“Excellent job, Amy!” I said, looking up from the bundle of test documents to see the pride on her face. “You’ve come a long way since the beginning of the year when you started this!”

“Thanks, Mark!” she replied, “It’s hard to imagine now how badly I did it back then!” I replied with only a knowing smile, not wanting to diminish the work she had just completed by harking back to her less successful attempts. “Remember?”

“Yes, I do, but let’s focus on where you are now rather than remembering how you tried my patience then,” I replied.

“I really did, didn’t I? Try your patience, I mean?” she asked, but when I didn’t respond, she went on. “I know I did. After all, you threatened to spank me! Several times!” she said with a coy smile.

Amy had started as an intern, initially to help with a data gathering project, for which I had developed some software. She was supposed to do the testing that involved generating reports, emailing them to various executives, and then importing the responses into the database I had designed. With executives involved, I was particularly fussy about the results. I didn’t want the program to fail due to their ineptitude, nor did I want them all complaining about a poor program and process.

Being an executive myself, programming wasn’t my usual occupation, but we didn’t have anyone free to do it, and the data being passed back and forth was somewhat sensitive, so I took the job on myself. Initially, the testing was relatively simple, involving a small number of records and simple processes, but as the programming continued, it got more complex, involving thousands of records and a time-consuming setup for the test itself. I would give Amy the instructions to conduct the test and have her report the results back to me, or in some cases, I could look at the results in the database.

The first time she messed up a test was one of the early ones, and the amount of work to redo the test wasn’t so bad. Even with the simple test, screwing up the test several times started wearing on me, and my lack of patience started to show. The first time she realized on her own that she’d blown it, she showed up at my door with this sorrowful face, hoping to ease the effect on me with abundant apologies.

The combination of Amy’s personality and looks made it difficult to be angry with her. Her cute face contained full, sexy lips and big doe eyes that could melt your heart. Long brown hair framed her pretty face and accentuated her tall frame. Standing only a couple of inches shorter than me, she was slender, not skinny, with a pleasantly proportioned body. She had small tits, large enough to have fun with, but the feature that caught my eye, of course, was her bottom. Disproportionately large for the rest of her body, it was enticing nonetheless, especially to someone like me, who always pictures that particular part of a woman’s body draped across my knee, ready for a good, hard spanking! I imagined undulating waves spreading across her big, round cheeks as my hand splatted against what I imagined to be squishy mounds.

Adding to her appeal, Amy had an upbeat, happy personality. She could be goofy at times, both in her demeanor as well as the way she moved, giving the impression of a big, clumsy, lovable dog. It seemed the only time her cheerful attitude gave way to something darker was when she’d made a mistake, and her genuine remorse showed in her sorrowful face. 

The first few times she’d messed up the test, I let it roll off my back, told her it was no big deal, and set about resetting the test parameters so she could do it again. She rarely made the same mistake twice, but it seemed she’d screw up every test once. She didn’t really, but I was being very fussy about the result since I wanted them squeaky clean.

When we got to the more extensive tests, my attitude changed slightly. I still couldn’t be angry with her, but I did scold her a bit more as there was a lot of work in setting up the test data. The first time, I probably would have said something like, ‘Amy, please be more careful next time,’ which solicited heartfelt promises to do so until the next test. The second time, my reaction was probably something like, ‘Amy, what are you doing to me? Do I need to punish you in some way?’ in an obviously joking manner. She replied with something like, ‘Please don’t do that!’ in a similar funny way, but there was a hint of something else in her face and body language. The third time, I couldn’t resist …

“Mark?” she said, standing in my doorway late in the day with a dejected look, “I did it again! I ran the test without setting that flag, and now … now it’s all wrong!” She came into my office and around my desk to stand behind me to look at the screen I was about to bring up. As it came up, confirming what she’d told me, she added, “I’m such an idiot! Maybe you do need to punish me?” She was joking, trying to defuse the issue, but I couldn’t let it go.

“Yeah, you need a good spanking!” I said, trying to emulate her lighthearted attitude but also testing the waters to see her reaction. “Listen, don’t worry about it. I’ll set it up again now, and you can re-run it in the morning when you’re fresh! Okay?”

“Okay. I’m sorry, Mark! I won’t do it again!”

Of course, she did do it again, and at least twice, the suggestions of ‘spanking her naughty bottom’ and ‘taking her over my knee’ were made, with similar reactions from her. I began to wonder what she would do if I suggested it more seriously or actually gave her a good smack on the seat of her pants.

My mind, back in the present time, her phrase, ‘You threatened to spank me! … several times,’ finally stopped echoing in my head.

“Well, thankfully, you got yourself together, and that wasn’t necessary,” I lied.

“No, I didn’t! You just stopped threatening me. I remember a couple of times I screwed it up again! One of them was the worst ever!”

“You were learning, so I cut you some slack,” I replied unconvincingly.

“C’mon, Mark. Why did you stop? Did I do something else to make you mad at me?” She wasn’t letting this go, and I wondered why, especially considering the real reason I had dropped the whole subject of spanking. She looked at me intently, not letting me off without an explanation. “Did I?  Please tell me?”

“I stopped, Amy, because … because you got engaged!” 

Some would consider my chivalry in direct conflict with my desire to spank delicious female bottoms, but I disagree, and so would every woman I’ve spanked or been spanked by. Spanking requires a level of trust and respect that goes beyond the norm, and regardless of who’s spanking who, without it, the relationship ends. As much as I wanted to, and I thought I was getting close to actually spanking her, I couldn’t test Amy’s faithfulness by taking advantage of my position or not respecting hers. And Amy’s good nature made it even more difficult.

Anyway, she had been getting better at the testing, so the time between screw-ups was longer. A few weeks after the last mistake and spanking threat, I went into her area to find everyone congratulating her. Seeing her showing off a ring made it clear what the fuss was all about. I offered my congrats and a few wisecracks about marriage and waited for the excitement to die down to handle my business with her. I didn’t have to think about it at all; the playful spanking threats would have to stop.

“But you were just fooling around …” she started, but with the look on my face, understanding seemed to wash over her. She cocked her head in her best imitation of that big, goofy dog and put the pieces together. “You actually thought about spanking me, didn’t you?” she finally said, without the anger or suspicion I expected. I didn’t reply, not able to read her reaction correctly. “You were, weren’t you? Oh my God!” She turned and started for the door.

“Amy, I’m sorry! I didn’t really plan to …” I started, feeling an apology was the best approach, but reaching the door, she closed it and came back behind my desk, leaning against my credenza. 

“No, Mark. Don’t apologize! You don’t need to. You really stopped because I got engaged?”

“Yes. It seemed the right thing to do. I wouldn’t want some guy fooling around like that with my fiancé, however serious it was or wasn’t,” I replied, in the strange position of defending why I’d stopped threatening to spank her.

“That’s so sweet!” After a pause, she added, “But I can’t believe you were actually thinking about giving me a spanking!”

“Amy, I wasn’t actually planning to do anything.”

“I know, but you thought about it! Did you picture me with my pants down? Or pulling my pants down and putting me over your knee? … and then spanking my naughty bottom?” she asked in breathless excitement.

“Amy!” I shouted, trying to ground her fantasies back into reality.

“Mark! You don’t get it, do you? I love that you thought about spanking me! I wish you had planned to do it! Hell, I wish you had done it!” The shock was evident on my face, so Amy continued. “Yes, I was thinking about you spanking me too! From the first time you mentioned spanking, I couldn’t stop thinking about it, and as time went on, I wished it would happen. But I didn’t think you were serious, and I worried about what you would think of me if I pushed it any further. I also worried that I might give in to that temptation. I didn’t have to worry too much since you stopped talking about it, but I never stopped thinking about it!”

“Well, it won’t be the first time I misread the signals from a naughty girl who wanted a good spanking!” I said, resigning the whole subject to a ‘what might have been’ discussion.

“Really?” she said, but another dawn of understanding came over her. “Wait … not the first time? That sounds like you’ve done this before. Had a few naughty girls over your knee, have you?” she asked, her excitement ratcheting back up.

“Yes, Amy, I’ve spanked quite a few girls in the last twenty years or so.” Realizing how that sounded, I added, “But I don’t have anyone right now and no girlfriend either.” My experience didn’t bother her at all; quite the contrary.

“Oh my God! You’d know how to do it then, wouldn’t you?  … spank me, I mean.” My slight smile gave her the answer. “And you really wanted to spank me? I mean, you don’t see me as a big, gawky girl? Or that my butt’s too fat?”

“Amy, you are not a ‘big, gawky girl,’ and you have a very spankable bottom. I would have loved to treat you like my naughty, little assistant,” I started, seeing that she needed reassurance about how attractive she was, “who can’t do anything right …” She smiled at this. “… and who needs to have her boss pull her pants down, put her across his knee, and spank her naughty, bare bottom!” Realizing I was getting a little too into it and recognizing nothing had changed in Amy’s situation, I decided to stop there; though I could have gone on and on, I would have given at least even odds that I could have had Amy over my knee before long.

“Oh my God!” she repeated as she stood up, went for the door, and exited, leaving me confused. Though one could infer that she was angry and needed to get away from me, I believed she was on sensory overload and needed some distance to calm down. As I said, I’ve been in this position before, and oddly, as it turned out, she was as well. She’d misread my intentions and was possibly kicking herself for not seizing the opportunity to fulfill a fantasy, and now it was too late. She was getting married, and likely, her fiancé was not into spanking.

By this time, it was nearly the end of the day, and knowing I could not get back into anything work-related, I started cleaning things up and getting ready to go home. My thoughts remained on Amy, wondering what she was doing, trying to figure out what I’d say to her tomorrow (that would be awkward), and hoping she was okay. It had been fifteen or twenty minutes since she’d left when she whirled back into my office, her excitement level still high.  She closed the door again and came around to sit on the edge of my desk right in front of me. There was an intimacy about it that went beyond any of our dealings so far.

“Mark, you said you really had wanted to spank me, right?” she asked intently.

“Yes, but I can’t …”

“So, would you do it if I asked you to?”

“I don’t know Amy. It still doesn’t seem right!” As much as I would have loved to, I didn’t want to be responsible for affecting her engagement. That may sound somewhat pompous, like she’d never get over being spanked by me, but it had nothing to do with me. I’d given quite a few girls their first spanking, and if it was something they wanted, however unsure of it they might have been, they always ended up liking it and wanting more!

“Okay, umm. I … I don’t want there to be sex involved, you know? Just … just spanking!”

“And what happens when you find you love it?” I countered.

“I hope I do!”

“And then what?” I asked, somewhat confused.

“And then I know I have to get Brian to spank me!”

“I still don’t, um, why wouldn’t you ask him now?”

“That’s going to be very difficult. It’ll probably take some time, and since I’m not sure I really want it, it might screw things up before they even start! Does that make sense?”

“Oddly, it’s starting to. So, you want to find out if you like spanking by having me spank you, after which you can try to convince Brian to do it, knowing you want it?”

“Yes! See! You understand!” she said, with a big dopey smile.

“Amy, that still doesn’t explain why Brian can’t give you your first spanking. Believe me when I say that I know you’ll like it. No doubt in my mind!”

“But … but I could end up not liking it because Brian didn’t do it right! You know what you’re doing! You’ll spank me good!”

Her logic made sense in a convoluted way, but I still wasn’t sure I wanted any part in it. Part of it was that I didn’t want to start with the knowledge that it wouldn’t go beyond this one event, even though I have spanked girls where the one spanking was the beginning and end, but it wasn’t planned that way. I’d do it for Amy if that were all there was to it, but I still didn’t like doing it behind her fiancé’s back.

“Please, Mark? I promise I’ll take a good, hard spanking! You can give it to me good, and I won’t chicken out!”

“Alright,” I said, giving in and not believing my tone of voice, sounding like I’d just agreed to spank this wonderful girl as though it would be a chore. “When shall w…”

“Thank you! Oh, I can’t wait! So, this is how we’ll do it. Tomorrow I’ll …”

“Tomorrow? I thought you’d want it now!”

“No, we can’t just do it now! I have to earn my spanking! … and I’m not dressed right!  … and … and” she said, sounding like she’d planned this all along, yet she could not have. “Okay?” she asked and continued when I nodded. “So tomorrow I’ll figure out something I can do to make you mad enough to spank me and … and then you’ll tell me I’m going to get spanked and to meet you here in your office at the end of the day! And then I’ll come here, and you’ll take me over your knee and spank me! Really hard, okay?”

It would have been impossible to disagree with her at this point; she was so caught up in her plan, and it wasn’t a bad plan, but I’d have to inject some reality into it somehow if it was going to meet her expectations.

“Okay,” I replied, “Friday is probably a better day anyway, but I should spank you just for driving me crazy!”

“That could be part of it!” she giggled. “Thank you, Mark!” she added, kissing me on the cheek. “It’ll be fun! You’ll see!” she said as she left.

I sat and thought about what I’d gotten myself into for a few minutes and resolved to sleep on it and see how I felt in the morning. I could still call it off if it didn't feel right. I finished wrapping up my day and headed home.