7 Things You Learn As A Straight Guy Who's A Crossdresser

7 Tucking Your Junk Is A Delicate Art Form

Let's get this out of the way. Any time a male sees another guy wearing, say, Beyonce's outfit from the "Single Ladies" video, he has one question: "What does he do with his balls?"

Well, as a crossdresser, I have to tuck my junk regardless of whether I'm wearing a skirt or pants or whatever, because part of feeling feminine is not feeling my penis bump into things. It's not simply a matter of cramming it back between your legs, either. The biggest problem isn't my massive pendulous man sausage (hey, it's my story and I'll tell it how I like); it's those delicate testicles.

You can't squeeze your balls between your thighs, because ouch. Instead, you've got to put them back in where they were before they dropped: That cavity in your lower abdomen that they used to be in is still there, and you can push them right back up. An empty scrotum is much easier to tuck away, and once it's tucked, your balls won't drop back down, because you've squished your sack between your thighs and there's no empty space for them to drop down into.

Now, that means I can't use basic women's underwear, because the elastic isn't strong enough and your tuck will pop loose and hang out like the stem on a pickle. So I use a gaff, which is like a thong, but made with stronger elastic to keep that shit pressed hard against my body and not jiggling free for a breath of fresh air.

So why do I go through all of that? Not for the reasons most people think. First of all ...

6 Sometimes Sex (In Either Sense) Has Nothing To Do With It

I know I started cross-dressing as early as age three, because there are photos of me in a tutu, though memory of that is fuzzy at best. But it really started right around the cusp of puberty. Sometimes I would be home alone after school while my mother was at work, and I would try things of hers on and look in the mirror. I didn't have any body hair at that point, and I would imagine that I was looking at a girl. I don't know when I started actually seeing myself as that girl, but over time, that's what happened.

Now, when people see a man dressed as a woman, they make one of two assumptions (well, really they make one of three assumptions, but I don't feel like addressing the "AHHH! It's the depraved spawn of Satan! Kill it before it corrupts the children!" folks right now): that you're a trans woman or that it's some kind of kinky sex thing. There are plenty of crossdressers in both of those categories, but there are plenty more who are like me -- I'm perfectly comfortable in my male skin, but also have a distinctly feminine side of myself that I feel the need to express. And that doesn't compute for most folks.

I don't spend my time at work antsy and uncomfortable at the fact that I'm dressed as a man. Nor does the thought of putting on pantyhose give me a lady boner (which I suppose in my case would be a garden-variety boner, but whatever). It's about getting to bring out my feminine side every now and then. Part of where it gets weird, even for the dressers ourselves, is learning to differentiate between something feeling sexy and it being sexual. I can put on all this stuff (and it's a lot of stuff, we'll get into that in a moment) and feel incredibly sexy, but it doesn't get me off. It may seem like a fine line, but really, it's the same way that any woman can put on a slinky dress and heels and feel powerfully sexy, but that doesn't mean it gives her a sexual thrill in and of itself. It's a look, not a fetish.

And yet I still face a metric fuckton of pressure to make it about sex, especially in online communities. In my experience, pretty much every large community of note has a dating site aspect to it somewhere. In this case, men who fetishize crossdressers use such sites to go about finding crossdressers willing to fuck them. Even if I put in my profile that I have no interest in hooking up or that I'm married, I still get inundated. These men -- and it's always men -- think that you're just a submissive, and that if they can show enough dominance, they can strong-arm you into doing what they want.

The disturbing thing is that in a lot of cases, it works -- especially with dressers who are starting out or are closeted. What most of us want more than anything is validation of our femininity. Unfortunately, the easiest way to get that, the sort of crack cocaine version of it, is to appeal to men who will sexualize you like some kind of feminized fucktoy. And even that kind of acknowledgement feeds the need for approval on some level, meaning that many crossdressers, even if they're attracted to women, have stories of agreeing to do something with a man (online or in person) that they wouldn't have otherwise done.

The validation that you are feminine and you are enticing is a big pull for most of us, and if we're not getting it from friends, family, or healthy relationships, it's easy to slip into getting it from wherever you can.

5 It's An Incredible Amount Of Work

It's true that not all crossdressers go all out. Some will just wear women's underwear or pantyhose under their suits and go about their days. Others might put on dresses but not do makeup. For folks who are closeted in some fashion, dressing tends to only be a partial thing. This is especially true for those either still living with family or roommates who don't know, or (more complicatedly) have spouses who don't know. They'll put on what they can when they can, but it tends to be a smattering of small items that they can easily hide in a box marked "FREAKY ASS PORN -- SERIOUSLY, DON'T OPEN THIS." As for me, I'm an all or nothing kind of girl. I'll do the full hair and makeup and clothes or I won't do anything at all.

I generally know when I'm going to dress (at a trans-friendly event, burlesque shows, that sort of thing), so I'll do body hair removal the day before. For most guys, this is virgin territory, but I'm sure any women reading this is thinking "Yeah, I know all about this." Hate to break it to you ladies, but not like this you don't. Do you know how much Nair it takes to leave Bigfoot silky smooth? Of course, there's multiple ways to get rid of the mess, and frequently I will just shave, which in my case means legs and chest and pits (plus tweezers between the eyebrows to eliminate any stragglers that might hint at a unibrow).

I'm fortunate in that I don't really have to do anything to my arms -- I have very minimal, light-colored hair. I also don't have to do anything to my back. There are crossdressers who are Robin Williams levels of hairy, and I thank my pink twinkling stars that isn't me. I have tried everything: epilators, creams, even professional waxing a couple of times (which is my favorite, but expensive; also I have to drive two hours to find a waxer who will even touch somebody with dangly sex bits).

Face-shaving is separate from the body shave, you have to do that pretty much right before you do your makeup to minimize beard shadow. You can forget those fancy light powder makeups that the rich folks use; you need a liquid foundation, and then when you put a powder over that, you have to use a compact concealer. Start dabbling with translucent stuff and that's when your stubble shows through.

Next, you'll find out that ...

4 Women's Clothes Aren't Made To Fit Dudes

OK, your unwanted hair is gone, so now you pick your outfit. Undergarments are a bra to hold in the breast forms (i.e. the fake silicone or foam tits we keep in a box marked "TRAUMATIC CHILDHOOD MEMORIES -- DON'T GO POKING THROUGH HERE!") and the aforementioned thong to keep my tuck from escaping. I also have a variety of wigs, so another aspect of putting together an outfit is deciding which hair is going to go with it. So now you can add wig maintenance to your to-do list -- the brushing and washing and trying to get it back into the style it was when you bought the stupid thing.

And then there is the confusing labyrinth that is women's clothing sizes. If you're a guy shopping for men's clothes, you know that no matter where you go, no matter what brand, you're probably the same pants size. Shirts are S, M, L, and XL. With women's clothes, it's a crapshoot at best -- I wear anything from an eight to a 14, depending on the brand. Oh, and you have to do all of this experimenting at home if you're not "out" with your crossdressing. Otherwise, you're risking a coworker seeing you head into the Gap dressing room with an armload of miniskirts. So each misfire means a trip back to the store.

And we haven't even mentioned the biggest issue, which is that men are shaped differently -- we tend not to have those curvy hips and waists. So already I'm trying to pick clothes based on my size-D breast forms, and then, because women's clothes are designed on the assumption that you have at least some level of hips, I need a corset. You've got to get one with steel boning (and no, that's not the name of the Iron Giant porn parody); most cheaper corsets use plastic, which will warp and fall out of shape almost immediately. With tops, I stick with mostly sleeveless or short sleeves, because long sleeves end up only going halfway between my elbow and wrist -- guys have longer arms.

As for shoes, at least the sizes are consistent ... but then you have to learn how to walk in them without falling on your ass. That takes practice, which of course is the one thing the closeted crossdressers with roommates or spouses never get the chance to do. Which brings us to how ...

3 Relationships Can Be Complicated

This one can almost go without saying, but man it's a doozy. If you're going to have a long-term relationship, the inevitable questions come up: "Do I tell her?" "When do I tell her?" "What if she rejects me?" "Could I stop if she asked me to?" Remember, this isn't just something done as a fashion statement, like if your significant other asked you to throw out your "Free Mustache Rides" baseball cap. With crossdressers, it's a key part of their identity.

You get double complication points if you start to get a handle on this side of yourself after you're already in a committed relationship. Rejection, or even the fear of it, leads to a depressing cycle of wardrobe purging for many dressers, when they throw out all their makeup and dresses at the insistence of a spouse, or out of fear they'll find out. But if you truly have the need to express your feminine side, that doesn't go away. And then it leads to not only being in the closet, but dressing behind somebody's back, which is a breach of trust on top of everything else.

I am insanely lucky because my wife has been wonderfully supportive. I know I'm lucky, because there are a million horror stories about dressers coming out to their wives or girlfriends with disastrous results. In many cases, it's not the dressing itself that throws everything out of whack; it's the secrets and the sense that the dresser was keeping something from them.

As for me and my wife: We dated in college and at the time I had a dorm room to myself. The room was a disaster, as is typical in that situation, so one day when she was there without me, she made the heroic attempt to try to pick up a bit. She came across a pair of women's pantyhose, and when I got back she confronted me with them. "Whose are these??"

I paused, and then, figuring I had nothing to lose, said, "Those are mine."

She only said, "Oh. Well that's okay then."

See? Lucky fucker, that's me. We actually didn't talk about it directly for a long time -- she just kind of got it. It was a while before we sat down and had conversations about it. By then most of it had to do with sort of figuring out how much of my life I wanted this to be. I started asking, "Is this something I want for my life? Do I want to transition?" I suspect most part-time dressers go through this questioning phase, and so that was sort of why we started talking about it more directly. Finding the balance that I now enjoy came out of much soul searching and many conversations. But even then ...

2 You Don't Really Fit In Anywhere

The thing about being a straight crossdresser is that, on top of not really fitting into mainstream society, you don't really fit into the LGBT community either. Gay men tend to get annoyed and believe we don't know what their struggle is like, bisexuals seem to find it confusing because many assume mixing genders would mean liking both. The trans part of the LGBT equation is where you'd think crossdressers would fit in, but there's a lot of infighting in that group which is kind of hard to sum up. Let me put it this way: I'm a crossdresser who has no issues putting myself out there on the interwebs or strutting about in public from time to time, but to date, the most hostility I've encountered has not been from the homophobic fuckwits you'd expect, but from trans women.

Obviously not all of them are hostile, but I think that many of them have a violent gag reflex at the thought of being associated with someone who is "just" a man in a dress. They've obviously been through plenty of shit to get to live as the women they feel they are, and I get not wanting to be belittled by some dude who they see as doing it for fun or attention. And even they tend to make the assumption we talked about earlier -- that if you're not gay or transitioning, then it must be a sexual kink. Online (where everybody feels safe to throw shit) I've been told flat out, "You're not even transgender, so stop acting like a woman," as if there's some sort of entrance fee on femininity that I'm trying to skimp out on.

I mentioned that I perform in burlesque shows. I haven't performed in a drag show for years, because they're bitchy and cliquey and I hate the drama (yes, somehow Rupaul's Drag Race winds up being an accurate portrayal of reality). So since I wasn't doing the big hair, ball gown, lip sync to Donna Summer thing, I found myself getting more than a few sideways glances. And those turned into not-very-hushed whispers once word got around that I was straight.

Where I've found the most acceptance is with lesbians and drag kings, and I couldn't really tell you why, but also with the burlesque community, because they're kind of "all are welcome" by their very nature. But no matter where I go, I have to deal with the fact that ...

1 Pop Culture Has Confused Everyone

I mentioned that there's a period of confusion for most dressers, and part of the reason for that is there aren't really any cultural reference points for this. There's Eddie Izzard, but he really only does his stand-up specials in dress these days. Now he does a lot of acting work where he's wearing boys clothes and interviews where he's sporting a goatee, so even that one purported pillar is kind of a shaky one. Really, the main place where you see crossdressing is in shitty comedies: Big Mama's House, Sorority Boys, White Chicks and the like. That's why I think it throws people off. The pop culture point of reference for a man in a dress who isn't transitioning is a dumb gag in which a guy is forced to wear a dress by circumstance so it can be played it for laughs (hardy fucking har).

So I went through years trying to convince myself that I wanted to live as a woman, even though I'd never felt wrong in my male skin. It also took quite a while to come to an understanding that dressing to feel sexy didn't make dressing sexual. Since my only frame of reference was bad jokes or sexual fetishes or gay men, I thought "Well I must be at least bisexual," so I spent a lot of time trying to fit a square peg in a round hole before finally being able to separate sexual orientation from gender identity.

Ultimately, I occupy a weird little spot in between so many of the more clearly defined designations for gender, sexuality, etc. The funny thing is, I've grown to like it here. In an odd way, being hard to categorize has made me feel a little bit more special. It forces people to have to examine me a little closer if they want to ever understand me. Plus it makes close-minded people's heads explode like fucking Scanners, and that never gets old.

For more insider perspectives, check out 5 Shocking Realities of Being Transgender the Media Ignores and 6 Awful Lessons I Learned Transitioning from Female to Male.

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