In what wins the “Bad Timing” award, my psychiatrist was on vacation for the first two weeks of my new adventure. I was completely lost. When I started this, I figured I’d dress when I saw Lisa and otherwise would stay me. Yet, I found myself getting lost. I’d forget my name when I spoke to clients. I’d spend twenty minutes in the morning trying to decide what to wear, and not because I was trying to decide which of my new outfits to wear. Rather, it was because I couldn’t decide who I was. I know a lot of people would love to be able to switch but, believe me, when you have to do it, it’s no picnic.

On the other hand, my agony caused me to stop eating. I lost nine pounds in two weeks, and my waist dropped 2". But then, on the other hand, I now was, without the corset, 36", 26", 31". I was starting to get curves and I still wasn’t sure that this was what I wanted. It didn’t help that more and more people assumed I was a woman. For example, I went to the gym dressed in my usual workout clothes and handed the attendant my i.d.

“Brian,” he said. “That’s an unusual name.”

“Not really. I know a lot of Brians.”

“Yeah, me too. But I never met a girl Brian. That a family name or something?”

“Something like that.”

“Anyway, enjoy your workout, Miss Rosen. By the way, if you don’t mind me saying so, your picture doesn’t do you justice.”

I blushed and stared at the floor. “Uh, thanks.”

When my shrink’s vacation was over, I alternated between utter joy that she was coming back, since I needed to talk to someone and Lisa was hardly objective, and utter fear. I spent the entire morning before my appointment agonizing over whether to go as Brian or Jessica. I have no idea what possessed me, but I decided to go as Jessica. I knew I was opening myself to severe scrutiny, but yet I felt oddly compelled to do it. Maybe I was facing yet another monster.

I made sure I arrived just before my appointment, since I really didn’t want to have to deal with her receptionist. I wore a white top, green silk skirt with a pink floral print and pink 3" heels. Julia came into the waiting room, and did a double take. When she figured out it was me, she said, with a bemused smile, “Come in.” We sat down opposite each other.

“Hmmm,” she said.

“You didn’t say my name out there. You always do.” I said.

“Well, I think this is a little unusual, don’t you, Brian?”

“OK, I admit this must seem a little strange.”

“Well, is there a particular reason you’ve chosen to come dressed this way?”

“In drag?”

“I wouldn’t have chosen that term. I usually associate it with somewhat more flamboyant attire. You’ve clearly chosen to try and pass as a woman. Would you care to explain why?”

And, with that, I went through the entire story of how this came to be, even the whole Jeffrey incident. When I finished, she said, “Hmmm, that’s all very interesting. Why don’t you tell me why you did this?”

“I did. Jessica asked me to be a bridesmaid, and I agreed.”

“We’ll cover that. But, as you said, the wedding is six months off and yet here you are, dressed immaculately. Why do you think that is?”

“I told you. Lisa said she wanted me to get used to it before the wedding.”

“I understand that. But that’s a little simplistic, Brian. Clearly, something compelled you to do this. You could’ve easily said no to her or, at a minimum, not agreed to effectively live as a woman for six months. Friend or no friend, that’s a little extreme. Do you think you’d like to become a woman?” she asked, rolling her pencil between her fingers.

I rolled my eyes. “Quite frankly, Julia. I’m a little surprised and disappointed with that question. I’d expect that from Jim, not from an experienced practitioner.”

“Interesting attempt at deflecting the question, Brian, but you haven’t answered. Or have you?”

“No, I haven’t. And the answer is ‘no, I do not want to become a woman.’ I did this as a favor for someone who’s always been there for me. That’s it.”

“Do you think there might be another reason?”

“No, I don’t. But clearly you do,” I said testily, “so why don’t you share it?”

“What do you think my reason would be?” she said, in that manner that all shrinks have in turning the question back on you.

“How should I know? Reappropriating the symbols of the oppressors?”

“Interesting. I’m not sure I follow.”

“I read it somewhere. It’s when an oppressed minority subverts the stereotypes that the majority has put upon it. Like blacks calling each other ‘nigger...’”

“I’m aware of what the term means, Brian,” she interrupted. “But, I’m not sure I follow in your case.”

“Look at how I’m dressed. Society sees gay men as women, so I’m taking on the trappings of womanhood to subvert society.”

“You’ve always been very good at jargon, Brian. But, in this case, I think you and I both know that it’s inappropriate here.”

“Oh really,” I said, rolling my eyes. “How so?”

“If you were truly interested, consciously or not, in, quote ‘reappropriating the symbols of your oppressors’ unquote, you’ve chosen an interesting way of doing it.”

“Now, I don’t follow.”

“Look at how you’re dressed. Your makeup is subtly flawless. Your clothes are immaculate. Very feminine yet entirely appropriate, although I think, quite frankly, you’ll find yourself tiring of heels after you have to go up and down stairs enough. You are entirely passable.”

“So, how does this disprove my theory?”

“How do you think it does?” she said, with a sly smile.

“For once, Julia, answer a question with an answer, not a question.”

“Calm down, Brian. It was a small joke. I think my response to your claim of going ‘in drag’ answers the question.”

“I sill don’t get it.”

“If you were truly interested in flaunting your sexuality, you’d be dressed in a way to call attention to yourself. Much more flamboyantly, a la the drag queens in the meatpacking district. You would trying to caricature femininity to make a statement. Instead, you’re dressed like the average woman on the street. Therefore, I think that there’s another agenda other than subverting society at play here.”

I clapped slowly. “Very interesting, and all on the fly. I’ve already told you my agenda. I’m doing a favor for my best friend, that’s it. What did Freud say, ‘sometimes a cigar is just a cigar?’ This is just a cigar, Julia.”

Now, she rolled her eyes. “OK, Brian. I see your point,” she said. “Yet, you’ve clearly chosen to embrace the role, as it were. I mean, your makeup, hair and clothes are flawless. Did Lisa pick these out for you?”

“No.”

“Did someone else?”

“No, I did.”

“Interesting. Did she do your makeup?”

“No, she has to work everyday.”

“Did she teach you?”

“No, I taught myself. Oh great, now what do you have to say?”

“Really? You are really quite talented. It’s flawless. Why do you think that is?”

“I don’t want to look like a clown,” I said huffily. “A job worth doing is a job worth doing right.”

“That’s your father’s saying, isn’t it?”

“Oh god, now we’re going to start covering my father. I thought Freud was fairly discredited.”

“Let’s keep to the topic, Brian.”

“Yes, it is his saying. And?” I said, defensively.

“Well, we’ve certainly covered his response to your coming out. Do you think your doing this is somehow revenge?”

“How?”

“You tell me.”

“I don’t know. Like I was always this total disappointment and somehow by taking his advice and applying it to this, it was like getting even with him?”

“That’s a possibility, no?”

“I guess. I mean, no matter what I did right, I was a disappointment. I mean, I graduated magna cum laude and he still thought of me as a little pansy. And, we both know what he did when I came out. Yeah, maybe, this is some kind of revenge.” My voice started getting louder. “Like, ‘I’m going to be the biggest, queerest little faggot you ever saw, dad, fuck you. How do you like me now, huh?” I said, with increasing ferocity. “I mean, look at this, I’m a beautiful woman, here’s your ultimate worst nightmare, you dickhead. I dress like a girl and men fuck me. I mean, I don’t even do the fucking. I get fucked. Hard. I’m a catcher, not even a pitcher. And I like it. And I suck dick and I like it. I like a mouth full of cum. I like swallowing. How’s your little boy now? I give it one hundred percent like you always said.” I stopped. “Wow. That’s pretty fucked up. Is that what they call a catharsis? I thought stuff like that only happened in movies.”

“Does it feel better?”

“Oddly, yes. It’s funny. Like I said, I told Lisa that I tried the clothes and makeup to try and face the monster under the bed. Well, I guess I figured out who the monster is.”

“That’s good. But, it’s really only part of the puzzle. Why do you think you agreed to do this?”

“Haven’t we been covering that for the entire session?”

“On one level, albeit a fairly deep one. But you and your father haven’t spoken in twelve years. There’s not a real likelihood that he’d ever see you like this. Something else compelled you to do this.”

“Are we going to start talking about my mom now?”

“Do you want to?”

“Not really.”

“Do you think this is somehow related to her?”

“Since you’ve been away for two weeks, I’ve had to parse this on my own and, no, I don’t think it has anything to do with her.”

“Then, why do you think you chose to come dressed today?”

“Because, it’s been a big deal for the past two weeks. I thought I should show you.”

“Are you looking for approval?”

“Are you now my mommy?” I sneered.

“I didn’t say that Brian. But, it’s interesting that you did. Like you’re trying to show me what you can do, or is what you did?”

“What does THAT mean?”

“Well, what did you expect my response would be?”

“I don’t know.”

“Praise? Critcism?”

“Do you have a problem with this? What do you think?”

“I’m not here to judge you Brian. I reserve criticism only for patients engaged in behavior harmful to themselves or others.”

“Does this fall into that category?”

“Should it? Do you feel as though you’re harming yourself or others?”

“Others, no. Me, I’m not so sure.”

“Why do you say that?”

“I don’t know. I’m just very conflicted. Like I don’t know who I am anymore. On the one hand, I like me as me. On the other hand, this,” I said, waving my hand up and down, “gives me a weirdly heightened sense of reality.”

“Meaning?”

“I don’t know. I’ve become much more aware of my surroundings since I started.”

“Why do you think that is?”

“I don’t know. Fear? Like if I let down my guard, I’ll be found out and beat to a pulp.”

“I’d like you to try something this week. If and when you’re dressed, try to just be in the moment. Don’t think about. Just be.”

“Easier said that done, Julia.”

“Just try.”

“I’ll try.”

“Let’s talk about Lisa. Why did you do this?”

“I told you,” I said with exasperation. “Lisa’s always been there for me, so now I’m there for her.”

“Has she always been there for you?”

“Uh, yeah. I mean she took a week when my mom died, and she totally helped me when my dad exploded when I came out.”

“But, has she always been there for you? Has she been there for you during your relationships?”

“There haven’t been a lot of those.”

“Well, has she been there when there have been?”

“I don’t know. I guess.”

“You guess? Well, have she and Jim ever gone out with you and a boyfriend?”

“Um, let me think about it,” I said, with a pause. “I don’t think so. But I think Jim would be uncomfortable.”

“Hmmm. Has she ever said that?”

I suddenly felt the need to stare at the print in my skirt. “No.”

“Does she ever talk to you about sex?”

“We talk about guys.”

“I don’t mean checking guys out on the street. I mean, does she ever talk to you about yourself as a sexual being?”

“Do you talk to your friends that way? I mean, do other people who aren’t shrinks talk about themselves as ‘sexual beings?” I said sarcastically. “Come on.”

She didn’t respond. Instead, she asked, “Have you ever talked about her relationship with Jim?”

“In detail. Nauseating detail.”

“Has she ever reciprocated?”

“No, you know what, I don’t think so. But, then again, I don’t know if I’ve ever tried.”

“Why do you think that is?”

“I don’t know.”

“Do you think she would have a tough time dealing with you as a gay man?”

I laughed. “I think that cat’s out of the bag, don’t you?”

“I don’t mean as some kind of camp figure. I mean as a sexual equal.”

“That’s a little much, don’t you think? Again ‘sexual equal,’ ‘sexual being.’ I don’t think anyone thinks about their friends that way. But, anyway, she was the first person I came out to, and she has always been totally cool. You’re being unfair.”

“Am I? You’re not answering my question.”

“I don’t know. Like I said, maybe I haven’t tried.”

“Why? Are you afraid she’d reject you if you were somehow more sexual? Do you think that would scare her?”

I looked at my nails, then played with the hem of my skirt. “I don’t know. Maybe?”

“Then, why did you agree to do this? Do you think is a way of somehow gaining her acceptance?”

“Like what, I’m no longer a gay man, but another woman? Isn’t that kind of pat?”

“Is it? What about the whole incident in the restaurant?”

“Meaning?”

“Meaning, you flaunted your sexuality in front of her, although in a more societally acceptable way?”

“I don’t understand. Societally acceptable way?”

“Yes, by embracing the outward trappings of a female, you could actively pursue a man in her presence.”

“Huh. I don’t know. Maybe.”

“And, yet, you said that she responded extremely negatively to you doing this.”

I sat up. “She was just looking out for me. I mean, if he had found out, I would’ve been beaten to a pulp. I mean, do you really believe that he would’ve been all, ‘Hey, you’re a guy! Cool!’?”

“Clearly, no, Brian. But it’s not as though she got upset because you were leaving with him, but rather simply because you were flirting, albeit in, quite frankly, an over-the-top manner. Do you flirt that way with guys when you’re not dressed this way?”

“No, not really. I always feel awkward.”

“So, I return to my original question. Does this feel more comfortable for you?”

“Sort of. I mean, it’s like a costume. Or like I’m an actor playing a role. It’s not me.”

She looked at her clock. “I’m sorry, Brian. But session’s over. We’ll have to continue this next week. Think about what we’ve talked about.”

“Oh boy. Fun, fun, fun.”

“Brian,” she said, in an annoyed tone.

“Sorry. See you next week.”

“See you next week. Again, I must compliment you on your look. You look adorable.”

“Thanks mommy,” I said flatly. “I’ll keep that in mind.”