Guy #90 – The logistics of getting a naked stranger in my bed…

Scoring a sex date is often said to be easy.

The truth is that getting a naked stranger in your bed is a logistical nightmare.
As with life evolving on a planet, so many factors need to line up perfectly for random sex to even have a remote chance of happening.

For starters, you have to be into each other. This might be the case for every 25th person I meet online. That’s 96% of potential hook-ups that will never happen.

Second, you have to be horny.
It sounds like a no-brainer, but whenever a cute Guy hits me up, part of the chase is done. On Grindr Hi means I want to do you. Often being wanted is enough to satisfy my ego.

Because for a sex date to happen at least one person must have access to privacy, while the other must have means to travel. Guys who live with their parents, Guys who don’t have a car, Guys who don’t have money, Guys who have to get up early the next day, Guys who have roommates, Guys who have boyfriends…The road to casual sex is paved with obstacles. For a sex date to materialize you have to ask yourself: Do I want to go down that road only to spend a good fifteen minutes with someone who’s probably fatter than his photoshopped selfie?

Guy #90 was about as traditional as a sex date can be.

Our date started on neutral ground, at a bar. As expected, his selfie had been a bit of a lie, but having already invested time in this Guy I decided to stay the course and get him naked in my bed somehow.

While I appreciate casual hook-ups that start with a conversation, Guy #90 and I didn’t have that much to talk about. He was nice. I was nice. He had hobbies. I had hobbies. He liked pets. I liked meat.
We managed to chat our way through two non alcoholic drinks, but the more we talked the less we had in common.

Which is why I steered the conversation in the direction of my bedroom.

The only thing standing in between us and my bedroom was a 15 minute drive to my place. I figured the two of us could squeeze out another 15 minutes of small talk. Besides, it’s perfectly acceptable to start foreplay in a car when you’re on a date with a stranger. If we were to run out of things to say I could always put my hands on Guy #90’s leg and let our hormones carry us over the social awkwardness.

The social awkwardness actually began when my car wouldn’t start.

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Instead of initiating foreplay on our way home we sat on the pavement, waiting for my mechanic to show up. I don’t remember what we talked about. I do know it was exhausting coming up with things to talk about.

Still, when you’re halfway down the road to Mordor it’s silly to turn around and head back.

When my mechanic arrived it felt strange to introduce him to Guy #90. It felt even stranger when my car couldn’t be fixed on the spot, meaning Guy #90 and I had to fetch a ride from my mechanic, a man who was smart enough to figure out the format of my relationship with Guy #90.

Once we were alone at my place we finally had the very sex that had been on the menu for hours. We just had to consume each other. All the frustration from the waiting and the exchange of increasingly irrelevant pleasantries needed an outlet.
The sex was hasty though. I mostly remember being relieved I had succeeded in getting another somewhat cutish naked stranger in my bed. The sex celebrated the completion of an obstacle course, not so much the bond we had, or the attraction we felt.

Afterward I managed a friend of mine to give Guy #90 and me a ride back to his hotel. It had never been my intention for Guy #90 to intertwine with my social life, but logistically speaking I had no other options.

When the date was finally over I was relieved, but I hadn’t experienced any relief. I imagine Guy #90 felt the same.

I guess my mechanic got the most out of our time together.



Relationship summary:

LENGTH: 4 hours
FORMAT: Attempted sex date
SEX SCORE (0 = The word “Intercourse” <–> 10 = The best sex ever): 7

Guy #56 – Horny Loner, Sneaky Cheater.

Hotels are great for cheating. One might even say that infidelity supports the Hilton the way zombies define The Walking Dead.

Guy #56 was funny, cute, smart, Asian and not single.

I was single and had a hotel room at my disposal.

As predicted by Newton, sneaky cheaters and horny loners are attracted to each other.
Craigslist did the rest.

Guy #56 had made it very clear things needed to be discrete. I had made it very clear I was fluent in getting Guys past the lobby.

It was obvious Guy #56 was nervous about making it to my room unnoticed. Unlike me he was a local. People knew him, and his husband. His husband’s entire family knew him. He was part of the community. And it was the holiday season. Christmas is the worst time to be caught cheating.

Of course being a horny loner I didn’t care much for any of that. I just wanted Guy #56 up in my hotel room because he was funny, cute, smart and Asian.

Once we were confined to the safety of my hotel room Guy #56 and I clicked like peanut butter and chocolate. It was unexpectedly good, but it felt like doing something bad. His husband would be devastated to learn his better half was going to third base underneath someone else’s mistletoe.

At the same time I felt I was doing Guy #56 a favor. Something was obviously lacking in his marriage. I got the impression he loved his husband, except in the company of his husband’s family. Guy #56 probably only cheated during the holiday season.


We had a more than jolly good time in my hotel room two times. Our last date was on December 24th. In between sex he described me his Christmas dinner as he would be cooking it the day after.

The two of us could have enjoyed each other’s company the entire night. Sadly, Guy #56 needed to be home in time to defrost a turkey.
“Why don’t you guys just do noodles?” I asked.
“My husband is white,” Guy #56 said.
“Of course he is. I can tell you’re into white guys.”
I really liked how Guy #56 went along with my little racist joke. There’s nothing quite as intimate as exploring each other’s dark sides. Actually, there is: There’s nothing as intimate as exploring each other’s dark sides naked, which is what Guy #56 and I did.

A lot of times when I meet people I get bored by how serious they are about everything. I find sarcasm and dark humor to be notably lacking in many Guys. Guy #56 was my kind of dark. He could have been my husband in a parallel universe. I might very well have been the one going solo under my own mistletoe. Perhaps I will someday.

It wasn’t the first time I had sex with a sneaky cheater, but this time it felt bad for my karma.
Guy #56 struck me as a wonderful person. He left me with the realization that great people can be sneaky cheaters too.

It makes horniness all the lonelier for it.



Relationship summary

LENGTH: 2 x 2 hours
FORMAT: Loving sex dates
SEX SCORE (0 = Eating a mistletoe <–> 10 = The best sex ever): 9.5



Guy #6 – Sex with chocolate chip cookies…




Did I mention Guy #5 had a boyfriend?

Well, he did and a few days after spending a night at Guy #5’s place while his boyfriend was away on business, he introduced me to this boyfriend. In doing so, he also introduced me to the concept of open relationships.

Guy #5’s boyfriend would become Guy #6, in case you didn’t see that one coming. It would be my first ever threesome.

Guest starring in a couple’s sex life can be intense. It will teach you there’s no such thing as “just sex”. Just because a relationship is open, does not mean sex isn’t an issue.

And while the idea of a threesome might seem like a good one in movies and fantasies, the reality of it is that, at any given moment, one person will get less attention than the other two. That’s just a mathematical certainty. Add even a smidgen of insecurity to a threesome and you got yourself a cock fight.

As I was doing things with Guy #6, he would very often look at Guy #5, his eyes begging permission for whatever he was doing with me.

Although Guy #5 was very involved in our threesome at first, the night ended with me and Guy #6 having sex, while Guy #5 was sitting upright on his side of the bed, eating cookies, passively waiting for the sex to be over.


Granted, it wasn’t a cock fight in the traditional sense, meaning there weren’t any direct casualties. People did get hurt, though. At least, I think they did. I felt hurt after Guy #5 had grabbed his bowl of chocolate chip snacks, signaling that the party was over. Perhaps it was wrong of me to continue having a go at Guy #6. Maybe I should have called it quits when cookie #1 entered the scene.

At the time, Guy #5 and Guy #6 had been together for over half a decade. Sex may become a commodity over the years, but intimacy doesn’t. Despite the pure sexual tension I had seen in gay porn, to me it seemed impossible to tread on another couple’s sex life without trespessing on their love life as well.

As I was busy performing oral duties on Guy #6, his boyfriend actually offered us both a cookie. Led by a different kind of hunger, I rejected his generous offer. Guy #6 did have one, though. I guess he wasn’t in a position to reject anything his boyfriend threw at him.

In all fairness, I should point out it’s perfectly possible that the cause of all the tension was me. I had been nervous from the moment I realized I was going to be part of a threesome. I was afraid my relative sexual inexperience would be a factor. I wondered if perhaps there was some kind of “threesome etiquette” I ought to know about. Perhaps my own insecurities had transposed onto Guy #5 and Guy #6.

Then again, who in their right mind starts eating chocolate chip cookies in the midst of a threesome?

I guess sex is always an emotional experience. It’s part of what can make it fun. In movies and fantasies at least.
As you might expect from a site called, Guy #5 and Guy #6 weren’t my last threesome. After my first experience I concluded it was an area worth exploring, but not chasing.

Somehow Guy #5 and Guy #6 had struck the right balance with me.



Relationship summary:

LENGTH: 7 years and counting
Sex date followed by friendship that lasts till this day
SEX SCORE (0 sitting next to a smelly person on the subway and 10 being the best sex ever):




Guy #4 – Thirty seconds of horror…


If you start exploring the world of gay sex, you can’t avoid that moment when a guy starts taking an interest in your anus.

During my previous sexual escapades, I had managed to avoid any anal contact. Guy #4 however wanted to do that thing that gay sex is commonly known for. Even scarier, he wanted to do it to me.

The thing is, while I knew most gay guys like anal sex, the concept never played a role in my secret fantasies my ‘straight self’ felt guilty for having. For a long time I had convinced myself I couldn’t be gay because I had no interest in sodomy. Even in my gay head a vagina seemed way more comfortable, for everyone involved.

Yet I also knew I enjoyed exploring my own sexuality. At 24 years of age it was a much needed exercise. All in all I met four different guys through a paid phone service. The fourth one was by far the nicest, most honest and most experienced. He would be the one to finish this chapter and… well, take my virginity. For real.

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Not to offend any gay rights movement, but unless you’re a turkey, an asshole is not made to insert things. It just isn’t. Just because you can, doesn’t mean that’s its function. As I was being definitively devirginilized, I couldn’t imagine how anyone could enjoy anal sex. I tried to ache my way through it for about half a minute and then suggested we’d retreat to doing other stuff.

Guy #4 didn’t mind. And apart from those thirty seconds of horror I actually had a really good time with him. He would become the first person I ever spent a night with.

In retrospect, spending the night with someone was much more relevant than those thirty seconds. Still, for the first time I found myself empathizing with people who consider anal sex a good idea. To inflict joy and pain simultaneously creates an extremely intimate tension. And seeing as relationships are basically about inflicting joy and pain, it did seem natural something like that is reflected in the sex.
But I guess I wasn’t ready to embrace any of that, not yet anyway.

Next morning my sex date woke me up by putting his arm around me. I had never woken up like that, so at first I was surprised, followed by pleasantly surprised. It was nice to be awakened by such a nice gesture.
Guy #4 didn’t rank too high on attractiveness. Nevertheless he was the best sex I had ever had, up till then that is.
Unlike my previous guys, Guy #4 was out of the closet. He seemed okay with being gay. That sense of comfort must have reflected itself in the sex, save for those thirty seconds of course.

But I did feel conflicted. In my head I was still just a bicurious guy doing other guys to get at least some sex. It was supposed to be just about sex, not intimacy. I couldn’t get myself to like the fact I was liking this so much.

Also, as we woke up together Guy #4 told me he had completely fallen in love with me. He said it kiddingly, or at least I think he did. I honestly don’t remember how I reacted, but I imagine it must have been distant. His use of the word ‘love’ was probably the main reason I didn’t see him ever again.
That’s a shame, because Guy #4 had just given me the biggest compliment anyone had ever given me, not to mention the best sex I had ever had. I should have given him credit for that.

Thank you, Guy #4.


Relationship summary

Length: ± 10 hours
Format: A loving sex date
Sex score: (0 being an Oprah moment and 10 being the best sex ever): 5

Guy #3 – In the Oval Office…




When a guy is in a committed relationship with a woman and has sex with another guy on the side, a bedroom becomes a crime scene.

Guy #3 cheated on his girlfriend, with me, in her house and on her bed. I was nervous due to my relative sexual inexperience. Guy #3 was nervous for fear of his girlfriend showing up. He constantly checked his phone. He would freeze every time he heard a noise coming from outside. I could see he was trying to enjoy sex, but his mind was preoccupied with consequences of getting caught.

To Guy #3, it must have been like having sex in the Oval Office.

Still, I wasn’t complaining. Guy #3 was the first guy I found myself somewhat attracted to. He looked like a metrosexual hooligan, if ever there was such a thing. He was manly, simpleminded to the point of stupidity, but he obviously took good care of himself and his body.

He had made the effort to spice up the bedroom with candlelight and music. He even threw a bit of hot wax over my body at one point. It instantly taught me SM is not my thing, but I was glad to add something to my short list of experiences, even hot wax that got impractically messy once it cooled down.
Everything indicated that Guy #3 wanted to enjoy having sex with me. It was a pity he couldn’t allow himself to.

Guy #3 asked me if I liked doing poppers. I had never done poppers before. In fact, at the time I didn’t even know whether poppers were something people smoke, eat or inject.
‘Poppers aren’t really my thing,’ I said, pretending to know what I was talking about.
‘Do you mind if I have some?’ Guy #3 asked.
‘Not at all,’ I said, all too eager to find out what poppers really were.

The reason Guy #3 did poppers soon became apparent, though. To him, it was an amnesiac: Each and every time he vigorously sniffed the contents of this small flask, filling the room with the invasive smell of a freshly cleaned public washroom, Guy #3 forgot about his girlfriend for a good 30 seconds. It was during those 30 seconds that our sex was somewhat hot, save for the air of chemically induced arousal.

After we were finished, Guy #3 did his best to erase all hints of my presence. The sheets were sprayed with air freshener, the floor was meticulously checked for any ‘foreign’ objects, candles were blown out and put back in storage. What struck me was the eagerness Guy #3 had to clean everything up. The thought of his girlfriend must have really scared him.

Guy #3 and I ended up seeing each other on two occasions. Our second date got cut short because a certain girlfriend was about to come home unexpectedly. I guess I should consider myself lucky I was given time to put on my clothes before Guy #3 frantically showed me the door.

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Guy #3 did ask me to come over a third time. I didn’t. I felt sorry for Guy #3 and his girlfriend. Although I was exploring the world of gay sex, I still considered myself to be a bicurious straight guy who couldn’t get himself a girlfriend. I wondered what I would be like in a relationship with a girl in terms of fidelity, if I would be anything like Guy #3, leading a closeted double life. To me, it seemed like a lonely prospect.

On the plus side, I finally got to learn what poppers are.

I have Guy #3 to thank for that.



Relationship summary:

Length: 1 x 30 minutes + 1 x 13 minutes and 23 seconds
Format: Sex date
Sex score (0 being phoned by a telemarketer during dinner and 10 being the best sex ever): 3.5

Guy #2 – A much needed shower…



If there’s one thing that sets humans apart from animals, it’s post-orgasmic guilt.

It’s that moment one sobers up in the time span of literally no more than a few heartbeats, when you realize Kleenex can wipe anything but the shame off your body.

You see, when you anonymously meet a guy through a paid phone service and subsequently have sex with a complete stranger once, it’s easy to do it twice.

The act of sex was still mostly a mystery to me, but the act of meeting up a total stranger for the explicit purpose of having sex already felt strangely habitual. It had been about a week since I lost a decent chunk of my virginity. I was proud of having some sexual experience to speak of. That pride must have inspired me to hook up with yet another guy, another unknown whose voice I had heard on a phone box.

I reckon it must sound like a sad concept: Back in 2006 and perhaps still today, thousands of guys look for sex over the phone. It’s the perfect medium to hide yourself. I was hiding too. My first steps into active homosexuality were not something I would tell my mother about. I had confided my one sexual escapade in a few close friends, but to the rest of the world I was still a heterosexual virgin in search of a girl friend.
Phone lines were the perfect tool for closet cases such as myself, and Guy #2.

Guy #2 claimed to be a straight guy who simply wanted to experiment. I advertized myself like that as well. As if to make a point of his heterosexuality, Guy #2 had put up straight porn on his television, no doubt in an attempt to throw a little eroticism into the equation. The porn somehow added to the overall feeling of sadness I was having.

Things started getting a bit weird when I found out that, between Guy #2 and me, I had the most experience. I had kissed a naked guy the week before. Guy #2 claimed to have no sexual experience whatsoever, which I suppose made me the ranking officer on deck.

Needless to say, sex between two people who know so little of each other, so little of themselves and even less of sex itself is pitiful. It was about as coherent as Ashley Simpson lip syncing her way through Saturday Night Live, that’s how inept we both were. It didn’t help I wasn’t at all attracted to Guy #2. The only reason I was doing this awkward routine called sex was the fact I hadn’t had any sex for the first 24 years of my life. I figured I had to start somewhere.

The guy’s name was the same as my dad’s, by the way. It made not thinking of my father difficult. That little hint of incest distracted me more than the straight porn in the background.

It wasn’t long before I just wanted to go home again, to take a shower. My previous sexual encounter had already taught me there’s an easy way to end a gay date quickly: Coming.

Coming can come at a price, though, and that price is post-orgasmic guilt.
Me and Guy #2 both felt it.
‘I think I will like girls better,’ was the first thing Guy #2 said after reaching for his Kleenex. I couldn’t care enough about his thoughts to be offended.

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I imagine most people know what it’s like to have sex that’s regrettable. I reckon it happens because it’s deceptively easy to lose your sense of worth sometimes. My sense of worth wasn’t in great shape, in large part on account of my near everlasting virginity.

Everything has to start somewhere, or so I figured, foregoing the fact that Guy #2 and I had nothing in common, except for our loneliness and confusion perhaps.

However, I had noticed how Guy #2 had complimented my looks, just like Guy #1 the week before. Sure, it’s the easiest compliment to give on a sex date, but I got the impression they both meant it. Even though the shower was long and cathartic when I got home, I did feel more attractive than usual.
Feeling attractive proved good for my sense of worthiness.

Guy #2 and I did not stay in touch. I guess we both reminded each other too much of our post-orgasmic guilt. It happens on sex dates. If you try something intimate with someone you have absolutely no connection with on any meaningful level, it’s impossible to not feel awkward about it afterward.

Yet somehow, after that much needed shower, I felt more attractive than I had in a long, long time.

I have Guy #2 to thank for that.



Relationship summary

Length: 20 minutes
Format: Introduction to sex
Sex score (0 being groped by a Muppet and 10 being the best sex ever): 1 

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