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
to bolt.
“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
couch.
“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
mind.”
“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
bedroom.
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
sighed.
“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
family!”
“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
sarcastically.
“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
house? What?”
“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
face.
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
girl!”
“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
brother.
“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
played out.
“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
expected.
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
breasts.
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
were complete.
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
thought.
“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
fist.
“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 . . . .
by Sissy Demi
I am reposting my original series of BLSB (Bad Little School-boy) cartoons I began creating back in the early 1990's. This is not the Illustrated Story, but the original, one-shot, one-panel cartoons which were an unofficial pre-cursor to the actual written tale which may be coming soon.
Each image is presented in its original style and artwork. Only the file naming and image type have changed.
This is the second part of the original BLSB cartoon series. As with most of my creative works, I did it mainly for myself. Hence, the first image involved a pair of shortalls. At the time I was deeply enamored of shortalls. They screamed girlish to me. I would daydream of wearing some with a cute top and going out with my wife (who knew of and enjoyed my crossdressing). Unfortunately, I never did own a shortall set.
I did, however, own a few outfits very much like our favorite bad little school-boy is wearing in this cartoon. Teal was my favorite color then. And I owned a nice, tunic-length soft cotton sweater with a mock turtle neck and long sleeves that billowed out slighty at the gathered wrist. I also owned several pairs of leggings, both stirrup and ankle length. I really enjoyed the snug feeling of a pair of soft, comfortable leggings paired with a long sweater. I felt very cute and girlish in those outfits. Like Chris, I would often wear matching socks over the leggings and sneakers. Sometimes a pair of cute ankle boots I had.
I miss those days.
One of the very first article of girls' clothing I have vivid memories of wearing is a girl's one-piece swimsuit. I was around 7 or 8, at the time. My older sister had friends who came over almost everyday to swim in our pool, and one of them used to leave her suit over to dry in our bathroom for the next visit. I used to sneak it on when I was supposed to be taking my bath.
The suit was a one-piece tank style with a criss-crossing strappy back, blue with pink, yellow, and green florals scattered across the material. The shoulder straps were pale green, much like a scrunchy looks slightly stretched. It had somewhat high-cut legs with a matching green ruffle around the leg holes and two rows across the butt. It fit me like a second skin and I loved it.
I've worn others in my life, but this has always been my favorite. My first wife (who also knew and played dress-up with me) owned a suit very similar in color and pattern, but lacking the ruffles and with open sides attached together by greenish strips of material. Once, after losing one of our numerous bets, she made me wear it to the apartment complex pool on a weekend evening. A few people were there and I was subjected to to good-natured ribbing and comments (mostly of the "he has great legs" variety). Though the males there joined in the teasing, I could tell they were uncomfortable and maybe even slightly angry to see me sporting about the pool in a woman's bathing suit with my wife.
We stayed until very late, and after everyone left. My wife took full advantage of my arousal at wearing the suit and being embarrassed by the prior teasing. It was the first of many times we played that particular game.
Swimming now just is not the same. ~.^
The next few images were done as exclusives for Crystal's Storysite back in ... well, I don't really recall what year it was, but it was a long time ago. ^^
You almost cannot have an anime/manga style cartoon character without putting them into a fuku at some point. Now it was Chris' turn. He doesn't seem to be enjoying it ... much.
I never wore a traditional fuku, but growing up, my sister owned a very cute sailor outfit which was eerily close to what Chris is wearing. The sleeves were short and banded, and the collar was slightly bigger. The skirt was knee length, in keeping with my mother religious views, imposed by the church, on modesty. My sister hated the outfit and rarely wore it unless forced to by my mom.
The first time I wore it, I too was forced.
I was around 10-years-old to her 13 at the time. She and our step-brother were picking on me, as usual, when I made the mistake of fighting back. Their typical "punishment" was to sit atop me and tickle me until I could blow a raspberry. Do you know how hard it is to go "Pblllllltttt" while laughing hysterically and squirming violently to avoid semi-painful tickling under your sensitive armpits? Twice, they had stripped me down and tossed me out the front door. Fortunately, our house was set back off the road at an angle and we had a deep covered portico leading to the front door. Once before they had dressed me in one of my sister's jumpsuits, an orange affair that, upon reflection, looked more like a prison uniform than a young girl's outfit.
But this time, my sister decided I was going to wear her sailor suit. After I couldn't make the requisite raspberry, they dragged me up and marched me into her room. In short order I was dressed in the, to me, cute outfit. I acted like I didn't want to, but I really was loving it, in a scared-to-death yet thrilled-to-the-core sort of way.
A big blue bow was pinned to the top of my head and a pair of too-big white flats were slipped on my feet. I was then marched out the front door and told the only way I was getting back in the house, or change out of the clothes, was to walk down to a neighbor's house and back. It wasn't awfully far, a mere six houses down and back, but it was a late weekend afternoon and several people were out in their yards, including a neighbor boy who I always had squabbles with.
I made the long walk, and even though my knees were wobbly and body trembling, I was very, very aroused. It was good luck the skirt was so full and my preferred underwear were tighty whities, keeping everything in relative check. If the neighbors doing yard work noticed, they never said anything. My local nemesis saw, and he hooted and hollered as I passed, but he oddly never brought it up to me again.
I survived that experience, and I believe it settled in me the desire to be forcibly dressed and humiliated in public. I also wore the sailor outfit several times more, often by myself when no one was around, but a few times as part of a Truth or Dare game I devised to play with my friends. I often manipulated them into making me dress up in my sister's or mom's clothes.
I also think that experience is why I have such a soft spot for anime, as fukus are seemingly intrinsic to the genre.
Unlike my previous images, I've never worn anything like Chris wears in this one.
About the closest I have come to it is a Wonder Woman costume I tried on as a dare. This was back when I was 17, and my girlfriend at the time was unaware of my crossdressing. At least, unaware I enjoyed it and lost bets to her in the hopes of being made to do it. Which happened on several occasions. She was into The Rocky Horror Picture Show, having a huge crush on Dr. Frankenfurter. We went to midnight showings of it nearly every weekend ... but that is another story.
I admit to getting hooked on Sailor Moon when it was very popular in the US with pre-teen girls. My girlfriend's daughters watched it everyday and I got sucked in. In a large part the show contributed to me wanting to make the two part cartoon of the fuku and Sailor Moon costume. Sailor Jupiter was my favorite Scout, and I even have images of Chris wearing Sailor Jupiter's normal and scout outfits. Though they are simple images only, not done in the BLSB cartoon style.
Ever since watching Sailor Moon I have had a soft spot for the whole Magical Girl genre of anime and manga. If you can find it, there is a manga series called Broken Blood which involves a boy who becomes a Magical Girl and fights crime ... though he does not transform into a female, he is just dressed as one. He also is dressed as a normal girl many times, too. I've only seen the first book of the series, and it was untranslated. I'd love to read the entire translated series, though. It looks very fun.
This cartoon came about after my girlfriend brought home a maids outfit from the hotel she was working at. I had "lost" one of our ubiquitous bets and she claimed me as her sissy maid for the weekend. This was not the first time she made me be her sissy maid, but it was the first time with an actual uniform. Previous, she had dressed me in a black, long sleeved leotard over white tights with a fluffy, white bib apron atop that. Oh, and 3-inch heeled black pumps. And a big, white bow in my hair.
This new outfit was not the "traditional" French maid uniform. I've never worn one, but would have liked to. *sigh*
No, this one was a drab, gray affair. It was knee length, with short, white cuffed sleeves, a white collar, and double breasted buttons. She also found a simple waist tied apron to complete the ensemble. I wore the white tights as usual, though this time she made me wear a pair of chunky heeled, square-toed loafer type of shoes. I've no clue where she got those as I never saw them before then. Topping it off was a little frilly white headband ... another new item I never saw before. Unlike other times, she did not put make-up on me other than a dark plum lipstick, and my underclothes were plain white and boring. My hair was also left in my normal boy-style.
She took to calling me Drudge that weekend. I did all the usual house cleaning duties (which we pretty much shared at other times), and each task completed to her satisfaction earned me a reward. The rewards were small things like a quick kiss, a pinch on the butt, a whispered tease in my ear, and the occasional caress to keep me ... errr ... attentive. I knew a greater reward was coming, as all our games tended to end with. But first I had a task I was unprepared for ...
She decided that we were going to do the laundry, as well. At the Laundromat. o.O
Now, I was no beginner at going out dressed, even as an obvious male in women's clothing. (That actually turned me on!) And I also was no Shrinking Violet when it came to embarrassing outfits and public exposure. But my ever-lovin' girlfriend decided not only were we going to the corner Laundromat, but that I was going sans panties!
It was a tense experience for me, and her little tricks to tease and entice me while I endured the stares, comments, and open hostility some patrons shot my way kept me fighting for control of my nether regions. My girlfriend made it clear to everyone I was working off a bet to her. Some people chuckled, a few shook their heads smiling, most were not amused.
It was a harrowing, exciting, and thoroughly draining experience.
I couldn't wait for a repeat!
Poor Chris, on the other hand, just wouldn't have felt right in a maids uniform at school. Thus the idea of one of those tacky nylon affairs stereotypically worn by lunch counter waitresses and lunch room attendants. I'm not sure Chris enjoyed his time as a drudge as much as I did mine. ~.^
This is one of my favorite BLSB images. I adore this outfit. I imagined wearing it myself at that age as I drew and colored it. Soft velour capris, in the style of more current track suit outfits worn by girl's nowadays. A matching soft, brushed cotton top with an airbrushed flower and ruched, tied side. Cute little pink-accented trainers. I go all tingly just imagining it.
I love capris. I cannot imagine a more feminine pant style. You never see boys wearing them, although some of those baggy shorts come close! ^^ Much focus is given to dresses and skirts in crossdressing fiction, but feminine pants are even more of a turn-on to me. Capris, gauchos, cropped styles, wide-legged, leggings, and all the accents on jeans like embroidery, fringe, lacing and even the very fabrics used in them. For a long while I was in love with skorts, too. And, I still miss the short lived skegging fad of the early 90's.
The image is also much more recent that the previous six. I suppose, technically, this wouldn't be part of the Original Series. Those were done before and during the time I created the Illustrated Story. This was much after. "In the Pink" was created and posted on Betty's Sissy Site a while back ... the date on the image properties list it as January, 2005.
It was done with much better technology, and a smattering of more experience, reflected in the increased color palette (16 millions colors), png file format (the others were gif, posted here as png), and the use of layers, shading, and anti-aliasing techniques. I did keep the same base doll, frame, and logos, however. Sort of a retro BLSB meets modern BLSB.
The outfit is also a more "real world" style of outfit. Less of a costume than most of the previous six. I will be posting the Holiday Wishes Series and the Postcards from the Edge Series sometime soon.
This is another of the newer cartoons I posted to Betty's Sissy Site forums a couple years back. I recycled the main image recently in a new image in my blog. This was before I found several of my "lost" images on a thumb drive.
When I drew this particular cartoon, I had a little story percolating in the back of my mind. The chill of Winter has ended. The bright explosion of Spring's multi-hued blossoming has begun. Warm weather, gentle breezes, birds singing, the smell of Earth renewing herself. Sissies being sent out to play in cute outfits and bright lipstick and nail polish.
Okay, maybe that last part isn't a Rite of Spring, but poor Chris simply cannot show himself to the other guys out at the basketball courts like this. Can he? Jump shots in jelly sandals and dribbling with acrylic nails would be difficult. Not to mention his light makeup would run if he got all sweaty. And every time he raised his arms over his head to shoot, the bra straps pinched ever so slightly.
I guess our Spring Sissy will just have to cheer his former buddies on from the sidelines.
I posted this in my blog before I was talked into reposting my works in the main fiction section. The original of this image was done similar to the early 246 color gif images. This go-round I upped the colors to 16 million, added some shading to the outfit, redid the text and title, and used png as it retains image quality better than jpg for high colors.
I'd love to wear an outfit like this as a costume. The closest I've come is a few gowns my sister and mom had and an Easter outfit ... but that one is a whole other story. ^^;;; I've also worn bloomers once. They were ankle length and ruffled, made of a thick white satin. Yes, they were the inspiration for Chris' bloomers in the pic above.
This is another older image, original this time, which was posted to Betty's Sissy Site. There had been a thread about chili (for some strange reason), and this was my contribution. It was one of the first times I had sampled a texture into the art to give a denim look to the skirt and vest. I also was happy with the cowgirl boots.
I love boots. Fall and Winter are my favorite time of year because so much of my favorite clothing is worn then, especially boots! Western wear is not a top favorite with me, but I do like the look and I used to look fabulous in southwest style clothing, if I say so myself. ^^;;
My very first pair of boots were given to me by my first wife while we were still dating. They were her brown suede moccasin boots which laced up the front to just below the knee. She wanted me to wear them with her calf length brown corduroy skirt and a black, long-sleeved cotton knit top with a fancy high neckline. She gussied the whole thing up with some turqouise jewelry (clip-on earrings, a dangly necklace, and bracelet) and a copper concho belt. My hair was teased into a poofy style and topped with a brown, felt cowgirl hat. No make-up save for a very light pink, shimmery lip-gloss.
Then she took me to a local mall.
It was one of my very first times out in public, full daylight. I was excited, aroused, and utterly terrified. I was read . . . a lot! Worse, as we ventured into a few stores, she made no bones that I was her boyfriend and that she was looking for a hair accessory for me in Claire's, short-heel ankle boots in Payless, and "something soft and sweet" at Victoria's Secret.
Most of the salesgirls laughed and grinned and happily helped her find the perfect items for me. Many asked if it was a dare, to which my ever-lovin' soon-to-be-wife replied, "No, I just like him in my clothes." I almost fainted then.
I wound up wearing a denim headband and black suede ankle boots out of the mall, and toting a new white satin nightie in a very obvious Victoria's Secret bag.
Ah, bliss. ^^
-- SD
This is the last of the Original Series that I still have, not including the Holiday Greetings and Postcards. Those will be coming soon.
Again, this was posted to Betty's Sissy Site, and was created in response to a brief discussion of sissys around the world and an even briefer conversation of how the Northern and Southern Hemispheres differ in their respective seasons. While it is Summer in the Northern Hemisphere, it is Winter in the Southern.
This was my second attempt at utilizing a texture to achieve a particular look for the clothing. This time it was velvet. I really liked how it came out and is one of my favorite outfits I have drawn Chris in. The kangaroo cracks me up, too. I like how his shading came out.
Those of you with LCD, flat-panel screens may have to adjust your monitor for the best view as I've been notified by several viewers the black-on-black color scheme can be difficult to see. Either Adjust the Gamma, or tilt the screen, or even scooch down in your chair. ^^;;;
I adore velvet clothing. Velvet is so soft, so sensual, so elegant.
Before my first wife and I were married, and shortly after I confessed to her I enjoyed crossdressing (and her reply of already knowing and liking the idea), she dressed me up in a deep, emerald green velvet dress. It was the very first outfit of hers she made me wear.
The dress was form fitting, princess seamed with long ruched sleeves, a rounded neckline, corset ties in the back, and a knee-length, flowing skirt. She added a pair of black flats, white crotchless pantyhose, a triple strand pearl cuff bracelet with matching choker, dangly clip on drop pearl earrings, and a frothy white bow in my boyish hair. No makeup except red lipstick. She was visibly excited, and later told me she loved the feeling of "making" me wear her clothes and of how I looked ... the whole obvious boy in girl's clothing turned her on.
Me, too.
Some heavy petting followed. Whispered teasing of "my sissy boy", comments of how adorable or cute I was, and other, less G-Rated scenarios were breathed into my ears as our hands roamed freely. She had me try on three other outfits before we wound up in lingerie under the cool sheets of her bed and made love for the first time.
We did not always include dressing as part of our love-play thereafter, but it was more often than not. and in ways and places I cannot express in this All Ages post. ~.^
Velvet earned a special place in my heart that evening, along with being teased and mild domination. To this day I am still not sure who used each other more over the years. Her for her latent lesbian fantasies and desire to dominate; or me for my love of dressing and new-found desire to be humiliated, forced, and teased.
I feel we did have a love for one another, at least for a while. But eventually she found her way into the arms of a real female (as well as another man, where she got pregnant, and I divorced her). I drifted away on my gossamer dreams of femininity, once again sidling into the dark, secret closet of my soul, unable to express or share my feminine side with my loved ones. Until I met my second wife. ~.^
PS -- This image ends the current Original Series. I will be posting holiday Cards and Postcards I created next. There may be new images added to the Original Series ... in truth, I am working on one now, but cannot get it right. Too, I have the Illustrated Story I need to reformat and figure out a way to post. So stay tuned and thank you for coming along on the ride thus far! I hope you have enjoyed it!
-- SD
I lied. This is the last of my Original Series images for now. This is a new image. Well, semi-new. When I first came back and began posting here, I posted a brand new cartoon on my blog. I reused an outfit from an image I had thought lost. Well, I found most of my misplaced images, including the Spring Sissy image in the pink striped top and blue denim short-all. I didn't want to let the cartoon languish in blog purgatory, yet I didn't want to subject my wonderful readers to a recycled image with different text, either.
So, I made a new outfit that is similar in theme to the old outfit and matching the new text.
Confused yet? I am. =/
On a slightly different note, several readers have expressed a desire to see a less gloomy Chris. So, here you go! He is not exactly smiling, but he isn't sad, either. I suppose he is half-way between the two. And a little surprised that is how he feels.
Oh, and I gave him a cute new hair style. Maybe that is what made him almost-sorta-semi-kinda happy?
Chris looks a bit younger here, too. He is still going on 15, even if he looks maybe 10 here. ^^;;
No autobiographical anecdote this time. Except to say I love pink and white! And pigtails! ~.^
-- SD
See? I listen to my readers! ^.^
There was a comment saying red was not Chris' color, and to try a white top instead. I decided to follow up on the request and now you have an All New BLSB cartoon.
I do think this one looks much, MUCH better. I kept the multi-colored hues in, as that seems to evoke the festive feelings of Cinco de Mayo and all things Mexican. The pony-tail was a hit, too, so that stayed. The shoes changed, however. The cross-gartered look works well in an upcoming (but old) Christmas image, but not so much for the Mexican clothing style. Simple red Mary Janes will have to do.
While I've not worn a traditional style Mexican festival outfit, I do love tiered, flowing skirts and tops with ruffles and puffy sleeves. I used to own several ruffled poet's blouses in varying styles, as well as a couple of flowing, tiered skirts of different lengths.
My favorite combo of the bunch was a teal poet's blouse and long, black velvet skirt. The blouse was a teal satin pull-over with elasticized neck to be worn on or off the shoulders. It was positively frothing with ruffles along the neckline and at the ends of the long sleeves. The skirt was ankle length, black velvet, and with five successively increasingly larger tiers ending in a lace edged bottom. With a pair of black ankle boots, I would dress up and go out with my second wife.
This was primarily a fall and winter outfit for me, the colder months being relatively mild in my native Florida. A few times she had me go as a "sissy boy"; the clothes, some light make-up but no padding and with a boyish hair style. I loved those games. *sigh*
Though not dated on the actual image, I created this one Halloween 2001 for Crystal's StorySite. I just recolored the Sailor Moon outfit used in Part 5 of the Original Cartoon Series and added a a little witch's hat.
Halloween has always been a crossdresser's paradise. It is often the one time of the year we allow ourselves to dress openly with little fear of people finding out our true nature. Though, sometimes, it is just this open airing of our desire that allows others find us out.
Growing up I went door-to-door in traditional Halloween costumes: sheet ghost, hobo, cowboy, construction worker, werewolf, and the like. There were three times, however, where tradition became untraditional.
The first I do not remember at all. Only a fading Polaroid in the family album lends credence to the story my mother tells me. In it, I am just nearing my third birthday and and surrounded by my sister and her friends. (She was seven then). One was a ladybug. Another, a boy, was a spaceman. A third is dressed like a nurse. My sister sported a girl-cat costume of headband ears with a bow, cute girly kitty face make-up, a black leotard with flouncy short skirt, and black tights.
The story goes I cried and threw tantrums because I wanted a costume exactly hers. This went on for days until my mom caved in and made me one, too.
So there I stood, in a cute girl cat costume, grinning to the camera as my sister looks down at me with a look of mixed aggravation and amusement. Her friends don't seem to care.
I wish I remembered all this. *sigh*
My second girl costume was when I was about seven. The parochial school I was attending was doing a Thanksgiving production. My mother, being the artistic person she was, was in charge of costumes and scenery. She had started early October preparing, and both my sister and myself were often used as dummies for her to work on the costumes. Yes, I wore the oft-recognized pilgrim outfits, male and female, as her dress dummy. As well as various Indian garb (we didn't yet call them Native American).
With Halloween upon us, and mom so tied up in costuming, she had no time to make me something, as she usually did. Buying one was out of the question for our relatively low income family. I wanted to go as a pilgrim, but there was no way mom was going to allow one of the costumes out and about on Halloween. They were too time consuming to make and funds were limited.
However the Indian costumes were cheap to do, and she had extra beads and feathers. She also had a single extra Indian girl costume ...
I was secretly excited when she told me I was going as a squaw (again, before the derogatory meaning of the word was open knowledge). However, I put up the expected fuss, and went a little far (for mom, happy for me). She then said I was going to have some make-up on as well as the faux leather, fringed and beaded dress and the feathered headband with yarn twin braids down to my shoulders. It wasn't much make-up; some rouge, lipstick, and mascara. No extra moccasins, either, so I wore a pair of my flip flops. ^^;;
The third time dressing in a girl costume growing up was in the seventh grade.
I was attending a private Christian school (mom swapped religions a few years earlier) and we were having a Fall Festival. (It's just a way for religious people to celebrate Halloween without calling it Halloween ... I never understood that). We could come in costume for the games, hay ride and haunted house. (Yeah, Halloween is bad, so let's call it different but still do everything the same ... duh).
Gwendolyn, a girl friend (not girlfriend), said she was going as a JV football player; pads, helmet, jersey, etc. With a wicked grin she asked if I'd come as her cheerleader. I may have agreed to fast because she looked at me oddly before laughing and smiling.
So, she lent me hers.
My sister, in the 10th grade, thought this was hilarious and girlied up my hair with a red headband, and put some light full face make-up on me. The red-and-white cheerleader outfit was not like you typically see, this being a Christian school. The skirt was knee length, the sweater was full sleeved and high necked, shorts were worn under the skirt. I had to wear my own sneakers, but I had a pair of socks with the little puff ball on the back. And pompoms, of course.
A few other guys came in drag, but I was the only one who was not done up in a parody style. I was teased a bit, and one senior guy pinched my butt. I think he thought I was a real girl from behind, because he had this blushing laugh when I turned around. Gwen thought this was the funniest thing.
Gwen was also the very first girl I kissed while dressed up.
We were in the haunted house and she was squealing and giggling at the cheap scares, holding my hand as we wended our way through. At one point, she dragged me into a darkened corner off the main path through the haunted house and suddenly kissed me. It wasn't a deep, soulful kiss. Just a quick, dart forward, pressing her lips hard on mine, and an even quicker release.
I was shocked and excited and scared and all floaty-feeling.
She wasn't the first girl I had ever kissed, or had kiss me, but I thought we were just friends ... and I was dressed in her cheerleader outfit!
I asked her why she kissed me. Her reply was simply, "Because you're cute."
She then pulled me back into the main path before the next kids came through. I followed in a daze, hardly paying attention to the cheap scares until we were back outside. Sarah acted as if nothing happened, and I was too scared to bring it up to her.
We finished the Festival out and I returned her outfit the next school day. She never brought it up again, and seemed a little more distant with me. She stopped sitting next to me in chapel, and in lunch she sat across from me instead of next to me like before the kiss. Every time I tried to mention it, Gwen would find an excuse to leave and became even more cold and distant.
Gwen moved just after Christmas; her dad was accepted as an associate pastor at church in another state. I was invited to her family's going-away party, along with other of her friends. It wasn't until near the end of it she grabbed my hand and asked me to go out back with her.
She started crying and said she was sorry she treated me like she did in school, that she really liked me and was scared because she never liked a boy in that way before, and because she knew she was moving soon even though it wasn't certain and didn't even tell her friends, and she said she'd write me and maybe I could come visit and ... It all came in a torrent of emotion. Words ran into words, tears streaked her face.
I just held her hands in mine and listened, a small cold ball of ... something, in my chest and throat. I was sad, and I realized I liked her in that special way, too. I told her this when she finally slowed down.
She practically leaped into my arms and we held each other for several long minutes. We may have stayed entwined for longer but her mother came out to see where she was. I could tell her mom was shocked, but she said nothing. Just a narrowing of the eyes and thin lipped smile. She cleared her throat and asked Gwen to come back in because there were other ... friends ... she should say good-bye to.
Gwen kissed me again, then. In front of her mother. Then she let me go and walked back inside, wiping her eyes and face as she did. Her mom looked at me strangely for a few seconds and told me my mom had called and was on her way to get me.
I never saw Gwen alone again in the remaining minutes I was at her house. We did chastely hug as I left; the same chaste hug everyone else got.
We wrote to each other for a few months after. But, as in many long distance relationships, things cooled between us over time and distance.
The last letter I got from Gwen said she was making new friends and liked her new school and church. She included a picture of herself in front of her new house, and wearing her old JV cheerleader uniform. On the back she wrote: "I still think you looked cute!"
I often wonder what may have happened had she not moved and we were able to get our feelings in the open sooner.
I suppose Gwen was my first real love.
It is also why I often use her as a love interest in some of my tales.
Sorry this has gone much longer than my usual anecdotes. The memories I just related are bitter sweet, but fond. I am glad I was able to share them with you.
-- SD
Thanksgiving 2001.
I hate jpg. It is so lossy. But, I went with a gradient background so the then standard gif image of 256 colors was not going to work. And, png was not supported in most browsers at that time. So, the only surviving image I have is a degraded and mildly pixelated one.
I did have fun drawing the outfit, though. My original intention for this holiday cartoon was to have Cristina (from the Illustrated Series) popping up from the lower right corner wearing a Native American style costume and winking. But, I wanted this online and posted before Thanksgiving that year and real life kept interfering with me getting the image done. So I left off the pop-up winking girl and sent it in. It still took until the first week of December to get posted so I should have just finished it. heh
No real crossdressing anecdote for this one. As I touched on in my previous Holiday Cartoon for Halloween, I was used as a dress dummy by my mother a few months before and wore both male and female versions of pilgrim and Indian outfits.
I have always enjoyed Thanksgiving. I liked having my family around, as my grandparents and aunt would often visit. I liked all the food. I didn't like the clean-up which was always foisted off on us kids to clean up, and me begin the youngest seemed to get the most to do by dint of trickle down authority.
Later, when my sister was married, we would all go to her place. Which was great. I didn't have to do clean-up or dishes! But, by then I was much older and offered to help anyhow.
I was always a trifle jealous of my sister at this time, as she usually got a new fall outfit to wear for Thanksgiving. Well, I did, too ... sorta. A new tie just didn't do it for me like the cute things my sister got. I got gypped like that for Easter, too. *sigh*
Still, Thanksgiving is a holiday I look forward to each and every year.
-- SD
All new, just for you, this Cinco de Mayo!
I tried a Flamenco dress, but could not get it right. So I opted for a semi-traditional Mexican outfit, though this one is not floor length. I wanted to show off his cross-gartered shoes! teehee ^^;; And, Chris is sporting a nifty new ponytail, too!
I've never celebrated Cinco de Mayo. I am not of Mexican descent, nor do I use the holiday as a reason to drink tequila or cerveza until the worms in the bottle start talking to me.
The traditional costuming worn in Mexico would be wonderful to try, though. I love the flowing skirts, the fluffy ruffles, the bright colors ...
So, here is my hope for a safe and happy Cinco de Mayo for you all.
-- SD
Happy Mother's Day to one and all!
Don't forgot to tell the mothers close to you how much you love and appreciate them.
-- SD
Remember to tell those you love how you feel today ... and every day!
-- SD
PS ~~ I know it is a surprise to see me after a 3 year gap, but ... here I am. I'm sorry I've been gone so long, and I honestly don't know how long I'll be able to stay. But, at least I brought you a nice present (I hope)!
PSS ~~ EEK! The site seems to have scrunched my image and made it sort of fuzzy looking. I am also reposting all my drawings to DeviantArt. You can find a clean version of this one there. Look for SissyDemi! ^.^;;;