Claire and Her Boss

My name is Michael, I’m 52 and have worked as a manager in a contracting company almost my entire adult life. Like many young bucks in the trades I was initially pretty dumb, I married young and had a kid at 25 and then again, accidentally, at 32. By then I was well enough established, graduated from night school, and was moving up in the company. By 35 though my now ex-wife and I divorced, though pretty amicably by most standards. She remarried a few years later but I was done, it was the bachelor life for me. I focused on earning a lot of money (which I did), raising my children, and sleeping with younger women. It’s actually a pretty great life, but there’s only one girl worth writing about in all that time.

She wasn’t an obsession of mine or anything but I looked forward to seeing her if I knew we would cross paths. I first met her a few weeks after I hired her father, she was 16 at the time and already a target of male attention. Claire hadn’t really changed much since then, she was now a senior in high school and 18. She was about 5’6″ with a lean, tight little body. Maybe 100 pounds soaking wet but I doubt it. No more than a B-cup, taut stomach, very slender legs, an elfish-pointed nose with a few freckles on each cheek. She was toned and sexy… and she knew it. She had long brown hair down to the middle of her back and ice-blue eyes. But the thing I liked most of all was her ass. I was confident I could fit it into one palm. She was slender and her hips were also tiny… it all came together in the perfect, fuckable butt. Whenever she walked by in tight pants most straight men could be caught eyeing the subtle, muscled twitch of her ass, the sway of her hips, and the flirty nature of her stride.

My daughter was two-years ahead of her at school but both were on the dance team together, I had the pleasure of getting to watch Claire at events for a whole year before my daughter went off to college. Seeing Claire dance around in skin-tight black pants, cutoff tops… I had a tough time getting to sleep those nights. I could not get the thought of her sexy body out of my mind.

An opportunity to strike finally came in the spring of her senior year of high school. Our construction company was throwing an awards party and I was by then the VP, and the only guy who outranked me had been absent while golfing for several years… so it was up to me to host. Along with awards for sales, customer service, and all-around-great-guy we were giving Claire a $2,000 scholarship for college the following year. She was a great student, involved in athletics, all the boxes were checked. We figured it was a good morale booster and we usually gave it to local kids whose parents did not work for the company, so when I saw her name on the list I figured it would be worth just getting a free pass to stare at her like a piece of meat for an hour.

At the ceremony she arrived in a tight pair of grey slacks and a blue, silk, sleeveless blouse that showed off her toned, tan arms. As if I wasn’t already going to be drooling over her: she wore a matching pair of blue pumps that gave her legs and ass – if possible – an extra bounce.

After the awards presentation there was a little reception. Claire came up to me after I had knocked back a couple of whiskies and struck up a conversation. Now at 52 I was certainly no longer the specimen she was likely to be surrounded with at high school, but I had kept myself in reasonable shape and was 6’4″ so even with her heels I towered over her. As she looked up at me I became determined to find out what it would feel like to pin her small frame beneath me and rail her teen pussy with my cock. Or better yet, train those ice-blue eyes to look up at me while she sucked me off. Right as she said, “Hi, Mr. Peters,” I was lost in a daydream, imagining my powerful hand wrapped in her hair while she was on her knees servicing me, making sure to control her mouth and force her into submission.

“Hey, Claire!” I said, “Enjoying the reception?”

“I am, how ’bout you?”

I took another sip of what was now my third cocktail, and used that as an excuse to eye her up-and-down.

“Corporate awards party at 5:15?” I joked, “What’s not to like?”

She giggled a little and gave me a knowing look, “Not exactly a rager.” I agreed.

“So what’s on tap for you this summer, young lady?” She stiffened a little and set her own ginger ale on the table between us. She immediately became a little doe-eyed and shy, pivoting nervously on one heel.

“Well actually that’s what I wanted to talk to you about,” she said, “I’ve been having trouble finding a summer job and I need to save up for college next year.”

I nodded politely but underneath I couldn’t believe my luck. My admin assistant was out on maternity leave (and eventually ended up not coming back) I needed a temp for the summer and could not have dreamed up a better scenario. Still this was going to be my power-play so I kept my poker face on and let her sweat it.

“Yeah it can be tough to get a job for just a few months in this economy, I understand,” I said. She instantly became more nervous but I could see a bit of determination in her eyes. If I wasn’t mistaken she also became more flirtatious. Claire closed the distance between us so that it felt like her cute little face was right under mine. I honestly couldn’t tell if this girl would be inexperienced and sweet or an artisan fuck expert… she was mysterious enough. I frankly didn’t care which one she was, I wanted to completely own her in bed and make her bend to what I demanded of her hot, young body.

“Sooooo,” she continued, “I wanted to ask if maybe you knew of something I could do here over the summer? I was hoping…”

“Oh,” I pretended to act surprised, “Well this is a pretty experienced group, Claire. We really don’t hire anybody with less than a college degree. Unless you want to take that cute little physique to a worksite, I’m sure the guys would appreciate working with you.” This may have seemed a little creepy but I was making a play, I could turn her down initially while pointing out I thought she was attractive.

It seemed to work. She blushed and fluttered her eyes.

“Maybe a tryout?” she said hopefully, “I’m positive I could learn to do anything you ask of me…”

I sighed – trying to recall any skill for acting I may have had – and gave her an appraising look. I think it was her cleavage in the silk that convinced me, maybe it was her scent, or imagining her wearing those heels and nothing else.

“Listen,” I said sternly, “I do happen to need some help around the office for a few months. I can be very demanding though. If you’re not up to it, you’re gone. Do you understand?”

She immediately backed down a little, I could tell she would be fun to train both in the office and in the bedroom… she was energetic but submissive when put in her place.

“I understand,” she said, “I won’t let you down…”

***

Less than a month later Claire had graduated from high school and joined the company. She had proved to be a quick study and, as I suspected, garnered a lot of male attention. The 20-something women around the office were particularly jealous and cold shouldered her at every opportunity, but Claire charged on.

As for me I had her on a great leash, figuratively of course. On her first day she showed up in a loose fitting, to-the-floor cotton dress and flats. After getting her settled in I took her aside in my office and talked to her about my expectations for how she should dress.

“You’ve got a great body, Claire,” I said, “And as the visible head of this company, I need a presentable assistant greeting the clients that come to see me. So from now on skirts. If you want to wear a dress it has to be tighter and above the knees. Slacks are ok as long as they’re not too baggy. Jeans on Friday but I expect them to be fashionable as well, and heels everyday, no exceptions.”

She looked generally offended but cautious when that came out, “I just didn’t think you’d be watching me that closely.”

“Well as I said I can be very demanding,” I replied, “I do need someone in front of my office that clients and subordinates see as both professional and distracting. It helps me do my job when they’re thinking of what they want to do to you and not what they meant to say to me. You understand?”

She seemed to be flustered, complimented, and shy all at the same time.

“Well I’ll do what I can,” she said, standing to go. Claire started to walk out and then stopped and turned to face me, still sitting on my office couch. “Is there anything else I should know about what you’d like me to wear, sir?”

“Well first of all,” I said, “I do like that you call me sir. The only other thing I’d tell you is whatever you wear I don’t want to see a panty-line. They ruin the picture. Is that understood?”

“Yes, sir.”

From there on the trap was pretty much set, I just had to bide my time and let her get comfortable with what was inevitably going to happen to her. I pivoted from then on too, I stayed pretty professional, rarely making any comment that was even remotely suggestive or flirtatious.

She didn’t take the bait though until a few more weeks, and after two months of working toward my goal… and years of fantasizing about it… I was ready to burst. I had been “saving up” for Claire since the award reception to make sure the first of many planned orgasms really made a point. Then one Thursday she walked in wearing a relatively snug sundress, it was thin, floral-printed and ended just a few inches below her cute little ass. BUT she was not wearing heels, instead wearing a pair of all-white converse tennis shoes. The outfit accentuated her young physique, demeanor, and spunk but without heels it was a violation of the dress code I had laid out for her.

When she brought in my coffee at 8:15 and I surveyed her I knew it was time. She laid my cup of coffee next to me on my desk and I gave her an appraising look.

“Is there anything else you need this morning?” she asked. I looked uncomfortable and scratched my chin, still looking her over. She looked damn good, but rules were rules.

“Yes,” I answered, “Can you close the door.”

She stiffened immediately, I think she knew what we would be discussing. Claire walked over to the door and, if I wasn’t mistaken, was accentuating the sway of her hips to try to disarm me as she did. Cute.

The door closed and she turned around, the entire length of the office between us. I got up from my desk and stood to the side.

“Lock it,” if she seemed nervous before now she was positively apprehensive. She locked the door then closed some of the distance to me before I told her to sit in an arm chair in front of my desk. She did and I was certain she intentionally let her dress ride up her supple, yet firm thighs to show them off for me. She knew I was mad… I mean she didn’t know I was faking it… but still.

“Claire,” I started, moving across the corner of the desk to be standing in front of her while she sat, “on your first day I laid out expectations about how you were to dress.”

“I know I-” my hand went up to stop her.

“Do you really think tennis shoes,” I pointed to her feet, “are appropriate for this office or my expectations?”

“I know I was planning on a different outfit, sir,” she answered, “But my older sister is back from college and she borrowed the shoes I was planning on without telling me. These were the only things that even remotely worked with the dress.”

I looked perplexed, “So why not just skip the dress and wear something else?”

“I didn’t have anything else ready that I thought you’d like,” she answered, “And I bought this dress just for the office, for your rules… I thought you’d like it, sir.”

I looked her over. I did like it, it clung to her slim 18-year old body very nicely and I couldn’t see a panty line around her hips. The dress wrapped around the back of her neck rather than having shoulder straps and I really liked the sun-kissed shoulders it displayed, she had a sprinkling of freckles here and there that added to the innocent look she had.

“I do like it,” I said, “Stand up. Let me see.” She did as she was told, a good sign. “Closer,” I ordered. Claire took a step forward in her white converse and was now just a foot or so from me. Her eyes were down, staring at the floor, nervous and uncertain. I put a hand out and pulled some of the dress material right at her hips between my fingers. She took a deep breath, clearly not sure of what to do.

“It’s a nice dress, Claire,” I said, “but I told you what my expectations were. Do you remember?”

“Yes, sir,” she answered. When I remained silent she looked up at me, her eyes were terrified and possibly beginning to wet. I motioned for her to elaborate. “You wanted me to wear nicer clothes, sexy clothes, that distracted the clients. Heels everyday. No panties.” I cocked my head.

“I didn’t say no panties,” I was clearly amused, “I just said no panty line. They spoil the view.” She gulped a little bit.

“Oh,” she said softly, looking down again. I rubbed the side of her hip checking for material beneath the dress.

“Claire are you not wearing panties?” I asked. She shook her head.

“No, sir.” Blood started pouring into my cock, I was going to impale this little fucktoy in a matter of minutes. I wasn’t sure if she knew that yet though. I started pulling up her dress from the sides and exposed the very top of her legs. She reached for the hem of the dress and started pulling it back down, defensively. “Sir I -”

I stopped and put the sternest look I could muster on my face.

“I said I could be demanding,” I growled, “How many rules do you plan on breaking today? Or do you not want to keep this job…”

“No I -”

“Then take your hands off your dress.” She did. I stood up from being propped on the desk and motioned her forward a few steps. “Put your hands on the desk.” She bent over at a 45º angle and the sundress slid up to just below her aforementioned cute little ass. I stepped behind her and appraised the view. At 52 erections weren’t as easy to come by as they used to be but I was at full attention now, soon she would see what I had in store for her and I was honestly feeling sorry for her. I was always comfortable with my cock, at 8 inches I’d never heard any complaints and it looked to have the same girth as Claire’s forearm.

I got in close behind her and ran a hand up the side of her right leg, taking the dress material with it as I slid all the way up to her waist. For the first time her tiny, athletic, teen butt came into view and it was just perfect. Smooth, a little bubble, tight and now very vulnerable. I was correct that the whole thing could fit into one of my hands and as Claire had promised she was going commando.

“Well at least you obeyed this rule,” I remarked, “Above and beyond actually.”

She began to pivot to turn around as she spoke, “So can I go back to- ” I used my other hand to grab her left shoulder and then pin her all the way down to the desk. I stepped to her left and placed my right hand on her helpless little arse.

“You disobey the rules there are two options,” I said, holding her down strongly, “You leave or you take a punishment. Do you understand?”

“I do.”

Smack! I went pretty hard the first time. She gasped and recoiled.

“I do, sir,” I corrected her. I lifted up her dress so that it was wedged between her stomach and the desk, freeing my other hand but keeping her exposed. I let my right hand drift down between her legs and cup her petite teen pussy for the first time. I reached further to the front of her mound to discover she was completely smooth. Perfect.

“You shave your little pussy, Claire?” I asked, “That’s good.”

“I just started waxing, sir,” she answered. I let my thumb trail up and down her lips and then penetrated into the sweet spot. All I could think was: oh my god. She took a sharp breath as I violated her tiny box, her lips and pussy walls wrapped snuggly even onto just my thumb. I was feeling sorry for her but now I was downright worried for her, a healthy-sized prick of a much older man was going to really tear her apart. Just the thought of it made me that much harder.

I pulled my hand out and grabbed the curve of her ass, letting my fingers fall between her cheeks and explore the soft flesh within. Then, without warning I brought my hand back and swung forward with gusto to slap her tight ass for a second time. This time she bounced up onto her toes and I got to see her sexy legs flex and her whole body writhe. Her feet contorting inside those youthful white chucks added to the “innocence turn-on” I was soaking up.

“That was for not wearing heels,” I said. I then pulled her long brown hair into my left hand and yanked her head up to attention. “And this is for interrupting me twice.”

Smack! Smack! With her head at attention I could see her grit her teeth but now, after it was over she began to take a deep breath and relax a little more.

“And finally,” I said, whispering in her ear, “This is for stopping me when I wanted to pull your dress up.”

Smack! Her tongue went between her teeth just a little in response to the pain.

“I’m sorry, sir,” she said, with the hint of a sultry tone. I pulled a little harder on her hair and brought her to standing in front of me. She looked down and I snapped right in front of her young eyes, it felt like I was holding half of her weight in the hand pulling her hair and she was up on her toes to try to avoid some of the pull.

“You look at me when I’m talking, Claire,” I said after snapping. She complied… I knew it was going to be a good morning for me. I leaned in to whisper in her ear, still holding her hair vigorously. “Claire when’s the last time you had a cock in that pretty mouth of yours?”

She paused for a moment, I drew her scent in between her neck and shoulder.

“Last month, sir,” she replied.

“A boyfriend?” I asked. She shook her head.

“No sir,” she answered, “It was…. it was Mr. Stevens the vice principal.” I was surprised, I knew Jim Stevens well. He was a husky guy, probably mid-40’s, and seemed like a pretty mundane administrator. I leaned back up and looked at Claire.

“Summer love?” I joked. She gave a protesting, sarcastic little face.

“No he caught me and two other girls with marijuana in the parking lot, sir,” she started, “He made me give him head while the other two watched the door.” I chuckled a little.

“Good,” I said, “So you’re used to servicing older men who have some power over you, aren’t you?”

She shrugged her shoulders a little, “I guess so, sir.”

“Do you like having a cock in your mouth, Claire?” I asked, not really caring what the answer was.

“I don’t know, sir,” she answered, “I don’t think I’m that good at it.” I nodded, taking in the answer.

“Well, Claire,” I said, “We’re going to find out. Be a good girl and get on your knees. And Claire… eye contact. I want you looking at me.” I pulled her hair downward to bring her to kneel in front of me. I kept my hand wrapped in her hair behind her head but clutched onto her skull tightly. She was about to be completely mine.

With my other hand I unzipped my slacks and slowly pulled out my impressive dick. Her eyes went legitimately wide when she saw it and her mouth fell open before looking up at me.

“Sir, I don’t think I -” I pulled her 18-year old head forward and forced her lips around the head of my cock. Her hands shot up to my thighs to try to hold me back but I charged forward, making her take the first few inches into her mouth. She closed her eyes, probably as a defense mechanism, and I’m confident she was astounded when I slapped her left cheek.

“Up,” I said pointing to my eyes. Her lips were completely stretched around the girth of my shaft, she was going to need lip balm – if not neosporin – when this was over. She trembled a little from the aftershock of the slap and the pressure I was placing on her head. I let her start to bob up-and-down on my dick for a minute, seeing how she did on her own, but I was determined to make her satisfy me to a point that was uncomfortable for her. No matter what it took. I wanted to use this little piece of ass kneeling submissively in front of a man almost three times her age.