Yawning. It was the single most predictable thing you could do in the morning. Flash Sentry reached one hand out of the warm covers of his bed to hide his mouth as his first yawn of the day caused him to squirm awake.

The bed that held him was soft in every way imaginable. Silk sheets, doughy mattress, downy quilt, and pillows that literally defied all efforts to define how cloud-like they were. In all, it was a very agreeable bed for someone who was dainty and sensitive.

Truly, the only problem with the bed was how hard it was to leave it behind in the morning.

But Flash had experienced the wonder of this bed for two whole months now, and though it had been impossible to free himself from it (mentally and, thanks to some judicious tucking-in, sometimes physically), he now had the knack of it.

Turning to the side, Flash had to bicycle-kick at where the covers were tucked under the mattress, then finally shove his legs out and stretch them apart when he'd made an opening. With such a hole made, Flash could usually then pull at the covers and fling them back to make his escape.

It was silly, but Flash liked to do silly things when he was all alone. Silly things helped keep him balanced. Turning around, the huge, soft shirt he'd worn to bed twirled around him and came back to rest at mid-thigh.

Laying on the end of the bed was his dressing gown. It was silk, pink, and he knew full well how good it would feel against his skin. The soft cotton of the shirt dragging over his naked body almost felt like betrayal—sure it was soft and kind to him, but the silk would be so much better.

Flash caught sight of himself in the full-length mirror in the dim light of morning. He bit his lower lip in a self-examining, self-conscious moment. He had some tone, but rather than rugged, fuzzy skin like all the other guys at school had gotten, Flash had soft and hairless flesh that was as sensitive to touch as his fingertips.

Pulling on the gown was like being wrapped up in a hug by a giant silkworm. At least, that's what he thought it would feel like. He made his way to the bathroom and immediately took the robe back off to take care of his morning ablutions.

Soap-less body wash, no-tears shampoo, and the softest loofah on the face of the planet were the implements with which Flash cleaned himself—anything less would have left him itching or worse all day. With that done, however, Flash was free to dive back into his dressing gown and pull it around him like a silk cocoon.

The scuffing sound of his feet on the polished wood floor was all that marked Flash's passing to the kitchen. Despite how the day would eventually go, he was always determined to start things off right. Filling up the coffee machine and turning it on, turning on the broiler to make toast, and lifting out butter to start softening were just some of the duties a live-in housekeeper like Flash Sentry would undertake at the crack of dawn.

Checking the clock, he slipped some bread under the broiler to toast while he poured the first cup of coffee.

"That smells amazing."

The voice was like warm honey rolling down Flash's spine. He turned slowly to look upon Celestia—not a princess like in that pony world and not a principal to him for over a year now—as she stood in the doorway wearing her own pure white dressing gown. Of course, she wore hers with the belt loosely fastened so that the front opened halfway down to her belly button, showing off skin that was a soft pink that evoked a desire in him to walk forward and kiss it.

His need to touch her—to worship her—took but a moment of conscious thought to banish. "Anything particular for breakfast today, ma'am?" Professional. This was his job, and no matter how much Flash desired to be draped onto Celestia's body, it would not do unless he was invited.

"Just my usual, thank you Flash." Celestia took a seat at the table and, no sooner had she sat down, she lifted the cup of coffee that Flash put before her.

It was a blissful little reward to hear her praise. Flash had to bite his lip, though, as the moment the tall woman sat down his viewing angle changed from looking up slightly at her chest to now looking down.

"Sister, you're teasing her again." Luna's voice came from the same hallway Celestia had just emerged from. She was already wearing a tight-fitting jogging top, short shorts, and had her long and luscious hair tied back into a ponytail. "Put your breasts away and let poor Flash do her job."

The embarrassing thoughts that made Flash blush seemed all the more so now that he knew Celestia intended him to get flustered. "I-It's really no bother. I don't mind."

"See, Luna? She doesn't mind." Celestia looked up at Flash and batted her eyelashes. She also shrugged her shoulders just a little—causing her gown to open a tiny bit more. "Don't let Luna tell you what to do, Flash, this is my day to play with my adorable little maid."

It was the word Flash, Celestia, and Luna had agreed upon. It was their trigger asking if he would want to play games for the day. It would be so easy for him to just reply with anything but acquiescence, but…

Curtsying, Flash lowered his eyes as he had every day either of them had invited him thus and said, "Oui, madam." Two words that he'd never accidentally say in response to her implied question.

As he raised his eyes, Flash saw two fantastic smiles. The raw feeling of joy and affirming of his feelings that they gave him made a happy little giggle bubble up from deep inside.

Luna visibly shivered and then let out a mournful sigh. "Sometimes I regret my morning routine. Have fun, you two, and don't do anything I wouldn't." The last words were spoken to her sister as she turned for the door and headed out for her morning run.

Flash watched the way Celestia licked her lips, like some big predator spotting something tasty that couldn't run fast enough to get away from her. He shivered at the imagery and turned his attention back to Luna before she left the house without him wishing her well. "Good bye, mistress!"

It was a fun game, of course. Flash got paid for his cleaning work regardless, but if he played the game the sisters had set up for him—he got to enjoy it too.

"I laid your things out for you, Flash. I hope you find them as cozy as the last ones." Celestia was almost literally devouring Flash with her eyes. The gown he wore was so thin as to almost be sheer, and it showed off his slim physique perfectly—it also betrayed the fact that he was wearing not a scrap of clothing underneath.

"Yes, mistress, I'll just serve your toast up first before it burns." With practiced ease, Flash used a dish towel to slide back the tray of the broiler and quickly reached to pluck the toast from the tray. The moment his fingers got close, the heat almost undid him. All his life he'd had to deal with his sensitive fingers—it was what made him so good at playing guitar—and while he'd worked on his heat tolerance, it was still below normal. "Hot-hot-hot."

Feeling Celestia's eyes on his back, Flash blushed a little as he buttered the toast, offered up two little bowls of spread, and set all of it on the table.

"You are such a good girl, Flash. Please, take some time to yourself to go get dressed. We have a big day today." Celestia didn't hesitate to start spreading grape jelly on her toast, though her eyes kept flicking to Flash while he watched her.

The way he was always addressed as a woman had been cause for a lot of embarrassing blushes at first, and even one denial when he'd felt a little too overwhelmed by it, but it had become a comfortable game among many such. "'A big day'? Don't you have to be at the school in an hour?"

"Flashy. You must be a little muddled." Lifting her coffee, Celestia took a long sip of the dark brew. "School holidays started three weeks ago. As of today, we have a month break from school." It wasn't just what she said that had grabbed Flash's full attention, but how she'd said it. Carefully enunciating every syllable, Celestia let her voice lower a little as she spoke. "Which means we can have a little fun. Do go, dear, and get dressed."

Flash couldn't stop himself, he curtsied again and left the kitchen. The moment he was in his bedroom again, his heart started thudding in his chest and his wobbly legs almost gave out. The casual way she addressed him as a girl, the looks she gave, and even the view she gave Flash of her cleavage all made him want to drop on the bed and rub his thighs together all day long.

It was a pretty dream. To be a kept, perfect little angel who got to play games all day and not work. Pretty dreams, Flash had learned, sometimes came true. Two months previous he'd been out of work and needing somewhere to live when he found a position vacant for a live-in housekeeper.

Walking over to the bed, his legs feeling a little like jello, Flash spotted what Celestia had given him to wear for the day. Flash's breath caught in his throat as he saw the dress.

They'd been playing with Flash using female pronouns for a while—long enough that Flash felt relaxed enough to indulge in his girlier side—but this was way new. It was— "Is that a maid outfit?"

He reached out to the frills and the soft lacework and felt his legs start to squirm again. He couldn't. Of course he could, it was expected. But he simply had no idea where to start with it.

Before Flash could even think of a plan on how to attire himself in an actual dress, the well-oiled door hinges betrayed him by letting Celestia in silently. The first he knew what was happening was her hands coming to rest on his shoulders.

"Would you like some help with that, Flashy?"

Celestia's purr came from above and behind Flash, and it made his legs wobble all over again. When he didn't immediately respond, he felt her hands sliding the silk of his gown over his shoulders. "Y-Yes, mistress. P-Please?"

Just saying those words—meaning those words—made Flash squirm his legs more. It was freeing, embarrassing, and joyous all at once. He let her hands glide down his shoulders, over his arms, and down to his waist where she pulled gently at the belt. The moment it let go, Flash shivered—he was standing here completely naked and fully exposed before his former headmistress. Now, though, she was only his mistress.

"Poor little thing, you're all nervous. Have you never worn a dress before?" Her hands wandered now, one sliding up to Flash's chest to rub slowly over one side—giving the impression of a breast being stroked.

For Flash, that sensation wasn't far from the mark. His chest had always been sensitive, his nipples little match heads that only needed the gentlest touch to explode into fire. Right now, Celestia's thumb was the only thing to actually touch his nipple, and only every circle of her hand did it gently work the nub.

The rotating pattern took all of Flash's attention. His mind was beset by the swirling touch, and each moment thumb and nipple met his thoughts evaporated. He could vaguely feel something else happening—another touch from her free hand, but he barely registered it until Celestia removed her hand from his chest, brought it lower on his body, and a distinctive click sounded.

Now he could think again, Flash reached down to where the sound had come from. His palm brushed his belly and down to his groin where he encountered something hard. Without Celestia touching him, he rushed over to the mirror to look at what she'd done.

"Just a little precaution, Flashy-dear. Dresses are for good girls, after all."

The words made Flash shudder. Just where his legs met was a small pink device. It looked vaguely like the end of a sausage had curled over, was made of plastic, and now he could see it he knew what had felt odd—his penis was trapped inside.

Realization had the inevitable result of making him hard, which was exactly what the device was there to stop. Tightness reined around his shaft. It denied him the most basic of adult male activities—having an erection.

"I've got a gorgeous pair of panties here for a gorgeous girl."

Flash barely heard her. His eyes were fixed on the device locked onto his straining member. He'd seen, in various spare moments spent browsing online, such things—but he'd never thought to be wearing one. He couldn't help himself, he squirmed his thighs together and felt the chastity cage stretch at his balls and cause him to moan out loud.

"Flashy? Come over here and stop playing with her." When he looked back at Celestia, she'd sat down on the bed and was patting her lap.

"It's so tight. Is it meant to be tight?" Despite his complaint, sitting on Celestia's lap—and leaning against her chest—was literally the best thing he could think of right then. Walking over to her, trying to not grind his thighs together more, he couldn't shake the tightness of his groin.

"Good girl. Sit down and relax."

Being called a good girl had become a treat. Flash felt a little rush of ASMR tingles from the back of his head all the way down to his tailbone. He knew it made him wiggle, and he didn't care one bit.

Turning at the right moment, he felt her hand press to his back to guide him as he perched on her long legs. Relax he did. It was like touching her body just soaked all the anxiety and strain out of life. He could tilt his head to the side and rest it against Celestia's shoulder and let her handle difficult emotions.

"There we go. Now you just relax and let me take care of that hair. I don't know why you had it cut so short, but time can fix that."

Where Celestia produced a hairbrush from was less important to Flash than the feel of it finding his hair and working through it. Closing his eyes, he slowed his breathing and relaxed completely against Celestia's body. Each stroke of the brush stirred a little sigh from his throat and before long they were audible as the softest of whining sounds.

As the brushing continued, all the worry over the tightness of the chastity cage slipped out of Flash's mind—actually, most thoughts slipped out of his mind. He just sat there, relaxed and happy, having his hair brushed like a good girl.

"Is that better?"

The concept of a question was slow to process in Flash's head, but he found himself nodding ever so slightly and his whines changed to an "mmhmm" for a moment.

"That's my good girl. Did you know Luna's buying you a dress too? I gave her your measurements. She said she wants to find something that will make you feel as sexy as she sees you."

Flash's awareness spread to the tightness once more. Celestia made him feel pretty, but Luna made him feel sexy—she didn't need a dress to do that, but now that dyke had been breached, there was apparently no going back to pants and a shirt.

Something about the way Celestia held him, the way she treated him, let Flash just give up all pretenses and revel in the attention.

"Now, let's get you dressed. Legs up, Flashy."

With Celestia's arm behind him, Flash didn't fear falling. He leaned back into the embrace, and lifted his legs. Completely off-balance now, he couldn't feel safer.

With her free hand, Celestia worked the white panties over his feet and slowly drew them up his legs.

"You need to wax these."

Following Celestia's gaze, Flash saw her looking at his legs. He didn't have much body hair to begin with, but her hand running along his legs had found the little skin-tone hairs that dotted his legs here and there. "O-Okay."

"You don't have to worry about it. I'll text Luna to pick some up and teach you how to do it." Celestia kissed Flash's cheek and pulled the panties all the way up to his thighs. "Okay, stand up and I'll get these all the way up."

Jumping to his feet, the mirror caught Flash's eyes, and he watched Celestia pull the panties up to his hips. He could only stare at himself in the mirror, finally managing to say, "Those have—"

"Tinkerbell. Isn't she just adorable?" As Flash nodded dumbly at the sight in the mirror, Celestia pulled the panties up all the way and over the bulge of the plastic chastity cage.

The tightness in his panties increased, but Flash had to agree that Tinkerbell on the front of them was just about the cutest thing ever. She was poking her head out of a keyhole—which he had to liken to the locked cage he was wearing under them.

"Turn around."

Turning, Flash's eyes fell on Celestia and a thrill ran through him. She looked gorgeous, sitting there on his bed, but more than that she looked so—so motherly. When she stood up, he had to tilt his head to follow her face.

Walking to Flash, Celestia reached one hand out to his chin and, gently, turned his head to the side. "My little sweetness, look at the back of them."

Turning his head a little more, Flash looked at the mirror and saw the big, red love heart over his butt. He couldn't stop the gasp that slipped out or the giggle that followed it.

"You like them?"

Flash nodded, but realized she would want him to say so. She loved making him admit he liked girly things, and though he truly did, he wanted to make Celestia happy too. "I do, Mom."

The moment the last word slipped past his lips, Flash's cheeks started to do an impression of a pair of twin bruises. He blushed so much his face actually felt hot. "I—"

Celestia brought a single finger to Flash's lips to silence him. "Shh. You can call me mommy if you want—if it helps you feel more comfortable."

Despite his embarrassment, Flash recognized the tone in Celestia's voice. Desire, hunger, need. Now he'd opened the can of worms, there was no putting it back because it made her happy. What made Celestia happy might embarrass him, but Flash couldn't deny how hard she worked to make him happy. "A-Are you sure, mommy?"

It was like watching the sunrise of a chill, winter morning. The world itself seemed pale and frozen by comparison to how Celestia looked. Her eyes twinkled, and Flash was sure he noticed the corners of her mouth jump a little higher.

What came next was Flash's reward. She was so tall and so strong that when her arms pulled around his shoulders, he wasn't just dragged into a hug—he was dragged into a hug against her cleavage. He let out a happy little sigh and was absolutely complicit with the act of being smooshed against her chest. With one ear pressed to her bare flesh, Flash could hear Celestia's heartbeat.

"Mommy's perfect little angel." She squeezed him a little tighter, then let go. "But we must finish getting dressed before Luna returns."

In a daze, Flash couldn't help feeling phantom touches against his skin—as if she were still holding him. When he felt something being pulled down over his head, however, Flash shook off the aftereffects of a good mommy-snuggle and followed the repeated directions.

"Arms up and to the side. Good girl." Celestia was now able to pull the puffy-sleeved maid dress down Flash's torso, feeding his arms through the sleeves and getting the loose top onto his shoulders.

The feel of the soft silk against his torso was heavenly for Flash. It was like his sheets, but frilly. For a moment he lost track of what Celestia was doing as he thought on the idea of frilly sheets, but when she started to lace up the back of the dress, his mind was jerked back. "T-Tight."

"Too tight?" Celestia asked. When Flash nodded, she quickly eased off the laces a little. "Better?"

She'd been so quick to make him comfortable that Flash wanted to reward her. "Yes. Thank you, mommy."

The beaming smile Flash saw in the mirror was worth the renewed embarrassment. He watched Celestia come up behind him, bring her arms over his shoulders and pull him back against her in a hug. The position had the side effect of forcing him to look at himself in the mirror, and what he saw was so different to his old style.

It wasn't a costume "sexy" maid dress. The skirts came down to the top of his ankles. There was still a layering of white skirts under the black outer one, but it sat neatly and didn't make him look like a joke. The dress came up his chest, hugging against him, until it reached the folded white collar that was so lacy it looked like someone had spent years creating it.

The sleeves that came down his arms stopped just above his elbows, where more ruffled white lace peeked out from under it. Flash looked into Celestia's eyes as she rested her chin on the top of his head and smiled at her.

"Does my little lady like her dress?" Celestia asked.

Flash didn't trust his voice. He would squeal, whine, or gasp—so he just nodded to Celestia. The motion of his rosy cheeked head moving caused the dress to move slightly, the hem of the skirts brushing his shins. That's when Flash let out a little gasp anyway.

"That's not all, Flashy. Sit down on the bed and let mommy put on your new shoes." Letting go of Flash at last, Celestia reached out to take the shoes from the little pile of accessories she'd laid out.

Watching Celestia move in the mirror, Flash slowly turned around too and climbed up on the bed. Each step he took reminded him he was wearing a dress, but what was more surprising was how tight he felt again. The grip of the chastity cage was unyielding. The device was perfectly sized for him to allow him a little firmness but, ultimately, he couldn't get hard while wearing it. "Focus on the dress," he said under his breath.

Celestia waited for the blushing boi to get his rump up on the bed before crouching down. "Right leg first."

Lifting his right leg, Flash watched as Celestia slipped a small white sock over his foot first. The opening of the sock, of course, was frilly and had a little ribbon sewn onto it and tied in a bow at the front. Like the skirts, the sock was so soft it made him wiggle his thighs in delight.

The shoe, when she slipped it over his foot, wasn't too over the top. It had a heel of two inches—which would add only slightly to his petite height—but the front of the shoe was thin. There was a little black ribbon on the footwear that Celestia wrapped around his ankle and tied in a bow just below that of the sock.

"Other one now, little princess."

She was going all-in on the girly-talk today, or so Flash thought. He let his right leg hang back down and lifted his left one. Again a dainty sock and a slightly-heeled shoe was set on his foot, and the lace ribbon of the shoe tied in a pretty bow.

"Stand up, Flashy." Celestia's hand gathered up the last item from the bed. "Follow me and we'll take care of your hair in the living room."

With Celestia leaving the room, Flash was left to stand on his own and follow. Setting his feet to the floor felt strange—his feet were tilted so that his heels were higher than the balls of his feet. When he stood up on them, they felt stranger still.

His balance was forward, the shoes making him tilt a little until he fought with his body to make himself lean back and straighten his legs. With an almost constant blush at the range of new, feminine sensations, Flash took his first step in the raised-heel shoes and almost fell over. He'd tried to plant his heel first, but with the extra size of the heel that made the shoe grip while his leg was half extended.

Throwing his arms out to the side, he windmilled them a little before regaining his balance. Bringing his back-foot forward was easy, pushing it out in front of him less so. Each step to the door resulted in a scuffing sound from the heels of his shoes, and from there he spotted Celestia stepping into the living room.

Author's Note

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