New York City. Tuesday.

I am once again giggly excited as I arrive in town and hop the subway to work. First off, since everyone there knows I’m transgendered, there’s no more hiding. I have sugarplum visions of conversations I’ve never been able to have before, happening today. No more shame.

Second off, new boots. New women’s boots. That said, they don’t actually look like women’s boots. No heel, a few straps, a few buckles. But they are women’s boots —  from Bakers Shoes. Much like my black high-tops, this is a step in a new direction. Women’s attire that looks like men’s attire. Only cooler. 20% cooler.

I get to work and everyone is, well, working. No big hellos. No comments about my boots. No nothing. Everyone is focused on a PowerPoint presentation.

Awesome.

I know I set my expectations way too high, but I am crushed. I try not show it, and I guess I’m successful since everyone remains focused on their own thing.

A little chitchat here, a little fantasy football there intersperse the day. It’s no different than it was a few weeks earlier before I came out.  It’s as if I never shared a part of my soul with the team.

The day finally wraps. A good work day, but not such a good transgendering day.

I want to shout, hey, unburdened person standing right here. With awesome new boots!

I leave the office for my weekly therapy session, but I am down. I am depressed.

At the session, I recount my escapades from the previous week. I guess I’m too much of a storyteller as my therapist wants to know immediately if my oldest came around. Sorry. No can do. You’ll have to wait for my tale to conclude. It’s like reading the last page of a mystery. Your patience will be rewarded. Okay, maybe that’s not how therapy is supposed to work, but the writer in me refuses to cooperate.

By the end of the session, I finally address my depression, my frustration. This was supposed to be an awesome day. Not a normal day.

Did they ignore you? Did they shun you? No? Then give them time. That they treat you like they did before is a good thing. It means they still accept you. But give them time to digest the new you. Give it time, and they’ll come around.

As I walk back to my hotel, I mull these words of advice and slowly, it starts to sink in. Give it time. It’s all good.

By evening’s end, there is a renewed bounce in my step. And I have a hunch it’s not just the boots.

Thought I’d change the pace today.

Since I’m usually focused on the daily view of my transgendered journey, I haven’t really explained many of the details surrounding my path prior to September 2014.

So let me use this second F.A.Q. installment to help fill in a few of those gaps…

You talk a lot about shame and fear. What’s up with that?

I grew up in a different era. I was born in 1965 and my childhood sat squarely in the ’70s. Gays weren’t openly tolerated. Just look at Paul Lynde, dubbed “America’s most eligible bachelor.” Transgendered folk? That was even worse.

When I was in grade school we used to play a game during recess called “Smear the Queer” where all the boys would chase and tackle whoever happened to be holding the football… the queer. That sort of matter-of-fact attitude towards anything different took its toll on someone who secretly liked to wear dresses. My keen adolescent survival instinct kicked in and I quickly learned to hide that part of myself from the world.

Fast forward to my late teens and early twenties when I began to explore the outside world in girl mode. For the most part I could be myself, smile even. But there were too many encounters resulting in being pointed at, laughed at, cursed at, even threatened with bodily harm. Of being made a spectacle of over the loud speaker at a K-Mart whilst trying to buy a skirt. Or chased down Ben Franklin Boulevard when I wandered too far away from the safety of my car rather late one night.

All these experiences fueled the fear that I was, in fact, a freak. I “purged” my entire wardrobe on countless occasions, vowing to never dress again. I started to believe there was something wrong with me.

So, yeah, after 40 years, it’s still a challenge to expunge all of the shame and overcome all the fear. Because a part of me still fears I’m a freak. Still fears my friends won’t be accepting of who I am and path I’ve decided to take.

The good news? Everyone, every single person I’ve told, has been more supportive and accepting than I ever thought possible.

Are you “passable”?

This used to be so important to me. Passing as a woman.

I won’t deny that there was a thrill when I did. When my hair and makeup were just right. When I walked past people and the only looks I got were for a cute girl, not a freak. I used to tell myself that if I could pass full time, then I could do this. That I could somehow transition from being male to female with no muss, no fuss.

So on a good day, yeah, I can pass. I’ve been called “ma’am” whilst standing in line at the grocery store or the pharmacy when my ponytail is a little disheveled, when I’m wearing my black and yellow hoodie with jeans and boots.

And on a not-so good day, I’m a bloke in a dress, as Eddie Izzard is fond of saying.

But I guess the difference now is that this journey is less about “passing” and more about being who I am. I mean it’s flattering when I pass as female. It’s actually pretty awesome. But at the end of the day, I am transgendered. And if I can’t accept that, how can I expect others to do so?

Sunday morning coming down and I feel as if there’s a new normal in my life. Or at least, a new normal where I live.

No more hiding at home. No more fear of being who I am in my own house.

Who’d of thunk, right?

I cheerfully pad around the first floor in my bare feet, toenails still painted a dark red. I pass by my oldest who is parked on a couch and he stares fixedly at my toes.

Uh-oh. Uh-oh?

But he breaks into a smile and, “Wow, those look nice.”

I laugh, yeah, well I told you I have girl feet.

It’s a tension-free encounter that I didn’t think possible 24 hours ago. Hell, unthinkable only 24 days ago.

I don’t think full-blown girl mode is appropriate after all the Sturm und Drang of the past few days, but I do have a desire to show off my burgundy clogs. So I do. Again, a positive response. As in, wow, I like those.

It is such a delightful exchange, and I am finally able to respond how I’ve always wanted to, “Yeah, pretty cool, right?”

And the bonus in all this? I’m taller than my oldest for the first time in about three years. In your face!

Who knew being a girl could be so empowering?

Morning comes and I am awake at the crack of dawn.

I pace downstairs and make coffee. I pace around with my coffee once it’s brewed. And then I pace some more. Waiting. Waiting to see if my oldest son has come around.

I make sure to wear “guy” socks, and even put on my “guy” boots. Without realizing it, I am returning to my traditional role as Dad.

The kids get up around 10 a.m. to go see My Little Pony: Equestria Girls – Rainbow Rocks with a friend at a nearby movie theater. My youngest is a Brony, remember? But my oldest is still distant. I look down at my wrist and realize I haven’t even put on my hair ties, my symbol of strength and defiance.

I continue my pacing around the first floor, cleaning this and that. I just can’t be in the same room as my oldest as I’m afraid I’ll break down in front of him.

Thirty seconds in the living room, then back to the kitchen. My youngest wanders in and I ask for a hug. Not good, I tell him, not good.

Finally their ride arrives and I whisk them out the door. I close the door and lean against it before finally sinking to the ground. And the tears come. Oh, do the tears come.

That’s it, right? I can’t be myself in front of my son. The one who is always understanding. Just not of this. Or of me.

I finally pull myself back together, though I fear it takes me a good hour to exhaust my pity party. I give my face a good splash of cold water to get rid of the red rims around my eyes. Deep breath, buddy. Deep breath.

By the the time the boys return home, I’m feeling better. Whatever happens happens. Either he is here on this journey with me or he’s not. My youngest is good with me, and even more so with his Pony movie.

We finally settle in for some more Doctor Who. It’s a normal day for the three of us and I decide I can live with that. We wrap up a mini-marathon and it’s time for my youngest to get to work for the evening.

After dropping him off, I finally decide enough is enough and broach the elephant in the room with my oldest.

So we good?

Silence. Lots of face pulling, but no intelligible response.

This goes on a for an eternity, but I’m out of answers. I’m emotionally empty. I feel like there’s a path to reaching him, I just can’t find it. Thicket too dense. Machete too dull.

I finally ask if he wants to read my blog. This blog.

He nods and I head upstairs to let him read alone — without the specter of me pacing or staring at his face for every possible reaction as he reads each post.

I finally return after 20 minutes and he is staring at the screen with tears in his eyes and on his cheeks.

Oh shit. Oh shit? I don’t even know anymore.

But these turn out to be good tears. He gets up and gives me a long hug. And finally says, “Dad, I love you. I think I get it now. And I’m okay with it.” There is a sincerity in his voice and in his hug that tells me we are, in fact, okay.

The rest of the evening is good, relaxing even. We pick up my youngest a few hours later from work, grab dinner and wrap the evening with one more episode of Doctor Who.

It seems only apropos to end this with a quote from Doctor Who, but not actually Doctor Who. That does makes sense. But if not, just trust me…

When you’re a kid, they tell you it’s all… Grow up, get a job, get married, get a house, have a kid, and that’s it. But the truth is, the world is so much stranger than that. It’s so much darker. And so much madder. And so much better. 

Maybe not darker, at least not for me anymore. But it definitely is stranger, madder and so much better.

I catch my train back to BWI in the late afternoon and arrange to meet with my oldest son on the train for a weekend home from college. It’s been over a month since I dropped him off for his sophomore year at Goucher College, and it’s great to see him again.

I was hoping to get home before sharing my news, but patience has never been my forte, so we drop our bags off in my car at the parking garage and I tell him I have some things I need to talk to him about.

Now let me preface this by saying that my oldest son is the one person I was sure would be okay with all of this. He is a terrific kid. Very empathic and always there to give someone a hug when they are the least bit down.

You might see where this is going. And you’d think by now I would have learned my lesson on setting expectations. But no, that’s not how I roll.

I start pacing and tell him first about my move to NYC. All good.

Then I tell him about hiding my stuttering for 25 years. Again, all good.

Then I tell him I’m transgendered. Aaaaaand… not so good.

I am really caught off guard. This is not at all what I was expecting. And I start to get a sickening feeling in the pit of my stomach.

But I put on a brave face and tell him that he needs to react how ever he feels. We all have visceral reactions to things in life. This isn’t a time to pretend and tell me what I want to hear. This impacts him. This impacts our relationship. This impacts his life. Be honest. It’s okay.

Well, he tells me, I have a few trans friends at Goucher and I’m just not comfortable around them.

Good, good. Don’t hold back.

I try to explain that it’s not like Tootsie. That girl mode entails things like yoga pants, long skirts, clogs. Nothing outrageous. He doesn’t need to see me in girl mode. I’m still mostly in boy mode anyway, etc, etc. etc.

By now, we’ve been in the garage for a while, and I realize we should probably be driving home. We continue our conversation in the car, but this is not going at all how I had envisioned.

That said, I genuinely appreciate his honesty. And I’m sure he’ll come around. Right?

Empathy. Hugs. Just give it time.

We make a pit stop at the mall on the way home because the padding on my glasses broke off earlier in the day. We walk by a slew of women’s clothing stores, and I point out blouses and leggings that I might wear — again, nothing too showy. Nothing too age inappropriate.

He seems to start to get it, but there’s still a palpable distance between us.

We finally get home in time to pick up my youngest from work at the movie theater, and after a late dinner and an episode of Doctor Who, I find myself absolutely exhausted and emotionally spent. I tell the boys I’m beat, and head up to my bedroom, explaining they should spend some time catching up. Brother-to-brother time. And that gives me go-upstairs-and-try-not-to-lose-it time.

I close the door of my bedroom behind me and tell myself, hold it together. Give him time. And for god’s sake, get some sleep.

I crawl into bed, close my eyes and wait to see what tomorrow will bring.

Eleven down.

I think it’s safe to say that this transgendered train has sailed (I’ll take “Butchered Analogies” for $500, Alex), and I now fill my days in New York City with coffees, lunches, dinners and drinks to let people know personally what’s going on in my life before news slips out on its own.

No more hiding.

Today starts with a lunch with a former intern from NYU who spent many a day in the office discussing storytelling, narrative structure and the like with me.

Now I get to tell her my story.

We walk to the Melt Shop for lunch (the grilled cheese should do wonders for my figure) and after ordering, I find a quiet spot outside to eat and share my news. A group of rambunctious teens quickly grabs the next table, the one about six inches away from us, and I move us to a bench for a tad more privacy.

Yada, Yada, Blah, blah, blah. Aaaaaaand… transgendered.

She makes her feelings on the matter quite apparent. It’s written all over her face. She is thrilled for me.

It’s funny. I’ve come out to 12 people now and I’m at the point where I can almost classify the responses. And her response goes to the top list. Completely accepting. Thrilled for me. So much so that all my nervousness dissipates. I get to be me. I get to stop hiding a part of myself. And let me tell you, that is a wonderful feeling.

We continue our chat as I walk her back to her office, unfortunately, we come up with no new words for my new vocabulary. Guys may be raunchier, but at least they have more creativity when it comes to words for women’s breasts. A lot more creativity.

I head downtown for another meeting, this time with a guy I worked with at AOL, consulted with for a good five years, and the business partner of the first guy I told, last week.

I know he’s going to take it just fine. He’s a terrific guy, and his brother is the leading activist for gay marriage, but I’m still stressed. He’s known me for 15 years. We worked together closely for many of those years. And despite the past week of love and support, this doesn’t seem to get much easier, especially with people I’ve known for a long time.

He gives me a hug when I come in the office, introduces me around as “the best,” and we finally settle in within one of his side offices. He knows I have news, so I start with, “Not gay, not dying of cancer.”

I share my stuttering tale, then the hiding and the shame, aaaaand… transgendered.

He gives me a hug, tells me how proud he is of me, how brave I am and proceeds to dominate the conversation, much like he usually does. But it’s good. Nothing has changed between us. He still wants to work with me again, girl mode or boy mode. And he still wants to dominate any conversation he is in.

But for the first time, I realize that people, even open-minded people, don’t necessarily understand what I’m going through. He peppers the conversation with the word “tranny” and asks me if Tootsie was my favorite movie growing up. I’m hesitant to bring up that “tranny” isn’t really a word in favor within the trans community. It feels like a pejorative. Not when he says it, because I know it comes from a place of love. But it’s hard not to wince each time he uses it.

And don’t just take my word for it. To quote Wikipedia (always known to be at least 90% accurate)…

Tranny is a slang term used chiefly to describe people who are transgender, i.e. transsexual, drag, transvestites or cross-dressers. The term is considered a slur by some transgender activists, such as Roz Kaveney. The Gay & Lesbian Alliance Against Defamation (GLAAD) state that the term is “usually considered offensive and/or defamatory” by members of the transgender community. The gay community is believed to have originated the term, and many members of the gay community feel the word is a term of endearment.

As for Tootsie, that’s the first time that movie has been referenced since I started coming out. Sure, I liked the movie, but it didn’t speak to me. It’s about an out-of-work actor who takes on the role of a woman to get work. It has very little to do with gender identity, at least for me. I certainly don’t dress up in glittery gowns and wave around American flags, and perhaps that’s what some people will envision in their minds. That this is about clothing and theater. But that’s not what it’s about for me. It’s about me being who I am.

In a way, that’s what this blog is for. To educate people on what I’m really going through.

Perhaps our next conversation will be a better time to bring this up. I really don’t want to ruin the moment over technicalities, because it is genuinely a delightful meeting and I’m blessed to have friends like him.

His assistant breaks in on our discussion and he is pulled into another meeting, but not before giving me another hug and a kiss on the cheek.

That night, I find myself unexpectedly in New York City for another day, and end up having drinks with a young guy who used to work for me on a web project where we relaunched 167 radio station websites in a little over two months.

I wasn’t planning on outing myself with him. More of a catchup, but we have such a delightful conversation about life that the moment just seems right. I tell him, and maybe these kids in their early ’20s just have a different outlook on life, but he is thrilled for me. It doesn’t phase him in the least and he tells me how much he admires me for being honest with myself and being so open about it.

I guess waiting 40 years to come to grips with being transgendered doesn’t sound very brave to me, but I’ll take what I can get. And so far, that’s 14 amazing friends.