One day a few years ago I was at my boyfriend’s place, lying naked on his bed after sex. He’d gone to shower, and when he came back he found me stretching on all fours, ass in the air. “Oh, God—don’t move,” he said. As I looked over my shoulder, he aimed his iPhone at me—and all of a sudden I was in my first nude photo shoot. When we flipped through the results minutes later, I was so turned on that I climbed back on top of him.

Taking dirty pictures wasn’t something I ever thought I’d be into, but I’ve done it with both men I’ve dated since. (Happy blackmailing, guys!) For most women, in fact, a steamy first-time experience can be a revelation that leads to a whole new sexual world. Sometimes we just need a nudge in the right direction.

Of course, for every sexual initiation that’s a wild success, there’s one that goes wronger than wrong. You don’t want to be remembered as the guy who busts out the inflatable sheep on the first date. So, to find out which experiments are likeliest to bring her back for more, I had dozens of women describe their hottest—and most disastrous—first times. If your girl hasn’t checked these rites of passage off her to-do list, take the lead and become her sex guru.

Girl-on-Girl
As trendy as bisexuality has become, plenty of girls are still squeamish about putting their lips on another woman’s, well, lips. But every woman I interviewed who’d tried it, loved it—even if they haven’t done it again. “I still get wet thinking about the night Jackie and I hooked up,” says 26-year-old Carlee*, who slept with her best friend after confessing to her boyfriend that she was curious about being with a girl. “Her body was so soft, and hearing her moan got me so turned on. But I’m happy with my boyfriend. I satisfied the urge, and now I just use the experience to work myself up.”

But this experiment can be tricky, especially if you decide to participate. “The way I imagined a ménage à trois was different than the way it turned out,” says Alex, a 29-year-old boutique owner. “My boyfriend Rob said I should tell him if I was uncomfortable, but I didn’t want to be a killjoy. So I just watched him hook up with this girl we’d met at a party, feeling sick the whole time.” They broke up shortly after.

And there’s always the chance that she’ll dis­cover she enjoys bedding another woman more than she enjoys bedding you. “Women in these situ­ations can find out things about their sexual preferences that are threatening to their male partners,” says Lou Paget, author of The Great Lover Playbook. In other words: Encourage her at your own risk. If she goes Lindsay Lohan on you, it’s your own damn fault.

Sex on Camera
As I discovered in my personal photo shoot, even shy girls find something incredibly alluring about being the star of the show. “I was fooling around with the camera on my new phone when I accidentally zoomed in on my cleavage—and thought it looked super hot,” says Sari, a 31-year-old teacher. “It inspired me to strip to my underwear, and then I started shooting myself masturbating. The grainy video was awesome because it concealed flaws and made everything look really raw.”

For others the distance a camera provides can act as an aphrodisiac. “When my boyfriend and I watched the first sex tape we made, I felt disembodied from the experience—but in a good way,” says Serena, a 29-year-old pharmacist. “I didn’t feel self-conscious, because it was almost like looking at someone else.”

But there are caveats. To make your girl feel secure, film in her home and make it clear that you’ll store everything on her computer. “My ex’s doofus roommate borrowed his laptop and found the video we’d made,” says Natalie, a 28-year-old bartender. “We found out that he called his friends into the room to watch, like he was the geek in Sixteen Candles. I felt majorly violated.” Promise her you’ll be the only two pervs viewing your special video—or just delete it afterward, sickos.