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he's the secretary

Chapter 1: What is a sissy secretary?

Picture an executive sitting back at a big desk, watching as a secretary bends over a filing cabinet. Did you think of a female assistant? It would hardly be surprising if you did, with such employees to be found in many offices, even where another woman is in charge. Let's assume that the executive is a man, and humour his fantasies by having the secretary be suggestively dressed. It's easy to imagine a red-blooded boss indulging in unprofessional thoughts as his assistant's skirt stretches taut, as stereotypical as that is, but rather than wanting to have his way with her, his daydreams may involve them swapping places!

It might sound odd, but some men actually want to be secretaries, albeit of a stylised sort, whereas others can benefit from adopting such a role - not at work, let alone full-time, but temporarily, in the privacy of their own home! Indeed, the executive watching his assistant go about her business might be looking forward to wearing a skirt himself, perhaps having plans to spend his evening in a way that the woman fetching files would never want to - typing!

In this book, we'll explore how having your husband¹ play the part of a secretary can be surprisingly rewarding, not only for him, but also for yourself. We'll see that he needn't share our executive's desire to dress up in order to appreciate seemingly preposterous attire, with there being a wealth of advantages to him donning unlikely clothes regardless. Similarly, tasks that you might think a man would dismiss, whether because they are trivial or tedious, can take on a new light for him, even if he doesn't necessarily enjoy them at the time. In short, any man can benefit from becoming a secretary, but more importantly, so can the woman who becomes his boss - to such an extent that you might find yourself encouraging your husband to assume the persona of an assistant because of what it does for you!

^[1] For consistency, we'll refer to husbands and wives throughout this book, but you don't need to be married to a man for him to become your secretary.

What does it mean to be a secretary?

While male secretaries are not completely unheard of these days, working as an office assistant is not something that's considered to be very masculine. Rightly or wrongly, when people think of secretaries, they think of women, with the role having distinctly feminine connotations. The profession was not always female dominated, however - at the start of the twentieth century, taking care of a superior's affairs was a very respectable occupation for a man. Indeed, the word “secretary” shares the same roots as “secret”, reflecting the trust accorded to such a position. Even today, there remain traces of this in the word's other usage, which refers to a person who holds a particular authority. One would not look down on a Secretary General or a General Secretary because of his title, but these are not the sort of secretaries this book is about.

The societal factors leading to the profession of secretary becoming increasingly female are complex, but one might consider the introduction of the typewriter alongside greater, but still restricted opportunities for women. In any case, the days of men primarily holding such positions are long gone, with the vast majority of modern secretaries being female. That's a situation that hasn't changed over several decades, even if the work of a secretary has adapted to accommodate advances in technology, with computers replacing typewriters. Attitudes have also changed with the times, of course, such that women working in such roles often prefer to be referred to as administrators in order to distance themselves from old-fashioned stereotypes, but one doesn't need to look back too many years to find the reasons for such a reaction.

The 1950s might be regarded as the heyday of the traditional secretary, a time when the difference between men's and women's responsibilities was very clearly defined. The fifties secretary combined an impeccably feminine appearance with a steadfast devotion to a male superior, submissively accepting a subordinate position in which she provided support. Her duties saw her taking dictation, handling correspondence and maintaining files, while leaving the making of important decisions to the man she worked for. Her position was defined in terms of his, with the opportunities for promotion being extremely limited - managerial positions were considered to be for men, it being a woman's place to assist! Nevertheless, the stereotypical fifties secretary was expected to be happy about such an arrangement, not letting a word of complaint slip from her perfectly made-up lips, but instead always being eager to please.

Then as now, the work of a secretary might not have been regarded with the same respect as her manager's, let alone have received comparable remuneration, but it was nevertheless just as critical to the success of a company - just as it remains. Without what some might unwisely dismiss as pointless paper-pushing, the wheels of modern business would soon grind to a halt, with no amount of software capable of replacing a competent personal assistant. Such a woman performs similar functions to a male secretary from the century before, albeit in an electronic world, sparing her superior from having to worry about the minutiae of updating databases, scheduling video conferences and procuring purchases online. She is relied upon as much as her historical counterpart, needing to be able to take the initiative and think for herself rather than bother her boss about every little thing - indeed, she takes care of the little things for him.

That's a far cry from the stereotype of the sexy secretary that might feature in a man's fantasies, who isn't expected to do anything more intellectually challenging than choosing what colour to paint her nails. Not employed for her brains, this caricature of an office assistant instead satisfies her superior with her physical charms, asserting her suitability for the position in a short skirt and tight blouse. She might type a little, in so far as that's what her boss has in mind when instructing her to take dictation, but her professional responsibilities are otherwise likely to be limited to making the coffee for visitors and taking the minutes in meetings - as much so the man she reports to can show off what a trophy of a secretary he has as for any value in such work.

A real personal assistant would rightly take offence at being compared to such a parody, but the two nevertheless have things in common - not least that they both answer to their bosses, being expected to follow a superior's directions rather than leading themselves. As formidable as a businessman's secretary may be to outsiders making claims on his time, she is nevertheless deferential to him, even though her submission manifests itself very differently to the fantasy figure bending over a filing cabinet. Furthermore, both sorts of secretary wear an unwritten uniform, having an undeniable smartness even when their workplace attire doesn't take the form of the traditional skirt and blouse. A female office worker might not dwell on her outfit as she dresses for another day at her desk, but it speaks of her occupation all the same. Conversely, while a man's fantasies might have a sexy secretary leave little to the imagination with a provocative choice of clothes, those nevertheless retain professional vestiges, it being possible to segue from one to the other without such garments ceasing to be a secretary's.

We might summarise both secretarial stereotypes as not only being feminine, but also submissive, differentiating them from other such roles by means of the tasks that are performed in the service of a superior, as well as the clothes that are worn. Considering another archetype that men often entertain fantasies about, it is easy to see what makes a secretary a secretary rather than a maid, even though both take care of matters that others might regard as beneath them, without being expected, or indeed permitted, to make decisions beyond how best to complete the work they have been instructed to do. Secretaries do not wear aprons or scrub floors, any more than maids dress for the office or type. While neither a professional cleaner nor an office administrator is likely to appreciate being reduced to a caricature, the associated stereotypes still have power, especially when putting together a persona with the aim of affecting a man.

Figure 1.1: Although each is different, these stylised images of secretaries nevertheless share common themes. Whether an old-fashioned secretary updating a ledger in pen, a fifties secretary typing a letter, or a modern secretary working on a computer, all are unmistakably secretaries - as, indeed, is the suggestive caricature that might feature in a man's fantasies as she bends over a filing cabinet.

Why are men attracted to the secretarial archetype?

On first consideration, one might dismiss the appeal of the secretary as being no different to that of any other sexually charged stereotype, it hardly being surprising that men's fantasies might feature a woman who is not only suggestively dressed, but also submissively eager to please. If one reflected further, one might wonder whether the blurring of professional and pornographic didn't have a certain taboo thrill, with the unbalanced power dynamic adding excitement to the idea of having sex at work - a location ordinarily off-limits to intimate activity. In that context, the stylised clothes of a sexy secretary might be seen as little more than a means of titillating the male imagination while remaining in keeping with an office setting, in a way that picturing a woman working naked wouldn't. Similarly, stereotypical tasks such as typing could be considered as evoking a mood, if not a pretext for having a submissive assistant invite attention by putting her in a provocative position - after all, why else would a secretary be bending over a filing cabinet, unless she secretly wanted her boss to tell her to take off her tight skirt?

A more modestly dressed woman might nevertheless become the subject of a man's sexual fantasises in lieu of there being anything more explicit to distract him in a dull meeting - indeed, the ordinariness of her attire might have an odd allure of its own. Garments that women take for granted can be fascinating for men, thanks to their feminine connotations, even without the wearer going out of her way to spice things up! A satin blouse might captivate a man with how its shiny material catches the light, whereas sheerer fabric might distract him from his work by offering tantalising hints at whatever may lie beneath, both capable of emphasising the female figure with a fitted cut even if they aren't unbuttoned suggestively. Crossdressers are especially susceptible to women's clothes, being attracted to blouses and skirts, bras and stockings because of the physical as well as the psychological effects of such garments, which are very different to men's regular clothing. From a male perspective, a secretarial outfit presents a wealth of unfamiliar delights in a ready-made package, made more thrilling by the thought that women wear such clothes to work day in, day out - so often, in fact, for them to become blasé about the likes of hosiery and heels, which are so unlike men's socks and shoes.

It would be foolish to think that the appeal of the secretary is solely about appearances, however, any more than it is merely a matter of sexual arousal, as powerful as these aspects may be. The archetype embodies a submissiveness that is in stark contrast to the battle for dominance that many men must contend with on a daily basis, seemingly unburdened by any need to make difficult decisions. A businessman watching a secretary bending over a filing cabinet might romanticise a role that lacks the challenges of his own, dismissing the different demands of her position as he dreams about taking a break from the dog-eat-dog rat race. How wonderful it would be to have to worry about nothing more than where to find a file, he might think, drawn to the idea of being able to swap his stressful responsibilities for something so straightforward! Being told what to do is appealing because his imagination still allows him to have the final say, unlike the actual secretary scurrying around to satisfy him.

Thanks to its associations with submissive, if not sexily dressed, secretaries, typing might seem exciting for a man who doesn't have to do much of it himself, but the thought of having to tackle thankless, tedious tasks can be thrilling in a different way. Some men have masochistic desires that see them craving humiliation or degradation, whereas others have feelings of guilt or shame that they seek to assuage through humbling themselves - not least crossdressers who have yet to fully come to terms with wanting to wear women's clothing. The humdrum work of a secretary offers plenty of scope for these men to imagine themselves doing things that they would ordinarily consider beneath them, with feelings of embarrassment and emasculation combining with those of futility and frustration that are engendered by pointless or punitive work. Just as one might watch a scary horror movie or ride a roller coaster to explore what would otherwise be overwhelming emotions in a safe environment, so too might a man daydream about being a downtrodden secretary doomed to endless days of mindless, monotonous drudgery. He might develop such a fantasy with thoughts of having to work for an impossible to please boss, savouring the different power dynamic in a way that neither he, nor the woman whose shoes he puts himself in, would enjoy for real.

Again, the same themes are apparent, however stylised, with the attraction of the secretarial archetype stemming not only from its submissive femininity, but also the associated clothing and tasks. Some men may find one aspect especially appealing, whereas others may be drawn to the unique combination presented by office assistants in the abstract, separate to any actual individual. Moreover, the appeal need not necessarily be external, as would be the case were a man to daydream about possessing a status symbol such as a flash car. Admittedly, many men's fantasises might feature having a sexy secretary as a subordinate, but others are different - not wanting to have her, but to have what she has, even if that's something that an actual secretary would welcome being without!

How is a sissy secretary different to a real one?

Even if a man's daydreams have little basis in reality, the caricature that features in them is a powerful one. An assistant wanting to inveigle her boss might deliberately employ aspects of the secretarial archetype to her advantage - for example, by choosing clothing that plays to it, or assuming an exaggerated persona while at work, albeit not needing to go so far as bending over a filing cabinet to have an effect! So too might a woman wanting to help her husband unwind when he comes home, perhaps with bedroom games featuring a stylised interpretation of a secretary far more provocative than any to be found in the office. She isn't the only one who can take on such a character behind closed doors, however, even though few men would want the alternative to be known by their colleagues - that it is he who becomes the secretary, in so far as portraying a parody can ever make him one, adopting particular attitudes, attire and activities in order to bring about a different state of mind.

Becoming a secretary might mean nothing more than a man donning a symbolic outfit in advance of seeking gratification, whether by himself or as part of a role-play in which his wife becomes the boss. His clothes may simply reflect his change of character, or may be carefully chosen to provoke particular feelings - not only arousal, but also emasculation or even embarrassment. Alongside what he wears, a man wanting to play the part of a secretary might undertake tasks that are traditionally associated with the role, such as typing or taking dictation. Again, these might merely be symbolic, perhaps helping to set the mood prior to sex, but they may also be purposeful in their own right, even if that purpose is just to induce a sense of frustration or powerlessness. If a man wants to feel humbled or humiliated, such tasks might go well beyond what could reasonably be asked of an office assistant, having shameful or suggestive aspects, if not being more akin to punishments. Alternatively, they might be overly simple and repetitive, with their mindlessness sparing him from having to think.

Rather than deciding such matters himself, a would-be secretary might seek to cede control to someone else, right down to the smallest detail. The appeal of an unwritten uniform can be seen in this light, especially if particular garments are prescribed. In the absence of a superior telling him exactly what he should type, a man wanting to feel like a secretary might be attracted to exercises with clear, unambiguous instructions, although not necessarily with the aim of completing them successfully! Some men might set themselves up to be scolded for mistakes that they couldn't avoid, yet might nevertheless deliberately make, relishing the disgrace of being disciplined. Others work in the hope of receiving another's praise, or else crave the satisfaction that comes from having achieved something, however meaningless it may be in the grand scheme of things. What they wear and do is merely a means of engendering such emotions, although a man might take advantage of uncomfortable clothing or tedious tasks in order to lose himself in their immediate challenges.

Regardless of the exact details, it's fair to say that this is a rather unrealistic representation of a secretary, being as different from those whose unsung efforts keep offices running smoothly as the latter are from the pin-up parodies that spend their working hours bending over filing cabinets. To aid this distinction, we might refer to what a man becomes when he dons a skirt and blouse to do a little typing as a “sissy secretary”, using the word “sissy” as a convenient shorthand for “submissive crossdresser” rather than as a term of disparagement. Although all three sorts of secretary share the various themes that we considered earlier - femininity, submission to a superior, customary clothing and tasks - they do so only broadly. Each has their own place - no company would want to hire a secretary whose thoughts of work go no further than dressing up for selfish satisfaction, any more than a man's fantasises are likely to feature an office administrator proficient at juggling multiple tasks, or a professionally trained personal assistant would apply for a pornographic role.

A company might employ several different types of secretaries, ranging from those working as part of a team in its human resources department, through to personal assistants reporting to individual executives. While all could rightly say that they were secretaries, even the temp hired for a day to attend to a backlog of filing, their work is far from interchangeable, as one would soon discover were one to ask the temp to swap places with a senior human resources administrator! Similarly, sissy secretaries also vary widely, depending on the aims that they, or their wives, hope to achieve and the aspects of the stereotype that they choose to emphasise to that end. Admittedly, there are men who dress up for their own sexual satisfaction, but there are others who do so for very different reasons. Let's consider some examples that occur in loving relationships:

• the sexy game

  David is only knocking on the door of the lounge, but as he waits for his wife's permission to enter, it feels like the room beyond is his boss's office. He's dressed as a sexy parody of a secretary, but his tight skirt and panties do as much to hold his desires back as they do to inflame them. Soon he's standing in front of where his wife is sitting, acknowledging her authority by submissively asking what he can do for her. His manhood remains suppressed as he drops to his knees, it being his tongue that the woman in charge requires - at least, to start with! She won't be alone in enjoying his devotions, however, with this game proving intensely erotic for him even if she doesn't want more!

• making things right

  John has lost track of how many lines he's typed, but he can't stop to consider the matter when the computer is so demanding. Every repetition reminds him of what he's done to disappoint his wife, with an uncomfortable bra and blouse adding to his sense of disgrace as he seeks to make amends by means of a stylised punishment. “I must not come home late from work”, he begins yet again, knowing he has to get every letter right if the line is to count, “or I will be spending even longer working as a secretary”. At least when he's finished, he can be sure that his wife will forgive him, not that she needs to impose such discipline as often these days - as much as he might hate typing lines, he has become much more considerate of her feelings as a result!

• sensible crossdressing

  Richard's crossdressing has changed since he became his wife's secretary, but he can still enjoy wearing women's clothing even though he now does so on her terms. That sees him thinking about the purpose of each garment as he puts together an outfit professional enough that he could almost wear it to work, dressing to impress rather than simply to indulge his desires. After donning a combination of underwear and outerwear that allows him to feel feminine while remaining in keeping with his secretarial persona, he sits down with his laptop - not to look at degrading pornography, as he used to, but rather to research fashions for the report that he's writing. Even if his wife doesn't let him buy any of his suggestions, the exercise will add to his knowledge of what women wear, with what was once his sordid secret now being something they can share!

• doing his accounts

  James often found it difficult to keep his accounts up-to-date, leading to trouble when bills weren't paid on time - until his wife suggested he dressed as a secretary! He wouldn't have thought that changing his clothes would make such a difference, but after overcoming his initial reluctance, he discovered how doing so puts him in the right frame of mind for ploughing through tedious paperwork. Once a week, he swaps his shirt and trousers for a skirt and blouse, sitting down at his desk and dealing with whatever may be outstanding. He no longer looks for ways of putting things off, now seeing distractions as only delaying the satisfaction that comes from having his finances sorted. Rather than forever rowing with his wife about money, his regular secretarial sessions mean that he can surprise her by finding savings that can be spent on treats!

All of these men could be described as sissy secretaries, as, indeed, could many more, but no two are the same. As with the other secretaries that we have been considering, they share certain aspects, but even the clothes they wear vary immensely - some chosen to arouse, others to subdue. So too their motivations for becoming a secretary, let alone the precise details of what they do. Adopting such a role might not be only a sexy game, a ritual punishment, an approved way of crossdressing, or a shortcut to mental discipline, but could actually be several of those - either in combination or on separate occasions. Moreover, as some of the examples above illustrate, a man might become a secretary not for himself, or at least, not wholly, but rather at the behest of his wife.

Why might I have my husband work as a sissy secretary?

If you've never considered the idea of men becoming secretaries before, it might seem strange to think of your husband wanting to do so, and even stranger to imagine that you might encourage him if he weren't already keen! In fact, there are many reasons why such an arrangement can work to your benefit as much as his, although the two are often connected - after all, the trite saying “happy spouse, happy house” works both ways! Depending on what you are looking to achieve, you might have your husband become your secretary:

• to get him to do what he needs to do without nagging

  Does your husband put off particular tasks, even after you point out the consequences of not completing them on time? If you're tired of him leaving things to the last minute, schedule them for when he's a secretary! A change of role provides both the motivation and the mindset that a man needs to tackle his tax return or find more competitive insurance cover, to name but two of the countless tasks that are ideally suited to a sissy secretary. Once your husband is dressed the part, you won't need to nag him about his procrastination, with it seeming perfectly natural for him to fill in forms so that he can get them approved by his boss - you! Even if he doesn't particularly enjoy sitting down with such paperwork, he'll certainly be glad to have ticked off tedious, yet necessary tasks from his to-do list, without you hounding him about them!

• to put distance between him and his other responsibilities

  Some men have difficulty leaving their work in the office, with their job encroaching on their thoughts, if not their time, even when they're not on the clock. So too with many hobbies, which can become unhealthy obsessions if your husband is unable to set sensible limits. Rather than feeling as though you're a distant second to such distractions, you might use the very different demands of being a sissy secretary to draw a clear line between what your husband was doing before and what might come afterwards. He'll find it hard to dwell on the past or worry about the future when his role requires him to focus on the present, with the immediacy of its challenges encouraging him to put everything else to the back of his mind. You won't be alone in appreciating the effect, however, with your husband sure to feel the benefits as well, thanks to a change being as good as a break.

• to allow him to make amends

  Your husband won't want to stay late at work when he knows that not coming home on time will see him having to spend still more of his evening working for you! A punitive task will not only deter him from letting you down again, but also offers a way for him to make things up for having done so, such that you might have your husband become a sissy secretary to say sorry! Simply filling in a form to apply for forgiveness can have a surprising effect on a man's attitude, let alone writing a longer report, requiring him to reflect on how he's disappointed you in as much detail as you deem necessary. Alternatively, you can have him learn his lesson by typing lines, seeing him having to acknowledge what he's done wrong again and again. Add some challenging clothing to the mix, and you've got a form of discipline that can be made to fit the crime with very little effort on your part, no matter how long it might occupy him! Once again, however, he'll benefit too, because of how doing so clears the air.

• to give him insight into a different perspective

  As we touched on earlier, many men have an unrealistic understanding of what's involved in being a secretary, taking the women they work with for granted even when they don't make them the subject of inappropriate daydreams. Having your husband adopt such a role himself presents a range of opportunities for him to consider matters he might otherwise never have given much thought, whether you playfully treat him like the sort of sex object he might see an attractive assistant as, or have him take his secretarial work far more seriously! He'll be less dismissive of women's difficulties dressing when he's had to worry about his own stockings and bra, whereas being expected to satisfy impossible demands will discourage him from making similar himself, quite apart from the effects of research projects that focus on related subjects! Spending some time as a sissy secretary won't just affect how your husband regards office assistants, however, but will give him a greater appreciation of your own perspective as well, with his increased awareness of your concerns sure to benefit your relationship.

• to encourage him to focus on your needs

  Men who are used to taking charge at work can forget their wives have needs too, especially when the desire to get their own way comes home with them. Your husband will find it hard to be too self-centred when he's a sissy secretary, however, with the submissive associations of such a role making it natural for him to defer to your decisions. Having him become your secretary in advance of a discussion shifts the balance in your favour from the start, assuming you don't simply want your husband to listen to what you have to say. Even laying down the law becomes easier, both for you and for him, when his subordinate status makes it clear that you're the boss - without you needing to go out of your way to play that part! Whether there are mundane matters that you'd like him to attend to, or more intimate needs you want addressing, your husband will instinctively want to please you when he adopts a secretarial persona, thanks to the stereotype encouraging selflessness, consideration and submission.

• to add excitement to your love life

  Many couples love to liven things up in the bedroom, if not beyond, with a little erotic role-play. The complementary roles of secretary and boss have plenty of sexual charge if you're feeling frisky, with the naughtiness of reversing them adding to the thrill of such games. It doesn't take much to create a provocative scene where your husband becomes your personal assistant, with the suggestive connotations of the sexy secretary offering a wealth of ways to get him worked up - while still putting your pleasure first! Indeed, the associated attire provides a means to keep the more demanding aspects of his manhood in check until you're ready, yet simultaneously provokes passions that you can both enjoy. Being the boss lets you take the lead, but you can just as easily lie back and leave taking care of the details to him, knowing that your respective roles allow you to have the final say about what he does.

• to provide a controlled outlet for crossdressing

  Crossdressers have an undeniable fascination with women's clothing, but their desire to dress up often dwarfs their ability to put together plausible outfits, let alone look presentable! If you're looking to temper your husband's fondness for ridiculous dresses, or want to teach him that a woman's wardrobe consists of more than just frilly lingerie, then the unwritten uniform of a secretary offers a practical alternative while still being capable of scratching his itch. Regardless of whether you expect him to look perfectly professional, or permit a little sexiness in what he wears, having him become a sissy secretary helps put his crossdressing on your terms. As well as setting standards for his clothing, the role also encourages activities that are far more positive than the self-gratification that crossdressers often indulge in, giving his penchant for women's things an unexpectedly productive silver lining!

• for fun!

  Life is too short to take everything seriously! Although few people ever look back and wish that they'd spent more time at the office, playing the part of a boss or secretary in private can be a very different story. No matter how old you or your husband may be, fooling around with a pretend situation can help both of you feel younger, with preposterousness only adding to the fun! Having your husband do as you dictate while he's dressed in daft clothes might sound silly, but sometimes silliness is exactly what you need in order to have a good laugh! Seemingly dull things can be surprisingly entertaining when approached in the right way - even something as boring as typing has the potential for endless amusement if you decide to make a game out of it.

Again, not all of those might apply, let alone at the same time - you might have your husband become a sissy secretary for one reason on one occasion, yet quite a different one on another. Just as a man drawn to the archetype might emphasise particular aspects for particular purposes, so too can you, albeit not necessarily in the same way! There's certainly no need to follow a prescribed path - from the things that your husband might do as a sissy secretary to the clothes that he might wear while doing them, everything is optional, as the prevalence of words like “might” throughout this book hopefully makes clear. With that in mind, the suggestions presented in the following chapters are intended as possibilities that you can pick and choose from, it being entirely up to you which you try!

What are some common misconceptions about sissy secretaries?

Regardless of which of you or your husband is more interested in him being a sissy secretary, you might have concerns about exploring the idea. Although it doesn't take much to dip a toe in the water, you might nevertheless be worried about where things might go or what that might mean, assuming you can even get started - after all, your husband might have concerns about doing something a bit different too! It's not uncommon for people to harbour misconceptions about male submission or crossdressing - indeed, even submissive crossdressers can misunderstand their desires, struggling to explain what drives them even to themselves without getting caught up in unrealistic fantasies. Fortunately, a little reflection is usually enough to dispel any false impressions. Let's consider some reasons why you might be hesitant about having your husband become a sissy secretary:

• it has to involve crossdressing

  Stylised clothing is a significant enough component of the secretarial archetype as to warrant a whole chapter of this book, but there's actually no need for your husband to wear the stereotypical skirt and blouse if that really doesn't appeal - as we'll see in due course, a shirt and tie can suffice, it being possible for him to become your secretary in the sort of outfit that a man might wear to the office. Of course, a more conspicuous change of clothing will have a more profound effect on his state of mind, with your husband not needing to be a crossdresser to be affected by feminine garments - indeed, having no desire to dress up can make doing so all the more significant for a man. If you're worried that he'll look daft as a sissy secretary, rest assured that it doesn't matter if he isn't convincing - after all, no-one is going to see him other than you, regardless of whether he's attractive, amusing or simply absurd! It's not so much what he wears as why, with the purpose of a secretarial outfit being to make your husband feel a particular way.

• it has to involve sex

  Talk of sexy secretaries wearing provocative clothing while they undertake suggestive, if not explicit, activities might leave you thinking that having your husband become a sissy secretary must involve sex, but these aspects are entirely optional. A modest outfit can affect a man just as much as one that's more arousing, albeit in a different way, with unremarkable, yet undeniably female garments having an effect even on non-crossdressers - as can easily be demonstrated should you suggest that your husband wear a random skirt to work! Similarly, stylised secretarial tasks can be tailored to elicit a variety of non-sexual emotions, as our earlier examples involving typing lines and tallying accounts illustrate. It's true that some men are excited by feelings of embarrassment or emasculation, but there's no obligation for you to act on these if that's the case with your husband - indeed, as we will discuss in a later chapter, there are ways of ensuring that he doesn't do so either, keeping your secretary chaste until he changes!

• it's a career

  If a woman were to say that she wanted to become a secretary, the implication would be that she was considering a change of career, which can make it concerning if your husband expresses similar sentiments. That's not what we're proposing in this book, however, even though some men might flirt with far-fetched fantasies involving quitting their jobs so that they can work as submissive assistants full-time, for reasons that we will look at in a later chapter. Instead, becoming a sissy secretary is entirely separate to whatever your husband might do for a living, being better considered as an occasional pastime or hobby rather than any sort of profession! Far from occupying a man from nine to five, a secretarial session needn't last even an hour if you don't want it to, nor do such sessions have to occur with any frequency - certainly not every day, week in, week out, as would be the case for a real secretary!

• it's sexist

  Gone are the days when men's and women's roles in the office were as distinct as the stereotypes that we're drawing upon - men in charge, women only there to assist. You might worry that by having your husband wear a skirt and blouse to perform dull or demeaning work, you're encouraging him to see anyone who wears or does similar as inferior, reinforcing attitudes that women have worked so hard to break free of. In fact, the reverse is true, with the challenges of seemingly simple tasks giving a man a greater respect for the work of assistants once he's faced them himself. Moreover, the stereotypical secretary's outfit could be worn by a commanding businesswoman without any loss of authority, it not being a skirt and blouse that signifies submission, but rather their effect on the wearer. The very same garments can make a woman feel confident in her femininity, yet leave a man feeling weak - either as a result of how she's empowered by them, or because of the way that they emasculate him.

• it's too demanding

  If you're not used to being the boss, telling your husband what to do might seem difficult, all the more so if you're not familiar with secretarial work yourself. Rather than requiring you to spell everything out, however, the subordinate nature of the role means that you can leave many of the details to him, even if he's equally in the dark about what sissy secretaries might do or wear. You don't need to do anything more than ask questions to get started, it being your secretary's responsibility to provide possible answers for you to pick from - which you might do at random, discovering what works as you go! Furthermore, it only takes a few moments to set a task that can keep a sissy secretary occupied for hours, with many of the activities that we'll be discussing ones that a man can undertake by himself, without any special abilities. He doesn't need to be a proficient typist to do so, however - in fact, setting a sissy secretary a typing task can be far more fun if he isn't - although he may become one over time!

• it isn't something he would want to do

  Some men are very enthusiastic about becoming secretaries - indeed, you might be reading this book at the behest of your husband. Others are not, such that you might wonder whether he won't baulk at any suggestion of crossdressing or submission, especially if he's a particularly macho man. You might, however, be surprised to find that your husband welcomes the opportunity to explore a less assertive persona temporarily, or else that he appreciates the other benefits that we've been discussing - something that neither of you will know until you try. Even if dressing up and playing the part of a secretary has no intrinsic appeal for him, he might nevertheless regard it as a means to an end, whether that's achieving things that he finds difficult, making amends in a clear and unambiguous way, or simply being silly and having a laugh with someone that he loves. Rather than making assumptions about your husband, or indeed, allowing him to make assumptions himself, why not see how such things work for real?

• it'll lead to other things

  If you search for sissy secretaries, you'll find all manner of odd material, often of a pornographic nature, if not featuring distasteful themes. Sadly, this isn't a phenomenon that's restricted to the subject of men becoming secretaries, nor even crossdressing and submission, with similar to be found for almost any area you might care to consider. That's because the Internet allows people to explore desires that they may not be able to satisfy in other ways, with these combining with other, entirely separate, aspects of their lives. To demonstrate this point, you might search for men wearing trousers, which yields pictures of suggestively posed hunks and leather enthusiasts alongside more conventional models, albeit with neither being representative of the average trouser wearer. Just as there is a range of interests among real secretaries, and indeed, any other group of people, so too is there among sissy secretaries, but the particular inclinations or tendencies of one individual have no bearing on those of another - nor need they affect what you and your husband do.

Where do we go from here?

In this chapter, we've explored the concept of the sissy secretary, showing how it draws upon other secretarial archetypes, yet remains distinct from them, in a similar way to how the unlikely caricature of the sexy secretary is different to those women who actually do administrative work. We've seen why some men are attracted to the idea of becoming secretaries, and considered the benefits of them adopting such a persona - not only for themselves, but also for their wives. In doing so, we've touched upon the effects of stylised clothing and tasks, albeit broadly, suggesting how these can be used to encourage certain states of mind.

We'll discuss clothing and tasks in more detail over the course of the next two chapters, first looking at what you might have your husband wear in order to make him feel like a secretary, then considering what he might do as one. Both chapters will explore their respective subjects with a variety of possible aims in mind, presenting options from playful to punitive without becoming unduly unprofessional. After that, we'll examine more explicit matters, with chapter four discussing the subjects of sex and physical punishment - not activities that occur in real offices, yet capable of adding plenty of spice to a secretarial session! In the final chapter, we'll look at other ways you might deepen your husband's sense of being a secretary, exploring the effects of language and other little details before concluding with what to do if he wants to take things further.

Each chapter seeks to be comprehensive, but there's no need to pore over every word, let alone act upon it all - simply skimming the sections will give you a feel for their contents, allowing you to return as and when you might want to consider a subject in more detail. Even then, the intention of this book is to provide possibilities that you can pick and choose from, suggesting ideas that you might consider trying. If something works for you and your husband, then keep it, but if not, move on - you'll find plenty of other options in the following pages!