Honestly, why are the dudes on Sugar Baby sites so freaking impossible? 

 Treasure in Georgia 

He told me never to write a story about us. I told him not to worry, my voice like a soft, reassuring hand on top of his. 

Treasure and I met on an app built for older men to find younger women willing to spend time with them, often intimately, in exchange for expensive dinners, gifts, or cash. A sugar daddy/sugar baby site. I’m on it because I need money, he’s on it because he got an itch to cheat on his wife again. He admits this, frankly, in the third message he sends on the app. 

He’s brusque, a Jewish ginger with a serious New Yawk accent. Armed with a scumbag vocabulary which seems to be his first language, he objectifies women, but he can also discuss the poetry of Adrienne Rich, and has seemingly endless cultural knowledge. He’s a member of etiquette-driven New York City social clubs, but says he’d kill someone who ever wronged his daughter. Treasure is the perfect mix of predatory salesman and cultured charm; he’s curious, brilliant, anxious. Macho and soft, classically ugly, he is surprisingly sexy. My Anthony Bourdain dream man. I think I’m in love with him. 

But love is never simple, and Treasure’s unique brand of paranoia creates exquisite barriers to intimacy. For instance, email is the only method of communication we are allowed. 

I have his phone number, he ended up calling me one night, drunkenly looking for me at the bar “Where are you?” But using his phone number is forbidden, and I respect this. “I have a random schedule, what if I’m at the movies with my wife in the afternoon and you text me saying you need me inside you?” He explained early on. Treasure has an excuse for everything. The way he delivers them like a smooth sip of something makes me swallow them without much thought. 

On our first date he’s visibly nervous. I am too, and rightfully so. I’ve agreed to meet a stranger off an app, and I don’t even know what he looks like. Treasure’s profile picture on the site is a shot of a turquoise oceaned beach, with a man walking on it, his back turned to the camera. It could be him, or it could be anyone. I never asked to see a picture. I guess I didn’t want to know. This isn’t about looks. 

My first glimpse of Treasure is on the corner of Bleecker and Crosby in SoHo. He’s not at all what I expected, but then again, it could be much worse. He’s just like... somebody’s dad. I breathe and remind myself how freeing it would be to not have to worry about rent. To not dive deeper and deeper into credit card debt. I’m here to get paid to play and I don’t feel I have much to lose. 

We circle SoHo for an hour in the rain, while Treasure insists on holding my umbrella over me. I “haha” at his jokes and my feet start to rub and blister. Every time we come upon a bar, he comes up with a reason why it’s not the right fit. He talks fast and his eyes dart around, always looking to avoid someone he knows. Finally, we end up at a tourist pub. His anxiety is palpable, like the sweat building under my too-tight jeans. We order gin and tonics. I specify “Hendricks” because I know he’s paying. 

“You’re hot, but not too hot,” Treasure says to me. My eyebrows raise as I sip my drink. “That’s good, because it looks less weird for me to be out with you,” he explains. I realize he means I look natural, classy, not too obviously like a girl you’d pay for sex. This makes me feel like I should’ve worn more makeup. Like my whole life would’ve been different if I just knew how to style my hair into a look. 

I inquire about his experiences on the site, and he adamantly tells me he’s never done this before. He has cheated on his wife before, yes, but never like this. “When you start hiring prostitutes, your game is over,” Treasure proclaims. A sugar baby/sugar daddy dynamic must seem different to him. To me it’s just a prostitution rebrand, something to make paying for sex more palatable for ego-driven men. 

I’ve never done this before either, but I’m broke in a way I’ve never been broke and weighing what I can withstand in order to survive. Treasure seems suspicious, like I’m a scammer, a professional slut. I think that’s who he meant to order on the Sugar Baby site. But instead he got me. Up until our meeting, his messages have been crude, centered on fucking and sucking. He’s thrown off, perhaps ashamed he has been talking to me that way and unable to make a swift recovery. 

After two rounds of gin and tonics and stilted conversation, Treasure walks me to the train. I feel pretty sure I won’t see him again, but before I descend into the subway, he asks me if I’ll step aside, off the busy sidewalk. He makes it a big deal, a dramatic gesture. “On the count of three, let’s whisper our real names in each others’ ears,” he says. Neither of us use our real names on the site. 

He counts to three. I smile at his earnestness. We take turns revealing our names to each other, through subtle whispers. When his hot breath hits my ear, I shiver. His real name humanizes him somehow. 

After the chill inducing name trade, I put my cards on the table, and send Treasure a half nude photo. We joke about our fake online identities, and how bold a move it was to swap real names. I’ve only ever been truly interested in girls who I wanted to fuck and learn everything about. To know you inside and out… Treasure writes to me. 

Arranging our second date via email, I comment on the fact that it’s forecasted to rain again. Treasure responds, “I’m taking it as a sign that I haven’t been able to interpret yet. If you let me know what train you’re taking, I’ll definitely meet you with an umbrella like a hero.” I tell him I’m an independent woman, but thank him for being a gentleman. His annoying charm is starting to weaken me. 

Treasure promises an incredible night, and I tell him I’m game, at least until my plan with a friend at 7 p.m., when I assume he must be home for dinner anyway. He suggests we get drinks at Macao Trading Company. On my walk from the J at Canal, I witness multiple men stare at me in a way I recognize. A part of me I wish didn’t exist is proud I’m playing the role of professional slut better today. 

Over pineapple-infused cocktails, Treasure proposes we find out if our physical chemistry matches our intellectual vibe. I’m feeling the drink, so I offer to meet him in the bar bathroom to make out. He shakes his head, as if that is a crazy idea. “I had to shower before I met you today, so I grabbed a room right by here,” he says, as if that’s a totally normal thing to do. I bite into the pineapple garnish and internally chastise myself for not eating lunch. My immediate buzz is hindering my better judgment. 

Surprising myself I agree to Treasure’s proposal, but only under three conditions which I proclaim too loudly for his taste: You have to promise not to kill me, you have to promise to pay me, and I can only stay for seven minutes, so I can make it on time to meet my friend. Seven minutes in heaven. 

Thanks to my buzz I don’t think too hard about anything on the walk to the hotel. I’m in an unfamiliar part of downtown Manhattan, way on the westside. Coming out of a dark bar into the light makes me feel like I’m a different person in a different city. Nothing feels real. Which makes the next part much easier. 

We enter the hotel lobby, which is nice, thank god, and I glide through like I’m Julia Roberts in Pretty Woman post-makeover. I’m ready. Ready to get killed, ready to get tortured and then killed, ready for anything he might pull. Inside the room, I don’t waste any time. I place my belongings on the desk, and shoot him a look. I take three steps toward him and he takes one step to meet me. Our lips collide, entering the kiss with some speed. I press my chest against his, put my hand on the back of his head. Something clicks. I realize I’m not performing. He’s a good kisser and I don’t want to stop. 

He pulls me down on top of him on the bed, my legs open over his waist, and I start grinding into him while he cups my breasts. He brings his face to my chest and I can feel his hot breath through the mesh triangle on my shirt cut over my décolletage. He kisses my nipples through the thin layers of fabric, and I rub my breasts over his mouth while gripping his shoulders. 

Seamlessly, he scoops me up from my haunches and now I’m straddling him on another surface. He’s against a flat back, upright, so our lips are aligned. I want his mouth on mine, I lean in, kissing and grinding on him, and I feel myself getting incredibly wet, my pussy lips electrified, clit pulsing, my hips moving over him. I want him inside me more than I reasonably should at 5:30 p.m. on a Tuesday. I’m suddenly overwhelmed by it all, caught off guard. I’d wrongly assumed I’d have to summon desire for him, but instead, I’m overcome by it. I tear myself away, untangling our limbs and reclining on the bed to study him from a distance. 

We look at each other, breathing hard. His face is worried. 

He starts talking, in concerned, soothing tones. He tells me he doesn’t want me to feel like I have to do anything physical with him. He says we can just be friends. That he’ll still help me with money. It’s all so fatherly and unexpected, I’m hit with a wave of sadness. I wonder if he really cares for me or if he’s protecting himself. I know I’m falling for him anyway. My eyes well up; daddy stuff really gets me. 

“I’ve been thinking a lot about yesterday.” Treasure emails me after our hotel room hook up. “About how good you felt and tasted. About how your rhythm felt like I’d done that with you 1,000 times. And about all the weird coincidences that keep happening. All the rain... I can’t decide if I hate the way I met you or if I should own it. Find a way to be comfortable with someone in a different dynamic than anything I’ve been involved with before.” I read his email over and over. Show my friends. Get that happy sinking feeling in the pit of my stomach, the feeling of being excited about someone. 

We’ve started to email a lot—it turns out Treasure is a good writer. He’s witty, and makes me laugh. He’s much more interesting than the other old married dudes on the site. One guy I’m entertaining texts me all day, every day, which feels like a terrible full time job. When I apologize to Treasure for taking 24 hours to respond to an email, he assures me, “Don’t worry about the delay. Of all the guys you’re currently involved with, I need the least sunlight and water to survive.” Perhaps this coolness is what initially endears me to him. 

He adores my venture as an erotica writer, calls me a legend, gasses me up at every turn—not only when I send him nudes. He relays networking strategies and ideas for how to grow my business. He calls me “his girl,” his “online crush,” says we have “a serious connection.” Treasure tells me this is the most exciting month he’s had in years. I choose to believe these things. The sweetness in place of the sugar. As my feelings grow, things start getting complicated. 

Our affair is not falling into place—we’re stuck in a routine of daily emails and weekly meetings at bars. We haven’t been alone together since our seven minutes in heaven. I haven’t seen any sugar since then, either. The idea of paying for my company ruins the game for him, but he has a wife and family who will always come first, and I know I’ll only get hurt if I enter a starry-eyed romance instead of a business deal. We both want more than we can fairly have of each other. 

Meeting someone the way we did turned out to be a lot for me to unpack. I’ve got to be honest. Maybe I’m messing things up on purpose to sabotage myself? Maybe I’m just selfish? 

I listen to “Money, Power, Glory” by Lana Del Rey on repeat in the shower. I’ve all but given up, when Treasure surprises me in Greenpoint at a backyard bar, late night, much past dinner time. It’s humid out, my legs are itchy from mosquito bites, and I feel the ageless summer thrill of possibility. His eyes dart around the small crowd, like usual. I’m compelled to soothe him. 

As I stroke his beard, I ask him if he really likes me. I want some kind of validation that he can’t give me. “Why would I risk my life for someone I wasn’t that into?” Treasure asks. I’m more confused why he’d risk his life just to hang out with me, without even getting to fuck. I’m also not sure why I’m pursuing him when all he offers me in trade is drinks in Brooklyn dives. Even at my poorest, those aren’t high on my most-wanted list. Nevertheless, I lean in to kiss him. He turns his head. “You know I can’t kiss you here,” he says. 

We leave the bar and I pull him into the park down the street. There’s no one there, it’s midnight, but he’s still afraid to kiss me in public. I’m too drunk to care. I push him down on a bench, straddle him, and lift the bottom of my dress up, showing him what he’s missing. “Let’s get a room,” he begs me, but I want to be under the stars, in the moment, and ultimately, maybe I’m afraid to go all the way with him, too. I want him only where I can’t have him. 

I kiss him, and he gives in a little, before pushing back moments later, making me push harder into him. We battle. In this moment, I want him so badly, I’d fuck him right there in the park, unzip his pants and bring his cock out, make sure he’s ready with long strokes, then lower myself onto him, moving my wet panties to the side. 

He interrupts my attempts, sits me down next to him, looks at me seriously, “We can’t here.” 

He leads me to the corner to send me home in a car. As we’re waiting for it to arrive, I take a dare. Right on the street, a forbidden space, I line my body up with his, and press into him. Legs touching legs, belly to belly, my tits on his chest, his face dips so his nose and mouth align with my neck. He stays there for a minute, breathing me in. It feels... incredible. I go home, panties wet. Dream of him. Wake up, refresh my email. Smile at his words. Fantasize about when I’ll see him again. Wonder if we will ever fuck or if all he wants is to feel wanted by me. If all I want is to feel wanted by him. 

“This morning I woke up thinking about how it felt when I pressed my body against yours on the street last night,” I write in an email to Treasure. “Then I made myself cum three times, imagining you watching me and jerking off, me on the bed, you standing at the foot of it, me telling you that you can’t touch me, only watch and touch yourself, but when you’re ready to cum, to cum all over me.” 