Spanking My Secretary - Cover

Spanking My Secretary

Copyright© 2022 by Lubrican

Chapter 11

Romantic Sex Story: Chapter 11 - 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  

We adults make some assumptions about the children among us, specifically those in the roughly twelve to sixteen age range. Sometimes those assumptions are both wrong and dangerous. Among the most dangerous is the assumption that kids that age can’t understand adult relationships. It makes sense (to us adults) because someone with less than sixteen years of life experience hasn’t had time to grasp the intricacies of complicated and convoluted relationships.

There’s just one thing wrong with that particular assumption, though, and that is that kids have plenty of their own complicated and convoluted relationships. They can have “best friends” who they are closer to than adults are, and who they love intensely. I put that title in quotes because it’s a loose concept that can mean many different things. But kids can bond and love just as intensely as adults do. Some would argue that the lack of social politics in childish relationships means they are fleeting and insubstantial. Others would argue that childish politics are the most cutthroat of all.

Granted, young people often see things on a more basic and simple level than older people do. It sometimes seems like adults are almost eager to make things as complicated as possible. Children are well known to cut to the most basic approach. An example is: I want that and you should get it for me. That scenario plays out in grocery and toy stores every day. Kids are reduced to screaming fits because they want something and they believe it’s mom and dad’s job to get it. It’s just that simple. They don’t understand home economics and budgets and they don’t want to.

On the other hand, concepts that are much more complicated and mysterious than home economics and particle physics come so easily to children that it’s almost scary. I’m talking about things like love, and compassion, and empathy, things adults have a very rough time with. For kids, it’s obvious. We should love each other a lot. We should try to understand how the other person feels and arrange the world to contain as little pain as possible.

Cynthia had no clue why her mother wanted to be spanked – ever – and she might never understand that. The image of her naked, screaming mother, face flushed, as she whaled away at my naked, hairy backside that night would probably stay with her in uncomfortable dreams her entire life. But those dreams wouldn’t be nightmares because she had the basic understanding that what she had seen was between consenting adults. It was weird, yes. It was crazy, yes. It was even maybe perverted, yes. But it had been consensual and it had been productive.

Basically, as odd as it seemed, it had produced happiness.

So it was okay with Cynthia.

She knew her mother loved me. Kids can detect love like a K-9 officer’s dog detects drugs or explosives. They may not understand how love works, but they know it when they see or feel it. She knew her mother was happy. Mandy hadn’t moaned and groaned or complained about her lot in life before she became my executive assistant. She had a decent job and she was glad she had it. It fed and sheltered her daughter and that was important. Yes, she couldn’t afford a car, but the upside of that was that all that walking kept her in tip top shape.

When she got her promotion, though, the uptick in her “happiness index” was noticeable to her daughter. And that needle kept going up, even before the first time I reddened Mandy’s ass. She liked her boss and she liked working for him. That can make a huge difference in any job. And then I did redden her ass and fuck her tight, juicy pussy, and she was happier yet.

Cynthia didn’t know why the needle was climbing. She just knew it was. Cynthia did fulfill adult assumptions in one sense. She accepted a very complicated situation on a very basic basis.

She believed her mother when Mandy said I wasn’t hurting her. She didn’t understand this “spanking stuff” but she believed it wasn’t hurting anything. And she knew her mom was happy because I was in her life.

And that was good enough for this particular thirteen-year-old girl.

Rather than concentrate on the imponderables associated with her mother’s ‘weird beliefs’, Cynthia gave her attention to something she did want to participate in and understand. She watched her mother’s body change as life grew inside it. Mandy missed her second period roughly a week after my ‘proposal’ was accepted. Babies are not aware that their mother might be diminutive in stature. Assuming there is good nutrition and a lack of other complicating factors, babies just happily get bigger. If the mother is an Amazon it might not be so noticeable for a while, but with Mandy, she began to show a little sooner than the typical sixteen to twenty weeks most women can go before it becomes obvious she’s with child. Part of that might have been because all that walking had kept Mandy’s abdomen board-flat, and even a small pooch was discernable to someone who could see her naked.

That first detectable bump didn’t show up for another month, though, which was an endless source of angst and frustration for Cynthia. Every time Mandy took a shower her daughter arranged it so she could see her mother’s naked belly. Things had always been “relaxed” in the house, in terms of modesty, but neither woman in the house had run around bare ass naked. Cynthia went online and researched what changes a woman’s body went through in pregnancy, however, and she wanted to see each of those changes in her mother. So, suddenly, Mandy was confronted with a daughter who said things like, “Take your robe off, Mom. I want to look at the baby,” and “Give me that towel, Mom. I want to see if anything has changed, yet.”

By the time things did change enough for Cynthia’s eyes to detect, Mandy had become accustomed to the somewhat odd feeling of displaying her naked body to her teenage daughter. There was really only one complicating factor. That was when Mandy knew her ass might display as mottled, or striped. The elephant in the room had been acknowledged, but that didn’t mean Mandy wanted that elephant to keep lumbering around in front of her little girl’s eyes.

This was why Cynthia got used to the basic level of modesty her mother insisted on: “Cool your jets and let me put on a pair of panties, first!”

I haven’t done any polling, and there doesn’t seem to be much out there in terms of anecdotal research, but while I’m fairly sure many expectant mothers share the daily progress of their pregnancies with the man who got them that way, it’s pretty rare for her daughter to have a front row seat to every little change that takes place as new life stretches things out and demands more resources from its mother.

What I do know is that the connection between mother and daughter grew stronger and stronger as the months passed, until it was stronger than an ionic bond. I didn’t see most of this, of course, at least not in the first two trimesters. Mandy and I were trying to plan, rather than just jump out of the frying pan. We already knew that even if we planned the most basic, quick wedding she would be obviously pregnant as she walked down the aisle. There was some talk about waiting until after the baby was born, but Cynthia would have none of that. She was too eager to stand up with her mother. And a simple, basic wedding wasn’t in the cards, either. Cynthia wanted pomp and ceremony.

Oddly, or perhaps because most of Cynthia’s life had been lived with a single mom, the idea of Mandy going through the ceremony with a big belly didn’t bother the girl. That wasn’t important. What was important was that this rich, important guy was claiming her mother and she wanted the whole world to acknowledge that. Neither Cynthia nor her mother had ever been “important”, in her mind, and now she was going to move into a house that had a pool table and a swimming pool and a BMW in the garage.

Cynthia wanted to show off for her friends.

Who, ironically enough, were not invited to the wedding, once things got to that stage of the process.

Mandy described it to me in our moments of privacy, which now had to be ensured by locking the door to whichever bedroom we were in. Cynthia seemed to “forget” a lot that she was required to knock before entering. The picture Mandy painted for me as we lay, catching our breath after making love, was of an eager, inquisitive girl who put her face right next to Mandy’s bump and talked to her little sister. She was sure it would be a sister.

One of the earliest “conversations” Cynthia had with her sister was about a month after the pregnancy was acknowledged, which made the baby roughly thirteen weeks old. Cynthia’s nose was a couple of inches from Mandy’s belly button when Mandy said, “Oh! I just felt her move!” That movement wasn’t visible, externally, of course. The fetus was only the size of a peach, and the average woman can ingest several peaches without it showing.

Really?” gasped the girl. “She moved? I didn’t see anything! Why didn’t you show me you were moving? (addressed to the baby) How do you know she moved?” (addresssed back to her mother)

It would have been confusing to an onlooker, because Cynthia would talk to the baby one second and talk to her mother the next. “How does it feel?” was a common question. Another common occurrence was for Cynthia to “educate” her mother on what the fetus looked like at any given moment. “She has fingers now, but they just look like little buds or bumps.” Or it might be, “She’s two and a half to three inches long, now.”

Ironically, I seemed somewhat incidental to all this fascination.

“Hi, Bob,” Cynthia might say, as if I was the mailman, or something, as I entered the house. “Come on in. Mom’s in the kitchen.” I seemed to be a fixture who came and went, unless they were ‘sleeping over’ at my house. We did that a lot if we were going somewhere together as a ‘family’, such as the zoo or on a picnic or hike. Her seeming indifference to me was an act, though. We had done many of those things prior to our engagement, but Cynthia wanted to do them all again after plans were made for me to become her step-father. Cynthia was avid about how her mother’s body was changing, thanks to my involvement in their lives, but she did not display any interest in the romance between her mother and me. It was just accepted as being there.

I was just accepted as being there.

And I felt incredibly lucky at being accepted – by both of them.


Eventually, of course, it became obvious that Mandy’s condition would become noticeable by people outside the family. That meant actions that had been delayed needed to happen. It started on a Friday morning when I approached Marge Addenhall in her surprisingly small office and said, “Marge, I’m going to need a new administrative assistant.”

Marge looked up at me over the top of her glasses. I felt like I was being inspected by an auditor from the IRS.

“Oh? Trouble in paradise?”

“Not at all. She’s thinking of resigning. She wants to spend more time with her daughter.”

“And she can’t do that while she works for you?”

I knew it would come out sooner than later, so I just bit the bullet.

“She’s pregnant, Marge. We both know the guys upstairs won’t want her representing the company when she starts to show.”

“I see,” said Marge.

“I’d like her replacement to be ugly, or at least plain,” I said, somewhat artlessly. I had more than enough experience to know that having an attractive administrative assistant could be ... distracting.

“We don’t assign ugly women at that level,” said Marge.

“Well, at least make her plain. And married. Happily married.”

“Aside from her daughter, are you why Mandy wants to resign?”

“Yes.”

“Care to talk about it? I thought you two got along well.”

“We do. We’re going to get married. So don’t reassign her. She’s going to be a stay-at-home mom.”

“My, my, my. A woman actually tamed the great Robert Franklin?”

“Don’t bust my chops, Marge. Just get me a good assistant.”

“Why didn’t Mandy come tell me this, herself? Please don’t tell my you’re one of those guys who makes all the decisions for his wife.”

I got on my phone and called Mandy. I put her on speaker.

“Could you please come to HR? Your input is needed.”

We had discussed all this and she had felt that it was more important for me to tell HR what I wanted than that she be there to warn them of her anticipated resignation.

“Okay,” she said. “Be there in a jiffy.”

Marge stared at me and then moved some papers around on her desk while we waited.I thought about the ‘awkward pauses’ I used to see on the Craig Ferguson show, except this really was awkward.

“Congratulations,” she said, when Mandy breezed through the door. “I think.”

“Thank you,” said Mandy, beaming.

“You really want to quit?”

“I do,” said Mandy. “I need to plan the wedding and I really don’t feel like having to get to know another boss.”

“You got to know this one pretty well,” Marge commented.

“I like him!” said Mandy, brightly, showing a wide grin.

“This could cause some waves,” said Marge. “Relationships like this are frowned on in the company.”

“Which is why I’m resigning,” said Mandy. “Out of sight, out of mind.”

“So none of us will be invited to the wedding?” Marge was clearly unhappy.

“I didn’t say that at all,” said Mandy. “None of that has been planned, yet, though. We’re not sure when we’re going to have the ceremony.”

“May I recommend it be before the baby is born?” said Marge, boldly. “I like you and I’d hate to see this miscreant leave you high and dry.”

“Marge! That was unkind!” yipped Mandy.

“I’ve known him longer than you have,” said Marge.

“Yes,” I said, not worried at Marge’s theatrics. She had known me longer than Mandy had and I knew her better than Mandy did. She was joking.

At least I hoped she was joking.

“The difference is you kept turning me down and wouldn’t make a baby with me.” I grinned.

I really hoped she was joking.

Marge blushed, which made me heave a silent sigh of relief.

“I’m smarter than this one,” she said, gruffly. “And my husband might have objected.”


Later that day Mandy came into my office and stood, head down, hands clasped in front of her. It was a posture I recognized.

“Yes?” I asked.

“Cynthia is spending the night with her friend,” she said, softly.

“And?”

“When Marge processes the paperwork, people will know about ... us. I have shamed you.”

“That’s not acceptable at all,” I said, playing along.

“I know, Sir,” she moaned, softly. “I should be punished.”

“I don’t have time right now. I will discipline you tonight.”

“Yes, Sir,” she said.

Her posture upon leaving was perky and there was bounce in her step.


Half an hour before quitting time she came in again. There was no hint of submissiveness, this time.

“Can I leave early? I have some things to do. I can be at your house at seven.”

“So late? I have to eat supper alone?”

“You can add that to my punishment,” she said.

“Okay,” I said. “I’ll see you then.”


She parked her car in my driveway at seven sharp. She had a small bag with her when she came through my front door without ringing the bell. She was still dressed in her work clothes. I had taken a shower and had on a pair of running shorts and a tank top.

“You’re late,” I growled, menacingly.

“No, I’m not,” she said, impudently. “Let me take a shower, first.”

“I’ll supervise,” I said.

“No, you will not,” she said, firmly. “I haven’t eaten and I’m starving. Is there anything to snack on in the fridge?”

I repaired to the kitchen where I pulled out the half of bucket left from a stop-off at KFC, the night before. It was original recipe, so the skin was in pretty good shape. I decided she’d heat it up if she wanted it that way and got out a half-empty tub of Amish style potato salad. I opened a can of black olives and dumped it into a bowl. I’d eaten about half of the olives when she made her appearance. I didn’t quite choke on the olives in my mouth, but it was a good thing they were already mostly chewed, because I forgot all about eating.

She was wearing what is called a halter teddy, which means the top was in halter style, but flimsy in the extreme. The black lace cradled her breasts and let me barely see her nipples. The matching bottoms were clearly crotchless, since they did nothing whatsoever to cover her bare pudendum. Her bare feet showed she’d decided on bright pink nail polish. It didn’t match her fingernails, which were covered in clear lacquer, as befitted her station at work. Her hair was still damp, and hung not quite plastered to her shoulders.

“Yum,” she said, eyeing the food as if she were dressed in a nun’s habit. “That’s going to make a mess, though.”

I stared as she sat, knees akimbo, in a completely un-ladylike position on the chair. Within half a minute her fingers and lips were covered with the eleven herbs and spices, KFC mixed into the breading of their chicken, which she devoured hungrily. She ate a few spoonfuls of potato salad and then daintily picked up five olives and popped them into her mouth. She rose, came to my side of the table and stood, waiting.

“Scoot back,” she finally said, a hint of impatience in her voice.

I moved and she straddled me, obscenely exposing her pussy lips in the process.

“Open!” she ordered, pushing a greasy finger against my lips. “I’m all messy. Clean me up!”

I never had as much fun sucking on someone’s fingers as I did that day. She was, indeed, finger-licking good.

She let me have my fun and then hopped off to go wash her hands at the sink. The back of the panties covered almost nothing, either. I actually pictured my handprints on the pale skin to either side of the black lace.

“I’m ready,” she said, turning. “Are you ready?”

“Yes,” I croaked.

I followed her, watching her bottom jiggle and sway. When we got to the bedroom I realized this was going to be a special session.

Her riding crop was perched on top of the pillow I knew would support her hips, making her loins push up into the air. She picked up the crop and handed it to me before shimmying out of the panties and prostrating herself, legs spread, with another pillow under her head.

“There will be gossip all over the office. People might think badly of you.”

“I can take it,” I husked.

“It’s all my fault,” she said.

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