Usagi and Shingo by Imouto Kitten

Usagi Tsukino, still in her superheroine guise of Sailormoon, was 
returning to her home after she and the other Sailor Senshi dispatched 
the latest monster of the week. As her parents had grounded her for 
failing her latest test at school, she was forced to climb through a 
window to enter the house.

Not paying attention to her surroundings, she reaches for her brooch to 
undo her transformation when the voice of a young boy snaps her back to 
reality, "Sa-Sailormoon!? Wh-what are you doing in my room!?"

Looking around the room, the odangoed blonde quickly realizes this isn't 
her bedroom, and spotting her little brother Shingo sitting on the bed, 
concludes she made the mistake of climbing in his window instead of her 
own, rationalizing it as an easy mistake to make since their bedrooms 
are right next to each other and grateful that her brother doesn't seem 
to recognize her, but still finding the situation awkward and not sure 
if it would be better or worse if she had untransformed before entering.

Trying to think of an excuse why a famous superheroine would've climbed 
in the window of a total stranger, she notices what Shingo was doing 
before she invaded his private space. The boy had his shorts and briefs 
around his ankles, one hand curled around his little stiffy, and an open 
book spread accross his lap, a book that, even from this distance, she 
can tell is an H-doujinshi of some sort.

Deflecting his question, she grabs the book off his lap and asks, "What 
is this you're reading?" Going red as a tomato, Shingo is too 
embarrassed to respond, not that Usagi can see his reaction as she takes 
a closer look at his fap material. As she does so, her eyes go wide, her 
cheeks turn pink, and the crotch of her leotard grows damp with arousal 
as she comes face-to-face with illustrations depicting a steamy sex 
scene between herself and Tuxedo Mask. While she had long gotten use to 
the exploits of her and the other Sailor Senshi making the news, she 
never imagined that there would be anyone perverted enough to make porn 
of the Sailor Senshi.

Adding to her flustered state was the fact that, though they were madly 
in love and knew they were destined to be the parents of Chibi-Usa, 
Mamoru had made it clear that he wouldn't do anything overtly sexual 
with Usagi until she graduated from high school, and despite her 
pleading, she hadn't even gotten him to budge enough to slide a hand 
under her skirt or up her blouse when they made out, and here she was 
being presented with a scene beyond her wildest, frustrated virgin, wet 
dreams. At the same time, she was kind of flattered that her little 
brother was jacking off to her likeness even though she was sure he had 
no idea that Usagi Tsukino and Sailormoon were one and the same, and 
though her underdeveloped intellect knew it was wrong, the dominant 
thought in her mind was whether she could seduce her little brother and 
lose the virginity her boyfriend refused to take.

So, it is only half-hearted when she starts scolding him like she would 
a villain, "Such filthy reading material is completely unsuitable for a 
young gentleman. You should be ashamed of yourself for being such a 
naughty, little boy rotting your mind with such perversions instead of 
going out and earning the respect of girls your own age. In the name of 
the moon, I will punish you!"

Shingo gulps loudly as the superheroine he put on a pedestal as a living 
goddess of love, justice, and sexuality closes the distance between them 
and looms over him.

"What do you have to say for yourself, you naughty, little boy?" Asks 
Usagi, enjoying the power trip she's getting from watching her brother 
tremble in fear at being the target of his favorite superheroine's 
wrath.

Rising to his knees, Shingo then bows deeply, his palms and forehead 
pressing against the mattress, his cute, little butt sticking up in the 
air as he grovels, "Please forgive this lowly soul, oh powerful Moon 
Goddess, daughter of Tsukiyomi. I shall be your humble and obedient 
servant if you shall grant me mercy."

Though Luna had once told her the royal lines of the Silver Millenium 
were descended from the Gods that inspired the mythology of the Greeks 
and Romans, Usagi was still taken aback to see someone directing words 
of worship in her direction.

Placing a gloved finger under his chin, Usagi lifts Shingo's head so she 
can look him in the eye as she declares, "I, Sailormoon, guardian of 
love and justice, in the name of the moon, acknowledge your apology and 
your vow to serve me." Smiling mischieveously, she adds, "I will forgive 
you, and perhaps even reward you, if you can prove to me that you have 
what it takes to be a gentlemanly lover and aren't just interested in 
the pleasure you can get from women. Now, rise so I may get a better 
look at your equipment."

As Shingo rises to his knees, Usagi wraps one gloved hand around his 
shaft and cups his balls in the other, her little brother exclaiming, 
"What are you doing!?" as soft moans escape him as she strokes his cock 
and fondles his balls. She can't help mentally comparing his testicles 
to a pair of grapes and is pretty sure the handle of her favorite hair 
brush is slightly thicker and longer than his little cock.

"A bit small," she says teasingly before adding, "but I'm sure you'll 
grow nice and big as you mature." Letting go of his cock and balls, she 
lifts the front of her blue skirt, and guides one of Shingo's hands to 
the crotch of her leotard. As she rubs his palm against the damp fabric 
covering her virgin girlhood, she declares, "Your first test is to 
pleasure me with your hands."

Cupping the womanhood of the superheroine he's worshipped from afar for 
months, her juices coating his palm as her leotard fails to hold them 
and being able to feel that, as he had dreamed, Sailormoon wore no 
panties under her costume, was nearly enough to fry the young boy's 
brain, but he manages to stammer out, "Do-do you really want me to touch 
you... like this?"

Nodding, she replies, "Yes. I may be a warrior, but I am also a woman 
who has long sought a man's touch." Giving him another mischievious 
smile, she adds, "But proving your worth won't be that easy, young man. 
Unless I give you permission, you may touch me only with your hands," 
reaching out to grab his cock once again, she continues, "and you must 
be able to hold back your own climax until you have satisfied me."

As she resumes stroking him, he continues rubbing her through her 
leotard, no longer guided by her hand. However, kneeling on the bed 
face-to-face proves a rather awkward position.

Standing up, she commands, "Lie down." to which he immediately obeys. 
She removes his shorts and briefs from around his ankles to leave him in 
only a t-shirt and socks before discarding her own skirt.

As she straddles her little brother, giving him an excellent close-up of 
how her leotard conforms to every contour of her ass and girlhood, 
Shingo can't help commenting, "There's a beautiful moon out tonight!"

Squeezing his balls enough to be uncomfortable without actually hurting 
him, she replies, "I'll let that one slide since it was a rather nice 
compliment, but any more corny lines like that and I'll be tempted to 
give your voice a permanent falsetto." Releasing his balls and resuming 
her stroking, she adds, "Now, if you don't want to be punished for 
failing to put your partner's pleasure before your own, I suggest you 
get busy, and remember, you're only allowed to use your hands."
 
Trying to ignore the pleasure from having Sailormoon jack him off and 
fearing that he'll wake at any moment to discover that this was all a 
dream, Shingo starts running his hands all over Sailormoon's thighs and 
butt, oblivious to the fact that he's fondling his own sister. In 
response, Usagi moans softly at her brother's caresses, which are far 
more intimate than any Mamoru has given her and far more tender than she 
thought her little brother capable of.

After a minute or two, Shingo's hands converge at the spot between 
Sailormoon's legs. Pulling the leotard to the side, Shingo gets his 
first look at a real pussy. Usagi's labia are puffy and pink, swollen 
with bloodd due to her arousal, and glisten with her juices. Shingo 
immediately decides the doujinshi one of his friends managed to swipe 
from an older brother are a pale imitation compared to the beauty of the 
real thing. He inhales deeply, finding the scent imminating from his 
heroine's most precious place to be both heavenly and intoxicating and 
can't help wondering if she tastes as good as she smells, but fearful of 
what punishment would befall him if he disobeied the commandment to use 
only his hands, he settles for running a finger along her slit, and 
smiles to himself when he feels her shiver in pleasure at the touch.

A few more swipes along her slit with increasing pressure, Shingo finds 
the opening to Usagi's vagina and slides his index finger inside her, 
managing to get all the way to the third knuckle without trouble and 
marveling at the warm snugness surrounding his digit.

Enjoying the sensations as her brother's finger starts sliding in and 
out of her and wondering if he's attracted to her, or just attracted to 
sailormoon, she asks, "Do you have any sisters, young man?"

The question catches him a bit off guard, but fearing that he'd be 
punished if he doesn't answer, he replies, "I have an older sister named 
Usagi."

"What is she like?"

"She's really annoying, but I think she might be one of your fangirls 
since she wears her hair in a similar style."

A bit annoyed at being accused of copying her hairstyle from Sailormoon 
since she's been wearing her hair in pigtails with odango long before 
she ever met Luna and knowing Shingo should know that, Usagi bites back 
her annoyance as she asks, "Is your sister good looking?"

"She'd be beautiful if she didn't have such a grating personality, but 
even if she was nice, she'd be nowhere near as beautiful as you, 
Sailormoon!"

"Have you ever peeped on her when she was in the shower or changing?"

Getting nervous at her questions, he replies, "N-no, of course not."

Squeezing his balls again, she replies, "You're not lying to me, are 
you?"

"Okay, I'll admit that I've been tempted to peep on her in the shower, 
but I swear on my manhood that I never actually did it out of fear she'd 
crush my balls if I got caught!"

Admitting to herself that she probably would've crushed his balls if she 
ever caught him peeping on her, she replies, "I'm glad to hear you have 
some decency." Thinking a bit, she asks, "What do you think of the other 
Sailor Senshi?"

"All of you are beautiful in your own ways, but you're by far the most 
beautiful, and only Chibi Moon beats you for pure cute factor."

Curious if her brother has been lusting after his niece, she starts to 
ask, "Do yo-" when his exploring fingers locate her G-spot and clitoris 
and she's forced to cover her mouth with a hand to avoid letting out a 
moan that would be loud enough to draw the attention of their parents.

Noticing the strong reaction that got from her, Shingo tries to 
replicate it and before Usagi can recover from that initial shock, her 
brother's index finger and thumb are vigorously rubbing at two of her 
most sensitive spots and she completely forgets about jacking off her 
brother as she tries to contain the waves of pleasure washing over her. 
This proves to be Shingo's saving grace as Usagi had him right on the 
verge prior to his discovery.

Before long, Usagi is experiencing the strongest orgasm she's ever 
known, both hands clamped over her mouth the only thing muffling her 
pleasured scream enough to not have her parents barging in and having 
Sailormoon arrested for molesting their son, her pussy tightening like a 
vice around her brother's finger.

As soon as she's recovered her senses enough, Usagi bends over, giving 
Shingo an even better vantage point for looking at her nether regions 
before she engulfs his stiff, little cock and is almost immediately 
rewarded with a mouthful of salty, pubescent boy essence.

Once done swallowing the first load of cum she's ever milked from a boy, 
She straightens and says, "You performed admirably, young man. Are you 
sure this was your first time pleasuring a girl?"

"I swear I've never touched a girl before!" Blushing, he adds in a near 
whisper, "Besides, other than my mom, sister, and cousin, I have trouble 
even talking to girls."

"You said earlier that you thought your sister was annoying. Is that 
despite being nice to her, or do you annoy her in turn?"

Looking abashed, Shingo replies, "Well, I guess I'm a bit of a brat to 
her sometimes."

"Would you like to lick my pussy?" She asks, thinking of how she can get 
him to better behave.

Taking the sudden change of topic in stride, he exclaims, "I'd love to!"

Smiling at his enthusiasm, she declares, promise me that you'll be nice 
to your sister from now on, and I'll let you lick me to your heart's 
content."

"I promise!" cries the boy, and being as eager to be licked as Shingo is 
eager to lick her, Usagi doesn't hesitate as she pulls her leotard to 
the side and sits down on her brother's face, moaning in ecstacy as he 
plunges his tongue deep within her.

She's not sure if it's due to her lack of experience, Shingo being a 
natural at cunnilingus, or if the boy actually picked up some tips from 
the hentai he's been reading, but she enjoys being eaten out even more 
than being fingered, and it isn't long before Shingo is bringing the 
blonde to orgasm once more, her juices spraying all over the boy's face.

As she catches her breath, Sailormoon comments, "Not bad, kid... I think 
you've earned the ultimate reward."

As she gets off the bed, the body of her uniform glows brightly as she 
wills the garment to vanish, leaving her in only her gloves and boots, 
the sight of his goddess in such a state of undress nearly making the 
young boy lose his load without being touched.

Noticing him staring and thinking his erection looks a bit straighter 
than before, she strikes a pose and asks, "Like what you see?"

Nodding vigorously, he replies, "I love what I see!"

Smiling widely, she pulls him to his feet and pulls his t-shirt up over 
his head to leave her little brother completely nude before her.

Sitting on the edge of his bed, she lays back, placing his pillow 
between her head and the wall before spreading her legs wide and using 
her gloved hands to spread her labia.

"Now, I want you to stick your little stiffy in here," she declares, 
pointing at her virgin opening, "but there's one rule. You aren't 
allowed to cum inside me. When you feel like you're ready to squirt, I 
want you to pull out so I can swallow your cum again."

Walking up to the bed to find that Sailormoon's pussy is at the perfect 
height for him to enter her while standing, he lines up his tip with her 
opening and declares, "I promise I'll pull out!" Before thrusting his 
hips forward to bury himself in his sister's folds.

Usagi had expected losing her virginity to be painful, but thanks to 
Shingo being so much younger, and thus smaller than a boy her own age, 
his slender cock manages to slip through an opening in her hymen without 
tearing it, allowing her to enjoy having a boy's cock inside her from 
the beginning.

As Shingo unknowingly hilts himself in his sister, his member is 
engulfed in a warm tightness beyond his wildest dreams and it takes all 
of his will not to break his promise immediately. After recovering from 
the overwhelming sensation of losing his virginity, Shingo slowly 
withdraws before sinking balls deep within the woman he idolizes once 
more.

The slow pace Shingo sets out of worry that he won't be able to stop 
himself from cumming inside is agonizing to Usagi and she shouts, "Fuck 
me faster!" as she wraps her legs around his waist and starts bucking 
her hips in time with his. That's all the encouragement he needs and soon 
the siblings are frantically pulling apart only to slam their hips 
together again over and over in sync, both working hard towards a much 
needed climax.

And then it happens. As Shingo feels himself nearing the point of no 
return, he freezes and tries to pull out, but Usagi, still lost in lust, 
continues bucking her hips and her legs are hugging him too tightly to 
allow him to escape. Desperately trying to hold off his orgasm, the 
mental images his mind conjures of what she'll do to him if he cums 
inside doing little to dampen his arousal or dissuade his penis from 
fulfilling it's biological imperative of delivering life-making seed to 
the likely fertile womb before it.

Terror in his voice, Shingo pleads, "Sa-Sailormoon! I need, I need to 
pull out!" His voice breaking in panic, he continues, "If you don't let 
me pull out right now, I'm going to shoot my load inside you!"

But his words fail to penetrate the fog surrounding Usagi's mind, her 
own body too focused on her own impending climax as she pulls her little 
brother into a hug, smothering his face between her breasts just as she 
starts trembling in orgasm. Her pussy tightens like a vice around his 
small member, trapping him within her even if he wasn't trapped by her 
limbs. This is too much for Shingo as his cock erupts deep in the 
heroine he worships, the heroine that, unbeknownst to him is his own 
sister.

It is by far the most intense orgasm Shingo has ever had, but even as 
his sister's pussy repeatedly clenches around him, milking his cock and 
balls for every last drop of sperm-filled semen and sucking it all into 
her womb, he is unable to fully enjoy it as thoughts of 'Oh fuck, oh 
fuck, oh fuck!" run through his mind. 'I'll be lucky if she gives me a 
quick death, but she'll probably torture my cock and balls until I'm 
begging for death!"

As Usagi returns to her senses and finally releases Shingo from her 
grasp, the boy stumbles back, terrified of how she'll react.

Glancing down and noticing her brother's seed dribbling from her no 
longer virgin pussy, she starts to tear into the boy, "I told you not to 
cum inside and you promised you'd pull out!"

Deciding groveling and the truth are his only chances of getting out of 
this with his boy parts in tact, Shingo drops to the floor and begs, 
"Please forgive me! I tried to pull out, but your majestic legs are as 
strong as they are beautiful! I couldn't break free of their grip and 
you seemed to not hear my pleas to let me go! I tried to hold out, but 
my mortal manhood was no match for your Goddess Girlhood!"

Thinking back and half remembering him saying something she was enjoying 
herself too much to pay attention to, the heroine looks abashed as she 
declares, "Well, I guess you can't be blamed if I was enjoying myself 
too much to let you uphold your promise." Crossing the room, she kneels 
before him and gives him a kiss on the forehead, a kiss on each cheek, 
and finally a kiss on the lips. Giggling at the blush this produces in 
him, she says, "Now, don't go bragging to your friends about this 
encounter. A gentleman never kisses and tells, and we did a lot more 
than kissing."

"Of course I won't tell anyone!" he replies, silently adding, 'not that 
anyone would believe me if I told them I lost my virginity to 
Sailormoon.'

Not bothering to rematerialize her costume, Sailormoon heads for the 
window, saying, "If you're nice to your sister, she might offer you the 
same pleasures you've enjoyed tonight." Before giving him a wink and 
jumping out the portal.

As she creeps along the wall to her own window, Usagi is torned between 
hoping she doesn't get pregnant from what just happened and thinking it 
would serve Mamoru right if another boy knocked her up because he was 
too noble to give her what she wants. Either way, she can't help 
wondering how she can arrange another such session with her little 
brother without letting her secret slip.