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Editor's note: in this new series of personal essays, each month a different writer will describe a complicated sexual first.

Ray was a friend of one of my exes. We were half-naked in my bed, hovering between would we or wouldn't we, when he whispered he had something to tell me. I thought: girlfriend, disease, disfigurement. Earlier in the evening, Ray had agreed to leave a party, where we weren't having fun, and go to a bar in the Mission and act like he was interested in me. The idea was to make my most recent ex jealous. But he wasn't there, so Ray and I settled into date-like flirting. I apologized for asking him to be my decoy. He didn't seem to mind.
    I felt comfortable around Ray. We had lived in the same college town, though I didn't know him then. He was broad-shouldered and shyly confident, with a square jaw and soft greenish-brown eyes. We talked about politics and his last lover. He awed me by describing how he'd thrown a TV through her front windshield when they broke up. It made my lame attempt at vengeance look even more pathetic. I admired Ray's wildness and wondered why I couldn't provoke that kind of destruction. During a cozy silence, Ray held my face, kissed me. After a few more tequilas, I took him home. In my bed, he moved on top of me, shirtless and smooth. We kissed and pressed together, but before he undressed me completely, he shook a little, his eyes looking for mine in the dark. I'm a male hustler, he said.

    I maneuvered out from under him, not understanding. He explained that he got head from men, then got paid. No reciprocation. No penetration. As we lay in the dark, he told me a few details: the first time he'd done it, he was eighteen, hitchhiking and broke. An unassuming man drove him back to college and offered him a wad of cash if he could blow Ray. Close to ten years later, he still did it for cash. Only for the cash, he said.

    I wasn't scared so much as fascinated. I wanted to know everything: Do you have a drink first? Do you shake hands after? Will they pay more if I come watch? Voyeurism had always turned me on, but this presented a whole new set of sexual configurations I'd never even contemplated. I soothed him, then thought: safety. Ray assured me that he'd been tested and that there was a slim chance of catching anything — he went into men's mouths, nowhere else. I kissed him, hesitated, found a condom. He pulled out before he came.
    Ray's confession didn't dissuade me from wanting to have sex with him; it somehow attracted me more. Having recently been rejected, I found myself in a position of power, and I liked it. Over the next few weeks, Ray told me more specifics of his tricks and, more importantly, what went through his mind when men were going down on him. Often he'd think of me and the wild sex we'd had earlier. I liked that he remembered it that way. He'd tell me that when he was in someone else's mouth, he'd imagine how I felt when he entered me, pretend it was me surrounding him. When he'd describe how he imagined us fucking when a strange man was unbuttoning his pants, I'd start undressing him. I had become part of the transaction. This, I thought, was hot.
     As I probed Ray's history, I found out what else he did for money: fuck women in front of men who'd pay them. Two hundred dollars, at least. Wow, I said, maybe we should do this. At the time, my life was in complete transition. I'd just quit my job, started graduate school, and was scrounging for part-time work. In theory, having sex for money seemed doable. But Ray said he didn't want that to be a part of our relationship.
     We posted a generic ad on Craigslist anyway: Want to watch a hot young couple fuck in your living room? We detailed our body types, my curves, Ray's inches. While waiting for responses, I hesitantly asked Ray what we'd do in front of the stranger. We climbed into bed and he pinned me down, holding my wrists, whispering the play-by-play: We'd start by kissing on the stranger's couch. Lights on. Ray would kiss my neck, move his mouth down my clothed body, his tongue uncovering skin in between my shirt and skirt. The man would watch us, tell me to flip onto my stomach, raise my hips so Ray could pull up my skirt, slowly.
     I felt like a dark sort of celebrity, dating a sex worker. That Ray could ostensibly handle this lifestyle amazed me. Unlike my other lovers, he wasn't afraid of or dismayed by any sexual scenario I suggested. In fact, he'd already tried almost everything I wanted: light BDSM, anal play, toys.
     Ray would stay at my house for days, and when he left, I'd look for his m4m Craigslist postings. It thrilled me to read them. The illicitness of his work, the knotty thrill of not knowing who'd answer or where'd I'd pick him up afterward led me to imagine what it'd be like to enter into unknown, sexually charged situations to get paid, and how I would deal with that if I had to. Then I'd troll the sex-for-money ads, my fantasies racing as I read, again, what Ray and I could potentially do.
    One night before I was going to meet him, I found a derivation of our ad, a few days old. But the woman described in the ad wasn't me. Though we'd been together over a month and he'd been almost living at my house, we hadn't determined whether we were monogamous, but I'd asked him to tell me if he had sex with anyone else. I naively assumed he wouldn't look for other women to fuck.
     We had a drink; he paid. I casually asked if anyone answered our ad; he said no. I asked what he did that day, he said the usual, I said I found a mw4m ad that looked liked his, and he confessed that afternoon he'd had sex with a girl he barely knew in front of a man he didn't for

$200. He had $100 burning a hole in his pocket, and he wanted to go out, and he was so sorry he lied to me, but it was work, and he wouldn't do it again. I said I knew it was work, but just to be honest with me. He said okay. My queasiness was temporarily soothed by his sweet, affectionate apology.
     Ray couldn't save a dime, and his work was sporadic, so I paid for more than my share of meals with my dwindling savings and nearly nonexistent income from odd jobs and catering. In return, he'd continually feed my imagination. When we drove by houses, office buildings and stores where he'd gone in the middle of the day for a quick $60 blowjob, he'd describe what went through his mind when it was happening. He'd detail it all: how he'd tell the receptionist he had a meeting with the architect, Mr. So-and-So, walk into the guy's office, close the door, ask for a drink, drop his pants. We'd have multi-orgasmic sex, and I'd buy us take-out.
    I've never had a lover who was as reckless as Ray was — monetarily, emotionally, sexually — and the way he dealt with his work, or at least he described how he dealt with it, was with a nonchalant freedom that was enticing. But the novelty began to wear thin after a couple of months. One night, at his insistence, we were having a too-expensive meal. After we ordered, he realized that he couldn't completely cover it. He was in an explosively bad mood, and when I asked him what was wrong, he blurted that our sexual chemistry was off. Nearby diners turned their heads; my face got red. Ray said he wasn't completely satisfied with our sex life. Specifically, he wasn't satisfied with our oral sex life. More specifically, I didn't give him enough head.
    I'd never really gotten into going down on Ray. When I did, it wasn't for very long and it was never to completion. Lately, I'd been skipping oral completely but didn't want to tell him why. I said, quietly, that even though I knew there was a slim chance of catching something, it still freaked me out.
    He got offended, pounded the table. You get head all the time, I said. Sometimes three times a day. Why do you need more? That, apparently, wasn't the point. The point was that my avoidance made him feel unwanted, and more than that, unattractive and un-hetero. My desire to pleasure him had begun to wane, and I wasn't interested in trying to revive it.

    During that time, I had a lot of things to do: my graduate classes kept me busy, as did my hunt for steady part-time work, and I was getting evicted. At first, I didn't think too much about Ray's moodiness. When Ray would stay up all night while I slept, eating everything in my kitchen, then sleep until five in the afternoon, I didn't realize it was because he was often on drugs. He said he was nocturnal. Our fights became more frequent, our conversations strained. We both knew our relationship wasn't going to last, but we hung on to each other for what the other was providing. He fed my fantasies; I fed him food. 
    The breaking point came near the four-month mark, when I introduced him to some friends over an embarrassing dinner. He met us at the restaurant, and immediately told me he hadn't eaten all day. His eyes were frantic. Maybe he was hungry, maybe he was high. Either way, he had no money. Throughout dinner he ignored my friends, gripped my hand across the table, picked a fight with someone during dessert. Our group loitered on the sidewalk afterward; I wanted to go hang out with them, not him. Instead, I told my friends we were going to leave, and they stumbled over each other as they ran away, waving goodbye.
    We broke up later that week.
    Sometimes I still see Ray around. We wave hello, chat. When we were breaking up, one of his clients started a website for him. Occasionally I check it to see if he's still hustling, and he is. But I'm not. Fantasies aren't something I need to pay for anymore.  n°