Spanking My Secretary - Cover

Spanking My Secretary

Copyright© 2022 by Lubrican

Chapter 2

Romantic Sex Story: Chapter 2 - My secretary took home an almost finished project to do the final prep on it and it got destroyed. When she confessed about it the next day I knew it wasn't really her fault, but she was miserable about it. When I threatened to spank her I meant it as a joke but she didn't take it that way. She said she SHOULD be punished and would submit to my discipline. It turned out to be my entry into a world I'd heard of, but had never dreamed I could enter... and enjoy.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Reluctant   Fiction   Workplace   DomSub   MaleDom   Spanking   Oral Sex   Petting   Pregnancy  

Mandy went to the bathroom to compose herself (and presumably let my semen drip out of her over the toilet). Dressed again (with her panties in her purse instead of back on her body), she looked completely normal. If I hadn’t known better I would never have believed she’d just been fucked and bred. She was composed and acting just like she had every day since she started working for me.

I still didn’t understand this new kind of relationship I found myself in, so I didn’t know exactly how I should act, myself. I opted for compassion. Whenever my dad used to take a belt to me, after it was over he always told me he loved me. He made it clear that, while punishment for sins was done, it didn’t mean love died.

I put my hands on her shoulders and made her face me. Her eyes went to the top button of my shirt.

“Look at me, Mandy,” I said.

Her eyes lifted.

“You okay?” I asked.

Her eyes widened, but she nodded.

“You needed that?” I said. I made sure the question was clear in my voice.

“Yes, Sir,” she replied.

“Well, in light of things ... it may be necessary for me to punish you in the future,” I said.

“I know, Sir,” she said. Her eyes dropped to my top button again.

“If my punishment methods are too harsh, I can get you transferred to another boss,” I said. I held my breath, waiting for her response.

“That won’t be necessary, Sir,” she said.

“Are you sure about that?” I asked. I had, after all, shot off in her fertile pussy.

“Positive, Sir,” she said.

I figured I’d just talk about the elephant in the room.

“If I keep having to punish you, and you’re not on birth control, there could be complications,” I said.

“I can’t afford birth control, Sir,” she said. “It isn’t covered by our medical insurance.”

“I can pay for your birth control,” I snorted.

Again, she looked up at me.

“If there are ... complications ... then I deserve them,” she said.

“You’re kidding,” I blurted.

She blinked, but didn’t look away.

“No, Sir.”

I was stunned. She had basically said she’d let me knock her up. She was already struggling, financially, so how could she accept that kind of... “punishment”?

“We’ll talk about that later,” I said. “For now you are forgiven. We’ll get caught up on the project and everything will be back on track.”

“Yes, Sir. I’ll work hard to get it finished.”

I called her a cab and it was awkward while we waited until I said I should check her bruises. She promptly put herself over the back of the couch and pulled her skirt up. I worked some more lotion in and then we heard the honk from the cab outside. I had the urge to kiss her, but that felt wrong somehow.

“I’ll see you tomorrow, bright and early,” I said, as she walked out the door.

“Yes, Sir,” she said, looking over her shoulder at me.

For the first time there was some emotion on her face.

Her eyes were smoky, and her lips pouted just a little.

“Thank you, Sir,” she said, meekly.


Now, I’ve been on the merry go round of sex a few times. I like the ride. I’ve ridden a ‘horse’ and a ‘zebra’ and a ‘lion’ before. I’ve even ridden just sitting on the bench as it goes round and round. But the music was generally the same, even if the women were very different. As I lay in bed that night, though, I realized Mandy wasn’t like any other woman I had ever fucked. I know my attitude about all this might seem cavalier, but the fact is I like there to be some romance involved with a woman when I take her to bed. If there’s not, then I’ve been known to back off. Sex without the romance isn’t much better than just jerking off.

So I was confused about Mandy, because there hadn’t been anything romantic about our coupling at all, at least not while it was going on. And there hadn’t been any romance or chemistry before I took her home, either. There had been no flirting or innuendo at work. I hadn’t even taken her out to dinner first. And yet, somehow, I felt like something important had just taken place. With the others it had just been some fun between the sheets. None of those other types of women on the merry go round had really needed me.

Mandy had needed me. She had really needed what had happened, even if I didn’t understand why. And she had actually chosen me to help her. I wasn’t just some Joe she’d stumbled on. She hadn’t just said, “Hey, Mister, want to beat my ass and fuck me? I kind of want that to happen right now.”

The romance had been in that last look she gave me. There had been something in her eyes and her “Thank you, Sir,” had been heartfelt. She really had been thankful that she was going home with a bruised butt, and that I was the one who bruised it.

I had never been involved with a romance like this. I didn’t know how to be in a romance like this.

That’s what I was thinking about as I went to sleep that night.


She was already there when I got there the next morning. My coffee was ready and she acted exactly like she had every day previous to that.

The first thing I did was give her a raise. Well, got it for her, actually. I didn’t tell her about it. I went to HR and found out she was actually being paid three grades lower than her time with the company entitled her to. She had not taken any courses or tests. Routine paperwork (by a boss who gave a shit) had been ignored, even before she worked for me. HR didn’t feel compelled to inform me of this and I seethed a little.

Back in the office we worked on finishing the project. Nothing whatsoever was said about the previous day, or the fact that I’d fucked her socks off before dumping my DNA in her fecund womb.

We were finished on time and the presentation went better than I had hoped for. The VP was delighted.

I decided to give credit where credit was due.

“My executive assistant was invaluable in getting this ready,” I said.

“Then take her with you when you go,” he said.

“Go?” I asked.

“I want you to go to New York to seal the deal with the contractor,” he said. “I’ve already talked to their CEO and you’ll have to meet with department heads of various parts of the company. It shouldn’t take more than three or four days. This could produce millions in revenue for the company, Bob, so make sure we get that contract.”

“Yes, Sir,” I said. “I won’t let you down.”

Back in my office I pushed the button that called Mandy from her desk on the other side of a glass wall that closed in my office. When she came in there was interest plainly etched on her face.

“How’d it go?” she asked, foregoing the rigid politeness she was known for.

“It went well. What kind of provisions do you have for being away from home for a few days?”

“Sir?” She was plainly taken off guard.

“The VP wants me to go to New York to finalize this contract and he told me to take you with me.”

“He told you to take me with you?” She was clearly unnerved.

“I told him you were indispensable in the preparation for the presentation. He said for me to take you with me so that we get that contract. We’ll have to meet with a number of department heads and there will probably be social events to attend,” I said.

“What would I be required to do?” she asked, looking worried.

I knew why she looked worried. It wasn’t unheard for girls to be taken on trips to use as bribes to get contracts. That was a fairly common practice in big business deals.

“You’re not a whore, Mandy,” I said, bluntly. “This will be a straightforward contract negotiation and you will be my executive assistant, nothing more.”

“Thank you, Sir,” she said, looking clearly relieved.

“Unless you screw up,” I added. “If that happens, I’ll have to punish you, of course.”

She looked wary again.

“Punishment, should it be required, will not involve anyone but you and me,” I said. “Nobody will touch you without my express permission, and I do not intend to give that permission unless you ask me to.”

“I won’t ask you to,” she said, followed by a clipped, “Sir.”

“Good. So, what about Cynthia?”

She frowned. She even looked beautiful when her forehead was creased.

“Mrs. Hudson might be willing to let them have an extended sleepover,” she said. “I should pay her, though.”

“I got you a raise,” I said. “You’re getting almost twice what you were being paid. Paying this woman shouldn’t be a problem.”

“Sir!” she barked. “I didn’t ask for a raise!”

“Calm down,” I said. “This has nothing to do with your punishment. If anything, it has to do with the fact that you normally do excellent work. I discovered you should have had two raises before you ever came to work for me. All I did was correct your previous supervisors’ negligence. You were due raises and didn’t get them. So I corrected that. This doesn’t mean I require anything from you other than continued excellence in your professional life.”

I saw the glint of tears in her eyes.

“Thank you, Sir. This will really help.”

“Just make sure you don’t screw up,” I growled. “I’d hate to have to punish you again.”

“Would you, sir?” Her voice was, for the first time ever, a little teasing. I was really surprised.

“I will happily paddle you until you can’t sit down, if you deserve it,” I said, menacingly.

“Yes, Sir,” she said. She looked like she was hiding a smile.

I realized that our relationship had just changed, somehow, become less stern and strict. I wasn’t sure how to feel about that.

Basically, I wasn’t quite sure how to feel about Mandy Potemkin.


What I didn’t think about during all this, that’s been described thus far, was that Mandy became my partner in excellence. I’m not joking. My last executive assistant had been quite competent, but only did what I tasked her with. Now that I looked back at things, I was like Mandy with that woman. I walked everywhere I went. Mandy went above and beyond her routine duties. I knew what to do, in terms of business, but she was like the car that got me to work each day. If I hadn’t had that “car” it wouldn’t have mattered how smart I was, business wise. I wouldn’t have gotten to work to use all my smarts. If you want more examples then think of cell phones and microwaves. My mother got along just fine without either when I was growing up. Any mother who tried to do that these days would be at a serious disadvantage, compared to her more technologically accepting sisters.

Well, I suppose not if she was Amish, maybe.

But I’m not Amish and the cell phone, microwave, and car in my life that was Mandy made a huge difference in how things went for me. I never thought about that while I was getting to know her, and while she was becoming something I couldn’t live without. She didn’t, either, except she recognized how indispensable she was long before I did.

She booked the tickets and hotel as usual, except this time she did it for two, rather than just me. I thought it was interesting that, when we got to the hotel, there were two rooms waiting for us, next door to each other. There was a set of double connecting doors between them. You could unlock the one on your side, but if the person in the other room didn’t unlock theirs, then there was no going back and forth between the rooms. It looked very professional and appropriate, without any hint of hanky panky. I wondered, for the first time, if I could order her to do things – things outside her professional duties – without the excuse of punishing her for some misdeed.

I decided not to push the envelope to find out. Fucking her had been pretty amazing, and I wanted to do it again. If I broke some mysterious rule in this new kind of relationship, I didn’t want to suffer for it. Better to wait. She’d do something wrong, eventually. All of us eventually do something wrong.

The bell boy hauling along the cart with our bags on it stood, waiting for me to open my door while Mandy stood beside him.

“Which bag is the proposal in?” I asked her.

“There are two copies, one in your blue bag, and one in one of my bags,” she said. “Except for the posters. There’s only one set of them.” I glanced at the portfolio art case she’d carried onto the plane and which she hadn’t let out of her sight since.

Good girl. She wasn’t taking any chances this time around. I looked at my watch.

“I’m going to take a shower and change clothes.” I looked at the bell boy. “Is the restaurant downstairs any good?”

He smiled.

“I’m paid to tell you it is, but in this case it would be the truth anyway. I’m told the lasagna is to die for.”

“Just told?” said Mandy, suddenly. “Haven’t you tried it?”

“I just deliver bags and show people around,” grinned the young man. “You don’t eat in our restaurant on those wages.”

“You’re fishing for a tip,” said Mandy.

“Mandy!” I snapped. “Of course he’s fishing for a tip. It’s part of his job description. Don’t be impertinent.”

She looked down at the floor instantly and flushed.

“Yes, Sir. I’m sorry, Sir.”

I pulled out my wallet and reached in to find one of ten fifty dollar bills I’d had Mandy put there. I dropped it into the young man’s suddenly outstretched hand and said, “Try the Lasagna. I hear it’s to die for.” I grinned and went inside my room. I went directly to the bathroom, knowing that Mandy would have him put my bags on the bed, or wherever, and she’d have a change of clothes laid out for me when I got out of the shower.

While I was in the shower I wondered if that connecting door would be open when I got out. I got hard thinking about it. I decided to jerk off in the shower. I didn’t want to be on edge because I was horny and unable to do anything about it. I thought about punishing her for being rude to the bell boy, but if she didn’t really see that as an infraction, that might backfire. For this to work, she needed to feel bad about something and, for all I knew, this was the first bellboy she’d ever engaged with. She was a small town girl who had gone to a small state university, where an unethical professor had dominated her. It was unlikely she was familiar with the lifestyles of those who were on the fringes of the rich and famous.

I had no idea she apologized to the young man when he took her to her room. I had no idea he said it was fine, but that fifty bucks would only get him an appetizer in the hotel restaurant. And I had no idea she had him show her how to open the connecting door (he had a tool that undid mine from her side) so she could get back into my room, where she got into my wallet and gave him two more fifties. He was a “little person” too and she understood exactly what the challenges of his life were likely to be about. She also made a friend in the process, even if he’d be a short term friend she’d never see again when we went back home. I only made friends with people I thought could provide me some advantage.

Mandy made friends because she liked having friends. It was her friends who had gotten her through the travails of college, and then the travails of being a single mom.


When I got out of the shower, sure enough, there was a casual outfit laid out on the bed, including socks. There was no underwear laid out because she knew I didn’t wear any. The rest of my clothes had been put away and my suitcase was stowed on the little stand designed for that purpose. It was five-thirty, a little early for dinner, but I called Mandy and asked if she wanted to have a drink before we ate.

“I’m not so good with alcohol, Sir,” she answered.

“You can drink something virgin,” I said. “I’d like some company.”

“Whatever you say, Sir,” she replied.

I told her to go on down and wait for me in the bar, and that I’d be there after I made a call. I raided the little fridge in the room. There wasn’t any decent Scotch, but there were two airline bottles of Jack Black, so I drank them while I dialed the number of my vendor contact to let him know I was in town.

“Your assistant already called me,” he said. “Did you get your signals crossed?”

“She’s in her own room,” I said. “I haven’t gotten a chance to see if she took care of things.”

“Well, she did. I’ll pick you up at eight in the morning. Now, I’d like to get back to eating supper with my family.”

“Absolutely. Go,” I said. I hung up miffed again. The guy was a jerk. Not only that, he was a low level jerk, most likely. You don’t run a multi-million dollar business and then send somebody important to pick up someone trying to sell you a service.

I was still feeling surly when I got to the restaurant and looked for Mandy at the bar. She was there, sipping some kind of fruity looking drink in a martini glass. There was a guy invading her personal space, leaning in enough that she was leaning away from him. I walked over and stood within inches of both of them.

“I hope you’re not bothering my date,” I said.

The guy looked over at me and I recognized the bleary eyes of a man who started drinking way too early in the day.

“Fuck off,” he slurred. “I saw her first.”

“Actually, you didn’t,” I said, politely. “I got her a room here and she’s having dinner with me, tonight. What you did is push yourself on a young woman who has better taste than to put up with the likes of you.”

I saw the belligerence in his eyes and silently chastised myself. I was pushing it with him because I was angry with some flunky who just wanted to have supper with his family. I am six-two, however, and I do work out at the gym three days a week. I also wear tailored clothes, because I like looking like I wear tailored clothes. The guy might have already had one too many, but he wasn’t so drunk he missed the potential for things not working out well for him.

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