Date: Mon, 9 May 2016 11:31:15 +0000 (UTC)
From: craigbrownmagic@yahoo.com
Subject: Caught Out Unawares

Caught Out Unawares.  By Pepperpuppy
craigbrown magic@yahoo.com

If you aren't old enough to be looking at this web site story, please nick
off!

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I preferred not to know many people at school, to scared that someone might
find out my hidden secret because for an immature sixteen year old Aussie
boy, any of my school mates finding out would probably cause me to be
bashed up as well as being teased and called a faggot, a poofter or a bum
chum. Infact I still couldn't explain why if someone were to ask me, but
for some reason I really liked the feeling of wearing women's underwear and
always liked to wear them under my male clothing.

The back of my wardrobe had a shoe box in it filled with girls and women's
panties in cotton and polyester fabrics in all sorts of colours and styles
although most of them were high cut style although I did have a few G
Strings and bikini styles I wore as well, just not as often.

I'd had this weakness since I was a young boy back in kindergarten where
boys and girls often sat crossed legged on mats on the floor and it was
more or less accepted that five year old girls could sit cross legged with
their undies showing under their school skirts or uniforms without having
to care about modesty or things like that and that almost every boy always
took the chance to look at what colour undies a girl had on but never got
any sort of sexual thrill out of it.

I also had two older sisters, one two years older and two years infront of
me at high school and the other three years older than me and whenever mum
went through their undies drawers to find what needed replacing and putting
the better pairs in the clothing donations bag usually saw me sneaking them
out afterwards and so that's how I started my collection and also wearing
them.

Over time I would also occasionally steal a pair of panties off the
clotheslines on either side of our house which to the best of my young
knowledge also went unnoticed. When I got a paper round job part of my
earnings allowed me to buy new pairs of panties although it also meant
catching the train to take me a few stations further where I could shop in
relative anonymity and leisure before smuggling them inside my room when I
got home. On exceptionally rare occasions I got to sneak one of mum`s old
pairs out of the donations bag which I prized for their slippery feel if
not for the occasional stain, or sometime it was one of her slips instead
which were of a similar type of fabric.

Nowadays, although I usually wore only cotton panties around under my boy's
clothes, I'd occasionally spoiling myself and wear a pair of slippery
smooth shiny satin feeling panties which felt wonderful sliding against my
testicles and causing my little penis to stiffen out like a rock pillar
inside my trousers often forcing me to have to carefully and without anyone
seeing me, put my hands inside my trousers and panties and move my penis
around to one side until it was no longer sticking straight out in front of
my trousers.

I always made sure when I had gym on the Tuesdays and on sports afternoons
that I only wore men's tightie whities and was careful not to look at the
other boys or their cocks which were always on display in the dressing
rooms. I always showered after gym or on sports afternoons and although
never shy was also never boisterous drying off or joining in the horse play
of teenage boys, usually overflowing testosterone and besides which damp
towels could be especially painful when flicked against naked bottoms.

I didn't ever think of myself as gay even though I liked to wear women's
underwear under my clothes because I always played sport in various high
school teams and often talked to the girls at school as well as the boys,
although I didn't feel any sort of strong attraction to either sex. I did
however enjoy listening to the girls discuss fashions particularly if it
was one of the girls at our school who may or may not have committed some
cardinal fashion sin which they were talking about. If I knew the girl they
were talking about I tried to discreetly look at what they were talking
about during the rest of the day, and if they were talking about her
period, I tried even harder to get to talk to her face to face to see if I
could notice what the girls could obviously see so I could know what to
look for in the future.

Goodness knows it seemed like each girl in my year at school seemed to have
a different "tell" sign signifying when Dr White was seeing her and it was
quite difficult not to be caught out looking for those tell signs if and
when you got to talk with any of them and still appear interested in what
they were telling you while you were trying to determine if they were "on"
(a girl's term I overheard one of them say one time when she was having her
period) or not.

Anyway no one seemed to know about me at school and as far as I was
concerned the "no harm, no foul" rule applied because I certainly wasn't
hurting anyone wearing women's panties.  That was until one day in dressing
shed toilets during lunch break, when my flimsily locked cubical door
crashed open by a pair of six formers fighting while I had my pants down
around my ankles and was pulling up a pair of pale pink panties in full
view of both of their astonished faces which were now down near the
concrete toilet floor and looking up at me frantically trying to now pull
my school trousers up and cover myself.

They quickly stopped scuffling and the taller of the two told his mate Ian
to dash outside and keep a look out and stop anyone walking in, then turned
to me and shaking his head said "uh, uh," and quickly undid my trousers and
pulled them back down before looking back up at me and grinning broadly.

"What's you name sweet thing" he asked me and I told him it was Greg to
which he said his name was Ryan and he was wearing a prefect's pocket on
his blazer, but from now he told me on I was to call him Sir and he'd call
me Gail. He told me to stand there and not move a muscle while he called
out to his mate Ian to come in and once inside told him my name was Gail
before taking up the lookout post outside the room while Ian came in and
looked at me.

Ian (also a prefect) looked at me and seemed to sigh before telling me to
slowly turn around once and after I'd done it he told me I had to be in
this cubical after school today dressed in only my panties so that he and
Ryan could decide how they wanted to use me, before reaching over and
carefully fondling my testicles and ordering me to get dressed and
reminding me again to make sure I was here after school or him and Ryan
would come looking for me for missing prefect's detention.

I spent the last three periods nervously waiting to find out my fate, when
the final bell rang. I resignedly made my way slowly to the dressing rooms
toilet block and got undressed down to my panties and waited
anxiously. Soon enough Ryan and Ian came in and locking the door behind
them ordered me to come out of the cubical. When I timidly did they both
voiced their approval of how I looked. Ryan then came up to me and gently
made me turn around several times while he backed away to look at me again.

"God she looks hot" Ian said to Ryan before telling me I was so thin I
actually had a waist. He then asked me to turn the other way and bend over,
which I did and described my bottom as a priest's wet dream and asking me
to walk away and back several times, all the while staring at my walking
while holding my arms up in such a way as to try and cover my chest and the
front of my panties at the same time.

I was then told to stop and kneel down on the ground as both boys came over
undoing their fly zips and taking out their penises before Ryan told me to
suck his cock and reinforced it by grabbing the back of my head roughly and
forcing and mashing my face into his stiff dick which was quickly covered
by his precum before he hit me hard on the back of the head and said open
up. Being someone who was no more than 5' 6" and weighing around 110 kilos
and having him towering over me I thought that discretion was the best
course of action so I opened my mouth to have it quickly stuffed with his
hard dick which he was trying to force further inside my mouth.

While Ryan was doing this Ian had gone round behind me and was firmly
pressing down on my shoulders while Ryan's hands held me head tightly. I
felt I was choking for air while Ryan told me to breathe through my nose
and before I knew it I was swallowing his salty cum and gagging on his
stiff cock still in my mouth. He suddenly pulled my mouth off and left me
gasping for breath before Ian swapped places with him again but mercifully
came very quickly leaving me to again swallow salty male cum. While I was
trying to recover Ian was on his mobile talking to someone.

"I've found us the most gorgeous bit of chicken flesh for the boys to use
when the girls are on their periods" he advised someone, before adding "be
there in five minutes" and hanging up. I was ordered to get dressed and
follow them before they lead me to the prefect's hut half way down the
school grounds and told me to enter as they followed me in.

Inside were several female and male prefects lounging around seated and
talking, when Ryan announced they should meet their new "chicken" and told
me to strip. I actually knew one of the female prefects who was good
friends with my sister and saw that she recognised me as well although not
saying so. Ninety seconds later I was standing in my panties blushing beet
red while various comments were being passed about me. Ryan suggested the
two female prefects take me into the other room and explain my new duties
to me so the other girl and Suzy took me into the next room and closed the
door gently asking me to sit down once we were in there with the door
closed to the main room where four male prefects were.

"You poor thing" Suzy said to me kindly "You've got no idea what it's going
to be like for you from now on till you leave sixth form, but trust me when
I tell you that they'll be some rules being laid down to protect you from
today onwards" she assured me with a smile.

Her friend was now on her second phone call since we'd entered the room and
I heard her say "get back here straight away, Ruin and Alice have found
themselves a chicken so that means we won't have to worry anymore about
putting out if we don't want to" and then a girls muffled voice before she
excitedly said "he's wearing panties would you believe it and it looks like
the two of them have already had first use of him the pigs," she told her
friend before saying to her to phone up Denny, Marie and Jules and get them
here ASAP so we can lay out the ground rules to those pigs out there and
their mates so she (did she mean me?) doesn't end up like a bitch on heat
for every guy in seniors.

Suzy had meanwhile gone over and looked out the viewing pane glass in the
door before coming back over and saying to her friend "There all on the
phones telling everyone about it" before sitting down next to me and
telling me "Greg" and I had to tell her that Ryan said I was Gail from now
on which made her sigh before she carried on. "Look I know your sister
really well and although I promise you none of the female prefects will
tell her about you, she's going to find out somehow about it so it might be
best if you talked with her when they let you go home later on, but believe
me short of telling the principal she won't be able to help you out" before
gently hugging me and softly saying sorry to me in my ear.

Suzy then started to explain to me what I'd be expected to do in the future
most afternoons adding that she herself had just started her period (and
taking my hand gently touched between her now open legs which had a padded
feeling in the panties she had on) explained to me that Dave outside (which
ever prefect he was) had been expecting some sex this afternoon and she'd
already told him she was bleeding so he could go play with himself or lump
it.

Basically I'd be sex for every male prefect that needed relief because
sadly for me the rest of her prefect friends preferred not to have sex as
often as their boyfriends wanted and most of them didn't like oral sex so I
was going to be on call sex doll for them to get their rocks off on. She
also assured me that I wouldn't be able to get out of it unless I was
willing to be exposed for wearing girl's knickers but that the female
prefects would lay out the ground rules for how I was to be treated and was
to be protected from any future bullying and that those rules would be
passed on to the following years prefects who would be told beforehand
about me.

Just then two girls opened the door and walked in closing it behind them. I
recognised Julie at the same time she recognised me and simply said "oh
shit. Not him for Christ's sake" in a regretful voice while her friend
asked if she knew me and on finding out who my sister was simply shrugged
her shoulders and said I was wearing panties so I probably wanted whatever
the guys had instore for me, which told me how she felt about the matter.

In the end I was finally bought back out into the main room where there was
now eight prefects looking at my near naked ness except for the panties I
was wearing before Suzy said she was acting on behalf of the female
prefects and proceeded to lay out the ground rules for using me any time on
the school grounds for the rest of the year.

The rules session got a bit heated at times with both sides having to give
a little in the way of usage rules but finally everyone was agreed and by
tomorrow afternoon they'd all have emails of the rules as well as a typed
sheet on the wall in the back room, wherever the hell that was. The rules
were simple and had to be obeyed by all parties concerned and were as
follows.

1. Any sex was to start from the following afternoon 25/6/20XX.  2. I was
never to refuse a male prefect who wanted sex with me.  3. They may have
oral or anal sex with me on demand.  4. Sex can only ever be after school
and in this shed.  5. Any anal sex requires a mandatory condom being worn.
6. I was never to be physically hurt, or bruised or marked unless I allowed
it.  7. I was to be protected at all times from any bullying from other
students.  8. Any prefect who had an STD was forbidden from having sex with
me.  9. The female prefects would help me with clothes and makeup whenever
requested to.  10. Every month I was to be given two days off from sex.
11. No one was allowed to tell my sister about me or else I was no longer
available.  (This last rule was important although someone had already
blabbed I found out)

After everyone except me was agreed on the rules I was allowed to get
dressed and go home, which Suzy drove me to although not stopping to get
out of the car. That evening my sister and I sat down and talked about
things. At first she seemed incredulous that I could be so foolish, but
before I had explained everything and had checked my emails to find the set
of rules had been posted began to gain her sympathy. After I came home the
next day at 5.30 instead of my normal 3.30 she was worried about me and
proved she had a gentle tender side to her which I had long forgotten
about.

She began to teach my about sex hygiene and also had me in embarrassing
positions as she inspected my anus once a week while always reminding me
never to have sex with someone who had a sore on or near their mouth. She
also made sure of this by going into the prefects cabin on Mondays
lunchtime and looking at each male prefects face. The female prefects
checked out the dicks to make sure I was as free from sexual harm as
possible.

By the end of the first full week as the male prefect's sex toy I'd been
well and truly used orally and anally and was no longer worried. I also
quite often was allowed to parade in lingerie and comfortably talk with
everyone and quickly got over my embarrassment especially with the female
prefects. Of course five of the female prefects had boyfriends at school
who weren't prefects so those five boys also got the run of the cabin.

The "back room" became my personal room with a double bed and clean linen
provided by the girls for me every Monday. I was also allowed the freedom
of the cabin during school hours provided I was careful and not obvious
about it.

By the end of the year I was actually enjoying most school afternoons and
often did multiple sex partners and didn't think anything of giving oral
sex infront of the female prefects when they were on their periods although
often I did it anyway even when I already knew otherwise. Even though it
was all meant to be secret, word leaked out usually through stupidity and I
actually had three male teachers I was often servicing as well after
school.

The end of the year saw me receiving lovely lingerie from every prefect
along with assorted dildos and my anus was also now obviously open to
anyone who looked at me when I was naked. The following year saw a smooth
hand over to the new prefects as it did in my final year.

By the time I graduated I was the perfect male slut, experienced, willing
and always happy to go the extra "inch" when required. I was now openly gay
and often wore girl's slacks or blouses to school without being disciplined
for a uniform infraction. I was also not able to fart silently either.