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The Trouble with Fantasies
by Puppy Girl
Chapter 1.
It all started with the email Mistress sent me. Okay I guess technically it all started when I began
to serve her via email. She had a website and for a small monthly fee she would give
assignments to her sissy slaves. I had done all the assignments on her website and had now
graduated to receiving personal emails with instructions on what she expected me to do next. Of
course being email she couldn’t tell if I really did the assignment or not but I really enjoyed
being her slave and I always performed the assignment for real. I had purchased panties at
Victoria’s Secret, admitting to the salesclerk that they were for me; tried on lipstick at a Dillard’s
counter; worn diapers and wet myself in public all just because Mistress assigned me to. I had
also begun to wear panties, pantyhose and bras or bodysuits under my clothes to work and other
places, and had been out in public totally dressed many times.
The next assignment went way beyond any of these. I’ll just let you read the email…
"Dear sissy sabrina,
I am pleased that you have followed all my instructions thus far (and you better not have lied to
me or you will be punished). It is time to take the next step. You are to find a man and have him
give you at least one dollar in exchange for a blowjob. If you must loan him or give him money
to do so that is okay, but he must give you money for the blowjob. Additionally, you must get
proof of having done this. Have someone take a picture with him in your mouth, or a picture with
his cum on your face. Do not use a digital camera; either a Polaroid or regular film camera
should be used. (This way if I decide to show your friends or coworkers the pictures you can’t
claim they are doctored.) I want at least 10 pictures. If you find a customer who will take 10
pictures, those will be fine, if a trick will only take 1, then you must find another customer.
When you have 10 pictures, email me and I will tell you where to mail the pictures. Until you
have these pictures do not contact me again. When you have the pictures, you will begin to use
the name ‘sissy sabrina, cock sucking whore’ on all correspondence. By the way, your credit
card will be billed monthly even if I never hear from you again.
Sincerely,
Your Mistress"
My first thought was to write her back and cancel, after all I was a sissy slave not a cock sucking
whore, but the longer I thought about it the more I thought that if I was going to be a sissy slave,
I couldn’t expect to only do things that I enjoy. I had enjoyed all of her previous assignments,
even the ones that didn’t initially appeal to me, so I decided to do it. Even after deciding to do it,
it still took me weeks to get up the courage. Finally one spring evening I decided to go for it. I
dressed as sexy as could, black leather miniskirt, pink blouse, pink tights and 5" high heels and
drove to a gay and lesbian bar a few blocks from my house. As I checked myself in the mirror, I
thought I was very passable and looked like nothing more than a whore in search of a trick. I got
to the bar pretty early (about 7) found a table to sit at where I could be seen from most of the bar
and ordered a glass of wine. After all, it wouldn’t help to hide, I was hoping someone would
approach and I wouldn’t be reduced to propositioning strangers and facing the rejection that can
go along with that. I had been there about 45 minutes when a girl came over and sat down beside
me, put her hand on my thigh, said her name was Lisa and asked my name. She was beautiful,
tall with long black hair and a great body, but of course wasn’t at all the type I was here to meet
(nor I, her), so I didn’t even bother to use my femme voice when I told her my name was sabrina
and I was looking for a man. She was very polite as she wished me luck and moved on.
About 5 minutes later a guy came over and sat opposite me at the table and asked, "what’s a nice
girl like you doing in a place like this?"
It was such a cliché, I couldn’t help but smile as I replied, "maybe I’m not really that nice."
"Touché, and maybe you’re not really a girl either."
"Touché, yourself", I tried to reply gaily but I was hurt that he had made me and I guess it
showed.
"No honey, you pass just fine and you’re gorgeous, its just that very few real girls come in here
dressed like that and if one did Lisa would be exactly what she was here to find."
I blushed and we introduced ourselves and he asked me what I was here to find. Pulling a trick
from one of Mistress’ earlier assignments I just reached in my purse and handed him a printout
of the email she had sent me. The only other things in my purse were a Polaroid camera, my
make up, keys, 5 twenties, 10 ones and my drivers license (it is illegal not to carry id in this state
and crossdressing is not a crime).
He read the email several times and then smiled, "So have you sucked many cocks, sabrina?"
"No, but there’s a first time for everything", I said trying to sound cavalier.
"Yes there is, indeed there is. Do you have a room we can go to?"
I blushed, "I hadn’t thought of that, sorry."
"Well, it takes time to learn to be a whore, I suppose, let me say goodbye to my friends and I’ll
meet you in the parking lot."
His name was Robert and he was a good-looking guy with blonde hair and a slight build about
5’7" tall. If I was going to have to suck a cock for my Mistress at least I hadn’t had to suck off
some fat slob, so I was feeling pretty lucky as I finished my drink and laid 4 dollars on the table
and went out to the parking lot to wait for Robert. He came out and escorted me to his BMW and
drove to a Holiday Inn on the freeway. After he checked us in, he escorted me to the room and
sat me down on the bed.
"Since I am the customer and you are the whore, you have to do what I tell you, right?"
"Yes, Sir." I replied, getting into character.
He tied my hands behind my back, had me kneel between the two beds and tied each ankle to a
bed. He then pulled his cock out of his pants and rested it on my lower lip. "Beg me to make you
a cock sucking whore, sabrina"
"Please Sir, please let me suck your cock, let me be your whore."
He forced his cock inside me and pumped it for about 10 minutes. While I was sucking him he
took a couple of pictures with my Polaroid, then he pulled out and sprayed his cum all over my
face. He took a couple of pictures of that, then he removed my wig and took pictures with my
face covered in cum and no wig, and then put his cock back in my mouth and took more pictures.
Then he replaced my wig, placed a ball gag in my mouth and blindfolded me. I heard some
rustling around the hotel room and then the door opened and closed and I became very afraid of
what I had gotten myself into.
After what seemed like hours, I heard the door open and close again and the blindfold was
removed, and I saw Robert standing there in front of me with his cock dangling in front of my
face.
"Suck me, whore."
I sucked him again and again he took pictures; lots of pictures. In some, it was obvious who I
was and what I was doing, and in most you could not see that I was tied up. I looked like I was
doing exactly what I wanted to be doing, especially when he had me smile as I licked his cum
from my face and sucked on his fingers as he fed me droplets of cum and I appeared to be
begging for more. He then went around behind me and began nibbling my ears and neck, in spite
of my situation I started getting erect and he lifted my skirt, reached in and began fondling my
cock. After a few minutes I knew I was about to cum with this man whose cock I had sucked
giving me a hickey and jacking me off and there was nothing I could do to stop it from
happening. Just before I came he stopped jacking me off, put one of the hotel’s courtesy cups
under my cock and started taking pictures again, some of which only showed my cum drenched
face and my obviously excited penis. After all of my cum had drizzled into the cup, he put the
ball gag back in my mouth, checked the ropes that had me tied, then went toward the door. As he
turned the knob he looked at me with an amused smile and said, "I took the $96 in your purse, it
didn’t quite cover the rent on the room and the other expenses, but you can owe me. The maid
usually comes between nine and noon, so you should have some time to accept that you are now
sissy sabrina, cock sucking whore before they discover you and untie the ropes. Its only midnight
now, so you have at least nine hours to keep reminding yourself that you are sissy sabrina, cock
sucking whore. I’m sure your Mistress will be pleased."
There are no words to describe the effort I made to try to free myself from the bonds that held
me, but it was clearly hopeless. After only about an hour or so I realized that sissy sabrina, cock
sucking whore had not only sucked cock twice tonight, but sissy sabrina, cock sucking whore
was also going to be discovered by the hotel maid, bound with a man’s cum on sissy sabrina,
cock sucking whore’s face and sissy sabrina, cock sucking whore’s own cum in a cup beneath
her prick. I don’t know how, but sissy sabrina, cock sucking whore eventually found sleep and
only woke up when sissy sabrina, cock sucking whore heard the keys rattling in the hotel room
door.
The maid walked into the room and gasped when she saw the bound girl on the floor between the
two beds, but then she chuckled when she saw sissy sabrina, cock sucking whore’s little prick
over the cup with cum in it on the floor.
The maid was tall with long blonde hair and large breasts, her breasts were her best feature and
she had her blouse unbuttoned to make sure they were shown to nice advantage. Her nametag
said her name was Ellen and that she had 4 years of service with the hotel. She removed the gag
and asked, "Are you okay?"
"Yes, I’m okay, I can explain its okay, can you untie me"
"You don’t need to explain, but you do have to tell me, were you raped, or is this part of some
kinky sex game?"
"Well I wasn’t raped, no, this isn’t what I expected but no I wasn’t raped."
"Well see, if its rape, I need to call the Police to untie you, otherwise evidence could be lost, and
the rapist could go unpunished."
"No, no, it wasn’t rape, just a little joke that went too far, if you’ll just untie me, I’ll be okay."
"You’re sure you’re okay, you’re not just saying that because someone threatened you?"
"No really, I’m fine just untie me and I’ll go away. Its okay I promise."
The maid said she’d be right back, then left the room, sissy sabrina, cock sucking whore noticed
that she didn’t lock the door behind her or even pull the door closed tight, sissy sabrina, cock
sucking whore thought about calling out to her, and then decided not to.
Eventually, the maid returned with a digital tape recorder and said, "the manager is worried
about lawsuits, so he wants you to record a release to make sure the hotel isn’t held liable for
damages if you change your mind and decide it was rape after all."
She put a piece of paper in front of me and told me to read it using my name where it said "your
name here"
I had no choice so I read:
"My name is sissy sabrina, cock sucking whore and I was tied up in a Holiday Inn in Dallas as
part of playing consensual sex games with a partner. I have not been raped, or a victim of sexual
assault at this hotel, nor have I, sissy sabrina, cock sucking whore been held against my will by
any employee of the hotel or anyone associated with the hotel or any client of the hotel. I, sissy
sabrina, cock sucking whore accept total responsibility for any injury or inconvenience which
occurred at the hotel, as it was part of a sexual game which I, sissy sabrina, cock sucking whore
agreed to participate in of my own free will and for my own enjoyment."
Ellen shut off the tape recorder when I finished and laughed, that’s very sweet, but the hotel
needs you to use your real name when you read it. I blushed as I read it again using my real
name. I was surprised that she left without untying me, but assumed, she went to make sure the
manager was happy with the release and wouldn’t want her to call the police.
When she returned, she locked the door behind her, walked up in front of me and said, "so sissy
sabrina, cock sucking whore, how long have you been a whore?"
I didn’t know how to react, and just stammered as she lifted her skirt dropped her panties and
revealed a huge cock, "Master Robert helped me get this job, I assume that sissy sabrina, cock
sucking whore is a present he left me for a reason, so I suggest you suck like you mean it. After
all, it’s my choice whether you get untied or not"
I didn’t have to be told what to do, Ellen’s cock was longer than Robert’s had been, but not as
big around. I sucked the transvestite maid aggressively, not surprised at all when she (he?) pulled
out and sprayed her cum all over my face, adding her? cum to the cum Master Robert had
already left there. After she freshened up, she untied sissy sabrina, cock sucking whore and said,
"I’ll be back in 30 minutes, please get cleaned up and check your belongings. The hotel will
require you to sign a release that nothing has been disturbed and that your stay was without
problem."
After she left, I realized that in order to get back to my car which was still parked at the club,
sissy sabrina, cock sucking whore was going to have to go out en femme and somehow get back
uptown without being made, so sissy sabrina, cock sucking whore went to get her purse to
reapply her make up. After applying her make up and putting it back in her purse, she noticed not
only was her purse devoid of money, her drivers license was gone and there was a business card
and a check in the purse. The business card was for Escorts Plus, and said "feminine
companionship with a little extra" and the check from the same company, was made to my real
name and in the memo line stated, "For services rendered as sissy sabrina, c.s. Whore". The
amount of the check was one dollar.
When the maid returned to the room, I was looking as decent as possible, given the
circumstances and happily signed the release which stated that my belongings had not been
bothered during my stay. Again, I had been required to use my real name.
I was just starting to walk across the parking lot when Ellen came to me and asked, "do you have
a ride home or money for the bus?"
When I said no, she asked if I wanted her to see if one of the staff could drop me off.
I thanked her, and the maid ran back into the hotel and soon came back and told me that Juan, the
bellhop would take me home if I wanted.
Juan was about 6’3" with extremely dark complexion and coal black hair it was obvious that he
worked out as I could see his muscles rippling even through his bellhop suit. I got in Juan’s van
and told him how to get to the club where I had left my car. About half way there, Juan pulled
into a parking lot in a very seedy area of town and told me, "you are sissy sabrina, cock sucking
whore. If you don’t want me to leave you here, you will be my whore."
I could see no choice so I crawled down and started sucking him off. While I was sucking him,
he pulled my hands behind my back and used a tie wrap to bind my hands behind me. His cock
was longer than Ellen’s and wider than Robert’s and it was all I could do to take it in my mouth.
After he came in my mouth, holding his cock in me to make sure I swallowed his cum, he
pushed me to the back of the van, threw me face down and tied my ankles to either side of the
van.
I lay prone in the van while it bounced through many streets. Juan pulled the van into the parking
lot, parked beside my car, stopped the van, opened the back door and told me, "you are now sissy
sabrina, cock sucking whore, one of Master Robert’s girls, the sooner you accept it, the sooner
you will be happy. He then untied my legs, pulled me out of the van cut my hands free and
handed me my purse.
"Master Robert said for me to instruct you to go directly home from here."
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