Welcome To The Working Week

Students are not the only ones who dread the month of September – teachers, too. And there are no exceptions for crossdressing ones. With the 2012-13 entering full swing next week, the frequency of my complete crossdressing will most definitely slow, which is unfortunate – but I’ll just have to make the most of the times I am fully en femme.

Perhaps it was the start of the school year that led my girlfriend to posing the question “If you could go to work fully dressed, would you?”

Before I answer the questions, first I want to analyze the motives of its asking. I believe they could be one of two things:

  1. She asked because she was curious about how involved I would let my crossdressing become in a school environment – specifically – would other teachers ever know, or even students?
  2. It was a broader question judging just how serious I am about crossdressing, and if it would ever become something more.

(Please note, girlfriend who will probably read this, that I felt no ill-will when you initially asked, and likewise I hope that none is felt in reading this.)

I think her actual motives might have been a little bit of both – it is an interesting question and situation, enhanced all the more by the work environment of a school. I also think it was a good question to force me to think about my future in crossdressing, without actually asking that.

Let me say this – I am a crossdresser, and in one sense, I have always been a crossdresser. (Is the act of dressing necessary for one to consider themselves a crossdresser – or is it just the want? I’ll save that question for another day.) In addition, I will always be a crossdresser – even if I stop dressing (and in this I am sure.) I have no plans to ever stop, and see no reason. Why change something about yourself that you like? I was taught never to give into peer pressure – and that will continue, regardless of what my family might think if I tell them, or if in some bizarre unthinkable circumstance my school tries to use it as grounds to fire me. My happiness comes before theirs.

Now, back to the original question – if I could, would I go to work dressed up?

It all depends on the environment at work – if it’s a utopia, and everyone, students and teachers, welcomed it with open arms – sure. I hate wearing a tie and women’s clothing, to me, is more comfortable. There’s also more variety and fashion. Women, at the school where I work, also have the ability to dress for a wider range of weather than men. Yeah, I can wear a polo when I want to dress down, but I’ll never be able to wear “fashionable” sandals to work. Socks and dress shoes all day are uncomfortable.

Outside of this perfect utopia – in the actual world, where I actually work… well that is a different story. Right now, no, absolutely not, I would never go to work crossdressed. I wouldn’t even wear girl’s underwear under my pants in lieu of boxers. There’s too much risk for too little reward. And yes, I have ripped my pants at work. Twice, actually.

I also want to note that I am untenured. Ignoring any debates about what you think of tenure – it would be much easier to fire me if I was “found out” as a crossdresser, and find some other reason to justify it. I think, as educated individuals, most of the administration in my district would support someone who crossdressed, but in a society with a feral news media that often demonizes teachers and high strung parents who are overprotective, having a crossdressing teacher is not a good PR move. Also note, that most people think of crossdressers as deviants, not normal people who enrich their lives with a creative hobby.

Maybe one day, crossdressing will be more widely accepted and I will be able to wear a skirt and panty hose to work. Maybe that day is closer than I think. Recent articles, like this one about German father Nils Pickert and his crossdressing son, or the New York Times piece on “gender-fluid” children are heartening to read and hopefully signal a changing perspective on what it means to be a crossdresser. (One quick nitpick – the NYT article does not once use the word “crossdress” – is this intentional? Some kind of rebranding with a push for acceptance? I don’t know.)

There you have it. Would I crossdress at work? Yes and no. I love dressing up, and would do it more often than not in an ideal world, but it’s not an ideal world, and to be honest the frequency at which I’m dressed right now is more than enough for a crossdresser like me, who was in the closet to everyone just two months ago.

In my next few longer entries I want to do a write up on how the internet influenced me as a young, closeted crossdresser, and  also how Halloween is essentially Christmas for crossdressers.



Convincing? You’ll not notice my hairy arms cropped out. You will notice the bottom of my new wig. It feels great. Soft, flowy…. but it’s also a bit wild, and I don’t care for the way it parts. I’m going to see if my girlfriend can straighten it. I like the look of my synthetic wig better, but this one is clearly higher quality. Alas, like a real head of hair, I’ll have to play around with it.

Shave a Man’s Back, He’ll Purr Like A Walrus

The title of this post is a classic line from Family Guy, and as I learned the other day, true.

The dress I am going to wear for Halloween has a low cut back, which means I cannot use my breast form bra, as the back strap would be plainly visible. To work around this I ordered from ebay a bra with invisible straps and body adhesive, which would require a serious lack of fur.

My girlfriend gave me the okay to shave my chest and back, and with her help I was shorn. Now, I’m quite the hirsute fellow, and this was no easy process. I started by using my electric razor to trim all the hair so that it would be easier to shave. After this I hopped in the shower and shaved the rest. My girlfriend helped with the back, and just like that my loafish body looked like a slippery beached whale.

Having a clean chest after being hair for the past twelve years or so is taking some getting used to. I clearly didn’t do a very good job shaving between my man-boobs, as denoted by the various cuts and bumps now present. The end process, does, however, looks quite good – and the ability to wear any low cut shirt adds to femininity more than I would have guessed.

I’m uploading another photo, with more detail but my face blurred out. If you saw the whole thing, I swear you’d swear I looked almost demure.

Believe in the cleavage

This is how I naturally look.

I should, though, explain the cleave. Using the make-up tutorial located here I was able to create some semblance of boob. I didn’t have all the materials used in the tutorial, but I made due with what was accessible.

Overall, considering it was the first time I’ve attempted art on my chest – I’d say it was a success.

I’m other news, add another to the list of people I’ve told. This one was a bit more daring. A friend of mine who is quite liberal in talk, but still acts conservative when presented with some real-life situations.

Initially he did not believe me – he thought I was pulling some sort of massive joke. I showed him some pictures, and he still wasn’t sure if he was being punk’d. It took another friend, who knew, to confirm to him the truth.

He is okay with everything, but was definitely weirded out. He said it is hard to learn something so new and important about someone you’ve known for so long. I suppose that’s fair to say – if I was presented with a similar situation I might take some time to adjust. I don’t think our friendship is going to change, but it’s up to him to determine the role he plays in my life while I am dressed.

A few other purchases I want to make note of:

  1. Bought a few jackets and shirts. One of shirts is a long dressy shirt with buttons in the middle. It is VERY tough to button – not a lot of stretch room around the shoulders. I can button it all, but it prevents me from lifting my arms, and the space in between the buttons gets held open. I thought it was just me, but my girlfriend, who is quite normal sized, has a similar problem with the shirt. Welcome to the wonderful world of women’s clothing.
  2. Bought a new wig – this one is half-human/half-synthetic. A cyborg wig, if you will. This will have less sheen and hopefully not tangle as much. In addition, I purchased a styrofoam head to go with it this time. For my current wig I withheld because I didn’t want to leave it out in the open all the time. I see, though, how tangled it gets, even when I store it delicately, so I’m going to have to find some place to put it.
  3. The dress I want to wear on halloween is like a low boat neck top. American Apparel sells the same dress with a V-neck too. I kind of really want to purchase the V-neck one now, with my new found cleavage skills. We’ll see.
  4. I have a few other things coming in the next few days – boots, another jacket, hopefully a better invisible strapped bra….. The purchases will have to stop soon, though, as it’s back to work for me.

That’s all I have to say for now. When the new wig arrives I’ll post some pictures of it, perhaps with a more detailed Halloween dress themed post.

For the Record

A thought occurred to me, so I wanted to clear things up.

No, I am not a crossdressing bear. I just thought it sounded funny. Also, crossdressing is by no means a burden – you just have to be careful where you put the emphasis on great.

With that said, happenings have happened! Where to begin?

As of today, excluding me, four people know I crossdress.

1. My girlfriend – she was not, however, the first to know.

2. A good friend (male) – he actually inspired me to tell my girlfriend. We had dinner one night when both of our girlfriends were out – we kind of promised that we’d each tell our respective gal pals our deep dark secrets. (He is not a crossdresser, and no, I won’t tell you his secret.)

3. His girlfriend – and here is where I interlude with a story…

On Saturday night I had planned on going out to get a drink or two with my aforementioned good friend. Knowing full well he would call me, I en femmed. The call came, and I suggested he come over, with his girlfriend, alerting him I was now a she. He thought I was drunk and said he would call me back.

Moments later the phone rings, now more composed, he asked me to restate what I had just said. I explained that I was dressed up, with my girlfriend and I wanted him and his to come on over. He recalled to me that his girlfriend does not know about my escapades, to which I was well aware, and I told him to tell her. They would come.

I freshened up my lip gloss, and began to tremble. No one, besides the GF had seen me dressed up before. She calmed me down and promised nothing bad would happen.

The doorbell rings, and I answer (stepping foot into the hallway of our apartment – farther out the door than ever before. I let the two of them in and it was done. The night went well, my friend acting slightly strange, but not out of the ordinary, and his girlfriend was cool as a cucumber. When I asked how they thought some other friends would react, my friend’s girlfriend told me that they will be okay with it because they are good friends and good friends want you to be happy. Wisdom indeed.

That brings me to number four.

4. Another friend (female, bisexual) – I only emphasize the bisexual here because it was an important factor in deciding to tell her. I knew she would be okay with everything. I suppose that’s playing it safe on my part, but baby steps, my friends.

In other news, the spending continues. Someone needs to take away my credit card. Bought a sweater and dress/shirt thing the other day. Also a few things for Halloween that I will detail in its own post once everything has arrived.

Yesterday evening my shoes arrived – you can see them here. I had ordered the wide width calf per my girlfriend’s suggestion. Unfortunately they were a bit too wide. Conundrum. Initially, I had asked my girlfriend if she would bring them to the store and exchange the size 12Ws for a size 12, despite her being a size 7. She agreed. That night, though, I couldn’t sleep – I didn’t want to make her have to do that for me (she’s done enough already, really.) I took the shoes myself this afternoon and exchanged them. No awkward stares, no comments. Yes, I’m pretty sure everyone within a ten foot radius was thinking, “who’s the queer with the huge boots?” but perhaps that’s only in my head. Regardless, exchange was made and I did it myself. I think that deserves something.

I drove home in the boots, unwilling to wait to put them on. This I suppose is the crossdresser equivalent of the kid who finds all his hidden Christmas presents weeks before Christmas. (Yes, I was that kid – Hanukkah, though.)

The boots, along with my super skinny jeans from Old Navy look great. Maybe I’ll post a lower body image later – or something with my face blurred out. I want to post a picture – at some point – I just don’t think it’s a good idea. Yet.

Before I wrap this up, one quick anecdote! The other day I joined a meetup group for crossdressers in NYC. I had to post a picture to be accepted to the group – this was okay – it’s private. Today I got an e-mail from a tranny admirer vaguely propositioning me for…. things.

Wow! In all my years as a guy I can only think of two or three times I’ve been even hit on – but this was something else. Three days with one en femme picture online and already I’m invited over to a guys house. Creepy, and just a little bit flattering.

That’s all for now – goodnight!


(Originally written August 15th, 2012)

Am I moving too fast following my new semi-out of the crossdresssing closetness? Maybe it only seems that way because it “taboo,” or maybe I should just embrace my new found openness and buy everything that I’ve wanted over the past ten years.

It seems like every time I see a commercial, TV show, or actual female with something unexperienced I want to try it as soon as possible. The way tight jeans feel around your legs. The way boots can climb up over those jeans. The feeling of a hoop earring dangling, weighing on your lobe. The feel of a heel being kept on by a strap at the top of your foot. All of these new sensations are irresistible to me.

I have always been a very tactile person, wanting to feel my way through things, relying on touch as a trustworthy, enjoyable an reliable sense. I think that one of the reasons I enjoy crossdressing as much as I do is because of all these unique tactile sensations. Just describing the way my leg feels in panty hose or the freeness of wearing a skirt is arousing.

I realize, though, after reading My Husband Betty, by Helen Boyd, that this idea I have created of the female-me is one that represents my male-oriented view of what woman is. I want to respect women and not portray a female stereotype in how I dress, but at the same time these are the things that bring comfort to me.

I don’t think I have been that bad in terms of reinforcing a man’s view of women in how I have dressed, though. Yes I’m using make-up, wearing skirts, etc., but I don’t think I’ve done anything too outlandish. I need to ask my girlfriend what she thinks about the subject.

I told my girlfriend about my crossdressing just about a month ago today and it was a wonderful decision, despite the circumstances. Yes, I have done a lot in terms of crossdressing in the past month, and I will continue to do a lot more. It makes me happy and it something I care passionately about – in terms of myself doing it, and also changing the public perception of it. I know this is something new, and difficult, but it is an issue I’d like to pursue.

Some more personal goals of mine, updated, now include:

1. Stop biting my nails and take care of them better.
2. Lose some weight. I want to look good on Halloween.
3. Go out in public. To a bar or just around the street once at night.
4. Tell more people. Leave the closet behind.
5. Maybe get my eyebrows threaded. Maybe.

Lofty, I know, but all within reach.

One more thing to add before this ends. When I crossdresser I will call myself Justine. At first I didn’t think I needed or wanted a name for when en femme, but I realize that it really is a separate identify with its own personality and deserves to be recognized as such.


(Originally written August 14th, 2012)

The word transgender can be an umbrella term. It encompasses not only crossdressers, but transexuals (pre-op and post,) transvestites, intersex and more.

It has taken me a long time to understand the difference between sex and gender, but I suppose it simply boils down to physical versus mental. I have a penis, sex = male. No questions or complications. My gender, though, is something that I have only begun to think about in the past week. Yes, I am heterosexual and love to check out girls, but as David Torrey Peters so humorously puts it, I am also schizophrenic. Yes, I am looking at your ass, but I am also wondering how I would look in your jeans.

Does this make my gender any less male? I don’t know. Scientifically speaking, yeah, it probably does. Comfort-wise, I’m not sure where I stand – yet.

There is nothing wrong with considering one’s self transgendered. I can easily say that categorically, in the broadest use of the word I absolutely am. I just don’t feel ready to say it out loud, or in a questionnaire.

Society, guilty as usual, makes it hard for a hetero crossdresser to give up the ever powerful male gender. Am I comfortable with otherness? Becoming a minority willingly is not always an easy choice. How do people react when you tell them you’re transgendered when your sex is clearly male? What kind of awkward position does that put my heterosexual girlfriend in? If I continue to outwardly identify as male gendered does that mean I am ashamed of being a crossdresser? These are questions I am not quite ready to answer, however I willingly and somewhat proudly admit they are approaching.

I will continue to read and learn about others who have faced similar situations and through their expression I will hopefully be able to discover my own. Until then, however, I will continue to ponder these questions and explore the concept of gender so that soon I may better understanding my own.

A Brief History

(Originally written August 7th, 2012)

On the eve of my birthday I am thinking about how it all started – my crossdressing, that is. I have a few very strong, very specific memories, and with them a smattering of more vague ones.

The most powerful, and important, in my opinion, dates back to I believe middle school, 8th grade, maybe 9th. I have trouble recalling those specifics. The A&E channel was showing a “reality” documentary about a group of people who volunteered to crossdress for a few weeks and live life as the other gender.

I remember seeing a commercial for this in the den with my family and immediately getting, and hiding an erection. I noted the time the show would be on, and kept it stored safely for later that night. When the time came, I went to bed early, and so nonchalantly that it had to have been suspicious.

At that time I had a small television in my room that fortunately got the cable channels. I can’t remember the name of the documentary, but I remember being so amazed that men and women could so convincingly pull of the other genders. The TV was at the foot of my bed, and I spent the entire night under the covers with an erection, clutching my penis in one hand, the television remote in the other – just in case a parent were to barge in.

The documentary was about two hours long – and would replay again late that night – around three of four in the morning. I couldn’t sleep, thinking about how much I wanted to watch it again – so I stayed up to do so. When I finally did fall asleep, I woke up in medias res of something new. My first nocturnal emission. I hastily cleaned myself up – nervous and confused about what had happened. I buried the tissues in the garbage and never told anyone.

To this day I can’t remember the name of the documentary, nor can I find any records of it on the internet.

I don’t remember if this was my first real experience with crossdressing. Something in me must have realized I was interested in this – or else I wouldn’t have watched it in secret. I don’t recall any examples of crossdressing early in my life – only a curiosity.

When I stopped taking baths and started showering, I, for some reason, always used my parents bedroom bathroom. I don’t know why this is – it’s something my siblings do as well, and I still do whenever I’m home. It’s a nice shower – that’s all I can think of. Regardless, in my parents bathroom, hanging on the inside door knob would always be my mother’s bra. I was always fascinated by bras – and over time I got more comfortable looking at them, feeling them, and eventually trying them on. Every night, before school or camp, I would go upstairs to take a shower, and quite frequently, before cleaning up, I would try on her bras.

I very clearly remember the way they looked and felt. Nylon and lace. Always white or off white. I admit – this is very, very strange, but it was apparently pretty formative, as I have such vivid memories.

Eventually, one day when my parents were both out of the house I snuck up to my parents’ bedroom and stole one my mom’s bras from her drawer. At night I would put it on, stuff it with socks and fondle my erection – never masturbating (more on that later, I suppose.)

I hid the bra behind my bed, which was pushed up against the wall and not often explored. Over time, my exploits became more intricate. First I created breasts using socks and hamster feed. Then I started making dresses by wrapping blankets around myself. I would lay in bed and just be comfortable.

One day my mom decided to use my closet to store some of my sick grandmother’s old clothes. Old lady dresses, but still women’s clothes. I had no problem wearing those. When my grandmother eventually died of cancer, her wig was stored in my garage. When no one was home, that too became part of my ensemble.

One night, the summer before ninth grade, I fell asleep with a bra on. I don’t know how it happened – I was always so careful not to get caught. Now, normally my mother would wake me up for work – this was my first summer with a job. On this morning, I woke myself up. I think. Immediately noticing the bra I took it off and hid it, along with the bird seed breast forms. Had my mom woke me up, noticed the bra, and left the room not wanting to embarrass me? I have no idea. To this day I don’t know if she knows.

I do know, though, that I had a red mark around my chest from the bra being too tight. I covered myself with a towel, went upstairs to shower and tried to scrub the marks away. No luck. Time would have to be the eraser – unfortunately I worked at a summer camp and we were going swimming that morning.

When swim came around the mark had mostly dissipated – but I was still nervous that some remnants had shown. I spent the rest of the summer foolishly thinking that everyone was on to me. I doubt anyone knew.

Eventually I moved off storing the bra and sock breasts – deciding to always play it safe. I would still dress when I was safely the only one at home. I remember being able to fit into, and then outgrowing my mother’s wedding dress in early high school. I remember the way the dress she wore to my bar mitzvah had built in curves that made my body look realistically feminine. I would stand in front of the mirror and stare at myself – too excited to feel any shame, only knowing I had a secret to keep.

Once I tried on lipstick – but never again when I spent a full week paranoid that it hadn’t come off completely. Another time I shaved a slight 1x1inch patch on my leg – partially by accident, not realizing the sharpness of razors. Although this was high up, I took extra precaution for a few weeks until it grew back completely.

By the time I was 16 I had my first girlfriend and my urges to crossdress strongly subsided. I still maintained some interest – especially on the internet. From 16 to 22 I only dressed rarely – primarily due to lack of clothing, and personal relationships. It never left my mind completely though.

I will discuss my relationship with crossdressing on the internet  in another post – there is a lot more to say on that topic than would fit here.

In the meantime, tomorrow is my birthday and I am excited to see what clothes my girlfriend bought for me to wear. I’m so glad that she’s willing to participate in this “hobby.” Yesterday she said I looked cute in a girly t-shirt I got, which was the nicest thing she could have possibly said to me at the time. She then said my body looked convincingly female. It’s these types of small little complements that make me so happy that I told her.

The First Dressing

(Originally written late July 2012)

I dressed up for my girlfriend the other day – and loved it. Let me explain the events leading up to this.

About a week ago I ordered a ton of makeup on Amazon. Pretty much everything the internet said I would need. The makeup arrived, along with my new wig the day after and I was off to the races. When my girlfriend went out I put everything to use and was shocked at the outcome.

No, not completely passable, but different – much better. The different make up and a decent wig make is enormous – perhaps an even bigger jump than the silicone breasts and padding. I actually looked kind of female – and from a distance I may have even passed. At least I’d like to think.

Anyway, I took everything off quickly and when my girlfriend came home I told her what I’d done – and that I wanted to dress up for her too.

A few hours later, there we were, in front of the bathroom mirror watching me attempt to transform. She gave me a few pointers with the make-up, which I enjoyed, and then a few minutes later the change was complete.

I don’t think she was weirded out until the wig came on. I stood from half a room’s distance at first. Kind of like a frightened animal, not sure about my proximity. She came closer – and was, a little scared, but hopefully also slightly impressed.

We sat together, and she let me kiss her on the cheek. I am not a bizarre crossdressing monster. Success.

I didn’t stay dressed for long – I wasn’t really sure what to do or say. Regardless, I was happy. This felt like a very big step.

In the proceeding days I dressed in full one more time, when she went out for a run. This time, I stayed dressed when she came home and let her find me this way. She later told me that she liked that I was dressed when she came home. I want us both to be more comfortable with this.

Yesterday we went to the mall together – and I, kind of, got to shop for women’s clothes for the first time. She really did the shopping for “her” with me present, giving awkward advice. It’s tough to balance being excited about being in Victoria’s Secret Pink, but at the same time pretending to be the boyfriend dragged there unwillingly. Totally opposite ends of the spectrum.

In the end I/we picked up a few things that I’m excited about:

  • Long sleeve white shirt, to wear under short sleeve t-shirts.
  • Black long sleeve carigan to wear over other short sleeve clothes.
  • Victoria’s Secret PINK ¾ sleeve Mets shirt (this is both of ours)

The Mets shirt was my favorite pick-up, however it doesn’t quite fit as I’d like and the sleeves, of course, aren’t as long I would like in my ideal world.

That night, when we were going to sleep, I asked if she minded if I wear the shirt, along with the breasts and she was okay with it. I think going shopping, and this whole series of events in general has brought us closer.

I’ve since ordered three baby doll t-shirts online, along with four long sleeve crew-neck shirts and a dress for Halloween. Yes, I know it’s months away, but I can’t help but be excited about it.

Tonight my girlfriend helped pluck my eyebrows – not too much, though. I was nervous about how it would turn out, but it’s not nearly as drastic as I expected and they could probably use a little more. I feel like enough was plucked from my eyebrows to create an entire third eyebrow for someone in need. And my eyebrows are still bushy.

So I’ve accomplished a lot on my to-do list already, which is quite exciting. Much faster than I would have expected. You have to realize, though, that there is ten years of repression here all coming out at once. I think my recent “obsession” will boil down eventually to a normal hobby. Well, maybe not normal, but a hobby, none the less.

I do know, however, that I am looking forward to getting dressed up again. I have picked up with my girlfriend some makeup remover, which I’m oddly looking forward to trying, as well as a hairbrush and some girly sunglasses.

Things will continue to get better, and more comfortable. In the meantime, I will await my deliveries, knowing the more I think about them, the slower they will take to arrive.