Will and Chloe

So this is my first ever story. Huge thanks to shadysweet for editing it. They did a great job and any mistakes still left in the story were likely made by me after their final edit. I may write a part 2 if people like this one enough.

Thanks for reading.

Will was almost late. It was nearly 7 pm and they had decided to meet half an hour before their 7:30 movie so they could go for a walk at the park and introduce themselves properly. He'd lost track of time between grooming himself in the shower (he'd been more optimistic at the time) and trying to find a pair of jeans that fit better than the ones he was currently wearing. Though he hadn't been overweight, he'd wanted to tone up and the last several months of daily gym sessions had trimmed his waistline to the point of him having to constantly pull his pants up, he'd put off buying pants that fit better and now he regretted it.

So there he was, driving in his car, hair still damp from his shower, about to meet a beautiful girl in the park across the theater for a short walk just before the movie, and his pants didn't fit. Not a good start. He knew he'd be pulling them up all night and he was kicking himself for not preparing an outfit beforehand. He'd look like an idiot that couldn't dress.

Will sighed. "Oh, well. Hopefully she won't notice."

He decided to park in the small, empty lot behind the theater since it was closer and he didn't want to risk making Chloe wait any longer than she probably already had. He sent her a quick text letting her know where he parked and that he'd meet her at the park behind the theater.

"Sounds good, I'll see you soon! So excited to meet you!," was her reply.

He smiled as he got out of his car and power walked to the park across the street, occasionally pulling up his pants as he went. Aside from the pants fiasco, he was nervous to meet Chloe. She was gorgeous in her pictures. About 5'4", red hair, lightly tanned skin with a light dusting of freckles across her nose and cheeks, and the most beautiful dark green eyes he had ever seen. Will knew he was no slouch in the looks department, he just never thought he'd be able to pull someone like her with his awkward online chatting and goofy sense of humor.

He arrived at the bench and browsed his phone for about five minutes before he heard, "Hi! You must be Will."

Will nearly started as he looked up, he hadn't heard her approaching.

"Yeah! Hi! And you're Chloe." Will said awkwardly, inwardly kicking himself for being caught unaware. Chloe smiled big, flashing straight white teeth, and nodded. Will quickly got up and stepped forward, extending his hand for a shake, but whether on purpose or misreading the gesture, Chloe stepped under his arm and gave him a tight side hug, her arm wrapping around his waist, and her breast pressing against his side. Will couldn't help but notice how well she fit there. He was several inches taller than her and his hand seemed to naturally settle on her hip, she didn't seem to mind at all.

The hug went on for a moment longer than he thought she'd be comfortable with on a first meeting. As they stepped apart, Will glanced down and finally got a good look at her.

Hell's bells! Will thought. This girl is crazy hot! Why did she want to meet with me?

Will had never felt intimidated by a girl's looks before but suddenly he felt apprehension upon seeing her in person. The first thing he noticed was the black choker around her slender neck. It was about half an inch wide, and made of either velvet or leather, he couldn't tell at first glance. It had a small metal heart pin on the front. Despite the cool weather, Chloe was wearing a mini dress made from a thin, soft material that hugged the pleasing curves of her hips. She clearly wasn't wearing a bra as he could see the tips of her large, full breasts, which the dress hugged and cupped enticingly. Her nipples had hardened in the cold. This made her flat and toned belly even more apparent and Will's heart started to thump in his chest. He'd always been a sucker for a girl with a generous chest and flat stomach. Continuing down, the dress stopped about half way down her toned thighs and Will couldn't help but stare at those longer than was polite, he was sure.

Jesus, he thought, I don't think this night is going to end the way I want it to. Which is to say with a promise of a second date at the least and if he was feeling especially hopeful, a kiss. Will didn't consider himself to be a pessimist, but a realist, and he thought Chloe might realize that she could do better than him by the end of the night.

"Will?"

Will's eyes shot up to hers, "Huh? I'm sorry. I didn't catch that..."

Chloe gave him a tight-lipped smile that made her full lips curve upward pleasantly as if to say, 'Well, I did catch you!.' Her eyes still glittering with mirth, she said, "Did you still want to go for that walk?"

"Oh, yeah! Let's do it." And so they walked about the park (Will occasionally pulling up his pants, which she didn't seem to notice or if she had, politely didn't mention it) talking of their hobbies and getting to know one another. Though they had been chatting online for about a week, he hadn't learned as much as he'd thought about her. She spoke of being a gymnast, her yoga hobby, and the one year she spent as a pole vaulter in her last year of high school. That surprised him, he had never known anyone that did pole vaulting. She didn't continue it into college, claiming she hadn't been all that great at it, though she had a lot of fun doing it. Turns out they went to the same community college at the same time, though he'd never seen her. He would have remembered. She was twenty three, the same age as him, and worked as a nurse. Will was excited to learn she was really funny and very clever. Several times he'd thrown his head back to laugh at a quip or joke she'd walked him into.

In turn, Will spoke of being very into 3D printing and programming. He loved to read, mostly fantasy, sci-fi, and horror, which she also loved. He mentioned he'd been hitting the gym pretty hard lately and discovered they attended the same gym franchise a couple of miles apart. Chloe said she went to the gym five days a week.

That explains the incredible body, he mused.

Will told her of his OneWheel that he loved to ride just before sunset when there was a cool breeze and she playfully demanded to be taught to ride it sometime soon. She'd done the same thing when he said he had a couple of 3D printers. He told her how he liked to build computers and that he'd built his own.

"Oh! Does yours have all the colorful lights and stuff?" She asked excitedly.

"Well, yeah. But I usually just keep them in a warm yellow/orange color, but yeah, I can change the colors to whatever I want. It's pretty cool."

"That's so cool! I'm pretty good with computers, but I don't know much about the inner workings of them or how to build them. You'll have to show me yours sometime."

Will promised he would.

She also promised to give him tips on how to get his white low top Converse sparkling again after he commented on how clean her own worn, but clearly well taken care of pair had been.

And that was another thing. Something about a girl in a dress, whether that was a sundress, mini dress, skirt, whatever, and a pair of low top Converse (preferably white) just did something to him. He figured it was the balance between sexy and casual that just did it for him.

After promising to let her borrow his favorite horror novel (Will realized he was racking up a lot of promises to this girl on such a short walk), he started to notice a trend of her playfully demanding he show her his 'toys' as she called them. This made him hopeful that things were going well enough for a second date at least. He'd also noticed that she'd taken every chance to touch him. Whether that was poking him in the side, touching his arm, or brushing lint off his shirt, his heart hadn't seemed to slow down since that first glimpse of her after the hug.

It was around this time Will noticed she had some sort of rubber band or hair tie around her wrist she would occasionally snap loudly. He'd been hearing it this whole time without realizing what it was.

"What's that?" Will asked, pointing to the band.

"Oh," Chloe raised her wrist and Will saw it was a thin, dark green hair tie. "I tend to fidget a bit when I'm nervous-" She cut off as she seemed to realize what she said.

Will chuckled, "Well I doubt the movie will be that scary so I'm sure you have no reason to be nervous," Will joked while poking her in the side for once, knowing full well that's not why she was nervous. It calmed him and made him feel better to think she was nervous too. He had the sudden, ridiculous urge to look at her chest to see if he could see her heart beating as hard as his had been, but stopped himself just in time.

"Hey!" She laughed at the poke, "Well, I heard it was supposed to be pretty scary so you might have to hold me if I get too scared. I love me a good horror movie, but who knows why since I get so damn scared most of the time."

Will said he would do his duty and lend her a shoulder to hide behind if she needed it. He didn't miss the sparkle in her eye as she snapped the hair tie again. A little bit more loudly than before.

Once they made their loop around the park and headed back toward the theater, he noticed a white car parked beside his own car. It was starting to get dark and he realized he hadn't parked near the only flickering light in that tiny parking lot. He'd parked right next to the building in a patch of darkness; this reminded him he needed to make sure to walk Chloe to her car since the movie would probably end close to, if not after 10 pm and it would be dark.

They made their way around the building and up to the ticket booth and once Will bought the tickets Chloe said she'd get the drinks (neither wanted snacks). He tried to tell her that there was no need and that he'd pay for them too, but she wouldn't hear it. She insisted she pay for the drinks at least. She said she liked things to be fair on dates and didn't want him to feel like he was being taken advantage of. There seemed to be a gleam in her eye as she said this. Will didn't know what to think of it, but it set his heart to thumping all over again after it had just calmed. He realized he'd become at ease around her during the walk and that comment about him being taken advantage of made his heart race all over again.

They stepped into line and Will admired her profile as she looked at the menus. He thought she looked so beautiful with her head tilted back slightly, her plump bottom lip bit between her teeth, the bright, colorful lights from the monitors playing across her face and shining in her wavy red hair. When she stepped up to the counter he took this opportunity to step back and admire her from behind.

Wow, he thought, and an incredible ass too. He also noticed the two guys behind the counter surreptitiously checking her out when they thought she wasn't looking, though he was pretty sure she noticed them noticing. She didn't look irritated or pleased either way and Will couldn't imagine being that good-looking and having to deal with that all the time in public. He suddenly felt really guilty for ogling her at the park.

"Why are you standing like that?"

"I'm sorry?" Chloe had caught him off guard again.

"Why are you standing like that?" she gestured to his legs with one of the cups in her hand.

He hadn't realized it, but he had kind of hiked up his pants and stood with his legs parted a bit more than natural with his hands in his pockets.

Will's face reddened. "Well, remember how I said I'd been going to the gym a lot lately? I've lost just enough weight that none of my pants fit very well anymore. And none of them were tight to begin with. I just kept putting off going shopping because I never seem satisfied with what I find. I always feel awkward looking for clothes and trying them on so I dread doing it. So here I am, pants falling down all night because I couldn't find the belt I haven't needed in years. The only other things I had that were clean were some old shorts and my gray sweatpants."

Chloe laughed, "You should have worn those sweatpants." She winked at him as she walked past, passing a cup to him at the same time.

Whoa oh! Will thought. He'd read online that girls liked to see guys in gray sweatpants. Apparently it was easy to catch a glimpse of a guy's dick in those.

"I'll wear those on our next date if I don't have any pants that fit by then." He said offhandedly, hoping he hadn't overstepped himself.

"Deal!" Chloe announced.

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They sat near the top row inside the auditorium and picked the center. The room was nearly empty since it was a Wednesday night and the movie would be ending late. There were only two other couples seated far from them. Will picked a seat and she sat down to his right, crossing her legs as she did so. Will couldn't help but notice her dress fell up her thighs a bit. Whatever lotion she used made her thighs look so incredibly soft and enticing in the light from the movie screen in the dim room. She had great skin.

Will looked up from her legs only to see that her eyes were already on him. She had a small smile on her face that still reached her eyes.

"You excited for this movie? I've been waiting for it for a long time, I wasn't sure I'd have anyone to see it with," Will asked, trying to deflect before she had a chance to call him out.

"Heck yeah! I've been waiting a while too. None of my girl friends are into horror movies so I was resigned to seeing it alone or waiting for the blu-ray."

"Let's hope it's good then," Will said, and turned to the starting movie.

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The movie was scary. Well, Will was pretty sure it was scary. It was hard to focus on the movie because since the first jump scare, Chloe had shifted to her side, leaned over to him, grabbed his hand which had been resting on his lap, and buried her face in his shoulder. She had grabbed his left hand, awkwardly enough. It had been resting right under his right hand right in the middle of his lap, but when the jump scare happened he'd moved his right hand which was the hand he was sure she intended to grab. So with her reaching awkwardly over his right arm, he took a chance at a more comfortable resting place and for his right hand and placed it on her right thigh, which was made easier by the fact she was practically sitting on her left hip. She didn't seem to mind, in fact, she snuggled a bit closer.

He had initially placed his hand on the part of her thigh covered by her dress, but that had continued to move upward with her squirming. So instead of getting too presumptuous and moving his hand up with it, he kept it in place, but now on her bare skin. It felt electrifying to him. So much so that he was starting to get hard in his pants and worse, he was sure she had noticed as she had started to ever so subtly move her hand back and forth across the crotch of his pants.

This went on for the remainder of the movie. His erection occasionally subsided whenever the movie got intense enough that neither of them could help but pay more attention and then right back up again as soon as there was a lull in the action and Chloe started rubbing him again. He was going to have one hell of a set of blue balls tonight, he knew.

Once the movie was over they waited for everyone else to leave, stood (Will pulling his pants up and trying to stealthily adjust himself) and began to walk down the steps. Chloe didn't pull her dress down, which had ridden up to just below her round ass, until they reached the bottom. He enjoyed the view of the bounce and jiggle of her ass and thighs until she did.

They chatted about the movie on their way out. Neither of them could remember any details and both of them tried to hide that fact from the other. It was cold enough outside that Will couldn't help but to notice her nipples were hard beneath her dress. He cursed himself for not bringing a jacket he could give her.

Will didn't want the night to end and it seemed like Chloe didn't want it to either, though she was snapping her band more often than ever now.

"Can I walk you to your car?" Will asked.

"Yes, please. I don't think there's going to be any lighting where I parked."

"Where did you park?"

"We passed it on the way in. Around the back of the theater." Chloe said.

"That's where I parked too. I hadn't realized that was your car." Said Will.

"Oh? I hadn't realized either..." Chloe said, but trailed off.

Will thought that was weird. What were the odds that she would park behind the theater too? And right next to him? The only reason he'd parked back there was because that was the direction he'd come from. He knew from their talks that she lived on the other side of the theater. Had he mentioned in their chats online what area he lived in? He thought maybe he had. Why had she made it a point to park right next to him?

As they made their way to their cars he noticed that no one else was parked in the small lot and the only working light was on the other side of the lot, flickering occasionally. It was fairly dark and quiet.

His thoughts were derailed as she spoke.

"Will, I had a really great time tonight. You're very sweet. I can tell you're smart too and you had me laughing all night. And I think you're very handsome" Chloe said demurely.

They were standing between their cars. She was leaning with her butt against her driver door, looking up at him through her lashes with big, innocent eyes, chest rising and falling more than before. She had one shoe propped up on it's toe in that cute way girls do sometimes.

"So did I," Will said. "You are so fun to talk to and I think you made me laugh even more! Not to mention you are absolutely gorgeous, Chloe. I was afraid I'd blow it all night!" Will laughed.

"Not yet...Kiss me?"

Will should have known. He should have known that this newly demure girl didn't really match so much with what he'd seen throughout the night. The sudden ceasing of the band snapping should have warned him.

Will took a small step forward, placed his hands on her hips, leaned down, and kissed her. She met his lips eagerly and kissed him with passion.

After several breathless moments of making out in the dark she said, "I want to taste it, Will."

Will, being a bit light headed, didn't understand. He hadn't realized it until now, but with that small step forward his legs were closer together and his pants had been sagging. This seemed to be exactly what Chloe was waiting for.

She reached in his boxers which were now visible, but she didn't grab his hardening cock, she instead grabbed his balls.

Will simultaneously felt and heard a loud snapping sound around the base of his balls and he flinched.

"What the hell, Chloe!?" He said in a loud whisper, breathing heavily, apprehension mounting.

"Shh, shh, Will! Careful! Careful. I've got your balls, Will. Don't move or I'll squeeze." She proved this by squeezing and tugging his balls down gently even though Will hadn't moved.

This caused his fingers to dig into Chloe's hips. She hummed in pleasure at that.

"What are you doing, Chloe?!" He hissed. His balls ached a bit, but she'd been mostly gentle so far. And he noticed he'd only gotten harder since she'd grabbed him.

"I told you, Will. I really like you and I want a taste and this is how I want to do it. I'm going to suck it out of you. I'm going to milk your cock and drain your balls into my mouth, Will. I promise you'll enjoy it if you don't fight me. If you do, just remember I've got your balls in the palm of my hand and I'll squeeze them until you do whatever I want, understand?" Chloe asked breathlessly. Had begun to stroke his cock while alternating between gentle and rougher squeezes of Will's balls.