Wheldrake Goes To Prison

Do you have a favourite sexual or kinky fantasy, one that you find surpassingly, perhaps inexplicably erotic and revisit compulsively in the privacy of your own thoughts? Mine, though it’s a microgenre with myriad possibilities rather than a single unvarying scenario, is the fantasy of submitting to voluntary incarceration in a harsh, forbidding prison or prison-like facility. What could possibly be hotter than intimidating guards, cold steel around one’s wrists and ankles, and the crushing sense of being under the absolute control of a whole institution devoted to keeping people in a state of abject captivity?

For more than a year before My Lady became My Lady, she was a valued correspondent. We exchanged news and ideas, read each other’s fiction and offered suggestions, discussed BDSM and BDSM fantasies, and eventually figured out that we both wanted her to have considerable power over me. While we were still e-mailing back and forth as equals, I told her about my thing for prisons, a fascination that she didn’t share. However, she found my incarceration fantasies interesting enough that we kept occasionally bringing them up in our correspondence, and eventually I started writing a story for her that was set in what I whimsically called the D. Keith Prison for Men. In the story she’s a kind of consultant to the prison, a role that she chose herself, and I’m a prisoner serving a voluntary but strictly enforced 30-day sentence. Once I’ve signed the contract, which I do about 2000 words in, I’m stuck for the full 30 days no matter how loudly I might scream “Safeword! Safeword!”

The story has grown to considerable proportions, but is nowhere near finished. I still send My Lady installments as I complete them, and she sometimes makes decisions about how something in the prison should work or how a character should behave. These days, of course, the parameters she establishes for the story have the status of orders from My Lady, not just preferences expressed by a friend for whom I happen to be writing something. Because of those parameters, and the fact that I’m writing to please her, the prison in the story differs in some ways (though only one fundamental way that comes to mind at the moment) from the ones in my own private fantasies.

The story will never be published, at least not without massive editing. There’s too much personal stuff about me and My Lady in there (although much more about me than about her, partly because in many ways I actually don’t know her very well) and the story is too sprawling and self-indulgent. However, I thought it might be fun to post a lightly (and transparently) edited excerpt here. As it begins, a nude and restrained Prisoner Wheldrake is in the middle of his first night in custody, and is being marched across the prison yard by two young male guards, Officers Bledso and Kimura. I write in the first person present and address My Lady in the second person (that is, when I say “you” in the story, I’m referring to her).

I may post additional excerpts in the future, or go into more detail about my incarceration fantasies in general, if people seem interested and My Lady gives permission.


As I march obediently between my captors, turning occasionally but always walking on a concrete surface, I begin to feel symptoms of rising panic.  My breathing  is growing quick and shallow within the stifling hood, and a painful knot of fear is swelling in my belly.  I stubbornly fight it down, trying not to think about what might be in store for me over the next thirty days at the hands of you and the men.  I try to focus instead on the more limited peril of my coming encounter with the “boss man”, which I suppose probably means the warden of the prison.  I can at least hope that he’s just going to take a brief look at me and send me to a cell, like he did with the Andrews brothers.

It’s hard for me to even imagine what the warden might be like.  In American movies and TV shows wardens usually seem to be tough-minded administrators in civilian clothes, but I have no idea whether that generalisation applies in here or not.  I don’t know whether to picture someone old or young, black or white, firm and fatherly or gleefully sadistic.  Given that he presides over this prison, it’s a fair bet that he won’t exactly be warm and cuddly.  There’s the possibility, too, that he might have plans for me that go well beyond sending me off to a cell for the night.  Worrying about his power over me, however, is almost a welcome distraction from worrying about yours.

“Three steps up,” Kimura says abruptly.  The guards allow me to climb them more or less at my own pace, and then bring me to a halt on what feels like a stone porch or patio.  I hear a click and an electronic beep, and then a crackling, distorted male voice asks “Prisoner [Wheldrake] to see Master, sirs?”  I blink in surprise inside the hood.  I thought we were prisoners here, not slaves.

Kimura, however, doesn’t miss a beat.  “Correct,” he replies crisply.

“Bring him right in,” invites the voice from the intercom.  “Please don’t forget to have him wipe his feet, sirs.”

I wonder if the “sirs” indicates that the man on the other end of the intercom is a trustee, or maybe a trainee guard of some kind… [T]here’s a conspicuous click that might be the sound of a door being automatically unlocked, and then I’m being ushered into an air-conditioned space that would probably be perfectly comfortable if I had clothes on.  As it is, the temperature is slightly on the chilly side, although nowhere near as bad as it was in the strip-search room or in my cell downstairs.  There’s a rough carpet underfoot.

“You heard him, prisoner,” Bledso tells me.  “Wipe.”  I obey, rattling the chain between my ankles in the process.  It’s otherwise very quiet in here, amplifying the sound into a dreadful clatter by comparison.

“Right through here, sirs,” someone says.  Even accounting for the distortion, I don’t think the voice is the same one that came through the intercom.  How many trustees, or whatever they are, does the warden have working for him in this building?  I have the impression that the one who spoke just now is a young man, and there was a controlled pitch to his assured but deferential voice that made me think of actors and PR people.  Weird.  I’m not thrilled about being naked in front of the guy, whoever he is, but at least he isn’t slapping my ass and saying he wants a piece of me.  Thank the gods for small favours, right?

Kimura and Bledso march me a short distance over hardwood, holding my arms as firmly as ever but setting a slower pace now that we’re indoors, and then I hear the crisp rap of knuckles on a good solid door.

“Prisoner [Wheldrake], Master,” Mr Assured but Deferential announces.

“Bring him in,” a man on the other side of the door responds evenly, in a European-sounding accent that I can’t place immediately.  Some quality in his speech makes my ears prick up, to the extent that human ears can, and the hairs stiffen on the back of my neck.  His voice isn’t particularly deep or menacing or anything like that, but there’s an unmistakable note of confidence and authority that resonates deep in my belly.  As strange as it feels to admit this about another man, he sounds captivating.

I’m being manhandled through the door, into his presence.  I walk over more hardwood, then step onto what feels like a thin carpet and find myself brought to a halt by the strong hands on my arms.  Okay, here I am.  I stand patiently in the private darkness of the hood and wait for something to happen, resisting the urge to shuffle my feet or otherwise express the nervousness that is twisting my belly into knots of apprehension.  I hate not being able to see, and not knowing what kind of place this is or exactly who is here with me.  I hear the door fall gently shut, and feel more trapped than ever.

“Take off his cuffs and shackles,” the accented voice says after a moment.  “He can’t get away.”  Anonymous hands, presumably Bledso’s and Kimura’s, set to work at my wrists and ankles.  A moment later I’m unrestrained, though the hood is still in place.  I could easily reach up and remove it, but I’m nowhere near that brave or foolish.  I let my hands fall to my sides, and keep them there.

I hear a creak that could be someone getting up from a chair, and then soft footsteps on the carpeted floor.  It sounds like someone is walking towards me, and the room is so quiet that I can even pick up the tidal whisper of his breathing.  I’m almost positive it is a man, and I get the impression that he’s fairly tall and standing within easy reach.  I swallow hard, and bite my lip to keep from trembling.  I can only assume it’s the warden, the man who apparently likes people to call him “Master”, but I don’t actually know.

A hand closes around my left bicep, kneading and squeezing in a way that seems distinctly exploratory.  Whoever this guy is, he has strong fingers and isn’t shy about using them.  His grip isn’t exactly rough, but it’s powerful enough to be mildly painful.  He moves up to my shoulder, then grabs a handful of my left breast and twists the flesh hard enough to make me gasp.  He prods roughly at my belly, and I brace myself for him to grab my balls next, but instead he snatches away my hood.  Suddenly, we’re standing face-to-face instead of face-to-cloth.

The lighting in here is gentle enough that there’s no momentary dazzling.  I can see perfectly well once the hood is off, and I’m looking practically into the eyes of a man who would register as intimidating even if I passed him in the fucking supermarket.  Under the present circumstances, he’s not far short of terrifying.

Though he doesn’t have the monstrous build of Pitansky or Driscoll, he’s got to be well over six feet tall, and he has a lean, chiselled muscularity about him.  I don’t doubt that he could take me down and pin me to the floor with one hand tied behind him, even if I dared to fight back.  He looks spare and hard in a way that I associate with soldiers, rather than prison guards, and the angularity of his face matches the look of his body perfectly.  If his features were any less fleshy, he’d be flirting with gauntness.  He has a full head of sandy hair, cut very short and liberally sprinkled with a grey that almost matches the flinty colour of his eyes.  His beard and moustache are just as severely trimmed, and are greying even faster.  He’s dressed in khaki-coloured clothes that aren’t quite a uniform, but resemble something a rugged British gentleman might wear on safari.  Quite apart from his size and strength, he exudes confidence and authority as naturally as a shark exudes menace or a giant panda exudes lazy contentedness.  My first impulse on seeing him, as ridiculous as it sounds, is to literally throw myself at his feet.  No doubt the fact that I’m stark naked and completely in his power is a contributing factor, but still.

He takes my chin between his right thumb and forefinger, inevitably hurting me a little, and turns my head from side to side.  He makes a small sound in his throat as he finishes this inspection, a little exhalation that might express either satisfaction or disapproval, and then releases me and turns away.

Only now, when I’m no longer held by his gaze, do I take in my surroundings and realise that I’m not alone with this imposing figure in khaki.  I assume that Bledso and Kimura are somewhere behind me, interposed between me and the door, but what truly arrests my attention is the sight of you sitting calmly on a leather sofa in one corner of the room.  You meet my gaze without any discernible change in your expression, though your eyes flick up and down my naked body in that casual way I’ve already grown used to.  The warden-Master-guy has settled into a chair facing me, on the opposite side of a wooden desk whose surface is sufficiently well-polished to literally gleam in the soft light of the halogen lamps that illuminate this room.  Apart from the desk, which is bare apart from a laptop computer and a stack of manila folders, the place looks more like a living room in a nice condo than a warden’s office in a particularly harsh prison.  There’s a second sofa perpendicular to the one you’re sitting on, and the walls are of white plaster rather than bare institutional concrete.  There are even a couple of paintings, one of Roman centurions leading a bound, naked prisoner and the other of an equally nude man kneeling and pressing his head to the ground in front of a booted figure who is cut off around the knees by the upper edge of the painting.  My nervousness is beginning to congeal into panic.  If nothing else, being naked in a civilised setting like this feels more incongruous, and therefore more uncomfortable and humiliating, than being naked in the austere, institutional concrete rooms and corridors of the building I left a few minutes ago.

The warden, as I’ve decided to think of him, fixes me deliberately with that intense stare of his.  “Welcome to prison,” he tells me, which must be at least the third or fourth time I’ve heard that sentiment expressed today.  “I’m very glad to have you here.  [Your Lady] told me about you some time ago, and I’ve been waiting ever since.”

He’s been waiting?  To do what to me, exactly?  I’m certainly not going to ask, however, and a simple response seems safest.  “Thank you… Master?”

“No, prisoner.  You must continue to address me as ‘sir’, at least for the moment.”

I’m not sure how to take his final words, but everything else is perfectly clear.  “Yes, sir.”

“And while we’re on the subject,” you put in suddenly, “you should be aware that prisoners are expected to address me as ‘ma’am’.”

“Yes, ma’am,” I reply quickly, wondering what made you choose that particular phrasing instead of simply saying “call me ‘ma’am’ from now on”.  Were you going out of your way to imply that you don’t see me as anything more than just another prisoner, a member of a class of people subject to certain rules?

The warden eyes me speculatively.  “How are you feeling?” he asks.

I blink in surprise at the question.  “I’m feeling scared, sir,” I reply honestly.  “And powerless, and a bit confused.  I don’t know why I’m here, I mean standing naked in your office, and I don’t know what you’re going to do to me.  I’m also tired and hungry, I guess.  But it would be dishonest of me to pretend that I’m not excited, too.  I’ve been fantasising about prisons and dungeons of different kinds ever since I can remember.  It’s thrilling, in ways I can hardly describe, to be incarcerated in a place like this.”  I pause, and then add, “In a way, it seems almost too good to be true.”