7 - Mrs. Cooper Strikes Again

At work the next day, I didn’t go out of my way to see her or avoid her, but it was well into the afternoon when we caught sight of each other in the hallway. She gave me a cute, shy smile that made me feel better. I was honestly worried about how she might think about what we’d done, with ‘morning after’ regrets, worries, etc. If her smile was any indication, my fears were unfounded.

I didn’t see her again for the rest of the day, or the following day, which wasn’t unusual. I imagined she was taking the same approach as I was, acting no differently than before our fabulous role play, though I had hoped that by the weekend, she would have tried to make contact, but that was not to be.

I thought of her often during the weekend, wondering if I should make a move. Maybe I should try to call her? I finally decided that for at least a few more days, I’d wait for her. Her story was unusual enough that I thought she could still be very nervous about all this and not know what she wanted to do next.

When I remembered her hot body draped across my knee, her sumptuous ass, her schoolgirl outfit and attitude, and most importantly, spanking her, I envisioned our relationship staying that way, with me as the spanker and her as the spankee. Normally, in cases where I knew a girl was into switching, my imagination would tend to steer towards me being on the receiving end, but with Justina, I was quite comfortable continuing as her headmaster, her stern daddy, or her punishing husband, turning her beautiful bottom nice and red, while she squirmed in ecstasy across my lap. That doesn’t mean I didn’t think about her spanking me at all, but most of my fantasies ended with her having the red bottom, not me.

I went to work on Monday, just dying to at least talk to her again and maybe share a memory or two of the scene we played out. I was still going to give her a couple of days to come to me, but I wouldn’t let the whole week go by without talking to her if she didn’t.

Around mid-morning, I was in her department talking to one of her co-workers, when I caught a quick glimpse of her heading out the other door. She didn’t look up at me, though I’m sure she would have recognized my voice as I carried on with my discussion. I finished a few minutes later, and leaving the department, I almost expected to see her in the hall, perhaps waiting for me. I was disappointed again when it didn’t turn out that way.

My disappointment didn’t last though, as upon returning to my office, I found an envelope marked ‘Personal’. Opening it, there was another smaller envelope inside addressed to 'Headmaster'. My heart started beating faster, as I knew this couldn’t be anything but good.

I slit open the envelope that was identical to the one she’d handed me from ‘Mrs. Cooper’, certain that it contained what amounted to an invitation to give her another good spanking. She must have written it over the weekend, as she wouldn’t have those envelopes or that paper here in the office. She must have written it at home and brought it in. A huge smile spread on my face as I read the note …

Headmaster,

For the past week, Justina has been a model student, thanks no doubt to your handling of last week’s situation. I’ve been very pleased with her behavior and performance.

Unfortunately, that pleasure didn’t last, as I caught Justina in very similar circumstances to those I had reported to you before, except that this time it was rather obvious what she was doing with her hand up her skirt. I have permanently moved her seat to the front of my class to discourage such disgusting behavior, but I don’t believe that alone will be enough to get her mind back on her studies.

I would be very appreciative if you would, again, take the situation ‘in hand’ to be sure she understands that such behavior is unacceptable under any circumstances.

I understand you haven’t been in the office the last few days, which is why I delivered this note in this way. Linda tells me you’ll be returning to your office on Monday afternoon, before 5:00 pm. I hope you don’t mind that I have arranged for Justina to meet you there at 5:00 pm, hopefully allowing you some time to get settled before she arrives.

I hope you don’t think it presumptuous of me to have arranged this without consulting you first, but I’m sure you’ll recognize the need for timely discipline if she is to succeed in her studies.

Thank you in advance,

Mrs. Cooper.

Looking up from my reading and still smiling, I saw Justina in the hallway looking at me and, upon seeing my reaction, smiled broadly as well. She didn’t come in, just acknowledged that she’d seen my reaction and went on her way.

Going back over the note, I picked up what I needed to know to get back into my role as headmaster. First, I was to meet Justina today at five o’clock in ‘my’ office. I needed to get there earlier so that I could assume my role and have Justina enter the scenario as she had last time.

Second, she had clearly indicated that she wanted this spanking to be more intense than the last by accusing herself of the very thing I told her would earn her a ‘considerably more severe’ punishment. I had only realized on my way home last time, that I’d threatened to paddle her, but had never actually done it, which may be the reason she was upping the ante this time, so this time I needed to work paddling into our play.

During the weekend, my thoughts also included a variety of scenarios and options, and I was now sure which one I wanted to use. I only hoped she would appreciate it, as it would become a departure from the naughty schoolgirl-gets-punished theme as well as introducing some other sexual elements, at the very least fingering her to orgasm. I didn’t expect that would be a problem, since she had realized before, that I might be expecting something more, even though she wasn’t ready to give it. I thought that her initiation of another meeting, and escalating the level of punishment was more than a hint that we’d take it all somewhat further.

I found it difficult to concentrate on my work for the balance of the day, as thoughts of Justina, and visions of her beautiful bottom filled my head. I re-read the note often, with a swelling in my pants each time. I played the scene out in my mind repeatedly, hoping that she would go along with the escalation I had planned and that I wouldn’t have to take care of myself at home afterward.

8 - A Good Spanking!

I would have liked to go home and change clothes, but there just wasn’t time. I wanted to be at her apartment by about a quarter to five, to prepare both physically and mentally, and it’s difficult for me to leave before five.

I managed to get out a little after four-thirty and found my way to her apartment without difficulty. Her car was in the same parking space as last time. My heart started beating harder in anticipation.  It was almost four-fifty when I made my way upstairs to her apartment and found a note folded and tacked to the door …

Headmaster,

FYI … Not sure if you’re aware that you have a student discipline issue to deal with at 5:00 PM. See you tomorrow. Welcome back!

Linda

Presumably, Linda was my secretary or assistant, and I imagined Justina was borrowing the name of a buxom, young girl who filled in as my secretary in the late afternoon when my regular assistant went home. For just a moment, I imagined Linda doing something worthy of a good spanking, envisioning her plump bottom over one knee and her gigantic tits over the other, but I quickly returned to thoughts of my naughty schoolgirl, Justina.

The door was ajar, so between that and the note, I assumed that I should enter on my own. “Linda?” I called out to signal my presence and stay in my role. “I’m back!” I made my way to my office and went inside. It looked the way it had last time, with the chairs moved back to their prior positions. I went to the desk and put my briefcase down. I’d brought it only as a prop. I sat down and went through the desk drawers to find her paddles. I found the short round one, perfect for application to a single cheek, especially one as perfectly round as Justina’s.

I moved the chairs into position; one right in the middle of the room that I’d sit in and the other close by on which I laid the paddle. Since I already knew the nature of Justina’s bad behavior, and that it is something I specifically warned her about, it’s fair to assume that I could have decided her punishment beforehand and prepared myself for it.

I looked at my watch and saw it was almost five, so I went to sit at my desk and took some papers from my briefcase that I would be working on. I quickly arranged my hard-on to hide it as best I could, although later, a sizeable bulge in my pants would play well into the scene I had in mind. As I was practically watching the seconds go by, I knew that it was a little before five when she knocked on the door, and I hoped that showed some excitement and impatience to get this little play going.

“Come in,” I said in answer to her knock. The door opened, and Justina came in dressed identically to last time, although she looked a little better put together, perhaps having had more time to dress. I’m guessing she changed her makeup to look a little more youthful and a little ‘slutty’ I noticed.

“Good afternoon, Headmaster,” she said demurely, “Mrs. Cooper sent me to y …”

“I know why you’re here, Justina. I got a note from Mrs. Cooper.”

“Oh, so I guess you know the situation,” she replied, taking note of the chair and the waiting paddle. “May I ask what she told you, or what she accused me of, sir?”

I stood up to emphasize my statement. “She told me she’d caught you doing exactly what I warned you about last time. You do remember my warning about a more severe punishment if I were to hear that accusation again?”

“Yes, sir, I do. Will you tell me what she said I did?”

“That’s fair, I suppose. She said you had your hand in your panties and were masturbating right in her class.”

“She said that?”

“In so many words. Do you deny it?”

“Well, it’s not true, but I doubt if anything I say will matter.”

“You actually have an explanation for this behavior?” I said with a smile.

“Not one that would make any sense to you, so you might as well just spank me, paddle me, and get it over with,” she finished defiantly.

“I’m willing to listen to an explanation, Justina.”

“I’m sorry, sir, but I don’t think I can explain it in any way that you would understand, and even if I could, I doubt it would change the outcome, so we may as well just get on with it … sir.” She moved over towards the chairs, anticipating my next move correctly.

I made my way to the open chair and sat down. “Over my knee, young lady,” I commanded. She moved to my side and gently draped herself across my knee. I hoped she could feel the bulge in my pants and, if so, would also feel it growing. As she wiggled herself into a comfortable position, I heard a soft moan of pleasure, not of fear or anticipation. “Are you okay?” I asked.

“Um, yes sir, I’m … um, okay. I mean, I’m ready,” she said in a voice trying to mask her desire. Was she just not playing her part well, or was that intentional, I wondered? Lifting her skirt to expose those tight, white panties prompted more desirous sounds and motions. It was as though she knew the script I had in my head and was playing right into it.

Placing a hand on each panty-covered cheek, I touched and squeezed them ever so lightly. I could stare at that beautiful bottom in tight panties for hours, but the longer I delayed, the longer I had to wait to see it naked.

“Are you ready for your punishment, Justina?” I asked with a teasing tone to my voice, yet still officiously.

“Yes, sir. I’m sorry for my … behavior. Please give me a spanking, sir?” she said as she turned to look back at me. With the first smack, she turned to look at the floor again, and as I continued, her body swayed and squirmed as though inviting each spank. I spanked slowly, but continuously, not stopping until I’d delivered a good forty or fifty smacks to alternating cheeks. When I stopped, she clearly wished I hadn’t.

“Oh, sir, you’re spanking me so much harder than last time!” She wanted it to sound like a complaint, but it didn’t.

“I warned you about how severe it would be!”

“Yes, you did, sir. I’m sorry.”

“As usual, you consider the ramifications of your behavior only too late to do anything about it,” I scolded, as I slipped my fingers into the waist of her panties. “We’ll be taking these down sooner as well.” As the white fabric glided across the tight, round cheeks, I felt my crotch swell in appreciation. Justina looked sideways at me with a small smile that said, ‘I felt that’.

With her panties down at mid-thigh, I again had a view of the most beautiful bottom I’d seen in a long time, perhaps ever. She spread her legs a little to give me a narrow glimpse of the slick, wet folds of flesh between, and I was pretty sure that we’d be going beyond spanking this time.

As I resumed spanking, a little softer and with prolonged contact with her silky, smooth orbs, she moaned louder than before. “Ohh, why am I always getting spanked?”

“Because you’re such a naughty girl!” I said, noting that the use of the word naughty often really meant sexy and promiscuous.

“I don’t mean to be … really, I don’t. I’m normally a really good girl. If only I could just …”

“Just what, Justina?”

“Ohh, nothing. Never mind! Owww!” she cried, as I laid on a few good, hard ones. I had been spanking her through that whole discussion, but now paused for a minute. I intentionally didn’t put my hands on her hot, pink cheeks even though I wanted to. It was as though they were calling to me, saying, ‘Squeeze me!’, but I resisted because I decided it was time to start the script I had planned. She seemed to be playing along with it even though she could have no idea what I’d planned, and she’d just given me the segue I needed.

“You have put yourself in this position quite a bit lately. You’ve gotten, what … five? ... six? spankings in the last two months or so?”

“Six, sir, since the break, and that was about seven weeks ago?”

“Really? So, almost every week!?”

“Yes, sir. Believe me, my bottom remembers!” she said, with a pained smile, adding a little humor to the situation.

“Well, your bottom is going to remember this spanking for a bit longer than the last one, and to make sure that’s the case, I think it’s time you were paddled on your bare bottom.”

“Oh please, sir, don’t paddle me! Give me twice as many spanks if you have to!”

“Justina, I’ll say this only once. Get up, go to my desk, and present yourself for a paddling.”

“Yes, sir,” she said meekly as she scrambled off my lap and moved over to the desk, rubbing her hot bottom in a tantalizing manner. Standing at the front, she shifted her legs back and forth to allow her panties to fall to her ankles. She managed to get one foot free from them and left them wrapped around the other ankle. Lifting her skirt, she bent over, placed her forearms on the desk, and looked back at me, telling me with her eyes that she was ready. I moved to her side, placed a hand on her back as though holding her in place, and resumed spanking with my hand.

“Would it surprise you to know, Justina, that there are girls in this school who intentionally misbehave, hoping they’ll be sent to my office for a spanking?” I asked as I continued spanking hard enough to sting but not hurt.

“I … I don’t understand, sir. Why would they …”, she asked, when I’d paused.

“Obviously, they like getting spanked, and the only way they can get spanked is to misbehave,” I interrupted.

“That is a surprise, sir,” she said, “Is there a reason why you’re telling me this?”

“Well, we couldn’t have them continually misbehaving, which affected their work and the class, so we worked out a plan that’s better for everyone - the student, the teacher, and me,” I said, as I picked up the paddle, her eyes glued to it as I slapped it against my palm a few times.

“That’s interesting, but I still don’t … OWW … see …”  I stopped her with a couple of good hard swats across her seat with the paddle.

“See, we made a deal; the students and me. If they got through the week without any problems, then I would give them the spanking they wanted so badly.” I gave her a swat on each cheek.

“Oww! … okay, but I still don’t understand why you’re telling me about this, sir?”

“They behaved themselves, so the teacher is happy. They got better grades because they weren’t always disrupting their studies, and they got a good spanking at the end of the week. See? Everybody wins!” Before she could interrupt me, I asked, “Might you be one of those girls, Justina? Have you ever had a good spanking?”

“I don’t know. Um, no, I don’t think I’ve ever had a good spanking,” she replied with similar emphasis on the word ‘good’ and looked back at me with a hint of a smile.

“Would you like to try it?”

“Um, I guess … okay, it can’t be any worse than this, can it, sir?"

“Oh no, I think you’ll find it’s much better,” I said, as I put the paddle down. Pulling her to my side, I put both hands on her cheeks and began kneading the silky flesh, allowing fingers to stray into her crack and gradually down between her legs. She loosened up almost immediately, even when I mixed a few spanks in with the massaging caresses of her beautiful bottom.

“Oh, sir!" she cried, reacting to the mixture of probing fingers and spanking. My left hand, which had remained on top, squeezing and stroking her cheeks and thighs, slid underneath, across her tummy, and between her legs, where the humidity could be felt even before my fingers slid into her steamy slit. She moaned again as I stimulated her clit and her ass at the same time.

“You’re not just a naughty girl, are you? You just want to be punished, spanked on your bare bottom!” I accused, at the same time as I spanked each cheek, in turn, at least a half dozen times. I hoped to transition her to someone who admits she wants to be spanked, instead of pretending she doesn’t like it.

I’ve always preferred giving and receiving spankings that were desired as opposed to pretending not to. One can still scold a bad boy or girl, tell them how naughty they are and how badly they need to be punished, spanked, and paddled, but my enjoyment increases dramatically when one can admit how naughty they are and how much they need and want to be spanked. I was trying to push Justina to that point now.

“Sir? You said everyone’s happy and explained how both the teacher and student benefit from your deal, but you didn’t say how you benefit, sir?”

“I’m surprised you haven’t figured that out. Perhaps it isn’t obvious how much I enjoy spanking naughty little girls, and under my plan, I could have several naughty girls in need of a good spanking every week instead of waiting for the teachers to send them to me. A naughty … girl … who wants … to be spanked … like you,” I said, emphasizing each word or phrase with a good full palm smack to each cheek.

“Ohh, sir!! Oh my God … ow … oww!” she cried, getting close to the turning point.

“Yes, bad girls need to have their naughty, little bottoms spanked, don’t they? Or maybe you’d prefer to have your ass spanked? Or your butt? Hmm? What do you call your beautiful, round bottom when it’s being spanked, Justina?” I knew what the answer was, but I wanted her to tell me.

“My, my hiney, sir,” she said meekly.

“Well then, you need to have your hiney spanked, don’t you? Do you want me to spank your hiney, Justina?”

“Yes! Yes, sir! Spank my hiney! Give my hiney a good spanking!!” she cried, as she passed the tipping point from punishment to sexual spanking. I ramped up the excitement, slipping one finger inside her slippery slit. She spread her legs a bit, allowing my finger to penetrate further. Finger fucking her with one hand and spanking her just hard enough with the other was accelerating her trip to an orgasm. “Ohh, I’m such a naughty girl, sir! I deserve to have my hiney spanked!”

“Yes, naughty girls need spankings! … spankings on their naughty, naked hineys!” I said as I slipped another finger inside her dripping hole.

“Oh! Ohh! Ohh!” she cried, as her climax was imminent. Up on her toes, with her bright red rump thrust out in invitation for more spanking and spreading her legs to allow another finger in her pussy, she cried out in ecstasy as the wave of pleasure washed over her, and she collapsed on the desktop, slowly regaining her breath with shuddering gasps.

I reached for the paddle, just inches from her face. Her eyes followed it as I picked it up, and a smile grew as she looked toward me. The combination of her smile and a gentle squirming motion on the desktop told me she wanted more, and I wouldn’t keep her waiting.

“I bet you’ll want to be spanked again, won’t you?” I asked as I started beating out a soft, but steady rhythm on her bright pink bottom.

“Yes, sir! I can be a good girl. You’ll see!” she replied, before resuming her soft moans and cries in response to the slapping paddle.

“Yes, I think I will see you behave like the studious, attentive girl you were before you were spanked the first time. That’s when the trouble started, isn’t it, Justina?” While gradually ramping up the force of the swats to alternating cheeks, I slowly knelt behind her until my face was level with her hot bottom. “You were fine until you got that first spanking, after which you were confused. It’s not supposed to feel good, but you couldn’t deny that it had really aroused you, could you?”

I pressed my face into and kissed one delicious cheek while still swatting the other with my paddle. “Maybe you went home and pleasured yourself while thinking about your spanking? Or maybe not, but within a few weeks, you knew you had to have it again! Another spanking on your bare hiney, to see if it felt the same way”.

I switched the paddle to my other hand and repeated the kiss on the other cheek, with a little tongue at the end. I continued as she moaned in appreciation.

“… and of course, it did, and this time you went someplace where you could rub your wet pussy until you came.”

As she moaned in response, I leaned forward and, with my tongue outstretched, licked her glistening slit from bottom to top. A sharp intake of breath, and a suddenly arched back signaled her approval and incredible desire. As the shudders subsided, she spread her legs a bit wider, clearly telling me she wanted more.

I put the paddle down and began spanking with my hands again, both hands beating out a rhythm on her taut bongos. After at least twenty on each drum, I again leaned forward, planted my hungry mouth over her entire pussy, and sucked, licked, and nibbled the tender lips until she was writhing uncontrollably on the desktop.

“Oh my God, sir! Spank me! Spank me hard!” she cried, as her body stiffened, and the beginning of another climax approached. My mouth planted firmly in her crotch, held her in place, freeing my hands to spank her randomly, but hard. Each smack brought louder and louder cries as her orgasm approached and came, leaving her crotch and my face coated in her juices, while her lungs gasped for the air she’d denied them with the short, shallow breaths leading up to her climax.

I got up to get a tissue from my briefcase to wipe my face. Justina remained in position as her body almost slithered on the desktop.

“I’m such a naughty girl, sir! I’m sorry you have to spank me all the time. I’ll be a good girl from now on,” she said, as her eyes followed me back to a seating position beside her on the desk.

“I’m sure you will,” I said, as I stroked her red, hot mounds with my right hand. Drawing my fingernails across her tender cheeks drew a gasp that told me she probably wanted more. “But I suspect that even now, you want to be spanked again, don’t you!?” I was squeezing her hot buns and stroking her pussy, to which she responded with only encouraging sighs and groans when I asked, “Do you know what else naughty girls need when they’re bent over like this?”

She replied by placing her hand right on my hardened shaft and said, “One of these stuck up inside them, sir?” She was smiling when our eyes met.

“I knew you were a very smart girl!”

“Am I going to get spanked again while you fuck me, sir?” she asked, emphasizing the word and showing she wanted to be fucked hard.

“Well, that depends on whether you need additional motivation to behave yourself for the next week or so.”

“Oh yes, sir! Give me a good spanking, and make me be a good girl while you fuck me!”

I stood up and had my pants open and down around my ankles in no time, my stiff cock waving like a beam without its sail in front of me. As I approached her slippery slit, I spanked her good and hard on each cheek, just to ratchet the tension up a notch or two. She raised her bottom as she stretched her legs fully, but remained bent over the desk with her palms flat on the surface and pushed her butt out as an invitation to spank even harder.

Spanking with my left hand, my right took my cock in hand and rubbed it up and down her slit, from her tight butthole to her clit and back, hearing sighs begging for penetration. After a couple more circuits, my cock homed in on her slippery wet pussy and slid in easily and deeply. One long “Ohhhh” was all she said as I slid in right up to my limit, after which I said the same.

Knowing I would cum quickly, I teased her by pulling out again and using my fingers and thumb of one hand to stimulate her clit and pussy, while spanking her with the other. When she cried out for my cock, I slid in again, pressing her body hard against the desk, and drew it out slowly, breathing in deeply as I went. It would take less than a dozen strokes like that to make me cum. Using my hands again, I fingered and spanked her until she begged for my cock again.

“Oh, please, sir! Please fuck me, and don’t take it out!”

“I will cum very soon if I do,” I warned.

“So will I!” she cried, “Please! Fuck me and spank me, sir!” I didn’t need to be asked twice, so I stuffed it in again to the hilt and drew it out slowly. Repeating this pattern, rammed in hard, and withdrew slowly, I also spanked her quite hard. I held on for a dozen strokes before I came explosively, and a couple of strokes later, she followed suit, after which I collapsed on top of her, feeling her beautiful breasts for the first time, with her body squirming underneath.

I stood up and felt my dick pop out of her wet pussy. I pulled my underwear and pants back up and then bent again to pull Justina’s panties up. Still bent over the desk, but resting on her elbows now, she lifted one foot to allow me to slip them back on and up her gorgeous legs. As I pulled them up tight against her crotch, I snapped the elastic against her bottom and smacked her cheeks again a couple of times. She turned around with a big smile and smoothed her skirt back over her panties.

“So, now you know what a good spanking is like!”

“Yes, sir. How will I know when I’ll get to … to be spanked again?” she asked, with the cutest look of innocence on her face.

“I’ll send a note to your last-period teacher; that’s Mrs. Cooper, isn’t it? The note will simply ask that you be sent to my office after class for positive reinforcement of your good behavior. I think she’ll be quite happy to cooperate, don’t you?”

“Oh, yes, I’m sure she will, sir. On what day do you think that will be?” she asked, clearly wanting to know now when this would all happen again.

“Fridays are a good day. Not many people are likely to be hanging around late on a Friday, so privacy is less of an issue, but I don’t know about this Friday, since it’s only a few days away. Your bottom may still be sore by then?”

“No! No, sir!” she said almost desperately, “my bottom was fine in just a couple of days last time. A little pink still, but it didn’t hurt. I should be fine again by Friday.” Her smile and bitten lower lip would have convinced me of anything at that point.

“Friday, then! Remember, you must behave perfectly. Listen to your teachers. Do all your work. I’ll be checking!”

“Yes, sir, I will. See you Friday!” She gave me a quick kiss on the cheek before turning to leave.