he's the secretary
Chapter 4: How can a sissy secretary be less professional?
In the previous chapters on secretarial clothing and tasks, we didn't stray that far from what one might find in a real office, even if it's unlikely that a man would be employed to type lines while wearing female attire! From far enough away, however, he might still be mistaken for a more conventional secretary, it needing a slightly closer look to confirm that his clothing was a caricature of a smart outfit or that his screen was full of shameful words. Indeed, as we've previously discussed, even a shirt and tie and purposeful tasks can affect a man's state of mind, such that he really could imagine himself doing similar in the workplace.
Because a sissy secretary works in a fantasy world, however, he is not limited by the restrictions that propriety would demand in a professional environment, unless you decide that he should be! You can, of course, pretend that your secretary is employed for real, and thus expect him to follow the same rules that he might in an actual office, requiring respectable clothes and a responsible work ethic. That needn't make playing the part of a secretary any less rewarding or relaxing, however - indeed, having to consider whether garments are appropriately professional can help teach a crossdresser to regard women's clothing more realistically while still allowing him to enjoy wearing something different, whereas the sense of having achieved something productive with his time can be far more satisfying than the fleeting pleasures of aimlessly fooling around.
For some men, the fantasy of becoming a secretary doesn't stop at symbolic attire and assignments, but extends to include equally stylised acts of submission of either a carnal or a corporal nature, if not both. It should not be surprising that those aroused by wearing women's clothing might want to engage in sexual activities while doing so, nor that such activities might see them behaving in a less masculine way than traditional lovemaking. Moreover, men who feel guilty or ashamed about their desires often wish to assuage these uncomfortable emotions by being physically punished, which can be thrilling as well as cathartic. While a real assistant's job description is unlikely to feature being bent over the boss's desk, being put in such an unprofessional position may come very high up the list of priorities for a sissy secretary - indeed, it may be his principal aim, with everything else merely a means of setting the scene.
In this chapter, we'll be considering unprofessional activities that are nevertheless in keeping with the secretarial stereotype, often drawing on themes that might seem more appropriate in a pornographic parody than an actual workplace. Don't dismiss these as being solely about fulfilling a man's fantasies, however, nor assume that you need to be a sadistic dominatrix in order to make use of them. A sexually submissive man can provide satisfaction regardless of whether he's permitted that himself, whereas a playful punishment can be fun for both parties, notwithstanding the possibility of using more serious penalties as a deterrent. Understanding how pleasure, pain and the promise of such affect your husband will allow you to steer his desires in a more agreeable direction, whether that's getting him in the mood, motivating him to do what you want, stressing his submission or discouraging misbehaviour.
How might a man's sexual urges affect his behaviour?
Many submissive crossdressers are sexually aroused by aspects of becoming a secretary, whether as a result of wearing suggestive or sensual clothing, being expected to perform tasks that are thrillingly humbling or humiliating, or ceding control to someone else. As we discussed previously, this isn't the only reason why a man might want to adopt such a role, with many seeking the relaxation or distraction that comes from taking on a different character, quite apart from those who find themselves doing so in order to make amends. Nevertheless, it would be foolish to disregard how your husband's desires may affect him, even if you want to keep what he does as a secretary entirely sexless.
Do real secretaries have sex at work? Not as a matter of course, and not without consequences if they're caught! You can expect similar professionalism from your husband if the idea of getting intimate with his alter ego doesn't appeal, insisting that he doesn't drop his skirt until he's ready to return it to the wardrobe. While a suitably tight garment won't completely suppress any unwanted stirrings between his legs, it will discourage him from doing anything about them, all the more so if combined with cumbersome, restrictive underwear. If that isn't sufficient, you might consider having your husband wear a male chastity device in advance of him donning anything more, requiring it to remain locked around his manhood while there's any danger of him doing anything he shouldn't. You don't have to worry about fitting or removing such a device if you don't want to, instead setting these tasks as your secretary's first and final duties - perhaps hours before or after everything else. When worn for a short period of time, especially by a man wanting to be emasculated, a chastity device doesn't need to be absolutely secure, so long as it provides a high enough hurdle to misbehaviour. Nor need it be comfortable - indeed, discomfort may be considered an advantage, silently scolding the wearer for any arousal! If you're curious about the concept, the book taming the caged beast discusses the practicalities of male chastity in more detail.
Sexual arousal can encourage a man to go along with suggestions that he might otherwise be more reluctant about, should he believe that obliging might lead to him being satisfied. You can take advantage of this by promising your secretary pleasure that's continent on results, only to find fault with his efforts, real or concocted, in order to deny him the expected reward. Submissive crossdressers often find being thwarted as thrilling as being allowed to do what they want, at least temporarily, it fulfilling a deeper desire for them to feel helpless or humiliated, such that this approach isn't as coldly calculating as it might seem. Even if your husband knows that you have no intention of treating him, he may still play along with such a pretence, allowing you to provoke him with mere possibilities. We'll discuss ways you might do this shortly.
On the other hand, sexual arousal can also see sissy secretaries begging to be given excessively difficult tasks or demeaning punishments, only to lose their enthusiasm for such fantasies should they experience them for real. Affected by stylised images and the feelings that they stir, such men may not appreciate how disturbing their requests might seem to a dispassionate observer. Rather than taking everything that your husband suggests at face value, therefore, it is better to consider where it might be coming from in terms of the motivations we have previously discussed, seeing whether there are aspects that could address both your needs without taking things too far. For example, a man expressing a desire to be brutally beaten by a female boss might actually find greater satisfaction in a more symbolic spanking, a few swats with a rolled-up magazine allowing him to relinquish his authority and atone for his shortcomings without needing to incur any bruises in the process. This isn't merely indulging him, however - even a token punishment will encourage your husband to adopt a submissive state of mind, with all the benefits that brings for you as well.
Again, it's possible to make use of this. You might give your secretary what he believes he wants by setting him an impossibly gruelling task, perhaps going so far as to promise a particularly unpleasant, yet provocative punishment should he fail to complete it. After allowing enough time for the initial thrill of such a predicament to wear off and for your husband to start worrying that you've taken him more seriously than he meant, you can offer a way out, reducing either task or punishment to something more manageable, if not forgiving him entirely, provided that he does something else to make up for it. That can be something you wanted him to do all along, even if you present it as being a spur-of-the-moment decision, yet will strengthen your position regardless.
Conversely, even the most enthusiastic of men tend to lose interest after climax, sometimes to the extent of becoming suddenly repulsed by clothes and activities that were previously extremely exciting. That makes it better to keep your husband sexually denied until near the end of a secretarial session, unless you want him to have to work through less pleasurable feelings of shame and guilt. If you're sure that he won't simply take off his clothes, perhaps by taking steps to stop him doing so, you can use this phenomenon to make a punishment more disagreeable, it only needing a few moments to radically change his state of mind. You can instruct your husband to sort himself out while you scold him for taking too long, or alternatively, use your own hand to attend to matters, pulling it away or delivering a sharp pinch at the critical moment to prevent him from enjoying any pleasure. A used coffee cup is a perfectly adequate receptacle to catch the resulting output, which you might insist that he empties into his mouth - an act that many men find genuinely humiliating, even if they've previously begged for it. The resulting shame can linger for longer than the taste should you require him to undertake a tedious, mindless task that emphasises his disgrace afterwards.
How can I get my secretary hot and bothered?
As we've seen, submissive men sometimes find the idea of playing the part of a secretary to be more appealing than the actual practice, but it doesn't take much to renew their interest. An occasional reminder of your husband's adopted role and its implications can be enough, drawing his attention to what he is doing or wearing, how that makes him appear, and what that means. You might do so casually, perhaps treating him to a brief caress or throwaway comment, or make a more formal matter of it, scheduling times for him to stop his work and come to you to be teased. It's even possible to provoke a man without being there, perhaps even without giving him a further thought, taking advantage of technology to stop him forgetting that he's a sissy secretary.
If your husband's outfit contains unfamiliar or uncomfortable elements of the sort we considered previously, he'll most likely be aware of them even if you do nothing to emphasise their presence. Rather than let him get too used to a bra and blouse, however, you might stand behind him and fondle his shoulders while he's sitting down, following any straps you might find with your fingers. Pressing the sliders or rings of a bra into a man's back is a subtle, yet unmistakable way of reminding him that he's wearing the most womanly of garments, but merely sliding your hands over a satin blouse may be enough to leave your secretary feeling weak. The same can be done with nylon stockings if he's standing up, with any garters offering further targets for your fingers beneath a skirt. Ironically, stressing a submissive crossdresser's emasculation is likely to provoke his manhood, even if you leave the latter to languish in his panties, but you might go further and grope his crotch. A sissy secretary's chest can also be felt up, regardless of whether it has any curve, as can his buttocks. If you'd rather not use a hand, consider a foot, with or without a shoe, having your secretary position himself to make that more convenient for you. Either way, you can draw attention to a bulge or seek to lift up a skirt.
Sissy secretaries can be treated to comments that would never be acceptable in a real office. Even if you know exactly what underwear he's wearing, you can still challenge your husband about it, demanding that he confirm its presence, if not its colour, style and size. Can he recite the necessary details, as shameful as it is for a man to know about cup letters and deniers, or should those be the subject of an impromptu typing assignment? Suggestive remarks about both his body and clothing can also be used to get a submissive man hot and bothered, whether you pour scorn on how he needs to pad his bra, or else mock him for his embarrassing bulges. You might do so merely in passing, perhaps referring to your “top-heavy secretary”, even if only ironically, or propose his provocative attire as an explanation for his inability to meet your impossible standards.
Is he employed only to sit around and look pretty, incapable of doing anything more difficult than fluttering his eyelashes, fixing his make-up and filing his nails? In a professional environment, such demeaning comments would be grounds for a complaint, but a sissy secretary can be accosted with these stereotypes and more - you might even give him an unashamedly sexist nickname, or tell him that he needn't worry his pretty little head about even the simplest of matters, because you're not paying him to think. Anything that would humiliate a woman is fair game, but you can also point out how disgraceful it is for a man to be reduced to working as a secretary - all the more so for him wanting to do so!
Many submissive crossdressers regard their desires as something that must be kept secret at all costs, yet simultaneously harbour fantasises of being found out, sometimes in the most disgraceful of ways - a conflict between feelings of shame and a need for acceptance that can be satisfied, at least to some extent, in the safe environment of a secretarial game. You can use this to provoke your husband by taunting him with suggestions that are thrilling yet terrifying to think about, with the difference depending on how seriously they are taken.
For example, you might ask him what his colleagues would say if they could see what he was wearing or knew what he was having to do, answering that question by proposing reactions far too unprofessional to occur for real. You might wonder what his actual superiors would make of his shortcomings as a secretary, or suggest that his rivals or subordinates could do much better, perhaps even throwing the names of people he works with into the mix. Would any of them be able to see him as a man if they found out he was a secret secretary, or would he become the laughingstock of the office, perhaps being demoted to the most junior of roles? If your husband ordinarily holds a prestigious position, you can tell him that he doesn't do so any more, not since you discovered that he was really a secretary, perhaps going so far as to usurp his title for yourself. As well as throwaway comments, such themes can be used as the subjects for lines, reports and presentations, requiring a submissive man to really consider them.
If your secretary will be working on a computer, you can have it configured to accost him with alarms, perhaps at frequent intervals, which might remind him of his status or hint at further fun. Mobile phones can be set up similarly, or you might simply message him from time to time. If he's going to be opening and closing a lot of documents, you can change the desktop background to an image or slide show that will provoke him whenever he sees it, which needn't be anything more explicit than some large, unmistakable text. For a subtler effect, create folders with suggestive titles, requiring him to acknowledge what they're telling him every time he clicks between them. Files can follow a similar pattern, perhaps prefixed by your secretary's emasculating name or title. Alternatively, you might set a screen saver on a short timer to scold him for not staying busy. A particularly wicked twist is to make this lock with a password that only you know, seeing your secretary having to come to you each time it activates - something you needn't necessarily warn him about in advance!
How can I inspect my secretary's clothes?
One way of seguing between professional and more intimate activities is to subject your secretary to a clothing inspection, which you can insist upon at any time, no matter what he might be doing. Merely having your husband stand in front of you so that you can consider his outfit will stress his submission, even if he's wearing nothing more embarrassing than trousers and shirt. Does everything meet your expected standards? You needn't be reasonable if you're looking for a pretext to take things further, nor need you tell him straight away - instead, you can make him wait for as long as you like, as well as having him turn and stretch, or else prodding and poking him for no other reason than to assert your authority. A clothing inspection provides a perfect opportunity for talking to your secretary while you have him on the spot, but it doesn't have to become anything more. Should you tire of playing with him, you can simply send him back to work, perhaps with a flea in his ear about not wasting time standing around. Doing so will keep him on his toes, thanks to there always being a possibility that an impromptu inspection might become something more - whether pleasurable or otherwise!
In a real office, it would be mortifying enough for a secretary to be called out on her skirt or blouse, let alone to be challenged about her underwear. Sissy secretaries do not work in real offices, however, and so can be instructed to strip so that their lingerie and hosiery can be scrutinised as frequently as might amuse. Having his skirt around his ankles puts a man in a very vulnerable position, even without him having to hold open his blouse to expose the full extent of his emasculation. Is he wearing what you want him to? That needn't be the same as you might have told him earlier, with colours and styles offering plenty of potential for putting your secretary in a no-win position. Even if you haven't unfairly changed your mind about the relative merits of nude versus black nylons, it's easy to find fault with a man's efforts when he's unfamiliar with women's clothing, let alone if you go out of your way to find issues.
Are his stockings free from snags, their tops level, and any seams perfectly straight? If his hosiery needs garters, are they securely fastened, over or under his panties in accordance with your preference, and with the straps properly adjusted? Is any hair visible where it shouldn't be? What about bulges or damp patches betraying an unprofessional degree of arousal? Many of these questions invite attention to a man's crotch, but you needn't limit that to just your eyes, using your hands to assess, arouse or admonish. Turning him around, you can similarly fuss with the back of his panties, checking that they're not wedged between his cheeks, straightening the leg openings and making sure that the laundry label is tucked in. Of course, if you're feeling wicked, you can create such problems, subsequently scolding your secretary for his slovenliness even if he was wearing his underwear perfectly before you interfered! Garter clasps can be unfastened and refastened on the pretext of properly securing them, whereas their straps can be shortened, lengthened or simply snapped against the skin, as can those of a bra. Do your ticking fingers cause the man you have at your mercy to wriggle or gasp? That can be grounds for a punishment, if only in the form of a swift slap to a buttock or thigh - after all, a sissy secretary needs to be able to remain both still and silent during an inspection, no matter how much his boss might provoke him!
If you're wanting to have a different sort of fun, you can tell a sissy secretary that his choice of clothing is far too suggestive or sexy, and that you're going to have to have your way with him as a result. Lacy underwear, an unprofessional colour bra, or simply the fact that he's wearing stockings rather than pantyhose can all be used as excuses for this, perhaps presented as being his choice even if that's not the case. Does he think that he'll be promoted if he pleases his boss? To make such a scenario more provocative, you might tell your secretary that he'll be going straight back to work after you've finished with him, or that doing what you want is the only way of avoiding a formal disciplinary procedure. From a practical perspective, having his trousers or skirt already down puts your husband in an ideal position for you take advantage of his arousal, but you can equally demand that he sorts his clothes out before pleasuring you, scolding him for letting you see him in a state of undress. Once again, that's thoroughly unfair, but submissive men often find such unfairness excitingly thrilling!
How can I have sex with my secretary?
Despite professing a desire to please, submissive crossdressers can be very self-centred, but that doesn't mean that a secretarial session should be solely about a man's satisfaction - quite the reverse! Even if you have your husband stay in a skirt, there are plenty of ways that he can provide pleasure - indeed, being restricted by what he's wearing will require him to use other parts of his body, with the connotations of his outfit also encouraging less selfish lovemaking. Despite insisting that he stay fully dressed himself, you might extend your personal assistant's responsibilities to include removing some of your clothes, perhaps having him kneel as he helps you out of them so that there can be no doubt about who's in charge. It's up to you whether you instruct him to pay further respect while he's down there, or merely make him wait until you've finished with the toy you've had him fetch. If you're feeling particularly wicked, you might even send him back to work, perhaps requiring him to concentrate on a challenging task while you taunt him with sighs of satisfaction. The resulting frustration will ensure that he'll be eager to please whenever you're ready for more - even if, by then, he's back as a man.
There are two positions stereotypically associated with sexually submissive secretaries, in so far as men's fantasies are concerned. The first of these puts the assistant under the boss's desk, with any discomfort that might result from having to crouch in a cramped space being of no concern to the secretary's superior. Several factors combine to make this a provocative scenario, regardless of which role a man might dream of adopting. For starters, there's the obvious power imbalance, which extends beyond one party being able to sit back while the other must kneel. The secretary is providing a service, but not one that will necessarily be rewarded, perhaps being expected to return to work without even a word of thanks afterwards. Despite the intimacy of such an act, which is made more thrilling by taking place in a taboo location, it may be presented as just another duty, with the secretary's continued employment contingent on delivering a satisfactory result. Moreover, the desk imposes restrictions of its own, as does the boss's chair, permitting someone considering such a scene to conclude that the submissive party has little choice but to oblige thanks to being physically trapped. That can be powerfully arousing for men who fantasise about being made to do things they have mixed feelings about, or who delight in becoming powerless.
You don't need to have a desk to turn this scenario on its head - a regular table will suffice, even if it's not enclosed at the sides or the back. Indeed, you don't even need a table, and can get away with using a sofa or the edge of a bed in place of an executive chair. If you're using furniture that can be easily moved, you might position it so as to put a wall, if not a corner where two meet, immediately behind your secretary, thus leaving him no place to go. All that really matters is that you're able to sit comfortably while he adopts a submissive position. To heighten his sense of being helpless, you might rest your feet on your secretary's back, perhaps spurring him on with the heels of your shoes, or bring your hands to his head to make clear where you expect it to stay. You needn't give your husband permission to touch your body any more than is absolutely necessary, however - indeed, you might instruct him to keep his own hands clasped behind his back, if not tie or cuff them there. Even a symbolic restraint will emphasise a man's submission, but binding his legs as well, perhaps with worn-out hosiery or a necktie, can leave him genuinely immobilised.
If you're more interested in humbling a sissy secretary, consider donning a strap-on, or simply hold a dildo in your lap before directing him to start bobbing his head. Seeking to pleasure a piece of plastic might seem pointless, but the very pointlessness of such an act gives it a psychological power, quite apart from the shame a man may feel about performing in a supremely submissive way. The latter can be very intense, even for submissive crossdressers excited by the idea, but even if your husband has no qualms about giving rather than receiving, he'll struggle to speak while his mouth is occupied. That makes such a position ideal for having a one-sided discussion with him, perhaps regarding matters unrelated to your role-play. How can a man argue when he finds himself on his knees, his head held down as he's addressed from above? If he doesn't agree to whatever you're proposing, it only takes a little pressure to make him gag, but if you'd rather sit back and relax, you needn't have him kneel in front of you at all! An empty chair can serve as a stand-in, requiring him only to hold a dildo to its seat, as can the floor at your feet, the latter seeing a sissy secretary having to present his behind while he's bowed down. You might set him a certain amount of time that he must spend engaged in such an emasculating activity, or simply tell him to continue until you say otherwise - either way, he'll soon come to appreciate the effort involved.
The other position that secretaries frequently find themselves in, at least, according to the clichés of pornography, is bent over the boss's desk. Again, such furniture restricts the submissive party, this time by providing a surface that the recipient of a superior's advances can be pinned against. Regardless of whether that's face up or face down, the uncushioned surface won't offer much in the way of comfort, nor even anything to clutch. Indeed, it may be littered with paperwork or other office paraphernalia, adding an exciting sense of abandon, tinged with indignity, for the secretary who will be expected to put everything right afterwards. A desk is not designed for lovemaking, but it always has the potential for being an impromptu location for sex, needing only a secretary's skirt to be pulled down in order for the boss's needs to be satisfied. In the safe world of fantasies, that permits provocative thoughts of using or being used at any moment, without any of the niceties that would normally precede or follow intimate activity.
As before, you can use a table in place of a desk, albeit noting the need for it to be sturdy enough to avoid any risk of collapse! Alternatively, you might make use of a kitchen counter or even the back or arm of a sofa, requiring your secretary to position himself at a height that's convenient for you, if not necessarily for him. He'll need to face you if you want to do things the traditional way, but that still offers the choice of him standing bent backwards, or mounting the surface and spreading his legs. Either way, you'll be able to set the pace, adopting a rhythm that maximises your pleasure rather than his. If you're still concerned that he won't last, or simply don't want your husband to enjoy such an encounter too much, you might instruct him to wear a sleeve or sheath, or alternatively, have him substitute his sex with a strap-on or even just a toy that he must hold against his skirt. Combined with a chastity device, the latter will make for a very frustrating, emasculating experience for a man, no matter how much it might do for you!
Rather than have your secretary penetrate you, you might reverse that too, perhaps even requiring him to equip you with the means of taking him in advance adopting a suitable position for you to do so. You don't need to do that straight away, of course, but can make him wait for as long as you like, leaving him having to maintain an uncomfortable, vulnerable stance. Another option is to instruct him to work until you decide that you're ready for him, perhaps with his buttocks bare so that he only needs to stand. An ideal task is one that is too tedious to stop his thoughts from wandering, yet still requires concentration in order to complete correctly. Any mistakes caused by anticipation of what's coming can be used as a pretext for punishing him with your phallus, even if receiving it is really a reward for him. As with satisfying a dildo orally, many submissive crossdressers find the idea of being penetrated to be both intensely shameful and yet supremely exciting - all the more so if the experience is deliberately made demeaning or degrading. With that in mind, you might heighten your secretary's feelings of helplessness and humiliation by holding his head down while you have your way with him, perhaps even pressing his face into his work as you scold him about his failings. Alternatively, you might insist that he try to continue with whatever he's supposed to be doing, as impossible as even the simplest of tasks will become in such circumstances!
While a sissy secretary must never masturbate when he's supposed to be working, that doesn't mean his boss can't lend a hand - even if that's only to make matters harder for him! An entertaining approach is to precede this with an underwear inspection, requiring your husband to drop his trousers or skirt so that you can search for any sign of unauthorised arousal - the latter being all but guaranteed if you've played this game before. Having garments bundled around his ankles will hamper his ability to go anywhere, not that that need stop you from instructing him to do so. To emphasise his submission further, demand that he keep his hands on his head, a desk, a wall or even his keyboard, or have him hold something - a stack of heavy books works well for ensuring he can't do anything himself! You might instruct him to bend over as discussed before, putting you in a position of power should you stand behind him, but you might equally remain seated, once again requiring him to position himself for your convenience.
Whichever way you choose, you don't need to take him to completion - indeed, you don't need to touch him at all, instead having him start and stop at your command. No matter whose hand might bring him repeatedly to the brink, however, such edging will engender a very receptive state of mind, as well as train him to last longer, especially if there are consequences for him climaxing without permission. The natural comedown that we discussed earlier may be sufficient to discourage your husband from disappointing you, should you remind him how failing to exert the necessary self-control is likely to make him feel, but you might also threaten not to play such games if he can't be trusted not to let you both down. Alternatively, you can propose keeping him as a secretary long after he's forgotten any fleeting pleasure he might enjoy from succumbing, telling him that it's his choice whether he finds what he'll be doing afterwards exciting or shameful. In fact, whether he disgraces himself is as much in your hands as it is in his, something you can stress by telling him that, as a secretary, even his orgasms belong to his boss! To reduce the risk of overstimulation, you might separate intimate sessions with more mundane activities, perhaps taking advantage of advertising breaks if you're watching television while your husband works, or alternatively, having him schedule appointments with you at suitable intervals throughout an evening.
How can I punish my secretary?
As we suggested at the start of this chapter, it's unlikely that many actual assistants find themselves having to type lines in order to atone for their failings or to deepen their sense of subordination. Nevertheless, such an activity wouldn't immediately raise eyebrows - indeed, without seeing what was being typed, a casual observer might think that a secretary so occupied were merely engaged in regular work. Of course, a man would attract more attention if his face were flushing with shame as he undertook such a pointless task, let alone if he were wearing women's clothes, but even then, a passerby might not fully appreciate how he was being punished.
That's not the case in the fanciful world of pornography, however. Perhaps because the oppressive tediousness of having to type the same words hundreds of times cannot be easily captured on camera, subtle punishments are generally eschewed in favour of conspicuous ones, usually with strong sexual overtones. An errant assistant may have skirt and panties pulled down before being bent over a desk - if not to be roughly taken, then to receive a spanking or paddling. Many of the motifs we previously considered in the context of secretaries servicing their bosses are present in pornographic punishment scenarios, sometimes to an even greater degree.
Once again, there's an obvious power imbalance, with the submissive party needing to adopt a position that stresses this, perhaps for the dominant party's pleasure. The discomfort of the desk is not only accompanied by that inflicted by a hand, if not a more devastating instrument of discipline, but also the psychological shame of being physically punished - something that's demeaning for an adult even in private, let alone in the more public setting of an office. Even before such a punishment begins in earnest, there's nothing dignified about having to stand with one's skirt or trousers around one's ankles, revealing one's intimate attire in the process - especially if that intimate attire is especially embarrassing! Afterwards, there's a soreness that must be concealed from colleagues, assuming that's both permitted and possible, yet a recently chastised secretary might be glad to be unceremoniously sent back to work. Like the severity of a punishment, its duration is entirely down to the boss to decide, both perhaps disproportionate to whatever crime was chosen as a pretext for reinforcing the office hierarchy.
Such themes can make for exciting daydreams, especially for submissive crossdressers who harbour feelings of shame or guilt about their desires. A stylised punishment simultaneously provides an opportunity to atone for wanting to be emasculated or humiliated, and also to indulge such inclinations. While it may seem odd to think of a man deliberately inviting discipline, if your husband has a penchant for punishment, he may misbehave or make mistakes in the hope of being provocatively chastised. As with suggestions of getting intimate with him while he's your secretary, however, there's no obligation to do anything of the sort should it not appeal - after all, you might find the idea of inflicting physical pain on someone you love to be unsettling. Indeed, it may not take much to disabuse a man of such notions himself, at least temporarily, it often only needing him to be given what he thinks he wants for him to change his mind! While genuinely disagreeable discipline can make for an effective deterrent, you might use more playful, stylised forms of punishment as a reward, making your secretary suffer only so far as is pleasurable - both for him, and for you!
That might mean interrupting his work on a preposterous pretext, perhaps finding a failing that your secretary couldn't possibly have prevented, and insisting that he must be punished for it. For example, rather than just asking your husband to fetch you something, you might criticise him for not having done so already, insisting that he bend over because he didn't read your mind. He doesn't even need to drop his skirt or trousers, although that can add spice if he'll subsequently have to shuffle away - a symbolic swat to a covered cheek can be enough to thrill a submissive man, while also reminding him who's in charge. You can turn this into a ritual, requiring your secretary to say thank you as he acknowledges that you're the boss, or else have him apologise for his shortcomings and promise not to let you down like that in future - even though he will, perhaps no more than a few moments after he's sat down again.
Bending over a desk isn't the only position that a sissy secretary can adopt prior to a spanking. Instead of moving his chair out of the way after he's abandoned it, you might instruct your husband to push it in, such that he can clutch its back. Although doing so will provide similar stability, it puts more distance between the man being punished and his work, making it easier for him to consider whatever may be on his desk or computer screen. You can take advantage of that by having your secretary transcribe a few words in advance of his discipline, ideally in large text so that he won't have any difficulty reading them no matter how teary his eyes might become. Did you catch him in the act of looking at something he shouldn't? If so, you might conclude that he should consider it at length, while he's suffering the consequences! Images or videos of secretaries, male or female, showing their submission are another alternative, or you might simply confront him with an imperfect piece of work, if not one that still needs finishing.
The edge of a table, the arm of a sofa or even a wall can also serve as places where a man can put his hands while submissively presenting his posterior. Rather than allow your secretary any support, however, you might require him to bend over on the spot, challenging his balance even before you begin. Touching the toes is something that many men have trouble doing at the best of times, with a bulky bra or restrictive blouse only adding to their difficulties, quite apart from the unbalancing effect of high heels. Having his head upside-down will disconcert your secretary both physically and psychologically as he looks at his feet, with it being likely that he won't be able to stand perfectly still - certainly not for an extended length of time! Is he bending over far enough for you, without disrespectfully wiggling, or are those further reasons for him to be punished? You might permit a soon-to-be-spanked secretary to grab his ankles, or in the absence of sufficient flexibility, his knees, expecting his hands to remain there for the duration of his discipline, if not for a cool-down period afterwards. Alternatively, you might regard the slightest touch of his legs as grounds for additional punishment, a rule which can be justified as being necessary to avoid him snagging his stockings.
Another stereotypical position sees a submissive secretary spread over the boss's lap, perhaps being held down or having an arm twisted to keep them there. Again, this is likely to prove physically and psychologically challenging for your husband, seeing him having to consider the floor as he tries not to squirm. Moreover, such an arrangement will put his manhood in contact with your legs, announcing any arousal even if you don't choose to trap him between your thighs. To add to his sense of helplessness, you might insist that his skirt or panties stay around his knees or ankles under penalty of further punishment, reducing the extent to which he can flail his legs. Sullying your clothes can be considered as another reason for extending a spanking, but if you'd rather avoid him doing that, you can still bare his buttocks - simply bunch his underwear into his crack, or have him wear a cheekier style. Since he's the secretary, he's the one who should have to work to make things easier for you, rather than the reverse, even when it comes to discipline. If he can't find a position where you can comfortably support his weight, however, you might make use of the arm of a chair, or sit on the edge of a bed and have him lie across you. You don't even need to be underneath your husband as he sprawls over a suitable piece of furniture, such that you might remain standing as he adopts a very submissive, humiliating position across an uncomfortable chair.
For a playful spanking, a lightweight implement is perfectly adequate. If you don't want to use your hand, you might consider rolled-up paperwork, which will make more of a noise than it will inflict pain. The symbolism of being spanked with an inadequate piece of work won't be lost on a sissy secretary, even if his behind is left relatively unscathed. For slightly more of a sting, you might use a plastic ruler, which can also be brought to bear on the palm of a hand - a punishment that, as well as needing next to no preparation, also requires an errant secretary to put his hands where they can be seen, making it appropriate for catching him fiddling. A plastic fly swatter will also sting, especially on bare skin, with its intended purpose making receiving it more demeaning - something that you can stress to heighten your secretary's humiliation, even if you only tap him with it. Such an implement can be safely used on other parts of his body, provided you don't apply an unreasonable amount of force. A light swat to a shoulder can be used to motivate a seated secretary to type more quickly, whereas his calves can be targeted should he fail to sit or stand sufficiently still, neither requiring him to remove any clothing. Even without touching him, a fly swatter offers plenty of scope for mischief, proving annoyingly distracting when brought between a man at work and whatever he's trying to concentrate on!
Shoes and belts can serve as makeshift instruments of discipline, so long as you take care to avoid striking with a sharp heel or buckle. Both have a psychological significance, regardless of whether you use one of yours, your secretary's, or something that he might wear as a man. If the shoe or belt in question is part of his outfit, he'll have to remove it prior to you using it, but if you want to humble your husband further, you needn't allow him to put it on again afterwards! A long belt can be folded in two to create a strap that is suitable for applying to the palms as well as the buttocks, with a narrower belt having more of a sting. A hand strapping will permit your secretary to face you during his punishment, presenting him with the dilemma of where to look. Should his eyes or hands wander from where you want them, you might deliver extra lashes, noting the importance to avoid the wrists or fingers. Alternatively, you might instruct your secretary to turn around, so as to offer you a larger target!
Heavier, sturdier implements should be restricted to the fleshy parts of the buttocks. A wooden hairbrush is a traditionally feminine instrument of discipline, carrying powerful connotations even before it makes contact with a submissive man's bare behind, yet it is something that both businesswomen and secretaries might plausibly have to hand. While a casual observer might think nothing of such a brush were they to see it on a desk, a sissy secretary will regard it rather differently once he knows what it can do, with the mere presence of a hairbrush sure to have an effect even if you have no plans to use it. You might therefore place one between your secretary's keyboard and his screen when he's typing, perhaps repositioning it occasionally to add to his apprehension. The same can be done with clothes brushes and bath brushes, although these are less in keeping with an office setting, not that your secretary is likely to want to argue that point should you prefer an implement with more heft or swing. All have bristles that can be brushed across scorched skin after you've finished spanking him, with even the slightest of touches likely to prove far from comfortable!
Finally, there are implements specifically designed for discipline, such as paddles and canes, which might paradoxically appeal to submissive men because of their associations, despite being out of place in all but the most fantastic of offices. A detailed discussion of these is beyond the scope of this book, but the same general principles apply. Any implement can be given more significance by requiring your secretary to fetch it, or even hold it for a period of time prior to a punishment. Further rituals can be adopted during his discipline - for example, having him count, offer thanks or ask for each spank. Afterwards, you might make him wait to be dismissed, or expect him to explain, in his own words, how and why he was punished. Anticipation, both of the punishment as a whole and of its individual parts, can be as dreadful or as thrilling as the pain, so there's no need to hurry. Indeed, with anything new, it's best to go slowly, taking into account that the effects of a spanking won't necessarily all be apparent immediately, but may develop over time. Some men bruise easily, and even if your secretary doesn't, he may be sore for several days.
A serious spanking can swiftly reduce a man to tears, especially if he's encouraged to be less stoical than would be expected of him were he not playing the part of a secretary. Even preposterously theatrical gasps and groans will acknowledge his emasculated role, however, such that you might instruct your secretary to beg for mercy or cry like a girl regardless of how lightly you touch him. Conversely, you might forbid any unauthorised sounds or squirming under penalty of further indignities, expecting your secretary to take his punishment like a man regardless of whether he's dressed as one! A spanking of any kind is a perfect opportunity to talk to your husband, with his submissive position making it difficult for him to answer back, even as your hand or paddle gives whatever you say a greater power.
Like sexual relief, a ritual spanking can form the final part of a secretarial session, perhaps being presented as the price that a crossdresser must pay for the privilege of wearing women's clothing. A spanking after a climax is likely to prove even more painful for a man previously driven by his desires, whereas subsequent penetration will emphasise his soreness along with his submission. Alternatively, you can simply send your secretary back to work, perhaps to write up his punishment, promising more of the same if his efforts aren't satisfactory. You might even spank your secretary before he starts, telling him that you're having him make payment in advance for the mistakes that you know he'll inevitably make!
How can I distract or humiliate my secretary?
Even the softest of panties will do little to soothe recently spanked buttocks, let alone underwear deliberately chosen to be disagreeable. Separate to any other punishment, however, you can make sitting less comfortable for a sissy secretary by swapping his chair for an uncushioned one, or by putting a board or even just a large book between him and his seat. A backless stool can prove surprisingly challenging for a man used to slouching, especially if he is wearing high heels, but a regular chair needs only something uncomfortable attached to its back to discourage a secretary from sitting slumped - a golf or tennis ball in a counterbalanced carrier bag is quite sufficient for this.
Alternatively, you might insist that your secretary keep something held between his knees, tucked under his arms, or balanced on his head to encourage better posture - ideally an object that will announce its fall, such as a sheaf of papers, allowing you to monitor compliance from a distance. Noting that it's not healthy for a typist to regularly adopt an awkward position for prolonged periods of time, you might nevertheless have your secretary temporarily lower an office chair as far as it will go. This will not only require him to sit with hunched shoulders and bent legs, but also will also add to his sense of inferiority. If that's not an option, a similar effect may be achieved by raising your secretary's keyboard and screen, or simply by having him kneel in front of his desk.
More provocatively, you might insist that your secretary take a plug, which will make him aware of what he's sitting on even if you don't use it to prepare him for penetration. Such an imposition won't be visible under trousers or a skirt, but a man won't be able to forget it regardless of what else he is wearing, especially should it be combined with other ways of making a chair uncomfortable. You might schedule regular checks to confirm the plug's continued presence, requiring your secretary to bend over and spread his buttocks to show you, or alternatively, take it for granted once it's in. A thong can be added to ensure that a plug remains in place, with disagreeably tight underwear capable of proving aggravating in its own right. Insertion and removal of your secretary's plug can be delegated to him, although taking care of the former is a great way of asserting your authority. You might consider having him wear a plug for a set period of time as a punishment for not sitting still, or until he completes a task to your satisfaction, something which is likely to be harder for him because of the distraction. If you and your husband are not familiar with such toys, err on the small side until you get a feel for what he can take, and allow him to use plenty of lubrication.
A suitably experienced secretary can plausibly wear a plug at work for real, perhaps in advance of returning home to further fun, but the same can't be said for a gag. There's no hiding something stuffed in the mouth, even if that's nothing more than a pair of panties employed as a makeshift means of stopping a man from speaking. Stockings and pantyhose can be used similarly, if only symbolically, having a sexual charge whether you use yours or his. Holding a pen or pencil between the lips might seem too easy to be effective as a punishment, but keeping it there will slowly but surely become very challenging! A sissy secretary can be similarly humbled with an envelope or even a piece of paper, especially one bearing a shameful statement, both serving as a pretext for further punishment should he dampen them with drool, let alone smear them with lipstick. As well as having your secretary sit in such a state of disgrace while he works, you might also insist that he do so during discipline, or even have him bring a finished report to you as a dog might a newspaper, requiring him to crawl on his hands and knees to present it.
More formal gags can also be used to punish a sissy secretary who answers back or speaks out of turn, or simply to emphasise his submission still further. A traditional ball gag will not only reduce the wearer to an incoherent mumble, but will also see him suffer the disgrace of drooling. That offers yet another opportunity for additional discipline, regardless of whether he sullies his blouse or some very important paperwork with his saliva. Like a plug, a gag can be very distracting, making it an ideal accompaniment to a task that requires concentration. Any sort of gag makes it easy to ignore what a sissy secretary says in favour of putting words in his mouth, but those that require a man to hold a dildo between his lips are especially humiliating. The psychological shame of having to suck a mock penis is compounded by the physical challenge of such an imposition, with longer phalluses tickling the back of the throat in a manner that can be hard to bear. A similar effect can be achieved by having your secretary hold a sex toy in his mouth. Being able to spit it out won't necessarily make holding it any easier for him if he knows there are consequences for letting it slip!
A man doesn't need to have breasts in order to wear nipple clamps, it only requiring him to briefly unbutton his shirt or blouse to allow them to be applied. Again, that's a task that you might delegate to your secretary! The resulting pinch will distract him no matter what he's doing, but the effects of nipple clamps don't end as soon as they're taken off, with the sensitivity they leave in their wake ideal for fondling through a silky blouse or bra. You might instruct your secretary to present himself for their removal after a set period of time, which he'll likely be very punctual about, however inconspicuous such clamps might appear beneath his clothes! Clothespins can be used similarly, but can also serve as entertaining impromptu earrings, as well as adornments for a submissive man's nose, lips or more intimate parts of his body. Whether you use formal clamps or more makeshift ones, be cautious about how long you leave them in place for - a few minutes is more than enough to have an effect!
A sissy secretary may be marked as such, with the forehead providing the perfect canvas for either pen or lipstick - although you should first check that whatever you're going to use will easily wash off! You can tell your secretary how you're titling him, perhaps even writing backwards so that he's obliged to read a shameful moniker in a mirror strategically placed on his desk, or leave that a mystery for your amusement. Writing on the back of his hands will also require him to confront a message, especially if he's still a hunt and peck typist. Other parts of a man's body that can be written on include the cheeks, the chest (especially the part left exposed by a low-cut blouse), the buttocks, and even the private parts. A hidden message can justify regular inspection to make sure that it is still there, regardless of whether your secretary has had any opportunity to remove it. As well as asserting his role, you might sign your name, draw doodles or invite yourself to take advantage of him. As humiliating as it would be for a real assistant to reveal the words “spank me” when dropping her skirt, let alone to have a running tally of her mistakes on her forehead, such degrading treatment can be thrilling for a submissive man, requiring him to abandon still more of his dignity while further emphasising the power that his boss has over him.
We touched on having your secretary stand and wait for you to finish your coffee in the previous chapter, as real assistants might during a meeting in which their presence was only ancillary to that of their superiors. No matter what the difference in rank, however, even an assistant who was not permitted to sit wouldn't be expected to maintain an intentionally shameful position, in sharp contrast to some submissive men's fantasies! You can use the latter as a means of humbling your secretary by having him face the wall or stand in a corner, both provocatively unprofessional positions that would be beyond the pale in an actual workplace. Even a short period studying the wallpaper will seem much longer for a man who has no means of keeping track of time, especially if he's under strict instructions not to move a muscle! You can make corner time harder for an errant secretary by requiring him to balance on high heels, if not stand on tiptoe or on a stool, perhaps with his hands on his head, or keeping a coin pressed against the wall with his nose. A stack of books will only grow heavier the longer a sissy secretary has to hold them, but aching arms are no excuse for him risking sullying his shirt or blouse by not holding them stretched out!
Alternatively, you might have your secretary bend over and touch his toes, or even instruct him to kneel with his head down and his rear raised - with or without his trousers or skirt! Such positions will not only leave him feeling very vulnerable, but also make it seem as though he's inviting further punishment - something that won't be lost on him, even if you make no mention of it. As well as on the floor, perhaps in front of your feet, you might have your secretary adopt the latter position on a suitably sturdy table or desk. If you are punishing him for a poor piece of work, you might put that in front of him, or have him print out a shameful confession, such that he must consider it as he holds his humiliating position. If you'd rather that your secretary made more productive use of his time, you can provide him with a piece of text to memorise, whereas if his appearance falls below your standards, you might confront him with his reflection in a mirror. Regardless of which you choose, it's better to arrange things such that you can see him, should you deign to look in his direction, but he can't see you without drawing attention to himself. Doing so will add to his sense of vulnerability, thanks to the possibility that he could be being scrutinised at any time.
Some of these methods may seem cartoonish, bringing to mind the exaggerated discipline that a cruel headmistress might impose upon her charges in a work of fiction rather than anything a boss might use to encourage better performance in the office. In fact, the implausibility of a secretary having to stand in the corner or serve as a human notepad makes such over-the-top humiliation reassuring for a man subjected to it, leaving no doubt that he's in a very different world to one where letting his boss down might affect his career prospects - all the more so if he's being punished on a pretext, for his superior's pleasure, or even for his own. Moreover, a stylised punishment contrasts sharply with being forgiven, letting a man wanting to atone know when he's paid his penance.
These techniques also have the benefit of taking only a moment of your time to impose, yet are capable of affecting your secretary for much longer. Indeed, you might provoke him by pretending to forget how he's gagged as you press him for an answer, or by challenging him to explain why he has writing on his face. Can he handle being put in a deliberately unfair position with the patience and professionalism expected of a secretary, or will he warrant further punishment? There's a lot of fun to be had here if you're feeling mischievous!
Even if you're utterly preposterous about what you do to your husband, you can still pretend that he's working in a real office, making the humiliations we've considered here even more provocative by suggesting they might not be happening in private. In the next chapter, we'll look at ways in which language can be used to add authenticity to a secretarial session, regardless of what else that session might involve. If you'd prefer to motivate him more professionally, we'll also be exploring other approaches that can be borrowed from the world of business, as well as what to do if, no matter how ridiculous you are, your husband takes things more seriously than you would prefer.
