The Skirt Chaser Chronicles 2 Paul s Story
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The Skirt Chaser Chronicles: 1. Sara's Story free porn video
The Skirt Chaser Chronicles, 1. Sara's Story: Part One, My name is Sara.
I had been dating Paul for a few months when this story begins. At first
he had been really romantic and bought me flowers and things. Lately I
had started to notice when we went out to the pub that he had these
wandering eyes which tended to follow any pretty girl in a dress.
So about a month ago I asked him about this. I said, "Paul, don't you
think I'm sexy? Why do I get the impression I am just a stop gap before
you move on to someone else? Why are you always looking at other women?"
He replied, "Sara, I was a boarder at an all boys boarding school so
generally the only women we saw in a skirt were our mothers and the
matron (who was old enough to be our grandmother). So now I am out in
the big wide world it is only natural that I am attracted by women in
skirts. Would you prefer I was homosexual like a lot of my classmates
and eyed up men?"
That could be arranged I thought. Maybe he might then introduce me to
some nice gay men who are considering becoming heterosexual or who have
bisexual friends.
"No, I want you just for me," I said.
The truth was I was getting a bit bored of how he had stopped paying
attention to me so I had stopped making an effort and wore trousers
whenever we went out. He had tried to encourage me to make an effort and
to wear a skirt but I refused to do so. At the time I had a group of
girlfriends who had all met boyfriends who they had been with for at
least six months and my relationships did not seem to last as long. I
hoped that Paul had some friend he would introduce me to and then we
would break-up.
I had made clear to Paul that I would not be having sex with him or
anyone else for that matter until I got married. Being the product of a
public school education he was very conservative in his values and
understood and respected my stance on sex before marriage but I think he
hoped he would win me round and I had led him on a bit saying we might go
some of the way.
One Sunday night we were talking in the pub "You know I find a young
woman in a skirt and pantyhose or stockings attractive but there don't
seem to be as many girls around as before I started being a boarder."
Paul mused.
"Oh really, how many would you say that you see on an average night in
the pub with me?"
"No more than 3 or 4."
I was confident Paul had underestimated the popularity of skirts.
"Ok. Let's make this interesting," I said. "We will come to the pub
every night this week. If we see 10 girls tonight you will wear
pantyhose yourself until closing time tomorrow. If we see 20 girls
tonight you will wear pantyhose on Tuesday too. A girl in trousers
allows you to discount a girl in a skirt. The same will apply each day
but the score can only carry forward for one day if it is a low score.
So say you only saw 4 tonight but saw 7 tomorrow you would be wearing
pantyhose from Monday night and for the following day until closing time
as the average for both days was higher than your estimate. If then on
the Tuesday you only saw one girl for example then you would be entitled
to remove your pantyhose that evening after closing time as the Monday
night girls had landed you in pantyhose then and would no longer count on
Tuesday night but if you had not wound up in pantyhose the previous day
the girls would count towards the following day. If on any day you are
wearing pantyhose you will include yourself in the "girls in skirts and
pantyhose" count and your score would therefore increase by one girl. If
you go two consecutive days in pantyhose you will then have to wear an
additional item of female clothing the following day if you are to wear
pantyhose again and each additional item of clothing will count as a
"girl in a skirt and pantyhose." If you go three consecutive days you
will have to put on a second item of female clothing and you will now
count as three girls."
"If you go a week without wearing pantyhose I will dress as a French maid
before leaving home and accompany you to that seedy pub across the road
where I will dance a striptease and I will arrange for you to be allowed
to video the entire evening."
"Deal!" he said. He was really eager to see me as a French maid stripper
and had not thought through how this would work out for him.
I then wrote down the deal and we both signed it.
I knew if I was successful in completely feminising Paul the landlord
would not say a thing as he was really tolerant and I had seen some
transvestites in his pub before and there had never been any problem.
It started badly. Sunday night was really dead and we only saw 4 girls
in pantyhose or stockings like he said. I was worried that I might just
have to do the striptease so before we went out on Monday night I decided
to take some action and I put on a miniskirt and fishnet pantyhose. I
resolved I would do this for the rest of the week as I needed to put the
pressure up as much as I could.
Paul was excited and on the look-out for girls in trousers as we went
into the pub. He wanted to get his score down. Just then a stunning
redhead came in wearing a skirt to die for, gorgeous seamed pretty polly
pantyhose and designer stilettos.
Then two girls came in together, one in a miniskirt and stockings (I
could see her garter belt) and the other in trousers.
Then no-one came in for another hour.
OK so we were on a total of five for both nights as the two girls had
cancelled each other out. It was not looking good and I did not mention
that I should be included in the score for tonight.
Then four girls in St Trinians outfits wearing fishnet stockings came to
my rescue. Hurrah for my sisters of St Trinians! I reached for my bag.
"Hey not so fast," said Paul. "That's only 9! You can't use me to reach
10!"
"That's ok Paul I wasn't but I am using you towards Wednesday's score."
"What do you mean?"
"Paul, you are so busy looking at other girls that you are missing the
one in front of you. What am I wearing?"
"Hey, that's cheating!" he said.
"No it's not! You yourself said you wanted to see me in a skirt and
tights. It's simply unfair of you Paul to accuse me of cheating. After
all isn't this deal about you getting me to dress up as French Maid? I
make an effort for you and you complain!"
"But you wore trousers yesterday didn't you? So that should be a minus
score!"
"Paul now that really isn't fair as I did not have the opportunity to
change."
Paul agreed and I pulled out the red pantyhose I had bought for him
wrapped up as a gift and with "Paul's first pantyhose" written on it. I
took a picture of him holding it up before he noticed what it said so he
thought he was just being given a present and smiled for the camera.
"Oh you can't be serious!" he said when he realised what I had done and
said "Can't we just forget it? You have your picture of me smiling
whilst holding them. I have never worn pantyhose before and do not
intend to start now. That's something that gays do."
"Paul, are you telling me you are not a man of your word? A real man
would not feel threatened by having just to wear one little item of
women's clothing. And I know you are hoping to watch someone do a
striptease across the road. Wouldn't it be terrible if people didn't
keep their words? In fact aren't gay men known more for breaking their
word than wearing women's clothing?"
I had no idea about this last comment at all but I needed to give him
something to prove by putting on pantyhose and this was just the right
sort of way to go about it. In fact as far as I know gay men are as good
at keeping their word as straight men.
"Ok!" he said petulantly. "How do I put them on?"
I told him how to roll them up in a ball and then ease them up his legs.
I had given him the smoothest pair I could find. One that when you
touched one part of the leg would make that whole part of the leg tingle.
He went off to the gents to put on his pantyhose and I thought about how
he had tried to wriggle out of it... When he came back I insisted that
he gave me the socks he had been wearing and reminded him he could only
take the pantyhose off on Tuesday night if we did not reach 20 girls by
then. As I told him this I rubbed his trouser leg and watched him
shudder as he said, "In your dreams!"
"The score is only 11 - including me!"
I knew he was feeling his legs tingling without needing to see the
reaction on his face.
Then Monday really became my lucky evening because the St Trinians girls
who had been steadily getting drunk had been joined by 10 of their
friends, who were all dressed in the same and it was still an hour and 30
minutes until closing time. Paul had now to wear pantyhose for two
consecutive evenings. What a difference a day makes!
"Looks like you could be in panties by Wednesday Paul!" I said. He
looked crestfallen.
"No sulking!" I said. "You wouldn't expect it of me whilst I dance that
striptease, so I expect you to try to enjoy this. How does it feel??
?Dangerous. I feel like someone might find out at any minute and expose
me. Then I wouldn?t be able to show my face in this pub again! It?s not
normal for men to enjoy wearing pantyhose.?
I noted that last point as I had not asked him if he was enjoying it and
his response betrayed that he was. I suspected he would enjoy this as he
was an adrenaline junkie and always liked to run risks.
Then I looked up and saw who had just walked in and I am sure my smile
just went from ear to ear. This week his ass was mine! Yes!
?Look Paul! We?re being invaded,? I said. The count had just gone from
21 to 50 as yet more St Trinians girls turned up and I started to wonder
if there was a real girls? school round the corner rather than a group of
women dressed as schoolgirls.
?Oh No!? he groaned and I really got the sense that he was starting
trying to avoid looking at girls in skirts now.
This meant that Paul was not just only going to be wearing his pantyhose
this week but I was not going to become a stripper. As I had only just
predicted he would be in panties on Wednesday night. I would insist on
him throwing out a pair of boxer shorts tomorrow and for each night of
the working week after today. He would then have to add a bra on
Thursday night and a corset on Friday.
Paul was shaking. ?I can?t believe it!? he said. I had never seen him
look so lost and vulnerable.
?You are going to have some time to get used to it!? I said. ?As it
looked like you were trying to renege on your word I think it only fair
that you give me a pair of your boxer shorts each time you have to wear
an item of female clothing other than pantyhose.?
He was so shell-shocked he simply agreed. I got him to sign the
addendum.
I had trouble sleeping that evening as I kept thinking of Paul going to
work fully dressed in drag and this image would not go out of my head and
got me rather excited.
Tuesday night at the pub was quiet and we only saw two girls, this time
not wearing St Trinians outfits but both wearing black tops and matching
miniskirts. The first was wearing fishnets and the second was wearing
nearly black pantyhose. I did not tell Paul that both girls were friends
of mine and I had asked them to come to the pub but to pretend not to
know me. I reminded Paul that he had missed two others ? him and me! So
we were now at four. It did not bother me that I had not won this
evening as he was going to be in a corset on Friday night in any event
and I had a few days before I needed to win again anyway. I decided I
would not try to cheat again though as I felt it was only fair I lost
this evening, having cheated.
Wednesday night worked out well though as firstly Paul was given his
panties, again like the pantyhose gift-wrapped, but this time marked
?Paul?s first panties.? I could not believe my eyes when he fell for the
same trick again and smiled for the camera. He was clearly not happy
when he realised what had just happened but he quickly tried to hide it
remembering what I had said the previous evening I think.
As the pub was empty and we could only be seen by people coming in the
front door and not the bar staff I told him to stand holding the panties
in front of his groin and to look pleased with them as I photographed him
holding them. Just as he was doing this three girls came in wearing
netball skirts and pantyhose and I explained to Paul that he had just
lost Saturday as I watched him quickly hide the panties hoping that the
girls had not seen him.
?Wait a second how do I lose on just three girls??
?Have you forgotten me again? And in addition to counting me in you have
to count yourself twice which means that with four from yesterday we now
have ten! I expect some gratitude for the money I am spending on your
wardrobe, Paula.?
?Now don?t start calling me Paula! But thank you for my panties and my
pantyhose Sara.?
?Haven?t you forgotten that you are now meant to be wearing them? And
that you owe me your male underwear?? I said slapping his ass as he
started to move past me.
Although there were no further girls that evening I was happy as we would
only need six girls on Thursday to give me Sunday too, as he would be
wearing his first bra tomorrow and he would therefore account for three
girls. Then on Friday we would only need five girls as he would be
adding his first corset and I needed to think what he would add on
Saturday to make him half of the score!
On Thursday night Paul said he felt sick and would not be able to make it
to the pub. There did not seem to be anything wrong with him the
previous day so I suspected he was just trying to get out of wearing the
bra I had specially bought for him that day so I said, ?Oh that?s ok
Paula I will go to the pub without you, after dropping off your bra which
I expect to see you wearing before I leave. I will let you know the
score when I get home but I might add a few girls if it is a slow
evening.? Suddenly Paul was healed! He got his just desserts too as the
evening was a disaster for him as there was a hen night and there were
twenty six beautiful girls all wearing beautiful miniskirts so I was
already in the clear for next week now. If I was to become stripper it
was unlikely to be happening as a result of this bet. I was starting to
enjoy watching girls in miniskirts a lot more than Paul was. Was I
becoming a lesbian?
I had to point out to Paul that he wouldn?t be out of pantyhose now
before next Tuesday at the earliest! I had Paul pose with the bra in the
same way as with the panties but out of sight of the other people in the
pub. I had sewn false breasts into the push-up bra I had bought him.
This was probably overkill as a push-up bra could have almost made him
look like he had breasts anyway. As usual he went off to the gents to
get changed.
I was delighted to see him come back as he was looking sheepish and there
was no mistaking that he was wearing a bra and had breasts. He asked me,
?Is it really obvious??
And I lied, ?Oh no Paul I would have no idea.?
And then surprised myself by not laughing out loud or even hinting at
what I was really thinking. I thought I would test the waters a bit as
he was still thinking of himself as Paul in panties, ?Aren?t you
forgetting to give me another pair of your boxer shorts? Now listen
Paula, tomorrow you get to wear your first corset so I expect you at my
house early so that we can get to the pub in plenty of time!?
He didn?t respond to me calling him Paula leading me to believe that now
he was wearing a bra his masculine identity was starting to be rather
threatened and he was becoming far less assertive and easily led. What I
had read about petticoat punishment was true.
I needed to think about what I would have him wear next as it was already
starting to get a bit obvious with the bra I had now got him into and we
were running out of underwear for him to wear.
So when Friday came Paul did as he was told and was at my house in plenty
of time. I explained, ?Paula this is your first corset and putting on a
corset is definitely as you put it about making an effort. You will feel
pain and I know that as you are a man, Paula...?
He interrupted me, the linking of his name with masculinity had awoken
something in him for a moment and he said almost questioningly, ?I think
you will find my birth certificate says I am called Paul.?
?You may find this particularly hard. This first time I am going to lace
you into it and this will help your body get used to wearing a corset but
it will get smelly after a day so as you are going to be wearing corsets
until at least next Tuesday I will have to buy you a few others.?
I didn?t realise what hard work it was lacing a man into a corset and by
the time I had finished he had an hourglass figure that I was almost
jealous of and we both needed a drink.
On the way to the pub I explained to him that he had better drink
something other than beer as we would never get the corset off him and I
suggested he have a ladies drink like a babycham. He agreed but I could
see he did not like it.
?What does it feel like to be a man in a corset?? I whispered in his ear.
He had a distant look on his face.
?A man?? he asked. ?Oh you are talking about what I think of my corset?
It?s surprisingly comfortable once you get over the pain of putting it on
and I guess it improves your posture as you are forced into a very
upright position and it really enhances my er..breasts.? He said.
Just then a group of five girls in skirts walked in and I said,
?Wednesday.?
Paul said ?Fine you don?t need to remind me I now count for four girls
and you are dressed the part too.?
Saturday came and I called Paul and said that it was now time for him to
walk the walk.
?Look I am not wearing stilettos if that?s what you have in mind? he
said.
?Oh yes you are.? I said ?But I will admit that there is no way you are
going to be able to hide what you are wearing on your feet. See you down
the pub.? I did not tell him it was a tranny night. We got to the pub
and the place was packed. There were around forty girls that I had not
seen before all wearing some form of dress or skirt from glamourous
evening gowns to miniskirts.
?That takes me through to next week at least doesn?t it?? asked Paul
dejectedly.
?Remember to enjoy yourself Paula,? I said. ?Would it make a difference
if I told you you are not the only man in a corset here tonight??
?No! Are you serious?? He said looking suddenly far happier.
?I have only noticed four real girls here, but they are all in skirts
which carries you through to next Thursday but I will agree not to count
other men in drag,? I said.
Paul started to relax and went over to one of the real girls and asked
how long she had been wearing drag for. I thought she would throw her
drink over him but she said
?Oh about a year now.?
Before saying to me, ?And you??
?About the same,? I replied knowing that it was her way of saying she
understood as this was not the first time she had been to a tranny night
and it was only normal that someone like Paul would struggle to tell the
trannies and the real girls apart.
Then she introduced Paul to her boyfriend Rosario who I had seen perform
on another evening and Rosario struck up an immediate rapport with Paul
who told Rosario that he had had a bet with me and that he was going to
have to wear stilettos for the first time tonight.
Rosario was really kind and told Paul that I had picked out a beautiful
pair for him before explaining to him how he would have to lean forward
more as he walked in stilettos and how they would hurt his calf muscles.
?That?s a bit of a sadistic heel,? Rosario told me out of Paul?s earshot.
?Yes I thought I would throw him in the deep end.? I smiled.
Paul told me later that his boss wanted him to take some time off work so
he would be able to get to my house early each night next week. I wanted
to ask Paul what this was about but Paul seemed a bit emotional about it
and did not want to talk about it. I forgot to ask him for a pair of his
boxer shorts but I knew that by next week he would be running out anyway.
When Paul came over the next day I gave him a bag of corsets that I had
bought for him during the day which he could do up himself. I said to
him that now he had all of the underwear he could wear under his male
clothes we were now starting on his outer appearance so as I had
introduced him to stilettos yesterday he would be wearing make-up from
now on.
He did not argue but sat their quietly lost in his dreams as I did as
good a job as I could of his make -up and did his hair, which was
fortunately quite long for a guy. Then I looked at him and thought he
would pass for a girl in men?s trousers, his jumper had to be thought of
as a girl?s jumper because of his bra even though I knew it was a men?s
jumper.
I had him give me another pair of his boxer shorts and we went off to the
pub. It was busier than the previous Sunday and with Paula (I could not
think of her as Paul anymore) wearing make-up, stilettos, a corset, a
bra, panties and pantyhose she now counted as six girls and I was the
seventh! This meant we only needed to see three girls and there were
about 25.
Paula was not looking so I was kind and pretended to have only seen 15
and said he was going to have to carry on until next Saturday.
On Monday night I put Paula in her first dress. She looked so hot the
landlord insisted on her kissing him and I wanted to sleep with her
We saw enough girls to take us through to the following week. By now I
had decided that I wanted to see Paula do what I had been meant to do. I
wanted to see her dressed as a French Maid and go to the seedy strip bar
and do a striptease. I had to set this up.
So during Tuesday lunchtime I went to the bar and was greeted by the
owner.
?Come to dance love? We pay good money,? he said with eyes which went
all over me at the same time as his dancers who were practising behind
me. I explained to him that I wanted Paula, who I said was a
crossdresser to perform here tonight. Did he have crossdressers perform
here?
?Sure? he said, his eyes not lifting from my breasts the whole time.
What did he take me for I am an educated woman and hold more
qualifications than he has dancers?
I explained that Paula and I would both come dressed as French Maids and
explained my name was Sara and her name was Paula. I would pay him ?100
now to pick Paula when I asked him which one of us he would like to see
perform.
?Deal,? he said ?But crossdressers do not remove their bra and panties.
It?s a rule we have here.?
When Paula came over that evening I took his last pair of boxer shorts
from him and told him I was bored of eyeing up other women and wanted
instead for tonight to just be about each other. I wanted to do a new
bet.
?Tonight we will both wear corsets and dress as French Maids. We will
then go to the seedy bar and invite the owner to pick one of us to
perform and the other will get to film her.?
?Deal? Paula said and I knew she thought I looked sexier than her and
that she did not know how hot a man dressed as a French Maid could look.
Both of our outfits were classic black and white maids costumes which had
short sleeves but we both wore white cuffs round our wrists. We both
wore garter-belts which you could see under the dresses as the dresses
were too short to cover the tops of our stockings and our black lace
panties were visible if we bent over.
So holding each other?s hands we went to the seedy bar and we asked to
speak with the owner and explained our bet. The owner said ?Fine, but
you need to both agree to do as I tell you and I want to see the video
afterwards to make sure you are not filming any of my other girls or my
customers.
Then he did something unexpected and said, ?Gentlemen, tonight we have
two French Maids. I am to pick one whilst the other films her. So I
pick Paula!?
What did he mean we have two French Maids? Oh well never mind. The
place erupted and Paula was incredible and the customers stuffed lots of
notes in her bra and panties which she was not to take off. She was
given a dressing gown and led off the stage.
?Now at no extra expense we have our camera lady maid Sara!?
?What?? I thought. ?This wasn?t part of the deal.?
I tried to indicate this to the owner.
?Come on Sara. Don?t disappoint my audience.?
So, despite winning almost every night I was now to become a stripper. I
took off my maid?s costume apart from the cuffs as seductively as I could
and the crowd seemed to really enjoy it. I started to get into the swing
of it as I took off my corset but then I realised that having slipped off
my fishnets that I was going to have to take off my bra too as I was not
a crossdresser. I went over to collect my tips and my panties almost
fell down with all the money stuffed in them.
The owner came over and squeezed my ass and gave me a dressing gown and
showed me back stage.
?Paula filmed you as well Sara. Care to see yourself?? he asked. ?Look
there is no way I can let you two girls go this evening so I have taken
your dresses and sent them to a dry cleaners. They?ll have them back by
tomorrow night. I would like you girls to perform again tomorrow and to
sign a contract to do so for the rest of the week. Let me know if you
are happy to do so in the morning. I will make it worth your while. I
am afraid we are out of food tonight but we have these tablets that the
military used to use which act like a whole meal.?
Part of me said ?Don?t be stupid. They are drugs and will mess with your
head.? But I was hungry. In the morning I would have signed anything
anyone had put in front of me as I was out of my head.
But the contract was limited to the end of the fortnight and as we saw no
girls in skirts as we were the only ones wearing that much clothing in
the place I said that Paul was now free of the bet.
I had developed a taste for performing at the seedy bar and I am now in
negotiations over a new contract.
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