Not a Date
Chapter One: "But Maybe One?"
•····················•····················•····················•····················•
Standing at the small flight of stairs leading up to his crushes home, Herman gripped his little tux collar and bundled the fabric in his hand. Instead of butterflies fluttering around in his stomach, the boy felt himself filling up with dread. All those scary three steps loomed and swayed in a hazy vision of fear in front of Herman's eyes. The bouquet of red roses in his hands shook violently. The shaking only grew worse as the cheap plastic wrapping of the bouquet became slick with sweat. It almost slipped out of his nervous fingers.
Herman's eyes were clenched shut and there was a slight ringing in his ears.
Actually it was just the doorbell he had unwittingly pressed. He silently cursed his body for moving on its own.
It took a painstakingly long time to even hear footsteps coming down the stairway from inside. It wouldn't be surprising if they had already seen him out the window and deliberately made him wait.
The door finally opened slowly, and Bailey slumbed. She leaned on the handle, looking slightly disgusted at the sight of her one-sided crush in a tuxedo.
"H-Hi Bailey," Herman stuttered like crazy, and somewhat forcefully pushing the bouquet of roses at her. "I got you these! Wanna go on a-?"
The girl took one look at the flowers and groaned, loudly.
"Ugh… I HATE roses…"
Swallowing hard, Herman muttered an apology as the words sliced his heart strings. He hadn't even gotten the chance to ask her the real question on his mind. Even if there was no doubt in that the tux had given it all away at first glance. The girl's eyes looking him up and down gave away that much.
"I-I am so s-sorry…"
"It's fine, Herman. I wouldn't have expect anything different from you…"
Herman bit back a whine. "Uh, s-so I wanted to ask you… If... um,"
"Herman, for the forty-sixth time I do not want to go on a date with you!" Bailey cut him off with a groan. "Look, we're friends and all, but I would rather go for your brother than go out with you. BUT since you took the time to dress up like THAT, I guess you could come watch this awesome new horror movie with me!"
"D-don't dates usually go and watch horror movies?" The boy squeaked.
Bailey grunted and dragged him inside, slamming the door shut. Her grip didn't relent as she rushed past her parents in the living room before the camera could snap a photo of the 'happy couple'.
The pair went straight to Bailey's room, and Herman found himself almost shoved inside.
While the young teenager had been expecting overly pink or full of pranking supplies, it was a surprise to see just how his crush lived. A comfortable looking hand-shaped chair was set up close to the TV, while a small tattered bean bag was being tossed onto the floor for Herman. Even the bright pink duvet looked more appealing than sitting on that ratty thing in a horror movie. It looked like a pair of zombie's hands would reach out and snag him at any moment!
"Let's just get this movie over with." Bailey said with venom on her tongue.
The pair sat in silence as the cheesy horror movie started; Another cheap zombie movie lead by a muscle-bound manly man protecting some skimpily dressed woman who couldn't do anything but scream. Not surprisingly, both young teens were bored out of their minds, up until the makeout scene that had both their attention.
"That is so fake! She doesn't even like that guy, he's a total weirdo." Herman groaned. "He ATE a zombie dog!"
"And still looks better than you… but hey," Bailey couldn't help but insult the younger boy: "Now you know how your future girlfriend is going to feel about having to put up with you…"
Despite wanting to glare slightly, Herman smirked instead.
"Don't you mean you, Bailey dearest?"
"Ew. I bet you wouldn't even know how to kiss a girl, let alone date ME!" Returning the smirk, Bailey made out sloppily with her hand. Herman wanted to slap himself for being jealous of the hand.
Not willing to let the challenge go, Herman almost tackled the girl and pushed their lips together in a needy kiss. With Bailey's eyes widening and not kissing back for a few moments, before finally giving in. It wasn't long before they melted into the awkward, rushed kiss. Herman's tongue attempted to enter Bailey's mouth which was promptly, and accidentally, bitten by the curly-haired girl. While he wanted to scream from the bite, Herman didn't want this to stop. He had been dreaming about kissing Bailey, ever since he stopped seeing her as just one of the boys and noticed her beauty as a girl.
On the hand-chair, Herman felt awkward sitting on Bailey's lap. To gain some leverage, his hand cupped her face and side to pull her in closer.
"S-so forward, little Hermie…" Bailey breathed in between liplock.
After a few kisses, Herman hand made contact with the girl's top. Causing both of the young teens to blush heavily at what was possibly coming. The pair locked eyes as Herman nervously tugged at Bailey's thin white tank top.
Not wanting to do anything without the permission of his hopefully future girlfriend and his current 'date', Herman nervously asked what he wanted: "B-Bailey… c-can I remove this?"
The girl's face turned a shade more red at the question. It was never planned on Herman seeing her perky tits, so decided that he would have to show his first. Even if there wasn't much there to see on his pale little body. Playing with the cute tiny bowtie around her 'date's' neck, Bailey whispered. "O-only if I can take off this first…"
"My bowtie?"
"Y-your shirt, dumbass!"
Herman puckered his lips and nodded nervously, hoping that his chest wouldn't be bad enough that Bailey would laugh.
Bailey eased the buttons out, letting the fabric loosen and bring more of Herman's slim undefined chest come into view. He had yet to grow any hair, leaving him pale and smooth. While Bailey was more for older-looking guys and would have loved at least a thin snail-trial of hair to Herman's crotch, which she guessed would also be hairless. Or at least thin. She found herself smiling nonetheless. Her eyes raked his young body from his small, barely noticeable nips to his outie belly button. His nipples were so light and pink that Bailey couldn't help but giggle to herself.
She could no longer fully say that she wasn't interested.
"W-Well what do y-you think?" Herman questioned, blushing as the girl of his dream checked out his young, hairless chest.
He flexed his thin, stick-like arms and puffed out a little to seem impressive.
"Well…" The girl looked for the words. "I can't say that i'm surprised. But it's cute, really cute Hermie…"
The word was like a dagger to the heart.
Cute.
What filth. Cute was reserved for puppies and babies, not men.
"W-wh-what do you mean cute? I thought I was one of those, uh..." Herman struggled to remember the word Chance had used last time they went skinny dipping. Not that anyone wanted to remember going skinny dipping with Chance. "S-sexy twinks! N-not cute…"
Giggling slightly, Bailey couldn't help but question him: "Do you even know what a twink is, Hermie?"
Not wanting to seem like a noob, Herman responded: "Y-Yeah?"
"Then what's a twink, Herman?" Bailey pushed. A finger trailed her 'date's' smooth chest, making him shiver and jump.
"Um? A super sexy stud?" Herman blushed, fighting back a moan as Bailey's finger traced his smooth young chest.
She just laughed and traced a finger up and down her 'not date's' body. Loving the way he twitched and breathed out a tiny laugh at the light touch and her fingers playing with the light pink nubs. Bailey pulled the boy back down onto her lap and poked his nips with an innocent smile. "No, Herman! A twink is a young, small, smooth and sexy or cute boy. You are young, smooth and soooo cute Hermie! So nope, no studs here. Just my twinkie Herman..."
Herman couldn't help but blush from the comment.
"N-not that I find you cute or anything… Just, um… n-not sexy." Bailey blubbered, trying not to let him see her blush.
An action achieved by pressing their lips together for another heated moment. Not as awkward as their first, as now neither's tongue even attempted to move in fear of a bite.
"Wow…" Herman whispered softly, as their kiss broke.
"...Yeah… wow," Bailey repeated.
"S-so does that mean we're…?" Herman's eyes suddenly were panic filled as his eyes travelled down to his hands.
The pair of young teens hadn't even noticed the pair of hands that had slipped unconsciously up Bailey's shirt and were palming her small breasts. Even small and perky as they were, Herman's small hands were filled by the little tits and nipples poking his palms. The sudden groping didn't matter as they kissed again, with Herman giving them a gentle squeeze that made her moan into his mouth. While she wanted to protest a little, but the softness of Herman's hand on her small breasts was getting to her quickly. One hand teased the nipple a little with a slight twist that made Bailey yelp.
"S-sorry…" Herman muttered when the kiss ended.
Bailey fell silent and made him stand up, before moving and lying down on the duvet. That look in her eyes drew Herman close, and the boy straddled himself over the girl. Almost instantly the boy's hands moved back to her sides, pinning her down with his body weight. "I guess the Mongoose wanted what it wanted. Can't control the Mongoose when it's hungry,"
"W-Who said I was mad at the Mongoose… Hermie?" Bailey blushed. The young girl not ready to admit out loud that she wanted his hands back on them.
Biting his lip slightly from making Bailey blush. The thirteen-year-old leaned in, in order to gave her a quick, innocent but loving kiss.
"C-can I… um… t-take it off now?"
A nod from the girl of his dreams, had the mongoose internally beaming.
The thin white tee easily slid off her thin form, although in the awkwardness of the moment Bailey almost elbowed Herman in the nose. Herman hadn't noticed however, with the boy's full attention on what he was revealing. Bailey's small breasts, covered just by a small white lacy bra.
Unwilling to say anything, Bailey placed the boy's hand to her right breast. Almost instantly he squeezed, as if testing how soft they were. An action that had Bailey releasing a small soft moan. Blushing from the action, Herman used his fingers to lightly massaged Bailey's right breast through her bra.
He was taken aback by how firm the petite bumps were, wondering if they would grow softer as she aged. With the boy knowing that his mother's weren't anywhere near this firm.
The negative of his room sharing a non-soundproof wall with his parent's bedroom.
As his fingers rubbed against her sensitive nipples, Bailey breathed out; "O-Oh god… Hermie…"
"You look… uh…" Herman blushed, with the words catching in his throat. "Um, r-really hot? B-bailey,"
"T-Thanks…?" Bailey blushed, while moving her hands down to rub against Herman's crotch.
She couldn't help but grin at his adorable moan from the simple touch.
Herman grit his teeth and bit back the soft moans forming in his throat. The boy was determined not to come off as 'weak' in front of his crush, to show just how tough he was. A light touch on his crotch wouldn't make him moan. Yet in reality, it was making him want to explode then and there. Right in his shorts, maybe even leaking out onto the palm of Bailey's warm hand.
Something that would embarrass him to no end.
He didn't want Bailey seeing him as a quick shooter.
"Why don't you take those off too, Hermie? I wanna see what this is like. I've never seen one up close like this." Bailey pouted, tugging at his shorts. "Come on, take them off! P-please Hermie?"
Lifting up his hips, Herman eased both his shorts and small tightened boxer briefs down his thin smooth legs. After kicking the fabric off, he lowered down and Bailey felt his length pressing down on her own crotch. A feeling that had her blushing bright red, as she felt one against her for the first time. As Herman lowered himself, Bailey took in the view of the first boy that she had ever seen naked. His thin, neatly trimmed bush perfectly framed the some four inches of his young, pale-pink dick.
While he was loving the idea of Bailey checking out his naked body, a blushing Herman wanted to see her.
Actually, the mongoose was craving it.
"I-I wanna take off your clothes!" He almost blurted out, taking the girl by surprise. He wasn't even sure if she could get any redder. "Bailey…?"
"Yes! T-take them off…"
The boy moved down to the end of her bed so that he was nestled between her dark slender legs. He could see up her skirt, getting a good look at her white panties - already wet with her young juices. He was all too eager for a taste, so didn't wait for her to lift her hips before stealing the clothes away from her body.
His eyes widened at the girl's nakedness. The first time his striking, lion-like brown orbs took in the exposed body of a girl. He licked his lips, staring at the pink between her light brown skin. Its juices leaking out onto her sheets instead of his eager tongue.
"You're so hot, Bailey… I've wanted to taste you for so long…" He muttered aloud, slowly lowering on the girl and stealing a taste of her sweetness.
"Mmm… O-oh fuck, Hermie! Y-your tongue…" The girl moaned as the untrained tongue lapped at her pussy.
Herman was fast and uncaring to his partner's pleasure as his overly eager muscle worked her hole, eating her out with no grace. It wasn't long before she pushed him away with a slight glare.
"Herman! Didn't you hear me saying stop!?" Bailey snapped. Trying to hide the fact, she had been getting close to releasing her juices onto the cute boy's face from the boy's untrained laps of her young pussy.
"N-no?"
"Ugh, boys…" The girl muttered. Then she maneuvered Herman on top of her again, cracking a smile at that adorable, cheeky face of his. Her hand guided his to the clasp on her bra, "Take it slower. Treat a girl like a flower, and be gentle…"
'Did she just call herself a flower? She hated the flowers I gave her…'
Nevertheless, Herman struggled and fiddled with the clasp as he wondered why she even needed a bra. Bailey's breasts were small and flat, definitely leaving it all to the imagination.
"Ngh… this thing's too hard Bailey!"
Bailey groaned slightly in annoyance, muttering 'boys' under her breath. The boy growled as he continued to struggle with it, before finally sighing in relief when he was met by a satisfying 'click'.
Revealing a pair of firm young breasts that had his young cock throbbing.
Her dark brown nipples and areola stood out against her light-brown body, small and firm as Herman slightly cupped them. His fingers fiddled with those nubs, gently pinching them and giving them slight tugs.
"H-Her-Herman…" Bailey moaned out, from the teasing of her sensitive nipples.
In the boys distraction, his dick grinded against her thigh and prompted moans from the pair. Every so often, in between kissing or Herman taking a hesitant taste of her breasts, his dick would rub against her pussy. As the head became slick with her sweet juices, Herman thrust inside during a deeper kiss.
Bailey's eyes almost bulged, with the girl screaming into the deep kiss as her virginity was taken by Herman Baldwin.
He swallowed her scream of pain as a few inches entered her no-longer virgin hole and stretched her wider than ever. In his panic, he stopped moving and did the only thing he could think of to comfort her: Keeping on making out.
"Mmmph! H-hermaaaan!" She managed around Herman's lips, with a single tear.
Not liking the sight of a tear, Herman broke the kiss in order to press his lips against the leaked tear.
"Are you ok, Bailey? D-do you wanna stop?"
"N-Ngh-Noooooo…" Bailey whispered, as she felt Herman's young cock twitching inside of her tightness.
Herman didn't hear the question, too focused on the feeling of Bailey's young pussy hugging his cock.
"Ahhhh! God B-Bailes… you are s-so tight…"
From her mirror on the other side of the room, Bailey could see Herman's bubble butt flexing as he thrust deeper into her wetness. She giggled, despite the pain, at just how cute the boy inside of her was.
"I… I… the Mongoose... can't hold it long inside of you… t-too tight!"
Bailey flushed red as her legs wrapped around Herman's waist, pulling the boy in close and making him thrust deeper into her wetness. Their lips crashed together, in a young and somewhat sloppy deep and passionate kiss as their tongues danced to no rhythm.
Blushing, Bailey admitted "I'm close too Hermie… D-don't do it inside me… I'm n-not on the pill…"
"NGH! F-fuck I'm gonna cum, Bailes!" The boy grunted.
After a few more sloppy thrusts, Herman slipped his cock out of Bailey's pussy. The boy found himself quickly beginning to hump against her, with his cock grinding against her young hairless pusssy. Their young, naked, sweaty bodies grinded together until his cum was shooting between them. He was moaning loudly as his body shook with one of his first non-watery orgasms. Bailey's legs were shaking slightly, with his thrusting having pushed her over the edge as well. His dick pressing against her pussy and clit was making her moan through the experience. Panting heavily and sweating from the experience, the cum covered Bailey cuddled into Herman's naked body. Smiling, Herman grabbed her pink duvet and pulling it over them before cuddling the girl of his dreams with a spent smile on his face.
The pair drifted off to sleep in that position, with Herman's arms wrapped around the cum covered girl of his dream.
Before she drifted off as well, Bailey whispered. "Y-You know… Hermie… I… I… It's still not a date…!"