Hookups are scary. There is always an element of fear when meeting a stranger. That’s your smart sense kicking in, your brain going into self-protective mode even as you adjust your cock ring.
A million things could happen. He may look nothing like his pictures. He may be deranged. He may suspect you’re the guy his ex cheated on him with, even if you’re not, and be planning his revenge. He may be newly single and burst into tears the minute you comment on his jockstrap (“Jonathan gave me this jockstrap, now he won’t even speak to me!”) Get ready for all unnerving scenarios as you start your precarious journey through the harrowing world of gay cruising and hookup sex.
Browse these 25 scary hookups that happen to all of us, and remember to always have an escape route. Enter if you dare!
My name is Alexander Cheves, and I am known by friends in the kink and leather community as Beastly. I am a sex-positive writer and blogger. The views in this slideshow do not reflect those of The Advocate and are based solely off of my own experiences. Like everything I write, the intent of this piece is to break down the stigmas surrounding the sex lives of gay men.
Those who are sensitive to frank discussions about sex are invited to click elsewhere, but consider this: If you are outraged by content that address sex openly and honestly, I invite you to examine this outrage and ask yourself whether it should instead be directed at those who oppress us by policing our sexuality.
For all others, enjoy the slideshow. And feel free to leave your own suggestions of sex and dating topics in the comments.
Hungry for more? Follow me on Twitter @BadAlexCheves and visit my blog, The Beastly Ex-Boyfriend.
Not everyone loves anonymous sex, but I do. Anonymous sex is one of the most thrilling parts of my gay life. It works because it's accident; it's chance. As with Christmas and birthday parties, planning anything takes away the fun of it and makes it routine: discussion, buildup, and the inevitable letdown of having things go as you foresaw.
Random, sudden sexual encounters with strangers — sex in the back of clubs, in back alleys, in airplane bathrooms, in parks in broad daylight — are like little gifts dropped from a naughty maker. The first time you find yourself in the right bathroom on the right floor of the right shopping mall at the right time with the right privacy and the right man, you will probably be very scared (of getting caught, of not being able to perform, and of the whole circumstance in general). I was, but then I swallowed my fear, and swallowed.
I knew about “the apps,” as they are now called, some time before I actually met a guy on one of them. I met him on the beach late at night. In hindsight, I made all the mistakes, because I didn’t know the rules. No one had told me to never meet in a remote location or to always tell a friend where you are and have an escape plan.
I was terrified. I was driving along a road in the middle of nowhere and walking down a pier in the dark to meet a stranger, who was visible by the light of a cell phone. As I got closer, I thought, This is how people die.
Don’t be like me. Meet in a public place where people are. Have an escape plan. You will still probably be scared, but at least you’ll have checked some boxes to make it safer.
The first time I went into a backroom, I had some warning: the sounds coming from behind the curtain gave me a pretty good idea of what I would find. I pulled the curtain back. My eyes adjusted to the dark, and I watched, disbelieving, as someone was bent over and fucked in a corner a few feet away.
Then I turned around and saw him: a 6-foot-8 tank of a man on the other side of the room, standing under a red light, looking at me. and rubbing his crotch. I approached him and he pulled his dick out. “Wanna suck?”
I did. I was trembling. The feeling I had then — the combination of fear, surprise, terror, and awe — was so powerful that I’m trembling even now as I write this. That was years ago, but I still remember hearing him say “It gets big” as I knelt in front of him.
Everyone has heard the hookup horror story where he wants to do things that aren’t on your agenda.
I once met a guy in Los Angeles who didn’t communicate that he was into gut-punching — a popular kink in its own right but not something I get into. I was on my back with his dick in my mouth and felt a blow to my stomach. I pushed him off me, heaving. “What the fuck was that?”
“You’re not into gut-punching?”
“I like that. I thought you were kinky. I like beating guys up.”
“I’m not really into that.”
“Come on, please? I’ll go at your pace, but I really want you to take it. I bet I can shove my whole hand inside you.”
I grabbed my stuff and left. I don’t even think I put on my shoes. Not everyone who’s into gut-punching is a dangerous hookup, but this guy was. If you’re into kink, there are more hookup rules: Never be incapacitated (tied up) by someone you don’t know, and never play with someone you haven’t discussed and negotiated your/his kinks with and talked about your limits and safeword(s) beforehand.
Someone who assumes what your kinks are or does kinky things with you that weren’t communicated beforehand is not safe. Period.
Even after you’ve communicated your kinks and interests, negotiated limits and safewords, and had a good prior discussion, you will still be terrified when you meet up for your first kinky play session with a dom (dominant play partner). A million thoughts will run through your head as he’s fastening your wrist restraints — What am I doing? This is insane. How do I get out?
My sincere hope is that the fear abates and you have a powerful, beautiful session. I was terrified my first time — and came out of it on the other side as a new man. My wish for every beginner kinkster (kinky homo) is that they have a rewarding first time and start slow. Play with someone who knows you’re a beginner and respects you.
Drugs are the classic ingredient of hookups gone wrong. The most frightening hookups are when he doesn’t use them in front of you — he dips off to the bathroom for a break and comes back ready to play — hard.
You may be having fun, but his behavior is off — he’s sweating, erratic, paranoid, or simply not where you are. Friend, he’s using drugs and not sharing, meaning he wants to be high and sees you as entertainment during the rush. Using drugs around someone without their prior consent is disrespectful and inconsiderate.
For me, this typically comes hand in hand with guys who are using drugs (including and especially alcohol), but not always. Some guys are just temperamental and aggressive people. They may be uncomfortable with hooking up, and their discomfort may translate to annoyance, irritableness, and paranoia. You don’t have to put up with someone’s bad mood. Bolt.
He says he’s in the closet, but he’s really not gay at all.
Gay baiting happens. This is like entrapment, except that it’s not done by police officers, but by private citizens who, for whatever reason, want to meet a gay man in the flesh. There might be harmless reasons for this — curiosity, questions — but most that come to mind are sinister: to proselytize, abuse, bully, or something of the sort. Be careful.
Tip to avoiding this: Meet in a public place, in the daylight, where people are around.
The first time I left a bar with a guy after I became HIV-positive, I was terrified. I kept delaying climbing on his bed until finally I had to sit down on a chair and tell him the news.
The guy was gold. He pulled me to the bed and kissed me, and I started crying. While mine was a good story, many of my HIV-positive family members have horror stories of people who freak out and scream and kick them out. Even in the age of PrEP, people are cruel and uneducated and prejudiced. Have an escape plan. Be ready to leave. If it all goes wrong, have someone you can call, even at a late hour, and talk to them — you’ll need them.
Forget haunted houses. Hooking up with a gay couple is a terrifying minefield of strong emotions you have to watch out for.
When threesomes are good, they’re great! When they’re bad, they’re terrible. Someone may get jealous or feel left out. One partner may feel insecure, guilty, or threatened by you: the blithe, horny third. If you find yourself in the crossfire of a gay couple’s screaming match — as I have, many times — quietly grab your stuff and run for your life.
There’s less to fear here than you think. Sex parties are just a bunch of guys who decide to get together and play — nothing scary about it.
There are sober sex parties and kinky sex parties and fisting parties and bare-only sex parties and condom-only sex parties and DILF parties and pup parties and more types of gay sex parties than you can possibly imagine. You can find one that fits your interests.
If you get there and freak out, politely and quietly leave. The general rules of sex parties are that you should respect the “theme” and you should participate, because no one likes be watched like a circus animal. If you can’t do either of these, quietly excuse yourself. You should always thank the host, and since sex parties can usually cost some money (lube, cleanup, etc.) offer to help clean up or contribute some cash before you leave.
It’s going to happen, my friend. At some point in your life you will attempt sex when your ass isn’t completely clean, and you will make a mess. Let’s not mince words: You will get shit everywhere. If this isn’t something you’re into, you’ll probably be extremely embarrassed.
Get him in the shower, clean yourself off, clean up the bed/sofa/sling/dining room table where you’ve been playing, and call it a bad night.
The body is simply outside your control sometimes. It does weird things. You are only able to control it to a point. This story happens to all of us. When it does, picture me hugging you and telling you to be kind to yourself, love your body, and take fiber regimens like Metamucil or Pure for Men to prevent these sorts of mishaps in the future.
And if you’re one of those lovable shit pigs out there, ignore this slideshow and play away!
After dinner, we headed back to his place. In the door, he asked me an unexpected question: “I bet you’re not on meds, right?”
“I am on meds. I’m undetectable.”
“Oh. But you’re poz, right?”
“Yes, but because I’m on medication and undetectable, my chance of transmitting HIV is basically zero.”
“So you can’t poz me?”
“I thought you wanted to poz me.”
He wanted me to seroconvert him — infect him with HIV. When I told him I was, according to the most recent studies, almost chemically unable to do so, and that I wouldn’t do it to him if I could, he said, “All right, well, I have to go. Have a good night.” Then he closed the door in my face.
This has only happened to me once, in Atlanta. The whole evening was a farce; he had fetishized my HIV-positive status. Guys may fetishize anything about you, from your skin color to your body type to your height. For me, this was quite hurtful and frightening, particularly since he had gone through an entire (very enjoyable) dinner date before communicating this goal. I felt lied to, manipulated, and hurt. It was one of my most rattling dates/hookups ever.
Yikes! This has led to some of the best and worst nights I’ve had as a boyfriend. Nearly all my boyfriends have permitted us to take home a hot guy at the bar, and nearly all my boyfriends have freaked out, gotten jealous, or otherwise regretted the decision. Be warned!
My favorite — except for when you get caught.
More than a year before I moved to Los Angeles, I was on a vacation with my family in Santa Monica. When my parents and sister were asleep in our hotel room, I grabbed a room key and snuck out to bum around down Ocean Avenue and cruise hot guys. I ended up hooking up with a tall blond guy from Berlin in the public steam room of a nearby hotel. It was going great … until a hotel attendant walked in and saw us. They immediately left, probably to go alert a manager, and we had to grab our stuff and run.
Horror stories about kidnapped Americans in foreign countries abound, partly because of Liam Neeson movies and partly because they happen every day. Be careful in places you’re not familiar with, meet guys you want to have sex with in public places before going somewhere more private, watch your alcohol intake, travel in groups with trusted friends, use logic, be sensible, be smart, and have fun.
The risk of playing on drugs is that they can always take you to scary places. Some guys don’t handle drugs well. They get scared when the drugs hit, and they feel like they don’t have much control. If you reach that point, sit down somewhere with someone you trust and breathe until it passes. You might be there a while — that’s OK.
If someone you know is reaching that point, simply sit there with him. He probably won’t want to talk — just let him be calm.
A bad response is not the same as an overdose, which is much more serious and frightening. If no one is sober, call 911 and get him to a hospital ASAP.
I’m a hookup pro. Yet sometimes, because I'm horny or bored, I find myself driving to a house in a bad part of town in the wee hours of the morning to meet someone who is displaying the telltale signs that he’s not who he says he is (reluctant to show more pictures and apparently unable to take new ones, reluctant to text/call, and intermittent responses). Sometimes I dare myself to go through with it, to see where it takes me. But when I’m smart, I turn around and go home, horniness be damned.
Don’t hook up on the beach at night, walking to a phone light 100 yards away. Don’t meet him in a remote place where no one will hear you if it goes wrong. Meet in public, at a bar, or around people. It might seem like a lot of work, but this simple practice will keep you safer than routinely going to private residences of people you don’t know — or inviting them to yours. All the horniness in the world is not worth risking your safety.
For all the bad hookup stories, there are good ones. For all the frightening nights you have when you’re young and still figuring things out, you will have better nights to come. I must urge caution if you wish to play with drugs, since they so easily can lead to unhealthy nights and unhealthy practices. They are a historic problem for gay men, and as such are something I feel need addressing. I’m not antidrug — shaming anything doesn’t make people safer — but I do think there comes a point in any activity, whether it be hooking up, going to the gym, using drugs, or working long hours at the office, when you need to take a step back and ask yourself if you are making personal wellness a priority. Take care of yourself above all other things in life.
Enjoy hooking up, and remember the bad ones make fabulous table talk when you’re gabbing with your friends the next day. Happy Halloween, little devils.