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What If...? free porn video
What If...?: By DebWeb
After reading several stories about discreetly trying on a school uniform
my early childhood memories were awoken. I was raised in a children's
home from the age of seven. It was a small institution comprising of both
boys and girls. There were four bedrooms in all. Two for the boys and two
for the girls. I recall the time when I was ten years old and I sneaked
into one of the girl's bedrooms and stole a dress I had so admired from
her closet. As clever as I thought I was in my hiding place for my booty
it was discovered by matron. Rather than confronting me she decided on
another way to punish me. I woke up on a normal Monday school morning to
wash and put on my neatly folded school clothes as usual. Only this
Monday morning was rather unusual. As I dressed I reached for my school
shirt only to feel a softer material than was the norm. Without
hesitation I donned this wonderful garment and savoured the soft feeling
as it brushed against my skin. Have you figured it out? It was not a
shirt but a lovely school blouse! I wore it with no protest to matron's
consternation. The next morning I woke up to find a pair of girls
burgundy knee high socks which I pulled over my feet and up to my knees
in silent delight. So there I was appearing at the breakfast table in my
school blouse and girls school socks discreetly hidden under my jumper
and trousers respectively. As the spiteful matron looked on studiously I
never uttered a word of protest. I sat down at the table as normal. This
ended the whole venture as I was returned to my normal shirt and socks
the following school morning. This was a true experience in my childhood
but I have often fantasised what if matron had decided to take it
further? Where might it have ended...? The following tale is fictional but
sprinkled with a few truths.
Rosie was an ugly girl with no becoming features. Even her hair was
unattractively short and barely covering her ears. The only thing I
envied her for were her skirts and dresses that she wore. Oh and the fact
that she was a girl and I wasn't.
We lived in the same house but we were not related in any way. This was a
children's home where many boys and girls came and went depending on
their circumstances. Some of us were lifers. By that I mean we expected
to stay there until we reached the official adult age of eighteen.
Anyway, one day my urges seemed to get the better of me and I sneaked in
to Rosie's bedroom and stole a lovely pale yellow dress with a flower
printed pattern adorning it. Being the clever rogue I thought I was I hid
it in a little used storage cupboard in my bedroom. I could not wait for
a free opportunity to wear it but alas it was not to be. When I returned
to fetch it the following morning it was gone! I was mortified as I knew
one of the daily cleaners must have found it and most probably handed it
to matron. My dark secret was out! I felt like running away there and
then but where would I go? I only knew this small provincial village. To
depart from it would feel like falling off the edge of the world. There
was nothing for it but to face this calamity head on and bluff it out.
With carefully planned excuses in my head I went downstairs to face the
storm. To my surprise nothing was said. No confrontation but I did think
I was getting strange looks from Rosie. I put it down to a degree of
paranoia on my part. I was just so relieved that my misdeed had not
become an issue.
Monday morning I arose and went through my usual hygiene cleansing. I
returned to my bedroom and began to dress into my school uniform. Briefs,
socks, vest, shirt... What was this? It did not feel like my normal pale
blue shirt. Yes it was the same colour but so much softer to the touch
than I expected. As I held it up before me I noticed it was shaped
differently. No back tail but instead it was a straight line all around
the bottom. I was so intrigued by the shape and softness of the silky
material I could hardly wait to try it on. As I savoured the silky
coldness warming up against my skin I encountered more strangeness. The
buttons were on the left and so much smaller than I was used too! With a
little clumsiness I eventually buttoned up my blouse. Yes I knew it for
what it was but I was quite happy to plead ignorance should anyone
question me. I finished dressing and proceeded downstairs for breakfast
without a care.
Matron and Rosie seemed to look at me intently but I carried on as if it
was just another school day and nothing out of the ordinary had happened.
Well nothing unusual did happen apart from enjoying the soft sensation of
that silky material rubbing against my skin. It was a distraction from my
lessons but I got by.
I'm back home again and reluctantly changing out of my uniform back into
my drab casual clothes.
Tuesday morning and to my delight the blouse is neatly folded amidst my
school uniform. What's this? A pair of girls knee high burgundy socks!
Well needless to say I dressed in my hybrid school uniform quite happily.
Tuesday followed on in a similar vein as Monday so not much more to say
there.
Wednesday brought some new apparel although it was a bit confusing. It
was sort of like the y-front briefs that I was used to but without the
split at the front. They were more elastic and stretchy than my briefs
but they hugged my penis and prevented it from swinging around. All in
all they were quite comfortable so I had no qualms in wearing them.
Matron and Rosie seemed a bit perturbed as I attended to my breakfast
without a care in the world. School went as normal as enjoyed all these
new soft materials rubbing against my skin.
Well now it's Thursday and I have received a new garment amongst my
school attire. It is a new pair of trousers but they feel softer and
stretchier than my normal ones. I am surprised at how light they are.
It's as if they are made of gossamer. Oh well not to worry they are only
a pair of trousers after all.
This feels strange. They seem to be hugging my hips as they stretch. The
bulge in my crotch is a bit embarrassing. I know, I will tug my penis
back and tuck it between my legs. That way no one will notice my strange
trousers. I am a bit concerned how they are tapering out at the bottom
though. I must act as if everything is normal because I don't want to
give Rosie and matron any sign that I am unhappy.
I got some strange looks at school today. It was mostly from all the
girls. Every time I passed them they would coo "Hi Dave" and burst into a
fit of giggles. The boys seemed to give me a wide berth.
It's Friday morning and I look upon my school uniform in trepidation. I
was worried as to what new garment may be included. To my relief there
was no new outer clothing which might add to my embarrassment. There was
a lavender coloured under vest replacing my plain white vest. It had a
lace trim around all the edges. I consoled myself in the fact that such
girly underwear would be hidden under my blouse.
School was strange today. All the girls were very friendly and chatty
towards me while all the boys ignored me. I did not know where to put
myself as the girls coerced me to sit with them in their favourite spot
in the playground and listen to their never ending chatter.
I'm so glad school is over for the weekend as I am so confused. It
somehow feels like a reprieve for a condemned man or boy. Well whichever
way you want to look at it. In actual fact I am beginning to feel more
like one of the girls. Ensconced in my soft school uniform and feeling
all those delicate sensations it makes me feel more fragile. Added to
that the girls are now the only ones who welcome me into their company?
The only thing that seems to be separating me from them is now the school
skirt. No! Perish the thought right here and now!
The weekend passed all too quickly and it's Monday school morning again.
I look at my neatly folded school uniform somewhat warily. To my relief
it is the same apparel that I wore on the previous Friday. I go through
my usual routine and sit at the breakfast table without a complaint. I
was actually feeling quite smug as I realized these females in the home
could not perturb me.
After finishing my breakfast matron handed me my shoes. They were not my
shoes! They had a high heel at least an inch! And they looked exposed on
the top. The only thing to prevent from stepping out of them was a narrow
strap which required to be buckled to the side of the shoe!
With a little hesitation I decided that matron would not beat me in a war
of wills! So I calmly took them from her and strapped them on my feet.
Well if I'm honest my fingers were trembling just a bit. I had defied
matron and Rosie though and put them on without protest. Another point
for me!
As I walked to school I found the heels of the shoes a bit awkward to
walk on. I did discover that if I took smaller strides then it was easier
to maintain my balance. Feeling I had one up-manship against matron I
confidently walked through the school gates. Why were all the boys' eyes
drawn to my ass? To my relief the girls all crowded around me in a
protective formation and ushered me into the girls 'toilets? Now I was
really confused!
"This is where we sit to pee," Margo announced as she pointed to one of
the toilet bowls within a cubicle. "We always keep the toilet seat down."
I nodded my head in agreement but somewhat confused by this whole
situation. "We wipe from the back to the front when we dry ourselves."
Margo gave me a hard stare as if to see that I had her full attention. I
nodded my head vacantly as I pretended to understand what she was saying.
Why on earth was I in the girls' toilets anyway?
Margo grabbed my arm and pulled me out of the girls' toilet to my relief.
Only problem was she kept pulling and guiding me to another part of the
school building. To my stunned amazement she guided me into the girls
changing room. Her younger sister Sally was sitting on the bench along
with other girls from my class. Selena, Jackie, Fiona and all the rest!
They all had sort of secretive smiles on their face. Sorry but that is
the best way I can explain it. As if they were privy to information that
I wasn't.
Margo pointed to locker #8 and declared, "That one is empty. The lock
code is 8300." She looked at me to see if I was absorbing all this
information. I looked back at her confusion wondering why this was
relevant to me.
She took me by the arm and pulled me out of the girls changing room and
left me in the empty corridor while she re-entered the girls' locker
room. I must admit that I felt a little lost now with no one to guide me.
Well let me tell you! That was one weird Monday I am so glad it's over.
Tuesday again and I'm a bit worried about going to school after
yesterday's experience. Oh well, onwards and upwards.
I am sitting quietly at my school desk and minding my own business but
there is a problem. You see the layout of all the desks are connected in
a rectangular formation so we are facing our various classmates. Well the
problem is that I am facing all girls opposite me and they keep kicking
my shins under the table. It is not painful or anything. But every time
they kick me I cannot help but to divert my eyes under the table to see
which one kicked me. Well erm... they keep opening their legs and making
sure I can see up their skirt and they are showing off the colour of
their panties! I'm not sure what to make of it. It does not help the
matter as I think I am wearing the same panties as Margo is displaying to
me.
I'm so glad that day is over as it was very trying for me to say the
least. The boys avoid me like the plague and the girls have been acting
very strangely and sort of secretively towards me.
Its Wednesday morning as I reluctantly rise in worriment of what the
school day will bring. I have stopped living in denial now as I don my
school uniform. Every item I am putting on is really girls' clothing. The
only thing that differentiates me from the girls is my female trousers.
It's funny in a bizarre sort of way. Skirts are compulsory for girls at
our school and yet here am I dressing in a girls clothes completed with
girls trousers.
I go down to breakfast and eat it in contemplative silence. Where is my
life leading to I wonder. All because I stole that confounded dress! I
strap on my Mary Jane's and look around for my schoolbag which is not to
be found in its usual place. Matron thrusts my bag in front of my face.
Only it is not my schoolbag. It is a pink rucksack with a big picture of
Hannah Montana displayed on the front. I cannot help but give a wry grin
as think we have something in common. We both have dual identities after
all. Only hers are two girl identities and mine seem to be boy/girl
identities.
I go to school and hope I can endure it quietly. It was not to be. Today
turned out to be a life defining day if I'm honest. It happened at first
break time in the morning. I think it was some sort of initiation.
I was walking along the playground in solitary mode and feeling very
lonely. Suddenly I was attacked by all the girls in my class! They did
not hurt me but they did pull me in one direction. They pulled me into
the girls' toilets! I felt the zip on the back of my trousers being
unzipped? Amid much excitement and screaming they pulled my trousers off!
Margo withdrew her hidden hand from behind her back and waved the pleated
grey school skirt in front of me. "It's so unfair that you get to wear
trousers while the rest of us girls have to wear skirts." She admonished.
And with that the rest of the girls lifted up my lower body as Margo slid
that school skirt up legs and wrapped the elasticated waistband around my
well obviously waist. All the while the rest of the girls were chanting
"One of us, one of us, one of us."
So there I stood in total completion adorning the girl's school uniform.
The air flowed around my naked legs and sneaked above my hemline. It was
a strange sensation but a very pleasant one as the skirt swayed around
the hemline and tickled my legs. Margo took me gently by the hand and led
me to our class room. She introduced me to the class as Davina the new
girl and then we both went and sat on the girl's side of the classroom.
Optional Prologue
It was the summer break from school and a very scary yet frightening time
for me. I was sandwiched in the back seat between Margo and her younger
sister Sally. I was on my way to the hospital for that final and ultimate
clipping of my tail. As Margo pressed the palm of my hand in between her
legs to remind me of the empty void I would soon experience for myself
Sally was tugging away on my soon to be extinct appendage. One more
erection before it was gone for ever.
Gert
- 07.05.2022
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