Thursday, August 20, 2015

8-20-2015 Entry: Let's Talk About Underwear

my darlings! It is I, the great and magnificent Oz… er… I mean Emma. Okay, I’m feeling a bit playful today, can you tell? I can attest that a vast majority of my playfulness is a result of my recent experience of reestablishing my World of Warcraft addiction for the first time in about 4 or 5 years, but overall I’m feeling better about life than I have been in recent weeks.

I suspect that my Saturn return easing past its natal position probably has something to do with it as well but generally speaking life has become more bearable. I am still unable to write blog entries during the time I was for many months, but I’m finding ways around that blockage. I know, it’s all so mysterious and vague. Well, probably not really, but for the sake of keeping things on the up and up I cannot explicitly explain what I mean. You know, plausible deniability and all.

So today’s entry is going to be a bit more exciting than some of my recent ones, at least I’m hoping it will be. Today, my darlings, I want to talk about the unmentionables. That’s right, we are going to chat about underwear, and what it is like as a transwoman who has not had SRS to live her life in lady skivvies.

So, before we begin I suppose some background is probably in order. Robert was never one to care much about his underwear. He had a specific kind that he eventually settled on and beyond just the type, there was never much thought given beyond that. In fact, almost 99% of the underwear he had, even into his twenties, had been purchased for him by his mother and grandmother for Christmas. Funny how as a child you dread getting things like that for Christmas, but as a young adult you are like, “OMG YES!! I can finally throw away these hole-ridden underwear I’ve been shame-wearing for the last 3 months! The chafing is finally at an end!! Thank you, Grandma!!!”

Basically, Robert eventually settled on boxer briefs as his preferred method of boy-bits-covering and that was for a couple reasons. First and foremost, it offered the greatest protection against chafing, something that became all the more important when he gained 100+ pounds over the span of about 7 years. The second reason was that they were generally more innocuous when it came to lady seducing time than say, batman themed boxers, or heaven forbid, tighty-whiteys. The final reason was that they were easy to comfortably lounge in when no one was around because they basically looked/felt like shorts.

Notice, my lovelies, that Robert didn’t think about fashion at all because, let’s face it, boxer briefs are relatively unimaginative in their construction or coloring. He never sought out expensive versions of his underwear either, usually sufficing with good ol’ Hanes or Fruit of the Loom. He also didn’t think anything at all about the way the underwear looked on him. They covered up the bits, fought against chafing, and that was all that was needed.

So, you can probably imagine that walking into the women’s underwear section at the store was a bit like stumbling into wonderland when we finally decided it was time for us to transition genders. Women’s underwear, is sooooo different than men’s underwear. First, and foremost, women’s underwear usually comes in singular form (although not always) when men’s underwear basically always came in a plastic multi-pack bag (unless you were buying the afore-mentioned super-hero themed boxers, that is).

Women’s underwear also comes in more varieties than men’s underwear. Men basically just have boxers, briefs, and tighty-whities. Women have boy shorts, thongs, no-line undies, granny panties (I don’t know what else to call them, sorry), and like 10,000 different kinds of lacey lingerie-type underwear. I mean, there are entire stores, physical and online, practically dedicated to the varieties of women’s under garments (Victoria Secret to name one). You don’t see a store called Albert’s Secret dedicated solely to men’s underwear, do you? If that doesn’t indicate how drastically different the two worlds are for you, I’m not sure what will.

In addition to the increased variety of underwear, there is also an entirely additional component to lady-dom that men don’t have to worry about, their chests. I’m talking about bras, of course, and they are almost as numerous, if not more numerous, in variety and fashion than underwear is! There are push up bras, convertible bras, adhesive bras, demi bras, front closure bras, full support bras, maternity bras, minimizer bras, padded bras, racerback bras, and the list goes on and on (check out this site if you don’t believe me )

Are you starting to miss the simplicity of a multi-pack of boxer briefs yet? I know I certainly am, although despite the increased stress of trying to find not only the kinds of underwear I like but the kinds that will actually fit me functionally, this jaunt into women’s underwear wonderland has been rather exciting.

It’s somewhat like you’ve only ever eaten oatmeal for food your entire life. Sure, you can have a variety of oatmeal like peach oatmeal, blueberry oatmeal, thick cut oatmeal or just plain oatmeal (aka whity-tighties if that wasn’t clear), but it’s still just boring ass oatmeal. One kind often blends into another in a forgettable line of meals. Going to women’s underwear is like going from that boring, relatively unimaginative diet of oatmeal, to arriving at a fancy banquet-style buffet. No, I’m not talking about Golden Corral, I mean like a fancy hotel in Vegas where the price of admission to the buffet is like $35 a head. There’s filet mignon, unlimited crab, lobster tail, and on and on. The kind of buffet that is actually memorable (like the one my wife and I had at our wedding, which was SOOO good)

I do not remember ANY of the underwear I wore 3 years ago… like literally none of them. Sure, I have a vague idea of what they might have looked like because they were just like the ones that came before and after, but overall they were hardly memorable at all. I now have underwear I’m certain I won’t forget for a long time because I picked each one out specifically and almost all of them are different. Some of them are so much more exciting than any of the boxer briefs I had, what with the neat colors and interesting patterns.

I have found, in my experience, that it is much more permissible for a woman to wear multi-colored underwear than it ever was as a man. Even the most basic of day-to-day underwear can be both unique in design/color and even sexy (if that’s what you are going for). Boxer briefs, at least to me, were almost never “sexy” to wear or be seen in. Tighty-whities are absolutely the opposite of sexy. Batman boxers, while neat, are definitely not sexy. The simple, black, boy-shorts I have on right now, definitely have the potential to be sexy.

Anyways, there is obviously somewhat of an elephant in the room when we discuss women’s underwear as a transwoman. Women’s underwear is not designed to comfortably fit or encase, boy bits. Early in transition, with relatively miniscule breasts, wearing a bra can also be a bit tricky. So what to do? Yes, we’ve arrived at the meat of this entry, the practicalities of wearing women’s underwear as an early transition, pre-SRS non-binary transwoman!

Okay, so what are the main concerns when approaching women’s underwear as an early transition, pre-operative transwoman? What are concerns that might not be so obvious at first but are really important? And lastly, why do it at all? Why not just wear men’s underwear still?

First, the main concerns. Obviously, comfort is a key concern. You might feel sexy in your new underwear, but are you going to be comfortable in them for what you are doing? Do you wear the same underwear out on the town as you do for 8 hours at work? If so, are they going to itch, pinch, pull, squeeze, or chafe in a way that won’t be bearable? Depending on the size of your bits, which will likely shrink some with HRT, this can be something rather easy to overcome, or can be a big problem… literally.

Because women’s underwear isn’t designed to fit and snuggle up nicely to a penis and scrotum, chances are, most of the underwear isn’t going to fit the way you’d like. There are way around this, which we will discuss in a moment.

The next concern is how does the underwear display what you have going on downstairs? Does it look like a banana hammock or does it minimize your bits? If you are anything like me, you want the second of the two, especially with certain types of clothing, but is the underwear alone enough to minimize what you have going on?

Some dresses, skirts, pants, and shorts are really amazing at showing the entire world that you have a bulge downstairs, which if you weren’t aware, is a HUGE giveaway that you are transgender (guys like to check girls out, from head to toe, including hips/crotch area, so it is noticeable). If passing is something you are concerned with, you cannot have a bulge in public.

Some clothes + underwear combinations can go so far as to actually display, rather revealingly, the specific features of what’s going on downstairs. I am wearing a maxi skirt right now that does this exact thing. If I don’t make proper underwear decisions, everyone can see not only a bulge, but the actual outline of the penis. Imagine how mortifying that was to discover after buying the skirt.

So, what to do? How does one fix this issue? A lot of you, I’m sure, have heard about tucking. Essentially, it’s where you tuck everything under so that it has a rather smooth, vagina like appearance to it. There are a lot of ways to do this, some more painful and honestly barbaric in my opinion than others. The big one you will hear about is using tape. Yes, that’s right, people are out there right now, strapping down their penis and balls with tape (duct tape, packing tape, etc.) to make it look like they don’t have them.

I commend people who have the pain tolerance to do that because I am not one of them. I haven’t even tried it, honestly, because I’ve seen videos about how to do it and it is not pretty. It looks more like a form of self-torture than anything, but I understand if that’s the route people feel they need to go. I do not judge them, I only implore them to be careful.

The next way you will hear about tucking is through the use of a gaff. This is basically some sort of clothing or device by which you tuck everything in nice and tight without the use of tape. I have seen a lot of ways to do this, but my personal favorite was offered by one of my favorite youtubers, Violet, which can be seen here ( ) you basically take a long stretchy hair band, the tube of a tube sock, and fashion something rather similar to a jock strap, except instead of encasing your junk to protect it, you tuck it in rather tightly.

I liked this method because it was quite effective and relatively easy to fashion, but the problem with it is that it doesn’t really work if you have a larger waistline, which I do. It’s also rather uncomfortable for long periods of time (like sitting in a chair all day at work) so it’s best used for short-term wear, at least in my opinion.

There is a third way of tucking that I, myself, have discovered which is rather effective and easy to achieve. I actually discovered this method by accident when I was trying on swim suits at old navy. I tried on a one piece, which I liked, but it revealed terrible things about my legs that I wanted to hide. I decided to also put on one of those skirt-like bottoms to cover up the scary parts. Upon looking in the mirror with three layers of, essentially, underwear on (my underwear, and two swim suit bottoms), I realized that you couldn’t tell I had boy parts at all. My wife even confirmed for me that it didn’t look like I had a penis at all, and the best part was that it wasn’t all that uncomfortable. It was a little snug, sure, but not unbearable.

I took this discovery home with me and decided to try to replicate the effect. I have found that boy shorts are my favorite kind of women’s underwear so far because they most adequately encase my boy bits (also they weren’t a huge jump from boxer briefs which made the adjustment easy). I have several pairs of them, so I decided to put on more than one pair. I began with just two pairs and what would you know, they almost completely tucked my bits in a way that you couldn’t tell they were there. One pair is usually enough to reduce the visibility for less revealing bottoms, but two pairs is almost as effective as wearing a gaff. The best part is that it is actually comfortable; snug, sure, but comfortably so.

So, for me, the problem of that bulge has been solved by wearing multiple pairs of snug-fitting boy shorts under my more revealing articles (like the maxi skirt I have on), but what about bras? How does one pick the right kind of bra for early transition breasts?

Again, the size of my body limited the kinds of bras I could get. I happen to have a very large torso with some added fat (because I still need to lose weight) so most bras at a regular store aren’t long enough around to fit me. I forget the size I had to get but I ordered one of the largest lengths available from Torrid (big and tall lady story) and still had to buy an extender (ProTip, those can be found at craft stores like JoAnne’s fabric in case you need two or three inches on your bra circumference).

So, what did I land on? Well I bought two two-in-one bras that can be worn as strapped or strapless. At first I wore the straps on them but I hated how often they were falling down my shoulders, so I have been wearing them strapless for the last month or so. I do have to occasionally hike them back up as they can slide down your chest/back, but generally they fit pretty well, so I don’t have to do that very often.

Obviously, things are still rather small upstairs, so rather than trying to find a padded bra that fit me, I got slightly larger cup sizes (a B and a C) and just pad them with folded socks to even things out a bit. Most of my tops are not all that revealing so usually no one can see the socks, but if you like to wear revealing tops, this solution may not work for you. You may want to seek out a padded bra at first, but I leave that up to you to decide. Stuffing is definitely a bit inglorious, but it’s a means to a temporary end.

The last thing is lingerie, which I honestly haven’t even begun to experiment with. I suspect that is something I may hold off on until I can have SRS and can actually wear the lingerie the way it is meant to be. That’s maybe just me, but it feels silly to put that stuff on when my body soooo isn’t in the right place for it. Sex drive has been an issue lately, in no small part because of my body not matching what I want it to be, so showcasing it with expensive lingerie isn’t my idea of a good time. Again, no judgment to others who do want to experiment with it, I hope you find what you are looking for with it.

As a final side note, I do want to say that I still own and regularly wear the men’s boxer briefs I have. I usually wear them after I get home or when I sleep at night because they are a bit more comfortable. Plus, it is really important for your boy bits to have some air to breath. It prevents infections and other nasty things that are miserable to contract (I’m guessing, since I haven’t had that problem). I don’t love the way I look in those but when I’m at home wearing jammies, I don’t really mind.

 I do, however, find a particularly enduring sense of excitement and joy when everything is tucked away under my boy shorts and I look like I have female bits. It just feels right. It just feels like that’s the way it is supposed to be and that’s why I do it. More than fashion or due to gender roles, I wear women’s underwear because it makes me feel happy and comfortable in my body. When I’m in nothing but my skivvies (bra/underwear) and look so much like a girl, I feel at home. It just puts a smile on my face. Plus I’m dead sexy! >;)

Well, my darlings, that’s all I have for today. Thanks for stopping by and reading up on the unmentionables. If anyone has anything to add please feel free to leave a comment or send me an email

With love,


No comments:

Post a Comment