By Silvy Richards
As soon as Nathan walked through the door he heard his step-mom call out
"Nathaniel William Jones come see me right away!" Nathan knew he was in
for it bigtime just by her tone. She must've heard through the grapevine
what had happened, and now he desperately hope she wasn't going to blow a
fuse like his step-aunt Sophia had. Knowing his step-mom wasn't as loud
and extravertively aggressive as her sister Sophia, he still had reason
to worry. When she disciplined, she did it with a smile on her face and
tended to be sarcastic when it came to putting someone in his or her
Three hours earlier he was at his step-cousins place and had been playing
videogames, where the loser of each game would have to do something both
risky and embarrassing. Both were thirteen and had been making silly bets
in the past, but things had started to escalate recently, and today they
both had pushed the envelope a bit too far. After losing a round of wii
tenis, Nathan sent his cousin John with a black felt marker (non-
permanent/washable) and told him to write "I was here, John" on his
older sisters leg. She had fallen asleep on the couch while watching a
movie, therefore made for an easy target.
After completing the forfeit, they continued playing and when Nathan lost
the next game, he was sent out to draw a mustache on Julies' face, who
was still on the couch sound asleep. The only difference this time was
that John had switched markers and had given Nathan one that was clearly
labeled: PERMANENT. Just as he finished the job Julie woke up... that's
when the shit hit the fan. Aunt Sophia was called in and before he knew
it, Nathan was sent home and warned that his mother was going to get wind
of this, and that he shouldn't be surprised if he got punished for his
"It never occurred to you to check the marker?!?" his step-mom calmly
asked, but Nathan knew well enough that she was really pissed and being a
smartass, like he was most of the time, wasn't good idea. Instead he just
hung his head in shame and started muttering an apology wneh his mom cut
him of by simply saying "Silence".
"I don't know if you knew, but tonight Julie was going to dress up as a
bride for Halloween. But now thanks to you and your cousin, she'll be
going as a groom instead." Upon hearing this Nathan couldn't help but
smile a bit thinking it was kinda funny when his step-mom continued. "Oh
you think that's funny? Your cousin John, guess what? He'll be the one
going dressed as a bride. They're making it part of his punishment." At
which point Nathan couldn't help but let out a partial laugh picturing
his cousin John dressed as a girl. "I'm glad you think it's funny...
guess who's going to be the flower girl?" asked his step-mom with a smirk.
"Follow me... NOW", to which she led him up the stairs to the bathroom
and told him to strip.
He knew arguing was no use so he slowly started to strip, but then stopped
when he reach his boxers.
"What did I say?"
"Aww come on mom, I'm way too old to be naked infront of you" Nathan
"Take those off right now young man. I've already seen you naked before,
and if it's because you're afraid I might notice you're still as small
down there as you were before, trust me when I say I won't be surprised.
Your father also has tiny penis. It's in the genes little guy."
Nathan did have a small cock and had always prayed in the past while
growing up that it would one day develop into a normal size.
Unfortunately for him, his prayers were never answered.
"Just as I expected" his step-mom said with a smirk as Nathan dropped his
Taking the clippers from under the sink, she quickly clipped away at his
arpitts and started working on his pubes when all of a sudden he
"Don't move. Lots of guys shave their privates. It makes them feel bigger
down there" she said with a straight face and authority.
In Nathans's case, it just confirmed the fact that his was tiny, and now
just really made things worse. It was self-evident. It meant that getting
undressed in the locker room at school for the next month or so was going
to be even more challenging then it already was.
Putting the clippers away, Mary took out a can of hair remover and
proceeded to spray her step-son's entire body, and told him to wait for
her as she left the bathroom with his clothes in tow.
Fifteen minutes later she returned to find Nathan sqirming around, almost
dancing in the tub, begging his mom to be allowed to take a shower
because his skin was really burning. After the giving the okay, Nathan
watched ALL his hair wash down the drain, and was wondering what he was
going to tell people from school if they found out. Even worse, he
could've sworn he saw something pink and frilly in his step-mom's right
hand right before he drew the shower curtains.
Nathan stood in his bedroom mentally cursing his cousin John for getting
him into this mess, when he heard his mom sing out his new designated
"Oh Nancy! Isn't there something you need to ask your sister? She just
got home. Go see her now. After that come set the table, supper's almost
Slowly walking towards Wendy's room Nathan could feel the weight of the
breast forms and the jiggle they made with each step he took. The heels he
was wearing were only two inches high and were surprisingly easy to walk
in. The one sensation he couldn't get over was the pull of the silk
stockings and garter belt he had on under his dress. The combination of
that and his now hairless state, was causing him to get excited very
easily. The tiny frilly thong wasn't helping much either, and heading to
see his step-sister, now really wasn't the time to get hard. He really
wasn't looking forward to seeing her reaction, he just knew she was going
to have a field day with this. He and his step-sister got along only so
so. Both being quite competitive and snotty in their on right, there was
a lot of friction between them.
Almost reaching the door he could hear Wendy on the phone with their
cousin Julie and from the sound of it John had just finished modeling his
new underwear. "John's even wearing the matching lingerie?!? No way?!?"
she asked in disbelief, and went into another spurt of giggles. "My mom
told me that Nathan was being punished as well and that I was soon to
find out how. Apparently the little twerp has to ask me for my help."
Hating was he was about to do, Nathan bit the bullet and approached the
door which was already open. After a few seconds of silence he heard his
step-sister say: "Ok listen I'll call you back. Okay bye."
Holding on to the bottom of his skirt he looked inside his step-sisters
room to find her facing her computer typing away. The sheer fear of it
all made his erection disappear in a flash. Letting out a pseudo cough,
Wendy turned around and said: "So what do you want... " and completely
stopped in mid-sentence. "Oh... my... God..." and stared at her little
step-brother who was dressed from head to toe in pink, and blushing as
red as a tomato.
"You're even wearing the same slip I wore with this dress" she laughed as
she got up from her computer to inspect him further. "Holy cow! She even
shaved your legs!" she said in-between giggles as she got closer and saw
that he was wearing nylons. The dress he was wearing was the flower girl's
dress she wore five years back when she was eleven. It was extremely
girly, to the point where even she had felt self conscious about wearing
it way back when. It was made of silk and was very light. She remembered
feeling naked that day when she had worn it. She could only guess the
embarrassment her step-brother was going through. Being a boy and wearing
such a dress must be a hundred times worse, especially since it was
looking like he was wearing all the underwear that went with the dress.
"Well well well, looks like someone's going to have fun trying to keep
his skirt down tonight with all that wind out there" his sister laughed
at his plight. "Those breasts look too real. Tell me mom glued those
puppies on" to which Nathan only blushed and nodded, much to Wendy's
delight. Their mother's job was selling breast forms, so access to high
quality fake boobs wasn't a problem, except for Nathan of course. He had
on occasion touched them in their box when no one was looking. But
quickly touching them and actually wearing were two totally different
experiences all together.
"Lift your arms, I want to see you armpitts" demanded his step-sister.
Sheepishly Nathan showed Wendy his bald pitts, to which she once again
went into fits of giggles. He was obeying her simply because he knew she
would find out anyway, plus he needed her help. He was afraid to ask for
it, because he knew she could be evil about it. So complying with her
every wish right now seemed to be the right approach.
"Wow! She really went all the way didn't she? Shaved legs, armpitts,
satin slip, breast forms, pretty pink bra..." smiled Wendy at a very
uncomfortable Nathan. "Now for the million dollar question: What color is
your underwear?" she asked almost mockingly with an evil smile.
The look on his face give it away, but still he managed to whisper the
word "Pink", as his face reddened uncontrollably.
"Nathan's wearing panties... Nathan's wearing panties... Nathan's wearing
panties..." Wendy started singing just like when she was a little kid and
went into teasing mode. Totally defeated, all Nathan could do was stand
there and take it. "Are they the ones I wore when I wore that dress? The
silk ones with the ruffles on the bottom?" she asked with an evil grin.
"Mom couldn't find those..." Nathan began, "So instead she gave me
another pair" not wanting to go into details he stopped there, but his
step-sister wanted none of that.
"Are they made of cotton? Or are they satiny like your slip?" Wendy
"Like the slip" he finally uttered.
Wendy just laughed and said "Too funny" and turned back towards her
computer and picked up her cell phone that was just lying on the desk.
"Did you hear all that Julie" Wendy asked into the receiver. She had
never hung up the phone and now Nathan's worries started to grow
exponentialy. "And how was the video? Tell me, can you see his face
clearly?... good, perfect."
Franticly Nathan started scanning the room for a video camera, until he
finally saw her web cam and it was aimed directly at him.
"Ok, listen, just click save." Wendy told Julie. "That way you'll have
the video my bro, just like I got the video of your bro. Okay later
Julie, I'll see you soon" his step-sister hung up the phone and turned
off her computer.
"So little step-brother of mine, I think it's time you demonstrate your
new slave status towards me, don't you think?" She was pure evil at this
point and Nathan no longer knew how to handle things.
"You're not really going to show that video to anyone right? Come on...
just tell me you're fucking with me" Nathan pleaded.
"I bet the girls you hang out with at school would just love to see it.
No?" she asked mockingly. Wendy knew she had him by the balls and just
couldn't wait to see how far she could use this against him.
"So..." she began, "If you want me to call Julie and have her delete the
video, I suggest you do what your told. Makes sense?" she asked
"What do you want me to do" he finally managed say knowing things
probably couldn't get any worse than they were already.
"First, let's see those panties." Mandy gleefully requested. "But turn
around, I want to see your backside first."
Nathan turned around and slowly raised his skirt. "Wow, even the sluty
garter belt and stockings" laughed and whistled his sister. Until finally
the pink satin thong came into view.
His step-sister almost yelled "You're wearing a thong?!? Priceless!! Now
turn around. I have to see the front" to which he did and her laughter
got even worse. Nathan just wanted to crawl into a hole and die. Finally
she gained her composure only to notice that from the looks of it, he was
also hairless down there and thought it was too good to be true. "Mom
didn't make you get rid of all you body hair did she?" she asked can't
waiting to hear his answer.
"Yes everywhere. She totally went overboard." Nathan complained.
"Ok, I'll tell you what. If you do just one more thing, I'll call our
cousin right now and have her erase the video." Wendy stated with what
appeared to be an honest face. "All you have to do is drop your panties
to your knees, and lift your dress and slip as high as possible and stay
that way for ten seconds."
Thinking this was his only way out, he reluctantly lowered his panties to
his knees and decided to throw caution into the wind and lifted both his
skirt and slip for a good ten seconds. He lifted it so high he no longer
saw his sister's face, which was a good thing he thought, because that
way he wouldn't see her reaction when she discovered how small he was.
Gritting his teeth he could hear her trying to hold back her giggles,
until finally she sang out "Smile for the camera!" *click* *click*
As fast as he could Nathan whipped his dress down just as Wendy pressed
send on her telephone. "Too late twerp, now you're really fucked. Wow,
you're really small down there, you know that right? Even shaved you're
thingy is ridiculously tiny." His sister toyed with him, knowing which
buttons to press.
Speed dialing her cousin Julie, she triumphantly ask her if she got the
pictures she just sent. "No camera tricks nothing, he's really that
small" to which Nathan heard not only his step-sister start laughing, but
his cousin Julie also over the other end. "Ok, I'll see you an about an
hour I guess. Ciao"
"You didn't tell her to delete the video" Nathan tried, hoping beyond
reason that it would help.
"You didn't really think i was going to keep my word, did you? By the
way, mom said you needed my help? What was that all about?" Wendy was
dying to know.
Remembering why he came to see her in the first place, through many
stutters and pauses, Nathan outlined what his punishment was going to be
for the next week. Besides dressing as a flower girl for Halloween, he was
going to have to stay dressed as girl for the entire weekend, which meant
keeping the breast forms on the whole time. And come Monday, he was going
to have to dress up as a girl everyday after school, and that this was
going to last until Friday. After carefully explaining this to her, he
told her with a red face that he needed some hand-me-downs. "But nothing
too girly or frilly okay...please?!? Mom said they just have to be girls
clothes" Nathan tried to be persuasively.
"But what fun would that be" his sister laughed and as she went to her
closet to see what she could torture him with. "This one's perfect, and
this one, not to mention this slinky one..." Dress after dress, a large
pile accumulated on her bed as Nathan could do nothing but cringe. All of
sudden she stopped picking dresses as a thought occurred to her. "What are
you wearing to school tomorrow? Are you still going as the guy from
Scream?" she asked with twisted hope in mind.
Both Nathan and Mindy went to the same private school. He was a junior
and she was a senior. Uniforms were mandatory everyday... except for
Halloween. It was the only day of the year when students were allowed to
show up dressed differently. Most kids just wore jeans to look cool, but
there were always the occasional nerd or two who showed up in some dorky
costume. This year Halloween fell on a Thursday so the school decided to
let the students dress up on Friday, in order to end the week in
celebration. Nathan had planned on dressing as the boogeyman from the
movie Scream. He even bought the authentic black robe and mask. Earlier
when he had learned of his punishment, he was affraid his mother was
going to send him to school dressed as a girl, so when he asked her if he
could still go as the boogeyman he was shocked to hear her say: "Ok, no
problem. Just one simple catch: the breastforms are staying on, and under
your robe... you're going to need to ask your sister for some appropriate
underwear. Don't worry she has plenty to spare, and I'm sure she'll find
some delight in helping you."
Remembering the smug smile his step-mom had when she told him this, he
had made the mistake of throwing a fit. "You can't make me wear panties
to school... or let alone these!!!..." he said as he grabbed his realistic
boobs, "...are you crazy?!?" And just as those words came out of him
mouth, he knew he was in for it now.
"Oh really? Guess what... not only will you be wearing those breast forms
with a bra and panty set to school tomorow, but you'll also be wearing a
garter belt, nylons, and heels!! And as far as you not wearing panties to
school, starting Monday right untill Friday, you WILL be wearing panties
under your uniform! And when you get home from school, you'll wear your
sisters' hand-me-downs. A solid week of this should do the trick. So as
soon as your sister gets home, I want you to go ask her for enough
underwear to last you a week, she has more than enough to spare. Plus,
ask her for a couple of outfits for this weekend to get you started. Now
get out of my sight before I make it two weeks".
"Yes I'm still going as the guy from Scream, except I sort of have to
wear..." he paused, "some of your underwear underneath. Including a
garter belt, nylons and heels" he said real fast and in a low voice
hoping she wouldn't hear.
"Wait wait, what was that? A garter belt, nylons, AND heels?!?! Too
good." his sister said approvingly. Is that it? Or is there any more good
news you need to share with me?" ask Wendy with a menacing smile.
"Well just one other thing, and I'm begging you Wendy please try to be
"What is it? And bit your tongue about the considerate part. Your ass is
grass as far as I'm concerned. With all the stupid pranks you did on me
in the past, I've got lots of making up to do. So spit it out... what's
the last thing you need to ask me?"
Taking his courage his his two hands he just blurted it out: "I need a
week supply of panties. Mom confiscated all my boxer shorts and wants me
to wear only panties for a week... including to school."
Uncontrollable laughter once again filled the room. "So you want me to be
considerate and not pick anything too frilly and embarrassing, is that
it?" she ask with a cheshire grin.
"Oh come on... don't be that way. I guessing you must have some plain
cotton ones in your drawer somewhere... that's all I'm asking" Nathan
Walking to her dresser, Wendy opened the top drawer and started selecting
the most frilliest, tiniest, most feminine panties she could find. Opting
for a small lacy white thong, similar to the one's he was currently
wearing under his dress, she started twirling them in her fingers and
said: "So wearing these under your uniform might be a little embarrassing
for you, is that what you're saying?..." Wendy asked with mock concern
and over-acted sad eyes, "... well too fucking bad! Get ready for a week
of hell twerp!"
Nathan went out trick-or-treating that night accompanied by his step-
sister Wendy, and his cousins John and Julie that night, but due to bad
weather they cut it short and ended up back at Wendy and Nathan's place
less than an hour later. It had been windy, causing both Nathan's and
John's skirts to fly. The girls just loved it. The winds were so strong
that both of them had their frilly panties on display more times than
they could count. Twenty houses down the line thunder struck. Which
prompted the rain to begin, and not just little drops either. In a matter
of minutes both John and Nathan were drenched to the bone. The girls had
brought large umbrelas just in case, but didn't allow the boys refuge
under them. Nathan's case was worse since his dress was made of baby pink
silk. Once wet, it became completely tremparent. So much to Nathan's
discomfort, everyone could effortlessly see his ligerie in all it's
detail. Much to the delight of course to the girls who giggled all the
way back home.
Since their parents had gone out to a party that night, the girls were
left in charge of the boys. It was into the basement the boys were led,
and where Nathan eventually found himself tied to a pole with his arms
secured over his head. He was still wearing his wet girly outfit, but due
to the furnace nearby; they were drying very quickly.
"So what should we do first Julie" Julie asked her cousin. After putting
a quick blindfold on Nathan, he heard them whispering and giggling at the
same time. Soon he felt his dress and slip being pulled up and
safetypinned so that his panties were in view. Slowly, little by little,
he felt his panties being pulled down and the girls laughing their asses
off as they were doing it.
"Come on please girls! Don't do this!" he begged.
"What? You mean this?" as they yanked down his panties almost completely
off, and erupted into another fit of giggles. "Aww... look at that little
peepee. I't's tiny!" teased Julie.
Suddenly the girls started whispering again and then heard what sounded
like Julie threatening John. Nathan wondered if John was also going to
get tied up, but from the sounds of it, it didn't seem to be the case.
The girls spoke louder now and were ordering him to strip. After a few
minutes of the girls imitating stripper music and laughing at the same
time, John was left wearing only a garter belt and stockings. Ordered to
his knees, the girls led him to his step-cousin who was tied to the pole.
Still blindfolded, Nathan heard Julie give John one last order: "Do it or
else..." when all of a sudden Nathan felt his cock being sucked. As soon
as it began his blindfold was removed and he looked down to see his
cousin sucking him off.
"So is John doing a good job?" asked Wendy with a smile.
"Okay this isn't funny anymore... Ohhh... please make him stop...
Ohhhh... this isn't right... Ohhhh... " Nathan tied his best to reason
with them, but girls would have none of that.
"What's wrong?.. Ohhhh.... Does it hurt?.. Ohhhh... You want him to
stop?.. Ohhhh Is that it?.. Ohhhhhh..." imitating his moans, Julie
made Wendy laugh even harder.
"Come on John... Ohhhhh... Stop it!! Ohhhhh... Look! They're
videotaping!!.. Ohhhhh.... " Nathan begged. But John continued like
he was on a mission.
"Look, I think he's going to cum" said Wendy pointing her camera.
"Ohhhh God.... Ohhhhh.... Ohhhhhh... yes..." Nathan regrettably
whispered at the end as he came in his step-cousin's mouth, much to the
delight of the girls.
With two scandalous videos hanging over Nathan's head, and with a promise
that they would both be deleted next week... if they did everything asked
of them, Nathan didn't put up much of a fight when the girls untied him
and told him to return the favor and suck his cousin off. Half way
through the blowjob, the girls whipped out a tube of KY jelly.
The girls then ordered John to fuck his Nathan.
As soon as he came, which didn't too take long, the
girls noticed Nathan had a boner from his assfucking, so they made him
The sex between the two boys went on for hours and the girls couldn't get enough of
watching them squirm with disgust, yet at the same time still manage
to get each other off. Eight ejaculations later, their parents arrived
from their party, so the girls had to call it a night and let the boys
put their dresses back on.
After that, life was never the same for Nathan and his step-sister.
Although the videos were deleted a week later, Nathan always stayed
subservient towards Wendy. She owned him for life, and he knew it.