My Boss Didn’t Like My Outfit, So He Made Me Strip For Him


My boss and I had gotten into a routine over the last few weeks: I would wear short skirts to work and try to pass the time “working” from my desk outside his office. Really though, I was texting him dirty things and we’d chat back and forth until we couldn’t take it any longer — at which point he’d summon me into his office (“Adrienne, I need you to step in here for a moment for a conference call”) and bend me over his desk. It never took more than a few minutes, we were both so wound up by the time we actually touched each other.

My days were always a blur, everything was so exciting, I was lost in fantasy — or else living it out — every minute. I was always either revving up or winding down — building anticipation or releasing it. When I woke up, I couldn’t wait to go to work. Life was fucking great.

My boss, Jack, seemed to be enjoying himself too. At least, if his near-constant erections were any indication.

Today I’d outdone myself in preparation: brand new thigh highs that were hidden underneath my dress, the lacy tops of which ended just a few inches below the tippy tops of my legs. I thought he’d appreciate how they made me seem dressed, even while undressed. In the semi-privacy of the area under my desk I pulled my dress up a bit and snapped a pic of the thigh highs and texted it to Jack. There, let him try to work with that on his mind.

I went to the break room to get a glass of water and sure enough, when I returned Jack was calling me. “Adrienne? Is that you? Can you come in here for a sec?”

Gleefully I set my water down and practically skipped into his office. I shut the door behind me and turned. That’s when I noticed things were off.

Nate, our 41-year-old human resources director was seated across from Jack at the table in his office. “Have a seat Adrienne,” he said as my heart quickly sank to the very bottom of my chest, “we have something to discuss.”

He knew.

That was all I could think, over and over. Jack owned the company — would it matter if we were being bad? It must or we wouldn’t be having this meeting at all. Maybe he wanted to put an end to it and he chose the most bizarre method imaginable?

Nate cleared his throat and dropped the bomb, “Adrienne, we’ve had some complaints from the staff about your wardrobe. The length of your skirts is simply not professional.”

I looked at Jack, trying to see how he wanted me to respond. I was only wearing such short skirts by his request!

“Umm, I’m so sorry.” I started. This was actually humiliating. I was going to throw up. Or cry. But I needed to get through this conversation first. “I had no idea, I just thought that was… um, like the style now. I won’t wear them anymore.”

I was trying my hardest to not react, to be monotone, to not be the emotional girl who cries at work — to moderate success. My voice was cracking a bit by I think my expression was blank.

Nate looked really uncomfortable. I searched Jack’s face for his reaction. He finally spoke, “Adrienne… I think this is a bit silly. But we can’t have you making people uncomfortable and interfering with their productivity. Since Nate isn’t in the office every day I’ve volunteered to be the neutral party here. I’ll be enforcing your promise to dress in a way that is consistent with the professional values of this office.”

There it was.

The right corner of his mouth twitched upwards. He was enjoying this! It was so infuriating. I was extremely stressed out, mustering all my internal strength to simply not cry and he was fantasizing about chasing me around the office with a ruler to measure the length of my skirts. I promised Nate, again, to be extremely conscious of my clothing, thanked them both, and dismissed myself. I grabbed my purse and took and early, unannounced lunch. I needed to clear my head.

When I returned it was to a post-it on my desk from Jack.

Let’s meet offsite tonight. Filio’s. 8pm.

There was no way to answer yes or no, his door was shut, he was gone for the rest of the day. Though, frankly, even given the sobering discussion I’d just had, I was excited to take our fling out of the office. He was taking me to dinner. This was a welcome change of pace.

When I arrived at dinner, I couldn’t hold myself in. “I can’t believe you were smirking while I was getting in trouble!” It was the first time I’d ever raised my voice to him. “I was only wearing those skirts because YOU asked me to!.”

He laughed as if this was some hysterical joke. And, honestly, it was pretty funny. Like your parents catching you make out with a guy outside the middle school dance.

“I am going to enjoy measuring your skirts, however.” He looked devilish. Of course he was, he was getting of scot-free.

“You know it only makes me want you when you talk like that.” I didn’t want to stay mad at him, and the whole thing seemed silly now that we were out of the office. “But maybe we do need to keep it out of the office?”

“I have no interest in doing that,” Jack said, his tone matter of fact. “I feel more invigorated in my work than I have in a long time.” Now he looked vulnerable, like he was admitting something that made him uncomfortable. He was letting me in, if just a tiny bit. He realized this at the same time I did, as he sounded a bit harder when he continued. “You will have to choose. Tomorrow I will measure your skirt and if it’s not short enough for me I will punish you. Of course, as your boss I’m going to have to encourage you to follow human resources suggestions… so it appears as if you’re stuck.”

I swallowed. The way he hung on that phrase, I’m going to have to punish you. I couldn’t help myself from writhing a bit in my chair, the promise of this idea tugged at me between my legs. I had no intention of following Jack’s orders. I needed to see what his punishment would consist of.

“We’ll have to see tomorrow,” I said as coyly as I could. I tried to act sexy around him, but I was so enthralled I had no idea if it worked. At least now I had a hint he felt the same way. He winked and my body doubled down on the familiar pang of lust below my abdomen.

In the morning I put on one of my old outfits. I wasn’t going to stoop so low as to wear pants, but this dress hit just below the knee when I was standing. The old ladies in the office would have nothing to complain about. But Jack would…

I was standing in the hallway when he arrived, putting away some files he’d used the previous day. He eyed me with a mixture of disapproval and excitement. I knew what was coming.

Sure enough, a few minutes after I got back to my desk I heard his familiar call, “Adrienne, can you come in here?” Excited, I walked into his office.

“Shut the door behind you.”

He was standing in front of his desk, leaning back on it with his arms crossed. He had that far-off look of concentration he had when I was pleasuring him. I loved that look.

“Tsk Tsk. Your skirt is far too long. Come here so I can check.” I obliged, approaching him. He pulled at the fabric and made an exagerated noise of disgust. “The fabric is so thick! It leaves far too much to my imagination. And you know what happens when we leave things to my imagination.”

I quivered. I couldn’t help it. His calmness — the way he controlled the whole situation. It made me drunk on him.

“Um, yes I do know what happens?” I wasn’t sure how he wanted me to respond.

“Show me what I’m missing out on.”

I lifted my skirt in the front, enough to reveal the lacy thong I was wearing underneath.

“Let me see the back.”

I turned and allowed him to see my bare butt. Even though we’d had sex in his office many times, we always kept our clothes mostly on. I was more nervous now. He was just standing there, examining me. I felt very exposed.

“Strip for me.”

He wanted me completely naked? I didn’t love that idea… his office was brightly lit and we weren’t in the throes of passion or anything. I’d just be standing there, all my flaws out in the open.

“Adrienne, don’t hesitate. I’m already displeased with you.”

I grinned. For some reason when he expressed displeasure it didn’t come across as disrespectful, but of caring enough about me to know I wanted to turn him on. I pulled my sweater over my head and unzipped my skirt before stepping out of it.

“Bra and panties too.”

I removed them. The sensation of standing before him completely naked while he was fully clothed was surprisingly intoxicating. I moved toward him, I needed him now.

“I want you to get on your knees and tell me why I should fuck you when you won’t even wear your lovely skirts for me.”

I obliged. “Please Jack. I’m sorry. I had to. The women in the office — they’d complain to Nate again if I didn’t change.”

“And who do you care about pleasing?”


“That’s right. Now come here”

He took me and bent me over his desk (finally I thought) but it wasn’t for the reason I’d hoped. He spanked me. Hard. Methodically. Rubbing my ass in between slaps, savoring it.

“Jack,” I breathed. I couldn’t handle this anymore. “Can you please fuck me now? I’m so turned on.”

“And you think you deserve it now?” He still sounded stern.

“Pleeease.” It was all I could get out. I was writhing on his desk.

“You might not, yet, but I’ll indulge you this once.”

I heard him unzip his pants and I paused to spread my legs out, providing him easy access. He entered me quickly, without easing into it and thrusted hard right away, pressing me into his desk. I felt his hands grab my hips and pull me back into him, quickly.

“Mmm, you feel so fucking good.” He was losing himself, I could tell. He groaned as he fucked me. The build-up had been inside him, too.

“Cum inside me, please.” I begged him. It wasn’t a fetish I was into, or something I’d even thought about before that moment. But I wanted it and the volume of his groan in response solidified that it was a mutual desire.

With a few final pumps he emptied himself into me and pulled out. I lay breathless on his desk, too wasted to move. He handed me my clothes, “Maybe you’ll think more wisely about your wardrobe choices tomorrow.” Thought Catalog Logo Mark

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