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Embarrassment with a Side of Regret

Madison

I paced outside of the Morgan & Co. building. I was hesitant to go inside. I hadn’t seen him since I ran away at 16. My mother had told me that if I wanted money to survive, I had to come ask him myself. She was tired of giving me money out of the allowance she got. If I were being honest with myself, I thought she had finally gone off her rocker and moved in with her pool boy lover. That made me even more anxious about being here. I cursed under my breath before forcing myself into the building. I signed in at the reception desk on the first floor before taking the elevator up to the 24th floor. The receptionist smiled at me.

“Madison Morgan! How are you, honey? It’s been a long time.”

I shifted uncomfortably in front of her. “I… uhmmm… sorry… I’m okay, Mrs. Taylor. How are you?”

“I’m great. Is your father expecting you?”

I cleared my throat. “He’s my stepfather!”

I flushed at her raised eyebrow. I couldn’t help correcting people. I hated that my mother had married him. He was too serious and businesslike to be a good match for my mother’s flightiness. I knew she had cheated on him. She did it all the time. She was the reason that I ran away. I had caught her sleeping with my boyfriend in their marital bed. I took a deep breath to calm my nerves.

“Is he busy?”

“Not yet. He has a meeting in 15 minutes. You can go back. I’ll let him know you’re here,” she said, reaching for the phone on her desk.

I covered her hand, smiling at her. “It’s a surprise.”

She nodded. “Okay. Go on, honey.”

“Thanks.”

I hurried past her desk to his office. I knocked softly on his door before stepping back and wiping my hands on my dress.

“COME IN!”

I jumped at his sudden, angry order. I timidly opened the door.

“I’m sorry to bother you-”

“In. Sit!”

I swallowed nervously as I crossed his office to sit in front of his desk, waiting for him to look up from the papers he was reading. He ignored my presence until I cleared my throat.

“The position's salary is $500,000 a year.”

My mouth fell open. “W-what?”

He rolled his eyes. “The assistant position that I have open.”

“Why does it pay so well?” I asked curiously.

“Because you will move into my house and be at my beck and call for every need that I have at work or at home.”

“E-every need?”

“Yes. It will be a free-use situation, but you will also handle all my schedule, my errands, and my finances.”

I stared at him in shock. “For $500,000 a year?”

“Yes.” He pulled a stack of papers out of his desk and set them in front of me, still not having looked at me. “If you sign this, you will leave from here to go to the doctor to get a STD workup. If you come back positive for any STDs, the contract is void. You must also start birth control if you are not already on it. Also, when my wife is home, you will not be allowed to be in the same space as her unless I want you to join us. Is that understood?”

“I-”

He held out a pen to me as he signed the papers he was working on. “Look it over and sign and initial the parts that need you to.”

His phone rang, and he immediately answered it, brandishing the pen at me. I hesitantly took it from him before starting to read the contract while I thought about signing it. It was obvious that I wasn’t who this contract was meant for, but I kind of wanted to get back at my mother for sleeping with my boyfriend. With the image of Nathan thrusting into my mother in my head, I began to initial and sign the document. When I was done, I pushed it back to him. He didn’t even look it over before he put it in his drawer. He finished his call and went back to the documents in front of him.

“Our day starts at 9 AM sharp. You will be in my office with a cup of coffee, two sugars, and half a creamer, naked and ready to be fucked. Lunch is promptly at 11:45 AM. You will give me a blowjob while I eat. At any other time I want to have sex, you are to be ready. If you can’t get wet, invest in some lube. You are to put my dinner on my table right at 6 PM, and at 7, I will fuck you in the kitchen while you clean it. I go to bed at 10. I don’t care what you do or when you sleep, as long as you are up at 7:30 AM for work. You are not to have any other males in your life while you are under contract. Am I clear?”

“Y-yes, sir.”

“Good. Get on your knees. I want a blow job.”

My eyes widened. “R-right now?”

“Yes,” he said, reaching for another document.

I shakily got to my knees to crawl under his desk. My hands trembled as I reached up to undo his pants. He stretched his legs out beside my body as he shifted down in his chair. I licked my lips nervously as his cock sprang free of his boxers. I stared at his long, thick member as it throbbed in front of my face. Oh, God, was I really about to do this? I took his cock in my hand, stroking it slowly until his hips started moving, making my strokes faster.

“Use your mouth,” he hissed from above me.

I leaned forward to lick his tip. He immediately thrust forward, pushing his cock into my mouth. He groaned as his hand came under the desk to tangle in my hair as he fucked my mouth. I massaged his balls, and he groaned again before his seat was tilted back. His other hand came under the desk to grab the other side of my head to hold me still while he thrust deeper into my mouth. When he hit the back of my mouth, I swallowed, taking him further down my throat.

“FUCK! Do that again!”

I swallowed again before moaning around his cock. He pulled my head down as he thrust deep inside my mouth. He held my head down while he only moved a small amount to press against the back of my throat. He grunted as he shot his load into my throat.

“Take it all,” he ordered.

I sucked hard on his tip to tease all of his cum out before swallowing it all. The door opened behind me, and I froze. My face turned beet red, and he stiffened.

“Tish? Who the hell?”

He pushed his chair back to look down at me. His eyes widened in panic, and he used the hand still in my hair to pull my mouth off his cock.

“Oh, God!”

I licked a drop of his cum off my lip. “Umm… hi…”

He let me go to put his cock back in his pants. He stood up, apologizing profusely to the woman at the door as he ushered her out with the promise to call her while I stayed under the desk, too embarrassed to move. After the door shut, he came back to the desk.

“Madison, you need to come out from under there, right now!”

I buried my hands in my face. “No. I think I’ll stay here until I die.”

His arm wrapped around my waist, yanking me out from under the desk. He spun me around to face him before tilting my chin up to make me look into his eyes.

“Madison, what in the hell are you doing here?”

“I-I came to ask you for money…” I murmured, still blushing.

He pulled me against his body, hugging me. “I’m so sorry, Maddie. I didn’t know that was you. How much do you need? I will give it to you. All you have to do is ask.”

“I was going to ask for $100,000.”

He let me go to move back to his desk. He quickly wrote me a check.

“Next time, just call.”

I stared at the check in my hands before looking up at him with tears in my eyes. “I signed your contract.”

He cursed as he ran his hand through his hair. “Maddie, what happened just now can’t ever happen again.”

“But-”

“No, Madison. It can’t. It was wrong.”

I lowered my head as I took several deep breaths before tearing the check up and throwing it at him like a handful of confetti.

“Fuck you and your money,” I whispered.

I spun on my heels and stormed out of the office. I hated him. I had been good enough for five minutes of pleasure, but not good enough for anything else. Well, fuck him! I would make it on my own. Fucking dick!

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