Spanking My Secretary - Cover

Spanking My Secretary

Copyright© 2022 by Lubrican

Chapter 7

Romantic Sex Story: Chapter 7 - 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  

It turned out that Cynthia advanced things for us. I met her the first time when I picked up Mandy to go to dinner. Cynthia turned out to be a bright, happy girl who was actually happy that her mother had decided to start dating.

Mandy was still getting ready, when I arrived and Cynthia let me in.

“You must be special,” said the girl, examining me. “My mother has never gone on a date before.”

“Is that okay with you?” I asked.

“Yes, assuming you’re a nice guy,” she answered.

“I will try my very best to be a nice guy,” I vowed.

After two “dinner dates” which were actually at my house, in my bedroom, Mandy asked her daughter if she wanted to go bowling with us.

She did, but it was obvious to me that Cynthia’s motivation had less to do with knocking pins down than finding out more about me.

“You’re my mother’s boss, aren’t you?” she asked, while Mandy was throwing her ball into the gutter.

“That’s true,” I said.

“So what are you guys like at work?”

“We keep things pretty professional there. Your mom is very good at what she does.”

“You two went to New York, that time, right?”

“Yes.”

“And you stayed in the same hotel?”

“Yes.”

“Did you fool around?”

Mandy came back to the observer section and complained that she was no good at bowling.

“To be continued,” I said, as I got up.

“What’s to be continued?” asked Mandy.

“I just asked him if you two fooled around in New York,” said Cynthia, with no embarrassment at all.

“What?” Mandy gasped.

“Well, you obviously like each other. Don’t you think I should know if you’re doing that kind of stuff?” asked the girl, boldly.

“I need to go bowl,” I pointed out. “Why don’t you two talk while I do that.”

I took my time, lining up my shot. I paid attention to my stance, where my feet were in relation to the little arrows on the floor. I was careful to step off smoothly and swing properly and all that. I knocked down two pins. When I got back they had their heads together.

“You’re up,” I said to Cynthia.

“In a minute,” she said.

“Let’s finish up this line and then we can get something to eat and talk,” I said.

Cynthia got up and took just as much time as needed to lift her ball and launch it down the lane. She got a strike, which was why I had time to ask Mandy what had happened.

“She asked me if we had sex, yet,” moaned Mandy.

“What did you tell her?”

We paused to clap for Cynthia’s strike.

“You came back before I had to answer.”

Cynthia’s ball came back and she picked it up.

“What are you going to tell her?” I asked.

“I don’t know. I can’t just admit that I hopped in bed with you. Right?”

Cynthia knocked down seven pins and stood, waiting for her ball.

“You said she’s sharp. She’s going to figure it out sooner or later. Why not just be honest with her?”

We watched as Cynthia threw her second ball. She missed the three remaining pins and turned to walk back to us. She stood, just looking at us.

“I’m not dumb, you know,” she said.

“We know that, Sweetheart,” said Mandy. “It’s just difficult for adults to talk about that stuff with a child.”

“I’m not a child, Mother,” said Cynthia, sternly. “I know what happens between boyfriends and girlfriends.”

“You’re thirteen,” said Mandy. “By definition you’re a child, whether you want to be or not.”

“Let’s not get in an argument, here,” I said. “We can come to some agreement about having an age-appropriate conversation.”

“All I want to know is if you’re doing it or not,” said Cynthia.

“Why?” asked Mandy.

“Because if you two are having sex then that means you like him more than any other man and that means he might be around a lot. Right now he’s just your boss and some guy you decided to date, but if he’s going to be around a lot, that’s going to affect me, too.”

“Can I ask a question, here?” I queried.

Both women looked at me.

“Yes,” said Cynthia.

“What if I was around a lot? How do you think that would affect you?”

“I’d need a better set of headphones, for one thing,” she said.

“Headphones?” asked Mandy.

“Yeah, so I could listen to music or play video games while you two make a lot of noise.”

“Oh,” I said. “That’s pretty innovative.”

“My friend, Sharon, told me that’s what she does when her parents get all lovey dovey.”

“Headphones,” I mused. “I could get you a really nice set.”

Bob!” moaned Mandy.

I looked at Cynthia.

“Your mother and I like each other a lot,” I said. “Does that answer your question?”

“Yes. Thank you,” said the girl.

“So you don’t mind that we like each other?” I asked.

“You seem like an okay guy. But I’ll be watching you.”

“A sensible stance,” I said. “I hope you’ll always tell me what you think.”

“So, are we going to finish this game or what?” asked Cynthia.


There was no magical transformation in our lives or relationship. Cynthia didn’t run to hug me every time I came over, or sit on my lap and say, “I wish you were my daddy.” It wasn’t like that at all.

What did happen was that every time I went over I managed to find a few minutes to talk to the girl. I didn’t ask her how her day went or what she’d learned in school that day. Rather I asked for her opinion on various things. Usually it had to do with something I heard on the radio as I was driving to their house. I listen to NPR, which covers a wider spectrum of events in their news programs, so I always had something to talk about.

An example might help. I heard a story one time about how the tradition of Japanese people to hunt and eat whales was in conflict with current ecological programs to protect the animals. It was noted, in the story, that Japan has very little land mass on which to grow crops, hence their dependence, historically, on getting their food from the sea. So when I got there and Cynthia told me her mother would be ready in ten minutes or so, I asked her what she thought about the Japanese situation.

“They can find something else to eat,” she said, firmly. “They can buy food from other countries.”

“If you buy food, you have to have money to buy it with,” I said. “If you get your food from the ocean, it’s free.”

She looked at me and put her hands on her hips.

“If they keep killing whales, then whales will become extinct, and they’ll stop eating them for sure, then,” she said. “So why not stop eating them before they go extinct?”

“You have a point,” I said. “The problem still exists, though. Anything they supplement with will still have to be bought or traded for.”

“I have a friend at school named Luis,” she said. “He and his dad are Mexican. I’m pretty sure his dad’s illegal, but his dad sends money back to Mexico every month to support some people there. Japanese people could go to other countries and work to get money to send home to buy food.”

Her solutions to most problems were typical of what a twelve or thirteen-year-old in America would come up with. Most were very simple answers to very complicated problems. It’s why we don’t let people that age vote. But they were good conversations and I had a surprisingly good time engaging Cynthia while we solved all the world’s problems in ten minutes or less.

I would find out later that it was, in part, because I asked her what she’d do about things like that, that she decided I was the right man for her mother. The rest of it came from some very pointed questions she asked her mother about how I treated her on our dates.

Mandy and I were remarkably like teenagers in our early extracurricular relationship. There was a lot of lust going on and we both wanted to get to it as quickly as possible. We usually left her place, went to my place, and were in bed within ten minutes of entering my door. If she felt like she needed to be punished for something, which happened probably twice a month, then I had her naked and spread out in some humiliating pose while I put marks on her bottom. Then, after our first orgasm (or orgasms, on her part) we’d get up and get something to eat. We both reveled in the long, sweaty union of our bodies, pressing naked flesh together as I plumbed her scorching depths.

At first we went out once a week. That lasted for three weeks. Then it was twice a week. When both of us wanted to spend more time than that, together, that’s when we took Cynthia bowling with us.

As a side note, after that bowling alley conversation, Cynthia was never interested in going out with us. That would change, later, which would be very important to our future, but I’ll wait to document that.

Cynthia was a teenager, albeit a freshly minted one, so Mandy hesitantly allowed her daughter to stay home alone once when no other arrangements could be made. That went well, and Cynthia was visibly happy about it. Questions about “What did you do while Mommy was away?” were met with vague answers about TV and video games. Mandy had parental controls in place on both her TV and computer, so she didn’t worry too much about her daughter being exposed to objectionable material.

As to Mandy’s predilection to having me put marks on her bottom, her only worries were that her daughter might see the evidence of her punishment when Mandy was naked at home, such as when she was going to or from the shower. Their apartment had two bedrooms, but only one bathroom, so such a situation was possible. We both agreed there was no way Cynthia could be made to understand why her mother had handprints or belt stripes on her backside. I still didn’t understand it, and I was involved in it.

My lack of understanding didn’t mean I tried to wean her off of this personal choice in her sexual life. It was odd (or would have been had I stood back and tried to analyze it) but my own feelings and stance, when she needed pain, was to inflict it as genuinely but gently as I could. That didn’t mean I just gave her butt a negligent slap as she lay, naked, across my lap, or with her ass jutting in the air on the bed, or if she was bent over some piece of furniture. If I didn’t make it hurt, she gave me a glare that I learned very quickly meant I was falling down on the job.

So, over the next few months, I learned to take great pride in disciplining her with just the right amount of pain. With my hand it was relatively easy. If it hurt my hand, then I knew it hurt her ass. If I was using a belt, I paid careful attention to how each welt appeared, and how red it got. I took my time, making her punishment last long enough that her body gave me the feedback I needed. I realized there was an art to this and tried hard to become an artist. Mandy was always eager to mate with me, but on those occasions when I made her cry, and then cuddled with her, she was especially ardent in her emotional response.

I know this sounds like all we did was have sex and eat, but that wasn’t true. Yes, we usually had sex first, on a date, but then we spent time doing other things. At first all those things were done at my house, but as we slowly realized this relationship was probably going to last a long time, and that we had plenty of time to be lustful, we found that we could have a lot of fun doing other things, too.

Initially, we did things neither of us had thought to do before this, as typical single people. One Saturday we went to the John Wayne Birthplace Museum in Winterset, which was more interesting than I thought it would be. We went to the Iowa Events Center to stroll through arts shows, and the Artesian Gallery 218, at Historic Valley Junction. When we started eating out, instead of grabbing a bite between episodes between the sheets, we found lots of good restaurants and cafes. There were street performers like we’d seen in New York, and we stopped, hand-in-hand, to enjoy very good performances and drop bills into containers. We both liked music and I had always liked the blues. I’d never been to one of the performances put on by the Central Iowa Blues Society, so I took her to one of those. We went back for more regularly, after that. There is a district called the Avenues of Ingersoll & Grand, which, besides comprising commercial and neighborhood sections, is rich with historic character, small shops, public art and a lot of those dining possibilities I mentioned.

I should note here that I never saw anybody from work while we were out together. Des Moines is a fair-sized city, but a lot of the venues we went to together are popular, so I guess we were just lucky. Had people we knew from work seen us together it would have started rumors and gossip at the office. There wasn’t anything unethical about what we were doing, but it would have caused problems had we been ‘found out’ because you can’t do good work and gossip at the same time.

That didn’t happen, though, and at work we were “Mister Franklin” and “Mandy”, and once in a while I called her “Miss Potemkin”, where others could hear. With her new raise, Mandy bought nicer work clothes and always looked both professional and delicious at the same time. She had a penchant for suit dresses, which teased me with her bare legs. Once in a while, if she was sure no one could see, she’d bend over and “accidentally” expose the fact that she was wearing thong underwear or, perhaps, nothing at all under her skirts.

She distracted me routinely, but I was still able to concentrate on work. She usually performed her duties at work flawlessly, and when she didn’t, it concerned something that wasn’t really all that important. An example is that she’d bring me a document I needed to read, but could then dispose of. Once in a while a document like that had a ring on it, where a coffee cup had been set on it. I didn’t catch on, the first couple of times this happened and she gave me a gentle reminder.

“Oh!” she said, in mock timidity. “I was careless when I put my cup down. I’m so sorry, Sir.”

I got it, then. She manufactured reasons for me to discipline her. One of my favorites was when she said, “Damn! I chipped a nail,” and then hung her head and said she knew cursing at work was unprofessional and that she was sorry for embarrassing me in front of others at the office. She was in my office at the time and the nearest other employee was twenty feet away on the other side of my glass walls.

All in all, my life, and I think hers, too, was as good as it could get.


Mandy had regular periods, which she always informed me of. Neither of us was pursuing artificial birth control. It was mentioned several times, but neither of us seemed to do anything about it. She’d tell me when she was fertile, and her past with the professor framed that kind of communication. She’d stand in front of me, eyes down, hands at her side, and softly say, “I’m fertile now.” That was it. We still made love, but whether I came in her or not was my decision. She never asked me not to pull out. I usually did, cumming either on her back, if I was fucking her doggy style, or on her flat tummy if I mounted her missionary style. I learned not to let her ride me when she was fertile, because she would never get off of me if I told her I was going to shoot. She’d moan, “You could get me pregnant,” and then milk the shit out of my erection. Then, when she said, “I’m safe, now,” I’d fill her pussy with my semen and get it as deep in her belly as I could. I think having the genuine choice of whether or not she let me hazard her womb her made her feel powerful in a way nothing else did.

What happened with Cynthia was a complete accident. Mandy invited me to dinner at her house and while we were eating the atmosphere was comfortable. Cynthia had been around me enough that she called me “Bob” now. Christmas was coming up and they had decorated the house. One of the decorations was this little nutcracker figure, about eight inches tall and it reminded me of something my boss had told me earlier that day. The local opera house was doing a production of The Nutcracker and tickets would be available through the company for anyone interested.

“The Metro Opera is doing The Nutcracker,” I said. “I was thinking about getting tickets.” I was talking to Mandy, but it was Cynthia who piped up.

“Can I go?” she asked. There was a wistful note in her voice.

“Sure,” I said, without checking with Mandy first.

“Really?” Now the girl was excited. I looked at Mandy.

“Cynthia has always wanted to take dance lessons, but I couldn’t afford them,” she said.

“How about I take the two most beautiful ladies in my life to the ballet?” I suggested.

“Yes, yes!” squealed Cynthia.

“You’ll have to dress up,” I warned. “I mean to the nines. You’ll have to wear a gown and do your hair up fancy.”

“I don’t have a gown,” said Cynthia, her shoulders slumping.

“Well, I was wondering what to get you both for Christmas. Would gowns make a good present?”

Cynthia was sold. Mandy looked at me a little reproachfully. Later, while we sat on the couch watching a movie on Netflix, and Cynthia was on her stomach in front of us, head cupped in her hands on her elbows, Mandy leaned against me and spoke softly in my ear.

“Are you trying to bribe my daughter to like you?”

“Doesn’t she already like me?” I replied.

“We’ve never had money for luxuries,” she said. “Now you want to buy us fancy things. I’m worried she’ll get spoiled.”

“It’s just an ballet,” I said.

“Yes, but there are the fancy clothes and going to the hairdresser and all that,” she said.

“She should get to do that once in a while,” I said. “So should you.”

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