Lucky in Getting Lucky

The very real possibility that you've gone completely insane idly flits through your mind as you briskly made your way through the castle, adjusting your hastily donned mask.

Look, here's what happened over the last half hour or so: You contentedly listened to your sister loudly pleasuring herself as the giggling maid you just plowed waddled away, doing her best and failing not to drip a trail from the massive load of cum you dumped into her. Then, you quickly popped up to put on a goddamn Pink Zorro costume so you could *court* the aforementioned sister, all in an effort to seduce her into a real relationship with you, her real brother.

Also you fucked your aunt.

But all of that just makes you shrug? You remember being incredibly confused by all of this when you first awoke in this world, but that bewildered voice has faded away since then. Before, it was your entire stream of thought. Now it's more like a faint voice that occasionally pops up now and then, a sort of vaguely sighing commentary that pips up now and then to confirm that yes, this is crazy and you're crazy and fucking whatever you're going to do what you want anyway so who even cares fuck it. Is that voice what's left of who you were before you got pink hair and the hottest little sister in existence? That should concern you, right?

Well it doesn't. Even the little voice seems to be completely over it. Which is good because your plan is flawless, so the little voice can just cram it right up its...um, its voice hole. Or whatever. Whatever it has, and wouldn't want things crammed in.

You can sense the voice rolling its eyes at you. Just move on before you lose another argument with a theoretical disembodied voice.

Luckily by now you've reached the grand foyer, giving you something else to focus on besides your tenuous grip on what passes for reality around her. A maid greets you as you approach the massive double doors, a hippy little thing with a single dimple and monarch butterfly orange hair.

"Ah, Sir Sexbomb! Do you have a handkerchief that we might borrow?"

Probably. That seems like the sort of thing you'd have, anyway. You fish around in your pocket, choosing to ignore the way that the perky little ginger keeps shooting appreciative glances at your crotch. You're a bit maided out at the moment. Fortunately you do have a handkerchief, unsurprisingly a gaudily pink thing with "CANDYLAND" gracefully stitched onto one corner. Did Issa get these fucking things monogrammed? That is some next level commitment. The maid accepts the excessively rose-colored hankie with a grateful curtsy before opening the doors for you, indulging in a final eyeful of your bulge before you stride into the hall.

The rest of Ginny's suitors seem to have already gathered, quietly murmuring among themselves as their assorted entourages mill about with their various banners and scrolls and princely whatevers. You guess you should try to know these guys a little; they're theoretically your competition after all. Though honestly, even if you hadn't know a thing about Ginny, you wouldn't be that impressed with them. They're all generically handsomeish, and generically dashingish, but ugh. So bland. And dull. And you hate them.

Bleh, maybe you should try to give them a chance. A little one. The littlest one possible. Picking a prince at random, you slide up beside a very serious-looking young man with chin-length blonde hair and a scrawny valet. You clear your throat, prompting the prince to glance in your direction, eyebrows raised.

"Hey. 'Sup?"

The serious prince gives you a more or less gracious nod in response. Okay, maybe this isn't a terrible start. Maybe you don't want every other man who's ever looked at Ginny to be killed by fire ants.

"So. How about that princess, huh?"

He nods again, with what you're choosing to believe is regal sincerity. Well alright then, that's something! He doesn't have a chance in hell against you, you'll give the guy this: he's trying his best, and he's got great taste as far as your personal sisters are concerned. You're coming around on your new best friend.

"So hey, what drew you to the princess? Her gentleness? Her uniquely bubbly grace?"

The prince shakes his head, deigning to audibly respond this time. "I asked my herald which princess has the biggest breasts."

The moment you save Ginny from these fucking philistines is going to be the best moment of your life, but the exact moment this guy is killed by fire ants is going to be a very close second.

Fortunately for your former best friend the day's event seems to be starting, shelving your insect-based **** plots for the moment. The castle's herald waves you and the worthless buttholes who made up the rest of the suitors to silence from his position at the top of the stairs, the ginger-haired maid flanking him. Is she holding something behind her back? Better listen in to what the herald has to say.

The castle official clears his throat. "My lords, and welcome guests! Today, the Princess shall favor one lucky soul with the honor of escorting her on an upcoming country stroll."

The suitors immediately break out into excited chatter. You don't blame them; you still only sort of get how things work around here, but even you know that country strolls are the Princess equivalent of Netflix and Chill. These jokers shouldn't kid themselves though; there's no chance she won't choose you after all.

"And in the spirit of total fairness, her escort shall be chosen at by the hand of fate!"

Aw what? Man, FUCK the hand of fate! You hope the hand of fate is killed by fire ants! How the hell are you supposed to work your ingenious plan when things are chosen by the luck of the draw? You're in such a funk at this unexpected spanner in the works that you can only sullenly clap when Ginny appears to the enthusiastic applause of the rest of the room. You don't blame the monsters either; they actually have a chance for once. This total fairness is fucking unfair.

The herald raises his hands to call for quiet, trying to be heard over the excitement of the room. "And now, my lords! The lucky owner of the handkerchief that fate guides into Princess Genevieve's hand shall be her escort!"

He cues the maid with a nod of his head, prompting her to smile and present what looks like a large clear crystal punch bowl filled with all of the suitors handkerchiefs. The enthusiastic whispers die out with screeching abruptness as the entire room gazes up at the bowl, stuffed to the brim with dozens of identical white squares of cloth and a single flaring blaze of hot pink, so bright and out of place that it might as well have a spotlight on it.

Ginny stares bowl for a long moment, eyes wide as the other suitors audibly slump. At length, she clears her throat and calls out in an awkwardly loud voice. "Um, okay! I'm...I'm going to pick totally at random now!"

The herald nods along in self-satisfaction, seemingly the only person with no idea what's going on as Ginny sinks her little hand into the bowl. She doesn't even try to disguise her intent as she carefully digs around, plucking your practically neon handkerchief out from the others like the world's biggest and most obvious bullseye. She hands it over to the herald who officiously unwraps it, reads the monogram with far more care than he could possibly need, then raises his voice. "Princess Genevieve's escort shall be...."

The other suitors have already started huffily dispersing the herald holds for suspense.

".....Sir Candyland of Sexbomb! Congratulations to Sir Candyland!"

Ginny puts her hands to either cheek, trying her hardest to look surprised at this absolutely random turn of events. She probably needn't bother though, no one is paying any attention besides you and her. She apparently realizes this as she looks your way, her feigned incredulity shifting into a look of smoky anticipation. You stand, stuck dumb and utterly helpless as Ginny gives you a sultry smile, slipping a dainty finger between the bulging swell of her breasts to pull down the neck of her dress for you, favoring you with another couple inches of soft, delicious cleavage. Then, she gives you a wink, turns with a pleased flip of her skirts and prances away.

You don't know how long you keep standing there. Everyone else is gone, so that probably says something. Okay. Fuck. You've got to figure this out, got to clear your head. Where was that maid again?

The redheaded maid with the breeding hips groans in delight as you settle into a rhythm, bouncing the petite girl in your lap as she rakes her fingers down your back in rapture. Okay, now you can think. The problem, you muse as you take firm hold of the delighted maid's ass, is that things can't move too fast with Ginny and Sexbomb-You. Sexbomb-You is just there to run off the other suitors; it's You-You that's supposed to wind up your sister. Your sweet little sister, with her adoring green eyes. Your beautiful little sister, pert, fresh girlishness and soft, fertile womanliness in all in one perfect form. Your...

Okay, you still can't think clearly. The ginger maid lets out a moan of approval as you flip her to her back and pick up the pace, grunting in exertion as you thrust into her quivering folds. Fuck, it still isn't enough. Your heavy balls are practically churning but something is holding you back. You're trying to decide on a new position to try when that thought is interrupted by a tentative knock at your door, immediately followed by the soft voice that fills your dreams.

"Um, Big Brother?"

Okay, that was it. You're only surprised you can't hear your balls literally rumbling as an ocean of liquid fire begins bursting out from the deepest part of your loins. Better gasp out a response while you can still talk. "Ah, yes?!"

"I, er, was hoping you could do me a favor? Please? I have a, um....a date. Sort of."

The maid is polite enough to keep her climax to a strangled gasp as you begin unloading inside of her, your mind and body going haywire as you try to respond to your sister and creampie a maid all at once She apparently doesn't recognize the sound of a man trying to talk while explosively orgasming becasue she continues to ramble on. "But I haven't ever been on one. So I was hoping....well, that you could help me? Maybe we could...practice?"

You'd thought you were finished, but apparently not as this new revelation fires a final defiant rope of cum deep into the writhing maid. Somehow you manage to **** out a response. "You...want me to take you on a date? Dates? Practice dates?"

Ginny seemingly takes your stunned questions as agreement, because she sounds practically giddy when she responds. "Oh, Big Brother! Thank you so much! Oh, this is going to be so fun; just give me half an hour and we can go right away!"

The little voice reminds you that you must be the luckiest idiot to have ever existed, and you don't try to disagree. Still though. 'Practice' or not, in half an hour you'll be on a date with Ginny. Maybe you'd better get another maid in here real quick.