Chris lands himself in trouble at school while his parents are away. His sister devises a suitable punishment for him, agreed to by the school.
This is my first post to BigCloset, and my first in several years. The story is several years old but never seen online in this form until now. It is inteded to end how it does, open and leaving leaving the reader wondering what comes next. Use your imagination! ~.^ -- SD
Sister's Punishment by Sissy Demi
"Ok, I will take of it … yes … no … Well, our parents are on holiday for a few
weeks and I’m in charge of him while they are away … I understand … But, you
will allow the punishment I suggested? … Great! I’m sure a week or so of it will
cure him of any more ideas like that again … OK … I will make sure he
understands, and, thank you.”
With that I hung up the phone and turned to my best friend, Gwen, a huge grin
plastered across my face. She squealed in delight, her own face sporting a grin
to match my own.
“They agreed to it?” she asked, almost quivering in glee.
I nodded solemnly. Then grinned even wider than before. We both broke into
giggles, hugging each other tight, then giggling some more.
“This is going to be great, Sarah!” Gwen gushed, her green eyes sparkling. “Your
little brother is really going to get it now!” She flipped a loose lank of her deep
auburn hair back over her shoulder, cocked her head at me and gave me a mock
stern look. “You ARE going to let me help, aren’t you?”
“Of course!” I replied, my own blue eyes glinting. “This just gives us an excuse to
pay him back for all the little pranks, gags, and embarrassments he’s given us.” I
looked at the clock on my night stand and turned back to Gwen.
“He’s going to be home in about 30 minutes or so, so why don’t you go home
real quick and get what you think will be appropriate and meet me back here.
‘K?” I stated more than asked. She giggled again and gave me another quick
hug before scampering out of my room. I heard her feet fairly skipping down the
stairs, then the door opening and slamming shut.
With a suppressed giggle of my own, I started getting things prepared.
I was sitting quietly on the couch downstairs, watching an episode of Lizzie
McGuire on Disney, when the front door opened slowly and quietly. I kept my
head facing the TV and pretended to not have noticed. A surreptitious glance
into the decorative mirror we had on either side of the television showed my
brother slowly closing the door and trying to sneak past the back of the couch
without my noticing.
His blue eyes darted nervously from where I sat to the stairs and back. He licked
his lips and ran a hand through his short, brown hair. A sure sign he was worried
or scared, that always gave him away. He took another slow step.
“Hi, Chris!” I said a little louder than needed. He started and dropped his
backpack with a thud.
“Err . . . Hi, Sarah,” he replied, swallowing hard. I still kept my gaze on the TV
screen, flicking quick glances in the mirror to see what he was doing.
“How’d school go?” I asked blandly.
“Ummm . . . y’know . . . It went like it does every day,” he stammered, running
his hand through his hair again. I suddenly angled myself on the couch to better
see him and looked directly into his eyes. I barely kept myself from smiling and
giving my little game away as I saw his eyes get a bid wider.
“So, nothing exciting happened?” I asked calmly, staring into his eyes. He licked
his lips again, started to run his hand through his hair yet again, then broke my
gaze and looked over my shoulder at the television.
“No, just the usual,” he said in a monotone.
“Really?” I asked, drawing the word out. Just then Gwen came through the front
door, lugging a small suitcase and tote bag. She started to say something, saw
Chris, and giggled, grinning. I shot her a stern glance and turned back to Chris.
He had already taken a few steps toward the stairs and looked like he was ready
“Chris, go put your stuff in your room, change out of your school clothes, and
come back down here. You have 10 minutes.” I told him, still with the stern look I
had just shot at Gwen.
“You’re not the boss of me!” he snapped, obviously deciding to play hardball
instead of the sneaking game he was playing.
“Yes. I am,” I said evenly. “Now do what I said!”
He gave me one venomous look and trudged up the stairs, muttering under his
breath. I heard his bedroom door slam and the house shook as his backpack
was thrown to the floor.
Gwen and I locked eyes.
“This is going to be soooo much fun!” I said, a slow grin forming on my face
again. She nodded, flashing me her own grin and set the bags down on the
“I brought all the old stuff I had,” she said, opening the suitcase as I began to
paw through the tote bag. “I hope everything is good. I tried to keep your plan in
“These are great!” I told her. “Let’s get this up to my room and I’ll show you what
I have.” She nodded enthusiastically, and we bounded up the stairs into my
Ten minutes later, Gwen and I were standing in front of the couch in living room,
waiting for Chris. I was so excited. I could hardly contain myself. Gwen was as
bad as I was. She kept stifling giggles and grinning.
I glanced at the wall clock. Twelve minutes since I sent my brother upstairs. I
“Chris!” I yelled up the stairs. “Get down here NOW!”
A half minute later he came trudging down the stairs, glaring at me and Gwen. I
pointed at the couch and told him to sit down. He walked around the couch and
flung himself into an easy chair in defiance. His sat with his legs over one arm,
and had his own arms crossed in front of him, glaring at me.
I decided not to push the issue of his defiance or his two-minute lateness. I
crossed my own arms, Gwen following suit, and we glared down at him.
“I got a call from the principal today,” I started. “He had some very interesting
things to say.”
“I bet,” Chris muttered, his defiant gaze faltering for a second.
“We discussed the situation for a while and I informed him I would take care of
it.” Chris snorted at this. “I also talked him out of suspending you, which would
likely have ended up as expulsion in light of your past deeds.”
“Yeah, so?” He growled, but I could see the hitch in his throat and the fear of
what would happen if he had been suspended. Mom and Dad had been quite
clear that he was to stay out of trouble while they were gone and that I was in
charge, no matter what he felt.
“Well, Chris, can you tell me why you broke into the girl’s locker room?” I was
peering intently at him, now. Gwen had moved to sit at the edge of the couch,
leaning forward to stare at him, too.
“Yeah, Chris, why?” she asked.
“What’s it to you?” he snapped his head around to face Gwen. I suppose he
thought he could bully her since he didn’t seem to be getting anywhere with me
using his bad attitude. “You don’t need to be here, anyway. You’re not part of my
“No, but she is my best friend and offered to help me watch you while Mom and
Dad were away,” I told him. “And, as far as I’m concerned, after today’s stunt you
need both of us looking after you.”
Chris narrowed his eyes at me, and shook his head. Before he could say
anything else, I went on.
“And, my dear brother, can you tell me why you had three pairs of panties stuffed
in your pocket when the girl’s gym teacher caught you?” His face blushed red as
a stoplight as I asked this. He stammered something about because he thought
it’d be cool to steal them and show his friends.
“Maybe,” I smirked at him. “But, I have come up with a punishment for you in lieu
of your not being suspended. The principal has already agreed to it, as well.”
“Just because you’re almost 18 and I’m 15 doesn’t mean you can punish me,
Sarah!” Chris spat at me, his face changing from the red of embarrassment to
the flush of anger. “Ever since you became a senior and got first session at
school you have been bossing me around when I get home. Not this time, you
hear!” He stood up, fists clenched at his side, trying to intimidate me.
He was almost the same size as me, just a tad shorter in height and a tad bigger
in his legs, shoulders, and arms. He was not really small for his age or sex, as
much as he thought, but he wasn’t as big as he saw himself, either. I pushed him
back into the chair with one finger.
“While our parents are out of the country, little boy, I am in charge!” I growled,
having gotten my dander up. He sat glaring up at me.
“I’m still not doing whatever this so-called punishment is,” he flatly told me.
“Oh, yes,” I replied, “You will. That is, unless you want the principal to go ahead
and suspend you, maybe expel you, and get the school cop involved. It was
basically breaking and entering and theft you did, you know. And, I know you
don’t want to go back to juvie until Mom and Dad get back. Remember the last
time?” I arched an eyebrow at him.
For his part, Chris stayed quiet, if still belligerent in his looks. He knew as well as
I did that if he went back to the juvenile center, he’d be thrashed again. Not so
much for his size, but for his mouth. This was a threat our parents and the police
always held over his head to keep him in line, though I’m sure they’d make sure
he wasn’t hurt again if he did go back.
“Are you ready to listen to your punishment, Chris?” I asked. He stayed silent,
trying to bore a hole through my head with his burning eyes. Gwen giggled again,
the first sound she had made since he went off on me. She got a quick black
look from Chris in return.
“Well, I decided since you seem to like girls’ clothing so much, that you shouldn’t
have to resort to stealing them to enjoy them. So Gwen and I have gotten some
of our old outfits together for you,” I was smirking heavily as I said this
“Very freaking funny, Sarah,” he snarled. “Seriously, what do I have to do? Wash
the johns at school? Clean the whiteboards? Help in the cafeteria? Paint the
“I’m serious, Chris.” I nodded to Gwen who got up and ran up the stairs. I
reached out and grabbed my brother by the upper arm, pulling him up, and
guiding him toward the stairs. He didn’t resist much, trying to decide whether this
was a joke or not.
“I’m not letting you make me look like a girl, Sarah. Besides, the school wouldn’t
allow it,” he said evenly, testing to see if I was playing an awful prank on him.
“Chris,” I sighed, “I promise I won’t make you look like a girl, ok? And, the school
already agreed with my choice of punishment.” By this time we were halfway up
the stairs and he started to really believe I was joking and relaxed a little,
allowing me to lead him to the partially closed door of my room.
I stopped us in front of the door and put my hand lightly on it, turning my head to
look Chris in the eyes. He had this slightly dazed and bewildered look as if
wondering just why we were going into my bedroom. I gave a light shove to the
door, and it obligingly swung open to reveal Gwen standing to one side of the
bed, her arms outstretched like some game show girl, a wide grin splitting her
On the bed was an old outfit of mine. Very cute, very girlish. Very much for Chris.
He spun in my grasp, eyes wide.
“I thought you were joking, Sarah! You said you wouldn’t make me look like a
“I’m not joking in the slightest, Chris,” I said, dragging him into my room and
standing him in front of the bed. His eyes locked on the pastel outfit displayed
before him. “I promised I wouldn’t make you look like a girl, and I won’t. You are
going to look just like the boy you are, only wearing girls’ clothes.”
He started shaking a bit then, his eyes a bit more glazed looking. I expected a
fight from him, but I think he was so shocked at what was happening he couldn’t
fight back. I nodded to Gwen and she came to stand on the other side of my
“Let’s get you changed, Chris,” I said. He didn’t really acknowledge me, just
stood mutely staring at the clothes on my bed.
“I think you’re going to look so adorable, Chris!” Gwen said a bit breathy. I gave
her a quizzical look but she was just looking from Chris to the outfit and back, a
small smile playing around her lips and a strange look in her eye.
I had always suspected she had a slight crush on my brother, but was
embarrassed to say anything because she was 17 and he was just 15. In all
honesty, he was a cute boy, and could be a pleasant person when he wanted to
be. But it seemed the idea of seeing him in her and my clothes sparked a real
interest in him now.
I smiled to myself and thought it would be interesting to see how everything
“C’mon, Chris, get your clothes off,” I nudged him.
He was a bit slow in taking his T-shirt off, and Gwen reached up to help pull it
over his head. Then she started to pull his shorts down and Chris seemed to
snap out of his daze a little, grabbing her hands in his and shaking his head.
Gwen slipped her hands free, replacing them on top of his, and slowly began
tugging down again.
“It’s ok, Chris. It’ll be ok,” she said, her big green eyes gazing into his blue ones,
a sweet smile splayed across her lips. I don’t even know if she remembered I
was in the room with them. Very interesting, I thought. Chris allowed her to slip
his shorts down and stepped out of them.
He was barefoot, and stood looking into Gwen’s eyes as if seeing her for the first
time. She moved her hands to lower his briefs, her eyes flicking down to his
boyish bulge in front. Chris hesitated a moment and let her slip those off, too.
Gwen glanced down at his private parts, and her lips parted in another smile,
then looked back into his eyes. I was just going to make him change his
underwear in the bathroom, but Gwen seemed to have other ideas. Since Chris
was complying without a fight, staring into her eyes, I was not about to argue.
Though I now found the whole situation even more amusing than I originally
I quickly snatched a pair of satiny pink panties, an unworn gift from one of my
more excessive boyfriends, and pressed them into Gwen’s hand. She
instinctively closed her hand on them, which temporarily broke whatever spell
was woven between her and my brother. She glanced down at the panties, then
up to me, her smile widening from the soft, sweet one she had bestowed,
unknowingly I think, upon my brother.
“Sarah,” she said, still a bit breathy, “This is sooo cool.”
I smiled as she looked back to Chris, who was still searching her face with his
eyes. Gwen seemed to have shaken off her brief phase of being “love stricken”,
as she teasingly held the panties up in front of Chris’ face.
They were bikini style with a small bit of off-white lace around the legs and
waistband. It was made from a slightly stretchable, yet satiny, pale pink
nylon/Lycra fabric. The panties shimmered in the overhead light as Gwen
danced them in front of Chris’ eyes. He was slowly coming out of his swoon, too
and began to get that look of fear in his eyes again.
Gwen bent down to help Chris into the feminine panties. He looked down and
opened his mouth to say something, a blush forming on his cheeks, when his
eyes seemed to dive right into Gwen’s cleavage formed by her low v-necked
halter. Again, his eyes softened, and he lifted one foot, then other, and placed
them into the holes of the panties pooled about his feet.
I don’t think Gwen noticed him staring at her breasts as she slowly slid the
slippery fabric up his legs and around his waist. She seemed intent as she
straightened the waistband and legs so the lace bands were smooth and flat
against his skin. Again, her eyes lingered on the un-girlish bulge in the front of
the shiny pink panties. One of her hands started to move toward his groin
hesitantly, as if wanting to stroke the soft fabric, but stopped just shy.
She tilted her up, caught Chris’ gaze into her cleavage, then cocked her head to
the side and smiled at him.
“I knew you’d look adorable,” she told him. Chris faltered a smile at her, his eyes
moving upwards again to hers. “A cute little sissy boy.” She said, the smile gone
from her lips, but still dancing in her mischievous green eyes. Chris’ smile also
failed and the look of terror crept back in.
I wondered to myself if I should say something to Gwen about her actions, then
decided to do it later. She grinned at him and giggled, forcing him to blush
again. I decided to make Chris aware I was still in the room, too.
“Yes, Chris, a cute sissy boy in pretty pink panties,” I said, my words dripping
honey. “But, we have even more sweet things for our little boy-girl to wear.” I
motioned to the bed where the rest of his outfit lay.
I grabbed a pair of capris from the bed and held them out to Chris. He hesitated
then took them, his eyes locked onto them as if they would bite.
The capris were made from a soft cotton and were patterned with a pastel pink
and pistachio green plaid. He moved his gaze from the cute capris to me and I
sternly told him to put them on. Chris fumbled with them and raised one leg to
start putting them on.
“No, silly,” I said, stopping him. “The zipper goes in the back.”
Gwen laughed softly, eliciting a chuckle from me as Chris spun the capris around
and stepped into them, pulling them up. He fumbled with the rear zipper and
Gwen (of course, teehee) moved to help, straightening the waistband and pulling
the zipper all the way closed.
The effect was even better than I hoped. The pastel plaid capris clung to his legs
snugly, but not tightly. They ended about six inches below his knees with small
side slits. The waist was one of those no-waist styles, so there was no elastic
band and they rode a bit high on him. The best part was the smooth front.
Well, almost smooth front. There would be no mistaking Chris for a girl with the
bulge showing nicely on the smooth paneled front of the capris.
Gwen and I exchanged quick looks and smiled. Though I detected a bit more of
an interest in my brother in her eyes than before.
Next we slipped a slightly deeper, brighter pink tank top over his head. I let Gwen
make sure it was on him properly, as she seemed to be enjoying on more levels
than I had anticipated. The tank was a soft flat ribbed cotton which laid quite
nicely on his torso. The straps were about an inch wide, with a low scooped front
that would have shown cleavage on a real girl but only emphasized his lack of
Over this was placed a cardigan, of sorts, of a matching green color to the
capris. It, too, was of a cotton type fabric, clinging to him with just a bit less
snugness than the pink tank top. The sleeves were 3/4, ending slightly past his
elbows. Instead of buttoning the length of the front, a single gold clasp held the
cardigan closed at breast level on a girl.
We stood back a moment to look at Chris, who was starting to sniffle at the
realization this was definitely no joke and I was serious.
He was absolutely cute, in a sissyish sort of way. There was no denying he was
a boy with his short hair, flat chest, straight lines, and, of course, the boyish
bulge Gwen’s eyes kept sneaking peeks at. But, no boy would ever be caught
dead in this outfit of soft pastels and cropped styles.
We moved him to the bed and sat him down, each taking a foot and slipping pale
pink turndown socks on his feet, followed by a pair of my white and pink
accented sneakers. As a final touch, Gwen placed two pink barrettes on the left
side of his head, holding back that portion of his hair from his forehead, and we
Woodenly, Chris followed our prompts and was soon standing in front of my full
length mirror, and looking at the girlishly clad boy staring back at him. He was
slightly trembling, and his eyes were roving back and forth from his image to our
own reflections standing close behind him to either side.
“Don’t you think you like cute and sweet, Chris?” I asked softly. His gaze shifted
to mine and hardened.
“OK, you’ve had your fun, now let me get changed,” he said in softer tone than I
would have expected. Still dazed from it all, and especially Gwen’s reactions, I
“I thought I made myself clear, Chris,” I admonished him. “You’ll be dressed in
clothing like this for the next week or so. You wanted to steal girls’ things so
much, I think you should have the opportunity to experience them without
resorting to theft.”
“Fine,” he heaved a deep sigh. “I will put on whatever sissy stuff you say as soon
as I get home from school.” His lips twisted in bitter acceptance of his supposed
fate. He still didn’t understand.
“Not quite, my girl-clad boy,” I chuckled in his ear. “You see, I made arrangements
with the principle for you to wear your new clothes to school in exchange for
leniency on the suspension. We felt it would be a good experience for you to deal
with the snickers, laughs, and embarrassment you have caused so many others
since you’ve been a freshman.”
Chris’ eyes widened and his jaw dropped.
“I . . . I’ll get creamed!” he stammered.
“No you won’t,” I said smugly. “Gwen and I will protect you, and we will get the
word out that anyone who messes with my sissy brother will answer to me and my
friends. Gwen’s new class load starts tomorrow, so she’ll be on the same late
session as you. She will come over and help you get appropriately dressed and
get you to school. This way you won’t be able to skip, either.”
Gwen was grinning from ear to ear and reached down to squeeze Chris’ clenched
“Don’t worry, my sweet sissy boy,” she gushed into his ear, “I’ll help you however I
can to be the most adorable, sweet, and cute girly-boy at school! And, wherever
else we may go, too!”
Chris gulped and looked like he was about to faint.
I stepped back from behind him, and clapped both Chris and Gwen on the
shoulder in a friendly manner.
“So, how about some food?” I asked brightly.
Gwen nodded enthusiastically, and even Chris shrugged. His shoulders, encased
in the pistachio green cardigan, slumped in defeat.
“Great!” I said, looking at the bedside clock. “It’s a little late to really cook
anything. How about we hit the pizza place for a few slices?”
Chris stumbled in sudden fear of going outside like this, really hitting for the first
time. Gwen caught him and answered for both of them.
“Sounds fantastic, Sarah! And, I have the perfect lipstick to go with his outfit, too!”
She giggled and we led him down the stairs and out the front door . . . .
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