Dear Jen,
While I was bra shopping, not for anything fancy, just for a regular, everyday bra, I came across one that was...WOW! Bazooms city!  I thought that maybe I'd like to hit the town looking that stacked, but then I began to worry:  what if I meet a guy who likes cleavage-me, and when we get intimate, the bra comes off, and the bazooms vamoose? In this city with millions of dollars worth of fake boobage bouncing around, is it better to buy a bra that competes and worry about the (ahem) fallout later, or is the false advertising just not worth it?
- To Boob or Not to Boob?

Dear Boob,
As anyone who's ever been to a good drag show, or who's ever disco danced at a tranny bar knows, most trannys put most biological women to shame in the "I am a hot-ass hoochie mama" department.  They dress it up, stick it out, and parade it around like the hard-earned altar to femininity that it is.  Their take on womanhood is fun, fierce, and as girly as it gets - I don't care how big the dick dangling between their legs may be.

Meanwhile, those of us who've been in more long-term relationships with our girl bodies run the risk of taking them for granted.  I mean, I work it, I look good most of the time, but sometimes I feel like my boobs and I are like an old married couple.  I assume that they'll always just be there, hanging around, and tend to only dress them up and take them out on special occasions.

So please, buy that bra, woman.  Think of it as your tranny fairy godmother.  And don't worry about seeming insincere. It's just like putting on make-up, high heels, a baseball cap over a bald head, or padding your resume - whatever gives you the confidence to get out there and show yourself to the world is a good thing.  The real beauty lies beneath anyway, the rest is just a bunch of shiny bits to attract attention, and make yourself feel fancy, until you can get your foot in the door.

Here's the thing though.  There's a difference between dressing up and covering up.  The first one is a celebration of what's there and all its potential, while the latter is about shame and denial.  You have to make sure that you love whatever boobage lies beneath the bra, because if Mr. Cleavage takes it off and you're embarrassed, so will he be too.  So have fun with it, love thy beautiful self, and always put your best boob forward.

Dear Jen,
I'm a virgin who's always been afraid of and nervous about sex.  Growing up we were made to feel that it was wrong, dirty, or dangerous, and that we should save ourselves for marriage.  But I'm ready now!  The problem is, I'm afraid that I'll suck at it.  I've read books on the topic and none of them really helped. Any advice?
- Virgin Jitters

Dear Virgin,
When I was in my very early twenties, I moved to Barcelona with a bunch of friends from college.  We lived like pigs, rocked and rolled all night, and partied every day.  Wine was cheap and, dude, you never got carded cuz there was no drinking age!  Fiesta dude!

One time I took the train to Naples, Italy, to visit my relatives on my Dad's side of the family.  I couldn't wait to rage in the old country with my cousin Valentina, get in on the local scene, bond with her, and maybe even hold each other's hair back while we puked in the Italian gutters together. 

Much to my horror, our big Saturday night out involved getting gelatos and strolling around the plaza, people watching.  If we were feeling especially wild, we'd go back and get ANOTHER gelato.  It was like going into detox, and as disappointed as I was, I couldn't help feeling a pang of shame every time we passed a bunch of staggering, American twenty-somethings, drunkenly screaming "oh solo mio" in the streets. 

Unlike American me, Valentina grew up with a bottle of wine on her dinner table, and, unlike me, was not met with a raised parental eyebrow and a "just what the hell do you think you're doing?"  whenever her under-aged hand reached for it.  This is why she was having wholesome, Annette Funicello evenings out, and I was on my way to waking up in the emergency room with a stomach pumping tube shoved down my throat. 

Desire + taboo = hysteria.  Be it booze, sex, expensive shoes, fattening food...whatever it is, if what we want is denied us, we obsess over it until we're either too freaked out to go near it, or we over indulge until we explode.

Between your parents and the negative messages our uptight society sends out, it's not surprising that you're having trouble getting started on the sex game.  But that doesn't mean there's anything wrong with you, it just means you got a little scared off.  And trust me, sex is a big deal for a lot of people.  I suggest you stop viewing it as this Thing you want to do, and start attaching it to a person that you trust and like.  Go on dates, find someone who gets you all hot and bothered, and then let nature take care of the rest.  Everyone had a first time, and nobody knew what they were doing, so don't freak yourself out.