he's the secretary

Chapter 5: How can a sissy secretary be more realistic?

In the previous chapter, we discussed provocative, but thoroughly unprofessional ways of motivating a sissy secretary. As exciting as some men might find them, they are far from the only methods that can be employed to encourage or discourage certain behaviour. Indeed, in real offices, bosses are able to get results without ever having to resort to physical or sexual persuasion! Many of the more appropriate approaches they use are equally applicable to a man merely playing the part of a secretary in private, even though his motivation is likely to be rather different to an actual assistant. Whereas the latter may fear the financial consequences of being fired, for example, a submissive crossdresser won't want to lose a position in which he's permitted to wear the clothes he likes, with the possibility of such having a similar effect on what he does and doesn't do. Nor do many men want to incur the wrath of a wife, any more than they might that of a manager, all the more so should one woman be performing both roles.

A simple “Well done!” can mean the world to a man who has completed a challenging task, regardless of whether the work in question had any purpose. “What a dependable secretary you are!”, you might say, stressing the qualities you wish to see more of, if not proposing further opportunities for your husband to please you - whether as his secretarial persona or simply himself. That's especially important with a punitive task, not to mention the punishments we considered previously, where a kind word and a smile help make it clear that penance has been paid, even if you temper it with a warning that you don't want to have to resort to such measures again. Many submissive men take great pleasure in being helpful, and conversely, are pained when they feel they've let someone significant to them down, such that a disapproving look or disappointed sigh can cut deeper than any whip. “I know my secretary can do better than this”, you might chide, instructing your husband to justify your faith in him. Alternatively, you might express your doubts in his abilities, questioning whether you want to play with him if he isn't going to make an effort. “I thought you were meant to be my secretary!”.

More formally, you might record your secretary's successes and failures in writing. This might take the form of a simple document or spreadsheet, perhaps divided into two sections, to which a short note can be added whenever you are satisfied or dissatisfied with his efforts. Such a record can be maintained separately to the longer reports that we've previously proposed as possible secretarial tasks, having the benefit of summarising his performance in one place. Because it need only take a few moments to add an entry, you might do so yourself, perhaps even in pen, using a form that you've had your secretary prepare for the purpose. As well as allowing you to look back over his past performance, there's a symbolic power in putting something down in writing, which you can stress by referring to it as his “personnel file”, “employment record” or “work history”. For greater impact, such a form can be clipped inside the cover of a file of paperwork, or titled so that it appears first in a computer folder.

Whether in conjunction with a formal record or on a more temporary basis, you might award or deduct points from a running total. Such points don't need to translate into anything tangible, but can have an abstract, relative value that can be used to affect a man's perceptions regardless. Completing a lengthy piece of work might earn him just a single point, for example, because real secretaries' efforts are often inadequately acknowledged. Conversely, a momentary hesitancy to obey or lapse of respect might cost him ten, so as to emphasise the importance of submission. Is his appearance appropriate for his adopted role? A man unfamiliar with wearing women's clothing can be encouraged to consider it realistically by being given points for everything he gets right, whereas one who should know better about skirts and blouses can be penalised for even the smallest shortcomings in his outfit. You might score your husband out of ten, either when he first presents himself or as part of an impromptu or scheduled inspection, or alternatively, dock points for anything amiss as and when you see it. Tasks can be assessed similarly, with the resulting mark added to his total. Again, mistakes such as typos might mean immediate deductions - perhaps a point for every letter or word that is out of place, making it easy for a carelessly completed task to put a man in a worse position than when he started!

Even if you're thoroughly silly about it, such points have a surprising psychological power, making a very clear division between you, the superior doing the judging, and him, the subordinate being judged. To give points extra meaning, you can associate them with rewards or penalties, encouraging your secretary to work towards a target, if not to avoid the consequences of incurring too many demerits. You might set your secretary a threshold that must be met before you'll consider permitting him pleasure or allowing him to change, with that threshold perhaps increasing over time to reflect the inexorably increasing expectations that companies make of their employees. Alternatively, you might use the points your secretary accrues when deciding how many lines he must write or the number of times he'll be spanked. Of course, you can change your mind on a whim, increasing or decreasing his score, his target or the conversion ratio for no other reason than because you're in charge, or you can offer alternative options as a means for him to make the minimum - perhaps options that you had in mind for him all along.

A noteworthy achievement, whether that's your secretary meeting a longer term target or doing something successfully for the first time, might warrant a more substantial acknowledgement. That might mean having him print out a piece of work to put in his file, perhaps after you've added a few handwritten words of praise, a special stamp of approval, or even a colourful sticker. As daft as it might sound, gold stars can mean the world to a sissy secretary should they only be awarded for exception work! To take things further, you might dictate an accompanying memo in which you describe what he's done, or go so far as to award your secretary a certificate of recognition. Designing the latter can be set as a task in itself if you don't wish to use an online generator, but it needn't be especially fancy to be meaningful. It's unlikely that your husband will want to show such symbolic rewards to anyone else, especially if he's earned them through his submission, but that gives them a special intimacy. You can refer to them whenever you wish, not least to remind your secretary that he can do better on those occasions when his performance warrants nothing of the sort!

Some of these ideas may seem a little silly at first glance, but don't dismiss them out of hand - they're really not that different to how many companies seek to motivate their staff, merely extended into the make-believe world of the sissy secretary. Indeed, you might even blur the two, borrowing details from your husband's real workplace, if not your own, to add a provocative edge. Would he win an “employee of the month” competition were he to be pitted against other secretaries, perhaps seeing him come top of the typing leaderboard and thus having to provide a picture and a few paragraphs of text about why he's proud of his position? That might warrant a token bonus, albeit perhaps only redeemable for secretarial sundries such as stockings, or even the right to provide you with pleasure. The completion of a big project or an extended period of submission can be celebrated in similar ways, as can the anniversary of him first becoming your secretary. In real businesses, contrived attempts to create an overly chummy environment can leave workers feeling jaded when employed by out-of-touch management only paying lip service to caring, but tongue-in-cheek imitation offers plenty of scope for fun for a couple, as well as providing a man with a sense of perspective about things he might otherwise take too seriously.

How can language deepen a man's sense of being a secretary?

To help deepen your husband's sense of being a secretary, you can make use of the language of business, perhaps referring to the work you've set him as being a high-priority deliverable for a mission-critical project, even if you've only required him to type a few lines. Have his endeavours, as humble as they might be, contributed to a significant milestone or strategic objective? You might praise him for achieving a target, fulfilling a level of service, or satisfying contractual obligations, but only if his key performance indicators meet the requisite industry standards for a secretary of his grade. He'll need to adopt best practices and follow established conventions if he's to deliver results, let alone exceed expectations, which means showing initiative and being proactive - regardless of whether his duties are as professional as such language!

Perhaps his unwillingness to demonstrate the necessary dedication, an inflexible resistance to constructive criticism, or a disappointing lack of can-do attitude has caused a necessary prerequisite to fall behind schedule on the agreed timeline. A submissive man who fails to meet a deadline, concocted or otherwise, might be threatened with having to personally make things up to the principle stakeholder, if not explain the situation to the chief executive! It doesn't matter if the necessary prerequisite is your pleasure, nor that the stakeholder or executive is you, and you intend on having your secretary make things up to you in a manner unlikely to occur in many offices - again, you can be deliberately over-the-top. Indeed, you can be thoroughly unfair if you're feeling mischievous, requiring your husband to use formal terminology only to playfully mock him for it - after all, that important deliverable is really only a few lines of typing, something that any secretary worth her salt could rattle off in a matter of seconds. Conversely, you might scold him should he follow your lead and speak with the slightest informality, because a secretary must always be scrupulously professional. It's easy to trip a man up by being picky about words, putting him in a no-win position that stresses his submission.

Punishments such as standing in the corner or writing lines may be referred to as working overtime or staying late at the office, giving those concepts negative associations even if you don't connect them more directly. Will your husband want to risk earning himself more overtime at home because he couldn't leave his desk on time? Alternatively, you can emphasise the pointlessness of punitive tasks by describing them as make-work, paper pushing or red tape, even going so far as to explicitly call them time-wasting activities. Has your secretary wasted enough of his time to show that he's sorry for wasting yours, or does he need to waste even more in order to properly understand his place? A man in need of taking down a peg can have his efforts belittled even when they have substance, assuming you deign to show the slightest interest in whatever silly secretarial nonsense he's supposed to be doing. You might deliberately get even the broadest of details wrong with a view to provoking your husband to correct you, chiding him for being a fussbudget should he do so, yet scolding him for allowing you to get the wrong idea if he doesn't. Again, this allows a man to explore feelings of submission and unfairness in a safe environment where there are no long-term consequences for being humiliated by a superior.

To add a vintage air to your games, you might pretend that your husband has been assigned to you at random from the typing pool, a group of interchangeable secretaries that companies formerly employed to take care of typing letters, memos and other small pieces of work. Is he the only man among them? Do his efforts with his electronic typewriter (for that is all that a modern computer really is) compare favourably to those of his imaginary colleagues, or will you need to have words with the pool's supervisor? Depending on the work you set him, you might also refer to the equipment your secretary uses as an adding or duplicating machine, assuming it doesn't amuse you more to prefix those terms with “human” and apply them to him! If you want him to take notes by hand, you might instruct him to fetch his steno pad, whereas an email that you'd like him to transcribe can become a telegram or cablegram, with its address needing to be found from a rotary card file. You might use these old-fashioned words with your tongue firmly in your cheek, yet expect your husband to use them as though he really were a fifties secretary, no matter how daft it makes him sound!

Regardless of era, the stereotypical secretary always speaks politely and professionally, never betraying any emotion beyond an appropriate eagerness to please. To remain true to this archetype, a submissive man should suppress even the slightest hint of frustration, annoyance or impatience, remaining calm and composed no matter what the provocation. He should always choose the correct words, delivering them clearly and concisely, in a friendly, yet formal tone. Needless to say, he should eschew slang and overly technical terms! A sissy secretary should not mumble or gabble any more than his real-world counterparts would be allowed to, even when making shameful confessions or admitting to embarrassing mistakes. Nor should he talk about matters that are unrelated to his immediate work, including his desires or any discomfort, without good reason - indeed, you might make it the rule that your secretary must remain silent until you give him permission to speak, it being better that he is seen but not heard. Interrupting you, let alone answering back or arguing, might be regarded as an offence warranting swift and severe discipline! Naturally, he should adopt the utmost respect when referring to anything related to being a secretary, including his work and what he might be wearing. “Please”, “Thank you” and “Excuse me” should come to his lips as a matter of course - always with a smile, even when acknowledging difficult or unwelcome instructions.

Many men are used to speaking definitely about what they want or are going to do, putting an emphasis on themselves and their desires that is at odds with being a humble assistant. To sound more submissive, a sissy secretary might be required to couch his thoughts in conditional language, using “could” and “might” to soften verbs, and turning statements into questions that seek your approval. The latter can be made even more deferential by embedding them in other questions or statements, if not weakened with words like “perhaps” and “maybe”, such that “Can I stop now?” becomes “Could you possibly tell me whether I might be permitted to stop now?”. Rather than allowing him to use the active voice, you might prefer your secretary to eschew the first-person pronoun where possible, especially when announcing his completion of a task. Using the passive voice puts the emphasis on his work, or even whom he is working for if he adds an appropriate possessive, as can be seen by comparing “I have finished that typing” with “Your typing has been finished”. Of course, a submissive man shouldn't use the passive voice to avoid taking responsibility for his mistakes - unlike correct ones, incorrect words do not type themselves!

We will discuss titles and other terms of respect shortly, but it is not unreasonable to expect your secretary to end even the shortest sentence with an acknowledgement of your superiority, if only in the form of “Miss”. Should he need to say something, he might start with “I'm sorry to bother you”, “Forgive me for disturbing you” or “I apologise for the inconvenience”, or even ask whether you are willing to spare him a few moments of your precious time, assuming that isn't too much trouble for you. You might simply be sitting back and relaxing, but you can nevertheless require your secretary to pretend that you are very busy, such that the slightest effort on your part requires profuse thanks and apologies, both in advance and afterwards. Have you invited him to share an opinion? Even if you've merely asked him a simple question, you might have him weaken his answer with “I may be completely wrong”, “Please correct me if I have misunderstood” or “Far be it from me to say for sure”. It's hard for a man to feel confident, let alone in charge, when he must speak in such a submissive way, but you might require him to announce his subordinate position more explicitly - “I know I am merely your secretary, and so I must defer to your authority and accept what you say, because you're the boss and you make the rules”. If such words don't come easily to his lips, you might set them as lines, with repetition sure to teach him the importance of showing respect!

There's an implicit submission in remaining silent when someone else is speaking, but that isn't the only way a sissy secretary can demonstrate his deference without moving his mouth. You might encourage him to nod his head whenever you say something, regardless of whether or not you expect your secretary to accompany that with an obedient “Yes, Miss” to indicate both his understanding and agreement. The only exception might be if you are telling him what you don't want, in which case, a shake of his head would be more appropriate. Otherwise, you might require him to keep his head down in your presence, not permitting him to meet your eye except when he's making a significant confession. Having to look at his feet can be particularly humbling for a man whose chest boasts an unmistakable curve or whose legs are enveloped in sheer nylon, but adopting such submissive body language will have an effect on him regardless of what he's wearing, even without you going out of your way to fluster your secretary by alternating between “Look at me when I'm talking to you!” and “Don't you look at me like that!”. Is he fluttering his eyelashes with exaggerated frequency, especially when asking for something? If not, you might reject his request because of him not being submissive enough!

We saw in an earlier chapter how a tight skirt prevents a man from spreading his legs, with high heels also making it harder to adopt a confident stance. Your secretary doesn't need to wear women's clothing in order to stand to attention with his feet together, however, although having to roll his shoulders back will serve to emphasise any bust he may be burdened with - indeed, you might instruct him to flaunt his curves even if he doesn't have any! To ensure your secretary doesn't slump forward, you might insist that he clasps his hands behind his back, thus leaving his crotch vulnerable. While he won't be able to do that while typing, he can nevertheless maintain an upright posture that presents his chest to his screen, with a requirement to keep his knees pressed together further challenging his manhood. You might forbid your secretary to cross his legs, not only because it looks unprofessional, but also out of consideration for his health - after all, proper posture is essential for typists!

What can I call my secretary?

As men climb the corporate ladder, they often covet titles that convey a sense of importance, even when they're not at the level of “Managing Director”, “Senior Vice President” or “Chief Executive Officer”. The opposite is true for the sissy secretary, whose inferior status may be stressed with appellations from the other end of the organisational hierarchy. If your husband has yet to prove his worth, or has lost your favour through poor performance or misbehaviour, you might refer to him as merely a “trainee”, “intern” or “temp”, telling him that he'll need to show that he deserves to be regarded as anything more. From there, he might progress to becoming an “assistant”, “aide” or “helper”, or perhaps an “office junior”. To draw attention to the mundanity of his work, you might make him a “typist” or “clerk”, whereas to emphasise his emasculation, consider using “office girl” or even “gal Friday” as his formal title.

Increasingly, the word “secretary” is seen as old-fashioned, with those who might once have been called that preferring the likes of “executive assistant”, if not “administrative coordinator” or “office manager”. For a man wanting to feel submissive, however, any sexist connotations serve to make “secretary” more appropriate, especially when compared to anything that might suggest he's in charge. Of course, you can still use “coordinator” and “manager” ironically, perhaps preceding them with terms that negate their importance - something that can also be done with the other words we've been considering. These might follow the lead of actual job titles, either by relating to particular duties such as “typing”, “filing” or “transcription”, or by indicating the subordinate nature of the role by using “support”, “administrative” or “paperwork”. Believe it or not, it's possible to find positions advertised for genuine “paperwork coordinators” alongside “transcription assistants” and “filing clerks”, although few men would want to boast that they were employed as such!

Of particular note is “personal assistant”, which can take on a rather different meaning should there be erotic aspects to your husband being a secretary, even if only in his mind. It only takes an extra word to make that meaning more explicit, although you might reserve calling him your “very personal assistant” for when he's pleasing you more intimately. Similarly, some companies employ customer satisfaction assistants and client experience managers, designations which can easily be adapted to suggest less professional duties. Since a sissy secretary's title need never be known by anyone other than you and him, there's no need to hold back, such that you might promote your husband to “female satisfaction assistant” as and when required. To add to his awareness of his clothing, you might make him a “skirt and blouse coordinator”, whereas to assert his submission less sexually, you might draw attention to his limited responsibilities with a title as underwhelming as “paperclip manager”.

Any title can be made to sound less significant by preceding it with words such as “acting”, “apprentice”, “assistant”, “deputy”, “entry-level”, “junior”, “part-time”, “provisional”, “sub”, “temporary”, “trainee” or “understudy”, or by following it with similar in parentheses, if not “in training”, “unpaid” or “volunteer”. These can be combined even with titles which already include them, allowing a sissy secretary to become things as ridiculous as a “volunteer assistant deputy assistant (unpaid)” or “trainee junior office junior in training”. To indicate the peculiar nature of his position, you might throw in “informal”, “unqualified” or an ironic “special”, or add “male”, “sissy” or even “brassièred” alongside other words reducing his status. Does his job title need to note that he's been demoted, is under review, or on probation, or propose that he's only “level one” or “basic grade”? If you don't want to think about such matters yourself, you can leave coming up with suitable wording as a task for your secretary, but there's no obligation to stick with anything for longer than it amuses, even if you insist on him producing proper paperwork for it - after all, a sissy secretary is whatever his boss says he is!

You can stress your secretary's subordinate position by taking possession of him, whether by expecting him to refer to himself as “your secretary” when speaking with you, or by having his title include your name. That might make a sissy secretary “Mrs Masters's personal assistant” or “personal assistant to Mrs Masters”, with his part in that diminished still further if it's shortened to just “PA”. If you'd rather use a title of your own, you might adopt one of those we considered at the start of this section, at least for the purpose of defining his, perhaps embellishing it with the aim of stressing your husband's submission. How humbling for a man to have to announce that he reports to “The Head of Household Affairs”, “The Chief Financial Manager”, if not “The Director of Domestic Discipline”! Should those sound too stuffy for you, you might make yourself “The Sole Decision Maker”, “The Woman in Charge” or just “The Boss”. Again, these titles can form part of his, with something as simple as “The Boss's Secretary” highlighting the difference between your two positions.

Regardless of title, a subordinate should always address a superior with respect. Rather than your first name, therefore, you might insist on your husband using “Miss”, “Madam” or “Ma'am” when he's playing the part of a secretary, even when engaged in intimate activity. Alternatively, you might require an honorific such as “Mrs” or “Ms” followed by your surname, assuming you don't want to adopt a different name for the duration of your games, so as to reflect a persona that's much harder to please. Becoming the bossy Miss Stark, the uncaring Ms Stoneheart, or even the cruel Mistress Dreadmore means that you can temporarily pretend you don't have a history with your husband, instead regarding him as a temp that you've only just met - albeit one who must nevertheless meet your impossible standards if he's not to suffer the consequences! That's not only provocative for the man who finds himself having to report to such a character, but can also be a lot of fun for you, as well as allowing you to keep him on his toes. Moreover, you can refer to such an alter ego when not playing, even cryptically in front of other people, perhaps reminding your husband that he mustn't be late home from work because of his appointment with her - an appointment that will see him regret being tardy!

Even if you don't permit your secretary to use your first name, you can still address him by his - indeed, including it in questions and instructions can add to their impact, especially when done with exaggerated frequency or tone. You might, however, ironically reciprocate his respect by calling him by a surname, either with or without a title. The absence of the latter implies an impersonal formality that's well-suited to a secretary who will never become intimate with his superior, whereas a “Miss” or “Ms” will emasculate a man even if he's not wearing women's clothes. “Miss” is particularly effective in this respect, as a result of the connotations that see it being eschewed by many modern women. Conversely, a stressed “Mr” can be used to cut a cocky crossdresser down to size, not only reminding him of his sex, but also the importance of remaining professional. Any of these may be followed by a surname that's in keeping with his adopted character, be that so plain and ordinary that he could be one of countless unremarkable namesakes, or preposterous enough that he'll struggle to say it with a straight face. Depending on the mood that you're wanting to set, you might consider puerile double entendres or prim and proper double-barrelled names. That might see your secretary having to announce himself as anything ranging from “Miss Smith” to “Miss Beauchamp-Montgomery”, assuming he isn't expected to answer to the likes of “Miss Cox” or “Miss Redbottom-Smallcock”.

Along similar lines, a man can be given a different first name when he's playing the part of your secretary, helping him to adopt an associated character. This might be nothing more than a feminised form of what he's usually called, perhaps requiring only a slight change in pronunciation, as is the case when Daniel becomes Danielle, or it may be completely dissimilar, so as to emphasise the distinction between your husband and his secretarial persona. If he has a history of crossdressing, he may have a name that he likes to think of himself as when wearing women's clothes, which you might use if suitable, or adapt if not. As with surnames, you might pick something particularly plain, even looking back into the past to find names that sound dated or dowdy - searching for names from previous decades will yield plenty of possibilities. Is he an Agatha, a Susan, a Katie or a Brittany? Alternatively, you might consider those that are more suitable for strippers, for example, Brandy, Mercedes or Sapphire, if not the sort of name one might give to a pet, such as Cookie, Mittens or Pumpkin. You can even make him use a suggestive or sexist nickname “officially”, as emasculating as it is for a man to have to assert that he's really called Cutie Pie, Dollface or Honeybun when filling in forms. Once again, finding possible options can be set as a task for the man who'll be answering to whichever amuses you most. So long as it helps your secretary get in the desired frame of mind, it doesn't matter how implausible a name might be, although if you do choose something silly, you might remark on the difficulties it would cause in a real office - Kitten Snugglebum won't be getting promoted any time soon!

Even secretaries who work freelance are employed by businesses of one form or another, ranging from single businesswomen right through to huge corporations. Moreover, they may be expected to engage with clients, customers and suppliers of a similar nature, if only on behalf of their bosses. You can add greater realism to a secretarial scene by pretending that your husband does the same, whether you make up the details or borrow them from actual companies - noting, as always, that such work can be delegated to the man in question. Job adverts offer ready-made positions that he might adopt, if only temporarily, with company websites providing a wealth of material that can be drawn on for related tasks.

Blurring the boundary between fantasy and reality can be very provocative - indeed, you might assign your husband's alter ego to a business deliberately chosen to affect him, such as a modelling agency or a manufacturer of intimate attire. Conversely, having to imagine that he's working somewhere especially uninteresting can be used as a means to restrict his activities. Would a faceless financial company tolerate a temp who dressed inappropriately, turned up late, or was more interested in touching himself than typing? A collection of random letters followed by “corporation”, “enterprises” or “group” might emphasise that his work isn't going to be exciting, as might one or more surnames followed by “and associates”, “and partners” or “group”. Of course, a sissy secretary shouldn't expect his own name to form part of such a list, any more than a temp would expect to be a partner or associate!

What if he wants to become a secretary for real?

There's no reason why a man can't really work as a secretary - indeed, some do, with many more assisting their superiors in other capacities. Despite the stereotypes we've been drawing upon, there's nothing fundamentally feminine about typing or transcription, let alone the more challenging tasks that office administrators and personal assistants take care of, day in, day out. If a secretary works from home, perhaps as a virtual assistant, no-one need know whether they're male or female, nor should that make any difference. The demands of a business remain the same regardless, it being the ability to address those demands that's important - just like with any other job.

Throughout this book, we've distinguished between actual secretaries and the deliberately exaggerated caricature that we've referred to as the sissy secretary, stressing that the latter exists in a make-believe world that isn't necessarily subject to the same rules as the former. Unfortunately, this is something that submissive crossdressers drawn to secretarial fantasies easily forget, with such men often ignoring how they only selectively imitate elements in their pastiche - in particular, omitting those that don't appeal on at least some level. A submissive man may desire demeaning treatment or discomfort, but only in so far as that satisfies a deeper need for him. It is unlikely, however, that his daydreams will extend to struggling to get to work on time in rush-hour traffic, or worrying about saving enough from an already stretched wage packet to bridge the gap between one short-term contract and the next - frustrations that have none of the redeeming qualities of wearing disagreeable, yet arousing clothes, or performing challenging tasks that are similarly charged, whether sexually, psychologically or emotionally.

A man seeking to escape the pressures of another job might toy with the idea of becoming a secretary more seriously, overlooking the obvious problems of trying to live out a fantasy for real. No matter how much he might think otherwise, it's unlikely that such a man is considering working as an actual assistant, with all that that entails, but rather as a sissy secretary - roles that are by no means interchangeable! Employers have no need for, nor interest in, someone who merely wants to play around, any more than real secretaries would take kindly to being asked to perform a mockery of their role - after all, the latter have their own share of stresses, albeit often going unnoticed by the superiors that are frequently responsible for them! Far from finding such a change of career relaxing, a man who somehow managed to secure a genuine secretarial position would likely be in for a rude awakening. Even if he could cope with its very different demands, let alone found an arrangement that perfectly matched his fantasies, it's doubtful that it would prove satisfying for him in the long run, for the same reasons one wouldn't want to ride a roller coaster forever, as exciting as that might be to begin with. Sooner or later, the thrill would wear off, leaving the rider sick and tired of what should be an occasional pleasure. Nevertheless, the appeal is understandable - why wouldn't a man want to swap a stressful job for one where even the stresses are imagined to be exciting?

Making a secretarial scene feel real can add to the danger of a man confusing it with something more, especially if he is unhappy with his regular job. If you feel that this might be a problem for your husband, there are various ways that it can be addressed. You might, for instance, take advantage of being able to set him tasks in order to have him consider the less appealing aspects of working as an assistant, whether through direct experience, research or reflection. The reasons why he couldn't really be employed as a secretary offer further subjects for reports, which can be written as many times as may be required for him to get the message. As well as having him consider the differences between his daydreams and reality, or why you, the woman in charge, prefer a more temporary arrangement, you might instruct your husband to put himself in a real secretary's shoes, perhaps even an actual person's, and think about why such a subordinate might envy his position of greater responsibility. Alternatively, if his day job is genuinely getting him down, you might turn his secretarial persona to looking for practical ways it can be improved, from researching possibilities for career development to searching for more realistic alternatives.

For many men who want to be secretaries, the fun is concentrated at the start and end of a session - the former being where they dress up, and the latter where they relieve the resulting arousal. Rather than deny your husband either should he be too keen, you might reverse this order, requiring him to remain in women's clothing after climax - indeed, you might insist that he changes into his secretarial outfit only after it has lost its appeal, perhaps telling him that you want him to feel the same reluctance that women do when dressing for yet another disheartening day at work. Another approach is to give him too much of what he thinks he wants, extending his secretarial tasks well beyond the point of him being able to take any pleasure from them. Some men may be excited by the idea of having to toil away for longer than they would like, especially when aroused, but the reality of doing so soon becomes much less appealing. As such, you might propose a day, if not a weekend, in which your husband will work similar hours to a full-time secretary, with any breaks limited to those that he could expect in a real position. Like an actual secretary, he shouldn't expect to be the subject of your constant attention, instead only receiving enough to ensure that he remains focused on tasks deliberately chosen to be thankless, frustrating and tedious. Transcription is ideal for this, not only allowing you to set many hours work in a matter of seconds, but also to assess his efforts at a glance. Extrapolating your husband's expected output for the day from his first burst of enthusiasm is likely to set him a very punishing target!

Any reluctance on his part can be seized upon to make your point, it needing you only to observe that real secretaries have to work day in, day out without complaining, week after week after week. Such women generally don't get much say in what they have to do, certainly not being able to pick and choose if they want to keep their jobs! Because you're the boss, you're entitled to the final word about such matters - something that a sissy secretary can't protest too much about if he's to remain true to character. Indeed, it's possible to present such an approach as part of your games, even if you have other intentions, telling your husband that you need him to work overtime without warning. You might, however, be more forgiving than a real employer, allowing him to explain how what you're offering falls short of his full-time fantasies, or waiting until his face falls before informing him that the work you have in mind won't take more than an hour.

he's the secretary

Chapter 5: How can a sissy secretary be more realistic?

How can language deepen a man's sense of being a secretary?

What can I call my secretary?

What if he wants to become a secretary for real?

How real does it need to be?