Try and find Emily downtown

With just a little guilt, Matt decides he’s going to try and see Emily again.

Lucy will expect him to study with Abigail so, as far as she’ll know, he will be. It’s not like those two even talk, anyway. If he decides to pretend he’s at home Lucy will expect him to message her but if he’s supposedly studying she’ll leave him alone.

He resolves to put any doubts out of his mind. In all honestly he think he’s just going to hang out at a food truck festival and then go home. What would he and Emily even talk about? Why is he even going? He knows it’s because the thrill of just the possibility of cheating felt too good; too right. He shoots Lucy a quick message that he’ll be studying tonight. His dick throbbed in his jeans as he allowed the fantasy of actually cheating on Lucy dance through his mind.

The bell snapped Matt back to the present. He only had a few minutes to see Lucy so he half-jogged through the crowds to her locker.

“Hey, cutie,” he whispered in Lucy’s ear from behind when he finally arrived.

She turned and planted a long kiss on his lips. It was surprisingly hot and it almost made Matt change his mind about tonight. Almost.

“Hey, baby,” she said when she pulled away, “you excited for you little study date.”

“Don’t call it that,” Matt mock groaned.

“At least she has a super cool house,” Lucy said, shutting her locker.

Abigail’s family was absolutely loaded and her house was more of a castle than a home. Matt was sorta disappointed he was going to miss out on it.

“Okay, gotta run. Let me know how it went!” Lucy smiled and gave Matt one last kiss, fondling his package discretely.

He told her he’d message her and then she was gone, leaving him alone in the twisting tides of students trying to get home.

—

Matt found the festival on the internet and he had a couple hours to kill before he got a taxi to the boardwalk. It looked like a sweet deal in the pictures. Tons of people and tons of trucks and sometimes live music. The weather, however, wasn’t really cooperating. The wind had died down but it was still cold and gray with a touch of rain. Oh well, he had committed to this plan and he would see it through.

Briefly, Matt considered helping himself off while he waited to head downtown. In the end he decided against just in case he made some progress tonight. He didn’t expect to, of course. Emily barely knew him and he was still in high school. But, a little part of him thought he could pull it off, and that was enough. If he struck out he could always have his release at home afterward. So he distracted himself with chores and video games until it was late enough to call a taxi.

The ride to the festival was surprisingly nerve-wracking. He fidgeted in the backseat constantly. He thought about Lucy who sincerely thought he was at Abigail’s house doing homework. But he also thought about Emily. And for every block closer he got to downtown he thought more about Emily and less about his girlfriend. He daydreamed about Emily’s plump, full body and her big, soft breasts...

The taxi pulled up to a boardwalk entrance with a jolt. Matt paid his fare and hoped it would serve as a good investment. He thanked the driver and stepped into the cold. The wind whipped him in the face, a cold breeze from the ocean, right as the taxi pulled away.

“Great,” He said sarcastically.

Every step toward the apparent festival was more miserable. He cursed himself for thinking this was a good idea. There’s no way Emily would be as dumb as he—

Matt froze. The trucks were just ahead, maybe a quarter of the normal offering with a very small crowd huddled around them. One of them stuck out to Matt like a sore thumb. Emily was standing by one of the closet trucks with her arms crossed in front of her, visibly shivering even from this distance. Matt could only roll his eyes at the odds stacked against him. He checked his phone, finding no notification from Lucy, and then shuffled toward the nurse.

Emily saw Matt approach before he could say anything. He tried to appear casual but he wasn’t fooling anyone.

“Matt, is it?” she said.

“Yeah, nice to see you again.”

Emily looked stunning even in the poor weather. Her blonde hair cascaded from underneath her coat hood. Her coat was brown and much more form fitting than the scrubs Matt had seen earlier. She had shapely jeans on, too, that showed off her very voluptuous figure and her beautifully wide hips. She was bundled up but, damn, Matt was into it.

“Yes, fancy seeing you here,” Emily said with an accusatory tone.

“I heard about this from a very reliable source,” Matt offered.

“Oh yeah? Who was that?”

“Uh... Okay it was you.”

Emily nodded, her facial expression betraying she was not surprised at all.

“You must have knocked your head pretty good, hm?”

Matt looked at the ground sheepishly. “Okay, this is weird.”

“A little,” Emily said, “and maybe a little creepy.”

Matt put his hands up, “In my defense I figured it would be a lot busier and I wouldn’t even see you.”

“That’s normally true,” Emily sighed, “but the weather didn’t want to play nice tonight.”

“I’m surprised you came at all,” Matt said.

“I could say the same for you,” Emily countered.

“I may have been motivated by a really beautiful nurse,” Matt quipped immediately.

Emily considered. Matt met her gaze and noticed her eyes were a deep, brilliant blue. He was losing reservations about this silly plot and gaining confidence every second she didn’t tell him off.

“Okay, well, here I am. You got what you want, right?”

Technically, she was right. But Matt wasn’t satisfied.

“Perhaps,” he said casually, “but I think you could get something you want.”

She waited expectantly.

“I’ll buy you dinner?” Matt offered.

—

The basket of egg rolls steamed in Emily’s hand. Standing in line hadn’t been too awkward. The fairly empty court made it worse, however, and Matt felt out of place next to Emily. The weather could work to his advantage but getting Emily to want to snuggle up next to him would be a challenge. Although, it was all a challenge.

“Those look divine,” Matt commented as he waited for the rest of their food.

“Try one,” she encouraged.

Emily was in a little bit of a pickle. She never came to this festival for dates. It was a fun event to look forward to with good food and a pleasant atmosphere, an excuse to get out of the apartment and get some fresh air. She never talked to anyone unless she was ordering food. Now, however, a student had basically followed her specifically to... well, seduce her, she imagined.

She watched Matt take a bite of egg roll and let out a moan of satisfaction.

He let out a moan, “Wow, holy... holy shit!”

A little bit of the egg roll hung off the corner of Matt’s mouth and Emily almost reached up to wipe it away. She stopped herself but the instinct surprised her, why would that interest her? She chalked it up to being a tiny bit starved for romance. It wasn’t that Emily was ugly or anything, she had lots of guys in her DMs who found her at random, but her in-person options had not been great recently. She could try online dating, but that just wasn’t for her. It didn’t feel spontaneous.

The moment that thought entered her mind the logical progression was right there, waiting.

It was pretty spontaneous of Matt to show up here.

“That’s incredible,” Matt said, oblivious to her inner conflict.

So, maybe this teenager wasn’t her first choice to surprise her with some companionship. But he was already here. She might as well make the best of it. Emily resolved to enjoy it for a little while, at least, and then they would part ways and everything would be fine. Nothing weird, just a pleasant, if chilly, evening.

“I told you,” Emily said, taking her own bite.

Matt found himself pausing as Emily pulled the half-eaten egg roll from her mouth. He had to shake away the image of her putting something of his in her mouth. The amount of times he was finding himself in this position with her was a surprise considering how long he’d even known her.

It didn’t matter how good the food was, the cold was starting to win even against the hardcore crowd on the boardwalk. Trucks started to shutter and the two accidental dates knew their time was coming to a close. Emily was standing closer and closer to Matt as the wind howled until she might as well have been cuddled right beside him. It wasn’t unpleasant.

Emily found herself having a nice time. Conversation was at a minimum because of the weather but Matt was polite and didn’t fit the creepy vibe she had expected. Did it help that he was tall? Probably.

“On a better day this would make a great date,” Matt said absent mindedly.

“Yeah, this is a pretty shit date,” Emily said playfully.

Matt blushed, “Okay, that isn’t—“

A powerful gust from the sea silenced him and sent them both nearly tumbling backward.

“That means it’s time to go!” Emily found herself shouting, “and I can’t feel my toes...”

Matt nodded in agreement and pulled out his phone to call a taxi home.

“How’d you get here?” Emily asked as they shuffled toward some cover.

“Taxi!”

Emily chuckled, “You know there’s a parking garage, like, right here?” She pointed roughly the direction they were going.

When Matt shook his head to tugged his arm, “I’ll take you home. Since you bought me dinner we’ll be square.”

—

They practically dove into Emily’s little sedan once they found it. She started it up and cranked the heat.

“Nice ride,” Matt said while he shivered.

Emily smiled and rubbed her hands together. It was stupid cold but she couldn’t deny that things were warming between her and the teenager in her passenger seat. Her opinion of him was becoming more and more positive the longer she was around him and she was sort of sad she had to take him home. What worried her, though, was that she had been forced to banish small little fantasies from her imagination. Matt has inadvertently referred to their meeting as a date and it made her heart skip. Once she caught him staring and she nearly kissed him.

Emily’s phone buzzed. She tore it from her pocket with some effort to read the banner.

“Well, I got called off for tomorrow,” she announced, looking at Matt.

“So... you don’t work for the school, then?”

Emily shook her head.

The next thing she said surprised her just as much as it would surprise Matt.

“I think I need to stop at my apartment first, if that’s okay.”

—

Emily trudged up the stairs to her apartment with Matt in tow. He hadn’t asked what she needed, thankfully, and she was struggling to think of a reason to be up here. Matt, however, was not about to open his mouth and ruin his good fortune. He didn’t expect to get this far, although truthfully he didn’t even know what he was trying to get in the first place.

The door swung open and Matt followed Emily in.

“Guess my roommate isn’t here,” she said.

The place was cozy and eclectically decorated. It was a mish mash of styles, one trying to make a cottage and the other trying to be a 40 year old wine aunt. Matt couldn’t tell which style was Emily.

“Nice place,” he said.

Now that they were inside an awkward silence descended. Emily still had not come up with the reason to be up here, other than the chemistry between her and Matt that had tickled the edge of the conversation since she saw him. Matt didn’t know what to do either considering this was the first time a woman had brought him into her house like this. He wasn’t the most confident guy anyway and he wasn’t about to make any sort of move on a woman half a decade, or more, his senior.

At they each fumbled in the silence Matt thought of Lucy. This entire evening had been a betrayal of her trust in him. It wasn’t right. He should go, but he couldn’t. No, that wasn’t true. He wouldn’t. He replayed the memory of Emily, in full nurse mode, checking his head and the generous cleavage he had seen earlier that day. Emily shucked her hood off and ran her hands through her long blonde hair. It fell down across her chest and may have been able to cover them completely if her breasts weren’t so massive. That was the moment where Matt decided he wouldn’t let Lucy keep him from anything that could happen tonight in this woman’s apartment.

Emily took off her coat, slowly peeling it from her arms and tossing it on the kitchen counter. This is how she would gauge Matt’s interest and find out if he was a silly, oblivious teenager or a man who knew what he wanted.

Beneath her coat was a beige colored dress that wasn’t quite long enough to be seen underneath the coat. The dress was astonishingly revealing because it was designed to be paired with the cream shit underneath it that covered most of her chest. Her breasts, of course, defied modesty and the entire top half of each was visible, pushed up and together by her sturdy bra that just poked out from the middle of the shirt. Beneath her breasts an elaborate black belt kept her dress tight to her voluptuous figure and only accentuated how far out from her body her soft tits bulged.

Matt stared. How could he not? Her cleavage called to him beneath her pretty face, as if asking him to bury his face between the soft pillows of flesh. His jeans tented at the sight and his mind went blank.

This was the reaction Emily had expected. She stood under the unwavering attention, hands on her hips, and considered her options. No, she wasn’t. No more considering. No more thinking. Emily only wanted action.

Emily stepped forward and grabbed at his hands which hung limp at his side. She pulled down on them and leaned up, without giving him a moment to consider, and kissed him.

Matt was still frozen in place by her cleavage when Emily made her move. Her breasts bounced gently with her handful of steps toward him, hypnotizing him so that he wasn’t ready for her lips. He recovered smoothly enough, settling his face against Emily’s.

This would be the last time Matt thought about Lucy tonight and it was only to think that he could already tell Emily was the better kisser. But then her face and her name faded in favor of the thick blonde against his lips. Matt eagerly returned the kiss and played a significant role in pushing it deeper and longer. He let go of her hands and wrapped her arms around her waist, coming to terms with her size. Her breasts bulged between them.

Emily dragged Matt, refusing to break the kiss, toward the closest couch. Using feel alone she sat both of them on it while her tongue pushed into his mouth. He had his close arm around her and the other came across to grope at her chest. Her massive breast filled his hand, plump and soft, and he couldn’t help but moan into their passionate kiss. Matt sunk into it with heat that surprised even him. He fondled Emily’s tit with growing aggressiveness and then she laid her hand directly on his bulge.

She smiled, mouth open and sucking Matt’s tongue, when her fingers curled around the heaving bulge between his legs. With this encouragement he started slipping her dress from her shoulders. She pulled away and giggled, fumbling with the belt underneath her tits. Matt was hardly breathing. As the belt fell away her tits didn’t move, held in place by her bra. They attacked each other again and Matt was able to pull her dress off of her. She let his hand explore her chest and torso, half expecting him to be less than pleased about the amount pudge on her stomach.

Matt’s hand squeezed around her belly, the nearly sheer shirt barely containing her body. It drove him wild. Matt has never been attracted to large women. He stayed away even from porn of women who weren’t slender and petite. Had Emily's scrubs been more clear about her shape he might not have even been interested. Her tits had hypnotized him.

Something must be waking in Matt because, holy shit, he thought Emily was fucking hot right now.

She ripped his shirt off of him and again their lips clashed. The small living room was filled with the wet sounds of the sloppy making out. He started tugging at her shirt, trying to remove it but so focused on the kiss he couldn’t get it done. She giggled and tossed it up over her head for him. He didn’t get time to appreciate the view before she was at him again. They moaned together as the heat built steadily to a raging fire.

Emily couldn’t wait any longer. She pulled away from Matt’s lips, grinning at his whimpering, and settled on the ground on he knees below him.

“Let’s see what you have in there...” she said softly, biting her lip while she began pulling his pants down.

His erection snapped to life, already raging. Matt thought it looked a little larger than normal, but he knew he wasn’t done yet. She was already pleased with it, spreading his legs and planting soft kisses on his thighs. She was fondling his balls, a sensation he didn’t realize he would enjoy so much, when the growth started.

Matt’s cock once again began to surge with new life, extending steadily into the air. Emily was so so focused below it that she didn’t notice until the shadow fell across her face. By then it was throbbing with strength, thick and long, and much larger than anything Emily knew could exist.

“What... what the fuck...” she blurted.

Emily had a similar reaction to Lucy. It was monstrous, too monstrous, and she almost wanted to leave. Lucy remained because of her connection to Matt, but Emily remained because the thought of being fucked by this beast absolutely drove her mad.

“I was going to blow you but... uh...” Emily stammered.

“No, that’s fine,” Matt started.

Emily reached back and removed her bra, her giant breasts falling down her torso and swinging gently. Matt saw and squirmed with the heat that was taking over his mind.

Without another word Emily wrapped her breasts around the base of Matt’s cock. They ballooned against his hips and around his vibrating rod, her tongue working him slowly as the rest of it extended past her head. Matt’s hips bucked softly through her big tits and against her lips.

Emily loved foreplay. She loved teasing her partner with her breasts and her mouth until they can’t hold another second and pound her into submission. Tonight, for the first time, she didn’t want to wait. She wanted him now, anywhere. His exaggerated balls quivered below his massive dick and Emily needed them to unload all over her.

Matt’s jaw hung limp as he took in the sight. The blonde had her lips against his shaft, giant tits enveloping it, teasing the base of the long length. Emily’s eyes were pleading him to take her and use her. He didn’t recognize the extreme lust and was quite happy to sit here and let her work her magic.

Breathless, Emily stood, beckoning him to her bedroom. He followed, his rod poking at he wide ass. She shimmied her jeans off as they walked and now Matt could see her entire body. Nothing was hidden. She was thick, chunky, and he couldn’t get enough.

As they passed through the door Matt pulled the blonde around and kissed her, finally taking his place as her man for the night. She melted into the kiss, holding his cheek, both of them stumbling toward her bed. The collapsed on it and they crawled further onto it, moaning into each other’s lips. Matt’s dick raged between their bodies and Emily fondled the bulging bell-shaped tip. Matt kissed her neck and her collarbone before firmly taking her naked nipple into his mouth. He suckled eagerly at it, relishing her moans, while his hand groped at the other. Their hips were grinding instinctively, ready to have at each other.

“Oh god, get in me!” Emily groaned.

He sat up, nestled between her thick legs, with hi massive manhood twitching from his hips. He pushed it toward her pussy, the glistening mound beckoning him inside. Her lips were naturally open, a wide pink entrance that looked soft and was already drenched. It was bald but with the tiniest hint of regrowth. Matt licked his lips, prodding the soft lips with his cock. Emily let out a moan and the wet flesh clenched around the this rod, pulling it inside.

Matt’s cock sunk easily into Emily, the walls squeezing him tight. She gasped as her pussy stretched to accommodate the beastly girth of Matt’s manhood. He couldn’t believe how easily he slid into her even when she was so unbelievably tight.

“Oh fuck, oh fuck, oh fuck...” Emily panted, arm crossed underneath her big breasts.

Matt sunk into Emily until a full third of his prodigious shaft throbbed inside her tight pussy. He wanted go further, but Emily resisted, the girth too much so soon.

“Holy fuck, you’re so fucking big,” Emily grunted.

Emily had a potty mouth. She tried to keep that under wraps most of the time but after seeing and feeling Matt’s raging cock she couldn’t hold back.

Her arms splayed as her body quivered around him, her fists grabbing at her sheets as Matt began to fuck her with almost an agonizingly slow pace. Matt made sure she felt every inch she could take. He grunted as her walls pulsed around his shaft, the thick cockhead struggling to push through her tightening passage. The bed beneath Emily’s ass was already a dark puddle from her fluids gushing out with heat.

Matt held the blonde’s legs apart, slowly increasing the pace into her steaming hole. Her breasts had fallen to her sides, shaking as he ramped up the speed of his thrusts. He let her legs go and grabbed her big tits and used them as handles to increase the speed even more. Soon he was fucking her fast enough to split into her even deeper, desperate to get as much of his giant dick inside.

Emily usually took a long time to orgasm. She needed to be touched in specific ways and specific times. It took her partner’s a long time to learn what her body needed. Matt, however, was not beholden to these requirements. Her body changed to need him, and only him. She came violently, back arching with release. A wet ripping sound exploded from her stuffed cunt as she squirted a heavy steam of clear fluid onto Matt’s hips. Emily couldn’t make a sound, desperate to tell her lover how incredible he felt but unable to form a coherent thought in the crashing heat of her insane orgasm.

Emily had barely recovered when aftershocks shot through her body as Matt plowed her faster and faster. He groped her breasts, tugging in her hard nipples and grunting as he railed her. His balls quivered, almost ready to unleash their payload.

“Oh fuck, oh... shit! Fuck!” Emily grunted, “You’re so... so fucking big!”

Her voice cracked as she came a second time, unleashing another hot stream of fluid all over her teenage lover.

“Oh, Emily, Emily...” Matt suddenly muttered as he was edging closer to his own orgasm.

“My tits! On my tits! Please!” Emily grunted, still rocking back and forth with the relentless pace of his hips.

Matt fell backward just in time, grabbing his hard meat and pumping it once before his taught flesh throbbed with release. Emily grabbed her breasts and shoved them together as her lover came, a huge shower of thick, white semen crashing against her fat titties. Her jaw dropped as he unloaded the biggest load she’d ever seen directly into her heaving chest and neck. Matt stood, tense and grunting, until he was finally finished depositing his babymilk onto the chubby blonde’s soft tits.

Emily’s legs quivered, thighs glistening with her discharge, while her pussy flexed with the last of her orgasmic aftershocks.

“Holy fuck, Matt...” the blonde moaned.

Matt caught his breath, eyes locked on the cum-covered woman he had just fucked. She licked his cum from her wet breasts, moaning gently.

This was the moment when Lucy’s face appeared in Matt’s mind and he remembered the lies he had told to his girlfriend.

“Oh shit, what have I done...” he whispered, rubbing his face.

Emily, oblivious to his conflict, moaned in response. “Fucked me senseless, that’s what you did.”

Matt looked at the blonde and their eyes met.

“Come kiss me, you stud,” she said, arms outstretched, tits falling beside her.