Guy #12 – Gandalf at a Tupperware party…





Picture yourself a private pool in a remote garden, late at night, filled with six guys, two of which are couples that start making out. That leaves two guys, sitting in a pool, surrounded by four people that just initiated foreplay.

I know, it has all the makings of a spectacular orgy.

Sadly, one of the single guys in that pool was me and the other one was Guy #12.

Sexually speaking, Guy #12 didn’t scare, disgust or in any way affect me. There had just never been even the slightest bit of sexual chemistry between us. Whatever I saw myself confronted with, it simply wasn’t my thing and I couldn’t see it ever being my thing. One might argue I felt like Gandalf at a Tupperware party: Intolerably lonely.

Moments after the two couples had started making out, Guy #12 grabbed his chance and, well…grabbed Gandalf by the balls. The worst part is Gandalf let him.

Of the six people in that pool, five were clearly in the mood for sex and all five had found someone who they wanted to have sex with. Gandalf was the odd one out, but he didn’t feel like spoiling the sensual tension that had spontaneously arisen.

What followed was an uncomfortable game of give and take in which Gandalf found himself weighing his personal boundaries against his desire to fit in. He’s not used to dealing with that kind of pressure.

I leave it to your imagination to decide how far Gandalf ended up letting Guy #12 go. I’ll only say it was further than anything he could ever have enjoyed with someone like Guy #12. It was yet another strike of regrettable sex, so afterward that’s what Gandalf felt: Regret. It’s never good for your ego to have sex out of politeness.

Five out of six people in that pool were having fun, or at least so it seemed. Most of it took place under water at night, so I’m not really sure what everyone was doing. All I knew was that Gandalf wanted it to be over. While Guy #12 was clearly having trouble believing he had gotten so lucky, Gandalf was silently loathing himself.

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I sometimes find myself complaining when I strike forgettable sex, but it’s people like Guy #12 that remind me how nice it can be to forget sometimes. Whenever I think about the sex with Guy #12 I tend to dissociate a little.

Pretty much what you’d expect from Gandalf at a Tupperware party, trying to do the polite thing.




Relationship summary:

LENGTH: 5 or 6 years, give or take, on and off
FORMAT: Friendship, let’s just leave it at that
SEX SCORE: (0 = being Gandalf at a Tupperware party <–> 10 = the best sex ever): 0

Guy #11 – The hunter…





The first and only time I drank so much alcohol it made me vomit was the night I kissed Guy #11. I don’t think he knew. The kissing happened after the vomiting, in case he’s reading this and wondering.

At the time I cruised our local gay scene on a weekly basis. It consisted of about thirty guys, a handful of women and one dress queen.

With ever increasing proficiency I was mastering the art of picking up total strangers for the purpose of having sex.
The local gay scene was small, but it wasn’t static. People would often pop in and out of the closet, so every Friday night I would see a few unfamiliar faces. Plus the gay scene expanded as time progressed.

Still, some nights were slower than others. This one in particular ended with me and a friend of mine leaning against the bar, staring at a depressingly empty dance floor. We had both come for the hunt but had failed to score some prey.

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Perhaps I should apologize for initiating the first kiss, so shortly after I had vomited. Then again, if it wasn’t for all the alcohol, Guy #11 would never have gotten to have sex with me. I had become good at sensing when a guy was into me. It never crossed my mind Guy #11 would object the idea of us kissing. And he didn’t, because we ended up doing a whole lot more than just kissing. He should probably count himself lucky I vomited before and not during.

I never really intended to have sex with this friend. But after I had dropped him off at his house I had somehow found an excuse to park my car and somehow ended up on my friend’s porch, where I somehow ended up kissing him. I wasn’t really sure why I did that. I guess a hunter doesn’t like to go home empty handed.

Fortunately, Guy #11 and I pretty much shared the same sexual lifestyle at the time, so the one-time sex didn’t make things awkward between us.

Him reading about the vomiting might.



Relationship summary:

LENGTH: 7 years and counting
FORMAT: Friendship interspersed with one drunken instance of sex on a porch
SEX SCORE: (0 = Seeing ALIEN for the first time <–> 10 = The best sex ever): 7.5

Guy #5 – Grabbing myself by the balls…




December 25, 2007 was the only Christmas I ever spent alone.

You see, after having sex with a lesbian and four guys I met over the phone, I got my MSc. in Psychology and moved from the Netherlands, Europe to Suriname, South America.

I went from slowly tentacling my sexuality in a safe and familiar environment to being a socially phobic recluse in what I still considered to be a banana republic.

Throwing myself into such a lonely adventure has proven to be one of the best decisions I ever made, though. It forced me to grab myself by the balls once again to get me to overcome my fears.

After spending a year in hiding I finally made the decision I needed to have sex again. After a full year without any sex my virginity started growing back on me.
However, anonymous phone dating services were not a thing in Suriname as they were back in the Netherlands. I had to think of something different, something more daring.

I had to go out.

Religiously determined to go home with a guy, I dragged myself to the country’s only gay night club. I went alone. It petrified me, to stand at a bar in a place with people, all of whom could watch me, observe me, judge me and make fun of how desperately I was trying to look attractive. I could actually see people watching me. In banana republics with only one gay nightclub, no new face goes unnoticed, especially not a white one. They say social phobia only plays out in your head, but in this case I just knew: These people are watching me.

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I’ll admit I had some confidence issues at the time. I wasn’t even sure what I was really expecting to happen. How do hook-ups usually happen? How do people go from being total strangers to ending up in each other’s arms naked in the time span of just a few hours? I had no idea. But I did know one thing: I was going to go home with a guy. I just had to.

That was the night I met Guy #5.

When he walked in and saw me standing at the bar, he immediately walked up to me to say ‘hi’. His familiarity almost made me think we’d already met before, not at all unlikely in a country the size of Suriname. In fact, I even entered the conversation under the assumption I was talking to an acquaintance of sorts.

I would later find out Guy #5 has the innate quality to make others feel at home. By that time I had already decided the answer to the question Do I see myself doing do this guy tonight? was ‘yes’.

I don’t think I ever had a nightclub hook-up as smooth and easy as the one I had with Guy #5. One thing became clear right away: He wanted me and I was going to let him. I had a lot of fun going down that road together. It would be the first time I ever kissed a guy on a dance floor.

Apart from getting me back in touch with my sexuality, Guy #5 became a good friend who also got me in touch with other people. He gave me a social life in my new environment. Like I said, he’s good at making others feel at home. Sex with someone who makes you feel like that is never a bad thing.

Guy #5 taught me that.



Relationship summary:

Length: 7 years and counting
Format: On and off sex, followed by friendship that lasts till this day
Sex score (0 making out with an accordion and 10 being the best sex ever): 7,5


Girl #1 – The perfect daughter-in-law





Between the ages of 16 and 24, my life consisted of falling for girls I imagined could bear the grandchildren that would make my mother so happy. I got rejected every time. For some reason I always gravitated toward the friend zone as if it was a black hole from which there was no escape.

Except this one time.

I had already experimented with four different guys the month before. This had boosted my self esteem up to the point I was no longer afraid of people with vaginas. It was during this time that I met a girl at this improv class we both attended. We got to know each other and for the first time in my life, a girl didn’t show any interest in my friend zone. The three months I dated her were among the happiest of my life.

Finally, after 24 years, I was able to say I had a girlfriend. And not just anyone. This chick would have made the perfect daughter-in-law! She was funny, smart, sophisticated, witty, creative and independent. It’s not so much that I really wanted her to be the mother of my kids. I was simply thrilled by the fact I had managed to get the kind of girlfriend I had been picturing all those years. It was literally a dream come true.

Even the sex was good. It was intimate, passionate and very loving. And I turned out to be right about vaginas being way more comfortable than anuses. Though I can’t say I ever really got how a vagina works exactly. Of course I was immensely grateful I was finally allowed to come near one, but I could never quite figure out what makes it tick. I did my best and I believe I may have even been successful in some cases.

But I never fully allowed the female anatomy to get through to me. Whenever we had sex, there was a voice in my head that repeatedly said Look at me, I’m having straight sex! I’m actually doing IT with a girl. It created a distance between myself and the sex I was having. I guess on some level I already knew I had been chasing the wrong dream all those years. Girl #1 must have known it too, as she broke up with me after three months.

It was okay, though. For the first time I had met a girl that didn’t reject me. Looking back, that’s probably all I really wanted; someone to make me believe I’m not the Elephant Man. These days I’m thankful for every girl that ever turned me down. They were right to pull me into their friend zone, but at the time all those rejections were quite a burden to carry. Girl #1 shed me of it, at least for a while.

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Of all the girlfriends I could have ever had, Girl #1 was probably the one I needed the most. She knew about my previous ‘experiments’ with guys. She probably also figured I was gay. She allowed me to gently let go of this heterosexual mirage I had been chasing for so long. Now, after 24 years, I had finally crossed it off my to do-list.

I guess Girl #1 gave me the confidence to start exploring more of the gay scene, weird as that may sound.

And while I can’t imagine ever having sex with a girl again, I’m glad to know what it’s like. If Girl #1 had allowed me to chase my dream of pleasing my mother with the announcement of her first grandchild, she would have made the straight lifestyle very, very bearable for me. At the time Girl #1 was the best sex I ever had.
Of course back then I didn’t know yet an anus can be comfy too if used properly.

I know for a fact I’m not the best sex Girl #1 has ever had. She’s been living together with her girlfriend for years now. I very much hope she’s a happy lesbian.

Thank you.




Relationship summary

Length: ± 3 Months
Format: Loving heterosexual relationship including meet-up with each other’s parents
Sex score (0 being the walk to Mordor and 10 being the best sex ever): 7

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 

Guy #1 – If the shoe fits…

The first one is always special, as special as it can be disappointing.

One might say I did Guy #1 out of despair. That’s never a solid ground for any relationship, however casual. But at the time I was already 24 and still a virgin. I avoided seeing The 40 year old virgin because I was afraid it would be too confronting. I was simply very ready to know what having sex was like. That’s why I was willing to compromise.

The reason for my inexperience was ostensibly simple: I had spent years falling hopelessly in love with girls that looked just above average, who grew to like me as a friend and ended up confiding their love life in me, because they so much enjoyed the lack of any sexual energy between us. Those were the kind of girls I envisioned myself with, married, with children, a loving family that goes on holidays together, watches plays, goes to museums and in which I would have heterosexual sex. That’s the kind of dream I was chasing.

It took some years for me to finally realize, accept and embrace the fact that I am in fact gay. Actually, by the time I was on my way to see Guy #1 I convinced myself I was merely being bicurious, having my first sexual experience at age 24. I mean, who wouldn’t try it with a guy by then? For me it was either this or a rubber doll.

The year was 2006. The internet had arrived, but I was too afraid to advertize my sexual quest online, alerting the world of my bicuriosity.
Instead, I assumed a pseudonym and paid fifty Euro cents per minute to listen to voice messages of horny guys. I ended up texting quite a lot with different guys and after a while I had summoned up the courage to go all the way and try to meet up with one.

I had to spend an hour in a train to get to my date. It was a very philosophical journey for me. I was shaking from anxiety and excitement at the same time. I enjoyed how the people sitting around me had no idea who they were facing: Someone who was about to lose his virginity. I couldn’t help but feel proud of what I was doing.

Of course, someone you meet over the phone seldom looks like anything you had in mind. In my case, the disappointment started the moment my date opened his door to greet me: Was I willing to lose my virginity to this unshaven, sweaty and slightly chubby Guy #1?
I quickly noticed something, though: Me and Guy #1 were wearing the exact same pair of shoes. Never before and never since have I ever encountered someone with identical shoes. I guess I felt our sneakers connected the two of us somehow. Perhaps I needed to have sex with an unshaven, sweaty and slightly chubby guy who looks a lot older than he says he is because that’s how I had come to see myself over the years, after a seemingly endless stream of rejections from girls that appreciated my friendship so much. Guy #1 was a reflection of my subconscious.


His apartment was depressingly neat and unimaginative. The view was that of other apartments staring right back at me.
He offered me something to drink. Half a minute later we sat down on his bed and talked. My glass of water was the only thing standing between us and sex. As I drank I spoke of my situation. I explained Guy #1 that this would be my first time with a guy. I said I wanted to explore, not realizing what a sad cliché I was being.

Throughout our date the disappointments kept on coming. His accent was weird and unsexy. I could see he had a lot of chest hair, even though he had texted me otherwise. His breath was slightly bad. He was nothing like any of the guys from my very secret fantasies.
Only the shoes matched. So after finishing my drink I simply asked: ‘How do we do this thing?’

That’s when I received my first kiss. It was one of the most conscious experiences I ever had. Finally, after years and years of wondering if something might be very wrong with me, this guy put his sweaty arms around me, during which he revealed his arm pits were as hairy as the rest, only with longer hair. His rugged cheeks wreaked havoc on mine. The kissing lasted a good 45 minutes. Then we undressed each other. He seemed really into me, but I figured he could easily be pretending, just as I was. I behaved under the assumption the two of us were doing each other a favor by pretending the sex to be extraordinary. It was in fact, just not in a good way.

I had already seen a bit of gay porn here and there, but I knew Guy #1 and I would not be doing any of that stuff. Instead, I finished off by saying I was ready to come, which we then did.

Afterward, I was mostly glad it was over. I was happy to say I was not totally a virgin anymore. That and the fact it was over. Guy #1 offered me another drink. I really wanted to leave, but I asked for another glass of water out of politeness. I didn’t know yet it’s okay for sex dates to be heartless.

As I drank my second glass of water, after the two of us had already put our clothes back on, we talked some more. I’d be lying if I said I remember anything about his life. All I remember are his shoes. It’s probably better that way.

Before I left, Guy #1 said I was always welcome to contact him in case I ever felt like talking to someone about anything. I thought that was very sweet of him. I knew I had no intention of ever meeting or interacting with him ever again, but I genuinely thanked him for his offer.
I felt his loneliness when I left. My guess is he had felt mine too.

The train ride home was equally spiritual. My cheeks hurt like hell, but that didn’t stop me from feeling good about myself for having accomplished my mission of having sex. I wasn’t going to become a 40 year old virgin.

I have Guy #1 to thank for that.


Relationship summary

Length: 1 hour
Format: Introduction to sex
Sex score (0 being a date with Darth Vader and 10 being the best sex ever): 1.5 





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