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"The Internet," says California criminal defense attorney Bruce Nickerson, "is an enormous trap for the unwary." Nickerson should know: He specializes in defending gay men accused of sex-related crimes, and over the years the number of Internet-generated cases crossing his desk has grown steadily.

Online police stings are nothing new, of course. But the popularization of digital imaging technologies over the last few years has added to the number of ways an Internet cruiser can find himself doing something illegal without intending to. The potential for a long and unpleasant tangle with the law, perhaps ending in a prison term, is real-- especially for gay men, who have been among the fastest to adopt the webcam as their sex-toy-of-choice. On the other side, Nickerson notes, a 2002 Supreme Court decision has made it easier to defend against certain types of charges involving "child pornography" that depicts no actual children.

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Cyberspace 101

First, a quick review for anyone who has been asleep or under a rock for the last decade: while the Internet is full of people of all ages seeking sexual thrills, it's also crawling with undercover cops. One of those cops' favorite tricks is to pose as an underage males or females in order to arrest people who solicit them for sex. While some of these cops' behavior starts to look an awful lot like entrapment to the casual observer, most have been well trained to stay just within the bounds of what the courts have deemed permissible.

Whatever one's beliefs about the morality of such things, engaging in sexually explicit chat with a person who claims to be underage is always-- repeat, always-- dangerous, regardless of how sexually experienced or plain horny the person claims to be. So is sending sexually explicit material to an apparently underage person. And, of course, possession or transmission of anything meeting a legal definition of "child pornography" is highly illegal and risky.

Simple enough, it seems. But now that everyone and their mother (or child) has a digital camera and a webcam, the potential legal risks have multiplied. Some very large chat systems, such as Yahoo, now allow participants to view others' webcam broadcasts with no special software. A couple of mouse clicks, and presto, you're looking at whatever your chat-buddy cares to show you-- which may be an anatomical region located well south of his face.

Amazingly enough, not everyone taking advantage of these technological marvels has reached the age of 18, and that fact creates a whole slew of potential legal puzzles. For example, if a 15-year-old uses his digital camera to take a picture of himself with an erection and then posts that photo on his online profile, is he guilty of distributing child pornography? What if he uses the webcam he got for Christmas to send images of himself jerking off?

On strictly legal grounds, the answer in both situations is almost certainly yes: our hypothetical teen has committed a criminal act by distributing erotic images of himself. But the consequences might not be severe, says Nickerson. "It's up to the discretion of the prosecutor. Chances are it'll end up in juvenile court, the judge will roll his eyes and tut-tut, but not make a cause celebre out of it."

However, an adult watching the images this hypothetical teen is broadcasting might not get off so easily. The pictures he's sending are absolutely illegal to possess, and if you find yourself receiving images that seem dubious, Nickerson advises, "Immediately stop."

But disconnecting immediately may not be enough to guarantee you are not in possession of illegal material and thus in potential jeopardy. As any number of unfortunate Web-surfers have discovered, even briefly-glimpsed images or fragments of chats that no one ever tried to save can find their way into unused space on your hard drive. Prosecutors can and will use sophisticated software to retrieve such material for use as evidence, even if it's fragmentary or incomplete.

Keeping one step ahead

The only way to absolutely be sure your hard drive is free of anything that shouldn't be there is to use what is commonly called a "shredder" program. Several different firms make such programs, which overwrite every millimeter of hard drive space that isn't in current use with nonsense data, obliterating whatever had been lurking there. Because it is so easy to encounter illegal material without intending to, Nickerson says, "any person who surfs for porn, even legal porn, should have one and use it."

In many cases, the age of the person whose image you are viewing may not be clear-- and, of course, you can't count on people in online chat to tell the truth.

That is where last year's US Supreme Court ruling in the case of Ashcroft v. Free Speech Coalition comes in. In that landmark decision the court invalidated the Child Pornography Prevention Act of 1996, which had greatly expanded the reach of federal child-porn statutes. The CPPA banned any image which even "appears to be" of minors engaging in sexual conduct-- including completely computer-generated material as well as images of young-looking adults. Under CPPA, a person could be convicted of possessing child pornography even when there was zero evidence that the material depicted anyone who was underage.

That was too much for even a conservative court, which concluded that the CPPA criminalized large amounts of constitutionally protected communication. The ruling has put the burden of proof back on prosecutors, who need to have evidence that the material actually involves minors.

But what of the adult using his webcam to show of his, uh, assets? How cautious does he need to be? Knowing that the Net is full of both actual kids and cops pretending to be kids, the simple answer is very, particularly if you are carrying on in a chat room that is frequented by minors.

"My recommendation for an adult in a chat room is this," Nickerson says. "If someone announces they're under 16, every adult in that room had better reform themselves right then and there, otherwise they could get in trouble.... If you are in a chat room for teenagers, you should act as if you are at a kid's party and their parents are watching." Conducting any sort of suggestive interaction, visual or verbal, with a person who has said or even implied that he is a minor is asking for trouble.

But the law does not require you to demand ID and inspect birth certificates. "If he says, 'I'm 18,' you're fine," Nickerson explains. In such cases the law frequently invokes what is called a "reasonable person" standard: It's reasonable to assume someone is the age they claim to be, unless other circumstances suggest differently.

It's also reasonable, when cruising online, to be very, very careful.