Hiding Your Lingerie At Work – The Discreet Trans Gentleman

A number of gentlemen prefer to wear ladies lingerie under their everyday work clothes. In this article we will provide some guidance and tips (sizing, styling, shopping, health and safety).

In our last blog we discussed how one androgynous male dealt with his gender uncertainty by undergoing a full gender transformation (if you missed it just click here).

Hiding Your Panties at Work 1 A good belt can help

However most gender fluid individuals don’t want a full transformation to the opposite sex. They can be visualised along the gender continuum as fairly close to their ‘biological’ or ‘birth’ gender but they feel comfortable adopting opposite gender attributes some of the time. These attributes may relate to dress, make-up, mannerisms or bisexual behaviour.

With regard to dress some ‘birth’ males hesitate in wearing a full ‘opposite gender costume‘ in public, at work or with their family. There may be many reasons for this – perhaps they are simply not ready to go ‘all-out’ or maybe they like female undergarments but don’t feel comfortable wearing over-garments (skirts, dresses, blouses). Therefore, in order to satisfy their natural gender fluidity, they wear lingerie normally associated with women underneath their day-to-day public attire.

Hiding Your Panties at Work 2 Plain, neutral colours can help if public undressing is normal

This is a phenomenon commonly adopted by both sexes and made much easier by the rise in on-line retail sales’ sites for clothes. In today’s blog we will concentrate on issues relating to males who choose to wear female underwear (don’t worry ladies we will address this issue for yourselves in a later article).

3 Men selecting work lingerie should consider any safety related issues






One of the first things you need to consider is whether you will feel embarrassed buying clothing normally marketed for the opposite sex. For some individuals however the excitement of cross-gender shopping is something they are particularly attracted to. Some folks actually derive a kind of extroverted thrill in seeing the expression on a sales person’s face when a guy asks for an item of ladies’ lingerie.

4 One challenge can be to find the right size

If you do want to use traditional retail outlets to purchase your gender fluid wardrobe one easy approach is to explain that the clothes are for your wife or partner (‘she is about my size’).

Sometimes gender fluid individuals in heterosexual relationships are very open with their partners about their cross-dressing desires. This openness can help because the partner can then accompany them and provide support on shopping trips. When it comes to buying women’s apparel ladies generally have considerable experience and add to the sense of fun (If you’re lucky they may even pay!).

5 Having a lady partner accompany you when shopping can help with sizing, style and colours



Having a lady accompany a cross-dressing guy when shopping for intimate apparel can have several advantages. If the lady is roughly the same size as the gentleman (or can easily gauge the difference) the opportunity presents itself for her to try on relevant garments on behalf of her partner. It is not unheard of for ladies to call out from the changing cubicle: ‘Please ask my husband to pop in and help me decide‘. Once inside the chap can try on the goodies himself.


By the way ladies have you given any thought to the possibility that your dear partner may have a secret passion for wearing ladies’ lingerie? Keep in mind that a lot of chaps are a bit shy or reticent with regard to discussing such matters (or perhaps maybe just ‘a bit old fashioned’). You might try mentioning to your bloke that it would really please you if he tried on some of your favourite lingerie (or if there is a bit of a size difference you could ‘accidentally’ order the wrong size for yourself – ‘Oh darling how silly of me – would you like to try them on to see if they fit you?‘).

6 Being open with partners about trans desires can add a new dimension to a relationship
7 Cross Dressing can bring out the hidden ‘romantic’ in a man

You may be surprised how many chaps, once given the opportunity, quickly open up about their own gender fluidity and quite enjoy trying on more sensual ‘ladies’ garments. In fact if you are finding that your relationship is starting to get a little repetitive you could be pleasantly surprised by how much a bit of cross-dressing can perk things up. Of course it does not have to just be one way (see my ‘Ladies in men’s boxers’ blog – coming soon!).  I remember the excitement when David Beckham admitted on TV how he ‘enjoyed wearing Posh’s smalls’  around the house – this iconic revelation probably helped to rejuvenate multiple marriages.

So back to the shopping. Don’t worry chaps if you don’t have a suitable partner to accompany you or if you are too shy to purchase your lingerie in person. Today most of us buy loads of stuff on-line and this trend is probably responsible for dramatically increasing the number of people who can now carry out cross-dressing procurement in the privacy of their own homes.

8 Buying online you may be able to try more than one size

The problem of deciding the correct size has also been helped by this cultural shift. Due to the inconsistency of sizing (especially when you buy clothes made in another country) people commonly order more than one size on-line and return the one that does not fit. This may seem wasteful but the on-line retailers know they are saving a fortune by not having to pay rent for high street physical shops with changing rooms.

Although you may be permitted to return wrong sizes they should ideally be tried on over a suitable undergarment – re-sellers do not look favourably upon returns accompanied by pubic hair or other bodily ‘remnants’. In addition it is good to have a rough idea of the size that is most likely to fit you. You do not want to order 10 different sizes and return 9! Most re-sellers (e.g. Amazon) have size charts to provide guidance. After making a couple of purchases you should get close to your preferred size.

9 The many forms of ladies knickers sit differently on men

When men buy women’s clothes they also need to remember that the body shape and contours differ. Generally speaking ladies knickers do not go round your waist at the same level as the classical men’s boxer short. In fact depending upon the type of knicker (string tanga, mid-line, full body brief etc) the elastic will sit at a different level.

I’m afraid a degree of sizing trial and error will be necessary in the early days. If you find a good fit from a reliable supplier it makes sense to stick with them (especially if they have a large collection). One thing to be particularly careful about if you have a typical ‘western’ male body size is with purchases from Asia. Even when a bloke buys men’s apparel from Asia the sizes are invariably too small (a US Medium is probably more like an Asian XL or XXL).

10 HSE: For long periods at work avoid lingerie that is too tight

So if a western gentleman wants to get himself into lingerie cut for an Asian lady he will need to add on multiple sizes. This is really important and can lead to health issues if you intend to spend the whole day and/or night wearing underwear that is too tight for you. In addition to circulatory problems you will probably find you have cramps and back/shoulder aches you never experienced before. I will cover textile related health issues (like allergies) in another blog.

The potential problems multiply if a man wants to find a suitable bra. I have found an international guide for cross-dressers which might be useful – the link to a copy is here tips for gentlemen when sizing bras from transformates dot com.

11 Sizing the bra needs care see the embedded PDF chart for some tips

I do not want to over state the problems in acquiring trans underwear – my main objective here is to help starters avoid some of the early pitfalls. Sometimes a bit of trial and error as you develop a new Trans wardrobe can add to the fun. So don’t let the teething problems put you off – the benefits far outweigh the challenges.

With this article I have shared some photos to highlight different styles and to demonstrate that this is something that many men already do. You do not have to be a full 100% cross-dresser to enjoy the pleasures of wearing nice lingerie. In fact some men do not find themselves suited to wearing a dress or a skirt but feel fully ‘at home’ wearing ladies underwear beneath their normal ‘male’ attire (as do many ladies who wear men’s undies – a subject for another day).

How about a bit of musical entertainment to finish off this article. This video is dedicated to our latest follower. Remember some people may find what you do is freeky – but I LIKE YOU A LOT!

I hope this has been informative and interesting. If you agree please visit the blog again (and of course followers are always welcome).

Pretty Boy Sally

Hiding Your Panties at Work 12: Sometimes a ‘little’ hole can add to the fun!


2 thoughts on “Hiding Your Lingerie At Work – The Discreet Trans Gentleman”

    1. Thanks for the link Suzy – although transformates.com is not a commercial site I have included your suggestion because I think readers may find the sizing tables useful. The comments from male customers were also informative.
      All the best,
      Pretty Boy Sally

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.