Leighton Meester’s family history just seems to get more and more complicated.

The 22-year-old Gossip Girl starlet, aspiring songbird and sneakers shiller—who was born while her mother was serving a prison sentence for drug smuggling—has a brother who’s also seen his share of legal troubles, according to Denver Westworld.

According to the paper, Leighton’s bro, Douglas Meester, was accused of rape while he was a teenager attending the Air Force Academy. A series of articles penned by Westworld writer Julie Jargon detail how Douglas—then a sophomore at the Academy—was accused of raping and sodomizing fellow cadet Justine Parks, then 18, in 2002, after the two had a drunken, intimate encounter.The involvement of alcohol, however, led to confusion in the case. “Parks says she was too weak to resist and doesn’t recall ever saying ‘no,’” Jargon writes. “However, she told investigators that she ‘knew for a fact that he probably thought what we were doing was consensual.’”

Even so, perhaps because the Academy was in the midst of a sexual-harassment scandal, “new commandant of cadets Brigadier General Johnny Weida ordered the court-martial for Douglas Meester…even though the Article 32 hearing officer recommended against it, saying there was insufficient evidence.”

Meester eventually cut a deal in June 2004, pleading to conduct unbecoming of an officer, dereliction of duty and committing an indecent act in exchange for the rape charges being dropped. The teenager was fined $2,000 and given a written reprimand—far lighter than the potential life sentence she might have received had he been convicted of rape.

Speaking of Leighton, the gal who plays Blair Waldorf graces the cover of the March 2009 Seventeen magazine and discusses her taste in men. “I think guys who are rebels and make their own rules are appealing,” Meester says. “I don’t want to tame anybody. I want them to be dark and bad.”

Not that she’s all that hung up on dudes, she adds. “I haven’t ever really relied on relationships with guys,” she notes. “They come around and it’s cool, but it’s never been a big thing. I guess I’ve just been really distracted by work.”

Hmm. Wonder how Meester’s current beau—and possible fiancé—Sebastian Stan feels about that.

Source: Celeb Buzz