She was already seated in the clear plastic chair in front of her desk, not the big throne-like one behind it. I didn’t dare take that chair, so I stood in front of her, nervously presenting myself. Her online profile said that her name was Harlow. She looked exactly like her profile picture. The only difference was that she was wearing all white latex, not the black leather from her photo.

A lit cigarette dangled between her fingers. I didn’t think you could smoke indoors. I was pretty sure there was a bylaw against it, but everything about Harlow suggested that rules were for other people to follow. Not her. At least not here.

“Tell me about yourself.” Her voice was firm, but softer than I expected.

My mind went blank. Earlier in the week I’d already gone through a pre-screening with her assistant and told her everything about me. Even admitted to some things I’d already regretted. I couldn’t think of anything that I hadn’t already said.

“Well?” she asked impatiently.

She was still waiting for an answer, and my nerves weren’t letting one move from my brain to my mouth.

I’d never done anything like this, and whatever I thought it would feel like, this wasn’t it. I was used to commanding a room, not shrinking inside one. I started shaking and couldn’t stop. Harlow noticed and smirked.

She reached across to her desk and picked the top folder off a small pile that was neatly stacked near the edge. It had my name on it. I recognized the first page as the questionnaire from my intake interview. I think she’d grown tired of waiting for me to speak and decided to see what she could learn from the file.

“It says here you’re a Wall St. manager. Is that true?”

“Yes.”

Her eyebrow went up in a way that told me I’d already screwed up.

“Yes Mistress Harlow.”

“I’m not your Mistress,” she corrected me. “Not yet. Call me Miss or Miss Harlow.”

“Yes Miss Harlow.”

She smiled, and I felt a rush of relief I wish I could have hidden.

“That’s a stressful job, isn’t it? High stakes. Lots of pressure. People look to you for answers. It’s all on you.”

“Yes Miss, it’s a lot.”

“You’re used to being in control, aren’t you?”

“I am, Miss.”

“And that’s what brings you here? You want to let go?”

I shook my head yes. She didn’t like that.

“Use your words.”

“Yes Miss Harlow. I… I need a mental break. To not be in control. To just do what I’m told. I don’t want to have to worry about – “

“Enough.” She cut me off.

Her eyes went back to the file. She read for a few moments, then turned to the second page. Her expression changed a few times as she read the assistant’s notes. She shook her head through one part and winced at another. At one point she brought her hand up to her mouth to half cover a laugh. After flipping through a few pages, she closed the file and tossed it back on to her desk like she’d seen enough.

“You’re far from original. You Wall St. types are a cliché at this point. You all think you want the same thing. But I know what you actually want.”

“You do?”

“I do. And right now I want you to take your clothes off.”

“Here? Now?” I was confused. I didn’t think it was a session. Intake said this was just a first meeting to go over some things. I wasn’t ready for this.

She stood from the chair and kicked it back, knocking it to the floor. She wasn’t angry, didn’t raise her voice, but her cold detachment suddenly felt serious.

 “This is the only time I will say this.” Her voice was stern. She was scolding me like I was a child. “I do not repeat myself. I say something. You do it. That’s how this goes. Understood?”

“Yes Miss Harlow.”

I began loosening my tie with shaking hands. She walked across the room to a large cabinet and opened the doors. I couldn’t see what was inside, but I caught glimpses that made me shudder. 

“Faster,” she said with her back still turned to me. She somehow knew without looking that I was struggling with my shirt. It came off and I wasn’t sure where to put it, so I held on to it as I started to undo my belt.

Miss Harlow looked at me over her shoulder, then nodded to the plastic chair she’d knocked over. I went over, set the chair upright, laid my shirt over the back, and placed my tie on top of it.

I fumbled with my belt. My fingers kept slipping. I told myself it was the buckle, but it wasn’t. It was her. When my pants came down, I was already hard. I tried thinking of data reports and sad stories, but my eyes kept going to Miss Harlow and the way the latex hugged her body. I wasn’t going to be able to hide it. For a second I thought about running, but I needed this. I folded my pants and set them on the chair, then stepped out of my socks one at a time. All that was left were my boxer shorts. I took a deep breath and pulled them off.

“Look at you,” she said with a wicked smile and a mocking tone.

Instinct made my hands move to cover myself.

“Ah, ah, ah,” she said, shaking her head. “No, no, no.” She took a few steps closer. That’s when I noticed the crop in her hands. “That little guy stays front and center.”

I slowly moved my hands to my sides and lowered my head. I was too embarrassed to want to see the expression on her face.

Miss Harlow began to walk in a wide arc, circling me as she spoke.

“Rule number one. When you enter this room, you remove your clothes. No exceptions. None. Ever. Is that clear?”

“Yes Miss Harlow.”

“Good. Rule number two. As much as you’re paying me, I don’t work for you. I don’t perform for you. The boxes you ticked off during intake weren’t menu options. They help me understand you. I decide what happens in this room. Not you.”

I nodded, then caught myself. “Yes Miss Harlow.”

“Finally, and I cannot stress this enough, what I say goes. You have your safe word. Use it if you have to. Short of that, when I speak, you act. You don’t question. You don’t hesitate. You do it. Understood?”

“Yes Miss Harlow. I understand.”

She finished her loop and was in front of me now.

“What’s this?” she asked, tapping her crop against my stiff cock. I blushed.

“It’s… um… it’s… I’m sorry Miss Harlow.”

She laughed out loud. “You should be sorry. Not because it’s hard. Because it’s small.”

“I’m sorry—”

She cut me off again. “Do you think all the people who work for you, all the ones who think you’re a big, powerful man, know your ‘little’ secret?”

“No Miss Harlow.”

“They’d laugh at you, wouldn’t they? The way I just laughed at you.”

“I think they would, Miss Harlow.”

“I know they would. Maybe I should send a picture to my girlfriends. Imagine it. Young, beautiful women all laughing at you. Your money won’t impress them. Not with that worm in your pants.”

Her words were crushing. I’d mentioned humiliation on the questionnaire, even watched videos online, thinking it would help. But in person, with her standing in front of me, it wasn’t the same. Miss Harlow was real. She was looking at me. Talking about me. I couldn’t press pause or click on a different link.

“Look at it,” she said, giving it another tap with her crop. “It’s twitching. Bobbing up and down all by itself. Not because you’re about to get some pussy. But because someone is finally telling you the truth. It’s tiny.”

It was hard to deny with her staring straight at my cock.

“Tell me something. When was the last time you got laid?”

“A month,” I said, then realized it had been longer. “A couple of months, Miss.”

“Mm. And how did you know her?”

I hesitated. I knew I wasn’t supposed to. I saw her expression change, like she was about to scold me again. “She was an escort.”

“Of course she was.” She placed the crop under my chin and lifted my head. “When you pay them, they don’t laugh. They pretend. What she gave you was a lie. This is truth. That’s what you want, isn’t it?”

“Yes Miss Harlow.”

“And what is the truth?”

“The truth is that I’m not the man I pretend to be.”

“More,” she said firmly.

I didn’t know what she wanted from me but I didn’t want to disappoint her by not answering. “My job… it lets me be an asshole. People are afraid of me. I boss them around because it makes me feel big.”

“I’m glad I don’t have to drag it out of you. You know exactly what you are, little Timmy. I’m only holding the mirror.”

Miss Harlow saw right through me. She knew all of my weaknesses. Like calling me Timmy instead of Timothy. No one had called me that since I was a kid. I’d fire someone if they called me that at work. Here I had to take it.

She was behind me now, close enough that I could feel her breath on my neck. “You’re going to be a fun one. I can tell,” she whispered. I felt the snap of her crop against my ass. Not hard, but enough to make me jump.

She walked across the room and sat in the big leather chair. It looked even more like a throne now with her sitting on it. She opened my file again and propped her feet up on the desk.

“All of this,” she said, flipping through the pages, “these half-hearted confessions, all this fluff you thought mattered.”

I hadn’t moved since she struck me. I was too afraid to.

“Face me,” she commanded.

“All of this is bullshit,” she said, dropping the file into a wastebasket. “Because when you’re standing here naked with your little boner sticking out, you can’t hide who you are.”

She went quiet after that. It might have been for a minute. It could have been twenty. It was a strange moment of peace. For the first time in a long time, I wasn’t in control of anything. I was just standing in a room, naked.

“You know what,” she finally said, picking up her phone. “Someone else needs to see this. No one’s going to believe me if I tell them about your little thimble dick. I need a witness.”

She began dialling, and I panicked.

“Red,” I said quickly. “Red, Miss Harlow.”

She calmly placed the phone facedown on her desk.

“Noted,” she said. “But understand something, Timmy. If the idea of being seen hits you this hard, it means that’s exactly where your mind wants to go.”

She rose from her chair, and somehow I felt even smaller.

“The very thing that made you safe-word today is what you’ll be begging me for in a month. Mark my words.”

She was so certain it terrified me. She wasn’t guessing. She was warning me how this ends.

“Now,” she said. “What are we going to do about that little problem between your legs? Have you ever stayed hard this long without touching it?”

“I don’t think so, Miss Harlow.”

“You want to touch it, don’t you?”

I wanted to, but wasn’t sure if I should admit it. I thought back to a porn clip I’d seen online and dug for an answer. “If it pleases you, Miss.”

She laughed. “Well done, Timmy. But what if it doesn’t please me? Then what?”

In all the porn I’d watched, no one ever asked that. I was on my own. “I… I don’t know, Miss Harlow. Nothing. If it won’t please you, then nothing. I’ll do nothing.”

I was repeating myself, saying it twice like I was the one who needed convincing, not her.

“Well, it won’t please me. Amuse me, maybe, but definitely not please me.”

She was no more than a couple of feet in front of me, staring into my eyes, daring me to blink first. The contrast didn’t make sense. I was rich. I was powerful. But inside this room, I was nothing and she was everything.

I didn’t realize it at the time, but everything I’d said during intake and on the questionnaire, all of it was fantasy. This was real. In one short session Miss Harlow had broken me down. All she had to do was stand there, confident in a way I could fake at work but not here, not in this room, not when I was naked with her staring me down.

“Go on then,” she said. “Give it a tug.”

“Thank you… Thank you, Miss Harlow.”

I started stroking, and it hit me how exposed I felt. She watched every move I made. She knew I wouldn’t stop, and the longer it went on, the more I slipped into whatever she wanted me to be.

“Look at you,” she said. “A half hour ago you couldn’t get your tie off, and now you’re standing there with that little thing in your hand, beating off for a woman who would never fuck you. Whatever dignity you thought you had… It’s gone, isn’t it?”

“Yes, Miss Harlow, it is.” She was right, but it wasn’t enough to make me stop.

“At work, people scramble when you walk in. They’re afraid of you.” She placed her hand lightly at the base of my throat, not threatening, just proving a point. “Do I look afraid of you, Timmy?”

“No Miss Harlow, you don’t.”

“Of course I’m not. I own you now.”

I was on the edge. I tried to slow down, but couldn’t.

“Even that disappointment in your hand, that’s mine too. It’s useless, I don’t want it, but I own it.”

I was going to cum. I could feel it happening. I hadn’t even considered where I would finish. I was so desperate I hadn’t thought past the next stroke.

“I’m going to cum Miss Harlow.”

“You’re mine now. Call me Mistress Harlow.”

“I’m going to cum Mistress Harlow.”

“No you’re not. I told you to stroke. I didn’t tell you to cum.”

“Please Mistress Harlow.”

“No. This isn’t one of those situations where you beg and I change my mind. The answer is no. And it stays no.”

It killed me to pull my hand away, but I wasn’t about to find out what she’d do if I didn’t. My knee buckled and I dropped to the floor. I pinned my hands to the ground. If either hand moved, I’d start again.

“Don’t you dare make a mess on my floor,” she said from above me. “If even a drop dribbles out, you’ll lick every tile clean.”

I was on my hands and knees in front of her. From where she stood, it must have looked like I was worshiping her. Maybe I was. Maybe this is how it starts.

She gave me a few moments to recover, then crouched down beside me.

“This was a good first session.” She patted my head like I was a new pet. “Rule number four. No cumming. Not in my office.”

She stood again and brushed off her hands. “If you need to finish yourself off, there’s a washroom down the hall. You have my permission. Get dressed first.”

She sat behind the desk while I pulled my clothes together, still hard and embarrassed.

“No more escorts,” she said. “No dating.”

“Yes, Mistress Harlow.”

“My assistant mentioned you were curious about chastity.”

“I… yes, I did, I am, Mistress.”

“Good. That will come later. For now, you text me if you want to masturbate. Wait for my answer. And you keep your hands off until I tell you.”

“Yes, Mistress. Thank you.”

She came around the desk and placed her hand at the small of my back, guiding me toward the door. It felt like the way a man might guide a woman.

“You were nervous,” she said, “but you did well. I don’t take everyone on. I’m choosing you because you’re workable.”

“I won’t let you down, Mistress.”

“I know. Now go.”