Claire and Her Boss Pt. 02

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The rest of my Thursday passed somewhat uneventfully. Claire returned to work after fixing her hair and makeup, I wiped off my forehead and sat basking in my accomplishment for almost an hour. I didn’t see Claire again until 11:30 when she sauntered in and asked for my lunch order. I don’t think it was my imagination that her slender, 5″6″ frame was now feeling the full impact of my assault. She was stepping more gingerly than before, no doubt the extremely snug vaginal canal that had surrendered to me a few hours before was now protesting. I would imagine sitting was no better; even though I had only delivered a brief spanking I made them count.

Claire, for her part, made no mention of it again until the end of the day. She walked in at 4:30 and leaned against the doorframe of my office, putting her delicious body on display for me.

“Mind if I take off a little early, sir?” she asked, “I think I earned my paycheck today.” I grinned just a little for her.

“Sure,” I said, “Thanks for your help today, Claire.” She seemed a little disappointed that was all I had to say to her. When she remained in the doorway, antsy, I looked back up and raised my eyebrows. “Something else?”

She teetered on her feet a brief moment.

“Do you mind if I text you later, sir?” she asked, “I was going to have you help me pick out my outfit for tomorrow.”

“No problem, Claire,” I replied. She turned swiftly; her sundress (that had been on my office floor a few hours earlier while she sucked my cock) swung up to reveal the backs of her toned thighs when pivoted, and I began to anxiously await the evening I now had in store.


I returned to my condo, a very well-appointed unit in a highrise. It was summer so I poured a glass of wine and sat out on the balcony, waiting for Claire to entertain me while I soaked up the warm evening air and let the wine take care of my inhibitions. By 8:00pm she started the dance for us.


Hello, Claire. What can I do for you?

Help me pick an outfit for tomorrow. 😉

Great. What are my options?

Well first we have to start with shoes…

The next text I had was a picture of her in front of a mirror, only she had angled the camera down so that I only was able to see her knees and below. In the reflection I could tell her knees had been bruised a little from my rough treatment of her that morning, at the bottom of the photo were her small feet in sexy, black platform pumps trimmed in black lace.

Very nice.

Are they what you want?

Show me another pair.

The next text that came through was roughly the same, except now she was in a pair of purple suede pumps. This time she had pointed her toes inward, giving an innocent look inside what were inarguably “fuck me” shoes. I love the way they made her calves flex and I wanted to move on to better parts…

Those ones. Wear them tomorrow.

🙂 I’m glad you like them, they’re some of my favorites.

A few minutes went by and then I received another photo. This one showed Claire, still in the heels I had selected, but now the photo displayed her from navel to shoes in the mirror. She had donned a pair of a white lace cheeky boyshorts, they were sheer (and therefore see-through) and I had a tremendous view of her waxed mound. Even in a photo of a reflection, and beneath her sexy panties, her pussy looked small and fuckable. Her stomach was perfectly flat and smooth, disappearing into the lingerie seamlessly.

Before I could reply another photo popped up on my phone. My mouth began to water as I saw Claire’s beautiful, lace-clad ass come into view. She had bent one knee and jutted her little arse out toward the mirror for a better shot. Blood started rushing to my dick as I examined how the shorts disappeared into her tiny crack. I wanted nothing more than to rub my prick up and down that slight trench… to watch her tremble and brace herself for a pounding in whatever hole I pleased.

Do you like these, sir?

I thought you weren’t allowed to wear panties to work…

Well if I break the rules I notice I get a huge cock in me soooo… it’s really your fault.

Did you like that?

I did… I didn’t think you’d be so forceful about it though. I’m used to timid boys.

I smirked a little, no doubt that was true. She had told me about an antep escort encounter she’d had with a school administrator about a month before but I didn’t know much else about her sex life before today. She clearly wasn’t a virgin, my guess was she had one or two lovers and probably – as with many teens today – had been going down on guys for several years.

You like your first taste of fucking a boss?

A lot. I couldn’t stop thinking about it today.

Just to play with her emotions a bit I let several minutes pass without a reply. I wanted her to know she was my plaything, she needed to keep my interest… not the other way around. My patience was rewarded when the next text I received was a photo of her, now in skin tight, dark blue jeans. They came to just below her hips and showed off just how skinny she really was. The length of the jeans from waist to her thigh gap gave me a suspicion: it was too small a space to hold the panties she had just shown me.

You took off your little shorts I see.

😐 how could you tell???

Just noticed how low your jeans ride is all.

Well I was going to surprise you… but I guess…

She texted me a picture not of her in the mirror but from her point-of-view, aiming down to where she had now unzipped her jeans and put her flat tummy and bald teen pussy on display. It was a perfect sight.

Gorgeous view.

I’m glad you like it, sir. This view will be yours again soon.

I loved the way she called me “sir.” It highlighted the dominant-submissive relationship we were developing and the (sexy) age difference between us.

Would you like that?

Yes, sir 3:-)

Well you’ll have to earn it won’t you?

Mmmmm… how can I do that, sir?

I was actually in over my head on this one, I had not thought ahead. At 52 I had not grown up with sexting, or flirting electronically in any way, but having stayed on the market for 20 years since my divorce I had picked up a few things here and there.

The question is: how would you like to earn it?

A minute or so went by and I returned to my wine and the summer sun that was now setting behind the mountains.

I guess I’d really like to get on my knees again in front of you, what will you do next time you have your intern’s mouth on your cock?

Well you did pretty good last time, but if you’re coming back for more I guess I’ll

have to really take advantage won’t I?

I hope so ;-D. I’ve always been a little submissive but I really liked you just taking what you wanted. I guess I’m a little sluttier than I thought for you O:-)

Good! Alright send me one more picture and then I’m off to bed soon.

🙁 well fine! I’m already in bed though…

The picture that followed was perfection. This time it was more obvious I was peering into the room of a recent high school graduate, there were photos taped to the wall and what looked to be a cheerleading uniform draped over a dresser in the background. But on the foreground, again from Claire’s POV, were her lean legs spread at an upward angle, her purple heels still on over the covers, and her hand sneaking down between her legs. She was playing with herself for me.

Gorgeous babe. I’ll be thinking of you.


The next day passed in an agonizingly slow fashion. Claire arrived at 8:00am with my coffee in tow. She was wearing the same dark, skin tights jeans that suggested she had remained commando for the day. She had opted for the same purple, suede pump heels I had seen from our texting last night and had donned a black, spaghetti strap tank top that hung loosely around her breasts and stomach but showed off most of her back and all of her shoulders. Her brown hair was up in a tight ponytail, presumably so that her hair didn’t cover up what the tank top revealed. The top came up short of the waist of her jeans, showing just a bit of her smooth lower tummy flesh. There was not an ounce of fat on this lithe teen and I loved it.

By the time lunch came around I was walking around pretty much rock hard knowing I would have my way with Claire soon. At noon I walked to my outer office and, as far as anyone else knew, innocently asked her to come out to lunch with me.

“Of course, sir,” she said as she stood to follow me to my truck, “Where should we go?”

“Well what’s around here?” I asked. After years in that office I knew every place within a five mile radius but I wanted to see what she suggested and take it from there. She leaned a little closer to me to whisper.

“My parent’s house is just a few minutes away and they’re not home,” she recommended.

Five minutes later we were on the highway with her address plugged into my GPS. Claire was a quick learner… I didn’t even have to tell her she would be sucking my cock on the drive. Instead, once we were a safe distance from the office, she leaned over the center console and took my raging hard member out of its constraints. Her mouth was just heaven. Claire went to work, letting the bulbous purple head down her throat while her small hand clenched onto my shaft.

I kept my left hand on the steering wheel and let my right hand roam her teenage body. I had really outdone myself on this one: I squeezed the back of her thighs and loved how toned they were, I rubbed her little pussy and loved the heat I could feel through her size 0 jeans, I grabbed her tight little ass and could feel my dick get just a little bit bigger…

God she was perfect.

After exploring her a little more my hand finally traveled up her back and came to rest on her head. I clenched her skull through her hair and started controlling the motion of the mouth and throat pleasuring a dirty old man. She squirmed a little and repositioned herself, but she took it.

I owned this girl.

When we pulled up to her house I put the truck in park. She moved to get out, and let my cock slip from her mouth, but I pulled on her hair and drove my member back. Claire clearly didn’t expect that but I gave as much pressure as I could with my hand until her throat relented and she finally took my entire manhood. I held her there for a few seconds before letting her back up.

She gasped for air and looked borderline offended until she saw the stern look from me that said, “Don’t you dare complain.” Claire caught her breath and stepped out of the truck, guiding me inside.

Once we had entered her parent’s home and confirmed the absence of anyone else, Claire took me to her room and immediately turned around to face me.

“So what would you like for lunch, sir?” She said, removing her black top and placing her pert teen breasts on display for me.

I looked around her room; it was exactly what you would expect of a high school senior. Claire stepped out of her heels and made to unzip her pants as I caught sight of the cheerleading uniform I had seen in the text message the night before.

“Well one…,” I started, “Who said you could take off your clothes yet?”

She stopped once her zipper was fully down, revealing the perfectly smooth, pantyless flesh underneath her jeans.

“You’re right, sir,” she said with her tongue then pressed to her upper lip, “I guess you’ll have to spank me for that…”

I nodded politely, “And two… where’s that cheerleader uniform from?” She smiled.

“I was on the squad freshman and sophomore year,” Claire replied, “It’s too small now but I used it for a costume party a few nights ago.”

I grunted my approval, “Put it on… now.” I ordered. She practically skipped over to the cheerleading skirt and top draped over her dresser. I went to sit in a desk chair nearby and watched her peel her jeans to the floor, giving me an invasive view of her ass and pussy as she bent over. A few minutes later she had donned the white, polyester top and pleated skirt. She was right: it was too small for her. The skirt came to just an inch or so below her butt and the top barely made it below her breasts.

Before Claire came back to me she spent some time at her dresser putting her hair in pigtails and then she picked up a little tube I couldn’t identify and rubbed it on her face. When she turned around I saw it was subtle, decorative skin glitter for her cheeks. The whole picture made her look even younger than she already did.

As she pranced over to me she moved to get on her knees. I gestured for her to stand up and began rubbing my hands all over her nubile body in this ridiculously sexy costume. I was living the fantasy of several million men at that moment. My hands wandered up her lean torso and under her top. I pinched her dime-sized nipples a moment and then let my hands fall down her back to her ass.

Claire giggled, “I take it you like what you see, sir?” I grunted and gave her a nod before unzipping my pants and pulling my still-hard dick out. Before she could assess the situation I had pulled her onto my lap facing me and maneuvered myself so that the tip of my prick was pressed against her tight little fuckhole.

She took a breath, realizing I was about to make her ride me, and wrapped her arms around my neck. Taking a final look at her pigtails and sparkling face drove me over the edge. I placed one hand on the small of her back, keeping her in place, while the other hand navigated my dick unsparingly into her teen body.

Claire took a sharp breath of air. I let her adjust to the invasion and then used both hands to grab onto her hips and coerce her petite body forward and backward for my enjoyment. After a few minutes she leaned into me with her lips pressed against my neck and started rocking herself back and forth on my member. With every forward thrust I was certain my tip was ramming her cervix… if not something deeper.

Once I was confident her gyrations would continue I reached around to grab her firm little butt cheeks and let my fingertips slip into her crack. I grazed her (likely virgin) asshole but she made no signal of concern. I decided to save further exploration for later as she began to really moan and suck onto my neck flesh. I knew I’d have a hickey if that continued but let her play how she wanted.

It took fifteen minutes, I was amazed I didn’t explode before, but she finally ramped up and made herself cum in a violent quake. The walls of her pussy clenching onto my cock… it took everything I had not to cum then and there but I wanted more.

When she recovered she looked up and bit her lip.

“I guess we forgot one thing,” she said.

“What’s that?” I asked.

“You still owe me a spanking, sir…”

I stood up and guided her to her feet. I tore her cheerleading top off and spun her around so that my dick was pressed against her bare back. She giggled a little and I grabbed both her pigtails in my left hand and then yanked her head back toward me to whisper in her ear.

“You’ve been a naughty little girl today, haven’t you?”

“Yes, sir!” she moaned, “I need to be taught a lesson by my boss!”

With that I took her by the pigtails and bent her over the bed. It didn’t take much to flip her skirt up and I immediately began to roughly spank the minuscule bottom underneath. I alternated the pace, force, and location but after just a few minutes of punishment her soft flesh was glowing red and her head was buried in the mattress as she clasped the sheets with both hands.

What an obedient piece of ass she was.

Once I had soaked in her submission, I let go of her pigtails, grabbed beneath her shoulders, and scooted her up the bed until her entire body was laying flat, face-down on the mattress. I mounted her with one hand pressed on her back, keeping her prone, and used the other to guide my cock into her while she was pinned beneath my weight.

Watching my enormous member penetrate the tiny teenage body beneath me was enough to get me very close, very quickly. I took both hands and grabbed onto her hips and ass pulling her slightly off the bed at the pelvis and then mercilessly powered into her slick, snug twat. Claire was back to clenching onto the sheets again and writhed, twisted, and protested beneath me as I fucked her. Her moans were mixed with intermittent pleading to scale back but I persisted in throttling that girl to my delight.

After just another minute or so I could feel my balls swell and then I gave her pelvis one final pull backward onto my shaft and held her there, balls pressed to her clit, as I unloaded a powerful, unyielding orgasm deep into her womb. When it subsided I kept her body in my hands and rocked her pussy back and forth on my shaft to milk the rest of the seed out of my dick.

Claire was still panting when I removed myself from her folds and gave her one final spank.

“Jesus Christ,” she said, still catching her breath. “I hope we have good health insurance at work.”

I smiled and admired her as she rotated onto her side and looked up at me, the glitter still on her face. I toyed with the idea of taking her again before heading back to the office…

…and that’s when I heard her father open the front door downstairs and walk into the house.

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