Spanking My Secretary - Cover

Spanking My Secretary

Copyright© 2022 by Lubrican

Chapter 9

Romantic Sex Story: Chapter 9 - 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  

For the rest of the week our professional lives went smoothly, meaning she didn’t “ask” me to discipline her. She called me “Boss” in my office, but that was the extent of any demonstration on her part that we were closer than any other secretary with her boss. For that matter, maybe lots of secretaries called their boss “Boss”.

On Thursday, she came into my office and stood in front of my desk, like she was waiting for me to tell her to do something.

“Cynthia informed me this morning that we are invited to your house this weekend,” she said.

“All weekend?”

“She said ‘weekend’,” said my executive assistant.

“Interesting,” I said.

“I’m curious about when this invitation was extended,” said Mandy. “Have you been talking to my daughter behind my back?”

“In a manner of speaking,” I said. “When I talked to her that night in her bedroom I suggested you two could sleep over at my house some time. She didn’t seem excited about that possibility.”

“What should I tell her ... Sir?”

I was used to the “Sir” thing by now. I had also learned to tell, from her inflection when she used that honorific, if it was simply that - an honorific she’d been taught to use and used it unconsciously - or if she intended it in a deeper meaning: “I’m letting you determine my future in the near term.”

“I think we should all do something together and then see how she feels about ... things,” I said.

“Do you have something specific in mind?” She blushed. “I mean about doing something together.”

“I did,” I said. “When I talked to her I was thinking about a picnic, maybe at Jester Park or one of the lakes in the area. It’s still too cold for that, though.”

“We’ve already been bowling,” she said. “What about going to a museum?”

“I’m not really up on the museum culture in Des Moines,” I said.

“We went to the Science Center one time,” she said. “She had a good time, there.”

“So go back there?”

“Maybe. I know there are several art galleries in town and Cynthia loves to draw.”

“Let me do some research and we’ll give her some options to choose from,” I said.

“You make me so horny,” she said, softly.

“Now?”

“You care what Cynthia thinks,” she said. “That makes me horny.”

“Well, I’m going to have to keep caring about what Cynthia thinks,” I joked.

“Please do,” she said.


That night I went online and was astonished at the cultural offerings in Des Moines that I knew nothing about. The variety was impressive. There’s even a stage coach museum and another one dedicated to trains. One I was familiar with, in Winterset, Iowa; the John Wayne museum. It was really fascinating. Of course I didn’t think a thirteen year old girl would go for stagecoaches, trains, or an actor whose movies she’d probably never seen, but there were other options.

Mandy had said Cynthia liked art, so I wrote down the Des Moines Art Center, the Kavanaugh Gallery, and one called From Our Hands, which looked like it had locally made stuff. The next morning I handed Mandy the list.

“This is what I came up with.”

She read it and said she’d ask Cynthia which one she wanted to go to.

“We can do more than one,” I said.

“What if she doesn’t want to sleep over?” asked Mandy.

“Then you don’t.”

“But I’m going to want to,” she said, pouting just a little.

“Do not worry,” I said. “I intend to bed you well and often.”

“I love it when you talk like that,” she said. “I’m horny.”

“Go to the ladies room, find a nice comfy stall, and spank your clit,” I teased.

“Bastard,” she muttered.

“Ohhh, you’re gonna pay for that, little girl,” I said.

“Now?” she asked, hopefully.

“You want everybody out there to look at my office, with the blinds closed, and hear your pretty ass being slapped and you moaning?”

“Bastard,” she muttered again.

“Let me know what Cynthia says,” I said, ignoring her attempt to get me going. I was afraid she’d ask me to discipline her over lunch. If I did that I’d have to either get a hotel room, downtown, near the office, or take a two hour lunch if I took her to my house. It was a 30 minute drive each way, if there was any traffic and I didn’t catch the lights all green. I didn’t like either option.

“Yes, Sir,” she answered. “If you’ll excuse me, Sir, I need to use the ladies room.”

“Try not to make enough noise that somebody will investigate,” I said.


Cynthia opted for the Des Moines Art Center. She looked it up online and said it looked interesting.

Mandy called a cab and put things in the back for both of them, should it develop that Cynthia wanted to sleep over. They got to my house around nine in the morning and by ten we were at the art center. It was pretty cool and it took two hours for Cynthia to say she was ready to go.

“I’m hungry,” she said. “We can come back here later, right?”

“Either today or another time,” I said. “What are you hungry for?”

“Food,” she said. She smiled. She was actually teasing me!

“I will immediately go to the tourist information people and ask them if there’s a restaurant called ‘Just Food’,” I said.

“There’s a restaurant here, in the art center,” Mandy pointed out.

There was. It’s called Tangerine at the Art Center and we had burgers and cheese cake that I want again as I write this. Had it been warmer, we might have strolled through the Greenwood-Ashworth Park, which is next door to the art center. Instead, Cynthia said she’d like me to teach her how to shoot pool.


I was lucky. Cynthia had an eye for angles and an innate understanding of how power affects the cue ball. I went through the concept of putting English on the ball and how to chalk the cue tip and she said, “I want to try it.”

Mandy sat on a bar stool and watched. Thirty minutes later I went over to her and touched her thigh.

“Bob and I are going to go spend some time together,” she called out to her daughter.

“I’m good,” said the girl, eyeing the one ball, which was ten inches from a corner pocket. “Don’t make too much noise, okay?”

Mandy took my hand in loose fingers and led me to my bedroom.

“Now? With Cynthia right out there?” I asked.

“You’ve been a very good boy all day,” she said. “You deserve a reward.”

“And you’re my reward?” I teased.

“I hope so,” she said, reaching to unbutton my shirt.

She seemed like a different woman. The initiation of our sexual relationship had been based on pain and guilt. I had shown her there could be a whole different kind of sex and that’s what she wanted in this moment.

She got me naked and ran her hands all over my body.

Then she disrobed and pressed her body to mine. Her breasts felt hot against my chest.

“I’m so lucky I met you,” she murmured into my chest.

I traced my fingers down her spine. She shivered, and then pulled away.

Now her fingers were insistent and strong as she pulled me to the bed. As she crawled onto the bed she showed me her glistening pussy lips. I didn’t want to take her from behind, though. I wanted to be on top of her, pressing her into the bed, covering her body with mine. I wanted her to be helpless as I plundered her sex. I felt powerful as I got over her and she opened to me. In that moment I was the lord and master of the castle and I was going to take what was mine.

I entered her too hard and she moaned. It was that little, tiny moan of pain that woke me up and made me realize Mandy Potemkin had taught me more than she knew. I had never wanted to dominate a woman before this. But I wanted to claim her in every possible way, and leave her no escape.

“I love your penis so much,” she whispered. “I’m so lucky you let me have it.”

I soaked in her, calming my emotions, until her own hip thrusts reminded me that there were two of us here, and that I needed to pay attention to the satisfaction of my queen. The princess was otherwise occupied and we had time. I just needed to be “Bob” again, rather than a conquering monarch.

She wasn’t my executive assistant. She was my lover. Cynthia wasn’t a princess. She was just the impressionable daughter of my lover, who trusted me to treat her mother like all women deserved to be treated.

“I’m the lucky one,” I panted, as I started to move.

All she did was moan, and whine, and yip. I worked her over until I’d felt her pussy clamp down on me three times.

“I want to cum in you,” I whispered.

“Yes!” she blurted.

“I want to make a baby in you, Mandy,” I groaned.

“Okay,” she gasped.

“This isn’t punishment,” I grunted.

“I know,” she whined.


The details of the aftermath of that particular session remain vivid in my memory to this day. I sagged on her and started to roll, but her fingers and arms stopped me.

“Don’t get off,” she said, in that peculiar voice that (mostly) women use when a man they’ve had sex with is still crushing them. She sounded out of breath, but she was willing to endure that so that she could wring the last little bit of pleasure out of the intimacy she had just shared with me.

“I’m crushing you,” I said, pushing up on my arms, but leaving my lower body on hers.

“I love that feeling,” she panted. “I love it when you protect me from the world.”

To her, what I was doing was a very little bit like a soldier who throws his body on top of one of his friends, to protect him from the ravages of war.

“I love you too much,” I sighed.

“How can you love me too much?” she asked.

“I want you in my life every day,” I said.

“I am in your life every day,” she breathed.

“I don’t mean like that,” I said. “I love working with you. You’re efficient, intuitive, and a hell of a secretary. But I’m also distracted by you, at work. I want to bend you over my desk five times a day.”

“Okay,” she said, smiling at me.

“You know we can’t do that,” I said.

“So what should we do?”

“Well, I can’t fire you. That wouldn’t do at all. What I think is that you and Cynthia should come live with me.”

Her attitude shifted so rapidly it too me by surprise. Her hands came to my chest and, with strength that astonished me, she pushed me off of her. In a flash she rolled, straddled me and sat on my six pack. Well, she sat on where my six pack would be if I had one. I felt her pussy drool on me, making a little, warm puddle.

She was breathing hard and her voice was soft, but harsh.

“Bob, you can’t go from, ‘Hey, kids, how about a sleepover at my house?’ to ‘Hey, you two, how about moving in with Bob and just living together every day?’ Those two dots don’t connect. I love you but that wouldn’t work on a whole bunch of levels. What happens if your boss finds out your executive assistant moved in with you? You wouldn’t have to fire me. He’d do that in a heartbeat. You might even get fired yourself! And yes, Cynthia is warming up to you, but that’s like taking her from a cold storage locker to the surface of the sun. It’s too much, too soon.”

I heard her words, and they sank in, to a degree. But all I was really doing was drinking in her naked beauty as she sat on me, like I was a mechanical bull that hadn’t started moving, yet. She was so beautiful, so desirable. She wasn’t my queen, but I wanted her to become that.

“Bob? Are you listening to me?” Her voice intruded on my pleasant thoughts.

“Yes.”

“No you’re not. All you’re doing is staring at my breasts. Is that all I am to you? A pair of breasts? A vagina you can spew in whenever you like? Am I just your sexual toy?”

“Of course not,” I scoffed. “I love you!”

“Well, then, start acting like it! You can’t just toss something raw and unprepared like that out there on the table and say, ‘Gee, look what’s for dinner, folks!’ That’s just ridiculous. It’s reckless! In fact, I think you should be punished!”

I wanted to laugh in delight. She was so perfect. How did I deserve this woman? I didn’t laugh, though. I could hear she was seriously concerned about what she thought of as my flippant remark.

“Okay,” I said. “But you have to just use your hand. I’m not ready for either the belt or paddle.”

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