Dear Sasha: I’m 27 and I have the worst case of penis envy. I used to pine endlessly over being a boy, hating the fact that I was a girl. I’d even made and wore a plasticine penis as a child. At some point I came to terms with who I am in my life and I feel I’ve grown to accept, not hate, my body and my (lesbian) identity. Yet, my perception on life still seems penis-driven. When I use the washroom, I obsess over wanting to stand and think about buying devices to help me do that, when I have sex I have to use a strap-on or I’m not truly into it. When I masturbate, I stroke as if I had a penis. I can firmly say I don’t want to change who I am but I also can’t ignore the aching feeling of regret that is always there. Could this be a fetish? Or could I have a gender-identity issue? —Ms. Dick

Dear Ms. Dick,
Unless a person has contributed to the canon of Latin American Magic Realism, chances are they don’t have a flair for relaying abstract yet quotidian events like, say, Julio Cortazar does, and even he rides a fine line between revealing and uncurbed. This is why I have a strict policy against recounting my dreams, nor will I indulge others’ croaky morning anecdotes about Whitney Houston giving them a manicure on a tricycle in their grandmother’s basement. But in the interest of constructive sharing, let me tell you a dream I’ve been having for at least 15 years of my life:

I have a penis that I go around sticking in as many asses as I can get my hot little hands on—willing, unwilling, primed, surprised, young, old... I am without discrimination, though I do prioritize college girls. With sheer mental force I try to make my penis even larger, furthering my desire to know people in a truly visceral sense. The dream always ends with the penis turning into an old banana or a toilet paper roll and me slapping at it ineffectually, and then I wake up horny as hell. Do I feel guilty about this dream, which carries over frequently to the masturbation mill? I wish I could say I never did, but I only stopped feeling so fucked up when I met people not only willing, but anxious to indulge me in real life.

I realized that, like everyone, I exist on that roller coaster ride of a continuum we call sexuality. Do I want to be a “man”? Nope, and unlike many biological women who identify as male, I wouldn’t give up my archetypal femininity or my pussy. Would I like to have a real cock a few months of the year? Sweet Jesus, yes please! I love the overwhelming power and privilege of buggering someone in half.

Anytime we place very rigid boundaries on human expression, the same thing happens. Many, many people don’t fit the standards and they end up questioning the uniqueness and authenticity of their own. You don’t have a gender identity issue so much as the larger culture does, and you are simply responding to it the same way so many do: by feeling like a freak.

Dear Sasha: I’ve no doubt you already received a few e-mails about this subject, but just in case, I thought I’d chime in. According to George Carlin’s “List of Impolite Words,” 71 is defined as a 69 with two fingers up your ass. He also covers 68, which is “You do me and I’ll owe you one.” For the record, although Mr. Carlin can be very amusing and entertaining, he can also be quite the sanctimonious asshole. But I suppose that’s probably the niche he’s going for. —Brad

Dear Brad,
Thank you for clearing this up. Jerome also e-mailed me with this: “The 71 equals 69 + 2. The 2 is a finger and thumb. I place my bet that Managing Expectations, the one who wrote in with the term last week, is originally from the greater Sudbury area or rural Quebec.” I will not even begin to speculate why, though if this is a common greeting there, I think a field trip is in order.

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