Naughty Chair Letter

I know all about the special chair you keep in your study. I sneaked a peek when you were away. My only regret is I did not get to witness you using it.

I saw how your new chair takes pride of place in the middle of your room. It’s quite a statement piece. Effortlessly stylish. Honey-coloured wood with sturdy legs supporting a flat varnished seat, and a tall back of three distinctive slats.

Of course it was the seat that truly seized my attention, and the ebony phallus that protruded from the centre. I noticed it glistening, a fresh condom already rolled down its shaft and slathered with gel. It radiated an ominous energy, as if awaiting its next sitter. But who?

Is this your own secret Naughty Chair, Miss?

When thinking about smacking bottoms makes you all wet, do you long to slip off your panties, and hitch up your dress, and let yourself sink upon the protrusion until you’re filled with delight? Do you rock and ride upon it, imagining there’s a bare bum across your lap, a paddle in your hand, and the sound of whacking in the air?

As I stared, I quickly realised that if you arranged your hem so it draped over the edge of the seat, no one would ever suspect the naughty secret you had hidden beneath. You could even wait like this for those reporting to your office to be spanked.

“Enter!” you’d shout, when you heard the nervous rap on your door. You’d beckon them over to where you were seated, your paddle already gripped menacingly. You’d remind them that spankings are always on a bare bottom, and watch on with considerable satisfaction as their trembling fingers fiddled with their buttons, before they obediently pulled their own panties down.

“Bend over!” you’d command. That moment must feel so good, when they lay over your lap, and the sudden addition of their weight pushes you further onto your impalement. But which hole is it? Do you prefer the thick intrusion to fill your wet clenching cunt, or to stretch your tight bottom? Which sensations feel better when you’re spanking hard enough to make them squirm?

Do you spank those across your knee until you’re on the very brink of coming? I expect you’d brusquely tell them to stand, to pull up their panties and remind them to close the door firmly as they leave. When you’re alone at last, is that when you ride to a climax, or do you stay on the edge until the next visitor arrives, so the sound of your pleasure is masked by the noise of their whacking?

I quite understand why every strict distinguished lady should own a Naughty Chair. It’s much more elegant to climax without touching. Coming on one’s sticky fingers is so unbecoming.

But now, after some thorough imagining, I’ve realised the Naughty Chair might be intended to solve a much harder problem…

Are you of the school of thought that naughty boys can’t be properly punished with an erection throbbing between their legs? Do you believe those with stiff cocks will be too busy thinking about running off to wank just as soon as they were dismissed? You know naughty boys love to masturbate as they rub their stinging bottoms. So those sent away still hard might find their punishment quite enjoyable - and that wouldn’t be right at all.

Maybe that’s why you’ve obtained a Naughty Chair: to deal with those who report to be disciplined with erections in their pants. It would be most unseemly to permit such naughty boys to masturbate their hardness with their hands, with all that tugging and squelching and grunting. That’s why stiff visitors are made to sit on the phallus, until their bums are filled and well-stretched, and their excitement finally overwhelms them.

Do you make them undress for the chair? I’ve seen the labelled hooks on the wall. Blazer. Tie. Shirt. Vest. Socks. Trousers. Underpants.

It must be exciting when your visitor is standing naked in front of you, his arms folded respectfully behind his back. He tried not to get hard, but failed, and now his stiff penis is jutting rudely towards you, like a rogue uncontrollable finger. You tap it with the tip of your cane, evaluating its stiffness, emphasising who’s in charge.

I noticed the pile of shiny silver packets on the nearby table. I think you’d enjoy watching a boy prepare his own sitting, fetching a fresh condom to roll down the dildo, then telling him to open a second to roll down his own shaft. It’s much less messy this way. There could be quite a queue of naughty boys to deal with on any one day, much too many to clean up after each sitting.

I’m sure you have a meticulously planned procedure. He’ll be told to squat over the seat, orienting himself until he feels the tip of the protrusion tickle his bottom hole. Then he’ll let himself sink lower until he feels the dildo stretch his bottom.

I guess that the wide gaps between the slats are there to allow his wrists to pass through, and be bound behind. Better to keep his hands out of the way when he’s desperate to grasp his throbbing cock. He’ll feel so naughty when helpless upon your Naughty Chair.

When he’s at your mercy, I expect you’ll turn the sand timer you keep on your desk. He’ll be given five minutes to ejaculate, and if he hasn’t come by then, the number of whacks he’s due to receive will be doubled.

I suspect most will come quickly on your devious chair, squirming as the specially shaped protrusion finds just the right part of their prostate. Often the humiliation of having to fuck themselves in the bottom is enough. Riding the thick phallus in an urgent frenzy, quickening as the sands run out, repeatedly rising on their thighs and impaling themselves.

Regular visitors who know that canings sting much more after spurting might hold back. So naughty boys who still haven’t come when their time runs out may need a helping hand. Do you pinch their erection between two fingers, and make them ride until they gush? Or untie their wrists and make them wank?

Once he’s filled his sheath, it would be sensible not to waste any time before delivering his caning. He’ll be expected to rise and bend over with his palms flat upon the seat, looking down on the glistening shaft where he’d just been sitting. He’d feel your cool cane tap against his cheeks, his hole still sore and twitching from the chair’s intrusion. His wilting penis will dangle heavily between his legs, still wrapped in its white-tipped cocoon. Embarrassment flushes his face burning pink, just like his bum is about to be too.

Is this how you employ your chair, Miss? To confiscate the erections of naughty boys before they get their bottoms whacked.

From what I’ve overheard from governesses, there seems to be some debate over the most effective order of orgasm and caning. A boy could also be caned with his erection jutting proudly, and then be made to sit on his hot sore stripes until he spurts, so he won’t immediately run off to wank. I hear kinder disciplinarians consider climaxing after a spanking a tender mercy.

Regardless of what order discipline is applied, when it’s time for him to get dressed you’ll make him pull up his undies over both his stinging bum and the squelchy condom. You’ll make it quite clear that his sheath must stay wrapped around his sticky penis until you personally pull his undies down to remove it. He might well be wearing it for hours, until he’s absolutely desperate to pee.

Afterwards, you might send some naughty boys to the detention room, where they can sit on another hard wooden seat on their sore caned bums, all too aware of the clammy wetness of their own cum trapped between their legs. You might take others out in public, their sticky white secret still a damp memento in the front of their briefs, with thin pink lines glowing unseen beneath their trousers.

So, is the naughty chair intended for you, Miss?

Or naughty boys with big stiff cocks?

I think I’m definitely in one of those categories.

Yours sitting comfortably,

An impeccably well-behaved boy

These letters can be printed and used as scripts or props in your own fantasies or roleplaying. 2nd Person Erotica is rare, so if this format lights your fire, you might enjoy these other letters:

Once you’ve printed a physical copy of this letter, here’s a few ideas on how to use it:

• As a sex toy, read along to this as you play

• As a template to modify, e.g. write it from a naughty girl’s perspective

• As a roleplaying prop, imagine sending this letter to your partner

I hope you’ll use this letter as inspiration, and create your very own Naughty Chair!

And I wish you all a very kinky Lupercalia!