I was thinking with my dick when I hired Billy. I didn't need a personal assistant, but work made me get one. I only went into the office two days a week for meetings, so I figured I'd hire some warm body getting ready to retire and be done with it. When I asked my boss what my assistant would be doing when I wasn't in office, he looked at me dumbfounded.
"He'll be working out of your home too." He had answered as if it was obvious. I cursed silently. When I was home I wore just a robe. I only put on a shirt and tie when I had to do a video conference, and even then I was naked from the waist down. You saved time on doing laundry if you didn't have any to do.
I chiseled out a day to do interviews in the office. Every applicant made me sick. I wanted a warm body who would field a few phone calls, make a decent cup of coffee and stay out of my way. The people I got were young go getters that wanted to hop skip and jump up the corporate ladder.
Billy was the last person I interviewed. His boyish baby face and gaunt body caused my cock to twitch. He was fresh out of technical school, with just fast food experience on his resume. There was something about him though. Maybe it was his shaggy blond hair or naive blue eyes, but I decided before I even asked him a question that he had the job.
He was a nervous wreck during the interview. His clothes were too big, his voice cracked and he couldn't meet my eyes when he spoke to me. The boy needed guidance, guidance that I was all too willing to give. I even tested him by sending to fetch me a bottled water during the interview. He didn't question me about it. He just did it.
"You're hired." I surprised him when he returned. "I'll have HR contact you about your paperwork, and here," I scribbled my address on a slip of paper, "this is my address. This is where we're going to be working most of the time." He took the paper with shaky hands. "Come by after you get your paperwork done tomorrow."
"I don't know what to say." He stared down at the paper in disbelief. "Thank you so much for this opportunity, sir." I chubbed a little when he called me sir. "I promise I won't let you down." I thought I saw his eyes watering. Even if he did fail or make a mistake, I was going to enjoy pushing and punishing him.
HR called about midmorning the next day to tell me Billy was on his way. I grumbled about having to put clothes on, but I couldn't be too aggressive at first. Boys like him are skittish. You have to lure them in with a bit of sugar. Then once you have them eating out of your hand, it wouldn't be long before they were eating your dick.
I pulled on one of my white form fitted tees. The shirt was so tight, it was practically see through. Every bulging muscle could be seen and my nipples punctuated the shirt obscenely. That with my snug khaki shorts were the perfect enticement. I was proven right when I opened the door for him half an hour later.
Billy stood there, slack jawed and eyes wide. His clothes we too big for him again. He looked like some kid dressing up in his daddy's clothes. It was almost cute. "Billy, you made it." I smiled as friendly as possible at him. "Come on in. I got you a key made so you can let yourself in from now on." It took him a moment to shake off the lust before he stepped in.
"Your house is so nice." Billy said stepping in and marveling at my humble home. I took pride in my home. I had worked long and hard to be able to afford a place like this and had it decorated in overstuffed chairs and tiled floors. "Do I need to take my shoes off or anything?" It was obvious he wasn't used to such niceness.
"No, not at all, unless you want to." I shut the door and looked at my future fuck toy. "We will have to talk about the way you dress here." I heard him gulp audibly when I stepped closer to him. I smiled when I saw him shudder in anticipation when I reached up and loosened his tie. "We're not so formal here. You can wear anything or nothing at all. Just keep two white dress shirts and a red tie here for video conferences."
"Really?" I saw his eyes roll back in his head when my fingers brushed over his cheeks. I had him hooked, I just had to reel him in slowly. "That's a relief, I really only have a couple of dress shirts and slacks." I unbuttoned his top button, then one more for good measure. His voice cracked nervously. "I promise I won't abuse the privilege."
I patted his face amused. He would be begging me for the privilege to be used soon enough. The best part was the company was going to be paying him for it. "The nights you work late I'd prefer you stay in my spare bedroom." I put my arm over his shoulder and guided him further into the house. It was then I realized he was half my height. He was fun sized. "So if you'll let your girlfriend or boyfriend know so there's no problems."
"I'm single." He choked out. He was rigid against my body. I would have to ease him in. I did notice he did not clarify his sexuality. Of course by the way he was eye fucking me, I knew loved to swing from a dick. "I just graduated college and I'm still living at home with my parents."
"I had to do the same thing." I lied when I heard the embarrassment in his voice. He relaxed and I knew I had him hook, line and sinker. I kept my arm around him as I showed him the house, my bedroom included. I had to get him comfortable with me and my home before I made any big moves.
It was going to take time, but I was willing to wait. My balls would turn blue, but good things come to those who wait. The covert glance I gave his cute little tush told me that was a good thing. I just had to control myself and follow my plan. It wouldn't be long before he'd be smiling around a mouth full of my cock.
Of course I put him to work, answering phones, filing, running errands and some light housework. In the office the secretaries adored him, taking him under their wing. They knew I didn't want a secretary so having him doing odd chores and errands didn't phase them. They figured I was just keeping him busy so I wouldn't fire him.
When we were at my place, Billy let himself in, often catching me in just my robe. That was always planned. During the day, I would casually put my hand on the small of his back, eventually moving to the friendly pat on the butt. The first time I did it, he tried to hide the smile, but I saw it.
