13 - The Headmaster Gets His

“So, what’s it gonna be? Losing your job? Or turned over my knee for a brutal spanking?”

“A brutal spanking, hmm?” I asked, looking her up and down before returning to her eyes.

“No mercy,” she replied happily.

“And a paddling as well?”

“Definitely,” she replied, with a sinister smile. “You may be able to convince me not to use the strap, depending on how you, shall we say … handle things?”

“Well, in that case …”

“I hoped you’d see it my way,” she said before I’d finished my statement and reached up to begin unbuttoning my shirt. Once open, she pulled it out of my pants and pushed it over my shoulders and off.  Revealing my chest was certainly not as exciting as hers, but she acted like it was and, placing her hands on my chest, rubbed it all over, with particular attention to my nipples, which she pinched and twisted, inflicting delightful pain.

With one hand under my chin and the other still caressing my chest, she said, “I suspect you can tell by now, that I’ve wanted to do this for a very long time! Thank you so much for misbehaving in such a way as to give me this opportunity! Now, my naughty boy, it's time to take your pants down for your punishment! A good, hard spanking on your naughty … naked … bottom!”

“Yes, Tina.”

“I think, under the circumstances, you should be calling me Headmistress,” she said, her face just inches from mine.

“Yes, Headmistress,” I complied.

“Good!” Grabbing the waist of my pants with one hand, she opened the button and lowered the zipper with the other. Sliding her hands to my sides, she pulled my pants down over my hips, and let them go. As they fell down my legs, to bunch up just below my knees, she commented on my bikini briefs.

“Ooo, look at these sexy little undies! I bet you had some other plans for tonight, hmm? Oh well. Instead, you’ll be here, over my knee, getting a severe spanking!” Placing her hand right on the bulge between my legs, she added, “Oh, and this will probably go to waste as well.”

Her hands slid over the smooth fabric covering my cheeks as she stared into my eyes. Bringing her hands back to my hips, she turned me toward the desk, and, pushing on my back, bent me over and spanked me hard, five or six times across my lower cheeks.

“I couldn’t resist giving you a few spanks on your sexy, little undies, but that’s about all you’ll be getting with their protection!” Taking hold of my wrist, she led me around the desk to the chairs. “Stand right here,” she said, sitting down and placing me directly in front to face her. “So, just like the students, I want you to ask me for your punishment; tell me why you’re getting punished and how you are to be punished.”

“Please punish me, Headmistress. I haven’t been following the school’s rules for spanking our students when they’ve earned it, and so I deserve to be punished, spanked for my behavior,” I said as the bulge in my briefs grew.

“And how should you be spanked, Mark?”

“Taken over your knee, Headmistress, with my pants down, for a good spanking on my bare bottom!”

“I don’t know whether this will be a good spanking or not,” she said, invoking my definition of a good spanking, “but you will be properly, and thoroughly, spanked before I’m through with you! Now, get over my knee!” I laid myself across her firm thighs, feeling the elastic of her garter straps as I settled in. My anticipation was reaching a fever pitch as I waited for her to begin.

“I’m ready for my spanking, Headmistress,” I said, hoping to prompt some action, successfully since she yanked my underwear down just below my cheeks. 

“Good! So am I!” she said as she let go of my underwear and started spanking nice and hard across both cheeks. Sometimes with someone new, it’ll take a while for each to figure out the other’s limits, the result of which is lighter spanking, until one gets a feel for what can be withstood, to which my usual reaction is to try to encourage harder spanks.

Tina knew exactly the right place to begin, which meant I was feeling the delicious pain of a good spanking, with the first strokes of her hand. Even the ones on my underwear had been good and hard, but now with my pants down and across her knee, she had me bouncing within the first twenty.

“Oh! Oww!! Mmm,” I cried, her hand beating out a rhythm on my naked cheeks.

“Oh, does that hurt?” she taunted, “Am I hurting your poor little bottom?”

“Yes, Headmistress! Oww! It hurts a lot!” I said, not telling her how much I wanted it to hurt. Another beginner’s problem I didn’t have to put up with, was giving only a few spanks at a time; again, testing limits. Once Tina started, she didn’t stop until at least thirty good hard spanks had been delivered to my bare bottom.

“Good! I don’t have to tell you how it’s supposed to hurt. You know that all too well! And so, you also know that it’s going to hurt a lot more before we’re done here.” Tina was into this scene completely, despite her stated preference for getting spanked, and the desire on her face made me wonder just how wet her panties were already.

“Oww! Yes, Headmistress. I know.”

She continued spanking in groups of thirty to fifty spanks before she’d rest, and whatever pattern she started with, she’d continue until a rest came. If she started across both cheeks, she’d continue that way. If she alternated cheeks, giving five on one cheek and five on the other, all in one spot, she’d stick with that pattern until a pause came. Initially, she kept her hands off my bottom during the pauses, but gradually she began squeezing and rubbing my tortured buns.

After at least a couple of hundred spanks, she suddenly pulled my underwear back up and told me to stand up. She got up from the chair as soon as she was free to and walked behind the desk.

“Hairbrush in the top drawer?” she asked as she pulled the drawer open and found the wooden brush with the large rectangular back, essentially a small wooden paddle. Holding it up and slapping it against her palm a few times, she looked for my reaction, which was a barely contained smile. “I don’t think you’ll be smiling when you feel this on your behind! Oh, and I should take this out as well,” she said, laying the long wooden paddle on the desk.

She returned to the chair and ordered me back in position while pulling me over her knee at the same time. Wasting no time, she yanked my pants down and hit me with the brush. Not large enough to span across cheeks, she used it on one cheek at a time. Knowing how much more the hairbrush would hurt, she did back off a bit at first, but I gave her enough clues to get her swatting my bottom with a suitable intensity pretty quickly.

“Ow! Ow! Owww!” I said to three particularly hard swats that finished off a series. I couldn’t imagine my first spanking after a long hiatus going any better. I wouldn’t call the pain intense, yet, but it was getting there quickly, being a bit out of practice.

“Ooo, now that’s the shade of red I like to see on a naughty boy’s bottom when I’m spanking him! Hurts a little more than my hand, doesn’t it?”

“Yes, Headmistress, quite a bit more!” I said, giving her the satisfaction of knowing she was spanking me quite hard.

“Perfect!” she said with pride as she rubbed my cheeks more soothingly and sensually than before. “We’ve only just started with the hairbrush, and there’s still the paddle! Maybe even the strap!” she threatened.

“Headmistress, you said I might avoid the strap depending on how I handled my spanking,” I reminded her.

“No, I said you may avoid the strap depending on how you handle ‘things’, not how you handle your spanking,” she corrected.

“I don’t understand, Headmistress.”

“You will … in time,” she replied as the hairbrush was again applied vigorously to my sore bottom. After another two or three rounds with the hairbrush, my cheeks were beginning to numb to the pain. Sensing this, she paused again.

“Ohhh, my bottom is so sore, Headmistress!” I complained in a satisfied way.

“Oh, and it’s going be so much sorer by the time I’m done with you! Naughty boys need to have their bottoms spanked and paddled hard! You deserve to have your bottom spanked, don’t you?”

“Yes, Headmistress.”

“Yes, what?” she countered.

“Yes, I deserve to have my bottom spanked, Headmistress!”

“That’s better,” she said as she resumed spanking, but at a slower, almost casual pace. “Now, in addition to giving a certain student hand spankings on her bare bottom, during which your hand touches much more than just her firm, young, shapely bottom, I understand she also receives a special kind of … tongue lashing, shall we say?”

“I’m not sure what you mean, Headmistress.”

“Don’t you?” she asked as two hard swats were delivered to each cheek. “I’m told that when you used your tongue in certain ways with this sweet, young student of ours, she was quite … enlightened! And that she comes rather quickly to an extraordinary conclusion.” With some of the best double entendre I’d ever heard, I wanted to be equally clever in the way I replied.

“Um, I think I understand now, Headmistress. Would you like me to apply my tongue to your situation? To see if you come as quickly to a similar conclusion?”

She smiled broadly, saying, “I believe you do understand, Mark. Yes, I would like to have your tongue applied to my … situation, did you call it? And if I come as quickly to the same conclusion as our naughty, young student, you may avoid the strapping I was planning to give you.” As though to retain control over the situation, she gave me at least twenty very hard swats with the brush on alternate cheeks, putting a nice sting into them before letting me get up.

“May I get up, Headmistress?”

“Yes, you may, but a word of warning. We’re not nearly done with your spanking yet. You may reduce the severity of the spanking still to come if you please me, but you won’t avoid at least as much spanking as you’ve received so far! Understand?”

“Yes, Headmistress,” I said, looking her in the eye as I got up off her lap, pulling my underwear up again as I stood. Sliding her body out to the edge of the chair and spreading her legs made ultra clear what we’d talked about with hidden and double meanings. I was going to lick her pussy until she came, plain and simple.

As I knelt between her legs, I decided I didn’t want to keep up the clever double-speak, and if I said anything at all, while my face was stuffed in her crotch, I wanted it to be raw and dirty. I placed my hands on her thighs and kissed my way up them both, to a point just before brushing the tight, black lace covering her pungent pussy, with my lips.

“Headmistress, may I speak frankly while I pleasure your delicious femininity?”

“If by that you mean graphically, sexual language to describe what you see and do, by all means, be as graphic, dirty as you please. As long as you show me the proper respect when you’re back across my knee for your next spanking.”

“Yes, Headmistress, I understand. And now, if you please, I am going to finger and lick your hot, wet pussy until you can’t stand it anymore!”

Sliding my fingertips up the inside of her thigh, and moving around to the bottom, my mouth followed, ending up planted on the moist crotch of her tight panties. She moaned as I nibbled at her steamy lips through the coarse lace fabric. With my hands on her bottom, I pulled us together, increasing the pressure of my face in her crotch. I hooked my fingers into the waist of her panties and started to pull them down, but I was going to need her to lift herself off the chair so I could get them out from under her.

“Headmistress, I need to get these panties off, so I can delve into your steamy slit!”

Rather than just lifting herself, she slowly stood up, leaving me kneeling between her legs. I moved back slightly, so she could bring her legs together and allow me to pull them down and off. Still having her panties hooked on my fingers, I first pulled them down over her perfect ass and then slid my fingers around front to slowly unveil her equally perfect pussy.

I love the way a woman’s shaved pussy looks, with a pronounced slit that closes up, hiding all the delicate bits when her legs are together and when a woman’s crotch forms a perfect letter ‘Y’ with the base being the crease between her thighs and the upper part formed by the triangle of her mons and pussy. A nice, tight slit, as I described, adds another line between the uprights of the ‘Y’, like an upside-down ‘peace sign’, I’d once observed.

I had not yet seen Tina’s pussy in this position, so when this specimen of freshly shaved, smooth, wet womanhood revealed itself, I couldn’t help but press my face to it, kissing at first, but then slipping my tongue into that perfectly straight slit formed by her moist, meaty lips. It was my turn to moan, and I pulled her to me again to press my face harder into her delicious little ‘peace sign’.

Backing off a bit, I recovered the panties I’d left banded about her thighs and continued pulling them down to her ankles, where she lifted each foot in turn, so I could remove them entirely. After lifting her feet, she put them back down a good two feet apart. As I kneeled before her, I looked up to take in the whole sight of her fabulous body in her bra, garter, and stockings and smiled in appreciation.

Smiling back, she bent slightly, took my face in her hands, and caressed my cheeks lightly, while also pulling me up out of my sitting/kneeling position. Stepping forward with legs even further apart, I was now effectively underneath her as she pulled my face into her crotch and, squatting ever so slightly, pressed herself against my face, closing her thighs enough that I could feel their silky-smooth flesh against my cheeks. Soft moans and gasps escaped her lips as she ground her slippery wet pussy against my face, and I explored my new house of worship.

This was a new kind of face sitting that I could learn to love! Reaching around, and grabbing a fistful of soft, firm butt cheek, I pulled myself even harder into her crotch. My lips and tongue went into overdrive, as I took advantage of a position that she wouldn’t be able to maintain very long.

Nibbling her lips with mine, probing her slit, stroking her clit with my tongue, and even using my fingers to poke and stroke her perfect, wet pussy, was driving her to the brink faster than I had expected. Her knees were weakening, and she wanted to sit down, so I helped her, guiding her into the chair and positioning her right at the edge, with her legs spread wide.

“Such a delicious pussy, Headmistress! I think you are going to cum very soon!” I said before diving back into her hot, steamy cunt. Using fingers and tongue, I rubbed, licked, caressed, sucked, and nibbled everything in her crotch, including her tight, little anus, that I slipped a fingertip into after borrowing some lubrication from her pussy, which seemed to shift her into overdrive as well.

Suddenly her body stiffened. She spread her legs as wide as possible, signaling me to step it up further, when she came explosively, drenching us both with her juice.

“Ooo, was it good, Headmistress?” I asked as I ran my fingers lightly over her heaving body.

“Mmm, thank you, Headmaster!” she purred, mistakenly using my title instead of my name, or my ‘naughty, little boy’ honorific. I softly caressed her smooth, firm thighs as she regained her composure.

“I’m glad you liked it! I enjoyed it too!” I said, standing up, which made the bulge in my crotch that much more obvious.

“Yes, I can see that!” she said, her eyes on my crotch, “but unfortunately for you, your spanking isn’t finished! Over here,” she commanded, pointing to the floor at her right side.

“Yes, Headmistress,” I said, as I moved to her side.

“Pants down, naughty boy!” she said, pulling my underwear down to my knees, my hard cock springing out like a Jack-in-the-box. “Now, over my knee,” she said, guiding me across her lap so that my dick was between her slightly spread thighs. This was different than before. I was pitched forward more, and I found my face nearly on the floor, but when she closed her thighs, clamping my hard cock between them, I knew what she was up to.

“Now, let’s give this naughty, little butt a good spanking,” she said, emphasizing the word ‘good’ as she began with her hand again. She spanked hard, very hard, like she had something to prove, but without the intense pace from before, while mixing in a few strokes and squeezes of my cheeks in with the spanks.

“Mmm, such a naughty boy!” she scolded. “Tries to get out of his spanking by licking my pussy and making me cum! But I know what you’re up to, and I’m still gonna give you a good, hard spanking!” She could tell from my reaction that I enjoyed her spanking talk and continued scolding. “I know how to take care of naughty boys!” she said, her thighs squeezing together, milking my hard cock. “Naughty boys end up over my knee, with their pants down, getting spanked good and hard on their bare bottoms!” 

I was close to coming now myself, and sensing it; she stepped everything up a few notches. Bouncing me on her knee had the intended effect of fucking her shapely thighs, which also led to harder, faster spanking and continued sexy scolding. “My naughty boys always have a sore, red bottom by the time I’m done with them! Ooo, and your bottom is nice and red, and I’ll bet it’s quite sore, but not enough!” she cried as the spanking finally pushed me over the edge, shooting all over the floor. 

While she couldn’t see it, she could certainly feel it in my response, and though she didn’t stop spanking, she toned it way down using her left hand to rub my burning buns. She kept it up even as I calmed down and quickly started ramping it up by picking up the hairbrush again, which added an intense sting to my numbing cheeks.

“You know,” she said as she fell into a slow, but hard rhythm, “I’m still not even close to being done with you! You still have a good bit of spanking and a good, hard paddling to come!” Using the hairbrush in her right hand and the palm of her left, the spanking gradually increased in speed and intensity, with two hands beating my bottom. “Mmm, your cheeks are nice and red, but I want a nice, deep shade of crimson on this butt before I’m done spanking it!!”

“Yes, Headmistress,” was all I could say to acknowledge her threats. “Perhaps Headmistress would like to take a break? I’d be happy to use my tongue on your perfect, little pussy to make you cum again?” I offered.

“I bet you would! Well, you’re not getting me to stop that easily.” She spanked harder and harder, and for a while, I’d feel the sting, but it would diminish as my cheeks numbed even more. “I think I will have your face between my legs again, but only all the spanking is done!” She kept it up and, spreading the swats with the hairbrush around, managed to find some spots to spank that I reacted to.

“Oww!” I reacted to a particularly hard smack on my lower left cheek.

“Yeah! That’s better!! Spankings are supposed to hurt!” she scolded. “I’m gonna make sure your whole butt hurts before we take a pussy break! And then it's time for the paddle!”

“Oh, Headmistress! You’re spanking me so hard!! My poor bottom is so sore!”

“Good!” she said, ignoring my pleas, just as I wanted her to, and continued spanking me with the hairbrush. The brush struck everywhere, and when she’d find a vulnerable spot, she’d concentrate on it with a flurry of swats. Just when I thought I might not be able to take any more, she stopped.

“There! Now you’re ready for the paddle! You can get up, but I want you bent over the end of the desk.”