CRUISING DIARIES
1991-2001

That summer vacation I was fifteen, and had just finished my freshman year of high school. On a perfect sunny day at a water park in New Hampshire with my parents and two little sisters, I noticed a man who couldn't take his eyes off me. He looked about as old as my dad; he was hairy, well built, and had a receding hairline, which I found incredibly sexy. The way his eyes burned through me awakened the strangest sensation, combining delight, arousal, and panic. This was the first time anyone had ever openly expressed desire for me. At the time, my knowledge of homosexuality was limited to one episode of Oprah in which she interviewed a man who had done the unthinkable: he’d left his “poor wife” for another man! Socialized as a homophobe, instead of feeling gratitude that he was brave enough to share his story on national television, I judged him harshly. He wasn’t half as handsome as my macho water-park stranger. My lack of gay knowledge as a teen in the pre-internet era led me to conclude that gay men were like unicorns: mythical, incredibly rare creatures. I felt lucky to have a real one in front of me, but why did I have to be here with my family? I pouted. Still, I found his gaze empowering; it gave me a weird sense of control. As the first child of loving parents, my healthy self-esteem prevented the Catholic priests in our parish from convincing me that my same-sex urges made me an outcast or a freak; instead, I fancied myself an insider belonging to a taboo secret society. I wasn’t going to let anything disrupt my first taste of being objectified. Aiming to heighten the man’s desire, I grabbed a lollipop from my mom’s bag and made a spectacle of myself. Once I could see that he was hooked, I headed toward the locker room, making sure he followed. I got into the group shower with my swim trunks on, and let the water pour over me as I sucked seductively. Bingo! He claimed the showerhead next to me, his bulge swelling through his wet boardshorts. I couldn't believe it: less than an arm’s length from my face was a hard cock, the first I had ever seen other than my own. Mesmerized, I completely forgot that I was with my family. Just as he started to pull down his trunks . . . “Michael! Michael! Michael! Where the hell did you go?” my concerned father yelled, tragically destroying what seemed to have been a once-in-a-lifetime opportunity.

By sixteen, my straight friends had started bragging about their first attempts at sex, and I knew I was missing the party. I regularly jerked off to the water-park guy. How could I find another man like him? A revelation appeared in the Phoenix, an alternative newspaper I’d picked up at a trendy café: an ad for something that I didn't know existed—a gay chat line. CONNECT WITH LIVE GAY MEN NOW! The newspaper sat in my bedroom closet for a month as I plotted. I couldn't use my home phone; my parents would surely see the number on their bill. I chose a high-stakes alternative: my football coach never locked his office. After school one day, I waited until the locker room was dead silent. Then I sat in the dark office and dialed the chat line.

“Describe yourself,” demanded the stranger.

“I’m a sixteen-year-old jock with black hair.” The line went dead. I hadn’t realized I was below the age of consent. Until that moment, I thought those laws applied only to girls.

Next try: “Are you gay?”

"I am gay,” I admitted to the stranger, saying the words out loud for the first time in my life.

“How old are you?”

“Eighteen,” I lied.

“Perfect! Have you ever seen gay porn?”

“Never!” I exclaimed.

“I have an extensive collection . . .”

He gave me his number—a big victory, because I could now call from any pay phone. I called Scott every day for two weeks before he proposed that he pick me up after practice. AIDS, kidnapping, or murder never crossed my mind. His extensive gay porn collection outweighed all risks. When the beat-up ’80s Mustang pulled into the empty parking lot, I swallowed nervously and waved.

“Mikey?” I nodded my head but hesitated. “What are you waiting for? Get in the car, kid,” said a white man with a salt-and-pepper beard and a large round belly that touched the steering wheel. He drove us to the edge of the school’s enormous empty lot and parked in the back row while I examined him. Sensing my disappointment, he handed me two magazines, Play Guy and Drummer. He gambled that providing porn to an isolated, horny gay teen would make up for my lack of attraction to him. He was right. My energy was supercharged: the fear of being caught, mixed with raging teenage hormones and the thrill of these over stimulating images, electrified me. I responded physically; my underwear became wet with pre-cum. I was hyperaware that there was a price of admission: Would this gross man’s dick be the first ever to go in my mouth? Scott said, “If you like these, you’ll love my pictures.” He handed me a binder that held a collection of Polaroids with images of naked boys around my age and younger. Some were full nudes; some were close-ups of asses or hard-ons. It became clear I wasn’t anything special for him. “I host exchange students,” he bragged, “Every summer, a boy comes to live with me.” This creepy turn didn't discourage me, all I could think about was access; this man was my golden ticket to Euro gay youth. “You obviously like what you see,” he said, as he grabbed the wet spot on my sweatpants. “Pull those down for me, you deserve to be catalogued.” Addressing my visible panic, he assured me: “Not your face, kid, just your cock. Don't worry, I’m the only one in the world that will ever know it's you.”

“Sir, I’m sorry but I gotta run, it's already 6:30, and I told my dad 7:00 . . .”

“Come on, you’re every bit as hot as those guys you like in Play Guy. Let’s capture it. At the count of three pull those shorts down for me. Only then I’ll let you go . . .” The car door locked as he spoke, trapping me. Terrified, I did as I was told. “Good boy, keep them down, that’s it. Two more.”

I felt high from being objectified on camera, but disgusted that there was evidence of this encounter. As he waved the Polaroid in the air, he unlocked the door. “Mister, I’m sorry, but I really have to go now,” I said with the polite tone I used for all authority figures.

“Glad to meet you, kiddo, next time we’ll do this at my place, and I’ll show you some actual hardcore films.” I got out slowly, but once the door closed, I ran as fast as I could back toward my high school. I never called Scott again. I never used the chat line again. I never told a soul.

At eighteen, I was a Rhode Island School of Design sophomore, dating a charismatic, voluptuous girl from Wisconsin. Chani was infamous because of her mother’s former career as a bunny at Hugh Hefner’s Playboy mansion. Although it wasn’t my natural inclination, I figured I shouldn't rule out heterosexuality without trying it. Chani had the right combination of experience and sexual aggression to get me to experiment with straight sex. We fucked often. After the newness wore off, I became jealous of her: I needed to get fucked too. AOL was my solution. My generation understood that the future would be online. For me, the technology would deliver one enormous benefit: gay chat rooms! On the computer, I’d be able to see a picture of who I was talking to before deciding to meet them. One obstacle bigger than having a girlfriend was not having my own computer. It took all my courage to use the campus lab to hunt for gay sex. The risk of being exposed forced me to handle my extracurricular sex life with attention to detail of a secret agent. I chose a Friday night, when the lab was dead. Armed with a Photoshop assignment as my cover, I waited until the final fifteen minutes before closing, when only the monitor and I remained. I logged in and cringed at the awful dial-up modem sound. The garbled abstract noises seemed to shout GAY! GAY! GAY! I sunk in my seat; distrustful and terrified, online could be a bigger risk than the real world. I didn’t understand its rules and boundaries; I could have easily left a public record of my secret life. Even so, the promise of meeting men that I might actually be hot for was stronger than my fears. My virgin act of sexual branding: choosing Collegeboy98 (1998 being the year I would graduate) as my online handle. That day Providence had only one active gay chat room that day: M4MPVD. Far from being the virtual gay-sex paradise I'd dreamed about, there were only three users in attendance:

RI_Ital: Anyone lookin on the East Side?

ProfessorLONEheart: Woonsocket here, ready for action.

UrbanPlan30: Mirabar tonight?

Adrenaline coursed through me. Five minutes until closing. I had to act fast.

CollegeBoy98: How does this work?

UrbanPlan28: Collegeboy, you new here? I’m in Providence for grad school.

CollegeBoy98: YES! NEW to chat rooms, NEW to gay people! How old are you?

Urbanplan30: 30

ProfessorLONEheart: What’s your age?

CollegeBoy98: 18

RI_Ital: the right age to start giving Daddy head.

CollegeBoy98: Urban Plan can I see your picture.

UrbanPlan30: Sure lets take this to email.

Immediately my inbox had a new message from Deni.Russo@AOL.com. Attached was an image of a shirtless man with a muscular tanned torso wearing fitted blue jeans. His face was crossed out with a marker. Under the picture he wrote: “I’m new to this too. Let’s see what you look like.”

I refused to send him a picture. “I swear I’m very fit. I was a champion high-school wrestler. I also played football.”

Cars, restrooms, and steam rooms comprised my entire teenage gay-sex experience. Every homosexual interaction took place with anonymous men in public spaces, taking sex out of the realm of companionship and into the realm of thrill-seeking. Deni offered me a new experience: privacy. He had his own apartment and had no qualms about inviting me over. When he answered the door, neither of us hid our joy. “Wow! All right,” he said, with a thick Italian accent. At twelve years my senior, he was younger and more handsome than the men I’d met before. He had large, almond-shaped blue eyes; thick, slicked-back black hair; and manicured eyebrows. His grooming signaled that he was European—the first gay foreigner I’d ever met. My harsh New England Italian-American accent seemed just as exotic to him as his Sicilian accent was to me. The idea of getting fucked by a guy I could relate to seemed so out of reach that I’d given up on the possibility in high school. But this was someone that I could hang out with in public without raising eyebrows. Deni fixated on a mark on my lip, the start of a cold sore I hadn’t noticed. “Do you know your status?” he asked, breaking my fantasy. I’d never gotten a test. Tests were for fags. I wasn’t a fag. I just sometimes had sex with men, I explained to myself. The mark on my mouth spooked Deni. He refused to kiss. We had weird, quick, self-conscious sex, that of men who were ashamed. We sat on the bed naked, looking up at the ceiling. Deni said, “My question—it threw you, didn’t it? It’s just . . . you're really young, and you must understand the consequences of your actions. My twin brother was also gay. Last year he died from AIDS.”

In 1999, Gaydar.com went live, becoming the first website entirely dedicated to connecting gay men. In 2001, Boston-based Online Buddies, Inc. followed their lead. This company, which was behind the gay chat line I had used as a teen, evolved into ManHunt.com, a site that would come to dominate gay online hookup culture throughout the aughts. Though both sites had revolutionized gay socializing, I’d hardly noticed them. In quick succession I’d graduated, come out to my parents, and broke up with my controlling, conservative, college boyfriend. After what felt like a lifetime of restraint, I finally escaped the small-town gay sex deserts of my youth and traded Providence for the homosexual mecca of New York City. My sex drive was my north star, guiding almost every decision.

By the early 2000s, the stigma lingering from AIDS still cast the ugly shadow of judgment on gay promiscuity. It was acceptable to be an out gay man as long as you presented non-sexually, especially in professional contexts—even if your company was run by queens, as mine was. My in-office solution for channeling my overwhelming libidinous energy was to cruise on the internet. In a way, online connections were almost irrelevant for me, because the entirety of Manhattan felt like one enormous gay bar; also, I risked being fired if I were caught scanning ManHunt.com or Gaydar.com in the office. Besides, the corporate feel of those sites wasn’t my thing: based on their advertising images, their target customers were hairless gym bunnies who sipped Cosmopolitans and delighted in Carrie Bradshaw. I considered “those gays” to be capitalists, conformists—part of an ideological tribe at odds with the punk-bohemian gay life I longed to be a part of. Instead, I spent my downtime at the office furtively perusing Craigslist personals: men seeking men. Craigslist’s text-only interface used zero marketing imagery, so it was easy to look at while in the office, and the lack of visual role models excluded no users. If Manhunt and Gaydar were cocktail lounges, where overly groomed men offered their best facades, then Craigslist M4M personals were an honest, sleazy back room. Craigslist didn’t offer a preformatted profile with some preference boxes to check off. For me, as someone at odds with the gay mainstream, Craigslist’s approach was welcoming. It also appealed to people of color, fetishists, freaks, and men who desired sex with men but for whom a profile on a gay site was a step too far. The idiosyncrasies of Craigslist M4M personals pulled me through each day.

Seeking Gloating, Shallow Republican Fucktard

You: gloating, sanctimonious hypocrite who seeks having their ass drilled like it was the last parcel of the Arctic National Wildlife Reserve

Me: angry, cocky disillusioned Democrat with a general contempt for tight-assed, closeted Republican pretty boys. I will re-educate you with my own version of ‘supply side’ economics.

Since my initial foray into gay online culture via AOL, the scene had rapidly transformed from a self-conscious place full of fearful users to a brave new world of bold men eager to articulate their specific kinks. Still, I wasn’t interested in fully joining the party with my own ad—instead, I became a dedicated Craigslist voyeur, reading it strictly for entertainment purposes. That is, until a post by a user named ZebraShades caught my attention:

13 Inches of BBC, Public Sex Only

45. Conservative, professional and discreet by day; freak each and every night. White college boys only. Absolutely no relationships. Come play with Daddy’s kids.

An attached image showed the biggest cock I’d ever seen, porn included. To illustrate its girth, ZebraShades had fastened a silver Rolex around his member, which was pulled out of the fly of a pair of khakis. The dick alone was enough to pique my interest, but the clashing signifiers stuck in my head. I observed passively as ZebraShadesposts popped up intermittently. I never dared respond, but like an earworm, the name Zebrashades echoed in my mind. Finally, months later, hungover and horny at the tail end of ten hours of filing tedious paperwork, I relented. For the first time in my life, I emailed a photo of myself (including my face) to a stranger in the hopes of soliciting sex. My boyish, fully clothed headshot did the trick. The next morning I received an email:

I’m into it. Be at my office tonight at 7 pm sharp. Ring the bell and wait for me. Don't speak to anyone. If you're a minute late it’s off. 1130 Amsterdam Ave. —ZebraShades

That night, I found myself on a long subway ride from Chelsea to Harlem. The address he gave me was on a college campus. A sign outside read: Admissions Office, Columbia University. I rang the bell.

The man who greeted me towered over me. He was not the slick macho I’d envisioned. He wore tortoiseshell glasses, a crisp white dress shirt, a navy-blue suit, and an Hermes tie. I clocked his shiny silver Rolex—clearly, his online photo was legit. ZebraShades had the look of a school principal, a nerd with an air of authority. “You must be here to take my kids,” he said, with a hint of condescension. His accent was confusing, with both English and Caribbean elements; I'd later learn he was Guyanese. He led me down a dark hallway to a private office. Once inside, he locked the door and drew the blinds. As he saw me focus on the nameplate on his desk, he flipped it over, but not before I could read it: ______________, Director of Admissions. “Take your clothes off!” he barked. I was stunned. I felt slightly threatened, which turned me on. Without even taking his cock out, ZebraShades’s no-nonsense, aggressive demeanor had surpassed my expectations. His eyes lit up at the sight of my naked twenty-three-year-old body. “I interview these rich young brats day in, day out, with their bouncy, lily-white booties . . . what torture it is that I can’t touch any of them. You're here to fix all that. What are you waiting for, kid?” he barked. “Get your ass over my desk.” Except for pulling his spectacular dick out of his fly, he remained fully clothed while fucking me. Sexually, he and I brought out the best in each other, even so, Zebrashades maintained the boundary in his ad: absolutely no relationships. Whenever the sexual frustration of campus life became unbearable to him, he gave me a call. He fucked me in various secluded spaces on campus: his office, public restrooms, the janitor’s supply closet, and, in the summer, empty dorm rooms. Once, for a special occasion, he surprised me with a treat: he invited a cop friend of his to share me. Our Craigslist M4M arrangement fulfilled deep, specific needs. We met up periodically over the next four years, until ZebraShades accepted a better-paying job in Australia.

Looking back, I took for granted my great fortune that my sexual development coincided with a technological revolution. Up until the ’90s, small-town homosexuals like me were limited to finding relief through anonymous encounters at word-of-mouth cruising spots. Since cruising usually involved public sex, most of my gay peers and I started our erotic lives breaking the law. Though experiencing multiple taboos simultaneously was sometimes exhilarating, those interactions could also be creepy. Hooking up with mostly closeted men kept us all in fear of each other; each encounter ran the risk of both exposure to HIV and being outed. Because of this, contact usually ended as soon as the sex act was over. Devoid of real comradeship, and without relatable gay figures in the media, forming a healthy identity around same-sex desire was nearly impossible.

But by the mid-’90s, for the first time in history, that experience was no longer the only option: men seeking same-sex encounters would not have to be limited by geography and chance. We now had the digital tools to find sexual partners that were absent from our lived reality. While most cruising up until that point was about protecting your anonymity, leaving no trace of your identity, in the new online world leaving a record was required. Participants became accustomed to (and eventually comfortable with) articulating their secret yearnings. One profile at a time, each individual’s contribution empowered the collective, until a much more liberated culture around gay sexuality emerged. We gave each other confidence: digital space allowed a generation of men to grow together, enabling us to each fearlessly seek out our own ZebraShades. The birth and evolution of digital cruising platforms in the ’90s brought the once-taboo underground experience of seeking out gay sex into the mainstream, enabling a marginalized populace to discover one another, replacing scarcity with abundance, isolation with the promise of connection.