The Assistant

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.

Once I knew he was comfortable with the touching, I decided to move forward. I had noticed his underwear peeking out of his pants several times. They were some bargain brand boxer briefs that didn't flatter his ass. I was going to remake him in the image I wanted. The first thing to change was his underwear.

He was bending over one day looking into a box or something when I put that plan into motion. I called him over. "Billy, come here." He stopped what he was doing and obeyed. I had subtlety trained him. He stood in front of me waiting for my next command. I grabbed him by the waist and turned him around.

Billy didn't say anything when I pulled the back of his loose pants, or when my middle finger slipped between his cheeks. I looked down the back of his pants at his deliciously smooth ass. "We need to get you some new underwear." I reluctantly let go of his pants and spun him around again. "I can't stand seeing these peeking out your pants. What size do you wear? Small?"

He flushed red with embarrassment. I gave him a friendly reassuring smile. "I'll order some that I think will suit you better." I pulled him into a friendly hug. I loved the feel of his body against mine. "It's my treat." I had to get one more feel of his plump little butt before I let him go. "Consider it a thank you for all your hard work."

I already had the underwear I wanted him to wear tucked away in my closet. Everything was lining up perfectly. The next day I told Billy I needed him to work late on Friday. This was the first time I had him working late. There was an extra pep in his step that Friday and my cock kept twitching every time I saw him.

We ordered out for dinner and finished the fake work I told him we had. It was time to reel him in. "Guess what, Billy?" We were sitting on the couch and I put my arm over his shoulders and pulled him close. "Those underwear I ordered for you came in yesterday. I forgot to tell you. Why don't you model them for me after we shower and we can decide which is best?"

The way he bit his lower lip was adorable. "I don't know." He eked out. "I'm a little shy about my body." He cast his eyes downward. "I'm scrawny. I'm not built like you." I was picturing him in the shower with me, and then wiggling his cute bottom at me in his sexy new underwear. I lifted his head so he I could look him in the eyes. That was all it took to convince him. "Okay." Came his sheepish response.

I gave his shoulder an encouraging squeeze. "It's just us guys here, no judgement." His lips curled up in a small smile. I knew he'd do it. If I asked, he did it. I had condition him to enjoy pleasing me. "Go on." I could see the nervousness in his stance so I gave him a playful swat. "There's an extra robe in the bathroom. Just put that on and then we'll go through the underwear."

We headed to shower, separately, unfortunately. Neither of us would have minded joining each other in the shower, but I had worked hard on this sexual meal to accidently scare him away. I was going to enjoy the garnish and all the trimmings. I wanted to enjoy the presentation and savor the flavor.

I showered quickly, wanting to be there waiting when Billy came out. I wrapped my robe around my naked body. I wanted him to see my broad hairy chest peeking through and wonder what laid underneath and then be pleasantly surprised when he found out. I grabbed the packages of underwear and went to eagerly wait for my delectable morsel.

I had to control myself when he came in wearing the robe I picked out for him. The robe was a black silk kimono robe that stopped mid-thigh and popped against his smooth white skin. I let out a low whistle and he actually blushed. "What should I try on first?" I knew my grin was salacious.

I handed him a package of boxer briefs. I decided to go tame to sexy. That way I got a taste for everything. He came out a few minutes later clutching the robe around him. "I don't..." The look I gave him cut him off. "Okay." He undid the robe, letting it fall open revealing my prize. He crossed his left arm across his body to rub at the right arm. He was trying to hide his body.

When he saw the look I gave him, he dropped his arm and came to me: I pushed the robe off his shoulders. It fell down around him, revealing his smooth creamy white skin. His body shook with shame and embarrassment of his body. "These look good on you." I put my hands on his waist and spun him around.

I was glad I had started with the tame first. I wouldn't have been able to control myself had I not. Billy filled those trunks to the brim. What he lacked in height he obviously made up in cock and ass. The temptation to take him was almost uncontrollable. "These, these are keepers." I patted his bottom and handed him the thong.

"Humor me." I said when he looked at the package then back at me. "Would I steer you wrong?" The only place I wanted to steer him to was to my dick. He shrugged then went back to change. I grabbed his robe he had left on the floor and used it to cover my growing excitement. Damn, that boy got my loins stirring.

He came back out, a little more confident, but still nervous. From what I could see, he had nothing to be nervous about. The purple triangular pouch was brimming with man meat. When he stepped closer I made a swirling motion with my finger. He paused, biting his lower lip before commenting as he turned, "I don't know about these."

I pushed down on my fully erect cock, trying to hide the tent from Billy. "I like how the front fits." He turned again, hiding those glorious creamy melons from me. "The back leaves something to be desired." He stepped between my legs. "What do you think? I mean, I could get used to having something up my butt."

I hated to be the one to tell him he was, very soon in fact. I reached up, running my finger along the waist band. He turned without being told. There they were. Two perfectly tasty mounds with a strip of purple between them. "I think you should get used to something up your butt." I couldn't resist, I ran my hands over his smooth cheeks. "You don't want to limit yourself."

I saw his cheeks, the ones on his face, were flushed when I sent him back to try on the next pair, a black G-string. This time he came out a little more confident in himself, spinning around this time without being told. How I wanted to pull that string aside and dive right, but I had one more appetizer before my meal and dessert.

He walked right in, not turning as before. The red jock he wore looked like it was just big enough to contain his manhood. He stopped between my legs, as before, a little uneasy. "Aren't these for working out and stuff?" I ignored his question, turning him to see glorious prize. "I mean do guys wear these as underwear?"

"They do." I turned him, bringing him closer to me, my face just a hair's breadth from his slender body. "If you prefer to have something up your butt," I grabbed the straps and slid them between his cheeks, "that can be arranged." I rubbed my face "accidentally" across his skin, the day's stubble scratching his skin. "You like things up there, don't you, Billy?"

He didn't answer. He didn't need too. I knew the answer. I let go of the straps, leaving them tucked between his cheeks. My hand moved in appreciative circles over his exposed skin. "You know there are some hidden benefits of being my assistant." I pulled his robe off my lap while guiding him to sit on my knee.

His eyes were a menagerie of conflicting emotions. There were filled with fear and hope. Of what I was about to do and fear that I wouldn't. His body vibrated with anticipation. I ran a soothing hand down his spine. I watched his eyes roll back in his head. I knew he wanted it, but I needed to hear him say it, needed him to admit it openly.

I knew he could feel me under him. All that separated his boy butt from my thick hard seven inches is my white terry cloth robe. "Do you like things up your butt?" I ran my stubble chin over his soft skin. He nodded yes. "Do you want to enjoy the fringe benefits of being my assistant?" My mouth was near his ear, my lips brushing his lobes. He nodded again. "Say it." I command in a soft whisper. "Say it and you can have it."

He needed that little nudge. He looked at me, his resolve melting away. "I like things up my butt." He finally said. He relaxed when he saw the wolfish grin on my face. "I like things up my butt, and I want to enjoy the fringe benefits." A bashful smile crept across his face. "I was hoping for some fringe benefits ever since you hired me."

"Oh, I know." I ran my hand over the pouch of his jock, feeling if full of his excitement. "I think it's time we both started enjoying those fringe benefits." I took his earlobe between my teeth, nibbling on it gently. "I hope you like the new underwear, it's your new work uniform when you're here." I nuzzled his neck, letting my whiskers brush against him. "You're also going to be working late a lot from now on."

"I'll put in all the overtime that is needed, Mr. Johnson." He moaned in my arms. "I want to do the best job I can for your, Mr. Johnson." My cock pulsed every time he moaned my name. He turned in my lap, our lips brushing each other. "Mr. Johnson, I think I'm ready to take on bigger responsibilities."

I let out a throaty growl before crushing my mouth against his. He straddled my lap, the cloth of my robe falling from my legs. My cock pressed up against his taint. The whimper of need he let out fueled my desire. He rocked back and forth on my lap, my hand guiding him along the length of my cock.

I kept one hand on his ass, the other reaching up into is shaggy blond hair. I took a fist full of his hair and pulled his head back, exposing his neck. I sucked on the sweet tender skin, feeling the vibration of his throat as he moaned in pleasure. I moved down his body, leaving his skin raw and rough with whisker burn.

I took his nipple between my teeth, eliciting a gasp from the pleasurable pain I gave him. I pulled the straps of his jock from between his cheeks and replaced them with my finger. I petted his eager hole. Billy's hole was warm against my finger and wet to my touch. If I pressed just a little, I knew I could slip my finger in.

Billy pulled at my robes, eager to get me naked. Every time he moaned my name, I got even more excited, taking it out on his supple body. My cock cried out for attention. It was so close to its goal, sliding under Billy, leaving a wet trail of slick along his taint. I needed to be in him, needed to have him impaled on my cock.

I rolled him over onto the couch, leaving him lying on his back. I stood, My robe fell open, framing my muscled hard body and thick veiny cock. I tossed my robe to the side, leaving me naked and ready. Billy ran his tongue along his lips. My cock was going to look so good sliding between his lips.

I sat back down on the couch, with one leg on the floor the other along the back of the sofa. I took my cock in one hand, waving it at Billy. "Come and get it, boy." Came my deep and rumbly command. "Time for you to put in some overtime." Billy turned over, and crawled towards my dripping cock. "There's a special project here that needs your attention."

He smiled at my play on words. Before he could take my cock in his mouth I grabbed him by his hair, held him still above my cock. I began rubbing the tip over his lips, over and over till they were coated with my sticky goodness. He did not try to go any further than I allowed like the good little worker he was.

When I released him, I felt his warm mouth surround my cock head. He nursed the tip, his tongue circling my thick head. He looked up at me, my cock between his lips. He was asking for reassurance. I smiled and stroked his head. "You're doing good. Now take some more." I gently pressed down on his head.

I let him set his own pace, trying to gauge his experience. "That's it," I used my most soothing voice, "take me down that sexy throat." I felt the press against the back of his throat, trying to get me past that infamous gag reflex. He coughed and sputtered around my cock and pulled back before trying to take me back down. "Take what you can, baby boy. You'll get there in time."

He ran his tongue along the underside of my cock as he worked what he could. His pert white bottom was arched up, looking scrumptious. I wanted to be buried balls deep in that ass, but the feel of his lips around my cock was just too good. I let him work me, stretching his lips around my cock. After a while I knew his jaw was aching by now, but like the perfect assistant he was, he wasn't going to stop till the job was done.

I moved up, pulling my cock from his hungry mouth. He looked up at me waiting for his next order, his mouth wet with saliva and precum. What I said came out an unintelligible snarl as I flipped him onto his back and held his legs up, pushing them forward to reveal that perfect pucker.

I held his ankles with one hand, stroked my cock with the other. I leaned down, spat on his quivering hole. "Fuck me, please, Mr. Johnson." I looked at his face to see he was deep in the throes of lust. I moved my hand from my cock to his hole, pressing my thumb against him. "Please." Billy begged again.

I wasn't going to deny him, or rather, deny myself. There was something I had to do first, something I had been longing to do. "You'll get that perk when I'm ready to give it to you, boy." I spat on his hole again, heard him moan as I pressed the spit into him. "Right now, there are other things on the agenda."