Dating the Boss Ch. 01

For most 28-year-olds they spend their Friday nights in one of three ways; at a party with friends, on a date with a lover, or at home binge watching on their favorite shows. However in the case of Aiden Andrews he was doing none of the three, instead, the young black man was at the server room of Harmony Insurance. The reason why he was working late was because earlier today a trojan horse got in the building's network. Although Aiden was able to find the trojan and then delete, he still had to reboot the entire network and make sure it didn't make any copies.

"There, everything should be squeaky clean." Aiden said as he ran a final diagnostic test.

Getting his satchel, Aiden was about to enter the elevator when suddenly he heard crying. Following the sound, Aiden discovered that it was coming from the women's bathroom. Entering the room he was shocked to find that the crying belonged to his boss Amy Yamamoto. The 32-year-old Japanese woman has long black hair in a bun ponytail, soft blue eyes hidden behind her black frame glasses, and a fair voluptuous body. She was dressed in a black blazer with a white buttoned dress shirt underneath, a knee length pencil skirt that was the same color as her blazer, and pump heels with stockings that were the same color black as her skirt. The young boss was looking at herself in the mirror with tears still streaming down her cheeks. At first Aiden was thinking about just leaving her in her sadness but his consciousness got the best of him and the young man decided to confront his boss.

"Hey Ms. Yamamoto, is everything okay?" He asked.

"M-Mr. Andrews," She said wiping away her tears before looking at him. "What are you doing here?"

"I was fixing the network, remember?"

"Oh right, well, it seems that you are finished so be on your way."

"I will, just as soon as you tell me what is wrong."

"Mr. Andrews please I am just fi-fi-fi-"

The reason why Amy wasn't able to finish her sentence was because she immediately started to cry once more. Reacting on instinct Aiden closed in on her and wrapped her in a hug which she accepted. Feeling the warmth that was radiating off of her co-worker, Amy left out a small smile and hugged even harder.

"Thank you for that Mr. Andrews." She said letting go of Aiden. "I feel much better now."

"No problem, now, what's the matter?"

"Well Mr. Andrews I may have caused the virus that infected our office today."

"What, how?"

"I opened up an email on my work computer."

"What was on the email?"

"It-It was a dating website." Amy said blushing crimson at the cheeks. "For people who have a busy schedule."

At this moment someone would either laugh at or get annoyed at what Amy did, but instead, Aiden looked at her with his chestnut eyes and asked a simple question.

"Have you eaten yet?"

"H-Huh?" Amy said in confusion.

"Have you eaten yet?" Aiden repeated the question. "I mean it's almost nine and I haven't eaten yet so I was wondering if you have?"

"N-No."

"Great." Aiden said as he grabbed Amy's hand. "Then you can come with me to dinner."

Before Amy could say anything, the two were already on the elevator heading towards the parking lot where Aiden's car was located.

***

After driving around for 15 minutes Aiden was able to find a nice little diner. Parking the car, he opened the passenger seat door and walked with her inside of the diner. Sitting down at the booth the two sat in silence before Amy spoke up.

"Mr. Andrews, why are you doing this?"

"Doing what?" Aiden asked. "And please call me Aiden."

"Taking me out for dinner Mr. A-I mean Aiden." Amy said. "I mean I just had you waste your entire night on something that I did, wouldn't you much rather be doing something else than be with me?"

"It's no problem at all Ms. Yamamoto." Aiden said. "I mean how I usually spend my Friday nights are typically playing video games still midnight so it's nice to change things up."

"Well thank you Aiden, and please, call me Amy." She said.

With the awkwardness out of the way, Aiden and Amy began to engage in deep conversation before a waiter appeared to ask what they wanted to eat. When they were finished eating the two headed back into Aiden's car where they once again drove around the city before Amy pointed something out.

"Oh let's stop there." She said pointing at the park. "I love coming here during my days off."

Parking the car, the two ventured into the vacant park. Finding an empty bench they sat down together where they looked up the lake where it was reflecting off the midnight sky with twinkling stars.

"Amy, I need to confess something." Aiden said.

"What is it Aiden?"

"The reason why I didn't get upset is because for the last couple of months I have been trying to find the courage to ask you out."

"Oh." Amy said in shock.

"Yeah, so when I heard you cause the trojan horse because of a dating website I saw my opening." Aiden explained. "I hope I didn't take advantage of you in your predicam-"

Before Aiden could finish his sentence Amy kissed him on the lips. Although it felt like minutes it was more likes hours as the two were feeling sparks like they never had before. Upon departing they looked at each other deeply in the eyes and smiled.

"Close your eyes." Amy whispered into Aiden's ear.

"Okay."

Closing his eyes, Aiden felt something (or most likely someone) get on his lap.

"Open them." Amy said.

When he opened his eyes, Aiden was now staring directly at Amy's bare DD chest as the moonlight kissed upon her breasts. With the cold breeze touching her breasts her pink nipples popped out of her half dollar sized matching colored areolas. Seeing the two beauties before him harden Aiden's penis and plastered a smile on his face.

"Well, what do you think?" Amy asked.

"Beautiful." He softly said.

Kissing the left breast first sent a shock wave throughout Amy's body and resulted in her to moan loudly. As Aiden was kissing her breast his own penis was getting harder to the point that Amy was beginning to feel it. Using her hand, Amy unzipped Aiden's pants and fished out his 10 inch chocolate penis. Positioning it, Amy placed Aiden's penis inside her vagina where a trickle of blood began to seep out.

"Amy are you?"

"Yeah." Amy said with a nod.

"Huh, same here." He said.

With the two chuckling at the moment they were having Amy pushed down on Aiden's penis where she began to feel the full size of the penis. Using his hands, Aiden pinched Amy's nipples which made Amy bite down on her bottom lip. Having a combo of pleasure like never before the two climaxed simultaneously. Resting in each others arms, Amy and Aiden looked at each other before speaking.

"I know this may seem a bit inappropriate but are you on the pill?" Aiden asked. "If not i'll make sure to be there for the kid."

"Don't worry." She said. "I am; so are we like officially dating?"

"Yeah, I guess so." He said. "Should we notify this to H.R?"

"Nah, I think the less the office knows the better."

"Good point." Aiden said. "Allow me to take you home."

With the two adjusting themselves, they departed from the park holding hands with smile on their faces. Little did the two know that this will be the start of something that the two never experienced before in their lives.