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:

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:

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:

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!