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?

Who Am I?

When you discuss the word “identity” in terms of crossdressing there are two ways to look at it.

1) The identity of the male, as the crossdresser, and what it means to him – how he will adjust to/deal with/understand  his identity as a crossdresser.

2) The identity of the crossdresser en femme – how he sees her, who she is, and how she sees herself.

They say the difference between an experienced teacher and an inexperienced teacher is the question they ask themselves at the end of the day. The inexperienced teacher says, “How am I doing?” and the inexperienced says, “How are my students doing?”

As a new crossdresser, in regards to my relatively recent outness, I’ve been focusing in my blog primarily on the first interpretation – which I believe corresponds to the “How am I doing?” question. Now, with some experience under my belt, it’s time to focus on her.

My girlfriend once asked me if Justine had her own personality.

She had noticed that I was more “cuddly” as Justine – more willing to touch and be touched. En homme I’m not one for touchy-feely. I don’t think I’m cold or aloof – I’m just never the one to embrace embraces. As Justine it is the opposite – sometimes it almost seems as if I crave the presence of others. I think this is definite remnant of when crossdressing served primarily as a fetish. Touching is primal and sexual, and when I am crossdressing those feelings are certainly present in my mind.

So yes, in that aspect – I, Justine, have my own personality. In thinking more about the subject – it is, however, deeper than I initially imagined. (I’m beginning to believe that all of crossdressing is deeper than I imagined, but that’s just another thing I love about it.)

Something I wish I could do, but never do, is dance. I spent three years in college going to bars where other people danced around me. I’ve gone to numerous weddings, bar mitzvahs and other parties where I sit sheepishly and watch others have a good time. There’s something about an awkward white guy that screams, “DO NOT DANCE!” I don’t know if it’s a case of societal stereotypes breeding self-fulfilling prophecy, or just that the genes for science fiction fanaticism and lack of rhythm go hand-in-hand. When I’m Justine, though, I want to dance. I want to be able to go out and have a good time in a way that the male me doesn’t (or can’t?) I want to be who I am not in a way that goes beyond gender.

In My Husband Betty, Helen Boyd discusses how, often, crossdressers’ female selves are often representative of the female they desire. Discussing this is treading on dangerous waters because a) I have a girlfriend and b) until now I have not thought of myself as this type of crossdresser.

I want to be very clear here – I love my girlfriend and want to be with her. When I crossdress, Justine, in a fictional way, is another girl I desire. Despite the fact that a television show called, “The New Adventures of Justine” would consist of sitting on the couch watching movies, typing blog posts, episode after episode, I fictionalize an entire backstory for her (or me) that has never existed. I imagine Justine (me) goes out and has a good time, rebuffs the pick-up lines of men, and knows her way around the world in a way that the male me does not. She is calm, cool and a little bit kick-ass. She is interested in the same things I am, but is more confident. Despite all this, she would still be into a guy like me. In a way, I am in love with myself.

I need a cool theme song...

A Crossdressing Sitcom


It’s funny, though, because all of those things that I described Justine as? That’s also how I think of my actual girlfriend. What doesn’t make sense now, is why does Justine exist? I have always had very low self-confidence in my male form – creating Justine, I reiterate and believe, allows me to be who I am not. It just so happens that she is what I believe a girlfriend should be/who my actual girlfriend is.

This tells me one thing: The girl of my dreams is nearly identical to my girlfriend. This is a good thing.

This also begs the question: Does Justine need to exist if I am content in my relationship? The answer is yes – and I think Justine would exist in the very same manner she does now, regardless of my relationship status. I don’t view Justine as a replacement girlfriend, but as a version of me that the male me desires – even if most people meet that quota in their ideal relationship.

I’ve digressed, now. This blog post was originally intended to describe Justine – not question of her (my) place in my (his) life. I suppose that understanding the relationship between Justine, male me, and my girlfriend is related, however – because in some ways this is a monogamous relationship with a third “heel.”

So I’ve now defined Justine in terms of existance, but the personality question still lingers. I can tell you this (and it may be redundant.) Justine is fun, happier, and in my head more outgoing than male me is. She likes fashion, sci-fi, shopping, board games, partying, and cuddling at night. She is a more wholly realized version of me. The aspects of me that have been repressed for one reason or another (that’s a whole ‘nother post…) She likes to be dominated, but also sometimes do the dominating. She likes to take you by surprise just as much as she likes to be surprised. She is me, but she is not. Her and I are me, and they are two sides to the same coin. (Wow, talk about cliche.)

This has been a very healthy blog post. I started writing it, not knowing where it would end up, and I am very happy with the results. My mind is clearer about my identity, and perhaps that mental first step is part of the path to a physical first step out the door. I wanted to go for a walk outside tonight with my girlfriend, but I used the rain as an excuse. There are about five perfectly good umbrellas within fifteen feet of me. I’m lame. One day.