Good Friends

Sometimes it’s not easy to write. Some people rely on writing at certain tables, others depend on a certain ink. I can write from pretty much anywhere, with just about anything. I just can’t force myself to do it.

Hurricane Sandy, while sparing me, hit my family fairly hard. After my blog post last week I spent three straight days helping my family. My family, in the house that I grew up, faced five feet of flooding in the basement and garage – both of which generally saw a lot of use. In addition, two cars were destroyed and today, almost a week after a storm they are still lack electricity, heat, cell service and all that other good stuff. Very fortunately, everyone is safe.

Spending so much time laboring to clean with them certainly brought everyone closer, but not in a way that has impacted us yet. It’s still the “I cant believe this happened” period, not yet the “Look back and laugh sadly” time. If there’s anything crossdressing-related I can take away from this is that when I do come out to my family, I think they will all be supportive no matter what.

This post is supposed to be about good friends, though, so let’s move on.

If you recall in an earlier post, I discussed one friend who had a not-quite-welcoming reaction to my coming out. Nothing negative, just general shock and disbelief. He too lost power and first-world life in wake of the hurricane and needed a place to stay. My girlfriend and I took him in over the weekend, which proved for good bonding in a time of need.

On Saturday I boldly suggested that I would go out to a bar dressed. My girlfriend, house guest, and two other friends in-the-know obliged pending my ultimate decision. Ultimately, I don’t think anyone particularly wanted to go out to a bar, so instead went over to our friends’ house for board games and moves. I went dressed.

At Home

After a night out with friends

Walking over dressed, without the shield of an umbrella this time, proved exciting. The fear of going short distances in the dark is certainly starting to wear off. Baby steps. That’s all. What mattered more to me is the fact that I was able to spend a good few hours dressed, with friends and no one made a big deal of it. Our time together would have been no different, regardless of what I was wearing. This meant more to me than anything else.

It’s these kinds of experiences that I think are necessary to build confidence and ultimately help me venture out into more populated areas during brighter times. I know I mentioned in my previous post going out en femme on New Years. That’s definitely a long shot, but further, larger steps are most definitely in the picture.

Eventually the goal is to be able to step out of the house without reservation regardless of what I am wearing. Like complete recovery from Sandy, this goal is long term and will certainly take time and patience. Both, though, are certainly attainable with the help of family and good friends.


A Family Affair

In a comment in an earlier post Randa Lane briefly referred to the fact that no one in her family knew that she was a crossdresser. I’ve always given thought to finally talking about my hobby with my family, but before her comment I hadn’t considered writing about it.

Here’s a brief summary of my family, before I go into the specifics about how I think each would react if I told them.

Abstract: My nuclear family consists of five members, including myself. My mother and father are both in their early fifties. My father grew up outside of New York City, and my mother grew up on Long Island, in the same town my family now lives and where I grew up. I have a younger brother who is almost done with his undergraduate degree, and a younger sister who is now beginning to look at colleges for herself.

My family is very middle class – my father is self-employed and works in the communications business, and my mother is an office manager in a doctor’s office. Politically, I think it safe to say that my family is left leaning all-around. Socially, my entire family is in favor of gay marriage, despite the fact that my parents are still slightly skeeved out by it. My parents can be a bit backwards about things – they like to consider themselves socially progressive, but would probably get upset if a black family moved on to their block. My brother and sister are both in favor of gay marriage and don’t really care about race. My brother and his friends still throw the term “gay” around pretty freely as a derogatory term, but I think my brother knows that it’s wrong, only doing it to sound cool.

The topic of crossdressing hasn’t, as far as I know, come up in terms of my family.  I don’t think there’s a history of it, and if my father or brother have ever experimented, it’d be news to me. Whether or not they know about me – I have my paranoid suspicions – but I think I covered that briefly in a much earlier post.

My Father

I don’t think my father is the first person I’d tell, but I’ll go in descending age order. My father considers himself a staunch democrat and considers himself accepting of almost anything not inhumane. One of his best friends growing up came out of the closet in college, and my father has remained close with him his entire life. He was actually named my godfather, although over the years we’ve never kept in great touch. In terms of LGBT issues, I would consider my father fairly ignorant, but mostly open-minded. He doesn’t know much about the issues, but if it tugs on his heartstrings (and most things do) he’ll be a champion of your cause. He’s a compassionate, thoughtful individual who desires only to include others in the things he does, and to a fault expects him to be included in what others do.

It’s this bigheartedness that makes me think that he would be the more accepting of my parents – but I don’t think it would come without a number of questions. For one, he would certainly ask the same questions most people do. Does this mean your gay? Do you want a sex change? The usual line of questioning when you come out to someone as a crossdresser. I would answer him honestly, and his questions would probably consider. He’d be interested in my history – how and when I started, why I do it, etc. and I’d be completely honest with him. I have a policy of not lying to my parents (or most people in general) as lies are generally difficult to keep track of, and honesty builds stronger bonds, creating mutual trust. Honesty is just easier.

(I realize the hypocrisy here, of maintaining a policy of honesty, but keeping my crossdressing secret. I think of this more as lying by omission. No one’s ever asked me if I was a crossdresser, so I never bring it up.)

The problem with my father would be his sharing. He likes to talk. To everyone. I’m sure he’d know someone who knows someone who knows another crossdresser and would immediately want to share with them. And everyone on Facebook. It would just slip into conversation, casually, perhaps without him even realizing it. I know he would promise to keep it a secret, but I don’t know if he could keep that promise.

I have to consider an alternative, though. My brother is, as far as I know, straight, but has never been with a girl. I’ve discussed with my dad the possibility that my brother could be gay, and it is always met adamantly with a “no.” As if that’s not even an option. I know my father would love my brother and myself, unconditionally, but I could see my crossdressing as something difficult for him to accept initially, and perhaps over time. I don’t think anything, though, could ever sever our strong relationship.

My Mother

I would tell my mother before I told anyone else. This, despite the fact that I think she would be less accepting than my dad. The reason for this is because my mother has always been easier to talk to. Our time together has always lent itself to more in depth and personal conversations. Growing up when I had problems with relationships, I would go to my father. When I had problems with myself, I would talk to my mother.

Despite my father’s ambitious outward compassion, I think it is my mom who actually spends more time in serious though about other people – especially her children. When it comes to her kids, my mom has never put herself first.

I think if I told my mom, she would try to remain open-minded, and ask similar questions that my dad would. I think she would have more in depth questions that string together, with more specifics in terms of how it affected me growing up, and how it affects me now. I think she’d be more interested in how far I take crossdressing, and is more likely to ask to see pictures than my father.

Despite this open-mindedness, and line of questioning, I don’t know if she would be accepting. My mother likes to consider herself socially liberal, and understands why I and my father are, but she grew up in a slightly more conservative household, and sometimes has difficult accepting lifestyles that differ from her own. In another life, where my mom did not grow up on Long Island, I could see her as an activist for women’s causes, and even other minority groups. Instead, though, she champions the causes of her children, and friends who have been wronged, even if ever so slightly. She knows how to fight, and more importantly how to win a fight. I digress.

My mother would ask, and she would listen, but in the end – I just don’t know. When given the option to attend my gay godfather’s wedding my mother scoffed, “I don’t want to see two men kiss.” Strange words from a woman who supports gay marriage. Now, I know being gay is different than being a crossdresser, but despite this, they’re two lifestyles that are linked in terms of social rights and if my mom can’t get behind two men kissing, could she understand one’s desire to wear women’s clothing? And how would she react to the fact that this all began with her clothing. If she asked, I, once again would not lie. My mom is a social creature, and would probably want to discuss this with her friends, getting their opinions. I think this would be a terrible idea, as her friends are far more close-minded than she is. She might also want to see a psychiatrist, to get a professional open. I would suggest this to her, and she would probably be open to it.

In the end, like my father, I think my mother would love me unconditionally. I could murder someone, and the love would be there. Besides, what’s a few bras between mother and son?

My Brother

My brother would probably be the last person told. To be honest, I’m not sure if there would ever be a purpose in him knowing, other than no longer wanting to lie by omission. My brother is a mysterious creature. He didn’t do too well in school, but I don’t blame him, as he worked hard despite a learning disability. He’s in college now, which may or may not be a mistake, but I think in the end it will do him a world of good.

You see, I think there are two sides to my brother. My true brother, and the person my brother projects. When you talk to him one on one, he is inquisitive, open-minded and even sometimes insightful. When he’s with his friends, however, he becomes “just another one of the guys” prone to wearing wife-beaters, drinking shitty beer, and saying and doing stupid things. It’s this conflicted personality that I think has led to my brother being friends with many fraternity members, but not actually joining one himself. I hoped that with age he would become more “true brother” but so far, nothing.

(Fair warning – my idea of “true brother” might just be one I project on to him – the brother I wish he was, not the brother he actually is. That’s a post for another blog, one that doesn’t actually exist.)

Moving on, I reiterate, I don’t think telling my brother would accomplish anything. His response would most likely be in the form of lack thereof. He’d probably shrug and ask why I told him. He’d probably then do some research, but never actually confront me about it again. My brother and I have enough distance in age, that conversations about girls, sex and all those other brotherly things, never actually occur between us. I try to talk to him, but he doesn’t like to share his personal life with me.

I do know this – my brother has certainly become more liberal in college, and most definitely supports gay marriage. I don’t think he really knows anyone who is gay, but he understands that there’s no point in keeping someone from being happy. He’s not going out of his way to support gay rights, but he would certainly never do anything intentional to hinder them. If my brother ever finds out I am a crossdresser, it’s because everyone else in my family knows, and then, hey – why not?

My Sister

My sister is in High School and is definitely the most open-minded of my siblings. She’s popular, but a free spirit. She knows where she stands on social issues, and isn’t going to be swayed by anyone. She’s strong in her liberal convictions, but ignorant of their history and their importance. I don’t think any of this is uncommon amongst high school students.

The age gap between myself and my sister has created a relationship that is actually very strong. I like to consider myself a good big brother, and she looks up to me. I don’t think telling her while she is in high school is a very good idea, though. High school students cannot keep secrets. I don’t think she’s mature enough to understand why someone crossdresses, and she’s very liable to take my crossdressing the wrong way. Interpret it as me being gay, or wanting a sex change, despite the fact that both these things are untrue. High schoolers have a way of jumping to conclusions. If, however, I did  tell her now, I’m sure she not only be accepting, but also an eager participant, wanting to know more about it, especially the physical dress-up aspects.

When she’s in college is another story. Give her a few years, and I think she could mature enough to handle the situation. This is all supposition, though, so we’ll see where she is in a few years. Like my brother, I think college will be good for her. Either way, if she ever knows, my parents will both already know, and it also won’t be for another few years. Finding out your big brother is a crossdresser is not only a bizarre burden to place upon a stressed high schooler, but also an unnecessary one.


So there it is. Writing this has forced me to give more thought to when and if I’ll tell my parents. And I think it’s more a matter of when. I think it’s important to be honest with them, and I think the broadening of their horizons will ultimately be good for them. It’s also important to me that I’m accepted by the people I care about. But isn’t that the case with everyone about everything?