Sissy Sabrina Goes Out On The Town 2 The Trouble with Fantasies
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Sissy Sabrina Goes Out On The Town ? by: Sweet Sabrina
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 clich?, I couldn't help but smile as I replied, "Maybe I'm
not really that nice."
"Touch?, and maybe you're not really a girl either."
"Touch?, 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, it's 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. He 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. It's 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 it's 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."
Aspen
- 23.07.2022
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