Naughty Little ‘Schoolgirl’


Nobody warned me that at Circle Logistics, you just don’t dress up for Halloween. Seriously. I was expecting to stand out a little in my plaid schoolgirl skirt and tiny white top, but as soon as I walked in I realized I was the only person who was even acknowledging the holiday. The entire office staff looked up from their desks to stare at me. My heart sank and I steeled myself for one hell of a day.

Walking past the rows and rows of grey cubicles, my platforms made an excruciatingly loud click-click on the linoleum. The people in the cubicles were all wearing their normal white button-ups and slacks with sensible, non-clicky shoes; their expressions ranged from amused to disgusted.

The new CEO of Circle Logistics wanted a young, hip advertising executive who could bring a fresh perspective to their otherwise uninteresting company, so he hired me. I was used to working for trendy graphic arts companies or freelancing for indie bands, but hell, Circle Logistics paid pretty well and at 25, I was anxious to pay off my substantial college loans.

Jake McDonald seemed to enjoy the irreverence of my ad campaigns but I was never sure whether or not he actually liked me. We occasionally exchanged flirty IMs but he always pulled back as soon as I got too sassy. At meetings, I wasn’t afraid to challenge him and always gave my advertising reports with a healthy dose of wit that made my coworkers slightly uncomfortable. I knew the office was a bit suspicious about our relationship. Sadly, they had nothing to be suspicious about. He’d been kind but professional, even when we were alone together.

I had a huge crush on him. He had that young-powerful-executive thing going on. He was just shy of 35, with a slim build, dark brown hair and black-rimmed emo glasses. His eyes were an interesting shade of light green, standing out from his pale, nearly translucent skin. He wore black most of the time—black button-up shirt, black slacks, shiny black tie. Jake was always clean-shaven and had a metrosexual, chic vibe. Oh, and he wore the most amazing cologne I’d ever smelled. As far as I could tell he was single. He worked late nearly every day, chained to his desk slaving away at budgets or spreadsheets or whatever CEOs do. His glass-walled office was in the center of all of the cubicles so he couldn’t miss the fact that I’d covered my cubicle walls with bright blue-and-yellow fabric or the way my trendy outfits drew stares from the identical drones working around me. Honestly, my cute Halloween costume was intended to test him out, see if he might actually have the hots for me like I did for him.

As I turned the corner and entered his line of vision, Jake glanced up and took in all of it—my short skirt, my exposed tummy, high heels, pigtails… I looked straight at him, smiling confidently, daring him to call me into his office and chastise me for actually having a bit of fun on Halloween. The rest of the office was looking, too, probably hoping he’d fire me on the spot. He just nodded at me and looked back to his computer screen, fighting to control a smile spreading over his face.

When I got to my desk, an instant message popped up. I knew it. I just knew it. This was too easy.

JMcDonald: I see you enjoy celebrating Halloween.

WickedCoolAnna: it’s my duty as in-house creative whirlwind to bring a bit of holiday spirit into the office.

JMcDonald: You could have carved a pumpkin.

WickedCoolAnna: in the office? messy. a costume is more exciting and doesn’t interrupt the all-important Business of Logistical… Logistics.

JMcDonald: I would disagree. I for one am finding it very difficult to continue the Business of Logistical Logistics.

He has a sense of humor! Excellent.

WickedCoolAnna: why is that, mr. mcdonald?

JMcDonald: Your skirt is quite short. Quite, quite short. And your top is completely unacceptable as office wear.

WickedCoolAnna: perhaps I should remove it.

JMcDonald: Perhaps you should.

WickedCoolAnna: i am radically offended at the suggestion that i should take off my shirt.

JMcDonald: And the skirt as well, I’m afraid.

WickedCoolAnna: skirt as well?!!! then, yes, i am radically, radically offended. especially as my underwear is also quite inappropriate.

JMcDonald: An examination might be in order.

WickedCoolAnna: i could just describe it for you. no examination required.

JMcDonald: Examination referred to your performance, not your bakırköy escort thong.

WickedCoolAnna: objection: never mentioned it was a thong

JMcDonald: I’ve observed your tendency to allow a thong strap to peer out over the top of your ever-shorter skirts. Therefore, I find it safe to assume that your “inappropriate” underwear might be in the thong family.

WickedCoolAnna: you do keep close tabs on my performance.

Long pause. My IM window told me JMcDonald was typing, then stopping, then typing again, then stopping. He seemed to be unsure of whether to send whatever he was writing. Finally it came through.

JMcDonald: I would like to keep closer tabs on your performance.

Was that a totally awkward way of hitting on me? Might as well move in for the kill.

WickedCoolAnna: well i would be available for a private meeting later…???

I held my breath and looked up. Jake was looking at me, too, and our eyes met. Was that too fast? Shit. I should have played that better. I could tell he was wavering. I didn’t know whether he was struggling with the whole employer-employee ethical thing or whether he was trying to figure out a nice way to tell me he wasn’t interested.

WickedCoolAnna: sorry.

WickedCoolAnna: am i fired?

JMcDonald: No.

JMcDonald: Stay after work.

YES! I restrained myself from doing a happy dance and sent back a smiley. The rest of the day dragged by… I didn’t know what Jake wanted from me, but I know what I was hoping for. All of that sexual tension had been killing me and I was dying to see what Jake really thought of me. Maybe he was going to ask me out on a date; maybe he’d just tell me to back off. Or maybe he’d do me on his desk. Who knows.

After a day filled with snide comments and all-out drooling from my male coworkers, six o’clock rolled around and the rest of the office workers gradually filtered out. It wasn’t uncommon for me to stay at my desk late to finish a project or meet a deadline. I did catch a few suspicious looks from the last stragglers, who looked darkly from Jake to me and shook their heads. They could think what they wanted. Honestly, I hoped whatever sick, twisted and totally imaginary situations they were envisioning were about to come true.

Everybody left by 6:45 but I stayed at my desk, pretending to work on the company’s new print campaign. Sketching idly, I tossed a failed design into the trash can next to my desk and glanced up innocently… Jake was watching me. At 6:50, his voice came over the central loudspeaker, startlingly loud in the empty office.

“Anna Stevens, please come to Jake’s office. Anna Stevens.”

I looked up and Jake was grinning at me like a little kid, amused by his own joke. I laughed. Standing, I adjusted my skirt and top, letting Jake see me smoothing the plaid pleats and running my hands over the knot of my white top.

I opened the door to his office and stepped inside. “Hi. You called?”

“Yeah. I guess the loudspeaker may have been unnecessary. Are you ready for our meeting?” He got up from behind his desk and walked to the center of the roomy office. Even in the harsh florescent light, he looked gorgeous. He was wearing all black as usual and the subtle, spicy heat of his cologne washed over me as he approached.

I felt a little flutter in my stomach and covered it by saying flippantly, “I’m not sure what we’re meeting for. Is it to chastise me for actually having fun on Halloween, or do you seriously want to talk about my performance?”

He stepped even closer. “Actually, I was… um…”


“I was hoping to kiss you. Can I, um… Can I?”

Was he blushing? That’s totally adorable. “I wondered when you’d ask me that.” He was standing right in front of me.


“Yes.” He put a hand on my shoulder and used the other one to cradle my chin, bringing his lips to mine. Jake’s mouth was soft and cool against my full lips. His tongue slipped through my lips and bumped into mine, pulsing against it gently. We slowly moved our bodies together and his hands ran over my back, pulling me in as our kiss deepened and became more urgent. Mouths open, tongues kneading, we kissed each other hard. I inhaled his smell and pressed my hips into his, surprising both of us. Jake raised his hands to my long brown hair. His fingers twined at the nape of my neck. Still kissing me, he maneuvered me in a half-circle and started backing beşiktaş escort me up toward his desk.

When I felt the desk behind me I pulled back from the kiss. “Are you sure this is okay? Anyone could walk in…” I looked around at the glass-walled office with a 360-degree view of the empty building. I was already pretty damned turned-on but I didn’t want to get Jake into something he’d regret. In response, he took my arm and moved me off the desk. My heart sank and I immediately regretted saying anything… Until, with one wide movement, Jake swept papers, staplers, folders and binders off of his desk, leaving it empty except for his laptop. I raised an eyebrow. “Impressive.”

“I’ve always wanted to do that. Didn’t think it would be smart to drop my laptop, though.” He shut it and moved it carefully to his chair, then whirled around and took my hips in his hand. We returned to kissing ardently as I backed myself up to his huge, now bare desk.

Hopping up on the desk, I scooted myself backward and pulled him down on top of me. He tensed up for a brief moment, surprised at my fast transition from pure kissing to a horizontal position. Now that he was on top of me, I felt the bulge of his dick pressing against my skirt. He was already hard and I moved my legs apart slightly as I kissed him, enjoying the heat of his body against mine.

Jake got over his surprise quickly. He ran a hand down my neck to my chest, squeezing the side of my breast through the thin white fabric, then taking my left arm by the elbow and raising it slowly above my head, keeping his hand on my wrist. I wriggled with pleasure and, encouraged, he used his other hand to raise my right arm as well, holding both of my wrists firmly with his right hand as we made out. Our breathing became more rapid and I thrust my breasts up toward him, enhancing my tantalizingly vulnerable position.

Jake kept my arms above my head and started moving his left hand across my body, raking his fingers over my exposed midriff and down to the pleats of my skirt. Hit by a wave of lust, I turned my head to the side and Jake attacked my neck, nipping and kissing across my jawline as his hand moved around the front of my thigh, tickling it gently. He pushed my skirt up and stroked the front of my white lace g-string. Moving his hand to cup my breasts, he ground his hips against mine and deftly untied my shirt. His mouth found mine as he opened the white fabric, exposing my sexy satin bra.

The schoolgirl skirt had climbed up around my belly button and Jake’s belt dug into the sensitive skin at the top of my g-string. He felt me trying to angle away from him and pulled away enough to unbuckle his belt. He also undid the buttons of his black slacks and slipped them down. Now only my lace g-string and his smooth briefs separated us. Keeping my arms above my head, he unbuttoned his shirt and pressed his smooth, warm chest to mine as our mouths melded hungrily. I spread my legs and wrapped them around his hips tightly. Jake kissed down my neck to my chest and grabbed the bra’s elastic top in his teeth, pulling it down to expose my hard and aching nipples. His lips curled around each breast in turn, sucking, licking and biting gently as I gasped at the changing sensations.

“Jake, I want you to do me,” I urged, lust rising as I felt his hardness just above my g-string. Without speaking or ceasing his assault on my nipples, he eased his briefs down and I felt his cock spring out fully erect and slap against my crotch. Jake hooked a finger under the back of my g-string and pulled; the elastic dragged against my skin as I lifted my hips, letting Jake pull the panties down far enough for me to shimmy them all the way off. He did the same with his pants and briefs, leaving us naked except for open shirts and the bra Jake had yanked down past my breasts.

Looking into Jake’s eyes, I felt his cock move across my opening, back and forth in a gentle motion. I knew he was coating his dick in the wetness of my arousal, preparing to fuck me like I’d been dreaming he would for months. I spread my knees wide and pushed myself forward, encouraging him to enter me, burning with passion and leaning up to kiss his lips. He stared at me and smiled slightly. His cock pressed at little way into me; I felt how thick he was. The word “please” shaped on my lips as I looked at him pleadingly, needing to feel the length of his cock.

He entered me inch by excruciating beylikdüzü escort inch. His eyes never left mine. I moaned and tried to free my hands but he held them fast as he tortured me with a slow descent.

Jake’s dick connected with each nerve ending in my pussy in turn, making its way up my wet and throbbing passage. I felt the head of his cock scrap against my walls. Finally, he couldn’t take it anymore and pushed himself all the way into me, hitting the back of my wall and making me cry out in pain. He paused, making sure I was all right, before slowly beginning to thrust in and out of me. He closed his eyes as he fucked me slowly. I saw him enjoying the way my tight, smooth pussy held onto his huge cock, clasping it in a firm embrace. He pulled himself nearly all of the way out of me with every stroke. Pausing a bit at the top, he would thrust smoothly until he buried himself and his pelvic bone ground against my tingling clit.

His dick moved over my g-spot with every stroke and pleasure began washing over me in regular waves. The slow fuck was exactly what I needed to cum like a freight train. I felt it building inside me and whispered, “Yes, Jake… That’s it. Just like that.” He slid in and out of me with delicious rhythm and my body became incredibly hot. A warm buzz washed through me and I felt myself clutch wildly at his cock as my orgasm went over the edge. Responding, he quickened his pace and groaned as my tightening pussy massaged his dick. I moaned as I came, my juices coating him as we moved in perfect rhythm.

As my orgasm wound down, Jake put his feet on the ground and picked me up, keeping his cock firmly inside of me. I cried out as he swung me around, spearing me as for a brief moment I sat suspended on his dick. Then my knees found the desk and I was riding him, instantly shifting from controlled to dominant. I leaned back and closed my eyes as I took in the pleasure of the new position. His arms wrapped around and squeezed my ass. I pulled my knees close to his hips to increase my grip on his dick as I alternated between bouncing up and down and dragging my hips in circles, constantly changing angles and tactics so he was bombarded with sensations. He groaned my name softly. I took it as my cue to increase my speed and bounce up and down on his throbbing dick, forcing him deep into me with every push. I leaned forward so my clit connected with his skin every time I fucked him. As I felt him nearing orgasm my pleasure grew and I knew if I concentrated, I would come a second time. I focused on the feeling of his cock pumping in and out of me. I felt every inch of him thrusting deep into my pussy and concentrated on the shooting waves of ecstasy moving through me every time my clit pushed against him.

Losing control, Jake began lifting me and slamming me onto his cock as he thrust upward. I surrendered to my second orgasm just as his dick tightened and loosed its load with warm, wet passion, filling me as my pussy muscles clenched around him. We came hard. I rode him until we both collapsed, spent, exhausted and shaking with the force of our orgasms.

His cock still inside of me, I let my heart rate slow as I smiled at Jake. He grinned back. He looked unbelievably hot, shirt open, pants off, sitting on his bare desk surrounded by an ocean of papers and spilled folders. Especially from my vantage point, sitting on his spent cock with my shirt open and my underwear somewhere on the floor. I knew as I looked at him that this wouldn’t be the last time we’d have sex on that desk.

Minutes later, fully clothed and somewhat cleaned up, Jake and I walked out of his office. I stopped by my cubicle to grab my purse and caught my breath. My trash basket was empty. That meant–

“Jake, the janitor was in the office while… Yeah. He must have, um, seen.”

Jake was standing in front of my computer. Wordlessly, he reached out and peeled a Post-It off of my monitor. On it was a crooked smiley face and the words Happy Halloween, Jake and Anna.

I cringed. “Oops.” Jake was laughing silently. He took my shoulders and kissed me.

“I don’t think we have anything to worry about. Todd’s a buddy of mine. I’m sure he was just glad I finally made my move with you.” Pleased, I kissed him back and picked up my portfolio before heading out the door.

Circle Logistics was suddenly a lot more interesting. “Happy Halloween, Jake,” I said as we parted ways on the sidewalk.

He smiled in return. “I was right about the thong.”

“It was a g-string, actually.”

“There’s a difference?”

“Of course there’s a difference.”

“Really. I’m not sure I’m clear on that concept… Maybe we need another meeting tomorrow?”



I love my job.

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