First Date Risks & Rewards

Kyle was bored. It was 9pm, on a work night, in a small rural city that closed up shop 30 minutes ago. This is how he found his evenings. Pretty much alone, watching TV or porn or catching up on social media. Bored.

He thought life was going to get interesting after graduation. He had taken a job across the country, and ended up in a sleepy little New England town. He loved his job, loved his new apartment - but he missed his friends. He found it very hard to make new friends - especially now that the weather was colder. He spent a lot of time at work, and there just wasn't a lot of night spots in the community. So he had turned to a few online dating platforms. He wasn't expecting much, there just weren't many people in the area near his age.

So he was surprised when his email refreshed and he had a connect request.

It was late, but he figured he'd go login and find out what was sent. A few seconds later and he was in. She seemed nice. Funny profile, nice pictures, close by. She had a nice smile, dark hair and blue eyes. She had a sense of humor, and listed her age as 26. She did say she was very forward and very direct. He didn't think that was a problem.

He opened her message and it was fairly direct. It started off by welcoming him to the region and saying that she liked his profile and would love to meet. He was pretty sure that this was rare in the online dating world. And he was concerned she might be a bot. He had his hopes up but he was guarded. So he sent a reply back, asking if she'd be interested in coffee. He proposed a time and a nice place he knew that was near his work for a few days later on Saturday.

He figured he'd check again in the AM and so he went to go take a shower before bed. He stripped out of his clothes and grabbed his towel - then his computer pinged again. He walked over - a new message. "Prove you're real! What are you doing right now?"

He frowned. Should he go risky or should he keep it light. He decided on light. "I'm just getting ready for bed!" He replied, then added "Prove you're real!" He hit send.

He sat back down and waited. "A bit early for bed isn't it? Is it proof enough that I am responding like a real person?" He grinned.

"Yes, that's fine." He started to text. "And yeah, it's a bit early. I was going to take a shower first though." He sent it then started to get up.

Ping! "A shower? Who showers at night?"

He sat back down. "Me! Makes my morning easier to get through."

Ping! "Well, maybe I could convince you to stay up a little bit longer? Put the shower on hold!"

This seemed to be going well. So he decided to play along. "Okay! Shower is officially on hold. What are you doing?"

"Drinking some wine while lounging. I just got home a little bit ago and wanted to unwind!" He recalled from her profile that she worked at a tire store.

"Up late slinging tires?" He asked, to show that he actually read her profile and didn't focus on the pictures alone - even though their was nothing really risque. Mostly face shots.

"Kind of! I had to review inventory and place some orders. Newbies like you are now starting to realize winter tires really are necessary in the WHITE Mountains. All the natives got theirs on a few weeks ago." He laughed.

"Yeah I still have all seasons. Not good enough?" He figured he knew the answer already, but he actually was enjoying this.

He could almost hear the disappointment, even though he hadn't heard her voice at all. "No. What do you drive?"

He hesitated. He hoped she wouldn't judge to much. "2002 Toyota Corolla."

There was a long pause. "After we meet up for coffee you're coming with me to my store."

He grinned, "Wow! Two dates in one day! We're moving quick!"

They continued to talk for the rest of the night, casually chatting and getting to know each other. He finally went to bed around 1am, having not taken his shower. It was great. It felt natural and fun. He even got her name: Susan. The next day they picked up right where they left off. He came home but she didn't log online till a few hours later. "Another rough day at work?" He began.

"Just busy! I'll be crazy busy for a few more weeks, then it will slow down for a while. How are you? Did you ever take a shower last night? I felt bad keeping you up so late."

"Nope, never did. Got all ready but enjoyed talking to you!" He responded back.

"Got ready? Wait! Did you actually get naked and then just chat with me with just your towel?"

He blushed a bit, but decided to take a risk. "Well, no towel."

"OMG! LOL! That is hot! I wish I had seen that!" He breathed out a sigh of relief. She wasn't creeped out. A new message quickly followed. "Wait you should totally take a shower. You'll get your clothes all dirty."

He laughed, "Okay! I'll go take a shower!" He quickly got up and did just that. He came back to a few messages.

The first one was just a simple thumbs up. This was followed by a "I wonder how long you'll take?" Then this was followed by "Come back to your computer before anything else!" and that was followed with "Like getting dressed."

He laughed and sat down, "I"m back! Came straight to my computer!"

The messenger pinged again, "Did you enjoy your shower?"

He grinned and replied "Yup. Felt good to get soapy and rinse off the day."

"I bet! So you're still naked right?" She did say she was direct.

"Yup! Completely!" he sent it back with a grin, already he was getting hard thinking about her response.

"Nice! I'd love to see if you're comfortable with that. Just on here is okay."

He paused. Was he? The chat program allowed you to upload pictures. He decided to get clever, and grabbed his cell phone and took a picture but didn't show anything. The angle was awkward, and he kept his face out of it, but you could tell he didn't have anything on. A few seconds later, "Oh wow! That is so hot! Though I wouldn't mind seeing some more!"

She sent a winky face next, followed by "Something to help?" A second later a new image came through, of what was obviously her cleavage in a tank top.

He thought he was hard before. He was very hard now. He started to rub his dick. He was fully erect, nine hard thick inches that Susan would probably really like to see. But he couldn't not focus on the curves in front of him.

He was pulling his cock slow and hard, fully working his shaft when his computer pinged again, "Don't cum without taking a nice picture first! I can't wait to see what I've caused! Unless you're doing this all one handed, then I'm sorry I'm rushing you!"

He grinned and grabbed his phone. He hesitated a bit because it felt wrong, but she really wanted to see. He finally gripped his cock firmly and got a good shot where she could see how thick and long he was. He sent it off. He didn't have to wait long for a response.

"Wow. That monster is crazy." An open faced shocked emoji followed. "That thing is huge! I can't wait to see it up close!"

He grinned and started to stroke a little faster. He sent back a new message, "Now I'm typing one handed for sure!"

"Me too!" She responded back, a little delayed. "I'm dripping looking at your cock."

That was enough to help him get over the top and he started to cum. He cleaned himself up, and when he got back he had a new message. "I'm sure you're going to cum, I know I am." Then another message came in, "Change that: I did!"

"I'm glad you liked it!" He wrote back.

"Please! I'm begging you! Don't put that gorgeous piece of meat back into pants! That thing deserves to be free."

Kyle laughed "So go to sleep naked?" He stretched out and snapped another picture. He sent it off. "Like this?"

"YES! Oh that's perfect! Look at your cock just resting there on your thigh! That is so hot! I wish I was there to run my hands over you."

"I wouldn't be sleeping then!" He grinned.

"Yeah but you'd be having a much better night. But it is late - you should get some shut eye. Can't wait to see you in person."

Kyle went to sleep knowing the rest of the week would fly by. And it did. He wasn't sure what he was doing at work but it seemed every time he turned around he was watching another day go by. He was very excited to meet Susan, and when it was finally close to time he rushed out the door. He was nervous, but managed to get there on time without incident.

He waited nervously, but Susan showed up early as well. "Kyle?" She asked, her voice a little hesitant. He nodded and she sat down. Shew as gorgeous, even wearing a simple tshirt and jeans. She was curvy, with large breasts, and gorgeous hips which her jeans hugged very suggestively. He offered to get her a coffee and when he came back she grinned, "I wasn't sure at first as I have spent the whole week looking at different pictures then your main profile one."

He blushed but grinned, "I liked yours too."

She grinned, "Yeah these girls are great at getting attention!"

They both laughed and got to talking. They had a lot in common and were enjoying each others company, with one coffee quickly turning into three then snacks. Finally, Susan looked outside. "Look, I promised I'd take care of your car! Why don't we head to my shop?" Kyle nodded and they stepped outside. "Mind if I drive your car?"

"It's a standard! I'm sure it's fine but wanted to let you know." Kyle wasn't sure. Should he go with her? He just met her! But if it was just his car - that should be okay?

"No problem for me." Susan smiled

Kyle shrugged and handed over the keys. They got in, and she started it up. She pulled out and started a running commentary on how the car handled. "With older cars you have to treat em right. More care and more maintenance. Toyota will last forever, but you've got a typical front wheel drive which is good - you don't want rear wheel drive in the heavy snow, but it isn't all wheel drive." She continued to talk while Kyle tried to pay attention to her words and not the way the seat belt was hugging her chest.

"This car handles well. I like that it's a stick shift." She was handling the car well, "You know why I like stick shifts?"

"More control?" Kyle guessed.

She grinned. "Kind of. Stick shifts are kind of like guys. You grab hold and tug right, and the engine will purr."

He laughed. "I can see that." Again he just sat there and admired her legs and the way she shifted her hips as she maneuvered between brake, clutch and gas.

She knew he was checking her out, as he had been pretty obvious about it. She decided she wanted to check some stuff out as well. "Why not pull out your own stick and I'll show you what I mean?" She grinned.

He paused for a moment, but a second later he did just that. He was rock hard, and his cock was straining to be out. As he unzipped and unbuttoned, she could see the bulge in his boxers. He slipped them down and his cock sprung free. She squealed. "Oh that's what I'm talking about!"

She quickly got them up on the highway so she could cruise for a bit and moved her hand over to what she really wanted to drive. She grasped it, wrapping her fingers around the thick shaft and squeezing. She loved how hard and long it was, and how her fingers didn't even touch. This was a really excellent cock, hard and responsive to her and she held it firmly in her strong hands. She began to stroke him lightly, not trying to get him to cum but using her hands to explore every one of the nine inches he had. She loved the slight curve, the way the head bulged out so hard and rigid, and the base where she could slide her hand down and cup his balls. Over and over she did this, going up and down with a solid firm grip. He was squirming harder and moaning a bit so she decided to take her hand away. "God that thing is marvelous." She murmured.

A few minutes later she used an exit ramp to get off the highway and turn back. She had blown past their exit. "Oops! I was a bit distracted!" she said with a grin.

"Oh no worries. That was incredible." She beamed at his compliment.

After getting off at the right exit she quickly got them over to her shop - a small, single story cement block structure that had at multiple points been a gas station, service center, and more. A single gas pump remained, with an old tow truck parked on the side. A few tire displays were set up in the large window, while an old rusted sign on a pole simply stated "Tires". This was a fairly rural area, so the phone number didn't even include an area code. Kyle looked around a bit as Susan parked. He pulled his pants up and got out with her.

Susan quickly opened the bay up, and handed him the keys. "My office is through there." she pointed to the door. "I'll get your car in and get started. Why not go in there where it's a bit warmer?" He nodded and he went and unlocked the door and stepped inside. The front area was nice. Clean, well cared for, with nice displays and prices. Susan's picture hung on the wall with what he assumed was her mother, next to a framed certificate. An old computer, phone, and printer were also on the front desk. A single door marked "Office: Employee's Only" was behind the desk. Another door marked "Restroom" was over to the far side away from the service area.

He opened the office door and stepped into what was a very neat and nice office. A better computer sat on a nice desk, which was remarkably clean. A few filing cabinets dominated one wall, and there was a door to exit to the back area. A small kitchen/break area was next to the back door, and on the opposite side was another restroom.

He took a seat on one of the chairs in front of the desk and took a moment to absorb everything. Susan's name was on the desk. She was on the front wall. He didn't think she worked here - he thinks she owned the place. He was impressed. He was also impressed with how well organized it was especially compared to many of the shops he had been in. Yes, there was signs of oil stains and grease, which is to be expected around cars - but it was obvious that she was going out of her way to keep her work area as neat as possible.

He heard the air impact wrench going as Susan got to work getting his tires changed. He had gotten himself oriented in her office and that's when another subtle change hit him. Many service stations had Sports Illustrated swimsuit calendars - Susan did not. Oh she had skin on her wall - but it was full frontal naked men. Some were just naked, some were tied up, some were naked with fully clothed women. He grinned at that. Of course she had that up on the wall.

After about twenty minutes, Susan came back. "Okay I have your 'all season' tires off your car. They're going to go in the garbage. The tread was non-existent. You're very lucky I pinged you!" She laughed. "I'll have your winter tires on in a few. Then we can talk about how you'll pay me back!" She grinned and winked, before heading back out to the car.

Another twenty minutes and she was back. "Okay, all set." she went to the sink to wash her hands, then turned towards him with a grin. "Should we pick up where we left off on the highway?"

"Here?" He asked, knowing the answer was probably yes.

She nodded, and he immediately started to get his pants off again. She came over to help, pulling his hands apart so she could hungrily get at that cock. "All the way." she whispered as she pulled his pants and boxers down with one sharp tug. He quickly squirmed out of his shoes and kicked his pants away while tugging off his shirt. Now fully naked, Susan pushed him back to the chair he had been in. He sat down hard and she was on him grabbing his cock and burying her face in his groin to suck on his balls. He was going to help her get undressed but that didn't seem to be on the menu and after about two seconds of her going at his cock and balls - he didn't even care.

She was in heaven. She loved cocks - the thicker and longer the better. She was jerking him, licking his shaft, savoring every inch she could. Susan wanted this cock to add to her list. Sure, she liked Kyle well enough - only reason she was willing to help him with his car! But she was obsessed with his cock. And she was going to milk him till he shot his load as high and as far as she wanted. She had a ton of experience, and was putting all of it to work - switching between pressure and teasing to drive him wild. Based on how he thrust his hips and moaned in pure pleasure, she was doing a good job. But she wanted it all - not just the cock but the cum, she wanted to watch him blow his load and cum all over. She hoped it was explosive. She had been fantasizing about it since he sent that first picture.

"Oh god! I think I'm going to cum." He moaned.

"Good! That's what I want. I want you to cum for me. Blow that load!" She begged him, her voice low, sultry and earnest. "Cum like you've never cum before." She started going harder, feeling his cock begin to twitch and pulse as the cum flowed up like a volcano. She was transfixed. As he started to cum she couldn't look away - he was perfect. Shooting load after load onto his stomach as her hand remained locked around his shaft, marveling at the power she could feel through her fingers that hurled that beautiful cum so far.

He finally collapsed into the chair and she stood and leaned over him to kiss him, while not letting go of his cock. "That was amazing!" She purred.

He gasped for breath and kissed her back. They made out for a bit while she continued to stroke his cock. He was semihard but not fully erect not that she seemed to care. She sat down on his leg, balancing carefully to lean down without tipping over the chair. He wrapped his arms around her and moved his hand to start feeling up her breasts. She kissed him even harder and he started to get hard again. "Mmm." she murmured. "I think I know what comes next, but maybe we should head to my place?" She gave his cock a suggestive squeeze. He nodded. "Okay get cleaned up and dressed!" She reluctantly got up and as he stood she didn't let go of his cock.

"I kind of need my cock back if I'm going to get dressed."

She paused. "I mean, this is a really rural area... If I drive there is no reason you'd have to get dressed."

He laughed. "You really like my cock don't you?" She nodded her eyes staring right at it.

He shrugged. "Okay, I'll go fully naked but could you do me a favor?"

"Name it!"

"Could you show me your tits? I'd love to play with them a bit before we go, and I know you'll need a shirt on while we drive but do you need a bra?" She grinned and let go of his cock long enough to unhook her bra and take it off through her shirt. "Tease!" he laughed as he stroked himself for her.

Finally she lifted up her shirt, letting her large breasts bounce free. He was transfixed. She pulled her shirt off and grabbed his cock again while he came in and began to kiss and suckle at her nipples. Her breasts really were one of her best features. Large, full, firm and bouncy with perfectly round pink areolas and firm nipples. Kyle was obsessed and on them, wrapping his arms around her and pulling her into him while she enjoyed his now raging erection. "Do you want to cum on my tits or do you want to go back to my place and have a chance to fuck me?" She laughed.

He groaned but pulled away. "Your place of course!"

She giggled and suggestively bounced her tits for him before putting her shirt back on. "Okay. I'll grab your clothes." She did just that, bending over to pick all his clothes while he got his shoes back on. She never let go of his cock either. Everything grabbed, she led him back to his car with his cock like a leash, and had him get in. Instead of going around, she then crawled in over him, making sure to grind her pussy up against him before slipping into the driver seat. He couldn't help his hips thrusting up at her as she crawled over him.

Finally, she started the car, and as she pulled out and got them going he kept firm hold of his dick and mimicked her shifting the car into gear. She laughed, but as they got on the road she swatted his hand away and got her hand back around his thick member. "We're not far!" she said "I live pretty close by."