The Best Days of My Life? - Cover

The Best Days of My Life?

by Ashley

Copyright© 2023 by Ashley

Erotica Sex Story: Clare Harlow is fifteen and, through no real fault of her own, is at the last chance saloon of schools. Within days she's in trouble again, and again she is relatively blameless. But Clare is no shrinking violet and she's not going to take it lying down.

Caution: This Erotica Sex Story contains strong sexual content, including ft/ft   Fa/ft   Blackmail   Coercion   Consensual   Reluctant   Lesbian   Fiction   School   Spanking   Anal Sex   Analingus   Masturbation   Oral Sex   Sex Toys   Big Breasts   Teacher/Student   .

I’m sitting outside the headmistress’s office waiting to be called in. I was expelled from my previous school for kissing a girl. It wasn’t that simple obviously: she claimed that I forced myself on her and, even though it wasn’t true and I strenuously denied it, they all took her word for it. I guess it was partly my fault: I hadn’t been the best behaved of students, but even so!

So my parents had sent me here to Saint Saviours, a girls’ preparatory boarding school. My dad had been at prep school and he figured that it would make a man out of me, or some shit like that anyway.

On my first day, I have to see the Headmistress, Miss Collins.

“We won’t tolerate that sort of behaviour here at St Saviours,” she tells me with no other introduction.

“But--” I want to explain that it wasn’t quite as straightforward as she might have been told.

“No buts.” she barks. I hate her instantly.

A few days later I’m walking along a corridor and there are some senior girls in a huddle, laughing like crazy. I sidle up to them and one is doing an impression of Miss Collins. She’s really, really good and she’s making her say all kinds of outrageous and awful things. I piss myself laughing. No - I literally piss myself laughing!

I’m horrified and I walk as quickly as I can to the loos. My knickers are soaked and I chuck them in the bowl and clean myself up. The bell for the first class of the afternoon rings and, after a quick rinse of my hands, I hurry off to it.

It’s Maths and the teacher, Miss Cullingham wants me to go up and work through the solution of a quadratic equation on the blackboard. As I get up I forget all about my lack of underwear and I see Miss Cullingham’s eyebrows go up and I think maybe she’s seen up my skirt.

She says nothing and I get the test right even though I’m bricking it that she saw my bare pussy. As the afternoon wears on I begin to relax when nothing untoward happens. Truth be told I’m actually enjoying having the fresh air on my pussy and I spend the afternoon with a little sex buzz on. Until ten minutes before the end of the last class of the day that is: then a staff member comes in, hands the teacher a note and then leaves.

“Could Miss Clare Harlow stay behind after class?” Miss Cullingham says before letting us go. Oh Fuck, I really hope this isn’t what I think it is.

“You’re to see Miss Collins immediately,” she tells me when I go up to her desk.


“It has been brought to my attention that you are improperly dressed,” is Miss Collins’ opening remark. I look down at my shoes and give a little prayer that she means my tie isn’t done up correctly.

“Stand in the corner with your hands on your head,” she instructs.

I do as she says and then I feel my skirt being lifted and she makes a tutting noise and then lets it down.

“Sit down there please Clare,” she says, pointing to one of the two chairs in front of her desk.

“You’ve disappointed me Clare and I’m afraid you will have to be punished,” she says, looking at me with apparent sorrow.

“Normally corporal punishment is against our rules,” she begins. I relax just fractionally before the word ‘normally’ sinks in. “except on the explicit instruction of a parent that is.” Once again I begin to relax when she leans forward and pushes a button on her phone.

“Miss Smithers, could you send Mrs Harlow in please,” she says into it, and a pit seems to open up under me. They’ve called my mom and made her drive all the way over here! Surely she’ll never agree to them beating me though?

“I’m afraid it’s all true.” Miss Collins says to Mom when she’s sat down. Mom looks at me with an expression of dismay and exasperation.

“Clare, what are we going to do with you?”

“But Mom--”

“I’m afraid we have only two choices at this stage,” Miss Collins says to my mother. “expulsion or...”

“Or?” Mom asks.

“ ... or the cane.”

Mom looks at me.

“There are no more schools,” she explains. “they only just accepted you here. I’m sorry Clare.”

“We used to have a chair for this express purpose but ... well, never mind, we’ll have to make do. Clare, please kneel on the end of this bench seat with your other foot on the floor.”

When I do my bare pussy is touching the arm of the seat and I have to go up on the tips of my toes to stop it. I feel my skirt being flipped up over my back and my ass and pussy are exposed to them both.

I feel three hard blows across the cheeks of my arse that hurt like hell. I clench both my fists and my jaw to stop myself from crying out.

“She used to be such a good girl,” I hear Mom say to the head.

“Sometimes they get to a certain age and they lose their way,” she replies. They’re chatting away as if I wasn’t right there with my burning arse on display and I wish they’d just get it over with. My foot is starting to cramp and the pain in my bum has turned into a maddening tingling that is actually turning me on. A lot.

There are three more blows with no warning, then another pause. My leg begins to spasm and my pussy lips touch the arm sending a jolt of arousal through me and I feel myself starting to get wet. I clench, trying desperately to keep it all inside but that just pumps up my clit even more.

I force myself up onto my toes again just as she hits me three more times with the cane. My leg gives way completely and my pussy, and especially my clit, are forced hard against the arm of the chair. The spasms in my leg mean that I’m basically grinding on the arm, and then she strikes me three more times and I cum. The wetness that I’ve been trying to keep inside gushes out all over the leather arm and I slump down with my body shuddering and twitching.

There is utter silence except for the panting of my breathing.

“It’s worse than I thought.” Miss Collins says quietly.

“You have my permission to do whatever it takes Miss Collins.” I hear Mom say dimly through the haze of my cum mixed with overwhelming and crushing shame. Eventually, I manage to stand up and they’re both glaring at me reproachfully.

Miss Collins hands me a box of tissues and I go to lift my skirt.

“The seat Miss Harlow! The seat!” she bellows and I meekly clean up the mess I made, then I stand before her desk while Mom sits in one of the chairs. Miss Collins has her chin in her hand and tuts occasionally and then seems to reach some kind of decision.

“Miss Smithers, do you think you could find Susan Rangely for me and send her in,” she says into the phone. We wait for what seems like ages in awkward silence. Finally, there’s a timid knock on the door.

“Come in.” Miss Collins barks and a nerdy looking senior comes in.

“Miss Rangely here is going to attempt to guide you back on the path to propriety,” she announces and I look at Susan with surprise. She looks back, equally shocked. “You will share her room and she will teach you how to be a lady. You will do whatever she tells you at all times, is that clear?”

I mumble “fucking hell.” into my chest.

“I beg your pardon, Clare?” Miss Collins asks archly.

“Yes, Miss Collins,” I say meekly. As I look up at Susan again my anger starts to crystalize: it seems that if fate is insisting on casting me in the role of slut then maybe I should embrace it! Especially since all the adults in my life seem only too happy to believe that it’s true.

Looking at it in that light I admit to myself that exposing myself to my mom and Miss Collins actually turned me on like fuck. And the caning aroused me beyond belief, after the initial pain had faded anyway.

I look at Susan again and see a pretty girl underneath the prim clothes, severe hairstyle and cheap glasses. A wicked thought enters my head which I have trouble not smiling over: I want to see this girl cum!

Susan and I are dismissed leaving Mom and Miss Collins to discuss what a slapper I am. Probably anyway.


The room we are to share is small for two and a little musty and cold, but in some ways, it’s better than sharing with three other girls which is the situation I’d been in before.

When ‘Miss Susan’ tells me to light a fire I realise that Miss Collins has basically made me her ‘fag’. Not in the sense of a homosexual or a cigarette, but in the sense of the way juniors were treated as servants to the seniors back in the bad old days at public schools.

I take it as an opportunity to test her own propriety. When her back is turned I roll up my skirt. I’ve still got no knickers on as she’ll be able to see when I kneel down and start cleaning out the grate: either she’ll chastise me or not. The answer turns out to be ... not!

When I stand up to get some coal she tries to look as if she’s reading a book but I can tell by the rapid rise and fall of her chest that she’s excited. Miss Collins has picked the wrong girl to be my personal saviour!

Although there are two beds there is only one desk. When I try to sit at it to do my homework Susan bats me away in the direction of a chair.

I sit down and go through my assignments but I can see Susan glancing at the top of my thighs obviously hoping to see more of my charms. I go full-on Sharon Stone and cross and re-cross my legs, constantly flashing my pussy at her. I adore the way her eyes bore into me and my clit is throbbing madly, desperate for some attention.

Finally, it’s time for bed and I’m disappointed when she manages to get changed into her voluminous nightdress without me seeing much of her body, and again when she appears to avert her eyes when I get changed, much less demurely.

After I get into bed and Susan turns out the lights I can, at last, give my clit a bit of the loving it’s been crying out for. I have my first real chance to go over the events of the day and, as I relive them in my head, I get more and more excited. When I open my eyes I see that there’s moonlight coming through the curtains and Susan is watching my bedclothes bobbing up and down at my groin.

Even with her watching me I’m just too tired to try to cum. I roll over, facing her, and pop a cunty finger into my mouth. I grin at her shocked expression and fall asleep.


The next night I continue to tease her: flashing my knickers this time while building the fire and doing my homework. She’s obviously very, very interested but she doesn’t seem to want to move things along.

I’m not sure where the idea comes from but it’s a corker: “Would you like me to warm your bed, Susan?” I ask. She looks a bit puzzled but nods anyway.

As I start taking my clothes off her eyebrows rise up like magic. I strip to my bra and knickers and her eyes are all over me. I slip into her bed, it’s freezing and I wriggle around trying to get warm.

As I lie there she gets changed, demurely again, into her nightdress then looks down at me. I get out and she gets in.

“That actually works beautifully,” she says all snuggly and warm. “you’ve got yourself a new job, young lady.”

I stand by the head of her bed with my pussy as close to her face as I can get it. I pluck at the edges of my knickers, as if I’m nervous, but in fact allowing her tiny glimpses of what’s underneath.

“Will there be anything else Miss?” I ask timidly. She’s licking her lips and can’t take her eyes off my groin but finally, she shakes her head.

I get into bed and lie on my front, trapping a hand under me. Through slitted eyes, I can see that she’s watching me. I like that a lot and make no attempt to hide my little arse bobbing up and down.

I love having her watch me and my other hand seeks out a little hard nipple to tease. I surreptitiously check and she’s still watching me, her eyes wide and her lips parted and nibbling at each other. I allow a small moan to escape my lips as I cum, and her face is a picture: half horrified but half naked yearning! Then I see it: the subtle movement of Her bedclothes at the top of her legs!


All of the next morning I’m horny as hell and I’m squirming in my seat in all my lessons.

At lunchtime, I forego food and go to our room. I get myself off grinding on my pillow while imagining Susan eating me out. When I’m finished the pillow is wet and my scent is all over it. Grinning like a loon I swap it with Susan’s. Tonight is going to be the night, I know it!.

Humming happily to myself I take a few test shots with my phone, setting it to silent and no flash. They look fine and I hide the phone on the shelf above Susan’s bed.


I take my panties off after classes before returning to our room, and I’m almost dripping as I lay the fire.

I dither when it comes time to warm her bed.

“What’s the matter with you?” she asks testily. I look down at my feet and mumble my response.

“I’ve got no knickers on Miss,” I confess.

“So?”

I feign shyness as I strip naked and get into her bed, but I love the way she’s looking at me. I lay in bed, looking up at her with big, scared eyes. She begins to undress and our eyes meet. This time she strips to her bra and knickers right in front of me. She looks at her nighty and then reaches behind her back and undoes the bra.

 
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