Finishing School

Eva Monroe
11 mins read
Published over 1 year ago
Chapter 1

Finishing School

About an hour into the dinner party, I started to feel your eyes on me. Including the pre-game cocktail I’d had, I was almost done with my third drink. With you watching me, I was vaguely aware that I might be getting a little too boisterous, but your gatherings were always so livelyfull of interesting people and compelling conversation. It was easy for me to get caught up in the moment.

It wasn’t until after dessert, when we were all sipping coffee and bourbon in the living room, that I realized I was in trouble. I was talking with your neighbor, an architect from Italy who specialized in boutique hotels. He probably wasn’t as funny as I thought, but with five (or six?) drinks in me, he was utterly charming.

Mid-laughter, I caught your eye. Not only did you not return my mirth, I saw you clenching your jaw… It was never a good sign. I quickly made my excuses, untangling myself from the architect. It’s true that we’d been talking for some time, and while I couldn’t be certain that was my offense, I could at least switch gears and help clear away the last of the dishes.

Maneuvering to cross your path, I leaned in close. 

“Is everything okay?” I asked, full of innocence.

You gave me a small smile and caressed my face.

“I’ll deal with you later.” 


Your voice was sweet and gentle, but I knew better. Small offenses could be dealt with swiftly and in mixed company. Only more severe punishments had to wait until later.

For the last half hour of the party, I tried very hard to be on my best behavior. Unsure of where exactly I’d misstepped, it was hard to know if I was covering all my bases, but I was so aware of needing to be good, I was sure I’d offset your disappointment at least a little bit.

I was sure, that is, until we’d said goodbye to the last guest and you closed the door.

Turning to me, you shook your head and crossed your arms.

“Did I, um, do something wrong?” I asked, attempting humility.

“Where do I begin?” you sighed.


Leading me to the couch, you sat me down and stood over me, emphasizing your authority.

“First of all, you grumbled, scoffed, and rolled your eyes on three separate occasions when you were asked to help out this evening.”

I gulped, squirming in my seat.

“I… I did?” If I’d acted indignant like that, as you were suggesting, it was far too late for humility.

“You certainly did. And do I like it when you behave like a petulant, spoiled brat?”

Flushed with shame, I shook my head. Flashes of memory came back to me… how I’d huffed when you asked me to fetch more wine from the kitchen, not wanting to interrupt my conversation. And how when at one point you corrected me with a gentle “no elbows on the table,” I’d rolled my eyes at you as I begrudgingly complied.

“No, you don’t.”

“That’s right. I do not. Furthermore, you know how important manners are in this household,” you said, and I nodded in agreement. “And yet, you spent half of dinner with your elbows on the table and talking with your mouth full.”

I swallowed again, my eyes wide.

“I-I’m sorry, I didn’t realize

“Of course you didn’t. You were too busy swilling drinks and fawning over the architect,” you chastised. I felt my face flush.

“We were just talking-”

“Just talking. With your tits practically falling out of your sweater.

You gestured to my chest, and my gaze followed. Mortified, I saw that two of the buttons on my cardigan had come undone. Not only were you right about my tits spilling over, but even a glimpse of my lacy bra was visible.

We had a very strict agreement about how much cleavage I was allowed to show and when, and you’d reiterated the rules very clearly at the beginning of the night. You’d said I could wear the small, snug sweater, but only if I wore it buttoned all the way up.

“Oh my god, I’m so, so sorry, I had no idea…”

I moved to cover myself, but you scoffed and pulled my hands away.

“Oh it’s far too late for that, I’m afraid,” you scolded. And instead of covering me up, you tugged my sweater open further, undoing nearly all the buttons and putting my ample bosom and push-up bra on display.

Stepping back, you examined your handiwork.

“You can take the trash out, just like that. Since you like showing them off so much.”

A small whimper escaped my lips, but I stood obediently. With my shirt open, my skirt suddenly felt smaller and tighter… 

“Now would be a good time,” you teased, “before I decide leaving your tits covered by your bra isn’t necessary.”

I scurried off to the kitchen, collecting the trash that was leaning against the wall. You followed, opening the back door for me.

As I tottered down the driveway in my heels, you leaned in the doorway and watched. One of the neighbors was out walking his dog, but he was across the street… Maybe he wouldn’t see.

“Good evening!” you called out behind me, drawing the neighbor’s attention. “Nice night for it.”

The neighbor saw you first and waved, good-natured. Then he caught a glimpse of me, his eyes widening.

“A good evening to you, too,” he replied, his eyes glued to my breasts. I felt them jiggle as I lifted the lid and hoisted the trash bag in. The neighbor might’ve let out a low whistle, but I couldn’t be sure. I was too focused on getting back up the driveway without hurrying, as I knew I’d be in even bigger trouble if I rushed or covered myself.

Finally, back at the doorway, you made room for me to head inside, and smacked my ass in the process, nice and hard. I let out a yelp and heard you chuckle behind me.

Taking me by the arm, you led me back into the open air living and dining room. At the head of the table, you reached around and yanked down the cups of my bra, exposing my tits.

“See, I could’ve made you go outside like this… which, frankly, you probably deserve. I don’t know how many times I need to remind you who these belong to.”

You grabbed my breasts and squeezed, shaking them up and down. Pinching my nipples, your touch made me moan and squirm against you, rubbing my ass against your groin.

“Tell me,” you instructed.

“Y-you… oh, god… they belong to you, boss…”

With a smirk, you stopped pinching and gave each of my tits a solid smack.

“That’s right. Now bend over.”

I did as I was told, placing my forearms on the table. You nudged my feet apart, spreading my legs. I braced myself for you to lift my skirt, but you didn’t. Instead, you walked around to the front of me, taking in the sight of my bare breasts hanging just above the table.

Taking me by the back of the neck, you gently but firmly lowered me down, until my tits were grazing the table, teasing my already tender nipples.

“Stay right there,” you commanded, and I did as I was told. “Now, in addition to flirting with your tits out, there’s also the issue of your bratty behavior. The next time I ask you to help with something, how will you respond?”

“Um, without complaining?”

“That’s right. And if you can’t manage that, I just might have to pull down your panties and spank your bare ass right then and thereno matter how many guests we have. Is that understood?”

My threatened ass wriggled under the imagined humiliation.

“Y-yes, boss. I understand.”  

“Good.” You paced behind me, sighing again. “And then there’s the matter of your terrible manners. Elbows on the table, talking with your mouth full, drinking like a sailor… and worst of all, interrupting and talking over our guests. 

“I-” I started to protest, but you grabbed my hair and pulled my head up to look at you.

“Yes, exactly like that. Can you keep quiet, or do I need to shove your dirty panties in that chatty little mouth of yours?”

I shook my head, clamping my lips together.

“That’s what I thought. Where was I… ah, yes, your offenses. Twice, after dinner, you uncrossed your legs and flashed your panties to the entire room. Lastly, you drunkenly sloshed droplets from your not-quite-empty brandy glass onto the freshly waxed floors.”

My eyes went wide. This was a long list of transgressions, and some of them were quite serious. I couldn’t imagine how harsh my punishment would have to be to atone properly, but clearly taking out the trash with my sweater open was only the beginning. 

“I’ve given it a lot of thought,” you continued, “and tonight helped me make up my mind. I’m sending you to a week-long intensive at Madame X’s Finishing School.”

My mind raced. Wasn’t finishing school something for wasps and debutantes?

“I, um… May I ask, please, boss… What does that mean, exactly?”

Crossing behind me again, you took your time lifting my skirt. Taking hold of either side of my thong, you slowly rolled it down to just below my ass cheeks, leaving my bottom naked and exposed.

“It means you require more training than I have time to administer,” you said.

I let out a small whimper and felt my ass twitch instinctively, anticipating the impending spankings.

“You’ll spend a week under Madame X’s tutelage,” you went on, “and when you return to me, I expect to see vast improvements in your behavior. Is that understood?”

I nodded, sincere in my earnestness. More than anything, especially in that moment, I wanted to learn how to be a good, obedient girl for you.

“Yes, boss,” I promised.

“I certainly hope so,” you replied. “Now in the meantime, after your atrocious conduct this evening, how many spankings do you think you deserve?”

“I, um… twenty?” I guessed.

“That sounds like a fair start,” you agreed. Smack, smack, smack… 

You launched into my punishment without further preamble, instructing me to count my spankings aloud until we reached twenty. I gasped and squirmed under the assault, feeling extra turned on every time my body lurched forward and my sensitive nipples grazed the dining room table.

“...seventeen… ooh… eighteen… nineteen… oww oohhh oww… twenty.” 

I knew better than to think we’d reached the end of my discipline.

“Stand up,” you instructed. “Grab your elbows behind your back.”

I obeyed at once, my ass tingling as you gently took hold of my chin and turned me to face you, inspecting my taut, perky nipples.

“That was for behaving like a vulgar, uncivilized brat. Now we need to teach you what happens when you act like a flirtatious little harlot who flaunts her tits everywhere.”

I lowered my lashes, ashamed of my behavior.

“Yes, boss,” I agreed in a small, quiet voice.

“Mmm, good girl. That’s the kind of humility I like to see.”

Crossing to the buffet, you slid open a drawer and procured two slender, metal clips that looked like tweezers, each one sporting a small, delicate jewel dangling off the end.

“Normally I wouldn’t indulge you with nipple clamps as punishment,” you informed me, “because we both know it’s far too much fun for you to have your nipples tormented. But tonight I think they’re just the thing we need…”

Securing one of the clamps to my already tender right nipple, you smirked as I moaned and bit my lip.

“Your penance is that you have to wear these until it’s time for bed,” you continued, tightening the clamp and making me gasp, “and I will - of course - play with them as much as I want…” your torment was slow, deliberate. Securing the second clamp to my left nipple, you took your time pinching and fastening it into place. “...and you will not, under any circumstances, be allowed to come. Not tonight, not in the morning… not until you return from finishing school and demonstrate what a good, obedient girl you can be.”

“Y-yes… ohh god… yes, b-boss…” I stammered out my words, panting as you gently tugged on both of the clamps, sending jolts of lust and longing through my body. A whole week without an orgasm, and after all this delicious torment… it was going to take a lot of self-control to truly behave myself.

You stepped back, circling me, taking in my disheveled state. Sweater open, bra pulled down to expose my naked tits and now securely clamped nipples… skirt hiked up to my waist, with my panties pulled down just enough to bare my ass, which was surely still red from being good and spanked… 

“I’d like a nightcap,” you declared. “No need to adjust your clothing. You can serve it to me exactly like this, as a reminder of what a naughty, disobedient girl you were tonight. Then I’d like you to sit next to me in the same exposed, vulnerable state, in case I require additional slutty maid service this evening.”

I bit my lip, eyes wide.

“Yes, boss.”

While you settled yourself on the couch, I poured your bourbon. Three rocks, just the way you liked it. After I handed it to you, I sat down as you’d instructed, not making any adjustments to my clothing. 

You’d found a documentary of some kind to watch while sipping your drink, but I hardly noticed the content. I was too distracted by your frequent tugging on my nipple clamps, each one sending jolts of desire through my body. I squirmed and whimpered, which only make you tug more, and harder.

Eventually, after I’d been sent to refresh your drink one last time, you declared that it was time for bed and marched me upstairs. By then I was in such a hard up, lascivious state, I would’ve walked around the block with my tits and ass hanging out for everyone to see, if it meant you would let me come.

But the decision to withhold orgasms from me was never made lightly, so I knew better than to beg or challenge you.

I cleaned up and got ready for bed, but you hadn’t instructed me to change or adjust my clothes, so I left them as they were. Sure enough, when I joined you in the bedroom you informed me that my last punishment of the night would be one more lesson for acting like a naughty little slut.

I stood in front of you as you gently removed the nipple clamps, since spending the night in them wasn’t safe.

“Take off your sweater,” you commanded, and I complied at once. Circling me, you decided to take my skirt off as well, leaving me in nothing but my underthings, with both bra and panties left so askew, they did nothing to actually cover my body.

“Perfect,” you decided. “And remember, no touching yourself. You need to learn some self control, so you’ll think twice the next time you feel like shamelessly brandishing your tits in front of company.”

I gulped and nodded.

“Yes… yes, boss.”

Sliding your hand up under my hair, you gripped and pulled, hard, tilting my face up toward yours. Tracing my open mouth with your fingers, you spoke slowly and calmly.

“I mean it. If I wake up and catch you fondling yourself, you’ll be spanked until you can’t sit for a week. I don’t care how turned on you are… and if I know you…” your hand slipped between my legs, exploring the wetness there all too briefly, “...oh, my… you’re gagging for it, aren’t you?”

You said the last bit with a smirk, and I nodded, my face flushing at the confession.

“Y-yes… I am. I w-want to come… so badly…”   

Now slick with my juices, your fingers probed into my mouth.

“Suck,” you instructed, and I did as I was told, sucking and licking your fingers clean until you were satisfied. “That’s a good girl. I’m glad to see you’ve learned how important it is to clean up your messes.”

Gently tossing me onto the bed, you directed me to get under the covers and climbed in next to me. I thought I might explode from repressing the urge to straddle you, with every inch of me aching for release. But I was determined to learn my lesson and practice self-control, so with a sweet goodnight kiss and murmured words of gratitude, I curled up next to you and went to sleep.