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Short Skirted Sissy

 

(This is an older story I basically made up on the fly for this picture, but it works together so I decided to post it)

OW! OW! OW! Alex shouted as he endured his spanking. He squeezed his eyes shut and gripped the chair legs underneath him. He swore it was worse each time. Why did this always happen to him?

He had grown up. Both literally and officially according to the laws. At one point, he wasn't. He grew older, but had been caught in several immature behaviors and sent back to re-training. it had taken years, with him seemingly growing older only to be put back down in a dozen different ways. He'd lived in regression nurseries,  punishment and reformation centers, maturity schools,  with adopted families, even an old castle. He had gone through punishment training, reformation, all sorts of things where this had been expected. But then he had passed. He was allowed back into society, reinstated as a full adult, given back his age. He had a job, his own apartment, mature friends- all signs of his maturity. And yet he was still punished like a child, or at least a trainee. Why?

The women who had him bent over her knees- a tall redhead who insisted he call her 'mistress,' was a court ordered life coach. After he had spent so long undergoing the various embarrassing punishments and so often rebounding back and having to start over, he was only allowed 'under guidance'. She was supposed to watch him, help him, and ultimately determine if he really had matured or no. Maturity meant freedom, faking meant he would end up back as an adult baby, possibly permanently this time. She also, technically, had the right to punish him as she saw fit if. The fact that she did it so often and happened to use such degrading methods was none of the courts business- in fact, it would probably be used against him if anything. So here he was, all grown up and still getting spanked. He forgot which flimsy excuse she used this time. She had a bunch of them, that he was sleeping too late and rushing to get to work, leading to early bedtimes, that he had too much sugar and junk food in the house and wasn't eating healthy, leading to feedings, that his apartment was messy, leading to maid work... and on, and on, and all with spanking. He couldn't argue, the court would side with her, and they only needed a small excuse to see him back in pampers. He figured she just liked seeing him bent over her knee. Part of him worried she wanted much more. 

He could feel the spanking coming to an end, as she slowed. He was still yelping from the blows, and he felt a tear in his eye. He hoped she never did plan to adopt someone. She'd make a harsh 'mommy'- she seemed to love finding excuses to punish her charges, and had one of the strongest spanking arms Alex had seen. 

Eventually she stopped, turned him over and sat him down on her knee. Alex winced. Part of it was from the pain of a recently spanked bare bottom pressing down on her, and part of it was from embarrassment at the childish position. Laps were where regressees ended up, either bent over them or sitting on top, and a position Alex had spent far too much time in. She acted like she was doing it to comfort him, rubbing his back and rocking him, but he figured she was doing it to see him blush.

"There's a good boy, there's a good boy," she said soothingly. "Did you learn your lesson?"

Alex nodded.

"Good boy. Then go get dressed in one of your cute outfits," she said sternly, but with a smile.

"Wh...what!?" Alex gasped. She couldn't mean... no...
"Oh you know exactly what I mean sweetheart. I know all about whats in your closet, I see the receipts, remember? I need to go now and I think this will be a good reminder. And don't pretend your upset, I know you want to!" 

Alex stared at her with his mouth agape. She was right, he had been planning on it, but having her know and point it out... 

"Well? Go!" she said, patting his sore bottom. Alex yelped, got up, and ran down the hallway to his bedroom. He haired her live as he did.

Alex's bedroom was, from all appearances, as normal as could be. After years undergoing those particular punishments, he made sure of it. Blue walls, regular double bed, bookshelf, and a desk which he used solely for work. No toys, no dolls, no video games, nothing that could be seen as in any way childish or effeminate. He didn't even have anything that was pink. He made sure of it. 

At least, that is how it seemed. Taking a deep breath, he reached into his closet. He removed a large storage box and set it aside. Behind it was another identical box on top of a storage bin. He moved the box, opened the bin, and looked inside. It seemed normal- a few shirts, coats, winter clothes- just things he wouldn't need right away. He moved those aside, and there it was. The one thing only he, and now his mistress, knew about. 

Inside was a pink silken dress, complete with bows and ruffles, and stockings to go with it. There was a set of footed pajamas, designed after baby clothes but sized for an adult. There was a teddy bear, pacifiers, baby powder, and dolls. And, of course, hidden the furthest down of all, were his diapers- thick and white, patterned with bows, and looking as much like a baby diaper as they could at that size. Blushing, he choose one of the pampers, powder, the pacifier, and the dress. 

He lay them down on the bed and stared at them, blushing. He never got over the embarrassment of wearing them. Part of him still hated them all, and perhaps himself for buying them. He always felt a bit upset putting them on.

However, after years of being forced into them, of struggling to hide his humiliating undergarments only to have them deliberately flashed in public, of working to avoid being treated as a child at any cost, of doing everything he could to look mature, not to mention the stress of the punishments, the shouting, the spankings, the work, the mocking... part of him had grown to love it too. If anything, being babied was one of the rare times he was unlikely to face much in the way of stress and simply be comforted. No one was ever really mad at a baby, expected much of them or demanded responsibility. He had always found himself in that position anyway, why work against it?

Quickly, he opened up the diaper and spread powder on it. He lay down and taped it on. The cooling powder and the soft material felt good against his still sore bottom. Most of all, though, he felt secure. After months of responsibility and doing everything that was expected of an adult while avoiding anything at all childish, there was something comforting in just letting it go and accepting something so infantile. He stood up, adjusted the diaper, then pulled the dress over his head. He put the pacifier in his mouth and got socks and bows on.

He luxuriated a moment in the soft silk and padding, then moved on. He still had to make supper that night. He walked into the hallway and toward the kitchen.

He passed by the bathroom, and caught a glimpse of himself in the mirror. Instantly he blushed and looked away. It was still embarrassing to see himself like this, even if he had put it on himself. After a moment he forced himself to look again. He walked into the bathroom- a standard white tiled place with a bath and shower- and looked at himself closely. 

Embarrassing as it was, he really did like the look of all the cute and pretty clothes, all the pink, all the bows. Would he ever want this all the time?

No, he thought. Much as it was fun for a bit, he hated being in it too long, and hated being seen in it. He especially hated when he had to use it, or actually get treated like a baby at all times. In the end, the complete lack of freedom, the lack of anything at all meant for his real age, and with the constant humiliation was awful. He shuddered just thinking of it. He wouldn't go back there if he could.

A strange sound snapped him out of his thinking. It was something like a scrapping. Was it a mouse? He walked into the living room, looking. Maybe it was his imagination.

"Well well well, what do we have here little one," he heard his mistress say. THAT wasn't his imagination. He spun around quickly, only to see the flash of a camera taking his picture as he turned.

"AWWWW SHE"S SUCH A CUTE LITTLE BABY!" he heard, followed by a wave of laughing.

There, laughing and taking pictures, was not only his mistress, but a dozen of his friends and workmates. They were all cooing at him, giggling and laughing. He backed away slightly and raised his hands in front of himself as if he could hide behind them. They must have snuck in while he was getting dressed.

"Awww look at him, he is blushing!" said one of his friends, who until now had thought of him as a mature adult.

"I really didn't believe you until I saw it," said his boss, who he doubted would have him work normally again.

"No no, this is what SHE really is," said his mistress. "A sweet little baby girl, hiding in a big world, masquerading as an adult." She walked up to him and grabbed his gloved hand, then sat down and pulled him down on his lap.

"Is this what you want little girl? To be a baby? I can send you right back to the adoption center now, let you live as your real age." The others nodded and loudly cheered their approval.

Alex shook his head vigorously. "No, please... I was just relaxing! I don't want this! Please!" A few hours, on his own, was fun. In front of all these people with the threat of it becoming permanent was horrifying. And he knew what it all meant- not just dressing this way, but having to act this way, get treated this way...


"Oh really? And do you think the court will believe it after I show them this picture?" she asked, showing him the photo in her camera. It was the worst possible position for him, with his skirt high enough to reveal his diapered bottom, his thighs still red from the spanking, and his head turned just enough to show his bow and his pacifier at the same time, while leaving his full face visible, with no chance of confusing who it was. "And do you think you'll go back to this life now? Do you think your friends will see you the same, or your work?" They all laughed at the thought.

Alex felt tears form in his eyes. He let her hug him in close to her chest, rocking and comforting him like a baby. They all saw him as such anyway, he might as well play the part. He was even dressed for it, and of his own decision.

"I'll let the court know what you've been doing, and what you really are deep inside," she said. Alex whined and began outright crying, he knew, like a baby. "Don't worry little one, I'll make sure you don't go back to those nasty punishment centers. I have other plans for you."

Alex nodded. The punishment centers really were awful. They stressed the harshness and the humiliation most of all- doling out plenty of spankings, mouth soaping, locks and public displays. Usually they were meant as a set up for either reformation and maturity training, but Alex knew that if he went back there, he'd be there for a long time. And with that photo, he didn't doubt she could send him anywhere she wanted. Now his friends would support it to.

It seemed he would be up for adoption after all, and permanently this time. He figured he knew who would be the first volunteer.

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