Planet Craigslist recounts my years of trolling men with a series of depraved sex ads. The entry outlining the project can be found here: Planet Craigslist: Bang My Mom

From the age of 15 to my late 20s I met countless people off the internet. Now at 32 I still do though not as often. As a six foot male I spend near zero time thinking of their intentions. If they are who they claim to be. If they’re out to fuck with or hurt me. I’ve never come to a date carrying pepper spray. Never told a friend I was meeting someone and here’s their info. Not even when it was in a park after midnight.

I once drove to a sketch hotel at three in the morning after just a few words with an internet stranger. I had an off feeling so stood back from the door in case it was an ambush. It wasn’t. All that waited inside was an awful hookup. That I can handle.

The sole time I met a man for sex I took precautions I rarely do with women. I parked far off, carried nothing with my name, and came barefoot in case I needed to flee. Not that there is no danger in meeting women but I give it little thought. Despite sketchy nights I’ve never been hurt. I’ve had the privilege of ignoring my instincts. I’ve felt uncomfortable. Wanted to leave from the second I laid eyes on someone. But I’ve never felt scared for my safety.

In Portland I met a friend I’d known for years through Facebook. We went to school in the same town and had a clutch of mutual friends. When she moved to Oregon we finally got together in person. The first time we met was at a bookstore in daylight. The second a comedy show at midnight. As I drove her home I took a wrong turn and wound up in an industrial yard. It was vast, empty, and supa creepy at two in the morning. In no time I got us turned around and took her home.

A long time later, after we’d hung many times, she told me of that night from her perspective. How she had the knife in her purse ready to go. How maybe I wasn’t really lost but rather was readying to rape her. Despite my carelessness with strangers I’ve never considered such things. The worst I’ve had is discomfort and disgust. Even that’s no biggie. It comes with the territory of rolling the dice on an internet stranger.

For years Craigslist acted as my site of choice for sex. I shifted through the country and into new cities. Craigslist gave me the skeleton key to someone new. For a long time it worked. I met cool folks and fucked a few of them. I never thought much about the risk other than swaddling my cock in a condom. I guess I trusted my gut. Still, I often ignored the warnings it sent me. I found myself in sketchy situations. The nineteen year old who after I banged her told me this was actually her neighbor’s house. The drugged-out Russian whose mom called at five in the morning to scream how her daughter’s a bitch. The old ass lesbian in Minneapolis.

She contacted me off Craigslist and sent a single photo. It masked her face but showed a bare body wrapped in mesh. She asked if I was on FetLife. Told me of her shallow vagina but stated we could try penetration. She rarely took cock but wanted one now. I felt iffy about her photo. It was black and white and told me little. But she was near seventy and I like old ladies. I gave power of attorney to the man in my pants and he said go for it.

We met late in a grocery lot near her place. I parked down the road and walked up to someone in a rubber raincoat. It had to be her as this was the only person there. I felt disgust the second I saw her. I got why she masked her face in the photo. It was rough. Overtly masculine and tore down from the decades. I’m no beauty but at least I don’t hide who I am. It felt like deception but really I just didn’t do my due diligence. That was my fault not hers.

My instinct was to flee at full speed. I knew she couldn’t catch me and I owed no allegiance. But that would be rude so I greeted her, the disgust inside now growing stronger. We hugged and it felt wrong. I felt no attraction. In fact I felt the opposite. She walked me back to her place. The doorway opened to a long, rectangular bedroom lit in blacklight. To the right sat a small bed. To the left crates of yipping dogs stacked on one another.

She lay on the bed and invited me to it. I delayed by asking about the dogs. She was a trainer but these were a mix of both her own and boarders. I went to her bed and lay on the open side. She wrapped herself around me. My body language screamed I didn’t want to be there. She either took no notice or didn’t care. I sat stiff and uncomfortable as she snuggled into me.

She smelled of fake citrus. Her voice was gravelly as if pitched through tarred lungs. She wore the mesh shirt from her photo. At least that matched with what she’d sent me. I so wanted to leave but couldn’t find the courage to align my mind and feet. My brain blasted an SOS but I didn’t know how to exit without hurting her feelings or arousing anger. She asked for my astrology sign and rambled on about what it all meant. I told her I didn’t believe in that stuff but she gave an analysis anyway.

I traced fingers on her tits as she held me tight. Maybe I could just bang her to get it over with. She wasn’t a bad person. Just so not for me. But I couldn’t. I’m no actor and also doubted I’d ever get hard with her. As she grabbed my cock I took her hand back to my chest and said sorry but I’m not feeling it. That I’d like to go. She apologized that I wasn’t into things. That of course I could leave. I tried rising but she guilted me into staying longer. She said she never gets cuddles and asked if I’d hold her for just a few more.

She brought my hand back to her tits so I resumed twisting her thick nipples. I stared off to the ceiling and caged dogs. Disconnected mind from body to burn through these last moments. Finally she let me go, once more saying sorry it wasn’t to be. I walked out of sight then sprinted to my car, wishing I’d followed this instinct an hour earlier. Later I wondered if any woman had ever felt the same with me. If someone simply stayed in my bed to avoid the awkward conversation. I didn’t think so but there was no way to know.

I’ve spent just as much time meeting people as I have trolling desperate dudes. Creating online personas to play act as someone I’m not. This started as a young teen when I made a man fall in love with a woman I created from whole cloth. We were to spend Thanksgiving together. After the day passed and she no showed I revealed he’d been had. It was an awful thing to do. He did nothing to deserve it.

Over the next fifteen years I trolled a million men but almost never one so undeserving. I focused in on pedophiles and philanderers. I don’t know if they deserved it either but at least I didn’t feel like shit about it. Still, I’ve hurt a lot of men’s feelings. Made them think someone likes them or at the very least they’re about to get laid. It’s inevitable that over my near two decades of doing this there’d be backlash. I don’t believe in karma but I’ve been its recipient. Sometimes the internet bites back.

In Portland I posted a million ads looking for sex and snuggles. They conjured spambots and creepy dudes but on occasion a woman arose. A lot of times it was just to say they liked my goofy post and hey good luck. Sometimes they were curious enough to get together. Sometimes we banged. It was always fun or at least no worse than indifferent. Then I started getting awful emails. For months I received missives from a man calling me ugly, unfunny, and a fag. He poured through hundreds of ads to find my posts. For whatever reason they enraged him.

I have no idea what made him target me. My ads were the dumbest things ever full of corny ass jokes and PG photos of myself. He often changed emails but the responses stayed the same. Fag. Stop posting. Kill yourself. At first I responded in good humor saying thanks for the kind words or wishing him well. But my lightness didn’t lessen his anger. Fag. Stop posting. Kill yourself. This wore me down and after a month or two I simply stopped replying. The messages still poured in but all I did was delete them.

I spent a late summer day hanging with my roomies and two women from Switzerland. They were traveling down the coast and were with us for a night. I hoped one would wanna bang but that wasn’t gonna happen so I renewed an old sex ad. I forgot about it until I got home at night and checked my email. In my inbox sat a response from a girl who wanted to meet.

I messaged back and got a photo. It had black bars on top and bottom as if it were a screenshot off a phone. I should’ve asked for more but I didn’t. She wanted me to come to her place and fuck her. Rarely did a girl straight up proposition me for sex. Usually we had some dialogue or them telling me I was funny or whatever. We exchanged a couple more emails and she said “I see you’ve been posting a lot, big boy.” That response, coupled with the other signs, raised a million red flags. Yet I didn’t heed them.

My time in Portland was coming to a close and I wanted to get in as many last bangs as I could. I’m as dumb as the dorks I troll. So I ignored gut instincts and went to meet her. All the years of fine and benign meetings left me unable to imagine that this would be anything but.

It was late, at least midnight, when I drove downtown. I had the address and parked a couple blocks away. This was my standard practice but was more about anonymity than anything. The girl now had my number and texted to get a window for my arrival. I felt iffy about all this. I wondered if she was fucking around or a troll sending me off on an errant mission.

When I walked up to her place and double checked the addy that iffiness turned to something worse. She lived in a flop hotel. From the sidewalk I could see the clerk behind a safety window. Bums and junkies ambled by. It didn’t look like the kind of place a pretty girl lived at. I crouched under the awning and texted I was here. Prior to arrival my phone buzzed with every incoming message. Now it sat still and silent.

I waited under the awning to see what came next. A young man walked out of the building and off to shadows as he ducked to a recess not far from me. After a few he went inside. A little later he returned. He enacted the same routine of slipping to shadows. He wasn’t out for a smoke or to meet someone. His presence felt off. Pure mystery.

He looked different than the others I’d seen here. He was in his early twenties, pretty good looking, and dressed in decent clothes. In the normal world nothing about him would’ve registered but here he stood out. Still, I didn’t pay much mind. I gripped my phone waiting for the feel of a familiar buzz. Is this girl gonna get me or not?

I texted asking if she changed her mind. To be stood up was pretty standard and so wouldn’t surprise me. I usually give someone a few before saying fuck it. She texted that she was getting ready and I could wait in the lobby. I wasn’t comfortable with that so kept in my crouch outside.

When the wait time was almost up my phone buzzed with a flurry of texts. They described exactly what I was wearing. Said I looked gross. That she changed her mind and wouldn’t fuck me. She claimed she spotted me out her window but that was physically impossible. I was hugged against the building and under the awning.

I hustled away. Holy fuck. This person was watching me and I didn’t know from where. I couldn’t see anyone but maybe they were across the street or in a parked car. I don’t know if I was scared but I needed to flee. I sprinted to my car, so thankful I’d parked far away and hadn’t given her my address.

I put two and two together then sent a text. “I bet you’re the dude who kept coming in and out.” The person on the other end didn’t deny this. Instead they sieged my phone with a volley of vile messages calling me a faggot, telling me to kill myself. Holy shit. This was the psycho that’d emailed me for months. Harassing me over Craigslist hadn’t been enough. He drew me offline and into the world. The ugly face of the internet opened its eyes and found me in its focus.

As over email I didn’t let on that his dumb shit bothered me. In the past it hadn’t. But unlike the emails this got my heart beating. The safety of the screen was no longer there. Even as I drove away I couldn’t calm down. In a rational sense I knew I was fine but still my adrenaline spiked. This was scary. A little too real. His words had been so hateful but I never thought he’d act on them.

I wondered why he chose me or took it this far. I knew there was no rationale behind it, that it’s useless to parse through the thought process of a psycho. I’d trolled so many dudes but never out of hate. I did it to entertain myself and others. To get some laughs. For him it seemed to rise from a deep and seething disgust for anyone he made his target.

I told him nice trolling. That I wasn’t mad. That I’d fucked with men in the past and game recognizes game. My congratulatory texts didn’t tamp him down. As with the emails indifference only made him angrier. He seemed determined to have the last word. To tell me what a worthless piece of shit I was. That I was a faggot. That I should kill myself. I asked how could I be a faggot if I was there to fuck a girl? At this point logic was long gone. He operated on hate.

I reminded him that I’d seen him too. That I knew he was the person who’d harassed me for months. He ignored these things but increased the unceasing stream of animus. I drove the the ninety odd blocks back to my place. All the while my phone buzzed like an angry bee. Fag. Kill yourself. Fag. Kill yourself. Fag. Kill yourself.

I stopped responding. There was no winning with this one. Once home I texted that I was done and blocking his number. For a final time he told me to kill myself. Then I never heard from him again.