Voyeurs Part 2
Things were quiet for the few months to follow. All of the boys remembered
the horrible awkward period following their humiliation - as they removed
the clothes and makeup, hardly looking at each other, their minds flooded
with the thought that those pictures might get out. But come the next
Monday morning, nothing had happened yet and it fortunately looked like
they were in the clear. The girls, who they supposed had the power to ruin
them, chose not to, which was a massive relief. The weeks following were
notably less filled with shenanigans than the previous couple, and far less
than normal on the overall. Things were, oddly, sort of calm, and while
they could not ever forget what happened that night, they did forget
Margaret's final threat.
James and Margaret never spoke much usually, but now you wouldn't even know
they were brother and sister. James was filled with emotions that he could
and couldn't explain, that seemed to complement and yet contradict each
other. He was angry, but also embarrassed, and sad, and nervous, and
entertained by his friends' makeovers while knowing his own was so much
worse. Most of all, he wanted to forget it had ever happened, and to his
luck, apparently everyone else was perfectly comfortable pretending that
was the case. None of Dylan, Cam, or Bobby would dare bring it up,
especially in public. They had a silent accord that this would be a part of
the past, and mostly, they would leave those girls alone with their antics
for fear of facing something like that again.
The girls, on the other hand, were perfectly comfortable discussing their
work, at least among themselves. True to their word they retained, but
didn't share the incriminating pictures. The way the boys had squirmed,
helpless while their makeup was being applied was almost good enough by
itself, but knowing that they'd have to dress up too really put them over
the edge in that vanity chair. The clothes themselves weren't even the
worst part (though certainly a bad one) but the anticipation was killer!
Plus, they had all come out looking so much better than even the girls
expected! Courtney's sense of style was top notch in guiding their outfits,
Margaret was a natural with hair and all of them were very well trained
with makeup, but still, no one thought they could look just so girly! Cam
and Bobby could have passed for real girls in the right lighting, and Dylan
and James weren't too far off after their relatively heavy makeup.
Just imagine, reminisced Margaret, what they could do over the course of a
whole Halloween day. Those boys had only gotten a taste of their
punishment. Their behavior deserved something more, and she had already
planned just how they would get it.
Halloween fell on a Saturday that year, and as October began the school and
all of the local teens were abuzz with talk of parties, costumes, you name
it! Spooky season was a treasured time, and James, Bobby, Cam and Dylan
were as excited as anyone, thinking about how they might dress up and
whether they might actually get invited to a party this year, rather than
sitting around one of their houses playing video games and eating candy
like the last year. Ever since they got too old to really trick or treat,
there wasn't much to do for a less-than-popular guy their age.
It was 3:00 in the afternoon on October 16th, a Friday, when they got the
texts from a number none of them recognized. The boys were together,
gathered by their lockers ready to head home, when each of them was sent
more than a couple pictures of themselves and the others at the vanities,
in makeup, and of course in their full outfits. To make it worse, the way
the shots were timed and posed, you could clearly see who they were. Worse
yet, they also almost looked like they were enjoying it! The girls had
found quick flashes of broken smiles and laughs at each other, as they got
their nails and hair done, during the reveals, and afterward, that made it
seem like the boys were willing participants. James even saw one picture of
himself in the other room, in just pink panties and a bra! Margaret had
used HER DAMN CAMERA to spy on him while he changed, the same crime he was
being punished for! Like clockwork they closed their phones in a flash and
looked at each other, checking to see if anyone was around. This was the
last thing they ever wanted to happen, especially now.
Their phones buzzed one more time. They all carefully checked the messages,
which all read the same thing:
"Hey girls! Halloween is coming up and I hope you haven't forgotten our
little deal! Meet us at 5 by the library and we can talk!"
"What do we do?" asked Cam. "I can't let those pictures get out, my dad
will kill me!"
"You're telling me!" grumbled Bobby. "We're fucked."
"Guys, guys, chill," answered James. "They can't do anything, it will be
alright, just relax."
"RELAX!?" Dylan exclaimed. "You're the reason we're in this mess." I don't
know where you guys are, but I'm going to fucking library, if they release
your pics that's not on me.
"Well actually, Dylan," said James. "We have your pics too, not just the
girls. If I go down, you do too. No question."
"Fuck," whispered Bobby.
James continued. "We'll go to the library, we'll see what they want. We can
be reasonable, maybe they just want to see if we comply."
No one really wanted to go, but no one really had any better ideas either.
They decided to stay at Dylan's house for about an hour before heading into
town to meet their blackmailer. As they walked up to the storefront, it was
both a terror and a relief to see Margaret, Courtney, Maddie, and Becca,
four of their prior assailants. Rachel and Emily, apparently, weren't
around.
"Hello boys!" Maddie spoke first. "Glad you decided to join us"
"Oh, we are too!" James answered sarcastically. "And to what do we owe you
lovely ladies the pleasure?" He looked at Courtney while he said it;
Margaret rolled her eyes at her little brother.
"I think you might have a good idea why we're here James!" Margaret
replied. "And let's be super clear - you are free to leave at any time you
want! We aren't forcing you do to anything, I just can't guarantee what
happens to those beautiful pictures if you don't listen to us."
"You wouldn't." James answered.
"Try me," she rebutted.
"What is it? You just want to make fun of us?" chimed in Cam, his voice
shaking and his face flushed. Knowing Cam, he might have been close to
tears.
"Simple, boys," Becca spoke this time. "We want one more thing from you,
and that's to take our favorite little brother and his friends trick-or
treating on Halloween! It's going to be so much fun!"
On the surface, there's nothing any of those boys would have rather done
than spend Halloween with four of the most beautiful girls in the school,
two years their elders (except for James, who would be there with his
sister - yuck). They knew, however, there was something more insidious
going on.
"We had so much fun last time with you fellas that we just couldn't pass up
a chance to hang out again! How great!" said Becca. "We're gonna have a
costume contest! Each of us is going to help one of you with your costume
and whoever has the best one will win!"
Margaret interrupted. "Here's the deal guys. You do what we say up until
and on Halloween, and we'll delete the pictures, swear on everything I
have. You can also refuse, but don't get mad when everyone learns about the
little pansy sophomore boys who tried spying on the hottest girls in
school. That will go over greaaattt."
The funny part was, they only intended to punish the boys who failed to
comply. Unfortunately, the boys' pride rested on mutually assured
destruction, and so none of them could allow any of the others to leave -
they either failed together or succeeded together, and by the sound of it,
they wouldn't accept failure if it meant those pictures going live online.
"But Margs, how are we gonna pick teams?" Becca asked and playfully pouted.
"We could let the boys pick?" said Maddie. Cam's ears perked up at that
suggestion.
Now if you're a 15 year old boy, and you're going to have to let a 17 year
old girl pick your Halloween costume, and by virtue of experience you
expect it to be embarrassing, do you pick your crush, or anyone but your
crush? On the one hand, you probably get to spend time alone with the girl
of your dreams doting on you - incredible. On the other hand, you're
watching your pride melt away, and possibly your masculinity too, at the
hands of the girl you most want to be with, who sees you as a girly doll
just as much or more than a man - highly not incredible. The calculus for
Cam was simple - Maddie was going to see him dressed up whether she was
doing it, or whether she just saw him afterward. That made it obvious - and
he very quickly interjected.
"Yeah we can pick that's fine," he said so quickly that the words seemed to
fall out of his mouth.
"Cam we all know you want Maddie, right?" said Courtney.
"Uhhh..."
Margaret turned to Maddie, who nodded slightly. "Yeah that's fine, Cam and
Maddie for the first team," she said.
Becca spoke next. "Before any of them pick can I take Dylan? I think he
liked how I did his makeup last time."
Dylan blushed. Truth is, none of the boys knew which girls were doing what
at any time, but if that's what got him on a team with Becca then so be it.
His nod through blushing cheeks signaled his assent and team 2 was formed.
That left Margaret and Courtney with either James or Bobby. Margaret
recognized what was happening (she knew all of the boys and their crushes
well) and said:
"Well I don't want James. So I guess it's me and Bobby. Courtney, James is
all yours."
That sealed the deal, and strangely enough everyone left the meeting pretty
satisfied. The boys were understandably nervous for what was to come, and
disappointed to curb their own Halloween plans in favor of the girl's plans
for them, but at least they had a way out of their pictures predicament
(assuming the girls told the truth about deleting them).
Each of the boys received a text later from their "teammate," confirming
contact information and whatnot. Turns out the number that texted them all
was Courtney's - Margaret knew that none of the boys would have her number
already so it worked out well. And she was unsurprised but glad that all of
them showed up. After all, she didn't really want to release the pictures,
she wanted to do another dress up session, this time where they would have
more time to work on their boys, and get to take them outside. That,
surely, would teach them not to mess with her, and she would get the
satisfaction of seeing James emasculated again. She reckoned that for these
kinds of punishments, once really isn't enough. The first time is an
appetizer, the second time is the entree. Maybe there would even be
dessert? She hadn't decided yet.
For the next week or so the girls made preparations and the boys didn't
have much to do, so there wasn't much contact. The next Friday, now a week
before Halloween, James and Bobby got a group message from Margaret and
Courtney. They were to meet at the Halloween store a town over at 10:00 the
next morning for further instructions. Anxieties high, James and Bobby knew
they had a real day ahead of them for sure.
When the boys arrived, Courtney and Margaret were already there, waiting
outside. James and Bobby approached them sheepishly, the anticipation
slowly killing them. They didn't know whether it was better to know their
costume and get accustomed to the thought, but fear it, or if it was better
to be surprised. In that case, they'd sacrifice their anxious build up for
uncertainty, which also carried a weight to it.
Courtney spoke up. "So gents, you've noticed that we're here as a big
group! All four of us together, how sweet! Well, we heard the Maddie and
Becca already chose costumes for your other friends, and we thought it
might be more fun to do things a little differently. But first, let's
establish some rules."
She continued. "From this point on, you may not speak to each other until
everyone has left the store vicinity. At that point, you may not discuss
what happened here until Halloween day. Clear?"
Confused, they both nodded.
Margaret picked up from there. "We both realized that we had so many good
ideas and didn't know how to pick one, so instead we thought of a little
game. You two are going to pick each other's costumes!"
"How cute!!!" chimed in Courtney.
Margaret kept going. "Bobby you can go first. Go ahead and head into the
store and pick out something for James to wear this Halloween. Your budget
is $50, but you can go a little over if we really like what you've
selected. You will make your selection, meet Courtney by the register to
pay, and give her James' outfit. You may not tell James what you are
picking at any time. We'll check your phones if you act suspiciously, and
don't think it will be good for you if we find out you shared information.
Also remember that what you pick is not the whole outfit - just the start,
and we will fill in the rest later! Bobby, go ahead!"
Bobby entered the store, observing all of the classic scary decorations and
moving pieces no one ever actually bought, but were fun nonetheless. Aisles
of wigs and masks and costumes filled the usually vacant storefront, which
became everyone's favorite place this time of year. He had a decision to
make.
A few thoughts entered Bobby's head as he thought about his decision. He
seemed to have pretty much free reign, which meant he could go real easy on
James if he wanted. Maybe a ninja? Firefighter? Some standard men's
costume? But would James be so kind back? After the last adventure with the
girls, he expected they probably wanted to get the boys in dresses again
somehow. Given that, could he really allow James to be the only one not
embarrassed? No way. He knew how people saw things like this. If they
noticed two boys dressed up as girls, but one waaayyy more girly than the
other, which would they remember? Bobby decided his best bet was to make
sure he was not the worst looking one of the bunch, the others be damned.
Second worst, fine, third worst, better. But he would not be the one hit
hardest, and by God Almighty, James would not be the one, if anyone, to get
off easy here. He, after all, put them in this mess in the first place, and
Bobby supposed James would not be generous back. Bobby headed, just as the
girls hoped, straight to the women's sections.
Bobby was surrounded by pure femininity and sex appeal, with costumes
displayed by blond, long legged models on all sides. He took a good look at
ladybugs, bumblebees, fairies, nurses, princesses, greek goddesses, the
works, before his eyes finally met the object of his affection. He quickly
grabbed the bag containing James' prize and headed towards the counter,
where he handed it to Courtney. Her eyes beamed as she saw Bobby's
selection, thrilled both that he picked a women's costume and that it was
such a great one. She paid, stuffed it in a bag so James couldn't see, and
walked out.
Bobby and Courtney exited the store together, as Bobby looked down at the
ground to avoid eye contact with James. James couldn't get much of a read
from Bobby's face, but from his behavior he could only assume the boy did
him dirty. That was fine, he could play dirty right back. Courtney and
Bobby left to head back home while James and his sister remained. James
found the costume he knew would make Bobby the biggest sissy around, or so
he imagined. He still had no idea what Bobby chose for him, but he sure as
hell knew Bobby was in for something sweet.
"Got him good!" said Margaret when he handed her his choice.
"Hell yeah I did," he said with misplaced pride. In the moment it felt like
just another prank - for a split second he forgot it was coming right back
to him. A small consolation, at least, was that his was coming from
Courtney.
With the decision made, Courtney and Margaret began planning around what
they had been given, and boy were they satisfied with the results of their
little game. Courtney suspected that by putting the choice into their
hands, they each picked something more embarrassing than she ever could,
because she didn't know precisely what boys would be most sensitive to.
Margaret's sick idea worked like a charm.
Friday night, as the girls were getting ready for their first party of the
weekend, they messaged the boys. Each of them would report to their
teammates house to get ready beginning at 4:00, and they would plan to hit
the streets by 7. That gave everyone lots of time to get dressed and ready,
and it gave the girls a chance to get the most of the torture they were
going to dole out.
Each boy arrived at his teammate's house right about on time, though James
made a point to arrive early and see if he could get some time watching
Courtney get ready. Halloween had finally arrived, and it was time to
settle up on all of their debts.
_ _ _ _ _
Note to the reader: the following sections may be read in any order, as
they occur concurrently.
JAMES
James arrived at Courtney's, and after answering the door she guided him up
to her room, saying hello to her parents along the way. James and
Courtney's families were friends since she and Margaret had known each
other since they were 5, and Courtney's parents knew James well and greeted
him warmly, though unsure of why he was unaccompanied by Margaret.
Nevertheless, they brushed it off. Frankly, knowing both James and their
daughter, they were completely unconcerned with them having sex or anything
like that. Courtney would never, not with him.
James may have been the one boy that they most doubted Courtney would ever
seek out, and they were right. James was of course there for another
reason, and while he held onto hope that he might get a chance to charm
sweet Courtney in the process, those chances seemed to evaporate as he
entered her room and she got down to business. With a sly grin she closed
the door and sized up the boy, looking him over for any imperfections she
might have to fix. She had the upper hand in every way - she was stronger,
taller, more trusted, and better loved, and most of all, James was smitten
with her while she didn't care for him one bit. He would do whatever she
said - either because he wanted her, or because he feared her. If she did
her job well, she'd get both.
"So are you ready to see what Bobby picked for you? It's just so adorable I
can't bear it!"
That wasn't a good sign. If Bobby thought the same way that he did in that
store, this was bound to be something embarrassing.
Still keeping the mysterious costume in the bag now held in front of her,
she continued. "Your friend has such good taste! I hope you were as kind
back! Ready to get started?"
"Yeah, I guess," he muttered. He saw no way out, and if that was the case
he guessed doing it alone with Courtney wasn't the worst situation ever.
After all, it could've been someone less hot, or god forbid, his sister.
The last time they got him it was a group effort, and despite his
predicament James noticed who really knew what they were doing with his
makeup, and who didn't. Courtney was one of the few who seemed interested
in making James look somewhat presentable, if girly. Her influence lost out
to the other voices who wanted a more extreme look on that one, he
recalled, but even so, whatever came next he trusted her to at least do it
well.
She handed him the bag. "Go ahead! Open it!" He reached in.
Like the sword from the stone he removed the prepackaged costume from its
plastic home and gasped a sigh of despair as he got his first look at it.
"Strawberry Sweetie," was clearly a pseudonym for a certain little girl's
toy brand, and today, it would be another name for James.
"Let's do your makeup first!" Courtney exclaimed to a dumbfounded James. I
have so much in mind and I just can't can't can't wait to see it!"
Her bubbly fa?ade was annoying. He was head over heels for her, but that
didn't mean her obviously fake, over the top enjoyment was something he
particularly liked. On the inside, she was still mad about the camera
incident that began this whole thing, and without the other girls to hold
her back she would make James the girliest thing he could be.
She took him over to her makeup desk and placed him facing the mirror. She
told him to take off his shirt and slowly he acceded to the demand,
preparing himself for another miserable evening dressed up. She took his
nails in her hand first, since they would need time to dry.
"Now James, I need you to keep your hands still and not touch anything
while they dry. I swear if you mess up one of them I'll just remove it and
restart and you'll waste all of our time. I'm not sending you out there
without looking perfect, and frankly you should thank me for that."
James considered this whole event a curse, but Courtney's words resonated
with him, and he found new perspective on the night ahead. He had only a
few options for how to play this off, and they all depended on how good he
actually looked. If he looked terrible, he could claim that he lost a bet
and had to do everything himself. Weird, and embarrassing, but some social
karma could be salvaged that way if he seems like someone who sticks to his
bets. Trouble is, if it was a little too much and he looked a little too
good, that excuse wouldn't work. Everyone would be able to see that he
tried to look cute and girly in a non-ironic way and that was by far the
worst thing that could happen. But in the final case, if he looked so good
that he actually passed as a girl, then it was possible that people might
not recognize him at all. It would be embarrassing to be there, but if
nobody knew then nobody could care. Bizarrely, he reckoned, the best case
scenario that wasn't "don't dress in a girl's costume," was "look so good
they think you're a real girl." Ironic, almost.
When James snapped out of his little calculation daydream he saw that
Courtney was finishing up his fingernails, and she was quite the talent.
Each nail was painted a shiny red-pink color, and Courtney added a number
of little black dots to each one to replicate strawberry seeds. It was very
cute, even he could admit. For a girl, that is.
Courtney watched his hands to make sure they were kept still. Strictly
speaking, she overstated how important it was that he not move - really, as
long as he didn't touch his nails to anything it should be ok. But telling
him not to move had the positive side effect of keeping him from messing
around with his makeup while she applied it, and made the whole process a
little less annoying.
She got to work on his face, which was much easier said than done. James
had shaved the day prior so his face was mostly hairless, although it took
a good bit of foundation and concealer to cover some of the more shadowy
spots and even out his complexion, as well as provide a base for the rest
of the makeup she'd apply. She told him to close his eyes as she applied a
succession of pinks to his eyelids, first a very light shade in the inner
corners and then darker hues at center which she blended outward. She then
took a green glittery liquid eyeliner, and just along his upper lash lines
drew a thin strip of the shimmering substance, covering the entire length
of his eyes. A very thick coat of mascara was applied to his eyelashes,
extending them out into the forefront of his face, drawing all of the
attention to his newly made up eyes.
With an eyebrow pencil, Courtney first filled in James' brown eyebrows and
guided them into a slightly more feminine shape, and then she seemed to
polka dot the pencil onto his cheeks and over his nose and forehead. When
she finished, James was bearing an adorable set of new freckles, which she
anticipated would later bring together the whole look. It was the little
details that made the difference, of course.
Courtney wasn't in a rush, and took moments of pause as she went to
examine, think, and readjust her plan for him. She pulled open one of the
desk drawers, reveling an apparent mountain of all kinds of lipsticks and
glosses and tints, and combed her way through until she found the perfect
shade. It was a delicate pink liquid lip with strawberry overtones,
perfectly matching the color of the wig he was about to put on later.
"Look at me," she said forcefully, and James tuned his head to face hers,
where she had her weapon drawn. She very carefully traced the edges of
James' lips before gently filling in that outline with the sweet smelling
substance. James' lips were matte and just as she wanted them - it was
clear as day that he was wearing lipstick, and a very cute one at that, but
they didn't draw attention away from his eyes and new freckles which were
the real show. She finished with a light pink blush that was hardly visible
at the moment over James' reddened face from embarrassment, but would make
a deceptively big difference in the overall cohesion of the look.
"Now let's get you dressed!" Courtney announced. Apart from a few "oohs,"
and "ows," James had been pretty much silent up to this point. He tried to
take his mind off of the torture, and while he could distract himself for a
few moments at a time there was no getting over the fact that Courtney was
doing his makeup and about to dress him up as a Strawberry Sweetie for the
whole world to see. Maybe he should have just let those pictures come out -
at least then he wouldn't have to show it live for anyone to see. Of
course, if he saw anyone he knew he had one potential excuse, that being
that it was Halloween night, and in the long run you could get away with
dressing weird on Halloween, even if people give you hell for it in the
short term. Those other pictures were from some random day in the middle of
the year, and if people saw him dressed up then, he'd never shed the pansy
label until college.
Courtney commanded James to strip down to his underwear, and he did,
revealing boxers with hearts on them that he clearly intended and planned
for Courtney to see. She giggled and handed him a pair of bright pink
panties with white lace trim around the edges and leg holes, and frills all
over.
"Put these on first," she said. James looked reluctant.
"Nobody is going to see my underwear, why can't I just wear mine?" he
requested.
"Oh but James, you're forgetting that this is a punishment aren't you? You
got so caught up in your beautiful makeup you forgot the point of this
isn't for you to have fun, it's for me to have fun at your expense! I know
when I'm getting all glammed I can forget things too so I'll forgive you.
Now put the panties on."
That last sentence wasn't a request, it was a demand. James slowly obeyed
and she turned around, and when their eyes met again, James was wearing
nothing but a face full of makeup and some pink frilly panties.
"Maybe we can go out just like this! Wouldn't that be fun?" she chided.
"But then Bobby would be disappointed he didn't get to see the whole
costume he picked out. I guess we have to continue."
"Fucking Bobby," thought James, remembering that he was the one who
actually picked out this outfit for him.
"I have just the bra to match!" Said Courtney as she tossed him an
impossibly soft garment. Around the each of the cups were soft frills of
fabric that seemed to just hug James' chest as he put it on, securing it
backwards in the front first and then turning it around and putting his
arms through the straps. Adorable.
"Now put on the tights in the package. Go ahead."
James actually knew how to put on tights from a peter pan costume he wore
in elementary school, but not wanting to give away that he could, he asked
Courtney to help him. Like a mother to a small child she bunched up the
tights at each legs, put them on James? feet and unrolled the whole
ensemble back up his legs, where James took over for himself. He watched as
his legs became encased all the way up in green and white horizontal
stripes, each color alternatingly wrapped in rings around his slender
calves and thighs.
The dress came next, and James slipped it on without too much trouble even
though it was a bit tight. At the top, a green plaid patterned chest
section bloomed outward like an Oktoberfest dress would, making room for
his unfilled bra below. The short sleeved pink garment was tight above its
high waist, but the beautiful reddish-pink skirt blossomed outward,
supported by a built in petticoat. The dress fell right about to James?
knees, and matched his makeup perfectly, just as Courtney expected. She
told him to sit down.
She slid the shoes she had chosen onto James? feet, and told him to walk
around for a minute. The were 3 inch matte pink pumps, and James had a hard
time navigating at first, even though they fit perfectly. He?d have to walk
around quite a bit later that night, and it was prudent to get used to them
early. She had him put on a pair of pure white polyester fingerless gloves
that came with the costume, hiding his hands but still revealing his
strawberry fingertips out the ends.
Finally, Courtney brought the 24 inch strawberry pink wig over to James?
head and placed it on, letting the hair fall straight down in front of his
shoulders, split at the middle. The last touch was an included signature
strawberry hat, a large and poofy bonnet-type thing which rested at a
slight angle on his head, secured to the wig with a few well-placed and
well-hidden bobby pins. James no longer resembled anything masculine at all
? one could hardly tell if he ever really had any rugged qualities about
him. His outfit was an abundance of color, which his makeup didn?t help to
dampen. As he blinked he saw quick flashes of green from his eyeliner in
the mirror, peeking out from behind his newly long and full lashes.
"Give me just a few to get ready, and we?ll get going to meet the others,"
said Courtney, as she escaped into another room to change. When she
returned, Courtney was wearing an Alice in Wonderland costume, which showed
off her perfect yellow-blonde hair as well as anything ever could. The
dress was actually a fairly similar style to James?, with white puffed
short sleeves and flared out skirt falling just above the knee. She wore
black fishnets underneath, and shiny black heels that quite literally
elevated her beauty, and though she seemed to finish her makeup in just
five minutes, it came out flawlessly as ever, with blue eyeshadow, red
lips, perfect eyeliner and all. Courtney really knew what she was doing,
and that was evident in both of their get-ups.
They walked downstairs, said goodbye to Mom and Dad, and headed to James
and Margaret?s house to meet the others. Courtney?s parents wondered who
the adorable girl that left their house in the pink and green was. They
didn?t remember a girl entering, but Courtney had a lot of friends so maybe
they just missed it.
DYLAN
Just like the first time around, Dylan may have been the most reluctant to
actually go through with this stupid idea, but he had so much on the line
that the choice was obvious. He arrived at Becca?s on time and followed her
upstairs, where she brought him into her moved-out older sister Sadie?s
room. Apparently, it was a bit bigger and more than a bit cleaner than
Becca?s, and would give Dylan some privacy when he needed to change, or
better yet, privacy for her when she needed to change in her own room.
Becca beamed with excitement. She had been the one to enjoy the boys? last
makeover the most, and she was the one who whispered in Margaret?s ear that
they might want to do Halloween too, just to drive the point home. Becca
wasted no time playing on Dylan?s anxieties ? he had not gone into the
first makeover very willingly, nor this one, but nonetheless he was there
and they both knew what was about to happen. Dylan didn?t know the costume,
but based on the conversations so far he saw no circumstance where he
wouldn?t be dressed up in girl?s clothes again. Part of him just wanted it
over with, though part of him hoped it would never start.
Becca closed the door, ready to begin.
"You must be wondering what?s in store for you! I picked you myself,
remember?"
"Yeah, I remember," responded Dylan. He didn?t know why she wanted him
specifically but that may have been the one thing about this shit he didn?t
hate. Becca was a stunner, by her face, her hair, her body, her fashion
sense ? you could hardly find a guy that didn?t think she was hot as can
be. Dylan was no different, although he had written off any chance of
talking to her, letting alone actually spending any time with the girl, and
especially alone.
"I had a lot of fun with you and your three friends that other night, I
must admit. I couldn?t be happier that you tried to spy on us." She paused.
"You know what that felt like, Dylan? It felt like I was playing with a
doll all my own, that?s what you were just my little pretty doll that I got
to dress up and do her hair and her makeup, and there wasn?t shit you could
do about it, was there?"
Dylan gulped. She was on the loose and he would be her next victim,
whatever that meant.
"And now I get another chance!" she said, turning to him with a classic
evil grin. The prettiest evil grin in the world, but evil for sure.
"Dylan, I picked you because you were the most fun. You hated it even more
than the other boys and I could tell, and I loved it even more for that.
You even got off easy with the outfit last time because we had already
decided on the best stuff for Cam and James, and Bobby?s top wouldn?t have
fit you. But now, rest assured that you are mine and I?m going to make you
squirm. I?m really glad you came, Dylan. This is so much more fun than just
releasing those pictures would have been."
The way she said ?squirm? sent shivers down Dylan?s spine, and even the
black hair on his head seemed to stand on end.
"Get naked," she commanded. She didn?t look away as Dylan timidly obeyed
her order. She retrieved a pair of black satin panties with violet trim
from the bag of clothes she had carried into the room, and threw them at
Dylan?s face. He knew what that meant, and wearing panties was better than
wearing nothing.
"You know, your legs are a bit hairy. We can?t have that, can we?"
Dylan said nothing.
"Can we?" she reiterated, angrier this time. Dylan answered a quiet "no".
"Smart girl Daisy! Now go in the bathroom and shave your legs and chest and
come back quick. You have 10 minutes."
Dylan presumed that Daisy was now the name she?d be calling him, and he
didn?t know his penalty for running out of time, but he didn?t want to find
out. She had set out a razor and shaving cream and he got to it, cursing
his own life the whole time. How the hell did James get him into this?
When he finished, Becca was there waiting. She had a black bra in her hand,
dangling down in a way that could only mean "I can?t wait until you put
this on." Again she handed it to him and he tried his best the secure it in
the back before giving up. Becca approached him from behind and secured the
strap, lightly slapping his ass as she retreated back again. He turned
around to face her, and revealed a small pink bow between the cups, and a
bright pink complexion to match.
"Gosh aren?t you just precious!" Becca exclaimed. "I?m having so much fun,
aren?t you having fun?"
Dylan didn?t answer. She went around to his back and snapped his bra strap,
send a stinging pain across Dylan?s back.
"Having fun?" she reiterated.
"Yeah, so much fun," he said with little enthusiasm.
"Try that again Daisy, for a moment there your voice sounded low and
masculine, and you seemed so unexcited. Let?s fix that."
Dylan looked at her with a silent rage in his eyes.
"I?m serious, Dylan. Don?t? test me," Becca said intensely.
He acquiesced. In a gross falsetto he spoke with a lying excitement "I?m
having so much fun Becca!"
"Great to hear! Now Daisy, I don?t want to tell you what to do all day ? I
want you to have some choices too! I have your costume all picked out, but
do you want to do the clothes first, or the makeup? Your choice!"
Dylan felt naked in the tiny black bra and panties he wore, and considering
the makeup was the worst part he figured he ought to save that for last.
"The costume, I guess," he answered, still maintaining his high tone while
he did so. Becca was pleased with her progress, and so quickly he was
already following her orders. This was going to be fun.
"Ok! We?re ready to see it then! I told you that I just loved how you were
my precious little doll last time, well this time you?re going to
be...exactly that! A little girly doll that I get to play with."
She pulled out a costume dress that made Dylan nearly gag. It was a mostly
white little girl?s party style thing with a wide puffing skirt, covered
all over in different sized purple polka dots. A matching solid sash
wrapped around the waste, and visible lace at all of the openings seemed to
only exaggerate the girlishness of this thing. Before he could put on the
dress though, she gave him a few other items to put on. First, she told him
to pull up some extremely sheer, slightly white-tinted pantyhose that gave
his legs a shiny porcelain glow. Over the hose she had him slide on some
adorable lace frilly socks that delicately encased his feet, every tiny
motion reminding him of his lacy, girly predicament. Finally she gave him a
pair of black Mary Jane shoes with buckles over the top to wear. They
glided over his socks as he slipped them on, and he noticed that the
ruffles at the top of his socks at the ankle stayed prominently visible
above his shiny shoes. He stood up as she slipped the garish dress over his
head, and as his head popped up through the center and his arms found the
right holes, a look of total despair fell over Dylan?s face. He struggled
to conceive of how this could ever happen, and worst of all, at the hands
of the hottest girl in school! She was crazy!
Becca saw his expression turn demure, and laid it on even harder.
"Don?t be sad Daisy, we haven?t even gotten to your makeup yet! That?s the
best part!"
Apparently for Dylan, the worst was yet to come.
She waltzed her little doll over to the vanity and sat him down, making
sure he brushed his puffy skirt underneath his bottom as he sat.
"First, Daisy, we?re going to get your face looking all perfect and
dollish. I?ll do this part since it?s a bit tricky, but you can help with
the next one."
It took a while before she finished with the super pale foundation and
powder, but when Becca was done Dylan?s face looked both perfectly smooth
and delicately fair and pale, exactly how she wanted it. She took an
eyeliner pencil and drew a few cracks around the edges of his face, as if
the doll was slightly broken, like an antique.
"Now we can do your eyes! I think part of this look is that you?re a little
girl doll and don?t really know how to choose makeup yet, so let?s do some
fun colors. Pick one from this palette."
Becca showed him a seemingly endless selection of colors, all of which were
vibrant shades of rainbow colors, nothing even slightly natural. Dylan
wanted no part of this decision - why couldn?t she just torture him
normally instead of making him participate? Becca?s cruel game was working
perfectly.
Dylan did the only thing he could think of. He closed his eyes, moved his
finger around in front of him, and finally pointed at some square without
looking. He landed on a lilac shade and Becca just gushed at the selection
since he actually picked one that would match his purple outfit! She not so
carefully swiped it over his eyelids, leaving it slightly imperfect as
you?d expect a little girl?s makeup to be if she did it herself. With
liquid eyeliner, she drew a thin line outward from the halfway point of
both his upper and lower lids, creating bold dimension, and on the inner
corners she placed a small dot of bright white highlighter.
Becca took out a pair of false lashes and told Dylan to close his eyes. She
applied a thin line of glue to each one, and after letting it dry for just
a moment, stuck them perfectly in place on Dylan?s upper lashes. The
falsies brought the doll imagery to life, and even more so as Becca curled
his real lashes into the fake ones, making the whole thing appear even more
dramatic. She then applied a bright pink blush to his face with a heavy
hand, leaving him permanently flushed in the cheeks.
Finally, Daisy was ready for some lipstick. Becca found a light violet
shade that matched his dress very well, a light but bright pink that took
feminine to the max, and a vibrant red in case Dylan was leaning that way.
She placed them upright on the vanity in front of him.
"Pick one," she commanded.
Dylan wanted to do nothing more than scream ?None of them!? and run out the
door. Unfortunately, in the Mary Janes he would have a hard time running,
and if he bailed now then he would have let her do this to him for
absolutely nothing. The red and the purple both scared him, so he pointed
to the pink.
"Put it on," Becca demanded.
"Why don?t you just put it on me? I don?t want to do this at all, let alone
do it myself." Dylan spoke up in a rare rebuttal.
"Daisy, a girl needs to learn how to put on lipstick and you need practice.
Go ahead. You know what happens if you don?t."
Dylan had no choice, no moves, and no escape. As he reached for the bright
pink plastic tube it wasn?t like he was moving his own body ? it was like
he dissociated from himself and watched some demon possessing his own body
take the lipstick and slightly lean forward towards the mirror so he could
see better. Dylan carefully drew the chocolate-scented stick across his
upper and lower lips, missing no spots at all. When he finished, like an
instinct he pressed his lips together and popped them in a kiss as he
released. Becca came over to the now almost fully feminized boy, and over
his new bubblegum pink lips she added a few subtle details with the same
eyeliner pencil as before to enhance his broken doll look.
"Time to do your nails! You get to pick again ? here are a few, go ahead
and apply the one you like best."
Dylan didn?t even argue this time. After doing his own lipstick his ego was
destroyed, and there was nothing left to save by wasting time. He chose
purple to match his eyes and dress, and when he finished painting his nails
the look was almost complete. Becca came up behind him with a black medium-
length wig to match his natural hair color. She pulled it back into a
Lolita style with a large ponytail on each side of his head, securing them
with purple ribbons tied into bows which fell over Dylan?s ears and tickled
his neck. For the final touch, she procured a black choker with a small
rhinestone pendant in the center. She placed it around his neck, and
secured it in the back.
When Dylan looked in the mirror, he brought his hands to his face in
surprise, even further emphasizing his feminine image as his purple nails
cupped his lilac eyes and bright pink lips. His face was pale, and the
white dress and pantyhose emphasized his porcelain appearance. Becca
escaped the room briefly to change into her own costume, more than
satisfied with the work she did on Dylan. For the next few minutes Dylan
could only dwell in the room and think of what had just become of him. He
didn?t even just look like a girl like last time; he looked like the girl
to end all girls. He was, now, at the peak of sissy and Becca wouldn?t have
done it any other way.
When she eventually returned she was wearing a sexy Minnie Mouse costume,
consisting of extremely short red romper-style shorts with white polka
dots, and a similar colored crop top. Between them, she was wearing a
fishnet bodysuit visible across her midriff, and up on her head she wore
classic mouse ears over her gorgeous red hair, and the brightest red lip
Dylan had ever seen.
At that point, it was time to go and meet the others. Becca led the way
down the stairs and outside, little dolly Daisy in tow.
BOBBY
When Bobby arrived at James? house (Margaret?s, but he thought of it as
James?), Margaret greeted him with a smirk. Grabbing him by the wrist she
guided him downstairs, back to the place where their first makeover had
occurred. The scene of the crime, in his eyes.
Bobby noticed that she had set up the room almost exactly as it had been
that fateful night, which must have taken some work, since he was there to
visit James earlier in the week and the furniture hadn?t been moved yet. It
was like Margaret was trying to trigger his memories of the previous
encounter, and if that were true, she had succeeded. Bobby?s long held
affection for Margaret had fallen that day, and ever since he was hardly
able to look at her. He never had a chance with her, but it still felt like
a love lost. Now he was back, and of all things, had to let her do it to
him again. Compared to his friends, Bobby felt he might have gotten
comparatively lucky last time, although that wasn?t saying much. This time,
with all of Margaret?s evil attention on him, he was more vulnerable than
even before.
"Remember, Bobby," Margaret said with a nefarious grin. "I didn?t pick this
for you, James did! So if you don?t like it, you can blame him." But don?t
worry, I think you?ll like it, after all, I love it!"
Bobby winced hearing all of that. This was so reminiscent of his first
torture, and it sounded like round two wouldn?t be any less terrible. If
anything, the first time she had to divide her focus between the four of
them. This time, she only had to worry about him.
At this time, Margaret was wearing just sweatpants and a comfortable tee,
but even at her least put together she was still incredibly beautiful. She
spent so much time next to the only girls in school prettier than she was,
that it was easy to forget how much she stood out on her own. Bobby was
suddenly overcome with a rush of emotions as his eternal crush on her
returned suddenly in full force. The way she spoke was intoxicating, and
for a split second he almost forgot that her words were hardly a palliative
for what she was about to do. She had been really pissed that day with the
camera, and while she seemed excited, Bobby definitely got the sense that
she still wasn?t over his and his friend?s little crime.
"Ok Bobby, I suppose you know the drill by now, right? Remember?"
Bobby sighed and slowly approached the vanity in the center of the room.
Still in all of his boy clothes, he sat down gently, and faced himself in
the mirror. The person looking back across the glass was visibly afraid.
"I?m not going to show you your costume until you actually put it on ? I
think it?s more fun that way."
She apparently liked that method for doing this kind of thing, based on her
choice of order last time.
Margaret was intent on keeping Bobby?s natural freckles visible and at the
center of the show, so just like last time she applied a low coverage
foundation and concealer very lightly, to keep his skin looking as natural
as possible. Some powder evened out his complexion, and with a very soft
large brush she applied some contour and bronzer to shape his face into a
more feminine pointed chin and high cheekbones. Bobby stirred in his seat,
not knowing whether to sit still and take it or try ever so slightly to
resist, to show that he wasn?t enjoying himself. After a few minutes of
Margaret telling him to stop fidgeting, he finally calmed down. Once he had
makeup on, it didn?t really matter anymore, did it?
She turned his chair around away from the mirror for the next steps, since
they required a bit more attention on her part. She decided to start with
his eyes, and after a quick coat of primer she began to brush a glittery
gold eyeshadow onto his lids. Bobby could see the glisten on the brush as
she brought it to his face, slowly painting her masterpiece. She followed
with a thin line of eyeliner, which she very carefully applied to each of
his upper eyelids, choosing not to add a wing. She took out another
eyeliner, this one in white, and very carefully applied it to his
waterline, a process that Bobby enjoyed the least, but did give his eyes a
vibrant quality that Margaret really liked using for her own makeup.
Margaret decided to curl his lashes, to Bobby?s discomfort, only to later
decide that fakes were the way to go for his costume. She carefully took a
pair of beautiful long lack false lashes from their packaging, and with the
greatest of skill glued them onto Bobby?s upper lash line. After a quick
adjustment to make sure that everything was in place, Bobby was the new
owner of lashes that seemed to cover his peripheral vision like horse
blinders. He felt their physical weight on his eyelids, and could not
believe how far they extended out when he brought his hand near his face.
As he did so, Margaret almost shouted:
"We totally forgot your nails! Ugh Bobby, why didn?t you remind me? We need
to do them now so they dry in time for you to put on the costume, come on!"
She chose a brilliant shade of iridescent emerald green that brought his
hands to life and would make a supermodel jealous, as she generously
applied two coats and finished with a clear coat on top. Bobby could not
help but examine his newly feminized hands, and frequently curled and
uncurled his fingers, examining how the light flickered and glimmered off
of his new nails. They distracted him slightly from what was to come, even
though they were part of the makeover itself.
Margaret applied a shiny highlighter to the tops of his cheeks bones, just
under his eyes, which was bright and visible whenever Bobby turned his head
and let the light cast across it. She chose to use a very small amount of a
very natural blush to keep from overblushing and distracting from his eyes
and natural freckles. At last, she moved on to his lips.
She turned Bobby away from the mirror again (he had been sneaking glances)
and while holding his chin steady with her left hand she brought a wand
covered in light pink liquid lipstick up to his mouth, and generously but
carefully applied it all over the boy?s soft virginal lips. She gave it a
minute to dry, and brought his face up to hers again. With a red lip liner,
she traced the outline of a heart in the center of his now pink lips, and
using a bright red liquid lipstick, filled in her artwork leaving a perfect
kissable heart at the focal point of Bobby?s face.
"Good. Now press your lips together and rub them a little bit."
Bobby was initially nervous to do so for fear of ruining his lovely little
heart, but that feeling quickly passed when he remembered he was, in fact,
a boy who shouldn?t be wearing lipstick, hearts or otherwise. He did as he
was told, and as he pulled his lips apart he noticed that the red heart in
the center of his lips had kept its shape, but now lit up in sparkles of
red glitter, which he could feel.
"Like that trick?" said Margaret. "It?s called a glitter-flip lipstick ?
really blows people?s minds in the right situations."
Bobby would have admitted he was impressed, if he wasn?t the one wearing
it.
Margaret moved on to his hair, and as she combed through his brown locks he
noticed her adding extensions that blended into his existing cut, turning
his hair from 4 inches to a realistic 18. When she was finished attaching
the extensions, Margaret split his new hair down the middle in back,
separated the two parts, and braided each one. As she braided, Bobby
watched as she took a long red ribbon and skillfully weaved it into and
through the braids, leaving two long bright red streaks goingn down the
back of his head. His new braids traced down the back of his head and fell
just in front of his shoulders, where Margaret secured each one at the end
with a red bow, matching the ribbons. In the front, she left a thin curled
strand of hair on each side of his face, one a bit longer than the other,
seductively framing his newly beautiful visage.
"Time for your outfit!! Are you excited to see what your friend chose for
you?"
"Thrilled," Bobby replied sarcastically. Margaret laughed, it seemed like
she was having a lot of fun with this, especially doing his hair. She had
the prettiest laugh, and Bobby was enamored again.
"Take everything off and put on these," she said, handing him a pair of red
panties and black thigh highs with red bows in the front. Bobby started to
walk towards the side room to change.
Margaret interrupted his attempt at privacy with a curt "ahem...right
here." He looked at her in disbelief; there was no chance he was about to
change in front of her.
"Please?" He begged.
"Fine. You can put on the panties in there so I don?t need to see your tiny
little thing, but come back out right after. You?ll put the thigh highs on
in here," she decided.
Never before was Bobby grateful to be told he could go put on his panties
but off he went, pleased that she entertained his request for the smallest
bit of privacy. As he stripped down he felt anything but naked, wearing
what felt like an extra pound of makeup and hair on his head. He slipped
the red satin garment on, disbelieving that he was doing this here, again,
and headed back out.
"Wow, look at you cutie pie!" Margaret tauntingly gushed. "Now let?s see
you in these!"
Bobby sat down and raised one foot at a time off the ground as Margaret
took the thigh highs and rolled them up his thin legs ? they were opaque
enough to cover what little leg hair he had. The pop of color in the bow at
the top of each one paired with his hair accessories very nicely. Margaret
finally brought out his costume, and Bobby couldn?t believe what he saw, or
rather, what he didn?t see.
The schoolgirl costume had almost nothing to it! A teeny tiny skirt and a
small bra-style top, plus a few accessories. Bobby would be half naked out
there by the looks of it!
"Cute huh?" she goaded. "I might have even worn something similar if James
didn?t pick this for you!"
There?s nothing Bobby would have wanted more than to see Margaret dressed
up just as he was going to be, with perfect makeup and a sexy, nothing
little outfit. She put the miniscule crop top over his chest, which was
basically just a black fabric glorified bra which tied in the middle. It
was trimmed with red plaid, which matched the incredibly short skirt he
would be wearing next. He stepped into the skirt and it barely covered his
ass, let alone any of his legs! The red tartan plaid pattern said ?catholic
school?, but the tiny length said ?porn star?. If Bobby leaned over just a
bit too far, anyone looking could get a clear view of his panty clad
bottom.
"You know what Bobby, I?ve changed my mind. Those panties are a little too
boring ? wear these ones instead."
There?s no way Margaret didn?t have this planned form the beginning. Not
only was he going to have to wear panties, and put them on twice, but he
was lulled into the false security that somehow, this wasn?t going to be
the worst thing in the world. Oh it was. The new pair she gave him was pure
white hipster panty with pink trim, and a plethora different sized pink
hearts all over.
"See! It matches your lipstick! How precious!"
Bobby started to lightly cry through his heavily made up eyes. This was too
much to handle, and he had nothing he could do about it. The only thing
worse than being dressed up was having everyone know it, which would happen
if those pictures were released.
"Oh Bobby, come on. Come here," Margaret said tenderly. Bobby never heard
her say anything tender in her life ? Margaret wasn?t exactly a sentimental
type. She reached around him in a sweet embrace, and she lightly caressed
the back of his head as he sobbed.
"Ok Bobby, maybe that was too much. You don?t have to wear the panties if
you don?t want to. But if you did, it would make me really happy. After
all, you?re already in panties, this is just a little bit different."
She thought quickly, and made him an offer. "Tell you what Bobby, if you
put these on then I?ll let you watch me dress up in my own costume, the
whole thing. Would that make you happy?"
Considering that?s pretty much exactly what he had hoped to get out of the
whole camera incident, this was a game changer. Margaret knew he had a
crush on her, and he knew it would never really be reciprocated, but now he
had a chance to watch the most beautiful girl in the world change in front
of him? Maybe this whole thing had a glimmer of hope to it, beyond the
glimmer of his eyeshadow.
Bobby silently and slowly reached out for the garment, hiding his still
teary face (luckily, his makeup was totally intact). Standing in place he
reached under his tiny skirt to remove the red panties he was already
wearing, and turning away he slid up the new white and hearted one.
Margaret smiled, and Bobby?s look was all but complete. She took a couple
dangly red-heart shaped clip on earrings and secured them to his earlobes,
and added a black choker around his neck. She found a temporary tattoo of a
blue dog paw college logo and stamped it to his cheek, and as she pulled
away, very lightly kissed him on the other cheek. Bobby?s heart pounded and
his blush intensified.
Margaret upheld her deal, and Bobby watched her first apply her own makeup,
which was more erotic than he expected. He watched her transform from a 10
to an 11 before his eyes, as she applied a reddish red brown lipstick and
added a bow to the back of her auburn hair. She stripped down to her
underwear and Bobby didn?t blink once as she covered her sexy blue lingerie
set with a tiny cheerleaders crop top and miniskirt in blue and yellow,
matching the oversized bow she wore above a perfect high ponytail. ?Go
bulldogs!? read the temporary tattoo she applied to her own face, obviously
matching Bobby?s.
"Ok Bella, let?s wait for the others, they should be arriving soon. I can?t
wait to see your friends!"
CAM
Cam arrived at Maddie?s, and rang the doorbell. Maddie answered the door
with a grin, dressed in normal clothes but eager for the afternoon and
evening to begin. She was the only one home, and took Cam by the wrist as
she led him upstairs to her room.
Maddie?s house was pretty big, and her room was something to gawk at. Her
room was nothing less than that of a low-tier celebrity, complete with a
large walk in closet, beautiful white furniture, and her own bathroom too!
Her bed was four-post style with a canopy and drapes, almost comically
similar to the most stereotypical rich-person-bed Cam had ever seen. He was
impressed with his surroundings, but moreover, amazed at the fact that he
was in MADDIE?S ROOM! More than a few of his fantasies began with something
like getting in here, and now that he was there, unsure of what was to
happen next, his emotions swirled.
Maddie turned to him. "So you must be so excited to find out what you?re
going to be this year! Actually, I decided we would do a couples costume ?
Angel and devil! Sound good?
A million thoughts rushed through Cam?s head. This wasn?t so bad at all! He
could be a charming devil with a stunner like Maddie dressed as an angel by
his side? This was a dream! Of course, that couldn?t be it. Maybe the devil
costume would be super embarrassing or something, like him just painted all
red. That wouldn?t be great.
Maddie escaped to the bathroom for just a moment, and came out wearing a
cute red headband with devil horns on top.
"How do I look my angel?"
"Uhh..great!" Cam stammered. She was so pretty. So off the chart cute he
couldn?t even comprehend. The way black her framed her face, her beautiful
Asian eyes and perfect skin, her body, everything about her Cam loved. He
hardly registered what she had really said, and it took a moment before it
clicked.
"Oh ok, I?m the angel," he thought. "That?s fine, I guess I can wear all
white or something, She?s going to be so hot. She is going to be sooooo
hot."
"Get undressed," she instructed, and the small boy followed her
instructions, down to his underwear.
"hmm...yeah, just what I thought,," she spoke. "You?re gonna need to shave
your legs and underarms. You don?t have much body hair but it?s enough to
show. The bathroom is over there, get going. Clean yourself up while you?re
at it."
"Wait, what? Really? What do I need to shave for?"
"Well the dress won?t cover your armpits so that has to go, and obviously
your legs will show so that has to go too. You don?t have enough on your
arms to notice so you can leave those alone I guess."
A dress. Fuck. He knew it couldn?t be this good, it was a couples costume
but apparently he still had to be a girl. Just lovely. This wasn?t a dream,
it was a nightmare, as if the first time around hadn?t been bad enough.
He also knew that he wasn?t getting out of it, and frankly he was so
enamored with Maddie that it didn?t matter. At this point, he?d do anything
for her if she asked. He entered the bathroom, where a run bath, shaving
cream, and razor waited for him. She had prepared, apparently. Without much
delay the boy entered the bath and, unbelievably to him, watched himself
remove all of the hair he?d spent 15 years trying, and barely succeeding,
to grow.
Still somehow, as he exited the water and dried himself off, he noticed how
much colder and softer his legs felt ? turns out that small amount of hair
actually makes a big difference! He felt cold, and vulnerable in a way that
he didn?t expect and as he exited the bathroom, Maddie was there waiting,
starting to get ready herself ? in just a black lacy bra and panties. Cam
nearly fainted at the sight, overcome with pure hormones and absolute
infatuation with this girl. And best of all, she seemed not to mind! She
was fine with him seeing her this way ? this was 100 times the payoff they
ever expected to get with that stupid camera! Maybe, just maybe, it was
even worth the humiliation he was about to endure.
She told him to sit down on the bed and he did.
Put these on, she said, and looked away. Cam reached out and took a pair of
pure white, super lacy panties and reluctantly slipped them over his newly
shaved legs. His mind was a slurry of conflicted emotions ? embarrassed,
thrilled, even dissociated almost as he could barely comprehend that this
whole crazy mess was happening.
"Ok, I?m ready"
She turned to face the newly shaved, panty-clad boy with a smile that knew
things were going just according to plan.
"Great, now the bra." She drew out a matching, beautifully white lacy thing
and slipped it over Cam?s shoulders, securing it tightly in the back. She
grabbed some kind of fabric from her drawer and gently filled in the cups
between cam?s chest and the garment to give him some amount of cleavage,
and took out a makeup brush and palette as well, with which she contoured
around where his boobs would be and created a surprisingly realistic
looking set of breasts, especially from a distance. Cam couldn?t believe
she gave him tits.
She pulled out another small, lacy garment, which Cam didn?t recognize.
"Do you know what this is?" She asked
He shook his head.
"This is a garter belt, it holds up your stocking and looks just oh so
sexy. Turn around."
Cam turned to face away from Maddie and she wrapped the belt around his
front, and secured it with the hooks in back. She threaded the garters
under his panties, and told cam to sit on the bed. He obliged.
"Now Cami, I don?t want you damaging my stockings, so I?m going to show you
how and do the first one for you, then you can do the second, ok? Watch me
first."
She took a slightly opaque but still seductively sheer, pure white stocking
and bunched it up into her hand before gently inserting Cam?s left foot and
rolling it back up his leg. Cam felt waves of intense shivers move up his
body as she finished drawing the stocking top up his thigh, and clipped it
to his front and back garters on that side. He noticed the stocking tops
were a beautiful white lace with a number of shiny clear and silver
rhinestones expertly stitched into them, and the whole stocking had a shine
to it that looked as sexy as it felt. He took the other stocking, and this
time, following her example, rolled it up himself and secured it to his
garter belt, and stood up.
Dressed in all women?s underwear too mature for even the girls his age, Cam
felt unbelievably turned on, and sexy, and mortified that he was in all
women?s underwear! As he took a few steps he felt the slight tugs on his
thighs of the straps holding his stockings up, and as his newly shaven legs
rubbed together, he felt an intense but incredible reminder of his feminine
predicament.
In this time, Maddie had put on her own belt and stockings, and looked at
Cam like a mirror image in all lacy black. "Sit down," she said again, and
pushed him gently to the bed. She entered her closet, and returned with a
pair of 4 inch bright white pumps, each with double crossing straps and
adorable buckles at the ankle. She took his newly stocking-draped feet and
slid each one into the high heels, making sure the strap was secure and the
fit was right. They fit perfectly.
Cam stood and nearly fell, but after a few steps started to regain his
balance and walk in the heels. Maddie chuckled as he moved so inelegantly,
but they could iron that out with time. She retrieved his and her dresses
and laid his down next to him. His dress was, not unexpectedly, bright
white, with halter straps reaching up from a sweetheart neck beaded at the
hem with silver and translucent rhinestones. The skirt was a bodycon mini
style down to his very upper thigh, where it became a small tutu reaching
out in all directions. As he struggled to slip it on, Cam noticed the tight
dress holding his legs closer together, and cupping his (almost) bare ass
in a way no boy?s clothing ever did. He felt constricted, and exposed, and
yet he almost didn?t care, because all he wanted to notice was Maddie, who
put on her red satin minidress which shined in just the hottest way
imaginable.
"Normally," said Maddie, I?d do your makeup first, especially because
you?re wearing white. But this time, something felt better about doing it
last. Come on up!" She beckoned to the vanity, and as he approached,
visions of his past encounter suddenly filled his mind, the way the girls
swarmed on him with makeup, and he stopped in his tracks, almost unaware of
it.
"Hey, come on...you look great! She coaxed. He slowly began moving again,
and got his first glance in the mirror. He couldn?t believe what he saw.
There in front of him, below the neck, was a beautiful girl, one he would
be unambiguously attracted to if he saw anywhere else. She wore a sexy
short dress and high stockings, the tops of which were almost fully
visible, not reaching high enough to be concealed by the very short skirt.
He sat down and looked at his face, stilly fully masculine (at least to the
extent it was when he came in). The juxtaposition was glaring.
Maddie came up from behind him, and reaching over his body, one arm on each
side, she clipped a small white barrette in his hair, pushing his blonde
bangs out of the way. Rather than a wig or extensions, she saw a way to
ease his medium length blonde locks into a feminine style by pulling it all
back and sweeping it over the top, and though it was shorter than most
girls, the style she managed with a few bobby pins and some hairspray was
no different than a short-haired girl might wear it. There was something
almost more feminine about the pixy style that Maddie really liked.
"Give me your hands," she said, and guided his hands in front of him,
laying his palms down on the vanity. She began to apply white nail polish
to each of his fingernails, except his ring fingers, on which she applied a
glittery silver. She finished with a top coat to give the shine she wanted,
and told Cam to keep his hands there while they dried. That gave her all
the time she needed to do his makeup.
She started with a pale foundation to match his fair skin, and set it with
a powder to eliminate any shine. Cam knew she was a face makeup expert, and
while she skipped a few steps she might take for herself, Cam already began
to look more feminine. A few strokes of bronzer to contour his cheekbones
and chin gave his face a more girly shape, and finally she could begin on
his eyes. After priming, Maddie started at the inner part of Cam?s eyelids
and worked out, beginning with a very light shimmery silver and becoming a
slightly darker grey. On the very inner corner of each eye she applied a
super white eyeliner pencil and covered it with a small dab of silver
glitter. She turned to eyeliner next, and drew a solid black line on each
of his upper eyelids, reaching out to a very cute double wing at each end.
She curled his lashes next, and then applied mascara, and Cam did his best
to stay still as she applied the deep black liquid, slowly transforming his
subtle blond eyelashes into bold, beautiful black lashes. Cam looked
stunning.
Finally, she turned him around away from the mirror towards her, and she
took out his final makeup item, a brilliant red lipstick that he noticed
she was wearing herself.
"Even an angel needs a pop of color," she said matter-of-factly. As she
unsheathed the tube and watched as she drew it upwards, he shuddered with
fear and delight. She slowly brought the silver tube up to his lips, and he
stared into her beautiful eyes as he felt her slowly and gently apply the
brilliant red back and forth across his upper, then lower lips. She covered
the tube, pleased with her work, and before Cam could begin to turn toward
the mirror she caressed his neck in her left hand and the back of his head
in her right as she brought her lips onto his, pressing in a deep kiss Cam
wasn?t ready for. She pulled away like nothing happened.
"Sorry Cami, you just look so damn cute I couldn?t help myself!" She said.
"Cami," was stunned. He felt what only some girls, and far fewer boys ever
did ? a lipstick-on-lipstick kiss, and with the girl of his dreams. Best,
or worst, of all ? it was his first real kiss ever. He?d remember Maddie
and this moment for the rest of his life, although he?d have to remember
also being dressed completely as a girl while it happened.
Cam silently turned back to the mirror to see Maddie?s work, and he was in
utter disbelief. Looking back at him was not the boy that walked into
Maddie?s room, but a stunning girl with an uncanny resemblance to that boy,
if someone really cared to look. His red lips broke out of a sea of white
and silver, from his nails to his eyes to his heels, and the girl in the
mirror gasped, incredulous at how she came out. "She," turned to Maddie,
who was all dressed herself in her red minidress, flirtatious makeup and
black lingerie, red heels and a trickle of fake glittery red blood coming
from the corner of her mouth.
"A few last things and we?re done," she said, as she secured a headband
supporting a halo on top of his head, and clipped some hoop earrings to
each of his earlobes. Some small, fluffy angel wings were secured over his
shoulders like a backpack, and he was done. "That should do it! And look,
its right about 6:30 ? time to get going!
_ _ _ _ _
As all of the girls and their boys arrived at Margaret?s, gasps and ?ooh?s
and ?ah?s filled the air. The girls all couldn?t believe what the others
had managed to pull off with their own costumes, but more importantly with
their little partner?s. James and Bobby couldn?t help but laugh at each
other, James in the little girl?s costume Bobby picked and Bobby in the
slutty schoolgirl outfit James found. Cam stayed fairly quiet the whole
time, although he was relieved to see his outfit wasn?t the most revealing
of the group ? that was Bobby, and Dylan arguably had the worst situation
overall. Most of all, they noticed how awfully unlike themselves they
looked. Disconcertingly, if any of them saw the others at a party they
would probably think the other boy was really cute, maybe even try to talk
to her/him!
Margaret decided that they would all take a walk around the block together!
The boys dreaded going out in public, but at least it was only 7. Outside,
they were all conspicuously overdressed given that most of the neighborhood
trick or treaters were under 13, and their parents probably didn?t
appreciate the promiscuous group of 8 girls walking around their wholesome
community in those outfits. The gang met with Rachel and Emily, who
couldn?t believe what the other four had managed to do with the boys. They
returned to the house, but on the way one of the local high school senior
boys called out to Courtney.
"Hey, you guys are coming tonight right? Bring your cute friends!" That was
Jack Jackson, and Courtney responded with an affirmative "we?ll be there!"
The boys didn?t expect to go to a party and didn?t want to, but having
gotten this far there was only one way to go from here. In a few short
hours, those photos would be gone and they could stop treading in fear all
the time.
Around 10 all of them went to the party at Jack?s house, where the boys got
their first real glimpse of a wild high school party. None of them had
drank before but each had a cup of beer given to them by an upperclassman
guy. Smartly, none of them drank it ? they knew what happened to girls at
these parties and wanted no chance of being roofied and discovered for what
they really were, in the worst way possible.
The gang stayed close together, talking and counting down the hours while
the girls mingled. Dylan commented on Bobby?s hair ribbons and Bobby kept
flicking Cam?s halo even though Cam told him to stop. None of them really
knew quite what to do, but besides denying the few boys that approached
them with the most feminine "no," they could muster, the night was fairly
uneventful, much to their pleasure.
As the girls started getting ready to end their appearance, Margaret
approached Jack and pointed to the four newest girls in the room.
"Hey Jack, quick question for you, which one of those girls do you think is
the cutest?"
Jack thought about it for just a second before confidently responding "The
Angel. What?s her name?"
Margaret replied "Cami, but she doesn?t live around here so don?t try
anything. Thanks!"
All ten of the gang gathered up in a circle for Margaret to announce the
news.
"Thank you all for participating in this year?s costume competition, except
Rachel and Emily, who thought this idea was too mean. Our winner is...Team
1! Maddie and Cami!"
Maddie?s face lit up with excitement, and she turned to her feminized
little angel and planted a big kiss on his lips, which he happily
reciprocated. The others were shocked, but as he pulled away a giant
permanent smile remained on both of the couple?s faces.
That gave everyone the adieu they needed, and full clearance to head back
to Margaret?s where everyone got undressed, took off their makeup, and ate
some candy. The girl?s lingered to tell each other all of the juicy details
of how their boys handled the makeovers, while the boys got ready to go.
James approached Margaret about the pictures.
"They?re good as gone," she told him. James watched her delete the
offending images from her laptop, and phone, and took her assurance that
they weren?t to be found anywhere else, besides the boys? own phones (which
they deleted quickly and in front of one another). Margaret was mean, but
she didn?t lie, and James felt a wave of relief as their little mistake was
finally paid for, by far more than it was worth.
"Thanks for being a good sport," Margaret told him. "I know this was a
punishment but I hope it wasn?t all bad. After all, you got Courtney."
In retrospect, having Courtney as his partner really wasn?t the best thing,
but he kept his mouth shut and nodded.
The boys went home, with the events of the last day and weeks feeling more
like a bad dream than a reality. They all found bits of glitter on their
faces over the next few days because that stuff just never comes off, but
besides that it was clear in school that no one had recognized or seen
them.
To Cam?s dismay, Maddie didn?t talk to him much like he?d hoped, even
though her texted her a couple times to see if they could date for real.
She didn?t answer, until she approached him in the hall one day a few weeks
later.
"Hey," she started, looking over her shoulder to see if anyone could see or
hear her.
"Hey," responded Cam, anxiously wondering what she could be there for.
"Ummm.. well I guess I?ll cut to the chase. I had a lot of fun on Halloween
and I was wondering...would you want to do that again sometime, like, be
Cami for me? I just think you looked sooo incredible as a girl and I?ve
been thinking about it a lot and I know it?s embarrassing but...."
Cam interrupted her with a kiss she wasn?t expecting, and without saying
anything he began to walk backwards away, towards his next class.
After a few steps, he answered, "You have my number....!" and as he turned
away, shot her a wink.