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Double Down: School Daze
#1
Christopher stood uneasily before his mother as she reiterated his punishment to the scared -- yet secretly excited -- boy. The fear and nervousness he displayed were real, but he was having difficulty keeping his mostly feigned pout from slipping into a trembling smile of thrilled excitement. Those lips carried a hint of lipstick, teasingly applied by his older sister whose clothing he now wore. His lightly mascaraed and lined eyes shimmered with barely checked tears as Christopher tried to appear sulky.

The tight feel of the pretty flowered white leggings was one of the girl-clad boy's favorite sensations. The thin cotton panties adorned with a ubiquitous girlish cartoon cat on the front and her name of Hello Kitty on the rear felt so different from his normal boxers, and almost like he was wearing nothing under the leggings at the same time. Chris also loved how the waist of the ruffled babydoll top felt so far above where a normal boy's waist would be. Those ruffled hems and sleeves swayed gently as he fidgeted under the stern words of his controlling mother and the gleeful gaze of his vindictive sister.

It was his sister who was put in charge of Christopher's wardrobe for school. And the scheming boy was starting to think he may have miscalculated with his plan. The reality of his once-secret and former fantasy was now quickly becoming all too real.


(A continuation of my real-life Double Down story, though now moving into pure fiction. The face is mine, de-aged and head swapped onto an image from an online girls' clothing website. Other touch ups and the like were by my clumsy hand in my old PSP9x program.)


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#2
An ingenious (and fitting) punishment. It is the age old problem for Christopher, though. On the one hand he is being offered the chance of a lifetime yet on the other has to contend with the views of those whose opinion he values. 

Maybe he will find that really there are others out there whose opinion he should have been paying more attention to all along  Wink
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#3
Those like Christopher are very lucky. The tale is a thrilling read. Love the caption, great photo editing skills.
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#4
(01-17-2021, 07:46 AM)Girlygirl Wrote: An ingenious (and fitting) punishment. It is the age old problem for Christopher, though. On the one hand he is being offered the chance of a lifetime yet on the other has to contend with the views of those whose opinion he values. 

Maybe he will find that really there are others out there whose opinion he should have been paying more attention to all along  Wink

Part of Christopher's desire to dress in girls' clothes is he enjoys the perceived shame of being seen as a boy dressed in girlish things. He loves the clothes and how they make him feel, but the secret taboo of what he enjoys is also a compelling factor. Add to that the idea of being forced to wear the girls' clothes by his mother and his sister makes it even more delicious for him.

Obviously, Christopher is just a stand-in for me and my desires. A large part of me just wants to wear the clothes I find cute and that makes me happy while wearing. The other part thrills at the social stigma of a male wearing female things. I am, in reality, terrified of what could happen to my relationships (friends, family, work, neighborhood) if I were found out or just decided to wear what I really wished to. (And a more than a small part of me wants to find out!)

For now, I will be dressing in the privacy of my home (for the first time in nearly 20 years). Working from home, I spend my days dressed in cute things, comfy panties, and cozy sleepwear. I think in the last 30 days or so, I've only worn male clothes when I've had to go out. I've even checked my mail and taken the trash down and up a few times while in my girlie clothes ... though always late at night. (Even though a street light is right in front of my house!)

I also dress in clothes any real woman might, not the outrageously ultra-feminine sissy wear some people enjoy. This is not to say my clothes are not full of pinks, flowers, ruffles, bows, and the like. *^.^*

(01-17-2021, 11:46 AM)afp Wrote: Those like Christopher are very lucky. The tale is a thrilling read. Love the caption, great photo editing skills.

I wish I had been that "lucky" in real life at that age. I read some of the experiences at a young age some of you on this forum have had and get small twinges of jealousy. (Not to say I have not had more than my fair share of crossdressing adventures in my later youth. hehe)

I hope to add more to this tale, along with more images.

I find it a thrill to add my de-aged face to the cute outfits I wish I would be made to wear were I the age of my digital fantasy avatar.

And, thank you for the comments about my "skill" ... in truth, it is mostly the phone app called FaceApp doing the heaviest lifting. There is often clean up and touchups needed to varying degrees. But I've done digital captions, or as I call them illustrated stories or cartoons, since the mid 1990s.  (You can find most of them under my former alter ego of Sissy Demi at https://www.deviantart.com/sissydemi )
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#5
Thank you for your thoughts, Daughterboy. Ironically, now might just be the perfect time to experience ‘public dressing’. If done in an area where the risk of being seen by an associate is low to begin with, the current prevalence of masks should eliminate whatever risk might remain.
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#6
Double Down: School Daze -- Part 2


The following day, Christopher waited on his porch for the school bus with his heart in his throat. As the cross-dressed boy began to realize the day before, the reality of being forced to wear girls' clothes while remaining an obvious boy was far from the fantasy he had built up in his mind.

For one, his strict but usually loving mother took every opportunity to remind Christopher, and any others around, that he was now just a cute sissy; a boy who likes to wear girls' clothes. And she seemed to be relishing making him fulfill his punishment. His sister took the changes as an opportunity to prove that girls are indeed better than boys. Her most recent comments as she dressed her brother in her old clothes echoed in his head.

Yesterday at school could have gone worse, but it certainly wasn't the fantasy he dreamed of in his mind. There was the expected name-calling and confusion, even a few veiled threats of getting beat up. Those threats actually drew a large group of kids to him as self-appointed defenders of the "school sissy boy". Mostly it was girls, but a surprisingly decent amount of boys became protective of the cross-dressed boy. There were also a surprisingly felt the same way Christopher's sister did, and while protective of their new sissy pet, they were also somewhat belittling of him as a semi-feminized boy.

Teachers and staff were either turning a blind eye to his girlish attire, openly praising him for "showing his authentic self to the world", or joining in with the snarky comments and teasing words within the limits they felt they could get away with. Apparently, Christopher's mom had called the school and advised them of what to expect regarding her son's new wardrobe of girls' clothing, and warned them of legal action if they stood in the way of how she decides to raise her child.

Christopher sighed as he spied the bus a block away.

He had argued and whined at the outfit his sister had forced him into this morning. He thought his token resistance was believable and began to comply after his mom had to threaten him with further punishments, citing "If you continue to act like a baby, I will make you use a pacifier to show not only are you a sneaky little sissy but a big baby, too!" That was not even close to a part of his plan, so Christopher quickly grew silent and allowed his sister to get him dressed.

The combination of long tight cuffs and billowy sleeves on the salmon pink and black polka dot top made a striking look and felt fun to wear. His sister informed him they were extended bishop sleeves as she had him slip his arms through before popping the three little black bead-like buttons through the keyhole closure of the high neck. A pair of her blue denim skinny jeans slid up his legs, and while as seemingly tight as the leggings of yesterday, felt much more substantial. His sister laughed and said she was going to get their mom to have him shave his legs nice and smooth. At least he didn't feel half-naked below the waist with his thin cotton panties like with the leggings, either.

"I don't have a lot of old panties to give you, oh sissy brother of mine," his sister winked conspiratorially, "I'll tell mom she needs to take you to get some of your own. Oh! And some cute matching training bras, too!"

White platform sneakers and no-shoe socks were slipped onto his feet, along with a comment about maybe painting his toenails later that week.

The final touches were added to Christopher's cute ensemble: a big black velvet bow was pinned low to the nape of his short boyish hair and a light application of eyeliner, mascara, and matching glossy pink lipstick was applied with gleeful intent by his sister.

The partly terrified, partly exhilarated crossdressed boy's heart was fluttering in his chest to match the butterflies in his tummy as the bright yellow school bus squealed to a stop one stop away. With a rueful smile and a bolstering sigh of resignation, Christopher stepped off his porch and began walking to his stop a few houses down on the corner.

"Look, it's Sissy Chrissie!" one boy shouted.

"Leave him alone!" one girl yelled back. "He's very brave and very cute in that sweet outfit!"

"Yeah!" a larger boy called out. "You can sit next to me, if you want, Chris! I won't let those haters bother you."

Christopher gulped, unsure of what to think at that, just as a hand slipped into his from the side, startling him.

"I like your outfit today, Chrissie." It was an older girl a year ahead in his middle school. She was smiling at him warmly, though with a strange glint in her eyes. "I loved it on your sister when she wore it last year before moving on to high school. You look so sweet in her old clothes."

Speechless, Christopher was tugged into a group of kids and led by his hand into the school bus that had just arrived ...


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#7
He really does look very cute. And despite his fears, the reception could certainly have been a lot worse with the positive responses seemingly capable of counteracting the negative. 

As they say, today’s news is tomorrow’s chip paper and with a decent swell of support behind him, the nay sayers will have moved on to some new revelation pretty soon (if he’s really lucky, he might get some of his male counterparts to see the light)  Big Grin
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#8
Double Down: School Daze -- Part 3


It was embarrassing enough to take the bus and walk the halls of his school dressed in his new girlish attire (even if this was ostensibly his plan at one time), but now Christopher stood before the entire school wearing more of his sister's clothes. His Machiavellian scheme to live out his fantasy of being forced to wear girls' clothes had worked all too well; things were out of his control and not anything as he fantasized about.

The principal had called the unscheduled assembly and had Christopher stand next to the podium in front of the bleachers in the gymnasium. Long minutes went by as Principal Carver went over trivial school business and announcements all while the femininely clad boy stood by nervously fidgeting. Christopher could see only a few kids were paying any attention to what he was saying. The rest were giggling, pointing, whispering to one another, and holding up their cell phones for pics and videos.

He shuffled his feet and hung his head, cheeks aflame, but Mrs. Haversham, his guidance counselor who didn't seem to like him even before all this happened, lifted his chin with one finger saying, "Oh, no, Christopher. No hiding your face, sissy. Your -- mommy -- said this is something you secretly wanted. She sent me a copy of your journal. So now you get to live out your perverted little fantasy and be a sweetly dressed sissy boy for all your schoolmates to see."

She began fussing with the tiered ruffle hem of his blouse, adjusting it to increased sounds of laughter from the assembled kids.

"Your sister always wore the cutest outfits," Mrs. Haversham said moving to adjust the sit of the blouse on his shoulders. "You look darling in them, too, of course, my boy. Even if they are suited more to a 6th grader than an 8th grader." She then reached to his forehead and tousled his hair down into a semblance of messy bangs. "I do so hope your mom keeps your hair short so that you stay looking just like a boy in your yummy girl's outfits."

Principal Carver started on the real reason for the assembly: Christopher.

He wanted to die. This is really not what he wanted when he conceived my plan. The principal finished up talking about the clothing drive and how anything not sized or suitable for Christopher would be donated to needy girls, but that charity starts at home and we should take care of our own first.

"Don't worry, sissy," Mrs. Haversham hissed the last word. "I have your sizes from your mommy and sister. I'll make sure you get to wear everything the girls want to donate that fits ... maybe some that don't. Now smile and get ready to thank all the girls in advance for their generosity in giving you their old clothes. And try not to show how much of a sissy boy you truly are, eh?"  Christopher followed her eyes down to the noticeable package in the front of his borrowed girl's jeans.

She joined in the laughter at Christopher's fumbling thanks and blushing face.


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#9
On the upside, going public is always the most difficult aspect. With no doubt a great deal of clothing about to be donated, he will no doubt look back on this in a few weeks when he has a new wardrobe of feminine clothes and his peers have found something else to amuse them, as a part of the process that is fully worthwhile. 

As for his guidance counsellor, it strikes me she ought to give serious consideration to a career change.  Big Grin
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#10
A delightful assembly, hope he doesn’t get teased too much, thrilling both good and bad but will be fun for him and the girls. I wonder if some other boys mothers and sisters might be inspired by him.
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