I take a long, long time before I speak to you. I say speak to you, and not with speak you, of course, because we’re not talking together. This isn’t a dialogue. I’m going to speak, and you’re going to listen. I might favor you with a rhetorical question, but otherwise you’re not going to talk. But you don’t need words. I know everything I need to because of the way you breathe, how your shoulders rise and fall, and the way your head tilts further forward in submission.

“I want you to know something,” I begin. My words startle you. I can tell from the way you shake at the sound of my voice. For a few moments I don’t speak. I enjoy this slow build, pulling you further apart with my teasing. Feeling the way that you yearn, eagerly, for the humiliation and punishment I’ve brought you.

I arrived twenty minutes ago. You were, as you always are when I first come in, ready for me. Kneeling on a chair you placed in the corner. Your white shirt starched, the pleated skirt mid-thigh. I always enjoyed the sight of bare skin between the end of your skirt and the tops of your argyle knee-socks.

Once I let myself in, I entered the hotel room and sat on the bed, lazily reading for ten minutes. Then, finally, I arose from my chair and approached you from behind. I let you hear as I came near. Wordlessly, I produced a large safety pin from my pocket. Taking the hem of your skirt, I pinned the back to your shirt, ensuring that your pantied bottom was now on display.

I check my watch, and after another five minutes, I approach again. This moment is the is the closest that I will come to touching you like this, so I allow you the chance to savor it. I slowly trace a finger up the seat of your white panties. It’s a dreadfully slow grazing, and nowhere near your slit, but I can still see the effect.

Slowly, very slowly, I reach the waistband of your panties. When I do, I linger a bit before proceeding. Then, my fingers slowly start to peel the white fabric down. Gradually, your bottom comes into view. When I’ve just barely exposed your bottom, I stop. This, I’ve concluded, is more humiliating than being naked. In this arrangement, your clothing highlights your nudity, increasing your exposure.

After allowing you to stew again, I approached silently. And that brings us to now. I get your attention and watch your reaction as you wait for my next words. I can almost see your ears perk up when I finally continue. “If you are an especially good girl today, I might let you beg”. This time, I can see and hear the impact; the slight, quivering moan that escapes your lips is delicious.

Stepping into you, I begin to gently scold. I had never raised my voice, never would raise it. I didn’t need to. Instead, I speak barely above a whisper, forcing you to strain to hear. Forcing my hot breath on your ear. “I know that you’ve been a very bad girl” I tell you. I can hear you struggling to keep silent. The soft, halting attempts at speaking. “You haven’t been attending to your studies. I contacted the university, and they said you had the worst attendance the last two grading periods of your entire class”.

I continue. “You’ve also not been sending me progress reports”. These were brief letters that told me how much water you had been drinking, how much sleep you had been getting, and other minutiae you struggled with by yourself. I continue to space my sentences, listening to the struggle within you as you suppress your urge to defend yourself. “I can assume that means you’re not doing what’s required of you” I conclude.

I tack on several more suspicions I have but spit them out as if they were facts. “I am sure you are behind on your bills, and I don’t even want to ask how much laundry is piled up in your dorm”. Continuing to allow the words to sink in, I stand by silently as I breathe into your ear.

Finally, I decide to show you some measure of kindness. I tell you that you can assume the position on the bed. Once you’re in the all fours position, I pull your panties down lower. I instruct you to hold your position as I spank you. I never tell you how many you’ll get, robbing you of any ability to fortify yourself. I try to make each spank harder than the last. The crack is resounding throughout the small room, and the way you have to fight against the paddle pushing you forward to maintain position is delightful.

By spank twenty-nine, I can tell you are getting worn. You’re having trouble staying still, I can hear your ragged breathing, and there is sweat on your brow. I give you a final swat, hardest of all, and listen as your sobbing begins in earnest. I barely let you start crying before I put you in the corner again, giving you time to consider your misdeeds.

During our meetings, things proceed one of two ways: either I let you beg, or I don’t. In either case, I ensure that before I leave you have been able to sob in my arms as I stroke your hair and shush you. I hold you close and tell you that you’re a good girl, and that I know you’re going to try harder now.

I didn’t always let you beg. For the first many punishments, I would spank you, give you aftercare, and then send you home. One day, however, I noticed how incredibly forlorn you looked after I had stroked your hair. It took the promise of more spankings, and several halting attempts before I was finally able get it out of you.

You desperately wanted release after our spankings. More to the point, you wanted my help in achieving that release. I considered the neediness of your pussy and came up with a solution. I would, on occasion, allow you to cum for me. But it had to be on my terms. You eagerly jumped to agree, but I made sure you were aware of what was involved.

I look at you in this moment now as you stand in the corner. The first term I came up with was the begging. If you had behaved appropriately during your spanking, I might, were I feeling merciful, let you get on your knees and beg me for a kind of orgasmic charity. This wasn’t just a pleading request, though; you needed to completely debase yourself during the begging.

From behind you, I tell you that you may beg. I see you almost jump as I take a seat in a nearby chair. Kneeling before me, I listen as you plead for release. As you beg, I hear telling me how dirty you are, how you don’t deserve it, but if I might have a morsel of pity, maybe I could let you cum.

Eventually, you run out of pleadings, and we get to the very best part. The part where you try to make me a deal. Quid pro quo. You realized soon enough that I would never let you fuck me or suck my cock. I would never allow you to see me vulnerable in that way, and you no longer beg for it.

But everything else is on the table. Every humiliating thing your sexed-up mind can think of. Kissing my shoes. Blowing the bellhop. Walking down the hallway at noon stark naked. Ordering food delivery, inviting the delivery guy in, and then offering him more tip money in exchange for the chance to lick his balls.

The begging by no means guarantees release. It’s just a solicitation for it. Many times when you have begged, I deny your request, give you aftercare, and then depart. Today is different, though, as you’ve come up with a wonderful new idea. You begged me for nearly half an hour before you finally gave it up.

You were willing to call a young man you had only just a day ago had a first date with and ask him if he would please listen to you while you came. I could see the blush, the terror in your eyes. I knew you needed this release, but I also knew that part of you hoped I would deny it.

I agreed, but only on the condition that I remain a secret member of our lustful party, and that you tell him in intimate detail about how you get off. I could see you weighing the pros and cons. Eventually, you nodded and rose to shaky feet. He answered almost immediately, and it took you almost twenty minutes to get to the point. There were a lot of stammers and stops and restarted sentences as you unlaid everything.

I cherished the heady mix of humiliation and lust you exuded when he eagerly agreed. Removing your now wet panties for you after you took the leather crop from your suitcase, I help you into position. Sliding a pillow under your hips, you spread your legs wide. Placing the phone on speaker, you lie it on your chest.

As is customary, I lie on my side next to you. Making focused eye contact with me, you finally speak. “Thank you for letting me have this”. I smile slightly when your would-be beau, thinking that you are speaking to him, stutters out a response. Finally, I nod, and you explain in explicit detail how needy your pussy is right now. How it appreciates a firm touch. How you have the crop on your spread lips. Ready. Prepared. In place to punish yourself into an orgasm you desperately need.

I can hear the agony in his voice as he groans. Finally, I nod, and you begin. The soft patting begins. I’m not sure he can hear it, but I know that he can hear your quickened breathing. Listening to your moans, I wait as you build in pleasure. Eventually, I have heard enough and whisper, urging you to spank harder. You do so, and I have little doubt he can hear the spanks now. I can tell you’re holding back, avoiding pain in lieu of pleasure. And so, I hiss in your ear, demanding you to hurt yourself.

As you do so, your moans grow pained, louder. After a moment, I warn you to reel yourself in. To not be such a wanton whore. Once, when I allowed you to do this to yourself, your moans were so loud the front desk called the room, citing a noise complaint. As punishment, I made you go down to the front desk sans panties. I ordered you to find the front desk clerk and apologize; telling them in excruciating detail what you were doing, how, and that you would try to be less of a slut in their fine establishment.

As I remind you of this, I tell you that if I have to send you to the desk again, I’ll gather your wetness on my fingers and rub it all over your face so you’ll have no idea whether they can also smell your arousal.

Eventually, you are spanking quite hard, and I can see the tears forming in your eyes. If you care about the noises you make, you don’t show it. Watching me closely, you try to read my disposition. I feign disinterest. Your guy friend is moaning loudly as you explain how wet, how close you are.

Eventually, your moans topple over into pleas. You can’t quite get it out at first, just repeating “please” over and over. And then, you beg for permission to cum. It’s a wonderful moment, seeing you like this. Right on the edge, unable to go over until I say yes. It’s made even better though because he says “yes” just as I say “no”. I can see the confusion in your wide eyes, how you almost let yourself go.

You don’t however, and I’m not sure how you were able to resist. Probably by reminding yourself that the punishment for cumming without permission is figging. Followed by an even harder spanking. Followed by repeated, hard slaps to your spread pussy with my hand until you are sobbing, begging. For me to stop, for me to slap harder, for me to let you cum again.

And so, our little trio continues our game. You spank your clit with the crop and beg me to cum, he says yes, and I tell you no. Eventually, he begs you to cum with him, and I make you and him both wait. Finally, I nod and tell you to cum for me. You fall down into an orgasm, spanking ever harder, telling him about your hard cum. I hear him groan hard and tell you the same.

I pet your head as you and he rest, and then eventually stand when the two of you begin an awkward conversation. Finally, the tension lessens, and I let myself out of the room as you both make plans with him for later in the week. Looking at me as I depart, I see you mouth a sincere “thank you”. Maybe for letting you cum. Maybe for making you call.

I’m sure I’ll find out next time.

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Based off a conversation with the always wonderful /r/Lke90

Comments and feedback always welcome.