Flash Sentry's Charmed Life

by Damaged

𝓒𝓱𝓪𝓹𝓽𝓮𝓻 4

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Flash's dreams were all mixed up. One moment he was back in high school playing with his band, the next he was at graduation with his mom in the crowd expecting him to do something amazing with his life, and then—then he was living his best life.

It all happened with a sense of safety around him that softened what could have otherwise been some horrible nightmare. Instead, that softness reminded him of Celestia's arms and Luna's hand patting his head.

Softness had saved him from a bad night's sleep. Flash woke to the softness still being around him in the form of the pillowy mattress and high-thread-count sheets that encapsulated his sleepy self and guarded him from the harshness of his past.

Yawning, Flash poked his head out from under the covers and looked around the room. Morning was advancing, as was evident by the orange light streaming through the curtained window. Flash yawned and squirmed a little in the bed, enjoying the sheer feel of his silk bedclothes and the covers on his sensitive skin.

His bedroom door opening made him pull his head back under the covers and feign sleep. It would have worked if it'd been Celestia, but when the covers were pulled back, Flash knew he was dealing with Luna. "Wake up, Fleurette. We need to be at the court by eight."

Squirming, Flash tried to burrow into the sacrosanct part of the bed, only for Luna to laugh and pull the covers off completely. "I was warm and cozy and—"

"We have tennis to play, Fleurette. I don't intend to lose, and that means I need a partner who can move their cute behind on the court." Demonstrating her strength, Luna reached under Flash and picked him up in her arms. "Now, come on and get up or I'll make us breakfast."

She was clutching him to her body. He was more aware of the almost-sheer fabric of her midnight black dressing gown than he was of breathing. It was long—reaching down to her knees—but Luna had left the top loose, her breasts threatening to break free of the confines at any given movement.

"Wait!" Flash backtracked his thoughts to the threat. He'd made the mistake of letting Luna prepare food on several occasions. While she seemed to understand her cooking bordered on inedible, she also lacked a sophisticated palate and had an iron constitution—Luna could survive her own cooking, but there were raccoons that had had very bad indigestion after rifling through the trash at their residence. "I'll get up and make breakfast."

Smiling, Luna set him down and started laying clothes on the bed from a bag she'd carried in. A dark blue (and very short) tennis skirt, long blue socks, a shirt that had blue fire around the bottom leading to white sleeves and collar, various sweatbands, and there was a clunk of what looked like tennis shoes on the floor when Flash looked over the edge. "Then get dressed and we can go already."

Watching Luna leave, Flash was tempted to chase after her like a puppy dog. She was being commanding and dominant, the perfect traits that let a good boi just relax and be guided. "Bow-wow."

Sliding off the bed that always seemed that little bit higher off the ground than was comfortable to sit on, Flash pulled off the long sleeping shirt he'd been wearing. Standing naked, he looked at his dresser and a shiver ran through him as his eyes locked onto one drawer in particular. It was in there.

Could Flash put it on himself? Did he dare try?

A single knock at the door and it opened. Flash turned to see Celestia walking into the room with a smile radiating out for her features. "Good morning. Are you ready for Mommy to put your little clitty protection on?"

Celestia looked stunning. Any man worth his salt would be drooling at the way she hadn't tightened the belt of her pure white dressing gown quite tight enough—letting her cleavage show almost all the way to her nipples. The gown was also short, leaving her thighs exposed to the morning air and, if the hopes and dreams of men everywhere meant anything, a glimpse of something more. She wore a thin, gold necklace that seemed to dip down between her breasts, disappearing into its soft prison of flesh.

Clitty protection. The word stole all of Flash's attention and he shivered at the way Celestia worded it. Blushing for all he was worth, he nodded to her. "P-Please, Mommy."

Walking to the dresser, Celestia opened the drawer and lifted out the cleaned and dried cage, also producing a little lock from the little chain that delved into her cleavage..

Flash stood stock still as Celestia crouched down—giving him an amazing view when he followed her with his eyes—and she started to put the cage on. It closed around behind his balls, requiring her rather personal handling of his very personal assets. The front closed and she slipped the lock behind it, fastening the two hinged parts together and sealing it in place.

He would have loved to stare longingly down Celestia's cleavage, but he was being selfish—his eyes couldn't stray from his locked-up self. The tightness started a moment after her hands left him, his shaft trying to grow hard and mighty, but barely getting to firm and spongy. What it did to his sense of masculinity was even stronger.

Flash felt more like Fleurette again.

"Thank you, Mommy." The words tumbled out in a rush. Flash was so excited to have the cage back on that he forgot completely that he was standing there naked—until Celestia pulled him into another hug. Her soft gown might as well have been an impenetrable barrier. He could feel every curve of her body, but rather than the alluring woman she was, Flash only felt the warmth, comfort, and acceptance of a parental figure.

"You are most welcome, Fleurette. Do you promise to be good for Luna today?"

"She wants me to wear skimpy things." Flash's eyes drifted to the skirt on his bed. "I prefer long dresses." The words had tumbled from his lips before he could think what he was saying, but the soft blush in his cheeks made it clear enough he did like dresses. "I-I mean I like—"

"It's alright, Fleurette, to have opinions on fashion. All girls do." Celestia stroked the back of Flash's neck as she held him against her. "But I really have to go. So promise me you'll do everything Luna says."

"I promise."

Crouching down again, Celestia stopped when her face was just a little higher than Flash's. She booped him gently on the nose and then kissed the same spot. "Good girl, now get ready for your exciting day."

Flash was completely and utterly defeated by Celestia. He nodded and looked into her loving eyes. "Yes, Mommy."

When Celestia retreated from the room, Flash was all alone with his thoughts, a cock cage, and an admittedly cute tennis outfit. Though he saw it as cute being on a girl, not cute being on him. That just brought flashbacks of the previous day and how even women hadn't thought of him as male.

Before the skirt and before the shirt, Flash needed panties. He closed the door and approached his dresser, lifting out a pair of the new panties Luna had gotten him along with one of the sanitary pads. He stepped into the panties and unfolded the pad when he had them up to his thighs.

Doing his best, he pressed the thick pad to his underwear and held it until it was stuck, then pulled the panties up and over his hips. The feel of the thicker padding against his groin made his legs squirm, and a check with his hand revealed that the extra thickness made it so there was little definition to the cage that clutched his intimate parts so securely. "I look like a girl."

Just thinking that usually made Flash squirm, but saying it out loud made him squeeze his eyes closed and rub his thighs together—his imagination taking the concept to its logical conclusion. One naughty hand stayed down to his panties and felt the front of them, the smoothness there only reinforcing his day-dream.

His hand traced up from the panties, over his soft belly, past his cute (or so Celestia called it) belly button, and further. His chest was flat, but a single finger grazed his nipple and sent a shiver through Flash that made him squirm his legs together and roll his shoulders.

"I'm getting distracted."

And he was. A lot. His first task was to hide those traitorously sensitive nipples under the soft tennis shirt. It was light and soft and it hung almost like silk. With a happy sigh, he reached up and fastened the three buttons at the collar.

Next was the skirt, which looked short to his discerning eyes. He worked it over his feet and shimmied it up his legs. When the skirt's elastic pulled tight around his hips, Flash realized how short it was. He stepped over to the mirror and bit his lower lip. To his surprise, he couldn't see his panties in the reflection.

He needed his socks on next. When Flash unrolled them from the tucked-up ball, he found they were tiny with little pleats at the seams. Sighing in contentment, he pulled them on to find they barely got to his ankles. Next came the tennis shoes which took three tries to lace up he was twitching and trembling so much.

Flash couldn't do it. He closed his eyes before turning his head to the mirror. "On the count of three. One. Two…" His eyes flew open when a pair of lips pressed to his cheek.

Luna was bending forward and down, kissing his cheek. As her lips parted from his flushed flesh, she reached up and lightly tousled his hair. "Good girl, now come and have breakfast."

In record time Flash got his shoes on and raced to the kitchen. Bouncing on the balls of his feet, he quickly made some toast and scrambled eggs for both of them while Luna prepared several bottles of water with ice in them.

Sitting down at the table with Luna was exciting. She was always active in finding new and interesting ways to make him both comfortable and uncomfortable at the same time.

"So, Fleurette, are you ready to win the game today?" Luna asked.

The new name was still finding its place in his sense of self, so it took a moment for Flash to respond. "Y-Yes! I just know we can beat them."

Luna ate her breakfast while watching Flash, which left him feeling a little concerned, but finally she set her knife and fork down and said, "If you just had something a little fluffy in the chest, no one would ever call you out for not being a girl."

Biting his lower lip a moment, Flash tried to keep from saying the wrong thing by finishing his breakfast. A tall glass of water helped too, and soon Flash was cleaning the breakfast dishes while Luna fetched some more things.

"I've got us some headbands and wristbands in case we get too sweaty, plenty of water, and some fresh things in there in case someone makes another mess." Picking up the bag she'd brought out, Luna gestured to the front door of the house. "Well, Fleurette, are you ready to back me up on the court?"


The drive filled Flash with apprehension. He was going to meet one of his old high school friends while in Luna's care, and that meant Luna had control of the situation. And, there'd be a stranger!

Just one car was parked at the courts, though there was a motorbike beside it. Knowing what Rainbow was like, he assumed it was her motorbike. When Luna pulled in and turned the car off, they both climbed out into the warm morning.

"There they are!" Rainbow's voice cut through the quiet morning. "Hey, Luna, Flash!"

"Oh, sure, just go and literally shout for the whole world to hear," another voice that seemed familiar to Flash said. More could be heard, but it was said quietly enough that Flash was unable to make it out.

"Now, Fleurette, I don't want you reacting to that other name. Just let me handle that, okay?" Luna slung one bag over each shoulder, one of which Flash'd seen her fill with water and things, the other he assumed she had their actual gear in.

As they rounded the back of the big wagon parked beside them, Flash could finally see Rainbow and— "Sour Sweet?"

Sour had one arm balanced on each of Rainbow's shoulders as she leaned over her. They were both wearing white tennis shirts, though Rainbow's had a rainbow-patterned stripe from the collar down one side and Sour's had a small heart printed on her left chest.

The way Sour stood over Rainbow, her mouth just an inch from Rainbow's forehead, it seemed a very domineering pose.

Drawing back from Rainbow and looking at Luna and Flash, Sour's eyes noticeably dipped down and traced back up again—twice. "Isn't it such a lovely day for tennis? At least it would be if my pet knew her place."

Luna's stride shifted just slightly before she reached out and put an arm around Flash possessively. "Perhaps some introductions are in order? This is Fleurette, she'll be my double today."

"H-Hi." Flash tried to hide a little behind Luna. Sour had, apparently, experienced a growth spurt coming her way since the last time he saw her and she could almost tuck Rainbow's shoulders under one arm. Leaning a little more against Luna, Flash proved that he could definitely fit his shoulders under her arm.

Turning to look at Rainbow, Sour looked like she was about to say something, but then relented. "It's super-great to meet you, Fleurette." Her eyes flicked up and to the side of Flash. "I remember you from—Luna, wasn't it?"

"It is." Luna nodded toward Rainbow. "Does your pet have a name?"

"When I'm happy with her." The snarl was back in Sour's voice, but like Flash remembered from high school, it flipped on a dime and she turned and kissed Rainbow's cheek. "Lucky for her it's hard to stay angry with her. This is Rainbow."

"I believe I've met her before, as has Fleurette. Though, I wasn't aware she'd found an owner." The nuance in Luna's voice was perfectly obvious to Flash, though it was only his familiarity with her that let him know that she was basically telling Sour that she was fine with the game.

"Literally the best thing that ever happened to me." Rainbow turned an adoring look on Sour and got a rewarding smile back. "We met at college and just kinda clicked."

"I found her trying to start her bike in the rain. It was the most pitiful thing I've ever seen. Talked her into coffee." Sour Sweet seemed about to say something, then bit her lip. "Then I talked her into coffee."

"She's really convincing," Rainbow said.

Flash was surprised at this new side of his old friend. There was a bit of a bond he felt, of shared experiences, though he felt things were a little different to the dynamic that he'd seen in Sour and Rainbow so far.

It made him appreciate the balance of relationships he had with Luna and Celestia. In one, he had a woman who would deride and punish him in ways he adored, as well as bring him pleasure beyond his wildest dreams. The other woman in his life was softness, safety, and reassurance that all his gentle and sweetest dreams would be reality.

When he looked at Rainbow, Flash could see a mirror of his own perfect life reflected. She loved her situation too. Smiling at the knowledge, he realized Rainbow was smiling back.

"Soooo—Are we going to play tennis or talk about our cuties all day?" Sour Sweet had that look again, like she was trying to not say something. The strained expression faded as she hugged Rainbow a little tighter.

"We can do both on the court." Luna led the way, through the fence and onto the court. She set down the two bags and lifted a pair of rackets from her bag, as well as two cans of balls.

In Flash's hand the racket felt well-balanced and the grip seemed perfectly sized for his fingers. He hadn't played much sport since high school, but he'd played tennis and done some track there—though not enough of either to bulk him up in any way. The sum of his exercise of late amounted to what he got while cleaning the house and spending time with Luna—though that time with Luna could scarcely be called exercise in the traditional sense, it certainly got his heart rate up.

In no time at all they were on the court and warming up with a few practice games. Flash was a little surprised to find that Rainbow and Sour were almost evenly matched, and while he and Luna were fine together when Luna was serving, he kept getting distracted by Luna whenever it came time for him to serve.

Luna's skirt was just as short as Flash's and when she was standing up close to the net—bending forward in an aggressive stance—Flash got glimpses of her panties. The sight didn't just snare his attention, every time he saw those midnight panties the cage around him got tighter and tighter. By the time their practice game was over, Flash was fighting not to squirm his thighs together with every step.

Sour and Rainbow walked up to the net to meet Flash and Luna. If he weren't wearing the cage, Flash knew he'd have an erection that would be visible to all three women, but the cage gripped him like a vice and kept him from even being able to contemplate a masculine role in sex. He tried to avoid squirming, but whenever Sour's eyes drifted to him, he kept squeezing his thighs together—which he knew was what drew her attention.

As Luna came in beside him, Flash was aware of something he'd always noticed when she became highly active in the bedroom—Luna had a scent to her. It was work being done, her body being exerted, and her will being carried out by her flesh. It was intoxicating to Flash whenever he smelled it in the bedroom, and it was no less potent now. He wondered, feared, and maybe even hoped that his cage would explode at any moment.

"Why don't we make a bet?" Sour asked. "And, when you lose, we get to have a little fun with your boi there."

The words broke through Flash's daze and focus on Luna. He was aware of two other scents. His eyes were drawn to Rainbow again, to see beads of sweat getting caught by the headband she'd put around her brow. A flicker of sunlight hit one and scattered her namesake across his vision.

"And if we win, I get to put a collar on your pet for the rest of the day." Luna's eyes instantly sparkled with the intensity she exuded.

With all the time he'd spent with Luna, Flash could almost feel the radiant, dominant energy pouring off her—and it only made him squirm more. She was less like a confident older woman and more like a goddess.

"Two rules." Luna sounded like the strict school disciplinarian she was. "First, safe words for all parties." Everyone nodded firmly to that. "Second, Fleurette's cage doesn't come off."

It was one thing to be wearing it in public and quite another to have everyone nearby know he was wearing it public. Flash blushed more than he had in days.

"Third, Rainbow doesn't get to climax." Sour reached up and booped Rainbow on the nose, smiling as sweetly as an angel. "She's sitting at a week now, and she hasn't done anything good enough to warrant changing that."

That got Flash's attention even more. Luna had never denied him release, though she had told him to try not to make a mess. He gazed at Sour, at her self-satisfied grin, and could feel a sort of heat radiating off her. It might have been that she'd been working hard too, but he was sure it had more to do with her dominance over Rainbow. It was almost the same as what Luna shared with him, but a subtly different flavor.

Luna gave a little nod. "It's settled, then." She set the head of her racket to the court and held the handle upright. "Double-u or em?"

"Em," Sour said.

Balancing the racket between her thumb and forefinger, Luna spun it on its head. It turned and turned before a wobble made it start to fall. It landed on the court with the stylized letter on the handle upright. "We go first."


It was just before lunch and Flash was seriously starting to worry about losing. Rainbow had been amazing right out of the gate, but Sour was playing better and better with each game. Luna, too, was a great player (mostly thanks to her reach), but he felt like even the smaller section of the court she needed him to cover was too much.

"If we win this game, we have the match, pet." Sour seemed laser focused, but she spared a moment to glance over at Flash. "If you make your serve, I'll let you have some release today."

Gone was the strain of holding back what Flash knew were her darker moments. She was on-top of things and winning—even Sour Sweet had nothing to actually be sour about. With Rainbow serving, the game was in the bag unless Flash and Luna managed something amazing.

Watching Rainbow bounce a ball twice while she stood on the serving line, Flash felt nervous. Luna was facing her first, but soon enough he'd have to deal with her serve. The ball was tossed up and he barely saw her racket move before it connected with the ball and sent it hurtling to Luna.

Luna stepped back to let the ball bounce and lose some momentum before she brought her racket around and connected with it.

Watching with only his peripheral vision, Flash traced the ball over to Sour's off-side. She brought her racket back and, with both hands on the grip, looked directly at him. He'd played enough tennis in school to know that people looked where they intended to hit the ball. Shifting to his left, Flash anticipated Sour's return.

Just as she was about to connect with the ball, however, Sour let out a deep and guttural grunt of effort. The sound, plus being the focus of her attention, sent a shiver through Flash that locked him up—not for long, but just enough that he was slow to begin his swing. When he connected with the ball, his racket was still coming forward and sent the ball off the court to the side.

"Fifteen, love." Rainbow moved faster than even her serve to get the ball and get back to the baseline. She might be some kind of superhero, but in sport she never used her powers.

She bounced the ball once, twice, and a third time. Flash watched Rainbow's racket sweep backward and, for a second, all his attention was on two droplets of sweat that ran in rivulets down her arm.

"Ace! Thirty, love."

Flash slumped his shoulder at the call. He'd gotten distracted again and hadn't even seen the ball. "S-Sorry."

"Fleurette, dear, don't be upset. You're just a little too distractible today." The neutrality of Luna's tone made it hard for Flash to pick up on her emotion. "Either way, win or lose, I think we're going to have some fun." This had a positive vibe to it, and that alone had Flash smiling.

But smiles don't win tennis games.

Rainbow stripped off her wrist bands and approached the net after she won her serve and held out her hand to Flash first. Feeling a little self-conscious, Flash reached out as well and could see the sweat—now unbound—running down her arm. "Great game, Fleurette, Luna." She shook his hand first, then crossed to Luna.

That meant that Sour shook Luna's hand first. "Your little princess kept getting distracted." When she turned her attention on Flash, she pinned him with a look Flash recognized—it was the hungry look Luna had when she was in control of a situation. He almost melted under that gaze and, when her hand extended his way, he was almost trembling. "I think I can come up with something to cure that distraction."

"It appears I lost, but I don't intend to squander the opportunity to see another with similar views work." Luna turned her gaze to Flash, watching as he trembled under the attention of Sour. "Why don't our little darlings run along so we can discuss terms?"

Sour turned to Rainbow and Luna turned to Flash. He felt a little nervous about the whole situation and tried his best to smile for her.

"Why don't you join Rainbow in the lockers while 'adults' talk?" Luna asked him.

"Don't forget these, you dirty little tennis star." Sour passed Rainbow the clubhouse key with one hand and brought her other hand down firmly on Rainbow's rear. Giving Rainbow's rump a small squeeze, Sour let go and sent Rainbow hurtling toward the building.

Flash shook his head to clear his distraction and, racket in hand, tried his best to run for the clubhouse without flashing anyone with his skirt—he failed.


Author's Note

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