he's the secretary

Chapter 2: What can a sissy secretary wear?

Clothes make the man, as an old proverb says. A moment's thought will confirm its truth - one need only consider why a businessman wears a smart suit and tie rather than a scruffy T-shirt and shorts when seeking to impress clients. His choice of clothing doesn't just affect how other people see him, but has an effect on his confidence too, making him feel as well as look the part - or not, depending on how well it fits both him and the situation. No matter how expensive or stylish his suit might be, it's no good if it's too baggy or too tight, nor would an overly formal outfit serve him well at the beach. Indeed, identical garments can affect different wearers in different ways, as becomes obvious if we imagine a businessman's secretary lending him her clothes. No-one might give much thought to her wearing an unremarkable skirt and blouse to the office, but the same couldn't be said about her boss were he to do the same!

With that in mind, it's easy to see how you might put together an outfit that will affect your husband, it needing no more than a few garments with suitable connotations. These might merely be the same ones he wears to work, having meaning for being worn at home, or may be reserved solely for when you want him to feel like a secretary. In this second category can be placed clothes that men do not ordinarily wear - not just skirts and blouses, but the likes of stockings and bras as well. Such garments are readily available at modest cost, even in men's sizes, with the conspicuous difference between them and your husband's regular attire not one that is likely to be lost on him!

Whatever you choose, the unwritten uniform of a secretary will make it clear exactly when you want your husband to adopt such a role, it only needing him to change into it to feel the associated expectations. Of equal significance, the reverse is also true, with the normal state of affairs being restored as soon as he changes back. The greater the difference in between, the more profound the effect, with the stereotypes we discussed in the previous chapter lending their power regardless of the reasons for him becoming a secretary. Although we'll discuss options in detail in this chapter, don't think that having him dress the part must be a monumental challenge - a single symbolic garment can have a surprising impact. Moreover, unless you wish to make a game of it, even the most elaborate of outfits needn't take your husband very long to put on or take off, allowing him to devote the bulk of his time as a secretary to whatever you want him to do - albeit with his clothing affecting him while he does!

What clothes are best for a sissy secretary?

Picture a fitted blouse with a revealingly low neckline, cut from eye-catching hot pink satin. If you were asked whether you could wear such a garment, you would consider not only its size, but also the suitability of its style, colour and fabric, taking into account where you would be wearing it. You would want to feel comfortable, not only physically, but also psychologically, especially if you were choosing something to wear for work. You'd likely reject a blouse that restricted your movements, just as you would one that attracted too much attention, let alone made you look ridiculous, either because of how badly it fitted, or as a result of it being unprofessional. Depending on the circumstances, you might prefer a blouse that didn't distract you any more than it did those around you, or alternatively, one that boosted your confidence.

All that is turned on its head when choosing women's clothes for a man to wear in order to affect his state of mind. Whereas he might think little of wearing a blouse that was indistinguishable from one of his shirts, the deliberately exaggerated style of our example is sure to have far more of an effect! For starters, there's the fact that it wouldn't flatter a masculine figure, instead emphasising how the male body differs from that of the intended wearer - proportionally bigger in some places, yet smaller in others, simultaneously making such a blouse both too tight and too loose for him. Then there's the striking colour and fabric, with the combination not one that many men could model without feeling self-conscious, thanks to its unmanliness. A crossdresser might choose it for that very reason, but regardless of whether or not a man enjoys wearing women's clothes, the blouse is both physically and psychologically imposing, being quite unlike anything he would ordinarily wear.

While it isn't necessary to go to such extremes, the provocative blouse illustrates three general principles when picking garments to help your husband feel like a secretary. Firstly, it is better for them to be different to those he might wear as a man, having power because of their unfamiliarity. Ideally, there would be no male equivalent that he could relate them to, as is the case with skirts and bras. Secondly, such garments should be feminine, whether in their purpose, connotations or style. Again, skirts and bras fit the bill, but so too would sheer stockings or lacy panties, even though these might be compared to men's socks and briefs respectively. Finally, clothes for sissy secretaries benefit from being annoying, restrictive or inconvenient, thus requiring the wearer to regularly acknowledge their presence, and consequently, their meaning. Here, we might consider a skirt restrictive enough as to require a man to shuffle rather than stride, or a bra that burdens him with a wobbling weight.

Matters of fit are of much less concern, beyond the fact that your husband must be able to get into whatever he wears. Moreover, there's no need for him to look convincing as a woman, it being enough for his clothing to convey the general impression of a secretary, even if only a caricature of one. Indeed, implausible or ill-fitting garments might be considered advantageous because of how they heighten a man's awareness of them! That means that you don't have to go to great trouble when putting together an outfit for your husband, but can simply pick clothes that catch your eye, assuming that you don't simply leave the choice to him. Even if he knows nothing about what women wear, he can't really go wrong if the aim is merely to make him feel different, with any mistakes offering an opportunity for him to learn. Although we'll shortly be discussing individual garments in detail, this is more to give you a feeling for possibilities than to suggest that you must worry about every last point, so don't be daunted - dressing him as a secretary is easier than you think!

Shirts and ties

It may seem strange to start by suggesting that your husband doesn't need to wear anything out of the ordinary to become a secretary, but a smart shirt and tie is quite sufficient should having him dress as a woman not appeal. Garments that wouldn't warrant a second glance in the office can nevertheless have great significance when worn at home, with men's business attire having connotations of its own. There's a reason why men want to loosen their collars when they leave work, which can be reversed to your advantage by requiring your husband to present himself professionally for your games. That may mean a buttoned-up suit jacket in addition to crisply pressed trousers and polished shoes, making him feel as though he were attending an important interview or presentation.

A necktie is a surprisingly powerful garment in its own right, capable of acting as an impromptu leash should you want to tell your husband where you want him in no uncertain terms. To stress his submission, you can explicitly refer to his tie as such, even if you don't do anything more than make a fuss of straightening it - something that can be done perfectly respectably in public, no matter how embarrassed it may make him feel. Behind closed doors, you can use a tie-cum-leash to lead a man from one room to another, to direct his attention to particular parts of your body, or to make him bow his head while you speak to him. Almost any necktie is suitable for this purpose, but sending him to work in a pink satin one will make it hard for him to forget what he's coming home to, regardless of whether he wears matching underwear!

Women don't wear ties the same way that men do, but that doesn't mean you can't make one part of a more feminine secretarial outfit. Rather than swap his shirt for a blouse, however, you might want to swap it for no top at all, having your husband wear only a tie around his neck. Few self-respecting men would want to be seen at the office with a bare chest, but your personal assistant may be more eager to strip off in the bedroom. To encourage him to take things slowly, you can insist that he keep his trousers on for foreplay, whereas conversely, you might engender a sense of embarrassment by having him shed them for more mundane activities. Even if you allow him to retain his underwear, your husband will be conscious of what he isn't wearing should he have to sit and type lines with bare legs, let alone if he must complete a punitive task all but naked.


Drawing a line between what strictly counts as a blouse and what should be called a shirt can be difficult when it comes to women's clothing, but it's much easier to separate either from garments meant for men. Rather than get bogged down in the minutiae of fashion, for the purposes of this discussion, we'll refer to what women wear as blouses, and what men normally wear as shirts. The two aren't completely different, however - except in the most relaxed of offices, or perhaps on dress-down days, both men and women are expected to dress reasonably formally for work, with shirts and blouses reflecting this. That sees both being smart, buttoned-up affairs with collars, often limited to plain, conservative colours if not the traditional white, crisp and clean, but never creased or crumpled!

Obviously, women's blouses and men's shirts will differ in how they're cut, because men have broader shoulders, whereas women have proportionally larger busts and hips. Even this difference is enough to make a statement when challenged, as a woman wearing an oversized boyfriend shirt demonstrates, its bagginess having a lazy allure that's a little too casual for the office. Yet a man doesn't need to squeeze himself into something that doesn't fit him in order to be affected by the associations of a blouse, as you'll see if you refer to one of your husband's regular shirts as such - the word itself offers a way of making him feel like a secretary, without him having to wear anything that he wouldn't feel comfortable being seen in at work. Indeed, in some countries, a man's masculinity may be challenged by calling him “a big girl's blouse”, a phrase which is synonymous with “sissy” in the latter's disparaging sense, highlighting how blouses are undeniably feminine.

Even a blouse that might be mistaken for a shirt presents difficulties for the male wearer, thanks to how its buttons are placed on the side opposite to the one he is familiar with. The need for a man's fingers to perform the mirror image of their usual movements will require him to think about what he's doing whenever he fastens or unfastens a blouse, stressing the difference between it and what he ordinarily wears. Of course, many blouses show that they are meant for women in less subtle ways, being tailored to a female figure. It's natural for a man's eyes to be drawn to a fitted blouse when its cut emphasises the wearer's curves, but such a garment is no less commanding when he must consider how it doesn't fit his own body! We'll discuss ways of addressing this in due course, but without padding and cinching, a fitted blouse is likely to be both too tight and too loose, thus proving distracting for a man to wear.

Ask a man to describe a sexy blouse, and he's likely to propose one that shows a suggestive amount of skin, whether as a result of having a provocative number of undone buttons, or because its low-cut neckline means it's incapable of covering any more! The allure of the female cleavage hardly needs explaining, but your husband is unlikely to find a plunging blouse as pleasing should he have to wear one himself. There can be no doubt about the unmanliness of such a style, which is sure to make a mockery of his chest regardless of what it might reveal beneath! Nor is this the only way that a skimpy blouse can induce a sense of vulnerability in the male wearer, with a sleeveless design also capable of making a man feel inadequately dressed, even though many women might happily wear the same to work in warmer weather. Fewer would consider a blouse that was cropped or tied beneath the bust to reveal the midriff, such styles being reserved for men's fantasies, but a sissy secretary can wear them nevertheless.

Instead of skimping on material, however, you might prefer to have your husband wear a blouse with more fabric - not only to help conceal any contrivances that might be shaping his body, but also to impart further femininity. Men's shirts generally don't have flounces or frills, with such embellishments sure to make a statement. Whether it has a ruffle that runs down the length of the placket, or a pussy bow around the neck, a fussy blouse will bring to mind a similarly fussy secretary, imposing expectations on the male wearer. Long, loose sleeves can be pleasingly inconvenient, even before one considers the problems of fitted cuffs with multiple fiddly buttons, but short, puffy sleeves can be just as effective when it comes to emasculating a man. Even small details are capable of turning a simple shirt into one that no businessman would want to wear - consider the effect of a Peter Pan collar, perhaps trimmed with lace or tied with a ribbon.

The choice of fabrics can also have a big impact on the wearer. While a man might get away with wearing a pale pink shirt to work, this traditionally feminine colour nevertheless has unmanly connotations which can be drawn on when turning your husband into a secretary. White, of course, is the staple when it comes to office wear, but even if you limit your husband's blouses to this colour, you can still pick materials to elicit a particular effect. An otherwise modest garment will catch the eye if its material is sheer enough to show the outline of a bra beneath - indeed, as we'll consider shortly, the latter's presence may be betrayed by the sort of thin white shirt that a man wouldn't normally give a second thought. A sheer lace or mesh blouse takes this idea a step further, whether in white, pink or even black, with its feminine filigree literally leaving the skin only half-covered. You don't need to make your husband wear anything more for him to feel exposed in such a blouse, but if you do, he'll find himself confronted by it whenever he looks down.

Many men are profoundly affected by satin, with its silky sleekness having a seductive allure that simply demands attention. Your husband will find it hard to concentrate when he must not only ignore how such shiny material catches the light, but also avoid being distracted by its caress of his skin, with this sleek fabric constantly calling for both his fingers and eyes to come to it. It's hardly surprising that crossdressers often have a particular penchant for satin, which, like lace, is rarely found in men's clothing. A white satin blouse has a sexiness even in a modest style, with soft pastels having an undeniable femininity, but to really emphasise what your husband wears, you might opt for a provocative shade such as red, burgundy or hot pink. Even in cotton, a conspicuous colour offers no escape for a sissy secretary, prominently announcing what he's wearing.

Skirts and trousers

Although some companies remain stuck in the past, an ever-increasing number permit women to wear trousers to work, rightly recognising that such garments have their place in the professional wardrobe of both sexes. There's no reason why you can't follow their lead when specifying what your husband should wear as a secretary, whether allowing him a pair of men's trousers, or requiring ones intended for women. Like blouses and shirts, the sort of trousers that a female secretary might wear to the office have a lot in common with those of her male colleagues, not least formal fabrics and colours, but there are still plenty of differences that will disconcert a man - if not a side zipper or an absence of proper pockets, then most definitely a less accommodating crotch! Simply knowing that he's wearing something meant for women can be unnerving enough, especially if combined with a shirt-like blouse, even though such an outfit might be sufficiently ambiguous as to not be noticed by anyone else.

While one might need to look closely in order to confirm that a man is wearing women's trousers, a skirt is obvious at a glance. Even a staid skirt calls for attention when worn by a man, with the difference being just as apparent to its wearer. Any skirt will have an impact, regardless of whether it is so tight that the male wearer must keep his knees uncomfortably close together, or is loose enough to allow air to reach his crotch in a way that trousers never would. If a skirt doesn't conceal a sissy secretary's manhood completely, then it will nevertheless reduce it to an unsightly bulge, no matter whether wearing such a womanly garment excites him or shrinks him down to size. Wearing a knee-length skirt, let alone one that's much shorter, will leave a man's legs feeling exposed, whereas a long skirt will challenge him with how it covers them.

The stereotypical secretary's skirt is a simple affair, lacking the sort of frills and flounces to be found in many blouses. That's not to say that a skirt with such features can't be effective at emasculating its wearer - indeed, a fussy peplum will add volume to a man's hips, whereas a mermaid hem will impart a swish while still allowing his skirt to remain suitably restrictive. A long, full skirt, perhaps with pleats, has a modest femininity that can take a sissy secretary back to a time when women were submissively demure, but generally, the kind of skirts that men associate with female assistants are shorter and tighter. While shortness merely offers an opportunity to add hosiery, tightness requires further consideration of how your husband's body differs from those of the women that skirts are designed for. Because men have a less feminine figure, a skirt that is sized to fit his waist is likely to be too narrow around his hips, such that it is better to avoid particularly high-waisted styles in favour of those that sit lower down, using his hip measurement for sizing. Men also have proportionally smaller buttocks than women, although this is balanced by them having more to cover at the front, even if it is flattened!

Just like their female counterparts, sissy secretaries can wear A-line, straight or even pencil skirts. So long as your husband can worm his way into it, a skirt that you might dismiss as too tight around the hem can actually be advantageous, because of how it prevents him spreading his legs when sitting or standing. Having his stride cut short by unyielding fabric will stress his submission should you have him scurry around, whereas being required to maintain a modest posture while seated will draw his attention to how he might otherwise present his crotch. Many such skirts have a split at the back to reduce the degree to which they impede the wearer, but this can easily be sewn up - indeed, it doesn't require that much work to take a skirt in, so as to make it even narrower! To really cause your husband problems, you might think about having him wear a hobble skirt, although this most restrictive of styles isn't something you'll find in shops, instead best considered as fetish wear and thus sourced as such - or, alternatively, made from scratch.

When a man imagines a sexy secretary, there's a good chance that he'll put her in a mini skirt - perhaps one so short and tight that she risks showing off her stocking tops or even her underwear if she doesn't keep tugging it down. The ease with which such skirts ride up can work in your favour should you have your husband wear one himself, whether you're intending to avail yourself of what it reveals, or merely want to make it hard for him to preserve his decency. Anticipating having his skirt hitched up, whether for pleasure or punishment, will add to a man's sense of vulnerability even if he's doing nothing more exciting than typing, whereas needing to fuss with what he's wearing whenever he sits or stands will make sure that it stays at the forefront of his mind. If a sissy secretary is only pretending to appear professional, then he can wear a skirt far more scandalous than a woman would ever wear to work, with preposterously short micro skirts being sold specifically to provoke passions, assuming you don't want to shorten a longer one. Either way, the connotations of garments more suited to the bedroom than the boardroom are clear, even if you repurpose them to frustrate rather than thrill your husband.

More professional skirts are generally made of the same sort of material as suit trousers, as well as sharing a similarly sombre range of colours. Black, charcoal and dark blue have an undeniable formality, but for a lighter, more summery look, you might consider a pale grey or beige, or else a pastel shade. Skirts that suggest work tend to be plain, with any patterns being subdued, but a black and white check or herringbone can convey a distinctly secretarial air, as can plaid. Of course, since your husband won't really be going to the office, his skirt can be rather more eye-catching - when worn with a white blouse, a royal blue, bold red or even vivid magenta will make his skirt the focal point of an outfit. Conversely, you might have him pair a white skirt with a contrasting blouse, or choose the two so as to combine their emasculating effects - a pale pink blouse worn with a darker pink skirt will leave a man in no doubt about the kind of clothing he's wearing, even if such an exaggeratedly girly combination wouldn't be the first choice of many actual secretaries.

As with blouses, you can make a skirt still more provocative for your husband by choosing one in a sexier material. An otherwise unremarkable skirt can nevertheless madden a lover of satin if it has a silky lining, regardless of whether it caresses his skin or emphasises the presence of hosiery. There's no reason to stop there, however, with satin skirts being available in styles that are suggestive of secretaries, yet have a sumptuous luxury of their own. The combination of a black satin skirt and a white satin blouse can have a profound impact upon a susceptible man, even without him wearing anything in the way of satin beneath, whereas bolder colours offer the opportunity for complementing his lingerie. You needn't stray into fetish wear if you want something saucier, although a PVC or latex skirt can certainly pack a punch. While not as shiny as those, faux leather remains plausibly professional, despite the messages it sends, and thus can serve as part of a sexy, yet secretarial outfit.


Even the longest of skirts will leave at least a little of a man's legs bare, with some revealing substantial amounts of skin - a far cry from the more familiar covering of trousers, making men's socks and shoes look rather silly. While it's possible to combine such incompatible elements to create an outfit that's deliberately ridiculous, you'll struggle to find a professionally dressed woman wearing anything similar. As far as stereotypes are concerned, secretaries wear hosiery, with such legwear setting them apart from their male colleagues. Men generally do not wear pantyhose or stockings to work - at least, not openly - and they certainly do not show off their legs like the women they might fantasise about.

It's easy to understand why many men are fascinated by women's hosiery, which is unlike anything to be found in their sock drawer. The plainest of pantyhose nevertheless emphasise the shape of a secretary's legs by smoothing and firming them, allowing her to flaunt her femininity even in a stuffily traditional office. From the male perspective, the practical reasons why professional women might wear hosiery pale in comparison to its erotic charge, with a pair of nylon-clad legs naturally leading a man's thoughts up between them. Sheer nylon is not only sensuous to look at, however, but also to touch, its silkiness inviting a caress while requiring respect if such delicate material is not to be snagged. All that's before considering the thrilling sensations experienced by a man wearing hosiery himself, with this clinging second skin asserting its presence whenever he moves.

Some crossdressers get so caught up in their daydreams that they don't appreciate that men are hairier than women, which might seem a problem if you'd prefer that your husband didn't shave his legs. Fortunately, any sort of nylon will flatten masculine fuzz against the skin, with thicker hosiery capable of hiding it completely. A pair of opaque nude pantyhose will make your husband's legs look like they're bare while he's wearing them, yet can be removed in no time at all. While you might never consider layering your own hosiery, having him wear a second, sheer black pair on top offers the best of both worlds, making it appear like he really does have hairless legs. If you don't want your husband's hand heading up his skirt while he works, then each pair will put an extra obstacle between him and his manhood, something you can emphasise by choosing pantyhose with a control top. Of course, heavy hosiery can become oppressively hot and sweaty in warmer weather, with two pairs doubling the discomfort, but you may decide that your secretary would benefit from enduring that for the sake of his appearance!

A man doesn't need to be able to see his hosiery to know that he's wearing it. Even beneath trousers, there can be no ignoring how nylon envelops the legs, with any concealment that an outer layer offers coming at the cost of it constantly sliding over what's beneath. The same is true for skirts, but the shorter they are, the more they risk revealing whether hosiery takes the form of pantyhose or stockings. When one considers how the latter are regarded by many men, it would be understandable if you eschewed stockings yourself for fear of sending the wrong message, but once again, things are different for a sissy secretary! Even the plainest of stocking tops are provocative thanks to their proximity to parts of the body that would be inappropriate to expose at work. If a simple, darker band running around the thigh is sexy, then how much more so one made of similar floral lace to lingerie, if not stretched into seductive arches by straps that speak of equally exciting undergarments!

In a professional environment, there's no reason why anyone should ever know whether a particular secretary prefers pantyhose or stockings, but in men's sexually charged daydreams, stocking tops are frequently found on show - for example, when a short-skirted assistant bends enticingly over a filing cabinet or desk. To disabuse your husband of any misconceptions he may have about women inviting attention, you can set him up to be scolded for showing more than is seemly, or alternatively, insist on him wearing the more mundane, sensible hosiery that a real secretary would prefer for work. The tendency of hold-up stockings to fail to live up to their name can be turned to your advantage if you want your husband to have to endlessly fuss with both them and his skirt, but they can also provide a pretext for having him wearing a garter belt or even an old-fashioned girdle, should you prefer - garments that we'll discuss shortly. It should be noted that some men have a particular penchant for pantyhose, perhaps because of how they cover the crotch, but it's up to you whether you indulge your husband if he does!

We've already discussed how nude hosiery can be mistaken for skin. While this most neutral of colours won't draw attention to a man's legs beyond imparting an illusion of greater femininity, it will serve to emphasise any shoes. Black hosiery can also complement the subdued shades of secretarial skirts, and thus is capable of conveying a similar formality, even if men are more attracted to it! You can add a vintage kick to either nude or black by having your husband wear fully fashioned stockings, which have the additional challenge of seams that must be straight if they're not to look unsightly - no mean feat if he's not used to them, yet with his success or otherwise mostly hidden from his view. Depending on the rest of his outfit, you might alternatively consider brown, grey or navy blue as colours for stockings or pantyhose, all bringing to mind more modest women. Combined with an unassuming skirt and blouse, deliberately humdrum hosiery can reduce a man to the most humble of secretaries, far removed from the femme fatale of his fantasies, yet still undeniably unmanly.

Because a sissy secretary's legs won't be seen by anyone but himself and his boss, you can have your husband wear much more conspicuous hosiery. Fishnets of any variety are suggestive, but have the benefit of being harder to snag than regular stockings - something that a man new to wearing women's legwear will welcome, even though he'll be accosted by both the sight and feel of them criss-crossing his skin. Ultra-sheer hosiery is best avoided by men with rough or clumsy hands, as exciting as it may be, but don't assume that the opposite must be boring. Opaque pantyhose in a striking colour can act as the highlight of an otherwise drab outfit, or make one that's already gaudy even more eye-catching. Once again, hot pink and red are effective choices, but you might also consider turquoise, green or yellow, with the same shades working well in lighter deniers. Last, but by no means least, it's impossible for a man to feel very manly when he looks past the hem of his skirt to see legs embellished with floral patterns, no matter whether these are the traditional black or brightly coloured. Could a real secretary wear similar to work? Perhaps not without attracting attention, but that's the purpose of such hosiery!


Even in men's fantasies, few secretaries scamper about the office in only their stockinged feet. That being said, a man playing the part of an assistant can manage perfectly well without footwear if he won't be leaving the house - indeed, there's lots of fun to be had with exposed toes, regardless of whether or not they're encased in nylon! Alternatively, you might have your husband wear feminine hosiery with regular men's shoes, creating a contrasting combination that can engender a profound sense of exposure or embarrassment. Could a man stand up in a meeting if he had only his shirt and socks with which to cover a provocative pair of fishnet stockings? The same humiliating vibe can be employed safely in private should you wish to have him make amends, or even to excite him.

For the most part, however, secretaries wear women's shoes - in the real world, ones that look professional, yet are practical enough to meet the demands of a busy day. That means flat or low heels, not the impractically high spikes that men might dream about sexually-charged stereotypes strutting or tottering around in, generally in black or neutral colours such as brown or beige. Such shoes have closed toes, and lack excessively fussy straps or other features, often being slip-on affairs. Sissy secretaries can wear similarly unremarkable styles as part of a female outfit, with differences in both design and fit enough to stress that such shoes are not the same as men's footwear. Regardless of formality, they must be clean and polished - it should go without saying that sneakers are a no-no, especially not grubby ones!

While some men are oblivious to how uncomfortable and impractical stilettos can be, others are drawn to them for that very reason! High heels affect the wearer's balance, requiring even a woman accustomed to walking in them to emphasise her bust and buttocks. Your husband needn't have feminine curves in order to feel vulnerable in stilettos, however, nor even to walk anywhere - simply sitting in such shoes will see him having to adopt a different posture, with the unfamiliar arch of his feet challenging a surprising number of muscles! He certainly won't be striding anywhere with manly confidence, instead reduced to a cautious shuffle for fear of taking a tumble. The resulting sense of helplessness can be very appealing to a submissive crossdresser, even before one considers the connotations of shoes that are so erotically charged. Stiletto heels are sexy, especially when worn with sheer stockings, conveying a femininity that men are deeply affected by.

Because of these associations, suggestive footwear may be found in men's sizes from specialist suppliers, albeit skewed towards styles that summon thoughts of strippers rather than secretaries. You might take advantage of this by having your husband wear shoes that bear only a passing resemblance to anything that a professional woman would wear to work - for example, pumps that not only have a provocatively pointy heel, but are also a bright, shiny red. Many such shoes are made from patent leather, which has an allure not dissimilar to that of satin, calling to the eye even in more conservative colours. Needless to say, the appeal of high heels will soon fade when a man's feet start to ache, but that doesn't mean they should be easy to slip off! Having to unfasten a single strap, let alone multiple fiddly buckles, will add to your husband's sense of being stuck in women's shoes, but if that isn't enough, it's possible to buy fetish footwear with integral locks, ensuring that he wears them until you decide otherwise.

Rather than go that far, however, you might consider boots that lace up or fasten with a zipper, both requiring a deliberate effort to remove. While still appearing reasonably professional, a pair of black lace-up ankle boots can prove surprisingly difficult for a man to take off, particularly if he's impeded by other clothing, but for a more provocative look, you might have your husband wear ones that stretch further up his leg. Except for the most extreme of thigh boots, which invariably have stilettos, it's possible to find such footwear in a range of heel heights and styles, allowing you to choose a combination that suits your circumstances. You might reserve perilous six inch spikes for when you want your husband to feel especially submissive, or alternatively, set them as a target for him to work towards, employing more manageable kitten heels to begin with. Over time, a man will find his feet in whatever he wears regularly, but even when he can scurry around in women's shoes as proficiently as a real secretary, he won't be mistaking them for anything he'd normally wear! If the idea of training your husband to walk in high heels amuses you, or you don't want him to dress up further for whatever reason, they can be worn with men's clothing as well, regardless of whether he's standing, sitting or simply lounging around!


Nothing illustrates how differently men regard women's clothing better than lingerie. Whereas a female secretary is more likely to prioritise comfort over sexiness when choosing what to wear under her blouse and skirt for a long day at work, a man undressing her in his mind might hope to find a thong and push-up bra in place of anything plain and practical, perhaps accompanied by a similarly suggestive garter belt. From this stereotypically male perspective, a secretary's underwear is not something that needs to be modest for fear of attracting unwanted attention, but rather an opportunity for her to flaunt her sexuality. Lingerie is powerful stuff, being capable of affecting men far beyond the bedroom - indeed, such is its allure that even the slightest of hint of intimate attire can be excitingly distracting. That's hardly surprising when one considers how women's underwear simultaneously conceals, yet emphasises parts of the body that are ordinarily off-limits to all but lovers, but such garments don't just have sexual connotations - they're quintessentially feminine too, being very different to male clothing even when they serve a similar purpose.

If a man is already wearing a skirt, then it's only natural to expect panties underneath - in fact, it would be incongruous to discover that he was hiding a pair of baggy boxer shorts beneath such a womanly garment! Figure-hugging skirts of the sort often found in stereotypical outfits call for close-fitting underwear if a man isn't to have more of a bulge than is absolutely necessary, ruling out looser options. Such panties needn't be particular provocative, however - modest styles are actually better suited to keeping a sissy secretary's manhood in check! Making no allowances for his anatomy, the less roomy cut of women's underwear will feel different even under trousers, but the physical sensations are only half the story. Simply knowing that he is wearing panties can have a profound effect on a man's state of mind, even if they're difficult to distinguish from men's briefs. A pair of plain white cotton panties can be as emasculating as anything to be found in an adult shop, with their practicality stressing that they are being worn for a purpose other than sexual arousal.

Men don't wear bras in the same way that women do, not least because most don't have breasts, which gives this most feminine of garments a unique power as a result of its apparent pointlessness. Don't think that your husband needs to fill the cups of a bra in order to be affected by wearing one, as he'll find it hard to ignore the unfamiliar tightness accosting his torso even without anything weighing it down. As with panties, you might have him follow the lead of female office workers by wearing a simple white or nude affair, with an absence of embellishments not detracting from a bra's unmanliness. While these muted colours aren't as conspicuous as some we will be considering, the outline of even an unpadded bra may nevertheless show through a shirt or blouse, if only as tell-tale bumps and ridges. Without adding anything more, you can engender a deep submission by having your husband wear a bra under his regular workwear, or for a more prominent effect, make him strap one on top.

Although bras are available with bands wide enough for men, these are rarely paired with smaller cups, such that it is unrealistic to expect to find ones that fit your husband's natural measurements without seeking the help of a specialist supplier. Fortunately, bras can be filled by other means, not that one need even do that with those that have integral padding. The moulded cups of a T-shirt bra will add curves to a man's chest that can be stuffed with something as simple as socks to stop them from collapsing, or alternatively be given a realistic wobble and weight with a pair of water balloons. Skin-coloured silicone inserts are also available, ranging from small slips intended to boost an existing bust right through to full chest prosthetics that not only have realistic nipples, but also simulate cleavage. Even the crudest of contrivances will become more convincing when covered, making your husband look and feel less manly.

A pair of ambiguous bulges can be more than enough to make a man feel self-conscious, especially if he's otherwise wearing male clothing. At the other extreme, implausibly large false breasts will reduce him to a parody, challenging his back as much as the buttons of his blouse. Becoming a busty bimbo can be very exciting for some submissive crossdressers, but the initial thrill will soon wear off, leaving an increasingly troublesome burden. Rather than having to worry about finding outerwear to fit a prodigious chest, you might have your husband wear a stretchy white top in place of the traditional blouse, which can be made more professional by being accompanied by a smart suit jacket. It doesn't matter if he can't fasten the latter - indeed, that will only serve to stress his eye-catching curves!

In the real world, secretaries do not have preposterously large breasts, any more than they can avoid wearing a bra to work, no matter how much some men might prefer otherwise. Instead, women's clothes are cut for more commonplace figures, meaning that a modest bust will help a crossdresser's blouse fit better. Breasts that are unremarkable by female standards will nevertheless emasculate a man, as well as providing an opportunity for him to learn about the true purpose of bras. When being worn to support separate forms, a style that keeps each of the breasts in a well-defined cup is preferable to a skimpier one that pushes them together, sensible being better than sexy if the filling isn't to fall out! Underwires will also help to support false breasts by giving structure to the bottom of the cups, preventing slippage so long as the band is suitably tight.

While few companies have a dress code that explicitly specifies underwear, a secretary would likely find herself on the receiving end of a quiet word were she to break the unwritten rules by flaunting inappropriate intimate attire. You might expect similar modesty from your husband, going so far as to insist that he wear a nude bra and briefs to stress the importance of not showing anything unseemly while at work. Alternatively, you might require him to wear a camisole, whether clingy cotton or silky satin, adding a further layer of femininity to his outfit, not to mention additional shoulder straps. Thicker, heavier outerwear will make it hard to distinguish between provocative and plain when it comes to his underwear, but the knowledge that he is wearing something naughty under his other clothes can nevertheless prove thrilling. Thong panties are particularly distracting in this regard, with a man's bulkier crotch encouraging the back of this cheeky style to tug up between his buttocks.

Rather than try to hide their lingerie, however, many submissive crossdressers want to show it off! Wardrobe mistakes that women would go out of their way to avoid often appeal to such men because of the suggestive messages that they send - none more so than wearing a black or other conspicuously coloured bra beneath a sheer white blouse. Such a striking combination demands attention, especially if the bra is padded enough to stretch the blouse, confronting the wearer with its outline whenever he considers his chest. No matter how your husband feels about wearing a bra, being reminded that its band and straps are announcing themselves on his back will further add to his awareness of it, even without you finding pretexts for him to bend over. Similarly, a pair of panties that are intentionally too small will betray their presence under a skirt when the latter stretches taut, all the more so if its fabric is thin. Your husband needn't wear women's clothing on top in order to be affected by bra and panty lines, however, with these also capable of showing through a shirt and trousers.

One reason a female secretary might not want to wear stockings that require separate support is a fear that the bumps of garter clasps will inadvertently give away her secret, but your husband need have no such qualms, no matter how you might tease him about titillating his colleagues. Again, such subtle suggestions of intimate attire can delight a man with a weakness for wearing lingerie, but it isn't just crossdressers who consider garter belts to have a profound sexual charge. Separate to the allure of straps stretching over buttocks and thighs, these garments offer a practical way of ensuring your husband's hosiery stays up, so long as he wears a style suited to the male body. As we have already discussed, men do not have as pronounced hips as women, and thus benefit from deeper, sturdier garter belts designed with functionality in mind, rather than the flimsy affairs whose superficial charms might entice their eye in a lingerie shop. Moreover, when a garter belt is worn over, rather than under, a man's panties, it makes it harder for him to slip a hand into the latter, let alone pull them down!

Men can wear panties, stockings and even bras when not playing the part of a secretary, with such garments offering a wealth of benefits for both husband and wife, whether in the context of the bedroom, or beyond! The books brassièred: a complete guide to brassière discipline and put him in panties discuss how and why you might have your husband wear women's underwear in greater detail.


At the start of this chapter, we discussed how choosing women's clothes for a sissy secretary isn't the same as doing so for yourself, and few garments illustrate this more clearly than underwear. As difficult as it can be to find an acceptable compromise between comfort, support and appearance, you're unlikely to want to be distracted by your intimate attire, surely scoffing at any suggestion of deliberately wearing disagreeable or restrictive underpinnings - especially to the office! With sissy secretaries, however, the priorities are very different - appearance is much more important, albeit with a distinct disregard for, if not an attraction to, fashion faux pas such as visible bra straps and panty lines, whereas concerns about comfort can be turned on their head. If the back of a pair of panties bunches up between a man's buttocks, or the underwires of his bra dig into his chest, so much the better, in so far as such irritations serve to remind him of his submission to lingerie.

This line of thinking can be extended to more substantial undergarments, especially those that have the side effect of limiting what a man can do. When it comes to control, there's no contest between a pair of everyday panties and a style specifically designed to shape the body, whereas the impact of a regular bra pales in comparison to a longline one whose embrace extends all the way down to the hips. The idea of wearing a stiffly boned waist cincher, let alone a full length corset, might be anathema to any sensible secretary, but many submissive men dream of being left short of breath because of how strictly they're laced, quite apart from any effect such garments might have on their waists! Furthermore, old-fashioned foundation wear of the sort that modern women have generally rejected brings to mind a time when a secretary's wardrobe required her to make greater sacrifices for the sake of her appearance. Its restrictiveness encourages a man to fall into a similarly submissive mentality when donning it, yet it retains a powerful feminine allure even when he's trapped inside it.

Today's shapewear is not as different to that of bygone days as its marketers would like to suggest - after all, women's bodies still have the same problem areas! Although a masculine bulge is not one of those, a pair of modern control panties or shaping shorts can nevertheless flatten a man's crotch, with styles that emphasise function over form further suppressing unwanted swelling. Such garments are generally far from sexy, but they don't need to be seductive if they're going to remain hidden under your husband's skirt. For something more feminine than featureless beige, it's worth consider vintage or retro styles, which, as well as being more likely to feature satin or lace, often have straps to support stockings. That makes them an ideal alternative to a garter belt, making sure both your husband's manhood and his nylons stay where they should!

Girdles can be divided into three main types, depending on how they cover the crotch. All have self-explanatory names - an open bottom girdle is open at the bottom, being like a sort of skirt, whereas a panty girdle is closed, and a long leg girdle extends down the thighs. The latter two styles may be compared to control panties and shaping shorts respectively, but any sort of girdle will prove emasculating. Each variety is available in various lengths, with the most substantial coming up to just beneath the band of a regular bra. Rather than being pulled on and off like a pair of panties, sturdier girdles are often fastened with a zipper over a set of hooks and eyes, ensuring that your husband won't be getting out of one without work!

Even an open bottom girdle will restrict access to the crotch. While some panty and long leg girdles have contrivances to allow the call of nature to be answered without removing them completely, these can easily be sewn closed, with the resulting sense of being trapped in a torso-length tightness capable of affecting a man's mind as much as his body. Despite it being impossible for a sissy secretary to forget that he's wearing such a formidable garment, all but the longer open bottom girdles can be worn under trousers without being obvious to anyone else. Indeed, even beneath a skirt, a few ambiguous lumps and lines may be the only indication of the lengths to which a girdled man has gone to control his figure, his flatter stomach being just as likely to catch the eye! If the idea of having your husband wear a girdle appeals, the subject is explored further in a brief guide to girdles for men.

In the fifties, a female secretary might accompany her high waist girdle with a longline brassière, so as to leave not the slightest bit of flesh uncontrolled between her bust and her hips. The same combination works a treat on a sissy secretary today, especially if one chooses an authentic style - indeed, separating the top and the bottom halves of a man's foundations will yield better results than expecting a single piece of shapewear such as a corselette or a bodysuit to perform both functions, thanks to how the bra and girdle may be sized independently of one another. Although you needn't have your husband fill out a longline bra, these substantial garments are generally well-suited to supporting larger false breasts, with old-fashioned designs having cups that provide plenty of coverage, as well as benefiting from sturdy shoulder straps. Moreover, a longline bra presents a man with a challenging number of hooks and eyes that must be unfastened before he can escape its clutches! Rather than leaving your husband to battle those himself, you might encourage him to seek your assistance when dressing and undressing, inculcating a sense of helplessness to your advantage.

The bullet bra is a particularly potent symbol of fifties femininity, with its provocative conical cups summoning images of sexy sweater girls - not that a man needs to be put in mind of pin-up models to be affected by a pair of preposterously pointy breasts. The implausibility of such a shape only adds to its power, especially for larger sizes, regardless of whether the eye-catching protrusions stretch a blouse or merely a shirt. A resurgence in retro fashion means that this vintage style is easier to find than you might think, with some manufacturers even offering longline options to match similarly traditional girdles. Alternatively, you can have your husband wear a bullet bra on top of other foundation wear, stressing its purpose without compromising on control. While few women would want to wear two bras to work, submissive crossdressers are often of the opinion that twice as much lingerie is twice as exciting, whereas even men without a penchant for female underwear will be left helpless by multiple layers.

No discussion of shapewear would be complete without considering corsets, which can be divided into two distinct types. Firstly, there are fashion corsets, which are given their shape by means of flexible plastic boning that will bend under pressure. Although these will impose upon a man's body, they are best considered as fancy lingerie, often being made from luxurious material and featuring lots of frills - a treat for any man with a love of satin and lace, however uncomfortable or cumbersome they may be, making a sissy secretary feel naughty even when concealed by other clothes. Many such corsets have garter straps, allowing them to be spiced up further with stockings, with some even having shaped cups so as not to need a separate bra. Throw in the ridiculous G-string that these garments are often sold with, and you have a very sexy, albeit impractical, set of underwear, offering plenty of scope for fun should you pretend not to know what your husband is wearing until a pretext presents itself for inspecting his intimate attire!

Steel-boned corsets are significantly sturdier, requiring the wearer to conform to their curve rather than the reverse. Putting a greater emphasis on shaping, such corsets can be rather plain, reflecting how they are worn primarily to reduce the waist. Because of their rigid structure, it is once again necessary to take into account the way men's bodies differ from women's when choosing one, with shorter cinchers generally working better than corsets that extend over the hips or bust. A short waspie can nevertheless be combined with a heavily padded bra to give a male secretary an undeniably feminine figure, even if he can't fully achieve the stereotypical hourglass associated with such garments. Furthermore, a basic black waist cincher is professional enough that it can plausibly be worn as outerwear, perhaps over a contrasting blouse to emphasise an enhanced chest.

Regardless of how a man wears a corset, he'll have to contend with a tightness which not only limits his movements, but also how deeply he can breathe. A corseted secretary will soon feel lightheaded should he be expected to exert himself while firmly laced, which can be both exciting and exasperating, but the physical effects of a strict corset don't stop there. Stiff boning will enforce proper posture when sitting, while also requiring a sissy secretary to consider how he bends and stretches, adding a challenge to even seemingly straightforward tasks - indeed, simply getting into a sturdy corset can be a struggle! Although you can have your husband lace his own corset without any assistance, taking charge of its cords is a great way to assert your authority, even if you let him do most of the work and only tighten them a little. Once tied off, you needn't worry about him removing anything underneath in a hurry, providing another reason why you might have him wear one on top of a blouse!

Jackets, sweaters and cardigans

While some men might be required to roll up their sleeves for work, others must maintain a more professional appearance, not only expected to wear a shirt and tie, but also a jacket that matches their trousers. A man trying to hide a bra or a blouse will welcome an extra layer of male clothing, however inadequately it might conceal what he wears underneath, such that you might deny your husband a jacket to make him feel more vulnerable - after all, many secretaries wear nothing over their blouses in the office! Nevertheless, a two-piece suit conveys a certain professionalism, with a smart women's jacket and skirt suggesting that the wearer is ready for business - albeit not as a man!

Like other garments designed to fit the female figure, a woman's jacket will challenge the male wearer because of the shape of his body - in particular, his broader shoulders. The more structured a jacket is, the more likely it is to restrict a man's arms, even without being buttoned up. Women's jackets are also comparatively narrower around the waist whilst being more accommodating in the bust, with off-the-rack garments making assumptions that a man is unlikely to be able to meet without assistance. Having your husband wear a padded bra won't help if it makes him much bustier than the average woman, however, although a formal jacket does permit a more relaxed top if you don't want to go to the trouble of finding a blouse to fit preposterously large breasts - indeed, for an immodest look, you might instruct your secretary to skip the top entirely, putting the cups of his bra on show! No matter what he might wear underneath, a jacket that only buttons below the bust will serve to stress the latter's size, while also chiding a man should his stomach bulge too much.

Suit jackets are generally sold to match skirts, meaning that they're available in the same colours and fabrics we discussed earlier - most commonly, businesslike black, grey or beige, not that even the drabbest of shades will make a tailored or fitted cut easy for a man to wear. Regardless of style, a pastel pink skirt suit will prove particularly emasculating, whereas a hot pink or other bold colour will assert itself far more than any man wearing such a suit ever could. Speaking of hot, a heavy jacket will trap the heat, especially if you insist that your husband keeps it buttoned up over a high collar blouse and a woman's tie or neck bow. If you don't want him to swelter too much, you might consider a woman's jacket in a waistcoat style, which, as well as leaving the sleeves of his blouse uncovered, will give him an air of being a female office assistant or even a receptionist. Again, these are sold to be worn with skirts, with separates allowing a better fit for a man's body.

For a less formal look, you might have your husband wear knitwear instead. A clingy sweater will make no secret of a padded bra, even without choosing one with a scoop neckline, but the latter needn't expose more than his blouse should it be paired with something more modest underneath. We touched on sweater girls when discussing fifties foundation garments, but fluffy knitwear has a femininity that can be separated from being stretched across conspicuous breasts - the look and feel of angora or mohair can be enough to make a man weak without anything more, especially in soft, girly pastels. If having to work while enveloped in pink fuzz is too much for your secretary, however, you might consider a plainer cardigan for him. It doesn't matter if it's a bit frumpy - indeed, this may be a benefit if you don't want your husband to associate his secretarial wear with sexiness. A style with plenty of buttons will add to a sense of being trapped in women's clothes should you require them to be done up, regardless of whether his cardigan hugs his figure or is more baggy.

Accessories and cosmetics

No-one seeing a man dressed as a secretary is likely to think that he's the boss, even if he wears exactly the same clothes as a dominant businesswoman! To remove any doubt about your husband's position, however, you might have him wear a name tag that announces he's a submissive assistant. This needn't be a tag, nor even bear his name - an address label bearing a suitably impersonal title can be stuck to a blouse, jacket or even his forehead for the duration of a secretarial session, with a sheet of such stickers allowing you to call him something different each time. You don't even need to scrawl on them yourself, as entertaining as that can be, but can leave the task of writing or printing the necessary words to your secretary - after all, he will be wearing them!

A plastic pocket on a lanyard can be used similarly, with both badge holders and the means of hanging them around a man's neck being readily available from stationers. As well as tags that pin or clip in place, custom-made plastic or metal badges are available at a modest cost, as are straps with personalised text and colours, such that it's easy to have your husband wear something that looks surprisingly professional whilst nevertheless being provocative. A name tag that's positioned prominently on the upper curve of a breast will catch a man's eye, particularly if at least part of it is printed upside-down so that he can't avoid reading it. Conversely, a strap will dangle from any bust, and also provides something that you can pull in order to assert your authority.

Costume jewellery can be chosen to emphasise the persona suggested by your husband's other clothes. A mature secretary might wear a pearl necklace and matching earrings, albeit with the pearls being only cheap plastic, whereas a younger one might wear a prominent pendant, perhaps bearing an emasculating moniker, and conspicuous hoops. No piercings are needed for clip-on earrings, with a sissy secretary able to wear much larger ones than would be appropriate for the office. If dangly jewellery distracts him or gets in his way, so much the better - indeed, you might have your husband wear a bracelet or bangles solely for the inconvenience! While a close-fitting choker won't do that, its presence around his neck will do more than simply conceal his Adam's apple, serving as a symbolic collar that will remind him of his subordinate status. Lastly, if your husband doesn't already wear spectacles, it's possible to buy novelty glasses specifically for the purpose of looking like a stereotypical secretary, having oversized frames to help him really feel the part.

Some submissive crossdressers are very keen on using powder and paint in order to look more feminine, whereas others are less enthusiastic about wearing make-up. A full discussion of men wearing women's cosmetics is beyond the scope of this book, but unlike much of what we have discussed so far, the impact on your husband of wearing lipstick or eye-shadow is more in the initial application of these unmanly beauty products, unless you arrange for him to be reminded about it - perhaps by the strategic placement of a freestanding shaving mirror. One area where that isn't the case, however, is nail polish, such that if your husband is going to be playing the part of a secretary for a reasonable length of time, you might have him paint his nails prior to starting. Doing anything with his hands, not least looking at the keyboard as he types, will confront him with their colour, whether that be a bold red of the sort that men are instinctively attracted to, a more muted burgundy or beige that wouldn't be out of place on a businesswoman, or an undeniably girly pastel pink. Even a coating of clear polish will catch the light, as well as requiring attention afterwards to remove, thus extending the duration of your husband's employment.

What sort of secretary might he look like?

Any sort of female attire is likely to affect your husband, especially if you stress its significance in making him a secretary. The more in the way of women's clothing he wears, the more easily he'll find it to fall into an associated character, even if the individual garments don't really go together. While a deliberately mismatching outfit can be used to make a man feel ridiculous, it's generally better to choose clothes that work together when creating a costume, having a particular sort of secretary in mind. Let's consider a few possibilities:

Of course, you don't have to limit your secretary to these options, but can have him mix and match to encourage particular moods. From classy to trashy, chic to drab, sissy secretaries can wear all sorts of clothes! Is your husband taking on the persona of an impoverished temp who must make do with whatever can be found in the bargain bin of the cheapest clothing store, or an exclusive executive assistant whose snobbish boss will accept nothing less than the most fashionable designer skirts and blouses? Either can augment any of the outfits described above - indeed, you might set your secretary the challenge of looking elegant on a budget! If you lack strong feelings about such matters, you can delegate the details to the man who'll be dressing up for you, albeit reserving the right to veto anything that your husband might suggest. As we'll discuss in more detail in the next chapter, putting together a collage of possible options is an ideal project for a sissy secretary, even if he never purchases any of them, requiring him to think about why women choose the clothes they do.

Finally, your husband isn't the only one who can get dressed up for a secretarial session - if you're feeling in the mood for it, you might slip into something suitably businesslike yourself! It doesn't take much to look the part of a boss, with many of the garments we've discussed in this chapter having a profound effect on a man when a woman wears them - unsurprisingly, considering how we've been looking at clothes with unashamedly feminine connotations. Moreover, the distinction between a submissive secretary and a commanding businesswoman is more one of attitude rather than attire. Because of how you'll wear it better, you can assert your authority in an identical outfit to your husband, but you might stress your superior status by opting for more luxurious materials - silk in place of synthetics, for example. Of course, there's no obligation for you to get all dolled up, especially not for his benefit, although dressing as you would for a date is sure to have quite an effect! Indeed, remaining casually dressed can make a man feel even more out of place if he's expected to present himself professionally, even if he wears nothing more conspicuous than a traditional suit and tie!

Whatever you or your husband wear, dressing the part is generally only the start of a secretarial session. In the next chapter, we'll consider what you might have him do once he's suitably attired, exploring office-themed tasks with a range of purposes. From how he might make himself useful in his new outfit to ways of ensuring that he stays busy once dressed, your secretary needn't simply sit around - unless, of course, that's what you want him to do!