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Resist urge to secretly film hot roommate

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My roommate is astoundingly hot. Her room is being repaired (the ceiling fell in), and, at her request, I'm letting her and her boyfriend sleep in my room while I take the couch. I've been able to contain my attraction just fine up to now, but the minute she entered my space I had this feeling that all bets are off. I'm considering spying on her with a hidden surveillance cam. If I had video of this girl naked, let alone being fucked, I could happily beat off to the footage for the rest of my life. Obviously it's a breach of trust, and I'm a shitty roommate for considering it. I have a few concerns. Is this normal? Assuming that there's no way she could find out and that I kept the video to myself and myself only, would it be so wrong? What is her reasonable expectation of privacy once she enters my room?

Thanks In Advance

Before we get to your tech-related queries, TIA, a word about a young man in Florida with tech-related troubles.

America's current teen-sex panic -- it's always something -- is about "sexting," teenagers sending each other pictures of their sometimes-underage junk, their frequently underage racks, or their young and dimpled/pimpled rear ends. (Oh, if only we could return to the comparatively innocent and entirely fictional days of "rainbow parties"!) Shortly after the kids went crazy for sexting, the authorities went crazy for prosecuting kids for sexting. Take Phillip Alpert, an 18-year-old in Florida who got mad at his girlfriend and forwarded a digital photo of her naked to dozens of her friends and family.

This Alpert kid (he had only just turned 18) pulled an asshole move, and he owes his girlfriend, her friends, and her family an apology, restitution, and a pound of flesh. (And I mean that pound.) A just, proportionate punishment might involve, say, nude pictures of Alpert being displayed on a billboard in Times Square. For a year. Instead, Alpert was convicted of distributing child porn and "sentenced to five years probation and required by Florida law to register as a sex offender," CNN reports. "You will find me on the registered sex offender list next to people who have raped children, molested kids, things like that," Alpert told CNN.

A message for concerned parents, outraged school officials, and teen-sex-obsessed prosecutors: We're gonna have to either make it illegal for teenagers to own camsphonescomputers, or we're gonna have to give them drugs to delay the onset of puberty until after they're 18. If we're unable or unwilling to do those things -- technology is hard to contain, and delaying puberty could have unwelcome health consequences (although it would have spared Levi Johnston's DNA from the ignominy of mixing with the Palins') -- then the intersection of horny teens and newer technologies is going to require us to rethink the simplistic application of laws that criminalize the possession and distribution of sexty (ugh) pictures, particularly in cases where they were created by teenagers, for teenagers.

Yes, Alpert was a douchebag; yes, it was wrong for him to forward that picture to embarrass and humiliate his girlfriend. But if Alpert is a child pornographer and a sex offender, so are millions of today's teenagers. They're all e-mailing each other pictures of their junk. Making an example of one unlucky asshole who got caught isn't going to stop teenagers from sexting each other anymore than making an example of hundreds of thousands of unlucky pot smokers stopped people from smoking pot.

Okay, TIA, on to your question: While it's normal to contemplate, even obsess about, something you know is wrong, secretly videotaping your roommate, even if she's "in your space," isn't just an asshole move. It's an illegal move in most places, and the consequences for asshole moves involving digital images, as illustrated above, can be dire. And until submitting to video surveillance is widely understood to be a known risk of sleeping in someone else's bedroom, your roommate and her boyfriend have an entirely reasonable expectation of privacy.

As for no-way-she-could-ever-find-out, I could sneak into your house and use your toothbrush, and you'd never find out. And although it would hurt me more than it would hurt you, TIA, it would still be wrong -- even if there was no way short of DNA testing that you would ever find out. And while you may intend to keep the video to yourself -- such the gentleman -- what if your laptop gets stolen? What if you take your computer in for repairs and someone makes a copy? Digital images -- photos, video, whatever -- are too easy to lose control over.

Don't do it, TIA.

I'm a 24-year-old guy, and I just got a blowjob from (and gave a half-assed one to) a transsexual male-to-female prostitute. It was no accident: I'd spent about two years looking at TS porn (as well as regular guys-doing-it-with-girls porn), and the whole thing seemed like a hot idea. But the plastic-surgery scars around her tits and her cock in my mouth kind of made me nauseated. I went through the motions only because I didn't have the guts to walk out. (We both had condoms on.)

I'm not sure if I can face my girlfriend of a year. I've been faithful to her until now, and I feel like crying. I don't know if it's because it was illegal (prostitution), because I was cheating on her (unfaithful), or because I can't say I'm totally straight anymore (cock in my mouth). I don't know how to tell my girlfriend. She knows I look at porn, but she doesn't know I look at TS porn -- no one does.

Regrets About Gay Experience

Paradoxically, RAGE, going down on a shemale escort shores up your heterosexual bona fides. Gay guys don't frequent and/or fellate shemale escorts (on purpose or by accident); getting with shemales is an entirely straight-male pursuit. So you can go right on identifying as straight, RAGE. Of course you aren't totally straight -- try thinking of yourself as something more than straight, not less -- but you're close enough that you can round yourself down to straight with a clear conscience. (Offer void the day you start blowing hemale escorts.)

As for the rest of your angst: If you're serious about this woman, then cheating on her like this was a shitty thing to do. But you're not married yet, RAGE, and now's the time to get out there and satisfy any outstanding sexual curiosities -- before marriage and before kids. And while unburdening yourself to the girlfriend may sound like the noble thing to do -- honesty being the best policy and all -- each of us gets to take at least one big secret to the grave. If this truly was a one-time, lesson-learned, never-again experience, let it be the secret you're buried with.

Finally, RAGE, good on you and your escort for using condoms. But there are a whole host of sexually transmitted infections you could've picked up from her, condom or no condom. Make whatever excuse you need to in order to get out of having sex with the girlfriend, go get a full STI screening, and refrain from having sex until you get the all clear from your doctor.

Download the Savage Lovecast (Dan's weekly podcast) every Tuesday at www.thestranger.com/savage. To ask Dan Savage a question, write to mail@savagelove.net.

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