Yuta is the lucky loser

"Um, this street..." was all that Yuta said as Gum was finishing up her latest wad of her namesake, spitting it out onto the sidewalk to signify that she was about ready. The gorgeous young woman was posed over her lime green bike with one foot leaning up against the wall next to her, so as to give Yuta (and anyone else who happened to be nearby) a good look at her shiny green underwear.

"Yeah, yeah, I know you're eager, but I'm banned from most of the convenience stores around here and I didn't want to waste a fresh chew. I'm ready now." Gum said, hopping onto the contraption and settling her mostly-uncovered butt on the seat. If it was a long run she would've changed into pants, but a little chafing was worth it for a short distance, just for the free advertising.

"But isn't it a little crowded?" Yuta asked, his voice quavering, as he looked at the teeming sidewalks and car-filled streets ahead. "I'm worried I'm gonna hit somebody."

"Yeah, duh," Gum said, blowing air through her lips. "That's the point. A straight-line race on a track is just boring. Hitting the randoms is the main way you're gonna get slowed down, but if you play it too safe you don't have a chance. Don't worry too much about it, if there's a collision just steady yourself out and keep going. Now, since you're paying for the challenge you need to trust that it's fair, since I know these streets and all. So at the first corner and the brick wall where we turn around and start the return circuit, I'm going to spray a fresh green dot of paint." She tapped the spraypaint can jammed into a holder made for a water bottle on her bike. "Look, I'm not even making you hand over all the cash in advance, just half. Don't be a wimp... you said you were good at sports and racing? Show me."

"But I didn't bring a helm-" Yuta didn't get to finish his sentence before Gum pushed off and rocketed down the street, picking up speed and making a group of three schoolgirls walking in a line shriek in alarm and dive out of her way.

Something seized hold of Yuta as he saw Gum's unbelievable curves disappearing from view. He wanted... he lusted... he couldn't bear to see her just disappear like that.

Gum looked back over her shoulder, slowing down slightly. At first she thought the kid had given up but then she noticed that, no, he was actually going right down the street, blowing past oncoming traffic! His bronzed, muscular legs pumped like pistons as he traded speed for safety, swerving far to the side and taking a winding path to stay as far away from both cars and pedestrians as he could. Gum was far more confident - as she looked forward she decided that, being one of the founding GGs after all, SHE had the right of way in her own turf, and anybody in her way needed to get OUT of it. In fact, during the rush she noticed a particular foul-mouthed blonde bimbo who fancied herself some kind of scientist or other nerd crap like that who had encroached on GG territory before, and Gum aimed AT her, making the bitch dive aside, skirt fluttering in the air, and curses ringing in her ears.

Amazingly, despite not knowing the streets, Yuta did far, far better in keeping up with Gum than the average dude who 'challenged' her like this, even the ones who didn't know they were supposed to lose. As fit as she was, it wasn't that hard for a really athletic guy to beat her if he put his mind to it, and it seemed like this kid was a downright speed demon, in addition to being thickheaded enough to try. Maybe she'd have to get even less subtle about it in the future.

But even though Yuta was really pouring all he had into it, his stubborn refusal to cut close to pedestrians meant that he could reduce the lead Gum had from her head start, but not overcome it. She had time to spare to make paint dots at each of the checkpoints and, on the way back, decided to even ramp over a culvert, doing a flashy jump.

She had already dismounted and popped a fresh stick of Bubblicious in her mouth by the time Yuta came to a halt by her in the alley they'd used as a starting line, panting heavily. He looked really crestfallen.

"So... hahhhhh... I... guess... that means I don't get my name on the... haaaahh... board or get to meet Mew again..?"

*POP*. "Nope," Gum said. "I mean, there were a couple of moments where I was a little bit worried you'd pass me. Maybe. But challenging the freestyle queen - that's Mew, remember - means she gets to choose the type of challenge. And no matter how cute and girly you think she is, I promise you, she would grill you like yakitori on skates."

Yuta ran a hand through his brown hair and kicked a discarded coffee can. "...Darn. Well, I guess a deal's a deal so I have to pay up... There goes the rest of my summer cash, more or less..."

"Yup." Gum said flatly. Well, since he seemed to be taking it well... she stepped closer to Yuta but rather than hurrying him in getting his wallet out, she pressed her chest up against his shoulder. Squish. That made Yuta's hands go all nervous, and he fumbled as he tried to get out what he was going to forfeit to her. Her pride was at stake now - even after all that, and staring at her butt on that bike the whole way, he was still disappointed he wasn't going to get to see that cutesy little piece of candy, Mew?

"So since you were a good sport I could go ahead and put you up on the board anyway, and promise to let our current freestyle queen know you want another match up with her. But... I could also put your challenge fee towards another way you could show your stuff. Right here in this dusty back alley."

"How is that?" Yuta asked, curiously - clearly having to make a serious effort to keep his hands to himself.

"Well my specialty happens to be art. Visual art, not on ramps and half-pipes and stuff." Gum said, smacking her lips loudly a few inches from his ear. She slid her hand under his jacket and traced it down the front of his stomach. Damn, she thought to herself... short though he may be, this Yuta sure was fit. Way better than the average she ended up dealing with and offering her little secondary challenge to, here. Even if he was willing to just pay up and leave it seemed like a shame to make him do so.

"You mean graffiti?" Yuta said, curiously and without a hint of judgement. "Damn right I do." Gum said with a defiant toss of her head. "Like, cops and people make it out to be a bad thing, as if beautiful designs and colorful tags are uglier than a bunch of bare bricks or concrete?"

"Well... I guess it is kind of like a public service. Beautification of an urban area or something." Yuta smiled.

"Yeah, we're on the same page. So even though you have way, way less chance, I'll go ahead and make this a two part challenge and let me show you what you can do there. Plus, this way I can see if you're actually cool with us or if you're still just a mama's boy afraid of doing any little thing that would make the authorities wag their finger at you." She pushed a fresh can of blue paint into Yuta's hand and pointed to the nearby wall.

"Wow... um..." Yuta looked at the wall, then back to Gum's enormous tits leaning right towards him. "I guess I can always clean it up later if the owner of this place wants it removed... and I've taken a few painting classes..."

"Cool. So, you can go first. But this is still a challenge, and the real skill of a street artist is in working with distractions. Always wondering if someone is gonna come bust you while you're doing it, you know? Usually it's a lot less private and safe than a blind alley like this." Gum said before blowing another bubble. "So part of the challenge is that whoever's painting has to deal with any distractions the other one can think up, so long as it doesn't pull them away from the wall or mess with their arms."

Yuta had already been uncapping the can and about to start. As he half-turned, he was about to ask when the vivacious blonde pushed right up against his back, squishing her oversized breasts (which were quite natural as Yuta could clearly feel) up against his shoulderblades. Without warning, the green-nailed fingers of Gum's hand slipped beneath Yuta's waistband and into his underwear, feeling that he was already quite excited.

"I got a 10 minute stopwatch going. You better get started." She put her gum in her cheek for a moment to give him a long, lascivious lick from his ear down the side of his neck. Her hand got right to business and wrapped around his erect shaft, starting to jerk back and forth.

Speechless, Yuta trembled as he started making a long blue curve on the wall. Was this really going that direction?

As Gum kept pumping her hand up and down his shaft she started imagining what it might feel like. A lot of the times guys didn't last long with either of her usual routines even when she just used her hand... but she wanted to give this cute young guy a good experience, so she kept going slower than she otherwise might. Soon her hands were undoing his pants and unzipping them, letting them drop down around his ankles.

"Ooops." Gum said casually in her usual flat tone of voice, looking over his shoulder to appreciate the big cock on display. "Well, I guess you have to worry about getting drips of spraypaint on your dangle now. That's one of the reasons it's important to keep the right pressure on the nozzle. But, maybe I should help you out a little."

Before Yuta could ask what she meant, Gum had wriggled her way in front of him - but she squatted down low to the ground to avoid blocking him from accessing the wall. The bulky white helmet loomed closer to his hips... "Wow, uh... I never asked you what I should write, or draw..."

"Listen to your heart." Gum said, blowing a bubble again... but this time she pushed it forward so that it squeezed against the head of Yuta's cock, the pink bubble going over the straining purple head before eventually popping, leaving a sticky strand between her lips and his meat. Rather than pull it off, Gum took the opposite approach and leaned forward, eagerly slipping her lips over the head and shaft of Yuta's manhood. Her nipples were poking lightly against his tanned thighs as she wrapped her arms around his lower back, running her tongue all over his shaft as if trying to retrieve the bubblegum stuck to it.

Gum thought to herself that despite the humiliating position, something about this Yuta was really getting her excited... Soon, she took one of her hands off of him so that she could slip it down between her thighs and begin rapidly running two fingers over the crotch of her green panties as she squatted with her knees apart. Yuta's eyes were rolling back in his head and his hands moved in broad, uncoordinated sweeps like the stumbling of a sleepwalker. The sound of traffic seemed to fade to nothing in his mind, replaced by the noisy slurping coming from has crotch as Gum showed him what it was like to get a blowjob from a chick with such an oral fixation that she'd been nicknamed after it.

Although Gum braced herself to get a load full of bitter juice in her mouth any second, it seemed Yuta's attempts to focus were delaying him from cumming, and he was still rock hard and eager when the stopwatch beeped. Peeling a sticky strand of bubblegum off Yuta's cock with her fingers as she finally pulled back, Gum noted that she should've gone a bit easier on the gum - not so much because it made a mess for the guy, who cared about that? ...but rather because her jaw was absolutely exhausted now, and he still hadn't cum.

Standing back up straight, Gum leaned against Yuta, squeezing his left shoulder between her dress-clad tits again, to examine his handiwork.

"Not bad for an amateur," Gum said, nodding at the appearance of the spray paint lines forming the picture of a big pair of breasts on the wall, complete with nipples and areolae. "Uhhh..." Yuta was blushing furiously. "I was originally going to write my name but, well, I guess I had something else on my mind..."

"Hey, no problem. I like art that gets a little bit lewd and crude." Gum said. "Of course, I'm still going to put you to shame and tag up something that's going to make yours look like crap an 8 year old painted, in comparison. But even though your cash is as good as gone you might as well do your best to distract me. Since yours is really high up on the wall while you were spraying over my shoulders..."

Gum ran her hands down her incredible curves and waggled her hips from side to side as she turned around, enticingly. She then bent over and put her leg wide apart, flashing Yuta quite intentionally as the hem of her white minidress rode over the top of her asscheeks.

"...I'll bend over nice and low so I can do mine underneath." With one hand she took her can of green paint and began shaking it up, while the other one went into a small personal pouch on her bike leaning against the wall nearby.

Yuta watched what she was doing curiously, hearing a soft crinkling sound. Gum wasn't even looking at him, still shaking up the can with her right hand while she thrust her left hand back behind her towards Yuta. His eyes bugged out and he gave a little gasp when he saw what it was. The white-gloved hand opened to present Yuta with an unopened condom wrapper.

"I know what you're thinking, dude, so go ahead and put that on." Gum said calmly. "A good challenge should be risky but wearing a helmet is just common sense, right? Remember, you can use your hands to 'distract' me but you can't push me into the wall or pull me away from it and you can't interfere with my arms. Same as before. 10 minutes."

Yuta had all but forgotten Mew. The big, waggling ass popping out from underneath that minidress and the green panties hugging the contours of the slit underneath were giving him some serious tunnel vision. Although he thought back to a couple of days ago and how he kind of messed up his chances to meet with Mew by going too far with Piranha, how could he possibly pass up a chance like this, he wondered? Well, he thought to himself, he'd learned his lesson... this time the girl had been prepared too and gave him a condom, so there was no need to hold back. He wrapped one of his hands around her inner thigh, running his hand over her eponymous tattoo, before sliding his fingers up to rub against her panties. He hooked an index finger around them and tugged them lower.

A high pitched hissing filled the air as Gum casually began painting. Yuta didn't even spare a look over his shoulder before eagerly tearing the condom wrapper open and slamming the rubber down over his dick in one sharp motion. "I'm so glad you knocked me down earlier, Miss Gum..." he said sweetly as he lined his hips up with her enticingly waggling ass...