What am I going to do with her?

“I’m sorry, sir, for doubting your knowledge” the Office Communicator Instant Message from Allison said. She had earlier chosen not to take my advice on how to do something, and after wasting several hours and having to work late, had just now taken my advice.

“That’s I’m sorry, MISTER Sir.” I typed back, with a smiley.

“I’m sorry, MISTER Sir. So very sorry, MISTER Sir.” She typed back.

“Ok, that’s better.” I replied. “I’m glad we’ve had this little chat!”

“I’m sorry, Mister Sir, it won’t happen again”. Now, I was starting to get a little hard. Allison had jokingly called me sir on two previous occasions, always in a light hearted manner, but still, she said sir. Then another time, she had jokingly called me Daddy, because there had been another occasion where I had given her some advice. I’m 45, she’s 25, technically old enough to be her parent, but like so many things with Allison, she was a jokester, so you never took anything too seriously.

“I’ve been bad”.

“Just don’t let it happen again, and we’ll be fine”

“Well, OK, thank you for saying that. But I’ve been bad. I’m just a bad, bad girl, and I am truly and deeply sorry, sir MISTER.” she typed. I thought of her being bad. Being naked and bad. Was her pussy shaved? If so, how? Laser? Razor? Electric Shaver? Wax? What about her ass? Does she groom back there too? I knew she had nice toes, because now and then she wears open shoes. Then dammit, the next message from her is a smiley. I guess I’m not the only person on earth who tries to relieve tension or soften statements with a smiley. Who’d a thunk?

“That’s MISTER Sir. And the ‘S’ should be capitalized too!! Not ‘sir MISTER’. It’s ‘Sir, MISTER Sir’ with a capital ‘S’! You got it totally wrong. Oh my gosh, what am I going to do with you?” I typed. Then again, I followed almost immediately with a smiley, but she did too, almost at exactly the same moment. Clearly, we’re both playing the same game, and it’s made me rock hard.

“I’m sorry, Sir, MISTER Sir. You are right. I am so sorry. I am so bad. I say bad things. I do bad things. I think bad things. I think about doing bad things. I am bad, Sir, MISTER Sir, so very, very bad.”

That last comment was also enough to make me feel that this round of innuendo had officially turned into something new. I also knew that the online Office Communicator was not private, and we really needed to stop using it any further. I got up, and walked down the hall and into her cubicle. “Come with me.” I said flatly, and stood by the door until she got up and walked toward me. I knew I was visibly hard, but in a Freudian way hoped she’d notice. I pointed down the hall, and she started walking. Nobody worked late here, and there was a small conference at the end of a hall, very much off the beaten path. “In there.” I pointed to the door, then once in, pointed at the conference table and said “And bend over.”

In spite of appearing confident and in charge, I had no idea how this was going to go. On the inside, I view spanking as a playful thing, mainly an excuse to get my hands on a girl’s naked bottom. But with the long history of so much joking around, I still wasn’t completely sure if she would play along. I had strong suspicions, but for these very tense microseconds, I did not know what would happen next.

Thankfully, she promptly bent over the table, and said, “Yes Sir, MISTER Sir, Sir. I am so very sorry for saying and thinking such bad things.”

By now, I had hiked her knee length skirt up and onto her back, and with one hand, was holding the skirt up on her back. Powder blue boy-shorts style panties on a delightful ass. With a thong tan line too, very nice. “From now on, you don’t wear underwear to work. Do you understand?” I said, and smacked her slender bottom through the fabric of her boy-shorts style panties. Playfully hard, enough to perhaps sting just a bit, but not that hard.

“Yes, Sir, MISTER Sir.”

“Hold this in place.”, and I put the fabric of her skirt into each of her hands, so she could hold the skirt up for me. I yanked her panties down to her shoes, and guided one foot then the other out of them. Stood back up behind her, and with my left hand pulled her left ass cheek open, exposing her little ass hole. I smacked her right cheek briskly with my four fingertips, not extremely hard, but hard enough to leave a little red mark. “I do feel that you are sincerely sorry, but I do have to keep you in line. What are these bad things you say you are thinking?” Smack, Smack, Smack, Smack, Smack. Five more firm swats on her right cheek.

“Sir, MISTER Sir, I confess. When I disagree with you Sir, I do it on purpose, because my pussy twitches whenever you make that ‘what are you going to do with me’ comment you always make, Sir. I do it because I dream about you spanking my bottom, Sir, Mister Sir. And then at night when I suck my husband’s cock Sir, I imagine that it’s your cock, Sir. And I think about your cum, sir. I think about your cum a lot, in me, in my mouth, everywhere, Sir.”

Ten more smacks, still mostly playful, but enough to cause redness and make my own fingers tingle. “Those types of thoughts make me happy and are acceptable to me. You can think things like that about me. I will allow it.”

“Thank you Sir, Mister Sir. Please sir, may I have ten more?” I smack her bottom ten more times. “Thank you Sir, Mister Sir. I will be good for you, Sir, Mister Sir. Please sir, ten more? Harder please Sir, Mister Sir, to make sure I remember this lesson?” This time, I spanked quite hard. I know I’m an amateur at this whole spanking thing, but I’m fine with my amateur status. I have the naked bottom of a hot girl to spank, so I must be doing something right.

“Very Well. I can tell you are remorseful.” I zip my pants down, and in one motion, push my pants and underwear down to the floor. I hook each thumb under each of her ass cheeks, the left one intact, the right one bright red, and from behind, I glide my cock into her pussy. “You have been good now, I am pleased.” I am now thrusting my cock into her, and it is tight and very wet. Her ass also looks delectable. I guide her by her hips so that she is a bit lower, and she gets on her tiptoes. My legs are on the outside of her ankles, and I thrust deeply into her from behind. I also know that the cleaning lady shows up at seven, and it’s 6:50. “Cleaning lady will be here in 5 minutes. Gonna have to make this time a little speedy.” I say. She mumbles something about the cleaning lady being sort of cute, and we both laugh. I am of course aroused even more thinking about Allison liking girls too.

I decide to expedite things, and I fuck her faster and deeper. And just as I am about ready to explode, I pull out, take her by the hand, turn her around, guide her to her knees, and put my cock into her mouth. I barely make it in time, as my cock starts firing molten bursts of cum into her mouth. She struggles for a moment to collect and swallow it all, but gets the job done, the entire time, her sexy fingers holding my cock, caressing my balls, and sexily playing with the shared wetness from our actions..

“Now sit up here, and cum for me. Do whatever you normally do to cum, it doesn’t have to be a show for my pleasure.” and I sit her on the edge of the desk.

“Sir, will you pump your cock for me, Sir, Mister Sir? That is what I usually think about when I think about you, Sir. ”

I stand in front of her, watching her, as she starts lightly patting her clit. I pump my cock, slow full length pumps, enjoying the show. She is an adorable thing, and seeing her naked pussy is wonderful. I make a mental note, that next time, I’m going to need to taste that. But she is on task to make this orgasm happen, and she quietly throws her head back, and tenses up, as her pussy starts to quiver and pulsate. She is in a daze for a while, basking in her orgasm then recovering, and finally opens her eyes and says “Thank you, Sir, Mister Sir.”

6:59. I know we are out of time. “You have done well. I am pleased. Now remember, no more underwear. And wear your black pumps and the yellow and black skirt tomorrow.

“Yes, Sir, Mister Sir.” The sound of a vacuum cleaner down the hall is our cue to get back to work. As we get to her office, she says to me in a sexy voice “Sir?”

As I turned around, she reached over and mussed up my hair, stuck her tongue out at me, and said jokingly “You know how I said I was sorry, and called you ‘sir’? I was lying. LYING! And when I was six years old and was bad, my 85 year old grandmother spanked me harder than you did!” She smiled and laughed, back to her normal jokester persona, but this time around, is setting the stage to deserve her next spanking.

“What am I going to do with you?” I sighed. We smiled at each other. I knew we’d be working late again tomorrow.