My Boss Asked Me To Wear A Short Skirt To Work So He Could Have Sex With Me In The Office

It had been a long weekend since I slept with my boss — since he caught me in a very compromising position and finished the act himself — but I was still surprised that I hadn’t heard from him right away afterward.

I’m not sure what I expected, flowers on my desk, a proclamation of love, a promotion (?), a wink as he walked by? This was all new territory for me.

I’d woken in a daze before my alarm even went off. I remembered the events of the previous night, Jack coming in to his office where I was supposed to be working late and instead catching me at his desk, touching myself and envisioning his masculine hand between my legs instead of my own. He’d seemed pleasantly surprised, right? Why was my phone silent — why was there no word from him?

I was already worrying as I picked out my outfit — a snug black pencil skirt, a semi-sheer black top, black nylons, and black stilettos. I was at least going to look confident if I couldn’t act that way.

When I got to the office I saw Jack’s door was still closed, nothing unusual, I always arrived before him. I sat at my desk outside his office and tried to busy myself, or at least look like I was busy, while I kept watch out of the corner of my eye for him to appear. Nothing.

At lunch I asked our small company’s operations director if he’d be in that day — she was a loopy older lady but she always knew everything that was going on in the office. “Didn’t you hear,” She said, with a genuine look of surprise on her face, “Jack’s traveling. Last minute trip for the DRI client. He sent an email out this morning.” My heart sank again, I hadn’t gotten the emailed, and he always cc-ed me on stuff like that. Maybe he was unhappy about what happened. Something was up.

Back at my desk I racked my brain for a manufactured reason to contact him. I had to see what his tone would be like in the response. Finally, I just went with something that seemed even remotely plausible:

Hi Jack–

I heard you had to travel today last minute. Do you need me to take care of anything here at the office?

-Adrienne

And then I waited impatiently for a reply to appear in my inbox. Several hours of hitting refresh later:

Adrienne–

Thanks for working late last night, I have everything I need for the meeting. We’ll speak tomorrow.

-Jack

As I finished reading, I felt my phone buzz on my desk. It was a text from Jack, “PS wear a skirt.”

Jesus.

Okay. Everything was fine. More than fine. That was a flirtatious text. He didn’t regret following his impulse, bending me over his desk. He wanted more. Good. So did I.

Jack was always a weird combination of mysterious and forthright. He was blunt and honest whenever I asked him about something, but he never shared without prodding. It intrigued me, or at least made me feel flattered that I was getting to be privy to his private side. And I’d find out even more soon.

I spent the rest of the afternoon online shopping for the perfect short-but-not-too-short skirt to wear the next day and fantasizing about having his hands on me again. The sex we’d had was primal, passionate — I wasn’t sure how it could get any better but I’d be thrilled with more of the same. I drove to the mall after work to try on a few of the more promising skirts, the sensation of pulling them on and off felt heightened, I was very aware of everything touching my skin. Luckily I found the perfect almost knee-length but flouncy black skirt I could wear with a thin sweater tucked into it. If I was a guy, this would be totally hard to resist.

Feeling emboldened by Jack’s text I couldn’t help but be flirtatious, it was hard to say no to myself with how wound-up I was feeling inside. I snapped a photo of the skirt in the dressing room mirror and texted it to Jack. I expected no response, or at least I must have not expected a response because I was surprised when I heard my phone buzz a few minutes later. It was Jack:

Shorter.

I gasped out loud in the cashier line and then exited it to purchase another skirt I’d tried on — the one I thought was probably inappropriate for work. I didn’t care if it was inappropriate for work, the job didn’t mean much to me and I was so shocked by Jack responding with anything other than a compliment, it just wasn’t how most men acted. I wanted to please him enough to learn more.

In the morning, as I pulled on my new skirt and straightened the shirt I was wearing with it I felt more nervous than I could remember being. This was a dumb sex thing with my boss, sure, it was probably irresponsible, but I was responsible in more than enough other areas of my life to make up for it. I wouldn’t be at this job long, I may as well have fun here. And I’d never experienced something so intoxicating as the way Jack had handled me. The roughness of his touch coupled with the pleasure in his eyes and in his voice.

When I got to work I was surprised to see Jack’s door was open, he was early. With trepidation and a kind of butterfly feeling that extended downward from my stomach, I knocked on the door and peeked in, “Jack?”

“Good morning Adrienne.”

He was sitting at his desk, reclining. He looked very sexy like that, both playful and poised.

“I see you follow instructions well,” He said, his eyes glued to my legs — quite a bit of which were uncovered by the skirt I’d decided on.

“Only for you sir.” I laughed as I said it.

It wasn’t funny but the intensity of the situation made me giggle. I wasn’t used to being so serious. I walked to his desk and perched myself on the edge of it, trying my best to look sophisticated. He placed one hand on my bare thigh rubbing it, dangerously high. I glanced back at the open door, no one was due in for a bit longer, but that what if someone came in early? Shouldn’t we shut it? And yet… I could also feel my worries being drowned out by another voice inside me that was praying his hand would keep moving.

“Not now Adrienne. I just want a peak of what I’m going to find later.”

He pulled me off the desk and into a standing position in front of him and moved his hand farther up until I could see a look of pleasant surprise cross his face as he realized I wasn’t wearing panties. He bit his lip.

Feeling awkward about just standing there while he touched me I leaned forward to kiss him. He turned his head so that he could whisper in my ear, “Good girl Adrienne.” Then he kissed my earlobe and continued down my neck, one of his fingers now inside me making strong, circular motions. I gripped his chair for balance as keeping upright on my own was becoming increasingly difficult. I couldn’t think with what he was doing to me.

He pulled his hand out of my and placed it on the back of my thigh. I could feel some of my wetness smearing down my leg and I wasn’t sure if he’d intended that or not, but it was hot.

“Mmm. I’m going to bend you over my desk later. After I’m finished with my lunch call.” It was a statement, not a request — and he was right about that, there was no way I was saying no. He looked at me and I nodded, pulling my skirt down as far as it would go. I turned to leave his office until the appointed time and was dismissed with a playful slap on the back of my skirt.

I returned to my desk and waited to be summoned.