A Series Of (Fortunately) Unfortunate Events: A Craigslist Chronicle


IN HIS BOOK (AND my personal bible), The Velvet Rage, Dr. Alan Downs describes the second stage of the gay man’s development as a compensation for the overwhelming shame felt while in the closet. He paints the newly out gay man’s desire for casual hook-ups and brief sexual encounters as not necessarily a celebration of his sexuality, but rather as a coping mechanism for a set of “distressing emotions.” At the top of that list of emotions, he states, is loneliness. He goes on to explain that, much like the monster under the bed that’s not really there, our fear of loneliness is generally unfounded and not based in reality. Over five years after coming out, I can say that personally this has proven to be the case. It is through this psychoanalytic lens that I now view (and have come to understand) the following series of events that took place in the year following my coming out.

Here I was: a gay man who had recently openly and firmly declared to the world his fundamental truth for the first time. Now what? I had flirted with men in the past, lost at least part of my virginity (while still primarily in the closet), but had yet to really explore myself and my sexuality in a profound and honest way. I wondered how to go about beginning this journey.

Naturally, I turned to Craigslist.

In the days before location-based hookup/dating apps for our smartphones, there existed (and still exist) an online realm of darkness, desire and deviancy: the Craigslist “Casual Encounters” section. It was with little trepidation that, not long after my official coming out, I plunged into the depths of this wonderfully sordid corner of the internet. By “plunged,” of course, I mean that I was perfectly fine engaging with the postings from a voyeuristic standpoint — happy to read through the various mating calls, especially eager to click on the ones that had the enticing “pic” label beside their descriptors, pictures that were usually dirty. However, it took a little more of self- cajoling to bring myself to actually post an ad of my own.

After a glass of chilled white wine, I tentatively conducted a mock-creation of a post, discovering that the messages I hoped to receive in response would be directed to a real email address — meaning that, were I to reply to a potential suitor, my identity would be revealed. Being the educated and stealth young man that I was, I saw the need to create a new Gmail account for my undercover sexual pursuits. And, boy, did I ever seize the opportunity to have a whole lotta fun with these e-mail addresses. Throughout my year-long tenure on Craigslist, they covered a whole spectrum, ranging from flirty (kisstheboy@gmail.com) to floozy (upforanythingintoronto@gmail.com).

Having now created and solidified my first online alias, it came the time to take the real plunge and to truly put myself out there.

First Encounter

I used to share an apartment with my younger (but not that much younger) sister.

Although she was (and continues to be) an adult, I barely felt comfortable bringing guys I had met at the bar home, let alone a complete stranger from the internet. What this meant, then, was that I was to wait for a night when my sister returned to our family home for the weekend before I could embark on my first adventure.

After making sure that I was alone for the evening, I went onto Craigslist.com. Now, there are two ways that one can go about to secure a hookup: you can simply go through the ads that already up and respond to them, or you can create one yourself. After perusing through others’ posts (and responding to a few with my already-created online alias for the night), I decided to put up my own. I made sure that the ad was open and inviting, yet casually detached. It included my age, a qualified statement of my attractiveness (“cute, young, relatively fit undergrad”) and a declaration that I was “up for anything (as long as it was safe).”

Quite quickly, I received a bunch of responses from various guys, to which I replied to a few, and went back and forth with for a couple of minutes. We went back-and- forth for a couple of minutes, and the majority of the messages contained a dick, an ass or both. I then got a message that had a chest, a quite attractive chest, and something about it hooked me. I started corresponding with this guy and seeing what his plans were for the night. After corresponding for about twenty minutes, I invited him over.

Now this is where all my “preparation” came into play. I called my best girlfriend, let her know what I was doing and asked her to call me about half an hour from when he was to arrive to make sure I was OK. We established a code language to communicate whether I was safe or in trouble or simply wanted the guy out my apartment. Thankfully I never had to use the actual emergency phrases, but I definitely used my conversations with her to wrap things up with my partner for the night. “Having to go pick up my sister from a party” became the go-to scene for her and me to play out over the phone.

The other precaution I decided to take was to hide various objects that could serve as weapons around my apartment. Besides hiding multiple knives in drawers in the kitchen and living room, my most specifically laid-out plan involved a frying pan in the cupboard under the sink in my ensuite bathroom. The plan was that, if at any point we had entered into the bedroom and I didn’t want to continue with the encounter or if I felt that I was somehow in danger, I would excuse myself to the bathroom and quietly retrieve the large metal frying pan from under the sink. I guess I would then charge at him with it and hit him over the head like we were in some sort of Saturday morning cartoon.

What would I do with him after he had passed out? Not sure. Run out of the apartment and call the police? I don’t know. Thankfully it never came to that point.

Once these plans had been set into motion, I changed into my laid-back-yet-put- together outfit just as my phone rang, letting me know that the guy was downstairs. My heart was racing as I got into the elevator and headed down to find my partner for the night. I wasn’t sure if I was going to recognize him and if he was going to recognize me. As is always the case with these situations, you hope that the face pic bares some sort of general resemblance to the man with whom you are about to come face to face.

There is a lot going on. There’s a lot of vulnerability. You want them to resemble their picture; you hope that you resemble yours. You hope that you pass the immediate test of attractiveness for them. I came down the elevator, exited the building and, thankfully, quickly found him outside the entrance. He did resemble his picture, perhaps a little bit older, but it wasn’t a problem. I saw him take me in for a second; thankfully, he said out loud that I passed the test. He had brought white wine, which was nice, so we began to drink that once we had made our back to my apartment. I was surprisingly calm given the amount of new variables and elements that I was directly dealing with, and after a glass of white, we got down to business.

I wasn’t expecting that this would end up being my first time bottoming. Having bottomed since then, this experience was — in more ways than one — the tip of the bottoming iceberg. I do not recommend being with a large penis for your first time. My ass hurt for days after. That being said, it was a relatively quick and easy way to jump over that hurdle in my “gay sex checklist.” The rest of the encounter was pretty unremarkable, save for the big finish: it was the first time any guy had come on my face. A couple hours after he had left the apartment, I looked in the mirror and noticed that his ejaculate had dried up and created a lovely, flaky mask. I guess I didn’t realize how thorough one has to be when cleaning up after such an act.

Second Encounter

It was my first fall back to school post- coming out, and while studying at the library, I decided I needed a break — well, more of a release, really. I put up an ad on Craigslist specifically listing my location as on the university campus. I got a reply from someone who was actually pretty close to where I was working. He suggested meeting in the basement of the building beside the library. I packed up my things and left to go to make the short walk to the other building. While I was heading over, I realized that the bathroom I was to meet him in had multiple stalls and, thus, other non-participants could be present. Thankfully, when I walked in, we both spotted each other immediately, recognizing our faces from the pictures we had exchanged. I suggested we head to another washroom that could afford us a bit more privacy.

I had taken a liking to studying and working with my best friend in the computer lab on the 3rd floor of the library, and I knew that there was a single washroom (that could be locked) right across from the lab. I also knew that, having just been in the lab, that there were very few people in the immediate area. With this in mind and the cute boy in tow, I led him to this washroom. I passed friends and acquaintances of mine while walking him through the library, trying very hard to act casual given the exciting and kind of dangerous nature of the circumstances.

I led him up to the 3rd floor. He ducked into the washroom first, and I followed suit. We kept it to making out and blowjobs, but at the end, he stated that he’d “really like to get me into bed.” After sliding out of the washroom separately, he gave me his number and we said our goodbyes.

One night later that week, he stopped over at my apartment on his way to a party. Things got heavy pretty quickly, and I experienced another first: having unprotected sex. It was, as it is often described, a heat of the moment decision. While still inside me, he asked, “Are we supposed to be doing this?” I replied that I didn’t think we were, but he assured me that he’d pull out before he came — a promise he kept. We finished up.

He went off to his party, while I proceeded to stay up most of the night Googling HIV transmission rates, HIV symptoms, and all other statistics, information and analyses relating to HIV and gay men. I sent myself off into a frenzy of paranoia, anxiety and self-flagellation. It was through this experience that I was directly confronted with the shame that comes along with the expression of gay sexuality even after having come out as a gay man. It is a theme that has run throughout my sexual life. Even though I have been able to be honest with myself and others as to who I am, I still struggle with being a proud sexual being.

The morning after, I headed straight over to the sexual health clinic on campus to get myself tested and speak to a doctor. My mom called while I was in the waiting room and I relayed to her, in vague, but not really that vague, of terms of what had transpired. I talked to the doctor who, after hearing my story, assured me that while I had engaged in a high-risk activity, the actual risk that I contracted HIV after this one specific instance was actually quite low. My anxiety was alleviated for a while but never completely until I received the negative test results and hasn’t really dissipated since then, no matter how safe and/or abstinent I may be. It was a real lesson in forgiving me for my perceived mistakes, while also giving me a strong indication of what life as a sexually active gay man might look like from that point forward.

Third Encounter

In the winter later that year, while in rehearsal for a musical at a theatre on campus, I embarked on my third and final Craigslist encounter. After a long and intense rehearsal process, combined with December exams and crunch time in the academic year, I needed a moment of reprieve and release. Before leaving my apartment for a night rehearsal at one of the theatres on campus, I put up an ad online looking for some company later that evening. Prior to leaving the house, I had received an eager message from an older gentleman who I assumed was in the city on business — staying at a not awful, but not terribly nice, hotel close to campus. We exchanged pictures, but he didn’t send me any ones of his face; however, he described himself in great detail, which engendered some trust within me. I had let him know that I was heading to rehearsal and that I would be in touch after, with the assumption that I would be coming over to his room after finishing up.

As rehearsal was nearing its end, I arrived at a crossroads: either to go home, or take a risk and go see this faceless businessman at his hotel. I contacted him and let him know that I was on my way over. I walked over, entered the hotel lobby, got on the elevator and made my way down the long corridor towards the room number he had given me. I knocked on the door and he opened it. To say that he was much older than he represented himself to be (or perhaps that I had, in my mind, expected) is an understatement. This man was, if not in his 60s, at least in his late 50s. The first thing he asked me, after opening the door, was: “Am I okay?” Being the “nice” person that I was, I said “yes” and entered his room — although all I wanted to do was say that I was sorry and leave. However, as a 20-year-old newly out gay man, I didn’t have the kind of sense of self that (at 25) I now do. So I went into the room.

At that point, I committed myself to making this a performance: both for myself and for him. I made the decision to enjoy whatever was to transpire. I found myself creating a backstory for the man facing me and asking me what his life was like when not in this dark hotel room. Was he from this country? Was he married? To a woman? Did he have kids? Did they know this is what he did on weeknights while away on business?

Part of sticking to my commitment to making the best of the situation involved me taking control, which was uncharted territory (especially within the sexual domain). I positioned myself on top. I told him what to do, where to touch and how much pressure to use. This was only possible because I was wearing the mask of performance. By creating this persona (or perhaps unleashing one that was already present within), I was able to turn this potentially awkward (and perhaps destructive) incident into a moment of power for myself. After getting off, I gathered my clothes and other belongings that I had been strewn around the room and left.

The hotel was approximately a 5-minute walk from my apartment. I was about halfway home when I looked down at my wrist for the time and noticed that the (quite expensive) watch that I had received as a birthday gift was not in its usual place. I immediately panicked but thought that it might be somewhere in my room at home. It was not. Thinking that this man had stolen my watch, I ran back to the hotel, up to the room, and pounded on the door. He groggily let me in, already having gone to bed by this point.

My instinct told me to loudly state how inexpensive and meaningless this watch was — just in case he had, in fact, stolen it. He said that he didn’t know where it was and hadn’t seen it on me when I came in, so I began frantically looking all over the room, my eyes darting and my hands rummaging, finally finding the watch face down under the bed. My heavy and racing heart became weightless and happy. I thanked him for the nice night, apologized for waking him up and left the room.

As I walked back home, I replayed the night’s series of events (along with my previous encounters) in my head. They had taken on a surreal quality by that point. Although all had occurred relatively recently, I viewed them with both a sense detachment and nostalgia, knowing that they would make good stories but with no desire to relive them again.

The man I was five years ago was as barely a man and more a lost boy. However, sometimes I miss the reckless naiveté and sense of exploration and sexual freedom that he represented in such a pure way. Five years later, I now find myself on almost the opposite end of that spectrum: anxiety, caution and “safety” being the dominating and driving forces behind my sexual decisions. As with my mindset in other areas of my life, I am striving for a balance — balance between living for and in the moment and ensuring that I can, in fact, live past it, into the future.

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image – Craigslist.com