Flash Sentry's Charmed Life
𝓒𝓱𝓪𝓹𝓽𝓮𝓻 3
Previous ChapterNext ChapterFlash tried not to kick his feet as Luna carried him down the hall, but the urge was too strong.
"You're all squirmy. Relax and tell me what the problem is." Turning sharply at the bathroom door, Luna carried flash into the room, closed the door, and fastened the lock.
Flash was caught a little by surprise when Luna slid him down, pulled his dress up, and set him on the toilet seat. The strong, musky smell was evident and he was unable to escape the reality that his attempt with toilet paper had failed.
"What in the world is—" Luna lowered herself to her knees and hooked her thumbs in Flash's panties to pull them down his legs. This, of course, gave her a point-blank blast of boi-arousal. "You really like that cage, don't you?"
"Y-Yes." Admitting such things was a guilty pleasure for Flash, but a pleasure nonetheless. Even just talking about it made his shaft tighten further in the cage. "I-I made a mess earlier. I tried to clean it up."
"Wait here. I have an idea that can help you." Standing up, Luna turned and unlocked the door.
Flash watched her leave with mounting worry. He'd been into Luna's room to clean it many times, but only once had she left her closet open. The sight of all the toys and restraints—all neatly hung on the doors and inside of the closet—would provide fantasies for the rest of his life. He had no clue what they all did, but that didn't stop him squirming his legs together in sissy glee at the possibility that he'd now find out.
When Luna returned to the bathroom (once again locking the door behind her), Flash could only see one thing different—she had her purse with her. He didn't dare move a muscle, not sure what her plan was.
Kneeling down again, Luna reached into her purse and pulled out some soft wipes. "Pay attention. If you're going to be wearing that cage in the future—and I think my sister seems set on you doing so—you'll need to know how to get and stay clean."
Staring, trying to ignore how much he was straining inside the cage, Flash witnessed Luna cleaning him up with a wipe—the light lemon scent slowly replacing that of his own arousal. It occurred to him that Luna wasn't really teasing him. "Thank you."
Dabbing away the last few drops (that Flash had made while she'd been cleaning him), Luna was reaching back to her purse again when her phone beeped.
Flash had to sit there while Luna pulled something paper wrapped from her bag along with her phone. He knew well that Luna wouldn't tolerate him trying to do something silly like get away.
"Oh my. Well, that's a definite yes." Luna tapped away on her phone, presumably sending a message. "It appears Rainbow has spoken to her significant other, and they want to make it a doubles game."
"O-Okay." Eyes fixed on the paper package, Flash barely registered what Luna said.
"Celestia will be out all day, so that means you'll be playing doubles with me." Placing her phone back in her purse, Luna started to unwrap the little paper package. It was small, about the size of her palm, and she kept her eyes on Flash's face as she unfolded the pantyliner. "Those won't do at all."
It was squirming time for Flash. He recognized what Luna had in her hands, but it was her taking his panties off that had his shaft exploring the tightness of the cage to the best of its efforts. With the offending (and still rather musky) panties off, Flash froze stock-still at the sight of a pair of black, silk panties that Luna started working onto him. "Those are—?"
"Mine. You had better not ruin them with your mess." Tugging the panties up to Flash's knees, Luna reached for the pantyliner and drew it out of the packaging. "This is how big girls keep themselves from making a mess."
There was so much going on that Flash wasn't sure what was the most embarrassing. He had Luna showing him how to put a sanitary pad into a pair of her own silk panties that he knew were soon to be girding his loins. "L-L—Auntie Luna?"
Luna's head jerked up and looked at Flash for a few seconds before a big smile spread to her lips and made her eyes light up. "What is it, Flashy?"
"H-How is this going to help? I'll make a mess still, and it will be in your panties, and then—" He halted as a dark blue finger pressed to his lips. Flash froze, unable to talk with such an imposing gesture.
"You are about to learn the wonder of these pads, Flashy. That mess you made will be fine." Luna pulled the panties up and over Flash's thighs, then his hips. "But don't think you can just raid my supply. This one is a gift, but you're going to have to start buying your own."
Life was becoming both more complicated and more embarrassing, but there was only one answer he could give. "Yes, Auntie Luna."
"Good girl. Now, to make things easier, I'll come with you for your first trip." Standing up, Luna put the wipes she'd used on Flash in the little trash bin and tucked the Tinkerbell panties into the empty wrapper the pantyliner had come in. "Freshen yourself up and we'll go."
"But—But—But I'm wearing a—"
"Dress? Of course you are. Now freshen up." Luna turned for the door and walked over to unlock and open it. "Don't forget to come back to the living room so I can put your shoes and socks back on."
Flash just stared at the dark and sexy goddess of a woman as she left him alone. There was only one thing he could do under the circumstances. Holding his skirts up, Flash stood and turned to examine himself in the mirror.
Obvious was the black panties. They looked almost painted-on. There was a hint of lace at the seams, but apart from that they were the smoothest looking fabric he'd seen in his life. The front of them, of course, was outlining the chastity device he wore—and even now started to strain again thanks to examining himself in the mirror.
Less noticeable was Flash's fingernails. He held up a hand to the mirror and couldn't stop giggling at how pretty they looked. Letting go of the dress, Flash let it drop to its full length and then patted down the skirts to have them sitting right again. "I can't believe I'm going to do this. How can I be going to do this?"
With his dress neat again, Flash washed his hands in the sink and took a big breath. His first real step wearing the panties almost made him shudder. They clung to his hips and felt like he was wearing nothing at all.
Taking a moment to banish a meme or three, he opened the bathroom door and headed into the hallway. The swish of silk against his most sensitive flesh was rivaled only by the cotton-like padding in the front of them.
Walking to the living room, Flash heard soft sighs in the air. Airy, feminine sounds that inspired an image in his mind of a cute girl faced with very girlish problems. When he realized, upon reaching the doorway to the living room, that it was him making the sounds…
"Blushing again? My word but our girl must be constantly having the most curious thoughts. Come to Mommy and let aunt Luna put your socks and shoes on." Celestia, still wearing a single, large towel, held her hands out wide for Flash in invitation.
Not one to ever turn down a cuddle with his mommy, Flash didn't stop blushing all the way over to Celestia. He turned at the last moment to sit beside her, but Celestia caught his waist and lifted him onto her lap.
"Sis, you've…" Luna seemed hesitant to continue speaking and, instead, sat down on the floor and started putting Flash's socks back on.
"Don't be silly, Lulu. It's just us girls here. What's a little wardrobe malfunction when I have my little darling to snuggle?"
When Celestia hugged him back against her chest, Flash felt what they were talking about by way of two heavy breasts pressed against his shoulders and neck. "M-M-Mommy?"
"Just lean back and let your aunt Lulu put your shoes back on. She told me you and her are going for a little shopping trip. Something about tennis skirts and special shoes?" With one hand around Flash's tummy, Celestia kept him pinned in place against her naked torso. Being larger than the boi, if he'd turned his head a little he'd see the large white breasts flanking his neck.
Luna seemed to be taking an age to get Flash's shoes back on. He tried to lean forward to see what she was doing, but between Celestia's firm grip and the dress he wore, Flash had no chance.
Each breath Celestia took, Flash could feel. It was almost unbearable to have the woman of his dreams (at least half of them) pressing her naked self against his back, but there wasn't much he could or would do. As far as Celestia or Luna's sexual pleasure went, Flash knew his dick was off the menu.
"Okay, Flashy, let's get to the mall before they close." Luna stood up, revealing her full height to Flash as she loomed over him slightly. She held out her hand to him—half offer, half command.
Reaching up, Flash let Luna capture his hand in hers and was pulled to his feet and out of Celestia's grip. A new desire filled him—a new ache. Twitching, biting his lip, he slowly started to turn his head back to look at Celestia, only to see the towel was back in its place and constraining her chest.
It was something he'd dreamed of, the times he'd been in class in high school and she was substituting in for a missing teacher. Not that he was the only one who had dreamed of getting intimate with their teacher, but Flash was fairly sure he was the only guy who'd dreamed of just sitting on her lap and leaning against those pillows.
"Flash, did you hear anything I just said?" Luna asked.
Like a deer in headlights, Flash carefully shook his head. Lying to Luna would be its own tragedy. "I-I was thinking about—about when I used to d-daydream…" He was stuttering way more than even usual when he got caught by one of the sisters.
Luna delivered Flash a look that said, We will have words later, and tugged on his arm. "We shouldn't be too long, Tia."
Desperate to keep up with Luna, Flash was pulled along in a rush of submissive bliss as she got him into the car (being careful of his dress) and on their way to do some shopping. They were halfway there before she cleared her throat. "What was the daydream about?"
"I—It's really embarrassing."
"Is it about me?" The weight Luna put on the pronoun should have been illegal in public; it sounded so good.
"N-No. C-Celestia."
"Mmmm…" Luna dragged the sound out like she was tasting something delicious and sweet. "Tell me about it and I promise she will never hear it from me."
"It's still embarrassing." It took another full minute for Flash to work up the nerve to actually spill the details of his first boyhood fantasy. "She's got really big—"
"Tits. Breasts. I know, Flash, trust me. There's a young woman deep inside me that always wishes she had a chest like that, but then the realist in me reminded me how much she pays for bras and how often she complains of a sore back." Sparing just a single look, Luna managed to convey the agony of the younger sister to Flash. "Sorry, you were saying?"
"I wasn't the only guy who looked at her like the rest of the world didn't exist." Just thinking about telling Luna what his fantasy was made Flash squirm a little in his seat. "I just wanted to sit on her lap and snuggle against her chest. I know it's pretty tame."
Pulling into the mall, Luna slowed and parked the car before speaking again. "Flash, that wasn't easy for you to admit, was it?" When Flash shook his head, she smiled and leaned across to kiss his cheek. "Which is why I will reward you. I won't tell Tia, like I promised, but I will get her to hold you like that."
The cage around his penis felt a hundred sizes too small. "Y-You mean it?" His thighs wouldn't stop squirming and he knew—for sure—that the pad was doing serious work to keep him dry.
"When we started, Flash, what did I tell you?"
"Today?"
"No, when you first moved in. I told you I'd make your deepest dreams come true."
Moving into the house with the sisters had been a heady rush. Flash had thought it would just be a job—a live-in job, but still just a job. What he'd gotten, however, was a ride he'd never forget. He shivered in the car, despite it being perfectly warm. "I thought you were teasing."
"I was, but it can be two things." Luna climbed out of the car, leaving Flash sitting there to realize that he was about to go out in public wearing a dress.
"L-Luna?"
Walking around to Flash's side of the car, Luna opened the door. "What's the matter?" She spoke as if she couldn't possibly think why Flash would be nervous.
This was part of Luna's games, Flash knew too well. She would want him to tell her what was making him embarrassed, she would have him then embrace that embarrassment, and then she would reward him for it all. "I'm still wearing a maid dress." He said it as he was climbing out of the car, struggling against the blush that seemed intent on plastering itself to his face.
"And yet you climbed out anyway. You're a good girl, Flash Sentry." Taking Flash's hand, Luna guided him away from the car, using her free one to lock the vehicle, and led the way toward the front door of the mall.
It was all a mind game for Flash. He walked across the parking lot, his thighs gliding together in girlish embarrassment, but with Luna's hand in his he couldn't stop. She was so solid and commanding—uncompromising. He had no choice, or so he told himself, but to follow her lead.
The cool blast of air as Flash entered the mall failed to cool down the heat in his cheeks. Everyone would surely turn his way, raise their arm—then a finger—and point at him.
Any second now.
There! Someone pointed… at something in a store window.
No one was staring. No one even so much as batted an eyelash at him. That didn't stop him from being a spooked bundle of nerves that jumped every time someone so much as glanced his way.
"All they see is a woman leading her niece around the mall. You should just relax and enjoy the sights." Luna turned and took the two of them into a huge department store. "Come on, our destination is feminine care products. Select us a basket."
Reaching out to pick up a basket in his free hand, Flash saw that nail polish he was wearing and, as if Celestia were there with him, he felt a boost. With a turn he would never take himself in this store, Luna led him deep into pink territory. There were bras and panties and other things that Flash didn't know the name of but knew they were meant to drive men wild.
"I hope you're looking forward to your tennis game tomorrow." Luna, clearly knowing the layout of the store, could focus her attention on Flash and still know the right turns to take them both to the feminine hygiene section. "With how much of a mess you're making, you're going to need thick pads."
The aisle ran half the length of the store, and fully half of it was filled with just pads. Flash stared in mute, male panic, but Luna led him along until they reached about a ten foot stretch of packages that all had the same color pattern as the one Luna had given him.
"Sport? Well, you will be playing sports, but I don't think they will do the work. You don't want to have to keep rushing to the bathroom to change pads—trust me there. Everyday? Of course not. Heavy days? Pregnancy pads? Okay, those are probably too much. Heavy ones will have to do." Reaching up, Luna selected a pack of pads and set it into Flash's basket. "Probably best to make it two, if you like the—ahem—equipment Tia got you, you are going to need to keep wearing these."
Flash looked down at the ground and pictured shreds of what remained of his masculinity falling away. This was definitely it. He was in a big department store, in a dress and shoes with heels, in the fem—
"Flash, come on dear." Luna tugged at Flash's hand—which on the whole was a rather effective way to move him around. "We might need to come up with a better name for you than Flash. It just doesn't have a good feminine edge to it. Don't you think so?"
It was enough of a change of topic that Flash forgot his existing problems to latch onto it. "Do I—Do I really need one?"
Luna stopped and pinned Flash with a look. "You can use it now if you want to tell me no."
Safeword. Flash had one—he had a few for Luna, actually—but there was a general word he could say that would stop all the embarrassment and they would just be two adults shopping together and talking normally. "I-I-I'm fine. Thank you."
His words earned Flash a playful tousle of his hair. "Good girl." Luna gave Flash a moment, and when he nodded she smiled and tickled his chin. "Come along, you're going to need some more panties to use with those."
Panties. It was more than just a word to Flash, it was a concept and—now—a way of life. His tangled and distractible brain took that moment to remind him that he was wearing Luna's panties. They were so soft, so precious, and so billowy in some places. Flash knew his boyish behind didn't compare to Luna's curves, but a boi could dream.
"Fleurette?" Luna asked.
The word drew Flash from his musings to the owner of said panties. "S-Sorry?"
"You are just a bundle of distraction today, aren't you? I was musing on a name for you. Fleurette sounds nice, and catches in my ear nicely. It has a nice shortened version—Fleur." Pulling her phone from her purse, Luna started typing away on it. "Put these in your basket."
Flash mutely took the three pairs of silky panties from Luna and put them in his shopping basket. He barely noticed the patterns on them: the first pair were simple and pink, another had a sun motif, and the last had a dark blue/black with a moon on them and lace around the edges. He knew for sure what Luna would have him wearing.
"Tia likes it, but she wants to give it a test run before committing." Luna put her phone away. "Okay, and just a few little things now." Flash was a little less passive now and walked at Luna's side, hand-in-hand with her still. They stopped at the makeup counter. "I'll need a soft yellow lip gloss and a strong chap stick."
Behind the counter, the bored woman turned and fetched four items. "The yellow gloss comes in glitter and non-glitter. The chap stick has two flavors: cherry and grape."
"I believe I'll take all four, thank you." Luna looked down at Flash and caught him looking back up at her. "Trust me. If we're going to spend time on the court, those chap sticks will be worth their weight in gold."
For just a moment Flash caught the sales assistant's bored, despondent glance and there was no recognition at all—no hint that she sensed Flash was anything other than what he looked like.
Just as Luna guided Flash away from the makeup counter, though, he caught sight of himself in a mirror. It was just a glance—a flash of Flash—but without looking closer and focusing on details all he saw was a girl wearing a dress. "Do I look like that?"
"What was that, dear?" Luna asked as they neared the registers.
"I just saw myself in the mirror and I don't look like a guy."
Putting an arm around Flash's shoulders, Luna gave him a hug. "Of course you don't. Now put the things on the belt for the lady to scan."
A little numbed by the realization that he looked feminine enough to easily pass for a girl, Flash put the panties, the lip balm, the gloss, and the sanitary pads up without even giving it much thought. He was so distracted with the thought that he missed the woman ringing them up asking him a question.
Luna squeezed Flash's shoulder again. "Sorry. She's a little overwhelmed right now."
The woman looked at Flash, then down at the things on the belt. "Oh! Of course. Poor dear. Well, I hope you have a great day tomorrow."
Flash was blushing just as hard as ever now. How closely had she looked at him? He knew, of course, that if he opened his mouth and replied, anything he said might alert her that he wasn't a girl. His voice was high, but not quite high enough to pass easily—or so he thought.
Luna paid for the items, collected them in a bag, and they made their way out of the store and out of the mall completely.
In the relative safety of the parking lot, Flash finally got up enough confidence to speak. "Did they really think I was a girl? My hair isn't long enough."
"And we're working on that, aren't we?" Luna seemed to love tousling his hair. "A little more and you will have it down far enough that we will need to style it."
Blushing at the thought, Flash tried to hide how much he wanted that—how much he really wanted that. It might not work with someone as astute as Luna was, but he could try. Ultimately, however, he couldn't win this fight. "How do you think I should wear it?"
Flash could tell when he'd made Luna happy, her face would break into the most glorious and radiant smile, and now that smile was bestowed upon him. It washed away his embarrassment, shame, and any lingering doubts he had about any aspect of his new life.
"Well, we'll need to trim those bangs for a start, but I think it will make you even more beautiful." Reaching her hand up, Luna tousled Flash's hair.
It surprised Flash how much bounce and body he felt in his hair. All his life he'd had it cut short into guy hairdos, but now? Now it felt silky and soft and there. What really hit him, though, was the way Luna had said "more beautiful", in that she already thought he was. For that matter, it wasn't handsome or hunky or any of the other epithets that males were tarred with. Beautiful.
The ride home was full of introspection. Luna kept quiet, and Flash couldn't help but join in the silence with his own, but it just meant his mind could race more effectively down each and every avenue of thought. He was beautiful—it had to be so, because Luna had said it. Even the girls in the mall hadn't for a second thought of him as anything but just another girl.
When they pulled-up at their house, Luna reached a hand over and held Flash's thigh—stilling his movement. "You've been squirming the whole trip. Good thoughts?"
Flash knew he was blushing again, but he didn't care about that right now. "The kinds that make me squirm." When the hand on his thigh squeezed just a little, it had him squirming again.
"We've had a lot of fun today, Flash, but you do remember you have a job to do?" Giving his leg one last squeeze, Luna climbed out of the car and went to the back of the car.
Climbing out, Flash barely got both legs turned and he caught sight of himself in the wing mirror. It was just a brief vision, but again it was a shock because in the moment he was looking at himself, his brain registered girl. It was as exciting as it was embarrassing.
He quickly circled around to the back of the car and helped Luna with their purchases. Carrying them inside, he rushed to his bedroom with the bag of sanitary pads, hoping Celestia wouldn't spot him.
The pads were in the top drawer of his dresser a scant half a second before Celestia knocked once and opened the door.
Flash spun on one heel, his dress spreading out a little around him as he faced her down—and immediately capitulated in the face of Celestia's motherly demeanor. "I'll start doing the cleaning now."
"Oh, Fleurette, you are such a good girl." Celestia's smile got a little wider as she said the new name, giving Flash a good hint that she liked it.
The name tickled inside Flash. It was certainly girly enough for their games, but he would need to try to incorporate it into his sense of self quickly if he wanted to keep the fun rolling. "Thank you, Mommy."
With how Celestia's features softened even more, Flash knew he had used the exact right words. He walked to her when she held out her arms and let her fold him in her embrace. Standing upright, when Celestia hugged him it brought his head in just below her breasts, which put them out of his reach, but made for a cozy place to cuddle against her belly.
He was just so small compared to her. Even with the heels and if he strained to get as tall as he could, he'd be lucky to bump his forehead against her chest.
"Have you had a good day, Fleurette?"
Flash nodded his head against her.
"I'm glad. It's going to be a long break from school, and I want to make sure my little girl is enjoying it."
It was one of his favorite parts of living with the sisters. Just cuddling with Celestia—with no obligations or requirement for him to perform or match up to someone else. But he also had a job to do. "I'll get the vacuum."
Author's Note
Support me on Patreon or fuel my writing on Ko-Fi!
Join me on Discord. Warning, said chat may contain NSFW material and should be considered adult in nature.
Awesome ponies who are already helping to keep me in keyboards and rum:
A.P.O.N.I.
CadelDdraigDarkkon
Canary in the Coal Mine
Daremo
Dio-Drogynous
Ender Voidwalker
KFS Crimson
shortskirtsandexplosions
Sirion123
Vi Watch
And special thanks to the following, for careful eyes and friendly words:
Lab
