Affairs Assistant Ch. 02

The summer of my eighteenth birthday was also the summer before senior year.

I was the only young senior that I knew of to have a job that poured thousands of dollars into my checking account over the course of a single month. I was newly hired as an Affairs Assistant. But I had discovered in the middle of my interview that my boss intended to hire me to preform illicit acts on his behalf.

My boss, Robb Sterne, was an extremely handsome older man, with thick salt and pepper hair and muscular forearms. When I closed my eyes at night I could still feel his firm hand between my legs, touching my virgin pussy with a strength that made me wet, even when surrounded by family or sitting in church.

The only instruction I had received from Robb came in the form of short texts or emails. There would also be brief messages attached to the money being transferred into my bank account. Often times, I would be hanging out with my friends beside the pool and see a message pop up along with a deposit of hundreds of dollars. The message would read something like "Brazilian wax and nails" and then an address to a high end spa.

On this day, I received a brief email from Robb.

Jamie,

Arrive at my estate tomorrow afternoon. Photography session before your first client. Please arrive clean and no red lines from underwear on body.

Thanks,

R.S.

I felt a shot of nerves, wondering what exactly my first client would want with me. I would have bitten my nails had they not been plastered with acrylic extensions.

I drove to Robb's country house the next day, half-hoping that his daughter Lynnae would be there too. She was my age, beautiful, and seemed interested in me the last time I had seen her.

I was disappointed to see my boss opening the door after I knocked. He was dressed in a grey vest and a blue dress shirt rolled at the sleeves. The curl of thick salt and pepper hair hung on his forehead and his face did not betray any emotion. "Good of you to come so early," he said as I stepped inside.

I was surprised to see him sink to a crouch in front of me once the door closed. He reached up and lifted my loose, lacy tank top to stare at my breasts. He turned his head to either side. "No red marks. Good," he remarked. He let go of my top and then unbuttoned my shorts, slipping them down. I touched my bare skin underneath. "Next time, don't wear jean shorts. The heavy material can leave marks. Very important for your skin to be smooth for this job. Understood?" he asked, looking grimly up at my face.

I nodded, nervous that he would force his hand against my bare pussy. Instead he pulled my shorts all the way down and I stepped out of them. He left them on the cherry wood floor and reached up to run his hands up and down my newly waxed legs, his fingertips coming close to my inner thighs each time. His hands then brushed over my ankles and he touched my high heeled sandals. He undid the straps and I stepped out of them as well. "Good shoes," he said approvingly.

"Thank you," I said mousily. I could not shake the nervousness he made me feel. I tried my best to keep my head clear and think about the money I would surely receive after the photos.

I followed Mr. Sterne up the stairs wearing just my lacy crop top, my bare feet feeling pleasantly cooled by the marble.

We mounted the second floor and Mr. Stern lead me into a large bedroom. To my surprise, there was no furniture in the room and the curtains were closed. There were about ten or twelve clothing racks holding a hundred or more dresses. Some were sparkling cocktail dresses, some cotton summer dresses, evening gowns, prom dresses...the room overwhelmed me with colors and fabrics.

Robb disappeared through a narrow passage between two of the racks. I soon heard him scraping the hangers as he searched through the clothing.

"What is this room?" I asked, realizing the dress nearest me was this season's Chanel.

"Lynnae's closet," I heard him respond. "I buy her a new one for the weekend."

"Every weekend?" I asked, incredulous.

He reappeared holding a few different dresses and nodded, his thick eyebrows maintaining his mask of emotionlessness. "She won't mind if you borrow."

I followed him to another large bedroom on the same floor. This one was decorated as if a small girl slept there. The bed was frilly, the pillows were pink, the curtains were sheer. On a white vanity there was a three-monitored computer with a large webcam attached.

Mr. Sterne lay the dresses over the back of the white chaise in front of the computer and then took my crop top off gently. I felt embarrassed, my erect nipples gave away the arousal he made me feel. My pussy was starting to feel warm between my legs but no wetness came.

"These photos will be used for those clients which ask to see you naked. They expect the highest quality from my assistant so you are never to use your own photos. Do you understand?" he asked.

I nodded.

He unzipped a camera bag that was sitting on the desk on the other side of the room and unpacked camera equipment. Once lighting was turned on and the camera's tripod was placed delicately in front of the bed, Mr. Sterne gestured to the frilly bedspread with his index fingers.

I climbed up and his instructions came immediately. "Cover your breasts with your hands and close your legs."

I did so and the shutter clicked.

"Open your mouth and show me your tongue." Click.

"Turn around and point your ass at me but keep your hand over your pussy." Click.

"Show me a good arch in your back." Click.

"Stand up and try to hide your body from me." Click.

"Hold your arms out to the side and lean on your hip, show me that young body." Click.

"Get on your knees and show me the face of a slutty high school girl who wants to taste my cum."

My heart began to beat frantically but I did what he said. Click.

"Show me a little scared girl," he said. Click.

"Show me a girl who like to show her daddy her privates." Click. At this point he stopped and looked down to review the photos. With him distracted, I slid my fingers against my pussy and rubbed my clit. I peered over at my boss, trying to see if he was hard through his trousers.

He noticed me staring and looked back up.

My hand continued to move against my pussy and I touched my breast with the other hand, showing him how good it would feel if he were to be the one touching me there.

He didn't respond and instead raised the camera and took picture after picture.

"What is it, daddy?" I asked, in a girlish voice.

"Don't," he reprimanded.

I immediately felt embarrassed and took my hands from between my legs.

Robb reached over and threw me one of the dresses that he had brought in. When I slipped it on, I realized it was way too short and seemed to be made for a six year old rather than a woman. It covered my breasts and stomach but I was exposed from the hips down.

"Lay on your back and keep your legs closed, like you're hiding from me," he instructed. I did as he said, looking up at his handsome bearded face. I wondered what he was thinking. Who he was trying to make me. I wondered if he picked me because he wanted to fuck me or he saw me as someone his friends would like.

"Smile at me," he instructed. Click.

He leaned over and pushed the fabric of the dress up to my shoulders, exposing my breasts again. He took several pictures standing between my legs and looking down on me. "Look at me like you want me," he said.

I didn't change my expression. Click.

"I'm going to fuck you hard up the ass," he said with a sudden forcefulness. Click. My face had definitely shifted expression, this time into fear.

"Good," he remarked. Click.

"Hold your tits. Can you lick your own nipples?" he asked. I could, and I did. Click. Click. Click.

I stared down at his trousers and could see a faint shape hanging on his upper thigh but it was not the familiar hardened sight I had been seeing on guys since middle school. He was looking down at his camera again. "These are good," he said quietly.

"Is this one of Lynnae's dresses too?" I asked, touching the too-tight fabric over my shoulder.

He looked over and nodded. "One of the first I got her."

My heart skipped a beat. "She didn't want to be your assistant?" I asked, feeling myself prodding when I knew I shouldn't.

His eyes landed on me with intensity and I tried to keep a cool face. "I've never asked," he replied, shortly. He handed me another child sized dress and I put it on. He told me to stand on the bed and do twirls while he photographed under the fabric at my naked body. "Good," he said.

I held the skirt away from me, pretending to flash him. Click.

"Pretty girl," Robb muttered.

I turned and bent over. Click. "Fucking pretty."

I sat facing him and opened my legs, smiling shyly. Click. "Oh yeah, Lynnae, that's it right there," Robb whispered to himself.

My hand shot down to my pussy and began to rub myself again. "You like that?" he asked. Click. Click.

I sat up and pushed my breasts together facing him. "Show me your privates, like that, like that," he muttered. His dick was finally hard and I slid my hips toward the end of the bed with my legs folded underneath me, my pussy opened.

Robb dropped to his knees for a second time in front of me and took pictures of my open legs. "A perfect bare slit," he whispered. "So wet from showing off." He looked up at my face. "Take your fingers and spread yourself open."

I reached down with my index and middle finger and parted the lips of my pussy, hearing my own wetness between my fingers as I did so. Click. Click. Click.

My boss reached down and pulled at the hard shape in his pants and I moved my hips closer.

He stood up and backed away, looking at the photos again. "Good." His phone dinged and he looked at the message that had appeared. "It's my business partner from the law firm," he said, looking up at me. "He wants to use a chat room to sext you."

"Right now?" I asked, my pussy pulsing with pent up energy. I desperately wanted to lay back and give myself an orgasm.

"Right now," he responded. "Go sit at the computer and we'll get started."

To Be Continued