Getting a sugar daddy

Female, 30, Edgewater
I was 25 when I first went on a sugar-daddy website. I thought, As long as I’m safe, and I don’t get arrested, there’s really no downside to this. I made a profile like any other dating website, but for this, I was asked things like how much compensation I was expecting per month. You had to describe your personality and your ideal sugar daddy. I said, “I would really like a very affectionate and generous older gentleman.” I really didn’t want somebody my own age; I felt that would be weird having somebody young who was also paying me. I put up real photographs of myself: two that showed my face and a sexy full-body shot where I was wearing a corset and stockings that I had taken for an ex-boyfriend. If only he knew!

Half of the guys who responded didn’t have photos but finally I saw one who did…it looked as if he was at a ski lodge, holding a dog. He said he was five-foot-ten, 43, slightly graying hair, athletic build, and told me how much he made and his net worth. We e-mailed back and forth a little bit, very much as you do on a dating site. We decided the first time we’d meet in the suburbs near his place. We were planning to just have dinner, and if things went well, who knows what might happen? I showed up at the restaurant in a knee-length skirt and a sweater—I was not sexing it up at all. I wanted to make sure if someone saw us, they wouldn’t immediately go, “Oh, these are the kind of people that would hang out at Viagra Triangle.” I was relieved to see that he was a very normal-looking guy. He was not overweight by any means, but kind of a big, bear-built guy. It made me a little nervous because he was stronger than me.

We started talking about everything except sex: politics, current events. After dinner he said, “Would you be interested in going back to my place?” I said yes, and then he said, “Oh, here,” and he passed me an envelope across the table. Of course, I knew what this was, so I peeked in—there was the $250 I had asked for before the date.

The sexual tension built between us as we were going up to his swanky condo, and we ended up making out in the elevator. I realized then that I was kind of attracted to him. Once inside, we went to the sofa, making out like teenagers. I started stroking him through his boxers. My clothes started coming off really quickly. I said, “Would you like to take this into the bedroom?” He had a big smile on his face and said, “That would be great,” because he knew I was definitely interested in going through with everything. I immediately went down on him. He was rock hard. I was like, Thank God he doesn’t smell, another big worry of mine. (We also had that STD- and HIV-testing conversation before we met.) I put a condom on just using my mouth—that always makes the medicine go down a little bit easier. I got on top of him slowly. He went inside me and ended up rolling over, doing more of the work. There was kissing, and it was very much still romantic, looking into his eyes and stuff. He definitely came from that, and I actually had an orgasm—I was thrilled about that. I certainly wasn’t sitting there, as they say, “thinking of England.” We spooned afterward, and when I got up to leave I said, “I had a wonderful night; I really hope we get to do this again.” He goes, “We’ll definitely do this again. Can I give you a call this week?” I walked away feeling excited and happy having that money in my pocket. But also a little bit sleazy. This guy just paid me to have sex. Even though it felt wonderful, even though I had an orgasm, and even though there was cuddling, this still was business and this guy is not interested in dating me; he’s interested in having a sugar baby.

FIRST TIMER’S TIPS * If you get a bad vibe through e-mail or phone calls (which you should have before you meet in person), or he immediately jumps into talking sexually, don’t do it. You want to have some sort of connection, because you will likely go out to dinner. * Call a friend ahead of time and let her know where you’re going. Get as much of this guy’s information as you can. Call your friend while on your way there and say you’ll call her on the way back, too. * Bring condoms and lube—who knows if he’ll have them. * Don’t be scared to get the money up front. Say, “Didn’t you say you had a gift for me?” Legally, you can’t be arrested for having a generous boyfriend.