousness of my predicament came to mind and I worked on
making sure I was shaved thoroughly. When I was finally clean and hairless, I went to see the
outfit I would be wearing for Master Robert.
It consisted of a red bra, panties, garter belt set and sheer red stockings, covered by a nearly
transparent white mini-dress that came just to the top of the stockings but hid nothing. I put on
the items and the red 5" heels that were with them, fixed my make up and wig and waited for
Master Robert's summons. As I waited I looked myself in the mirror and realized that I really did
look like a whore. I couldn't see any reason why men wouldn't want to pull over and pay to get
sucked by the vision I saw in the mirror. I wondered if that was what Master Robert had planned
for me. There was no question that I would have to do whatever he demanded. After all he had
pictures that would get me fired, disowned, even arrested depending on whom he chose to share
them with. To say nothing of what he might be doing with my computer and email account. As I
stood there contemplating this and looking at my image in the mirror, I noticed that I was
aroused, very aroused. The tent that my panties had become was the only blemish on the
feminine image before me. I wondered if Master Robert would mind if I took care of the
problem. He hadn't said not to, but somehow I suspected he would be mad if I masturbated, so I
just turned away from the mirror, sat on my bed and tried to think of anything nonsexual to calm
myself down. As I waited for Master Robert to summon me I remembered that Mistress had told
me once that a good slave always kneels, so I got off the bed and knelt facing the door. I don't
know how long I stayed there kneeling but eventually the door opened and Master Robert
summoned me into the living room and told me to kneel by his feet with my hands behind my
back.
"This is the position you will assume anytime you are in my presence, unless you are told
otherwise, do you understand?"
"Yes, Master."
"As you may have figured out, I run an escort service which specializes in transvestite whores,
you are now one of my transvestite whores. If you behave and do what I tell you, you can keep
your life pretty much as it has been. If you disappoint me, I will ruin your life. I can get you
fired, have your house foreclosed, and leave you homeless and penniless. Ellen used to have a
good job and a nice house, but she didn't learn how to behave soon enough. Now she is lucky to
have the job she has. It's a shame really, she behaves perfectly now, it would have been so much
nicer for her if she had learned quickly. I own you completely do you understand that, whore?"
"Yes, Master, I understand."
Master Robert left me kneeling as he went into my computer room, when he returned he had
something in his hand that looked like a kids toy, it had clear and pink plastic and a little brass
padlock.
"This is a CB2000 male chastity device, you will wear it at all times. Very few of your clients
will want anything from your sissy cock; those that do will be given a key. Otherwise you will
not need to have erections or orgasms and so you won't. If you behave well, you will sometimes
be rewarded with me giving you a key."
I didn't know what to say, so I said nothing as he put my cock into the device and locked me into
it, then he pulled it up between my legs, effectively removing any evidence of manhood. He
handed me my debit card and the keys to my car and said:
"Go to any tattoo parlor and get a couple of tattoos, one on your on right ass cheek that says
'Property of Master Robert' and one on the back of your left shoulder that says 'sissy sabrina' if
anyone you meet wants to fuck you remember that you are a whore. Also remember that you are
a one dollar whore."
As I drove around looking for a tattoo parlor, I knew I was in for an embarrassing encounter, but
was relieved knowing that at least neither of the tattoos Master Robert had demanded would be
visible unless I let them be seen. I finally found a place that I could park right beside, and I
hurried inside. The embarrassment I felt as I told the man what I wanted was magnified when he
noticed that I was not a girl, but a transvestite slave. The needles hurt as the tattoos were applied,
but I knew they were nothing compared to what I would get if I didn't obey Master Robert's
orders. After I paid for the tattoos with my debit card the tattoo artist said, "I bet your Master
expected you to be abused, but I am a professional, so I don't take advantage of clients."
He gave me some business cards to take to my friends. I thanked him and went back home to my
Master.
After I knelt before him and showed him my tattoos and gave him back my debit card, he
explained my new life to me. I was permitted to keep my job, as long as I behaved. I was
expected to wear feminine undergarments at all times however. Each evening when I returned
home, I would dress up completely in the outfit Master had selected and remain at home. If sissy
sabrina cock sucking whore had a client that night a call or email would explain where to meet
him. If I had no client I was free to do whatever I wished, of course I was to stay dressed in the
outfit chosen until I went to bed and must remain available until 10pm in case a client wanted an
escort at the last minute. I would also receive 1 evening off each week and 1 week 'vacation'
every 6 months. During these times I was still required to wear feminine undergarments, but
could otherwise do as I pleased (visit family, put in overtime at work, even date if I wished).
Weekends belonged to Master completely, if there was no client, there would be training or self-
improvement assignments to help me become a better whore for Master's business.
As far as the clients were concerned I was mostly going to be meeting clients who wanted their
cock sucked, since after all I am sissy sabrina, cock sucking whore. But he promised that if I
behaved and worked hard at the training, I could one day become more of an escort than whore,
and accompany gentlemen clients to events. However, Master stressed that whatever my
assignment, I would always be his slave and it would be wise to remember that. After all I didn't
want to end up working 12-hour shifts as a maid at a hotel just to keep from starving. All
financial aspects were between Master Robert and the client; I would be paid one dollar per
client by the company and was not to accept any tips.. If a client left a tip anyway, I was to give
the full amount to Master and would be punished for failure to make the customer think of me as
his slut instead of his whore. I didn't even want to think about the punishment I would receive if I
received a tip and didn't reveal it. The checks, like the one I had already received had to be
deposited into my bank account within 2 business days
"Do you understand your new life, sissy sabrina?"
"Yes, Master."
"Hold out your left hand."
I held my hand out and he placed a bracelet on my wrist. It looked like one of the magnetic
copper bracelets that are so popular these days for men and women, but it went all the way
around my wrist and looked like two coils infinitely intertwined. I had seen one on Ellen when I
was sucking her cock. Master told me to hold my hand still and left the room, when he returned
he used a soldering iron on the bracelet and told me, "This bracelet cannot be removed, even by
me. It is a unique design and is known by a few high rolling clients and fellow Masters. If they
see it and wish anything they will hold your hand and ask you, 'Which Master has bejeweled you
so exquisitely?' If this happens, you will obey any command given. It does not matter where you
are, or whether you are en femme or not. Even if you are on your vacation or with a client, you
will obey any order that person gives you. Whatever negative ramification you think might occur
by obeying will pale in comparison to what will happen if you don't. Do you understand, whore."
"Yes, Master. No matter what, if someone notices my bracelet and asks "Which Master has
bejeweled you so exquisitely?" I am to do whatever they command."
"You grasp things well, you may have potential. I doubt if you will follow Ellen's sad path to her
present pathetic condition"
I blushed at his compliment and said nothing.
He got up and told me to follow him and we went into the den, where he had me lay over the
coffee table with my ass in the air.
"You have done nothing to displease me, but it is important that a slave learn early what
punishments she can expect if she misbehaves. This is the paddle; I use it for minor infractions
that do not require additional punishments. When you are paddled you will count them and thank
me for each one."
Whap!
"One, thank you, Master."
Whap!
"Two, thank you, Master."
Whap!
"Three, thank you, Master."
Whap!
"Four, thank you, Master."
Whap!
"Five, thank you, Master."
Whap!
"Six, thank you, Master."
Whap!
"Seven, thank you, Master."
Whap!
"Eight, thank you, Master."
Whap!
"Nine, thank you, Master."
Whap!
"Ten, thank you, Master."
"You're welcome, whore. Now kiss the paddle."
I kissed the paddle as he held it in front of me. I was not surprised that my cock was hurting as
bad as my ass as it strained against the chastity devise.
"This is the riding crop, it will be used for more serious offenses. If I have to use this, loss of
privileges will also be part of the punishment. When you are cropped, you will count them and
apologize."
Whack!
"One, I'm sorry Master."
Whack!
"Two, I'm sorry Master."
Whack!
"Three, I'm sorry Master."
Whack!
"Four, I'm sorry Master."
Whack!
"Five, I'm sorry Master."
Whack!
"Six, I'm sorry Master."
Whack!
"Seven, I'm sorry Master."
Whack!
"Eight, I'm sorry Master."
Whack!
"Nine, I'm sorry Master."
Whack!
"Ten, I'm sorry Master."
Whack!
"Eleven, I'm sorry Master."
Whack!
"Twelve, I'm sorry Master."
Whack!
"Thirteen, I'm sorry Master."
Whack!
"Fourteen, I'm sorry Master."
Whack!
"Fifteen, I'm sorry Master."
"Very good, whore. Now kiss the crop and then suck it."
I kissed the crop and licked it like a cock. The good news was that my cock was no longer
straining against the chastity devise. The bad news was that my ass was burning and tears were
starting to run down my face. I continued to lick the riding crop until Master inserted the handle
in my mouth and I sucked it as if it were a date's cock.
"This is the cane, if I have to use it. I will most likely also start ruining your life. When I was
forced to use it on Ellen is also when I sent her supervisor a picture of Ellen's male alter ego
sucking her supervisor's husband in a public park. She was fired shortly thereafter and had to ask
me to help her find a job. When you are caned, you will count each one and beg me to forgive
you."
Whoosh!
"One, Please, forgive me, Master."
Whoosh!
"Two, Please, forgive me, Master."
Whoosh!
"Three, Please, forgive me, Master."
Whoosh!
"Four, Please, forgive me, Master."
Whoosh!
"Five, Please, forgive me, Master."
By the time the fifth caning landed, I was a blubbering crying mess; I was glad that Master had
understood my blubbering enough that he stopped the caning.
"Kiss the cane and suck the handle well, the better you lubricate it the less it will hurt."
After I had sucked it and drooled on it for a few minutes, he told me to stick it in my ass and
began taking more pictures. I realized that these pictures also had nothing in them to indicate
duress. They were simple pictures of a horny transvestite penetrating her ass with the handle of a
cane. There was absolutely no reason to think I could convince anyone that any of this had been
done against my will. I was completely at Master Robert's mercy. I knew it and he knew it and
he knew that I knew it. He then placed a hot pink pager on the coffee table I was laying over.
"This is your pager, you will carry it with you at all times. If you are paged you must call the
number within 10 minutes no matter what. You will stay exactly where you are with the cane in
your ass until your pager beeps. Then, you are to remove the cane, clean the handle and place it
in your closet.
Then you are to check to see if you have any new email.
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