Spanking My Secretary - Cover

Spanking My Secretary

Copyright© 2022 by Lubrican

Chapter 10

Romantic Sex Story: Chapter 10 - 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  

They did sleep over. When Mandy and I got in bed she was acting reserved. I knew what happened had impacted her forcefully. Instead of engaging in foreplay, I decided to talk, instead.

“You okay?” I asked.

“I don’t know,” she replied.

“Cynthia seems to have taken it pretty well.”

“Yes. Or she’s pretending to take it well.”

“I don’t think she’s pretending. If she was upset she’d have wanted to go home, don’t you think?”

“I don’t know. I don’t know anything anymore,” she sighed.

“I think I was right,” I said. “I think it was a catharsis for you. I’m kind of glad it happened.”

“Bob, I lost control! I was beating you! I was trying to cause you pain!”

“Well, you succeeded in that,” I said, grinning.

“Is that how they felt when they hit me?” she asked.

“I don’t know. The professor, probably not. Barry, maybe yes.”

“But you don’t feel like that when you...” She didn’t finish.

“Not even a little bit,” I said. “I try to only give you what you think you need. I never get angry.” That was a lie. I knew I’d gotten angry several times, but that was too complicated to try to discuss now.

“I don’t know what to do, now,” she said.

“C’mere,” I said.

I pulled her against me and kissed her hair.

“Just be you,” I said. “Your daughter loves you. I love you. Just be the woman we both love.”

We lay there, naked, but neither of us felt any lust. We were just there, holding each other.

Eventually we fell asleep.


What happened that day had a lasting impact on Mandy, of course. Her depression about it passed, probably because Cynthia, with the flexibility of youth, acted like it had never happened. She just acted like ... Cynthia.

Mandy’s reaction wasn’t visible, exactly. She pulled back a little. At work she didn’t tease me. She still did her work flawlessly. I was able to concentrate on my job better. The following weekend she asked me to take her car shopping. We found a used, three year old Volvo that she felt was too expensive, but I said I’d kick in some money on it.

“It will be our car,” I said.

She stared at me for what seemed like forever.

“No strings,” I said. “You need a car you can depend on. I need an executive assistant I know can get to work and go pick up my dry cleaning and all that. This car makes sense. That’s all this is.”

“What if you break up with me?” she said. “What happens to the car, then?”

“I’m not going to break up with you. Are you thinking about breaking up with me?

“I’m thinking this relationship is too good to be true,” she said. “You know what they say about things that are too good to be true.”

“That’s not an infallible thing,” I said. “Why rock the boat?”

“This boat rocks a lot,” she sighed.

“Are you happy?” I asked.

“Yes.”

“So am I,” I said. “Do you think Cynthia is happy?”

“Yes.”

“Well, then, we all have our sea legs and it doesn’t matter if the boat rocks now and again.”

Mandy walked around the Volvo again. She opened the back door and peered inside. She turned back to me.

“Does that back seat look big enough to have sex on?”

“Cynthia won’t be using this car for three or four more years,” I grinned. “I don’t think you need to worry about that now.”

“I wasn’t thinking about Cynthia,” she said. “I was thinking about whether I could celebrate getting a new car.”

“Oh!” I said. I looked in the back. “I think it might work.”

“Okay then. I’ll buy this one,” she said.

We couldn’t celebrate right away, because I had my car and she was driving her car. She took it to her apartment building and found there was somebody else’s car in the spot that had her number on it. Since she had not been using that space, a squatter had moved in. She had to park in a guest spot and wouldn’t be able to talk to the manager until Monday. I parked next to her and we went into her apartment to find a note from Cynthia saying she was at Becky’s house. There was a phone number on the note.

Mandy didn’t call.

Instead we celebrated her new acquisition in bed.

“We’ll have to try this in the car, later,” she panted, as I lunged into her.

“Yes, Ma’am,” I grunted.

“I never got to do it in a car when I was younger,” she gasped.

“Beep, beep!” I groaned, as I jetted into her scorching depths.


The weather got warmer. “The incident” faded into the past. We went places as a “family”. We went to the Blank Park Zoo one day. On another we visited the state historical museum and then walked up to the capitol building. I took pictures of them. Cynthia took a shot of her mother and me standing, my arm around her.

Another big contract offer came up and my boss wanted me to travel to Kansas City to present it to the client. I took Mandy with me. This time she booked two rooms across the hall from each other. Nobody stayed in her room. We were strictly professional during the presentation, and then, that night, acted like we were married. We got that contract, too, and I got another bonus.

On the 4th of July we went to Riverview Park and listened to a concert before fireworks filled the sky. The following weekend I took them to Jester Park and we went horseback riding. The weekend after that it was renting a Hobie sailboat at Big Creek Lake and trying to learn how to sail. The boats are catamarans and impossible to sink. They’re easy to run aground, though, when you can’t figure out how to get the wind to take you where you want to go. We had fun, though.

And two or three times a week, and every weekend, Mandy and I made reckless, dangerous, unprotected, bareback love.

It was bound to catch up with us.


It was a Tuesday morning after we had rented a motorboat at Saylorville Lake when Mandy came into my office and stood, submissively in front of my desk, head down and hands clasped in front of her groin. I knew this pose well, by now.

“What did you do now?” I growled. Over the last six months I had “disciplined” her less and less. She now preferred to make love, instead of feel guilty and seek punishment. This is not to say she abandoned her proclivity for occasional pain. I still reddened her ass once or twice a month. She had not asked me to spank her clit, though.

She lifted her head and looked at me. This was uncharacteristic and I felt the hair stand up on the back of my neck.

“I think I’m pregnant,” she said, softly. “I mean I might be pregnant. I should have had a period and ... I haven’t.”

My heart thudded in my chest. I’m ashamed to say the first thing I thought of was I was going to lose her as my executive assistant. The bosses would never let her stay with me and appear in public when her belly swelled. She’d get assigned to some menial tasks, like filing or records retrieval or something like that, until she had the baby and had regained her figure. They would say it was to ensure she didn’t get overstressed during her pregnancy, that it was for her comfort and safety, but it was basically a watered-down form of misogyny.

Only after I’d had that selfish little detour did the road come back to “I’m going to be a father!

Wow!” I said.

“Wow? This isn’t good, Bob,” she moaned.

“Stop right there!” I barked. “Unless you want me to bruise your backside, you need to pull back from saying things like that.”

“Bob, I can’t afford to have a baby!” she yipped.

“You act like you’re in this alone,” I said, gravely. “Now you have committed two infractions for which I’m going to have to paddle you. You’re not in this alone, Mandy. Don’t be ridiculous.”

“What can you do about it?” she argued. “They’ll reassign me. You know that and I know that. You’ll have a new secretary.”

I stood up.

“You’re fired,” I said, gravely.

“What?” She sounded confused.

“Well, you’re not fired just yet, but as soon as you start to show, you’re fired. They will not be reassigning you, because I’m going to fire you.”

“You can’t do that!” she wailed.

“Pipe down!” I growled.

“Why would you fire me?” she whined.

“Because I can’t marry you if you’re employed here,” I said. “By the way, will you marry me?”

Her eyes got huge. Her mouth opened and closed several times, but she didn’t say anything.

“Okay, okay, you can think about it before you give me my answer. Just don’t think too long, because when you start showing I’m going to have to do something. I will not have you working in the basement, out of sight and out of mind. Instead, I think you can work at home, raising a family. My income will easily support us. You need to spend more time with Cynthia, anyway, right?”

“What will Cynthia say?” moaned the future mother of my child.

“She’ll complain that she has to babysit while we go on dates,” I said.

“What if she complains about you?”

“I’ll talk to her. You just worry about going to the doctor and doing all that stuff pregnant moms are supposed to do.”

“So ... you... want ... this baby?” she whispered.

“It’s a package deal,” I said, firmly. “It includes you, Cynthia, and Junior, in there.” I pointed at her midriff.

“Okay,” she said, weakly.


Of course the rest of the workday was lost. I couldn’t concentrate on anything. She called her doctor, but couldn’t get in for another week. I followed her home and found Cynthia doing her homework at the kitchen table.

“Go for a walk with me?” I suggested.

“A walk? Where?” responded the girl.

“I need to talk to you, in private,” I said.

“Okay,” she said. “There’s really nowhere to walk, though.”

“We’ll manage.”

She followed me outside and we walked toward the end of the block.

“You know how, in the old days, a man would go to a woman’s father and ask for her hand in marriage?” I said.

She stopped.

“Your mother doesn’t have a father for me to ask,” I said. “So I figure it’s your job to take his place.”

“You want to marry my mother?” her voice was higher than usual.

“Desperately,” I said. “I love her and she loves me. We’ve been doing this ... whatever it is we’ve been doing ... and I want to make things permanent. I told you I’d talk to you about it if this ever hapened. It’s happened and now I’m talking to you about it.”

“I wondered if this would happen,” she said.

“You’d have to come live with me,” I said. “I don’t think all my stuff would fit in your apartment.”

“You’re funny,” she said, her voice dry. “Would I have to call you Daddy?”

“Nope. Like I told you before, I’ll never try to be your father. Somebody else already nabbed that title.”

“But you will be my dad ... sort of.”

“I think they call it step-dad,” I said.

“Hmmm. Did you ask her already?”

“Well, sort of. I didn’t so much ask her as I told her she had to marry me or I could never be happy again.”

“Gee, that’s not very romantic. It’s like you’re trying to guilt her into it.”

“I told her to think it over. You can do the same thing. Maybe you two should talk it over.”

“Ya think?” Once again I was astonished at how maturely this girl processed unexpected, intense situations.

“I’ll just go home, now,” I said. “Thank you for listening to me.”

“You know, sometimes you can be one of the weirdest guys I ever met,” said the teen.

“Gotta love me,” I quipped. “Especially if you let me marry your mom.”


I probably should have told Cynthia her mother was pregnant when I asked her to let me marry her. That little bit of information might have affected how she thought about things. But that was also a very personal bit of information that I thought her mother might want to share herself, and that me talking about it first would have been like poaching an endangered species.

I did leave, so that they could talk about me (and, presumably, the baby) and I found out how Cynthia felt about the fact I’d left out important information the very next day – at work!

Mandy had recovered her composure and looked as cool and gorgeous as ever in a slate grey skirt suit over a silver silk blouse. I’d been there since six-thirty because I woke up early and couldn’t go back to sleep. By “early” I mean four A.M. I was too keyed up. I had actually been working when my office door opened and the vision of loveliness who was my executive assistant breezed in with my morning coffee. I’d already had two cups by then, but who’s quibbling. I looked up at her with hope shining from my face.

“Good morning ... Sir,” she said, formally.

“Good morning. Do you have something to discuss with me?”

“No, Sir. Not yet, Sir,” she said, her inflection unchanged from her earlier greeting.

“Not yet?” I know I sounded like a pouting little boy.

“Cynthia says your conversation got cut short and she’d like to finish it before you and I ... talk.”

“I didn’t think it was cut short, exactly,” I complained. “I assumed it would recommence at a later date.”

“Well, she feels like you apparently left out an important aspect of the situation.”

“You mean I didn’t tell her about the baby. Of course I didn’t tell her. That’s your job. Well, not job, exactly. More like privilege.”

“Oh, I did feel quite privileged to impart that as we discussed whether or not I should change my social status on such a radical level.”

Her tone now was neither cool nor relaxed and I sensed trouble in paradise. I did not, however, want to unpack that trouble at eight-thirty in the morning and possibly set a dismal tone for the rest of the day. I could wait eight hours to have that conversation. And I could talk to Cynthia, then, too.

I didn’t have to wait eight hours. At ten-thirty Cynthia marched into my office like an angry client, bypassed the guardian of the portal – her own mother – and slammed open my office door, before slamming it closed again.

Okay, actually, she didn’t slam anything. She was just forceful about things and I wasn’t prepared for it. Neither was her mother. I blinked at the girl, as if she might be something in my imagination, and could be erased by my eyelids, and then saw Mandy get up from her desk. Cynthia was too quick for her, though, and turned to lock the door. Then, as if she had been there before, she went to the windows that faced the rest of the office and fumbled with the blinds, closing them, before turning to face me.

Her face was red and she was breathing hard.

“You prick!” she spat. “You could have told me!”

The door knob rattled and there was a discrete tap at the door.

Go away!” said Cynthia, much too loudly.

“Cynthia,” I said, placation heavy in my voice.

“Don’t you Cynthia me, you piece of ... dung.” At least she paused to moderate her choice of words. It was clear Mandy had taught her not to use foul language. Her alternative use of “penis” had apparently slipped by. “You could have told me you knocked my mother up before you begged me to give you my blessing!”

“No, I couldn’t,” I said. “It wouldn’t have been fair to her to usurp that privilege. It’s her body and she has the right to decide who to tell and who not to,” I argued.

The door knob rattled harder. We both knew who was doing the rattling. Cynthia ignored it.

“Privilege,” she snorted. “I don’t think she thought it was a privilege. She broke down and cried for two hours! I was afraid I was going to have to call an ambulance because she was so worked up!”

“I’m sorry,” I said. “I thought we’d kind of talked that out and she was okay with it.”

“Sure, she’s okay with you knowing,” snarled the angry teenager. “You’re the one who did it to her. But you never thought about how then she’d have to admit to me that I’m going to be a big sister who’s fourteen years older than her sibling, and how our family will be turned upside down by a squalling little baby, and how I won’t be able to concentrate on my homework because of the noise and bustle and how just everything will change!”

“I don’t think it will be that bad,” I said. “Babies don’t cry twenty-four hours a day.”

The girl paced. I wondered why Mandy wasn’t knocking, still, but my question was answered as the door knob smoothly turned and Mandy came in, holding her key to my office. She closed the door hastily and faced her daughter.

“What are you doing here?” she gasped. “Why aren’t you in school? How did you get here?”

“I skipped, Mother,” said Cynthia, icily. “I called a cab. And why do you think I’m here?”

“I said you could talk to Bob later,” said Mandy.

“Well, this is later,” grumped Cynthia.

“Ladies, could we take this discussion somewhere else?” I suggested.

“Why? Are you ashamed for people to know you got my mother pregnant?” asked Cynthia. Her volume wasn’t quite a yell, but it was loud enough that people outside could tell her voice was raised.

“No, I am not,” I said. “In fact, I’m proud she’s going to have my child. What I’m concerned about is that she – or I – might get fired because of the manner in which people find out. This is a professional office and the people who have the authority to fire both of us expect things to run smoothly, without any shouting matches. Now, I get it that you’re angry with me. That’s fine. You can be as angry as you like. But don’t let your anger affect your mother’s situation. She needs this job until other arrangements can be made. I, personally, would prefer that she resign and become a stay-at-home mom. That’s her decision, however. I personally, would prefer that she marry me and doesn’t even need to work, but again, that’s her decision. And yours, if I remember. So I, personally, would like to go somewhere other than here to have this discussion because I’m dying to find out what’s going to happen and here is not the place to do that.”

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