DEAR SUGAR: “And all this Hot Catholic Energy, too. Man, Catholics are such sexy freaks.”


Dear Sugar,

I apologize in advance because I’m going to give you a lot of history and concerns before I get to my questions. A very Catholic girlfriend of mine was dating a very Catholic guy. Both of them were virgins and wanted to wait until marriage before having sex. Whenever things got too passionate, he would tell her that she was “evil” for “tempting him.” Consequently, this made her feel guilty and sinful.

After he broke up with her she found comfort in the arms of a transgendering female to male partner. My friend believes she is in a heterosexual relationship because the person she is with is a man on the inside. She has sexual relations now and she believes that the love they share is beautiful, not sinful. She argues that she is not a lesbian because she is not attracted to women and she does not touch her partner like a woman. Whether or not her partner is a man on the inside, he still has a vagina and breasts (though he does have a deeper voice and facial hair due to testosterone therapy). Physically, isn’t the sex they have the same as the sex two lesbians have?

Now that her first sexual experience is not with someone born in a man’s physical body I’m concerned that unconsciously she will always view sex between a penis and vagina as sinful and wrong (because of her first relationship) and has begun to program her body/mind to respond to sexual desires towards someone of the same physical gender as herself. This might be trivial but she claims she is no longer a virgin. I didn’t ask her for the details, but I’m guessing she didn’t lose her virginity by rubbing vaginas together. I could be wrong, but I would assume she lost her virginity to a vibrator. I guess I’m worried that if she ever does have sex with a penis it will feel like a broken vibrator or something. I know your advice will probably be something like “be happy for your friend if she’s happy” but I’m genuinely concerned with how this untraditional sexual experience will affect her sex life in the future. I just wish she had penis sex first so that she could have some kind of reference, you know?

I guess my main question is, is my friend a lesbian if she is attracted to and enjoys sex with someone of the same gender (taking into account that they both believe he is a man on the inside)? I know part of your charm is to be brutally honest, but could you show a little sweetness in your response Sugar?

Concerned Friend


Dear Concerned,

Omigod, you are SO crazy. And your friend is crazy, too. It’s like your crazy met her crazy and had a little crazy baby.

I fucking love it!

I want to invite you guys over to my place to party. And bring the hairy lesbian/transgender dude, too. Why not? It seems like you guys have lots to talk about, what with the Mystery of the Lost Virginity and the Penis Sex First Anxieties. And all this Hot Catholic Energy, too. Man, Catholics are such sexy freaks.

But mostly I want to assure you that your friend (while crazy) is doing fine. She’s finding her way. It’s an unusual way, but I’m pretty sure your anxieties say more about you than her. Don’t mean this in a mean way – I’m trying to be sweet – but the question get answered her is why her sexual life matters to you.

Remember: I can help with this! But it’s going to require that you guys head over here and drink too excess with me. Until further notice, I’m baking cookies in the nude.


Dear Sugar,

Should I quit my job? Seriously, I’m going to do whatever you advise… no pressure though. A little background? Usual story: boss is a jerk, pay sucks, feeling the drain of the same schedule every day, wishing the coffee machine wasn’t broken, etc.

What do you think?

Leaving It Up to (Sugary) Fate


Dear Leaving,

You sound like a young boy with strong forearms. Am I close? If so, then I have some terrific news: I need an intern. I realize I’m taking a chance, given that your note suggests a less than ideal employee. But what the hell. Your only responsibilities will be fetching me cookies and licking my calves.

Now that I’m your new boss, I have a few quick questions.

First, how do you feel about nut play? (I’m crazy for it.)

Second, how do you plan to earn money?

Third, why didn’t you think about that before?

Fourth, why are we arguing already?

God, I hate it when this happens. One minute I’m gurgling your intimates and the next the EEOC is involved. Just remember what you were when Sugar found you.