Confessions Of A Sugar Baby Seeking Arrangement

As the digital era continues to invade almost every facet of modern life, it was only a matter of time before the internet revolutionized the sex trade. Truthfully, the Supreme Court of Canada’s recent efforts to legalize prostitution were practically irrelevant to anyone who had already discovered Seeking Arrangement, an international website connecting sugar babies with sugar daddies. Nothing illegal goes down on the site, if you’re imagining escort-style profiles featuring hourly rates and a personal service menu. Quite the contrary. Instead, sugar babies, who tend to be 35 and under, attempt to make compelling profiles that justify their interest in  looking for a dream Freudian father figure—student debts and art projects and commonly referenced reasons for seeking “support.” On the flip side, sugar daddies, who tend to be on the older side of middle-aged, use their profiles to detail what they want out of a sugar baby arrangement (often a discrete and infrequent affair) while disclosing how they’d spoil their fantasy Lolita.

Some sugar babies shoot high—like requesting a $10,000 a month allowance—and some sugar daddies are willing to show that they’ve passed background check officially administered by Seeking Arrangement to prove that everything they claim adds up to the truth. What’s the catch? Given that Canadian users of the decade-old site grew by almost a third last year alone with McGill ranking second on Seeking Arrangement’s list of most active college campuses, we clearly don’t have a problem with it in the Great White North. At least behind closed doors. So is having a sugar daddy really the gift that keeps on giving?  We spoke to a Toronto-based sugar baby—who asked to remain anonymous while discussing her “mutually beneficially arrangement” experience with Seeking Arrangement—to get the real lowdown on what it’s like to have a daddy in the digital age.

How did you first start using SeekingArrangements.com and what prompted you to become a sugar baby?

I actually heard about it for the first time while reading Toronto Life, as strange as that probably sounds. I was intrigued by the idea that the woman in the article said she got together with her “John” maybe a couple times a month and he left her $500 or $600 as a parting gifts every time they’d get together without them ever really discussing money. He’d also buy her lingerie or champagne. She claimed she was into the sex and had a good time. She didn’t rely on it for her whole income but it just made her that much more comfortable, and her John liked to know she was comfortable. So I read all that and thought, “What’s the harm in making an account and just seeing what’s on there?” I have a university degree but I was in between jobs. And so I made an account that night and started messaging guys.

I’m sure people think it would be classier to just date someone who was well off instead of opting for a sugar daddy, but I’m not interested in deceiving anyone. I think it’s worse and more deplorable to make love conditional on a man’s bank account. That, to me, is ethically wrong. But being spoiled by a lover sounded great to me.

How do you know you’ll find a guy who will “pamper” you the way you want to be “pampered”? And did you care about meeting a guy you’d be attracted to and interested in being around or was it primarily about the gifts?

The site works a lot like a dating site. You fill out a profile and upload photos. Some people make themselves semi-unrecognizable. I just started treating it like a dating site, sending messages to the men I found the sexiest. There’s a section of the profile that asks for the range in value of gifts you’d expect to receive if you’re a sugar baby or would be willing to give if you’re the sugar daddy.

I met two guys I didn’t connect with and one businessman who was very attractive, but he actually messaged to say he’d changed his mind about the site (it was apparently his first-time cheating on his wife). The fourth guy I met, who was also married but considering leaving his wife, was really handsome and extremely witty, and even timid, which I thought was cute. He said he’d met two other girls on the site but one was much too young, like 22, and he thought emotionally she probably couldn’t handle it. The other woman gave off that she was a full-time escort. He didn’t want that. He seemed relieved I hadn’t gone through with any arrangements yet. We had tea together and talked for about two hours, exchanged phone numbers, and then we awkwardly hugged good-bye and he left. I was kind of excited that he wanted me to be his sugar baby. It’s a different feeling than somebody who wants you to be his girlfriend. It was a turn on. Was he married? Yeah. But he’d already made those moral decisions the moment he walked in the door and even before then when he signed up for the site. I played no role in corrupting him—that was already done.

What was your first “date” like?

He came over the following Tuesday. I made tea again, we talked, got to know each other better, and we just awkwardly waited for the other to make the first move. He eventually did. He was very romantic about the whole thing though — kissing my neck, slowly taking my clothes off, gently just outlining my body with his hands.

I guess even I wasn’t sure what to expect–like if he wanted a sugar baby because he needed to do something really freaky or maybe wanted really, really rough sex to counter his tender marriage sex. I didn’t know. But we had pretty lovey-dovey romantic sex with no real kinky stuff other than he wanted to suck my toes, which isn’t really kinky at all, but that was the extreme. We lay around in bed for a bit and then he asked if he could have a shower. He brought his gym bag which had his personal hygiene products in it so he’d smell the same as if he’d gone to the gym. He didn’t want to use my shampoo is all I’m saying. And I told him I’d actually been considerate enough to not wear perfume, which he acknowledged was a weird thing to thank me for doing. We kissed good-bye at the door. And then he said, “I don’t know how to do this other than by being completely awkward about it but here you go,” and he handed me an envelope. I said something like, “Oh my–riiiiiight! Thank you.” We laughed about it, and he knew from being over that I wasn’t exactly a rich girl. I didn’t open it. I just put it on the counter. We kissed good-bye and I closed the door. I remember waiting a minute or so and then opening it and there was even a card inside that he signed saying he was happy to have met me and $300.

How did your relationship with him play out after that?

He came over maybe once every two weeks or so, usually Tuesdays but the odd evening. We talked about life a lot. I knew he had two young kids and that his wife was actually more the breadwinner than he was, though he did quite well for himself too. He wasn’t happy though, and things had gotten so routine, and he was worried he hadn’t become any of them things he’d wanted to be in life.

I felt a lot like a therapist. We’d sleep together always, and it was always really good. I almost always had an orgasm too. As months went by, he’d even take me out for the odd dinner to spend more time together. He’d bring me gifts from business trips –just little things, not lingerie but teas, chocolates, and funny gadgets he knew I’d like– and he started leaving $400 in an envelope somewhere in my apartment.

Things slowed down when I found a full-time job and couldn’t meet on Tuesday afternoon. He came to see me before he went on a family vacation for a few weeks — a trip he’d been dreading. We emailed while he was gone but when he got back he just stopped writing. I wrote him after about six weeks just to say hello and see how he was. He apologized for being MIA, that things had been “complicated” at home. I said I understood (assuming he was likely working stuff out with his wife) and that it was fine and that this was obviously the whole idea of the arrangement — no need to apologize. It was a respectful end actually.

Did you get another sugar daddy right away or did you stop because you were working?

I had one more sugar daddy for about half a year after that. He was an out-of-town businessman who came to the city at least once a month. I’d meet him at his hotel. He wasn’t as sexy but he was fun and I loved hearing his marketing exec stories. He’d always slip me an envelope with $500 and another $100 gift certificate to either a clothing store in the Eaton’s Centre or Victoria’s Secret. I was actually the one who stopped being available, and he clearly just moved on to someone else. He was also married with a family, but I got the sense that had a girl in every city he traveled to. When I pictured that, I stopped wanting to do it. It wasn’t about ethics. I just thought the likelihood of getting an STD like herpes or genital warts –something that condoms don’t protect against– would much higher with someone like that. The $500 didn’t seem worth risking my future sex life over.

Do you feel like this experience compromises your values as a feminist in any way?

No. I was assuming a submissive role in a sexual relationship, sure. But does it compromise my ethics? No. I’ve never placed that much importance on sex other than that it’s fun. It’s not a relationship-only thing for me, though I have always been faithful to boyfriends. The truth is, of all the jobs I’ve had, I’ve compromised my ethics more by working for corporations that were ruthless in terms of the taking advantage of situations for their own financial gains. As far as love goes, I’m a realist. I think love is possible, and I think sometimes relationships morph even though the family stays together. Would I be mad if my future husband used Seeking Arrangement to meet a sugar baby? That depends. Do I have a sugar baby of my own at this point? Sugar Mommas are a thing on Seeking Arrangement too, you know?

What are your thoughts on Seeking Arrangements, sugar babies, and sugar daddies? Let Vv Magazine know in the comments below or tweet us @ViewTheVibe.