Every Teen Romance Ever

Break the Rules (1/2)

Are you interested in becoming a tutor? Need experience for a future teaching job? Winchester Academy is looking for high school students ages 15-18 to tutor elementary school students on weekends for a few hours. We understand you have other commitments, so we offer a flexible schedule. Pay is $20/hr. If interested, call Dean Winchester at 1-800-420-6969.

I stared at the advertisement, my mouth open. Twenty dollars an hour? My last babysitting job had only paid me nine, and their sons Rodrick, Greg, and Manny were hell. I could tutor elementary school students. I eagerly dialed the digits and waited for Mr. Winchester to pick up.

Instead, a female voice answered. "Hi, this is Winchester Academy. How can I help you?"

"May I speak to Dean Winchester about a tutoring job? I'm currently a senior-"

"Oh, I'm so sorry, our application deadline was 30 seconds ago." My heart deflated like a balloon. "I can put in a word to Dean though. What's your name and number?" She took my info and then ended the call. I sighed, returning to the newspaper to find more job opportunities.

A week later, I was browsing TV shows on Netflix when my phone rang. "Hello?" I said, quickly swallowing the popcorn I had just popped in my mouth.

"Is this Mikayla Hampton? I'm Dean Winchester from Winchester Academy."

I almost choked on the popcorn. "Y-ya mate."

Mr. Winchester laughed, and holy hell the sound was hot. He had a deep, rough voice that was both stern and laid back, strong and subtle, hot and cold, yes and no, in and out... "One of my tutors died of butt cancer. Would you be interested in an interview?"

"Yes," I replied bluntly.

"I'm actually available right now. I'm guessing you're free?"

"Omg I am! What a coincidence!"

"Great! Come to my house- I mean, office- anytime before 3 and I'll be waiting. Address is 402 Boss of You Avenue."

"Ha, it rhymes! I'll be there!" After hanging up, I checked the time. It was 1:41. His office was twenty minutes away, so after watching an episode of Gossip Girl, I changed into a professional button-up with a small rip and torn jeans and drove to his...office? It was a gorgeous brick mansion with an arch over the door and a beautiful garden. I knocked on the door, and a stereotypical colored man answered and escorted me to Mr. Winchester's office. I gulped and stepped inside.

Holy hell. Mr. Winchester was so hot I'd work for minimum wage just to be in his presence. With those jade green eyes and full lips, his fresh-shaven face was probably the hottest on LinkedIn. He ran his fingers through his luscious tax-defying brown hair-

"Hello, Miss Hampton," He said, standing from his chair to shake my hand. He Eiffel towered above me at around 6 feet.

"Hi," I squeaked back.

"Have a seat," Mr. Winchester said before he returned to his seat behind his desk. I sat in front of him nervously. "As you can see, this isn't my normal office. Most tutors work at the Academy building a few blocks from here, but you will be working here...as my younger brother's tutor."

I swallowed, digesting this information. The house was beautiful, but I didn't know what to expect. "How old is he?"

"Sam is eight years old. He is already at the top of his class at his private school; my family just believes that wasting money on extra lessons for him will be beneficial."

I nodded. "How often will I have to come?"

"Every Saturday for a few hours."

"Okey dokes, I'm in," I replied, and Mr. Winchester smiled.

"Wonderful. Please fill out this paperwork, and you can begin this week. Thank you for applying."

*****

I had filled out all the forms. I repeated the five golden rules that all Winchester Academy employees had to follow in my head:
1. Always refer to me, Mr. Winchester, as 'sir' or 'boss'. I like to pretend that it's the 1900s and that I'm more important than I really am.
2. No lying, cheating, or other forms of dishonesty.
3. Respect the student. Abusive behavior will not be tolerated.
4. Treat others the way you want to be treated (or some other cliche).
5. Any two employees caught having a romantic affair will be beheaded. Just kidding. I'll sue you.

I entered Mr. Winchester's house, and the colored guy escorted me to his office again. I handed over the forms. Mr. Winchester thanked me, then frowned as he looked me over.

"Isn't that the same shirt you wore last time? And those holes in your jeans are not fashionable."

I flushed red, embarrassed. "Um...yeah...I'm kinda broke compared to you, sir."

Mr. Winchester shook his head. "Your appearance is not suitable to teach my dignified prodigy of a third-grade brother. We will need to replenish your wardrobe."

I gasped. "Eww I hate getting new clothes I don't have to pay for!"

He stared at me like I had sprouted a third ear. "Most girls, or just people with brains, would be dying for this opportunity. Well, you're still pretty, so I'll spoil you anyway." He led me to his car, a brand new Porsche with no top because Mr. Winchester liked everything topless ;) I sat in the passenger seat, locks of my auburn hair flying behind me in the summer breeze. When Mr. Winchester drove faster, I giggled, and he smirked at me.

We arrived at Overpriced Boutique and headed inside. A woman was assigned to do my fitting. When she saw me, she gasped. "Oh my goodness, you're beautiful! That hair! Those eyes! And a perfect body too!"

I blushed while Mr. Winchester smiled his sly smile. "She is. Please buy whatever she wants, she's my top client for no reason."

"You got it!" The woman responded, and she dragged me to a fitting room while Mr. Winchester waited outside to assess my outfits like I was in a beauty pageant and not a teenage tutor. After she got my measurements, she had me try on various blazers, dress pants, pencil skirts, dresses, and blouses. Despite my protests, she insisted I wear heels as it was more ladylike. I stepped out of the room in some classy outfits, mostly consisting of high fishnet stockings, black cardigans over low-cut tops, miniskirts, and glasses even though I didn't actually need them.

Mr. Winchester wolf-whistled when he saw me. "Damn, wish you were my teacher."

I wasn't uncomfortable at all. "Thank you, sir," I said, pleased as he checked me out. We finished bagging everything and the salesman racked up the total to be $1,738.98. I opened my mouth, about to apologize for spending so much, but Mr. Winchester swiped his credit card like it was nothing. He loaded the bags into the trunk, showing off his strong body. After he shut it, he said, "Now you're ready to work for me."

I smiled. "Yes, sir."