The Skirt Chaser Chronicles 1 Sara s Story
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The Skirt Chaser Chronicles: 3 Sara's Story Part 2 free porn video
The Skirt Chaser Chronicles:
2. Sara's Story: Part Two:
You will recall in the first part of my story how I tricked my boyfriend
Paul into becoming a transvestite and a stripper called Paula. I was
pleased at how I had been able to undermine his conservative public
school values with some small items of women's clothing and release his
inner woman. I was fairly sure that Paul was not a transvestite nor had
any intention of becoming one before I helped create Paula. I believe he
viewed transvestites as betrayers of his public school education and
masculine identity and as a worthy of contempt and applied a similar
perspective to homosexuality. I was about to apply what I had learnt
from Paula on a bigger scale.
Before we went to the seedy bar I was getting bored of Paul and about to
dump him but Paula is, however, an adrenaline junkie and takes risks all
the time and in her I have found a soulmate, a lady with balls,
literally, and unlike Paul she takes me places I might think twice about
going to, but I get ahead of myself.
I was initially upset though at how the owner of the seedy bar where
Paula did her striptease had taken money from me to select Paula as his
stripper but then forced me into becoming a stripper too. In doing this
it felt to me like I had effectively paid the owner to turn me into a
stripper against my will but in a room full of men and with the owner
calling me up to the stage and dressed as a French Maid I really felt
that I had no alternative.
I had a Doctorate in English literature from a University you would have
heard of and I doubt if the owner had even passed any exams before he
left school. He would only let me call him the owner and he was such a
stubborn and uneducated man. When he was not squeezing Paula's ass, my
ass or one of the other girl's asses he was undressing us with his eyes.
He would insist on French kissing any one of us whenever he felt like it
and if he felt a girl (or whore as he called us) had not performed well
he would get a bucket of water full of ice cubes and throw it over her
before telling her to go back on stage and make him some money. In case
you haven't seen "Showgirls" (which was on constant repeat on the only tv
in the bar) the effect of the ice is to make a woman's nipples hard and
men are more attracted to erect nipples particularly on a woman in a wet
t-shirt. If you had had the bucket treatment you were handed a t-shirt
with for example if it was a Wednesday "Wednesday night's wet t-shirt
competition winner" written on it and there were t-shirts for every night
of the week. The t-shirt was handed to you from the inside of another
bucket of ice-water (just to ensure it was wet!).
Then there was the fact that after our first performance he had taken
Paula and my clothes and not returned our clothes to us forcing us to
spend the night in his bar with little but panties and a dressing gown to
wear. And he had drugged us! Well perhaps that was unfair he had simply
offered us the drugs and not told us about the side effects and left it
to both of us to decide whether or not to take the drugs having suggested
the drugs would replace the meal we had missed. The upshot had been,
though, that neither Paula nor I had been able to resist signing
contracts to perform at the seedy bar for a fortnight (a week longer than
he had suggested before we took the drugs) and the owner got a an unusual
French Maid act as a result of that deal who had contracted to perform at
his bar and to pay him a commission to do so. I understood that we were
the most popular act he had had.
Also I was pretty sure that he was stealing my tips as he groped my ass
but we still made good money and I had started to enjoy being groped by a
real man like the owner. At the end of the second week I got the bucket
treatment. I had been standing there in stilettos and nothing else other
than my panties and dressing gown when the owner said:
"Sara, hang up your dressing gown for a minute and let me look at you."
I had long got past resenting him staring at my almost naked body
(although I did on the first night) and would happily sit or stand
virtually naked in front of him.
"You know you are the only whore who paid me to turn you into one! As
soon as I saw you I knew you were na?ve about this game and open to being
manipulated as much as doing the manipulating and you made that clear
when you told me of your plans. If you did not want to strip you should
not have come to a strip bar dressed as a French Maid particularly with a
boyfriend whom you had forced to dress the same way and who you were
forcing do a striptease first as he was the only one that could have
saved you from having to become a stripper. And your obvious na?vity but
"I have been to University" look was always going to go down a storm here
and as soon as I met you I knew that I would have you getting out your
tits for the lads that evening."
At that point I felt shame and that I had been exploited by someone whom
I had underestimated and who had taken complete advantage of me and I
know I went red. I was just thinking what to say in reply when the
contents of the bucket of water hit me like a slap in the face except it
was all over my body. As the water hit me I was trying to protect my
breasts with my arms out in front of me and ducked my head down but it
had only served to ensure all my hair was wet and my nipples were already
erect from the ice before I put my arms down to my side as he had emptied
the bucket over me by then.
How should I describe this? I felt as humiliated as when he first made me
strip? Or I felt as humiliated as when he first grabbed my ass?
Actually this was worse, he'd used ice to make my nipples erect by
throwing a bucket of water over me. I had become sexually aroused in the
most humiliating way I had ever been sexually aroused!
I should have said something first but instead, having just thrown a
bucket of icy water over me, he was talking of firing me from a job I had
had to pay him to give me!
"Sara, I want to keep you on but I am losing money on your act as you
have become more experienced at this and less na?ve looking and this
causes the punters to lose interest a bit and the nature of this work is
also making you look dumber. At least wear some student-like glasses to
look less dumb!"
He was calling me dumb! Then I thought perhaps he had a point as I
thought of myself as intelligent but I was getting my tits out for his
customers each night and he was the one making money out of me doing
this, maybe I was a bit dumber than I thought I was. But I also thought
that this was a bit unfair as he was still making money from me and he
was simply complaining that he was not making as much as when I started.
We girls had to clean the place as he would not pay a cleaner to do so
and we also had to buy all our own costumes. I could do any job. I did
not have to do this. There was however something that compelled me to
want to carry on.
"Now put on your t-shit, my little whore, as tonight's winner and go and
make me some money."
Over the course of the next week I performed for free each night because
I wanted him to keep me on but Paula did not come with me as she was
"considering her options" and I had managed to "win" the wet t-shirt
treatment for the whole week. At the end of the week I had a cold and
the owner said he could afford to pay me some sick pay whilst I got well
and to take a week off and he gave me some money (although he made more
in one night off me working for free).
I should not have gone back but I was hooked.
The owner said he had some plans for my act. "Did you see that the local
boy's public school is advertising for a drama teacher? You studied
English didn't you? You'd be ideal or at least you are the only whore I
know who would."
This was his way of encouraging me to become the drama teacher in an all
boys' school. He said that Paula was able to dictate terms as she had
worked out how to work the audience and I should learn a trick from her
and then go one up on her.
His idea was that I get the boys from the school to become transvestite
strippers. So I applied for the job and was surprised to get it but I
did not feel comfortable with bringing the boys here or recruiting
dancers for him.
On my second week in the job at the school I noticed one of the brighter
lads from my sixth form drama class watching me perform at the seedy bar.
He was there with a young man who looked a year or so older than him.
OK I thought. If they are old enough to watch me perform they are old
enough to bring here. I made a mental note of the boy's face.
The next day the Head of English said they were trying to organise the
school play. This was generally done with the old boys in after school
or extra-curricular activities. Would I consider running it? What would
it involve I asked? What play were we doing?
I was told that I could choose. So I decided to offer them "As you like
it" or "The Rocky Horror Picture Show". I began by asking if anyone knew
either play. It turned out none of them did. I sold them "The Rocky
Horror Picture Show" by describing "As you like it" as a Shakespeare play
and "The Rocky Horror Picture Show" as an all singing all dancing show.
It had been arranged for my drama class to have a week off school to
rehearse.
"Who wants to audition for the lead role?" I asked.
I was spoilt for choice. I saw the boy who had watched me at the seedy
bar and selected him and his friend and the most handsome four other boys
in my class.
"Ok boys," I said. "I want this to be a new experience for you all and
it will involve method acting. Here is a bag for each of you. Now come
with me to the rehearsal studio. I will drive you there in the school
van."
It was late for them and none of them noticed when we arrived at the
seedy bar, where we were, so I parked out back. Then I led them all
through the back door to the changing room.
"Now in your bags you will each find a lipstick. I want each of you to
apply lipstick to your lips and then I will apply the rest of your make-
up." I spent some time doing their make-up like Frank'n'Furter in the
Floor Show part of the play. Then I said they would each find special
underwear to go with their costumes in the bag and I would go out whilst
they put it on.
"But these are girl's panties," said the boy from last night.
"What's your name?" I asked him.
"Jason," he said.
"Well the first rule in here is never give your real name so step over
here and kneel down as I rename you Janice" I said spraying him with my
perfume. "And yes, they are girl's panties and if you want the lead role
you will put them on before the other boys but wait until I leave the
room!"
"Yes Miss," he replied.
I went out whilst they stripped off their clothes and put on their
panties.
Then I said, "It is time to put on the rest of your costumes. You are
all auditioning for the lead role which is the role of a transsexual
transvestite called Frank'n'Furter."
At that point I knew I had got them because I knew they shared Paula's
values. The thought of being a transvestite or a homosexual was a
betrayal of their value system but here they were doing just that.
Auditioning for the role of a bisexual transvestite! The quandary for
them was that on the one hand they were revolted by transvestites and
gays but on the other they could not lose face in front of me and had to
try to pretend that their fragile virgin teenage masculinity was not
threatened by wearing lipstick and panties and the rest of the outfit.
They were just discovering their pearl necklaces, elbow length sequined
opera gloves, lace bras and basques. (I had given them bras for two
reasons:
1. To look like they had real breasts and fill out the breast part of the
basque and
2. To comply with the owner's dress requirements for transvestites.)
I helped each of them into their basques and showed them how to unhook
them quickly from the front. They were confused by the garter straps and
I threw each of them a packet of fishnet tights and said:
"Listen up trannies, as far as I know each of you is getting to enjoy the
sexy feel of a woman's underwear for the first time. Now you have to be
careful putting on fishnet tights. You roll them up in a ball first and
poke your feet through. Then you put your thumbs in each side and pull
them up until they are level with your basque garter straps and clip the
stockings to the belt. Now each of you needs to wrap a feather boa round
your necks and slip into the stilettos that the drama department has
bought you."
I liked the fact that the school was paying part of the costs of turning
its boys into transvestites.
"Now I need to get to know each of your names to give you a tranny name.
You, boy, Janice's friend what's your name?"
It almost did not seem to be right calling what looked like a girl in her
underwear a boy.
"Joel," he said.
"I name you Joelle," I said spraying him with perfume.
The other boys were renamed Janet, Magenta, Columbia and Dr Scott (they
weren't suitable to play Frank'n'Furter as I could tell when I got them
into their make-up).
"While we are here you are each to only use your tranny name and refer to
each other in the feminine," I said.
I gave each of them one of the pills that the owner had given Paula and
me on our first night here.
"This is a meal replacement pill," I said. They each swallowed one.
"Sometimes it has side effects and causes hallucinations. But normally
you should just feel like you have eaten a meal."
"Now through in the next room is a stage. The place is empty but imagine
you are in a strip bar with an audience of men. Your imagination is a
powerful thing. If you are hallucinating some of you may think that
there are real men watching you. Some of you may even think that you see
me in front of you dressed the same way and taking my clothes off. Your
character, Frank, would be only too keen to get the attention of the men
he is performing before. So you boys need to pretend that you are also
keen to get the attention of the men that you are performing in front of.
I will lead and I want Janice on my left and Joelle on my right. Then
Magenta and Columbia next to Joelle and Janet and Dr Scott next to
Janice."
"You have to lean forward more in your stilettos than you are used to as
boys. It is like standing on your tiptoes the whole time and will really
help to strengthen your calf muscles. Tonight boys you will dance to
"Rose tints my world" and you should follow my lead until you have only a
bra and panties left on."
I then showed them how to dance "Rose tints my world" in stilettos. As I
suspected Janice and Joelle were more proficient.
The owner then knocked on our changing room door and said "Ladies, two
minutes."
Then we were called to the stage.
I saw Paula in the audience with a video camera and in her Maid's uniform
ready to film my act.
The owner announced, "Miss Sara and her class from your local boys'
public school." I walked onto the stage wearing my school teacher's
blouse and skirt over my Frank'n'Furter costume and carrying a cane (it
was funny as a woman to be playing a man dressed as a woman) and I then
said:
"Boys, assume the position."
And my trannys then came up onto the stage in their costumes to wild wolf
whistles from the audience. At that point the owner threw a bucket of
water over me as I had arranged with him beforehand and I stripped out of
my blouse and skirt to reveal my now wet costume. I saw each of the boys
get tents in their panties before a prearranged drenching happened to
each of them as the music started. I had not explained to them that
"Rose Tints My World" was performed on rather wet costumes and wanted to
see how they coped. They did surprisingly well!
As we came off stage the owner gave each of the boys a dressing gown. I
knew what was coming next, he wanted them to perform for him. The boys
got back to the changing rooms and looked for their clothes but instead
found towels, panties, pantyhose, padded bras, stilettos, skirts and
blouses.
"What's happened to my clothes?" asked Janice.
Knowing the owner liked the act I explained, "I have arranged for you to
stay here for a week. As this venue is usually used by ladies the spare
clothes kept here tend to be for ladies. Also as the audition at school
took longer than I thought, as so many of your classmates wanted your
places, I am afraid there wasn't time to allow you boys to pack before
coming here. Also I thought it would help you get in character more if
you were to spend the week, as it were, en femme. I have therefore
arranged for your boys' clothes to be dry cleaned so they are clean when
you go back to school. However if any of you wants to go back I can
drive you back this evening but it will have to be dressed as a girl."
Grumbling to each other they dried off and got dressed and once they had
done so I came back in and rearranged their make-up.
"Now boys you are probably wondering why you got wet. This is one of the
hardest songs to perform from the show as it involves dancing in
stilettos on a wet stage. My boyfriend was out there with the owner
filming the show so we will now watch it together. I know each of you
enjoyed it because the tape shows you were all rather, how should I put
it? Erect."
As I was saying this I noticed that Janice and Joelle went rather red.
I took them apart from the others and asked if there was something that
they had not told me.
Janice spoke, "I thought we recognized this place," she said. "Joelle
and I are sisters and this is our father's bar. We are both enjoying
this but we realize what you have done to us and that the audience was
real."
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