I am settling into me. Some days I dress a little butch, while other days I femme it up a bit. Always I wear men’s underwear, except of course when I wear no underwear at all, which is what happens when I wear workout clothes. I remember when I started wearing men’s underwear. I experimented with different styles. I struggled a bit with boxer briefs riding up under loose pants. A few things have changed since then. My body size has changed. Actually I have lost about 40 pounds so my shape in general is different. Besides that, the more I am who I am, the more I shop for what I want to shop for, the more I wear what I want to wear, the more I change at the gym, etc., the more comfortable I am with myself in general.

I have found that when I am wearing loose men’s jeans, or any loose jeans for that matter, I prefer loose knit boxers. It feels like soft pajama clothes lining the crotch of my pants. When I’m wearing tighter jeans, I like to wear boxer briefs. I found that I prefer the longest leg boxer briefs I can find. I find the longer the leg the less they ride up my inner thighs. Sometimes I still wear women’s jeans. I wear boxer briefs with these too. Sometimes for job interviews I might even wear women’s office pants. I wear boxer briefs with these too.

I have always derived a secret satisfaction from feeling sexy in my underwear even if nobody else is going to see them. I dressed like a straight woman for a few years. I’m not sure how else to describe it. There was a while when I wore men’s clothes mostly because I was larger and they didn’t feel so tight on my belly.  At some point I lost some weight and could wear women’s clothes that were smaller than the plus size section and I felt sexier. Suddenly I wanted to wear jeans that fit my body more closely and I didn’t feel as much like hiding my belly. At the time I was noticing more attention from men.  I let this attention prop up my self-esteem a bit. I was actually going through a stage in my sexuality where I was reclaiming control over my body in sexual experiences with men. I was casually dating multiple men concurrently with full disclosure, playing the field, if you will. At the time I identified as bisexual, but was still very new to dating women. It was easier to keep dating the men that continued to pay attention to me. I wore thongs. Tiny little gauzy string bikinis. Sometimes these would be seen by various lovers. Or not. Even thinking about the panties I wore turns me on a little bit right now. Those tiny little gauzy things tight around my girl parts. It makes me flex a little.  Whenever I found myself in an individual public bathroom I would check myself out in the mirror, undoing my pants to show my  panties. These days I feel similarly sexy in my boxer briefs. I like being seen in them. I also like seeing myself in them. I like seeing myself in the bathroom mirror at work unzipping my women’s jeans to reveal my Express boxer briefs.

As I have been going through my genderqueer butch puberty, I have gradually transitioned to wearing men’s underwear for the most part.  Last summer I remember looking longingly at the underwear in the men’s section at Target, nearly buying some boxer briefs that looked so comfortable, but then not, because the “package” would be empty.  I then wandered back over into the women’s section and bought some little “boyshort” style women’s underwear, which fit nice and snugly (albeit a little too snugly for my tastes lately).

At the end of the summer I was dating a wonderful person with some similar transmasculine leanings who encouraged me to go right ahead and buy the men’s underwear if that’s what I wanted.  It didn’t matter whether or not there was some extra fabric around the crotch.  I didn’t have to fill it out to deserve to wear it. (Or I could fill the package….wow…an even more exciting concept I had not let myself dare to dream at that point).

So, to make a long story short (boy shorts), or at least get closer to the point, I started buying men’s underwear.  I may have snuck some into my cart at Target, bought some along with vacuum cleaner bags at Sears, and even tried some on at Marshalls.  I’ve tried out a few different shapes, to include boxer briefs and knit boxers, and have explored a variety of brands and sizes.  I’ve played around with the gender intentions of the clothes I wear for work and for play, as well as with my hair, jewelry, makeup, etc.

As I let myself explore more sections of clothing stores, sometimes filling my cart up completely with clothes from the men’s sections and then traversing the store to try them on in the women’s dressing room (Oh the irony…I love H&M for having gender neutral dressing rooms) my men’s underwear drawer filled up, and my women’s underwear drawer was opened far less often.  Depending on where I am or who I am with (friends, lovers, etc.) I have noticed new comforts as well as discomforts with my new underwearshape choices.  When spending the night at a friend’s place, or sharing a hotel room with friends, I’ve found boxer briefs to be much more comfortable and convenient for casually sleeping and hanging out.  Less revealing than women’s panties, they feel appropriate to wear in lieu of pajamas if need be, and far more concealing for prancing off to the bathroom without a robe.  With a new lover this fall, I felt a little more self conscious, wondering, does she think these are sexy?  Do they turn her on?  Why does she take them off with my pants?  What does she think when I am getting dressed in the morning?

And then there’s the gym.  I’ll have to say, I don’t go there that often, not because I’m not sporty, but because there are many other active things I like to do that are far more exhilarating, fulfilling, and enjoyable for me, so the gym is sort of a last resort for me in the exercise department.  Like buying from the supermarket what I would have rather found at a farmstand.  But I digress.  The locker room was what I was getting at. I wasn’t prepared for how I would feel when I got to the locker room for the first time and realized I was wearing men’s underwear.  Not really prepared at all.  In addition, I have let my body hair grow out this fall as well, which brings another level of insecurities for me in occasional situations (though these I have encountered before as I have had my hairs every which way at some point in my life, going through hippy phases and the like).

So there I was at the gym one day in my office wear, which recently mostly consists of business casual pants (usually of some women’s size), a collared button down shirt (usually, but not always, of a men’s style), and underneath it all, knit boxers or boxer briefs.  I usually love the locker room situation.  I love being naked, and I love seeing women naked.  What a lucky lucky place to be, as long as I can keep from letting anyone think I might be ogling.  I hope no one notices when I occasionally have to smile to myself after tasty glimpses of breast and thigh….

And there I go digressing once again.  Sorry.  What I am trying to say is that the first time I caught myself in a women’s locker room with my pants down, suddenly revealing men’s underwear to a room full of ladies, I felt seriously self conscious.  What were people thinking?  Did they even really notice, especially if they weren’t oglers like me?  Would I be judged?  Was this weird?  How many other women actually wear men’s underwear?  I hadn’t ever seen it in a women’s locker room before.

I think the first time I took them off really fast.  Better to be naked than caught in boxer briefs.  My bush was more gender appropriate for that room if anyone was judging anyway, right?  The next time, I think I thought ahead just long enough to decide to pull them off with my pants.  The same self consciousness arose on the occasions that I showered and redressed into street clothes at the gym, or even worse, at the locker room at work.  I pretty much just pulled them on and then the pants right after really fast.  It was really the best I could do.

But then today, I noticed myself do something else.  Well, I think I noticed when I noticed someone notice me.  I was with a friend, post shower, getting dressed in the women’s locker room at the gym.  I had one of my favorite pairs of boxer briefs, my favorite jeans (men’s Lucky brand) a bra, a black tank top, a men’s thermal, and a cozy stylish men’s hoodie to put on.  I feel so much more comfortable in the casual clothes that I wear outside of work than those I feel I must wear to conform to the “business casual” standard at the office.  I pulled on my boxer briefs, in no particular hurry, and with absolutely no self consciousness…until a girl across the room looked up at me for just a little too long.  The way women look at me just a little too long in the women’s bathroom in my office building since I cut my hair short and have been wearing more masculine clothes.  Her look, not exactly a double take, but sort of an extra long glance, made me instantly self conscious.  I knew that she was looking at my grey and black striped boxer briefs, with the nice loose package in the front, the piss hole for the penis I don’t have.  I really have no idea what she was thinking, nor confirmation that she really was thinking anything I was self conscious about.  And then I proceeded to get dressed and be on my way, in no particular hurry.

I’m glad to realize that for once I didn’t feel self conscious, even for just a moment, about my butch underpants at the gym :)

Exploration of underwearshapes is one of my favorite ways to find comfort with and grow into my gender identity.  Sometimes, back in my baggy messy sloppy ripped up clay and paint splattered art school days, I took pleasure knowing just how very sexy my tiny little bejeweled thong might be.

That was awhile ago.  Went right through and out the other side of that thong phase.  Well, at least on my body.  I still like the looks of them on someone else;)

In any case, my more recent forays into new underwearshapes have been into boxerbriefs.  And not just the women’s boyshort version (though they were certainly a gateway underwearshape).  I mean the package worthy real deal.  I have shopped in and out of the men’s department for a variety of items my entire life.  In high school, and perhaps before that, men’s boxers were the thing to wear in the dorm, and even out and about as summer shorts, if I seem to remember correctly.  The men’s department has always had cheaper T shirts; the white V neck variety has been a staple in my wardrobe on and off.  I have big feet anyway, usually in men’s boots, and a package of men’s white socks is another staple.  In the past few months to a year, I noticed how inexpensive and comfy men’s department pajama shorts are.  At about that time that I started buying the men’s pajama shorts (it’s always a great excuse to use “pajamas” as the reason to buy something I may not be able to wear out in the world yet), I started more seriously looking at men’s boxer briefs.  On one particular occasion I was just about to buy them but worried about all the extra material around the package that I didn’t have.  And I picked the womens version, that would wrap right up tight there around my female business.  I bought some playboy cotton jersey boxers on the sale rack at Marshalls and loved wearing them to bed.  I liked the girl shorts, but they were too hot in summer and they kind of rode up in the middle.

Somewhere in the middle of this process I started dating a wonderful human being who got right into this underwearshape discussion with me.  My cousin thought she looked like a man.  I found her extremely attractive perhaps because she was a woman that embodied a beautiful masculinity.  But I digress.  She moved to another city and broke my heart a little, but really encouraged me to be a little more of who I am, and I am eternally grateful for that.  She actually pointed out to me one day that there was a big butch inside of me waiting to come out.  I don’t know exactly how she could see that so clearly and just say it to me like that like noone else before ever did, but I’m glad she did.  We never did get to go underwear shopping together (did I mentioned she cracked my heart just a little by moving away and on), but as I said, we discussed our comfort levels and attraction to a variety of underwearshapes.  She looked so good in the pastel men’s underwear she wore occasionally.  She encouraged me to go ahead and buy the underwearshapes I wanted not just even if but just because they had a package.

And so it began.  A foray into exploring more men’s underwearshapes.  From Express to the Gap, to Hanes at Sears, and Calvin Kleins and Body Glove at Marshalls.  I’ve found that just like women’s clothing, the sizes vary among brands.  I want them to be the perfect new underwearshape for me, but they might not be all the time.  I found some gently loose cotton jersey boxers at the Gap that feel perfect with a certain pair of jeans.  I found a pair of extra long DMK boxerbriefs, that feel great under some feminine office pants.  My butt’s a bit round though, and so are my thighs, so sometime the legs of boxer briefs ride up in the crotch, except for the extra longs which don’t quite cover my butt crack.  I work in an office, where a far-from-any-metropolitan-area version of business casual is the dress.  For a while I had been playing dress up, with skirts and boots, capris and heels.  Somewhere around last summer I gave up on the heels and settled for flip flops. As we deepen through the fall towards winter temps, I have masculinized my dress quite a bit, with shorter and shorter hair cuts.  Little to no eye makeup.  Pants always, and never skirts.  More men’s button down shirts.  I still wear women’s pants, as they fit me better, and occasionally women’s shirts or sweaters.  I usually wear the boxer briefs under everything.  Only sometimes they bunch up somewhere, and I end up taking them off in the ladies room and bringing them back to my cube in my pocket where I sneak them into my backpack.  Then I go commando for the rest of the day.  That really may be my favorite underwearshape.