Playboy (PLA) tends to be associated with the magazine and sex. Not the hardcore, nasty kind, of course -- Playboy has always been more than a tad distinguished, staying above board while the adult entertainment industry has chosen to compete in ways that my editor would delete if I even attempted.

With Iconix said to be interested in acquiring Playboy, it needs to think about where it can win with the ailing brand. The smart move may be to ditch the magazine and move away from sex -- it can't compete in either of these markets. Then, it needs to figure out how to make the brand relevant to everyone not in the Boomer generation ... or treat Playboy as an investment with a clock on it.

Looking for a 4,000-square-foot duplex with four fireplaces and a doorman on the Upper East Side of New York? You are in luck, because the U.S. Marshals will put Bernie Madoff's "luxury penthouse" on the market. The apartment is believed to be worth $7 million, so if you have some extra cash laying around, you could find yourself movin' on up to the Upper East Side. A list of the amenities includes ornate cabinets, stainless steel countertops, Baccarat crystal glasses, a winding staircase to the bedroom, an atrium breakfast nook, and a flat-screen TV in one of the bathrooms.

FriendFinder Networks has filed a registration statement with the SEC to raise $460 million with an initial public offering.

What is FriendFinder, you ask? The company operates a series of adult-oriented social networking sites including AdultFriendFinder.com. The IPO is of historical importance because it is, to date, the first time I've seen the word "Fetish" in an SEC filing. According to the prospectus, the company's ALT.com is a "Alternative lifestyle personals website, catering to users with fetish, role-playing and other alternative sexuality interests."

Apparently all this sexual networking stuff is big business. The company reports that for the nine months ended September 30th of 2008, revenue was $262.4 million with EBITDA of $66.6 million. The company hopes to use the proceeds to pay off the nearly half a billion dollar debt load it's currently carrying.

The timing is interesting because the IPO market is all but dead and leading adult entertainment provider Playboy (NYSE: PLA) is sucking wind (no pun intended) to say the least. But with a debt load as large as FriendFinder's, the company brass may have decided that it's too risky to wait for a better market.

When I heard that Penthouse was planning to launch a $250 million IPO, my first response was that it sounded like a great buy. After all, as long as America's stocks of 16-year-olds, hand lotion, and kleenex remain high, it seems likely that Penthouse will continue to do solid business.

Then I came face-to-face with a difficult realization: I'm getting old. You see, when I was a teenager, we didn't have the internet, pay-per-view movies, or a back room at my local video store. We relied on good old fashioned print pornography. In those days, Playboy and Penthouse were the two great porn magazines that were considered mild enough to be sold in bookstores. It seemed like every teenager in my high school knew about and coveted the divine publications.

Then the video revolution happened. Suddenly, everyone with a couple of bucks and a rental card could pick up movies that made Penthouse and Playboy seem quaint. When the internet came along, the stock of available pornography multiplied and magazines seemed positively prehistoric. Penthouse compensated by launching other ventures, including a casino, which met with little success. They also changed their content from the soft-focus pictorials of my youth to hard-core exploitative photography. By the end of 2003, the company had filed for bankruptcy, had shed many of its magazine titles, and was desperately casting around for ways out of its financial morass.

Penthouse Media Group has agreed to acquire the parent company of AdultFriendFinder, a website devoted helping adults find love -- or at least sex. The site is different from more mainstream (although AdultFriendFinder's traffic would seem to indicate its more mainstream that we care to think) sites like eHarmony in that the emphasis is on "hooking up" and there is little in the way of bragging about couples who met on the site.

According to the USA Today, Penthouse, which was acquired by Marc Bell and Daniel Stanton out of bankruptcy in 2004, plans to aggressively pursue acquisitions and possibly take itself public in the next few years.

Here's what's interesting: this is a company that owns social networking websites and was founded in 1996. It just sold for $500 million.