Jimmy's Well-Paying Summer Job

With just a few weeks left in the summer before Jimmy left for his sophomore year of college, he was working as many hours as he could to save money before he left for school.

During the week he worked for a local insurance company as an intern to help satisfy a requirement of the business degree he was working towards. On the weekends, Jimmy worked for a small company a family friend owned in which he would help deliver and set up tents and tables for parties and other events. Jimmy liked working with his hands and being outside as much as he could in the summer, so he enjoyed his side-job, even if it took up almost all of his summer weekends.

"I don't mind giving up my weekends at all right now, my social life back at school will more than make up for the lost time in the summer." He explained to a friend when asked why he was always working.

Although Jimmy had been enjoying his internship, he had a strange affinity for the more manual labor he had to do on the weekends. Hauling large tents and canopies, tables, chairs and other necessities for events like graduation parties and family reunions, among other things. He liked that he was doing physical activity and working outside.

During his first year of college, he and a friend from his hometown became mainstays at the gym on campus and he had really built up his body. He was now more muscular and loved the newfound confidence it gave him. His summer side-job gave him the ability to put his strength to use and get more activity outside of the gym.

On occasions where Jimmy and his coworkers were setting up in a park or public space away from someone's backyard, he and his coworkers could take off their shirts and take in the sunshine while they worked. He had developed a nice tan as a result.

Jimmy was positively brimming with confidence.

However, Jimmy was also feeling frustrated. His girlfriend, Kayla, who he had been with for the last two years spanning high school and his freshman year of college, was starting to become a source of stress for Jimmy.

He loved her, and they had stayed together after attending different universities, but it wasn't anything about Kayla's personality, per se, that was bothering Jimmy. Kayla came from a family of devoutly catholic parents and while she didn't necessarily buy into the doctrine to the extent that her parents and older sister did, there were some parts of Jimmy's relationship with her that were affected by her beliefs.

Jimmy was now 19 years old and going into his second year of college as a virgin.

He respected her beliefs and loved her, so he put up with her stubborn refusal to have sex because the rest of it was worth it to him. They did everything else sexually, she was great at it all, and Jimmy was gaining valuable experience in many respects. But he wanted to have sex.

While he ultimately wanted it to be with her and no one else, Jimmy was beginning to wonder if maybe it was time to move on, especially since it was about to be another school year spent six hours away from each other by car and he had already spent his first year fending off women left and right in the name of his relationship with Kayla.

Jimmy now couldn't seem to shake the thoughts in the back of his mind that maybe it wasn't worth it anymore and he was missing out on a lot of things...and girls.

However, every time Jimmy was with Kayla, the only person he'd make time for on weekend nights in the summer after he got off work, he remembered why he had stuck with her. It was just dealing with his thoughts the rest of the time that he was increasingly worried about.

On Saturday night after Jimmy had finished up with work, he came home, took a quick shower and rushed out to meet Kayla for dinner at their favorite place in town. They ran into a couple of mutual friends afterwards and all went out for ice cream together.

"How's the working life, Jimbo?" His friend Brian asked. "Seems like running into you randomly on the street is the only way to see you out anymore."

"It's taking up almost all of my time, but its worth it. My mom and dad don't want me working while I'm at school so that I can focus on my schoolwork, so I want to save as much money as I can for the year. I'd love to hang out more, but I just have so little free time"

"And the time he does have belongs to me!" Kayla said with a laugh as she nuzzled her face against Jimmy's chest.

"Well if you ever have any time between now and the end of summer, let's get out to the beach!" Brian's girlfriend Stacy said.

"Kayla and I go all the time and she just talks about how much she wishes you could come too." She added.

"Definitely!" Jimmy replied. "I've really missed it this summer, so I'll find a Saturday or Sunday later this month and call in sick." Jimmy said with air quotes indicating a fake illness to get out of work.

"Awesome man, let's do it! See you around!" Brian said as he and Stacy went on their way.

"What now?" Kayla asked Jimmy with a sly smile that betrayed the fact that she knew exactly what the rest of the night had in store.

Earlier that week, Kayla and Jimmy had made plans for this weekend knowing that Kayla's parents and sister would be away at the family's lakehouse a couple hours away. They had her place to themselves and fully intended to take advantage of it.

Jimmy smiled back then looked at his watch. "Well it's about a ten minute walk to your place from here, which means in about, oh eleven minutes," he said as he looked to the sky while doing some quick estimating out loud, "I'll have you out of that dress and all to my myself."

"Let's walk faster then," Kayla said. "I don't want to wait eleven minutes for that."

Jimmy kissed her and laughed and they were on their way.

They made it to Kayla's house in eight minutes. Eleven minutes after Jimmy's initial estimate of the time it would take to have Kayla out of her dress, she was straddling jimmy as he sat on the couch in the basement of her parents' house, their normal hang out spot.

Kayla's dress was on the floor with Jimmy's shirt. Now in just her tiny light pink underwear, she was leaning back panting with ecstasy as Jimmy's lips moved down her neck to her collarbone, slowly and sensually making their way down her slim, fit body.

Kayla loved Jimmy's foreplay, even if foreplay was technically all they ever did.

Jimmy had a sensual touch and knew just how to pace himself as he felt and kissed her body to get her squirming with excited sexual pleasure and frustration.

He knew just where to kiss her too.

First, he would kiss her neck just below her ears before pulling away slightly and hanging just centimeters away from her ear as she eagerly anticipated what was next. When he would kiss and gently suck her ear lobe, a chill would run through her body every time.

Next he would move back to her neck, slowly kissing and sucking as he moved down to her collarbone. He would kiss along her clavicle as his hands moved on her back. In the instances where she was wearing a bra, he would skillfully unclasp and remove it. Tonight, with no bra beneath her sun dress, that step was unnecessary.

Taking his time, he moved down to her exposed right breast. He breathed heavily on her body as he kissed her, making his way to her nipple.

Kayla was a petite girl with tight body which she kept fit by playing soccer in high school and college with the occasional beach volleyball games mixed in during the summer. She had relatively small B cup breasts that were the very definition of perky. Her pale pink nipples were somewhat large in proportion to her breasts, with a slight puffiness that Jimmy absolutely loved. Her sunkissed skin made the tan lines on her breasts stand out and Jimmy loved how her areolas sat just inside the tan lines. It was as if her barely concealed nipples in her bikini were a sexy secret only Jimmy knew.

As he kissed her breast, he took her nipple into his mouth where he slowly circled it with his tongue, applying slightly more pressure each time he went around it.

Kayla gasped with pleasure. Her nipples were sensitive and she went wild for Jimmy's tongue when he used it this way.

He was setting her body on fire with sexual energy.

Suddenly, Jimmy stood up, holding Kayla up with his hands just below her ass. He pivoted quickly around towards the couch and laid Kayla down in a low slouch against the back of couch with her waist jutting out towards him, hanging just past the edge of the front of the couch.

Jimmy looked up at Kayla, meeting her eyes. He gave a sly smile as he began kissing her stomach and she returned it with a playful laugh and moan of expectation and desire.

If Kayla loved Jimmy's tongue on her sensitive nipples, she didn't even have words describe how much she enjoyed what he was about to do with it now.

As Jimmy moved past her belly button, he gently spread her legs and lowered his face until it was hovering just over her light pink panties.

He smiled as he took in the sight of the growing wet spot in the middle of her underwear.

He loved to take his time here. He would move to her left thigh and begin kissing her leg about eight inches down from her crotch and laid small, gentle kisses progressively higher up her leg until he was just at the edge of her panties.

Kayla, now with eyes closed and slipping deeper into a state of relaxation and uncontrollable pleasure, moaned softly as Jimmy moved his face over her panties, brushing his lips over the wet spot to give her aroused lips the slightest of sensations.

He kissed her right thigh the same way as the left as he began to pull down her panties.

After removing them, he brought his face directly over her pussy which was now positively drenched. As he lightly kissed her swollen lips she softly gasped. Taking his time, as always, Jimmy went to work slowly and softly with his tongue.

He moved up from her lips to find her aroused clit where he began circling it softly and applying more pressure and speed as he went along, just as he had with her nipples. After another few minutes of this, varying his pace and pressure with his tongue, Kayla was panting and moaning uncontrollably.

Her legs began to twitch along with her tight, toned ab muscles, and she began squeezing Jimmy's head with her thighs as her cries of pleasure became louder.

Jimmy kept up his pace and rhythm as he smiled to himself. He absolutely loved it when Kayla began squeezing his head between her thighs. He could feel the unbridled sexual energy and pure pleasure radiating from her body telling him to keep doing exactly what he was doing without ever saying a word. Not that she could put a coherent sentence together in this state anyway.

Suddenly, she squeezed her thighs on his head as hard as she could as her hips bucked and gasped repeatedly and involuntarily. A second later, her entire body tensed up, and released in a wave of bodily motions accompanying her loudest single cry of pleasure.

She reached down with both of her hands on his head as he continued to circle her exploding clit with his tongue as she continued to squeeze his head with her thighs. Her body moved in a wave from head to toe as she reveled in the deep orgasmic pulses Jimmy's tongue was sending through her body.

Again, she tensed up and cried loudly with pleasure. Jimmy slowed his tongue and gradually lessened the pressure on her clit as she came down from her second orgasm. He knew this was always the point where she'd had enough, even if they both wanted to keep going.

As he slowly, gradually ground to a halt, Kayla turned her head to the side and laughed softly. A reaction of utter ecstasy and disbelief.

"Well, you got me again." She whispered with a smile after opening her eyes to look at him for the first time since he really got his tongue going.

"It's what I do." Jimmy said as he moved beside her on the couch and gently changed her angle so that they were now lying down on the length of the couch, his body behind hers, touching at all points as if they were one.

On Monday Jimmy went in to his job at the insurance company. As he did on most days, he had lunch with his friend Justin who was also doing an internship at the bank next door.

Jimmy seemed a little out of it to Justin so he asked, "What's up, man? You're usually a killer on Mondays. You're usually weirdly excited about all the work you have lined up for the week."

"I don't know, just distracted." Jimmy replied.

Justin was a good friend of Jimmy's and they had gotten even closer at college. He was also one of the few that knew about the nagging thoughts in the back of Jimmy's mind about his future with Kayla.

"Something happen this weekend?" Justin asked, having an idea of what the issue was.

Jimmy gave Justin and sideways glance, knowing that he had hit the bullseye.

"I don't know what the problem is. Everything with her has been going exactly like it always has, I'm not bored with her, we don't fight, but I can't help feeling like I have to make some kind of decision on what to do with her."

"What happened?" Justin asked.

"It was a perfectly fine night, just like always." Jimmy said as he propped up his head with his left hand. "We had a great dinner, went to her place and everything was great. I did her, she did me, we were both totally satisfied. ...But its like there's this thing hanging out there between us and I can't even talk about it. Every time I try to bring up moving to the next step between us, she shuts it down. Its like we're so far away from it that we aren't having a conversation about when we'll be ready to do it, but talking about when she'll be ready to talk about doing it."

"Did you bring it up?"

"No." Jimmy said. "I didn't want to ruin the night."

"Well, man, this is all obviously up to you, but the way I see it, you want to move to the next level with her and she won't even let you talk to her about it. On top of that," Jason continued, "you're spending all this time apart from her during school and the clock is ticking on making this happen. I'd say its time to force the conversation and let her know how you feel and that it's affecting your relationship."

"Yeah, I think you're right."

*******

On the following Saturday morning, Jimmy got a call from his boss letting him know that Jack, the coworker scheduled to deliver a small tent with tables and chairs for a birthday party that day was out sick. He asked Jimmy if he thought he could handle the job on his own since it was a small event with manageable equipment for one person and Jimmy said he could.

It was a hot and sunny day on during the second week of August. Jimmy had just one more weekend of work left with the event supply company after this one. The week after that, his internship would end and he'd be back at school the last week of the month. Summer had flown by and he still hadn't resolved his issue with Kayla. She knew it was on his mind but was so dead-set against taking each other's virginities right now that it wasn't weighing on her mind like it was his.

Jimmy was frustrated, so he was happy to have a day of work outside by himself where he could be occupied and think things through while he worked.

He drove to the warehouse where all of the tents and supplies were stored, found the work order, and began loading up the truck with the equipment for the day.

"A kid's birthday party." He said as he looked over the order. "This should be pretty easy."

Jimmy made his way across town to Harborside, one of the nicer neighborhoods in town with large houses on big plots of land. He had always thought Harborside was a stupid name for this place since it was set back in the woods on the eastern edge of town, precisely the farthest point possible from the harbor and the beach.

He made his way through the neighborhood keeping a close eye on the mailboxes looking for the address of his delivery spot. The houses were all pretty far apart from each other and set back a good way off the road in the trees. Privacy was a big draw for the people who bought in this area, and Harborside had it in spades.

Finally, he spotted the driveway he was looking for, with birthday balloons tied to the mailbox off to the side, and made his way up to the house.

He pulled up just before the garage, a separate structure from the flagstone house with large, steep gables, and put it in park.

"This looks like one of the smaller places in here." He said to himself, still impressed by the size and look of the house.

He walked up to the front door and rang the doorbell. After a minute or so had passed, he rang it again.

He heard the distant voice of a woman from inside yell, "Coming!" After another 30 seconds or so, the door opened.

"Hiiiiii!" The woman in the doorway exclaimed when she opened the door. "Are you here to set up the tent?" She asked excitedly.

"Um, yes, I've got the tent, tables, chairs, and...um...everything else here in the truck." Jimmy pointed back over his left shoulder towards the driveway while not breaking eye contact with her. "I just need you to show me where you want everything."

"Oh yeah, ok!" The woman replied. "Just come go around back between the house and garage and I'll meet you back there."

She closed the door and as Jimmy took a step back towards the driveway he whispered to himself, "Holy shit."

She was stunning. Small and petite like Kayla with deep green eyes that captured his gaze the instant his eyes met them. Her long, thick, black hair, was pushed over the left side of her head in an uneven part from the right. It looked gorgeous to Jimmy even if he suspected she hadn't styled it yet that day.

Her clothes seemed to confirm his thoughts. She was wearing very short, pink cotton gym shorts, and a loose fitting light blue v neck t-shirt cut close to the shoulders. Loose as it was, Jimmy could see that while she was small in stature like Kayla, she wasn't small in the chest like her.

Jimmy made his way around the house trying to snap out of it. When he came around back, she was just walking out the back door on to the patio next to a large in-ground swimming pool. She dodged a chair and made her way toward him in the yard.

"Hi, I'm Diana!" She said, holding out her hand to introduce herself.

"Jimmy." He said in return, shaking her hand firmly and looking her straight in the eyes like his life depended on it.

"Hey Jimmy, thanks so much for your help with this!" She said as they held eye contact a second longer than normal.

"Uh yeah, no problem. Just show me where you want the tent and how you want it oriented and I'll get to work"

She led him about twenty yards back from where they exchanged introductions, into the shaded part of the yard and gave him the details. After a quick rundown of the list of supplies, Jimmy headed back to the truck to get to work. As they both walked back across the yard, he slowed a bit to get a better view of her from behind as she turned toward the backdoor of the house.

For a woman only about 5'4, her legs were slender and magnificent. Toned but not bulging with muscles, it looked like she took care of herself. Her ass was small and by no means her best feature, but Jimmy wasn't much of an ass man anyway.

"I wonder how old the birthday boy or girl is, there's no way this chick is a day over 40." He thought to himself while mesmerized by her legs.

As he was taking in the view below her waist, he didn't notice that she had turned her head slightly back toward him and caught him looking.

Jimmy got to work in the truck getting the tent poles and canopy out on the cart to take them to the backyard. He was already beginning to sweat in the heat of the day, magnified inside the trailer of the truck which was quickly becoming a furnace parked in the sun as it was.