Affairs Assistant Ch. 01

It was the summer before my senior year of highschool, just days after my eighteenth birthday. My friends were out sunbathing near the springs or having sleepy sex in a tent during the early morning of a camping trip.

Meanwhile, I was sitting nervously in my car, stalling for time by applying another layer of lipstick with my rearview mirror. I was wearing my most uncomfortable shoes and my hair was curled meticulously, falling over one of my shoulders. I must have looked stupid sitting in my parked car in the long driveway in front of the country house, but I allowed myself until exactly five minutes before my interview time before I got out.

When the dreaded numbers finally appeared on my dashboard clock, I got out of the car and carefully picked my way up to the front porch, praying that my stilettos would not betray my balance. I rang the doorbell and felt an overwhelming urge to turn around and bolt back to my car.

I couldn't tell if the feeling was instinct or irrationality. Before I could decide, one of the tall french doors swung open. A beautiful girl my age stood in front of me now, smiling with glossed lips and perfect teeth. "Hi!" she said in a friendly voice.

"Hey-" I started, even more nervous at the sight of her. "Is this the right place? I'm here for a job interview, I saw an ad on Craigslist."

"Yes!" she exclaimed. "That's my dad."

I had no idea what to say so I just nodded, feeling my head bob awkwardly up and down for a little too long. The girl giggled and made a gesture at the foyer behind her, welcoming me into the house. I stepped over the threshold, trying my best not to trip while doing so. My body felt like it was about to fall forward at any second due to the height of my heels.

"Nice house," I said plainly.

The house was actually incredibly ornate. Where a country home would hang rustic signs of roosters on metal buckets, this home hung fine art in heavy wood frames. The stairs of the home were marble and spiraled three stories above our heads. A domed skylight bled white sun down into the foyer, soaking into the the cherry red wood floors. I could catch a glimpse of more stylish rooms beyond the foyer and my curiosity was piqued since this would be my new place of work if I was hired.

"We just moved here," the girl said. "My dad's business has been really big lately."

"Do you live here too?" I asked her, trying hard to formulate a sentence that sounded normal and didn't showcase my nerves.

She raised her brows while smiling. "Yeah."

"Ah," I responded, spiraling into another nodding session.

"Oh, I'm Lynnae by the way," she said. She was holding onto one of the spindles of the staircase in either hand, displaying her slender body to me. She was barefoot, wearing short-shorts and a too-small t-shirt. Her pink phone case was sticking out of her back pocket. She was looking at me with happy but intense eyes. "My dad's name is Robb Sterne."

"Oh," I said, trying to look away from her body.

A tall older man with a salt and pepper beard appeared in the hallway to our left. "That will be all, Lynnae," the man said. Lynnae giggled and ascended the stairs, her bare feet slapping against the marble. The man removed his reading glasses and folded them, placing them in the breast pocket of his dress shirt. "Are you responding to the ad?" he asked.

"Hi Mr. Sterne, I'm Jamie Hopkins," I said, carefully walking toward him with my hand extended for a shake.

"Jamie," he repeated. "Lovely name for a lovely girl." To my surprise, he took my hand, turned it and planted a kiss on the back of my fingers. The soft tufts of his beard and mustache surrounded the warm sensation of his lips in a surprisingly pleasant way. I didn't have any time to voice my confusion however, because Robb said, "This way," and walked back into the hallway.

I followed, anxiety once against shooting through my body. I didn't feel like running was an option any more. We have already been introduced after all, I thought.

We entered a large office decorated in deep navy blues and accented with white. I sat in a wingback chair in front of the desk that was covered in files and sheets of paper. "I've just been so busy," Robb said shuffling the papers together rapidly. "No time for anything personal." He looked up and gave me a charming smile as if I was in on some kind of joke.

I smiled back and watched him as his hands moved deftly through the stacks. I guessed his age to be late fifties. Despite this, his hair was a thick plumage of white and grey hair on his head that current released a single curl over his creased forehead. His eyebrows were thick over almond shaped dark eyes. His muscular arms were also covered in dark hair. I stared at his forearms, where his rolled up sleeves met his skin and I could feel myself start to blush. I had no idea that someone of his age could still look so...good.

After a few more seconds of organization, he sat in a wingback chair of his own. He laced his fingers together over his trim stomach, looking over me with a sigh. Then he asked, "So. What made you respond to the ad?"

"Ah," I felt completely lost. The unexpectedly handsome face across the desk seemed to drain all my answers out of my mind. "My parents made it clear that I'm no longer welcome in the house after graduation," I began.

Robb held his hand up. "College?" he asked.

"Highschool," I corrected.

"But you're still," he paused. "Of age to work?"

"Uh, yes," I said dumbly. I thought the age to work was fourteen in this state?, I thought to myself. Robb seemed satisfied with my answer and sat back again. "Sorry to interrupt."

"It's okay," I said, searching my mind for what I was saying. "Um, so, yeah, I'll need a car and a place to live by next spring, so that's why I'm applying."

Robb gave me a steady smile. "What makes you fit the job position?" he asked.

My rehearsed answers finally came back to me. "I'm a hard-worker and I like to learn new things," I said with a smile.

"Good," Robb said. "Any experience?"

"Yes," I said, lying.

"Good. And whom did you work for?"

"My brother," I lied again.

"Really?" he said, leaning forward. "And you...liked it?"

"Yeah," I said, attempting a probable story. "I was reluctant at first but I knew I didn't have a choice," I feigned a laugh. "He ended up being the best to learn from."

"Wow, Jamie," Robb said with a wicked smile. "I think I like you already."

I felt my stomach turn over at his words. Again, the impulse to escape came over me but I let it pass. Robb picked up a pen from his desk and brushed it against his lips, studying me for an extended moment. I could hear the grandfather clock ticking in the corner. I looked down to avoid his stare.

"May I see you without the top?" he asked.

I was confused. Does he mean the top layer of my hair? I thought. I brushed some of my hair from my shoulder, letting my curls hang down my back rather than down my front. I looked at him for clarification.

"Without the blouse," he said in a soft, calm voice.

I felt my heart drop in my chest. "Why?" I asked, quietly.

He didn't break eye contact with me. The pen in his hand clicked once. "Just want to see the body I'm hiring. Also, all office clothing needs to be completely up to standard," he stated.

I felt speechless. I knew that this happened to girls occasionally, but I didn't expect it on my first ever job interview, especially not with someone as charming as this man. I didn't want to foil the chance of getting the job. It was evident that he could give me a respectable wage.

Instead of arguing, I got to my feet.

I untucked my long-sleeved white blouse from my pencil skirt and unbuttoned by blouse from bottom to top. When the buttons were undone, I let the fabric fall off of my shoulders and slide down my arms behind me, collecting at both wrists.

I stood there exposed, realizing with a somewhat frantic thought that this was the first time anyone had seen me in just a bra.

Robb stared at me with an expression I had never seen on someone's face before. It was of hunger and restraint, softened at the edges with obvious admiration. He kept his hand near his mouth. His eyes traced the edge of my body, looking back and forth between my breasts and my face.

"Skirt?" he said after a long silence.

I paused but then slid the zipper on the side of my hip downward. My skirt fell into a black circle around my feet. Robb again took in the sight of me over the space of several seconds. His eyes fixed on my legs and clicked his pen loudly. "You will need to get a garter," he muttered.

"What's that?" I asked, half wanting him to define what a garter was and half wanting him to repeat himself.

He raised his chin at my direction. "One of your thigh-highs is slipping and the other one is folding outward. Get a garter."

"Okay," I said, my throat feeling dry with his tone change.

"Walk over here," Robb said, gesturing with his head to his left.

I did as he asked.

He turned his chair to face me. I could almost feel the heated energy coming from his gaze. It tingled over my bare skin. I watched his fingers twitched when he saw my stilettos. "Good shoes," he said. "Turn."

I did as he said, once again. With my back to him, a shiver went down my body. Was I doing the right thing? I tried to get a glimpse out of the window, hoping no one could see what I was doing. Suddenly, I felt Robb's finger touch the skin on my upper back. I jumped in fright and turned back around. "What are you doing?" I asked, my voice trembling.

His face grew grim. "Turn, please," he muttered.

"Why?" I managed.

His eyes bore into mine. "So that I, as an employer, can assess you as a potential employee. Now either turn around right now or leave," he stated in the low voice.

I attempted to slow my breathing and turned back around to appease him. As I turned, I craned my head to look down the hall, hoping that Lynnae could see me topless and catch her father being so inappropriate.

Robb's finger touched the skin on my upper back again, and then, as if by magic, my strapless bra was loosened from my body and fell away in Robb's hand. I wanted to cover my bare breasts with my forearms, but I didn't dare.

I had a feeling that Robb had taken it off for me on purpose.

Robb made a walking motion with two fingers on my arm, indicating silently for me to turn back to face him. When I did so, I was startled to find his face mere inches from my body. My nipples were standing up, both from fear and the sudden chill.

Robb remained seated at waist height, looking at my breasts that hung above him. I couldn't help but notice how close his mouth was. The image of him sucking on my breasts as if he was a child floated into my head and I pushed it away.

Robb tilted his head from side to side, inspecting my ribcage. He clicked his pen loudly again. "Red marks on the skin," he muttered. "You need a better fitting brassiere."

"Yes," I said, embarrassment washing over me.

Robb reached out and brushed his finger to my inner thigh, touching the nylon fabric of my stockings.

I let out a soft gasp.

"Hmm." was his only response.

Then he leaned forward. With both hands, he pulled down my panties.

This had officially gone too far.

I clenched my legs together with all my strength. Meanwhile, Robb flattened his left hand sideways and attempted to force it between my legs. I pushed my thighs together harder as he persisted. I glanced toward the door, wondering if I should shout for Lynnae.

Robb grunted, trying to use his strength to open my legs and expose my pussy to him. I shook my head a few curls coming loose around my face as I looked down at his hand.

Realizing how intensely I was resisting, he threw the pen on the desk and grabbed me. He moved my body and turned me ninety degrees so that I was now facing the back wall of the office and my ass was pressing uncomfortably against the desk. His hand continued to force its way between my legs. I kept them closed, struggling. He then lifted me, making my body slide into a half-seated position on the desk. He pushed his broad shoulder into me, making me lean back slightly. My legs now naturally parted despite my efforts to clamp them shut.

Robb forced his flattened hand upward into the slit of my pussy. I now straddled his flatted hand against my will, feeling my warmth and wetness against his firm fingers.

Robb groaned quietly at the feeling while I gasped in shock.

"Good," he said.

I wanted to push away his muscle-bound body but my hands were trapped in the sleeves of my blouse. In order to free them, I would either have to put my shirt back on over my shoulders, or slide my arms out. This was impossible because the sleeves were still buttoned in what could be considered a makeshift restraint.

He kept his hand firmly against my soft inner labia. He made no attempt to rub me perversely, nor did his fingers try to penetrate me. His hand remained firmly between the folds of my pussy, trapping me in place.

"Do you masturbate?" he asked quickly.

"Yes," I responded in a breath. I wasn't sure if this was the right answer or not.

He asked another question. "Did your brother make you fuck other people for him while he watched or videotaped you?"

"Wh-" I stopped, not sure what to say. I was utterly confused.

Robb suddenly pushed his hand upward again, making me gasp. The knuckle of his flattened thumb had found my clit. The sensation of his skin pressing into me sent a burst of pleasure through my lower body. The early beginnings of an orgasm curled through me like smoke. I moaned and moved my hips. He responded by shoving his hand upward once again. Another burst of pleasure hit me and I could feel his hand becoming wetter as I remained straddled there.

"Tell me," he whispered raspily in my ear.

"Yes," I moaned.

"Did you like it when your brother watched?" he asked, his lips against my ear.

"Yes," I repeated. My hips moved again.

"Stop squirming," he muttered, annoyed. "Do you like to fuck other girls?"

I was stunned but my mind travelled back to Lynnae, his daughter. I thought about the tantalizing inch of tanned skin between her shirt and shorts.

Robb's hand shoved upward again, making me whimper. "Yes," I whispered.

His other hand made itself known, touching my upper left thigh. I gasped, wondering what he was about to do. "And you're ready to do all this for me?" he asked.

"Yes," I said back.

He grabbed my thigh-high and yanked it away from my body, creating a tear that ran all the way down to my knee. At this, my body instinctively jerked away out of fear. Robb took his thumb out from my slit and then pressed it firmly into the soft tuft of hair between my legs.

He controlled my entire body with this grip. His other four fingers tilted up slightly as a result, as if he was going to start penetrating me. I groaned and my knees lifted without me thinking about it.

"Get better stockings," Robb whispered.

He released me.

My feet landed back on the soft rug of the office and Robb didn't look at me again. Instead, he reached into his desk drawer for a card, handed it to me, said "Keep your phone on," and left. I remained standing in the office almost completely naked.

I got back to my car after messily redressing and running out of the house and I opened the folded Craigslist ad I stowed in the glovebox. I read it with new eyes.

"Affairs Assistant needed.

Older gentleman seeking assistant. Applicant must be willing to tend to my personal, business, and sometimes family relationships. Assistant will need to have skills to please each accordingly. Work schedule and location may vary, but main services will be performed at my estate. Do dress in complete business attire for review. Pay per service and per client will be offered."