Good Times
Ahh September, summer holidays are over, students go back to school and everyone else settles back into their regular work routines.
This was an unfamiliar experience for Jake.
After graduating high school in June, he spent the summer ramping up the odd jobs business he and his best friend, Bruce, had started in grade seven. Bruce didn’t live right on the ridge, but was only one street over.
Though they lived in a very affluent community, Jake’s parents did not spoil or coddle him in his teen years, they merely mentored him. If he wanted something, he had to work for it.
It started off with mowing lawns and shovelling snow near where they lived. Then, once he got his driver’s license, his dad used his connections to help Jake buy his first truck.
His dad worked for a large corporation and they were always auctioning off older vehicles, but staff always had the chance to buy them before they went to auction. The trucks may have been older, but the price was right and they were all 4-wheel drive.
The truck allowed Jake and Bruce to service the whole neighbourhood. Then the next summer, Jake’s dad used his staff status to help Jake buy a second truck, which allowed more of Jake’s friends to work for him and they added garbage removal to their services. They added a third truck after graduation, and then a fourth truck in August.
Besides himself, his company now had six full-time employees and a handful of part-timers—mostly friends from high school or friends of his friends. It was a pretty efficient company, and the plan was to expand the commercial business. He had a few small business contracts, but they were strictly landscaping contracts and sidewalk shovelling, no large-scale parking lot snow removal—yet.
Each truck had two people, and they kept them booked solid. Two trucks for garbage hauling, One truck with a covered trailer with all the snow/lawn equipment and the remaining truck was his for everything else and a spare for when one of the other trucks was in for repairs. The plan was to venture into the more lucrative commercial snow clearing contracts this winter. They just needed to put salt/sand spreaders in the back and snow blades or blowers on the front.
His mom worked part-time for the company as the accountant, and the software they used handled the scheduling, invoicing and even the VoIP phone system. His mom, the accountant, took care of the payroll, taxes and also helped with dispatching if Jake was busy. Since the trucks and phones were all tied to the software, anyone could see where everyone in the company was at any moment. Plus, having the phone system managed by the software, it saved all the photos, videos and emails out in the cloud. It was a beautifully efficient and redundant system, complete with a messaging app, but could also redirect calls as required, all from a single phone number. Jake just did all the scheduling, business development and also helped whenever required.
The neighbourhood, being one of the more affluent communities that bordered the river valley was conducive to their business success. All the houses along the ridge had large yards and driveways—they had money—and were more than happy to support the local teen. They were along the south side of Fish Creek Provincial Park, one of the largest urban parks in North America, bordered on three sides by the city of Calgary and on the west side by the Tsuu T’ina Nation. Then it met up with the Bow River on the east end, which snaked through the entire city, so although the park stretched 19 kilometres, it connected to natural areas on both ends that just weren’t part of the park. The park comprised hundreds of kilometres of pathways and various amenities, but most of the park was still in a natural forested state.
His parents’ house overlooked the park from the low ridge and, like most houses along the ridge, the basements had been developed into separate residences. This practice was actually quite common along the ridge—as kids graduated high school, they could have their own place with separate entrance yet still be close to home. Then, when they did eventually move away, the parents could rent out the basement.
So, despite living under the same roof as his parents, he had his own place and moving out of the basement wasn’t a priority. Although the way his business was growing, he hoped he could afford his own place by next winter, but it had to have a garage, as that would be the maintenance shop, but he was also entertaining the idea of just leasing an actual shop.
Saturday was usually the busiest day of the week, but with it being the first weekend of September, it was even busier than normal. Everyone finally realizing all the tasks they kept putting off during the summer were still outstanding, so they simply hired the local boys to do it now that work and school schedules were returning to normal.
This meant most of the business was garbage removal and he had all four trucks doing that today.
To speed up the garbage removal process, Jake had a deal with a nearby mechanical shop and, for a small fee, they allowed them to park a large commercial dumpster at the edge of their lot. This saved a ton of time for garbage loads, as each dumpster held the equivalent of about 16 truck loads and the trucks didn’t have to drive to the city landfill and wait in line. They normally emptied the bin twice per week, but in anticipation of this weekend, they had actually ordered a second bin.
Though they started the business together, Bruce never wanted the leadership or management role. He hated doing business development, administration and sales. So he would step up and take control if Jake was sick or gone, but solely to manage crews. He was happy to just be an employee.
Fortunately, since the company was expanding so fast, new customers were calling them and they weren’t having to go out and drum up new business. Although Jake did meet with the new customers to write up the contracts.
All the full-time employees in the company were friends from school, but now that they had graduated, two of the full-time guys switched back to part-time so they could go to post-secondary schools. So Jake just partnered them together and scheduled garbage hauling jobs for after their classes.
To celebrate the end of another busy week, it was almost a ritual to visit the neighbourhood pub and enjoy a beer and a steak sandwich. Usually most of the crew showed up to steak sandwich Saturday, as they called it, but not always. People arrived straight from their last tasks for the day and they all gathered at their usual table. It was just nice to relax with friends.
After the meal though, Jake, Bruce and Mario were going to a nightclub because Mario had recently met this girl, Kate, from across the park and she had planned to go out with a couple of friends on Saturday night.
So Jake and Bruce were going as Mario’s wingmen. They were all single with fit, athletic type bodies. Jake was the youngest at 18, but he was also the tallest at 6-foot-2, with dark brown hair that was buzzed short, brown eyes and tanned skin.
Bruce was heavier set, but still in great shape. He was roughly 5-foot-9, with red hair buzzed short. He was the oldest at almost 20 since he had to repeat a year in elementary school—it was that repeat year when Jake and he became best friends.
Mario was the stereo-typical tall, dark and handsome. He was 19, an even 6-foot, with black hair, brown eyes and dark skin, partially tanned from working outside all the time, but also from his Mediterranean ancestry. He was always the ladies’ man and was rarely ever single throughout high school or since graduation. Mario had moved to the community in grade ten, so while he didn’t have the history Jake and Bruce did, they considered him a close friend. The three amigos, as Jake’s dad always called them.
He was also the main reason Jake and Bruce ever met women. For the last few years, Jake was always working when he wasn’t in school and Bruce was usually helping him, plus Bruce was quite shy, which is likely why he didn’t enjoy doing sales. It was usually friends of Mario’s latest squeeze that Jake and Bruce hooked up with.
They left the pub after their meals, and went home to shower with plans to meet at Jake’s at 9PM, since everyone was within walking distance. They would then call for a ride to the bar, so they could all enjoy themselves and no one would drive drunk.
Around 8:45, the two friends arrived at Jake’s place. Jake had already ordered a ride for 9, so they had a few minutes to talk. Mario had already been texting Kate.
As the girls arrived at the bar, she video called him and told him where they were going to be. Her friends leaned in to see who she was talking to and Mario then panned to show Jake and Bruce.
The girls were definitely attractive—maybe the change of scene wouldn’t be so bad tonight?
As their ride arrived, they disconnected the call, promising to see them soon.
Minutes later, they were arriving at the bar and Mario texted Kate to say they had arrived.
Kate actually came and met them at the door and led them to their table at the back. It was slightly quieter at the back, but Jake still couldn’t figure out why people go to nightclubs. They’re just too loud and all you do is yell at the person you are trying to talk to, but the upside is that in order to hear what they’re saying you get to lean in and look down their shirts.
Fortunately, the DJ took a break after the current song ended, allowing everyone to properly introduce themselves. Kate was a dance instructor and model, which fit Mario’s type. He always went for the tall, skinny models. She was 5-foot-8, maybe 100 pounds, with A-cup breasts, brown hair that flowed down over her shoulders and hazel eyes. Jake guessed her measurements to be around 33-23-35.
Jake had always been good at estimating weights and measures, which was helpful when trying to price the size of a driveway or lawn for service and for estimating the size of a garbage load.
Sofia was a busty Hispanic beauty. Shoulder-length black hair and brown eyes. She was 19, 5-foot-5 and around 160 pounds. She was exactly the type that Bruce preferred, since he also had a few extra pounds. Jake guessed her measurements to be 38F-24-35. She was currently studying veterinary medicine at the University of Calgary.
Gabbie was the one that caught Jake’s eye, though. She was 18, 5-foot-7, around 115 pounds, with green eyes, long blonde hair and incredible natural breasts. Jake guessed her measurements at 34E-22-36. She had plans to become a teacher. Jake normally would’ve classified her as out of his league, but the smouldering look she gave him with those enchanting eyes, captured his attention like a moth to the flame and he was hers.
After more than a few drinks, everyone was getting tipsy and flirtatious. The mixture of the two groups had been perfect. Mario and Kate disappeared onto the dance floor frequently, Bruce and Sofia seemed to hit it off, and Jake and Gabbie had already exchanged phone numbers.
As the night progressed, Mario and Kate eventually left—likely going back to his place. The rest of them barely noticed as Bruce and Sofia looked like they were going to fuck right there in the club and Gabbie and Jake were also rubbing each other, getting hot and bothered, and discussing going back to Jake’s place.
Until Gabbie received a text message.
As soon as she saw the message, the flirtatious, sexy look on her face evaporated.
Sofia recognized the look immediately and asked, “Is it your mom?”
Gabbie nodded as she excused herself. Sofia immediately followed her, but not before at least informing Bruce and Jake about what was going on. “Gabbie’s mom can be a real bitch. It’s like she can sense when Gabbie is about to have a good time and she intentionally spoils it.”
Since it now looked like Jake would not get lucky like his friends, he spoke to Bruce. “It sure looks like Sofia and you are going swimmingly.”
“Yeah, she’s great. Not sure I’m going to get lucky now, but I hope we can continue to see each other, at least we exchanged digits. Gabbie sure is hot, and she’s totally digging on you, man! Did you get her number?”
“Yeah, we already exchanged numbers as well.”
“So what’s the plan? Mario and Kate already left, and something tells me that Sofia and Gabbie will leave soon after they come back and we won’t be getting lucky.”
As if on queue, Sofia and Gabbie returned. Gabbie didn’t look like she had been crying, so maybe not that bad?
Gabbie kissed Jake and said, “I’m so sorry. My mom can be a bit controlling and I have to go. Would you like to go out, just you and me, say Monday night?”
That kiss was proof enough that Bruce and Jake’s fun was over for the night. “I would love that!” Jake said.
“I’ll text you on Monday when I get home from class and we can make plans then.”
“Sure! That sounds good.”
Gabbie gave him a kiss and let her hand roam down to the bulge in his pants. “I really am sorry. I’ll see you Monday night and make it up to you.”
Sofia more or less repeated the same actions with Bruce and promised to call him and make plans for Monday, as her phone dinged. “Our ride is here.”
Both girls gave their beaus another smouldering kiss before leaving.
Jake then pulled out his phone and called for a ride as he and Bruce made their way out into the cool night air to wait for its arrival. Then it was just a few more minutes until they were dropped off at Jake’s place as Bruce just walked home from there.
Monday morning at his dad’s garage, aka the shop, Mario bragged about his great weekend with Kate and how many times they fucked, but eventually asked Bruce and Jake how they fared with Kate’s friends—completely unaware of the drama that had unfolded with Gabbie’s mom. He, of course, apologized, but wished them both luck with the girls tonight.
Once the rest of the guys arrived, they went over the tasks for the day, the crews went to their trucks and were soon on their way. Jonathan, one of the new guys, had called in sick, so Bruce didn’t have a partner for the day, so Jake took Jon’s place. It was just like old times for them, which was beneficial since they could likely complete their tasks faster than working with others, giving them ample time to prepare for their dates.
Mid-afternoon, both Sofia and Gabbie started texting the guys. Sofia’s text messages were simply arranging the date for tonight, whereas it sounded like Gabbie wanted to play around. She said they would have the place to themselves if he got there by 4PM, and they could have some fun before going out on their date to make up for leaving him with horny on Saturday.
Jake suggested she could come to his place, but she declined, saying her life would be a living hell if she broke her mom’s rules. Jake wasn’t sure why that would matter since her mom wasn’t home anyway, but oh well.
Throughout the afternoon, Gabbie kept sending him racier and racier texts, which made working difficult, but they got done their tasks early and had enough time to grab a quick shower before it was time to leave.