Dating – Page 5

Guy #83 – By the way, I’m a Nazi.

People go on dating sites because it gives them hope.
Each time you receive a message from a stranger there’s that quiet sparkle of anticipation that this time, yes maybe this time, you have been contacted by a gorgeous, funny and smart underwear model who has seen the inner beauty radiate from your mirror selfies.

Of course most messages we receive on dating sites are a bit of a letdown. Our search for the one often starts off with a healthy chunk of compromise.

Guy #83 was clearly no underwear model. Nothing from his profile indicated that he had any sense of humor. And his message simply read Hi how are you (I get turned off by Guys who don’t have the decency to end such a simple sentence with a question mark.)

On the other hand, Guy #83 turned out to be a doctor. I figured it couldn’t hurt to be on good terms with a doctor, plus I assumed his degree was indicative of some brain power on his end.

Compromise is a powerful trait, one humanity should pride itself for.
It also led to Hitler ass raping Czechoslovakia overnight.

At some point compromise goes from being a virtue to being the pussy’s weapon of choice.

I’m not sure at what point I became a pussy with Guy #83, but I do know I felt invaded like an Eastern European country after I spent the night with him.

Unlike Hitler, there was nothing very wrong with Guy #83. He was just intolerably boring. I very much enjoyed his awesome 24^th floor penthouse, his cooking skills and his designer pillows, but I couldn’t help but feel empty in his presence.

Guy #83 wasn’t unattractive, the food had been great and I was too lazy to go out in the cold, so I had sex with him and slept on his designer pillows.
I did not sleep well.
Guy #83 snored. Call me shallow, but people that snore ought to sleep in isolation. Or be put down.

Few things are quite as agonizing as trying to catch sleep lying next to a snoring hump of human.
I kicked Guy #83, I pushed him around, I went to the bathroom to flush his toilet as loudly as I could. Nothing helped.

People generally think of me as a nice person. In reality there’s a sadistic Nazi living in my brain. It wakes up when others deny me the pleasure of sleep.
Lying next to Guy #83 I pictured him being arrested by German men in uniforms and taken away to a camp for people that snore.
Yes, I know how that sounds, but when your entire existence is someone else’s snoring you can’t help but think the world would be a better place without it. After a few hours of someone else’s perpetual noise making you don’t think about rejecting someone. Rather, you want to cleanse them.

I felt nothing but resentment when Guy #83 curled up against me next morning. Tired from coughing up ways to kill him and get rid of the body, I wanted to sleep, not cuddle.

After my date with Guy #83 I did what any hero of the revolution would do: I ghosted him.
I did not respond to text messages, email messages and Facebook messages. I just didn’t need a doctor that badly.

A few years later Guy #83 suddenly popped up on Grindr, saying Hi how are you. I ignored him initially, but he persisted, asking if there was anything he had done. I finally replied by saying I didn’t feel any connection between the two of us.
Ok he said.

And so ended my relationship with Guy #83.

Thank god.

Relationship summary:

LENGTH: A few months
FORMAT: Months of predictable online chats, followed by one night that seemed to last longer
SEX SCORE (0 = A presidential candidates’ orgy <–> 10 = The best sex ever): 6.5

Guy #82 – Fast Food Sushi.

Guy #82’s first words were hi.
And I was going to let him.

We didn’t speak much afterwards. Which makes telling the story of me and Guy #82 a bit difficult. There’s not much to tell.

Sometimes you just have sex with a random stranger you run into. I believe Guy #82 was quite an easy catch, not the most spectacular one but rewarding nonetheless.
I still have no idea what language he spoke.
To me he was just another brick in my list, another number to add to my Excel sheet that powers this blog.

Guy #82 was like a microwave dinner that tastes like a microwave dinner. He satisfied my cravings without fulfilling my longings. Fast Food Sushi would be my name for him.
He was Asian.
I have a lot of Asians on my list.

My mother would sometimes carefully initiate a conversation about my love life. It always made me uncomfortable. Actually, I was uncomfortable talking about all private matters with my mother, whether they were about sex or not.

I think it’s in our nature to do stuff we don’t tell our parents about. My mother often said how happy it would make her if I were to be happy with someone. Of all the Guys I did, Guy #81 was the first one I ever told my mother about. Whenever my mother inquired about my love life I kept it vague, saying I hadn’t met anyone special yet, or that I wasn’t really looking. I certainly didn’t tell her about Guy #82.
I knew my mother would not disapprove of me having sex with strangers, but she would ask me if it was truly making me happy, if perhaps I was worth a little more than Fast Food Sushi.

Sometimes I wonder how much mothers know of what goes on in the gay scene, and how much we want them to know. My mother hadn’t exactly raised me to be the predatory top Fast Food Sushi came to know and love so very very briefly, nor did I envision myself growing old consuming Fast Food Sushis for the rest of my life.

I wanted love as much as my mother wanted it for me, but it would seem she was less afraid of it.

Fast Food Sushi, like so many of the Guys I ever had sex with, represented my youth. He embodied the idea that I was youthful enough to conquer any Guy I wanted. Guy #82 made me feel pretty for a short while.
Of course talking about him with my mother would be the equivalent of telling her I didn’t feel pretty most of the time and that I did Guys to rid me of that feeling, 82 Guys and counting. It’s never been in my nature to burden my mother with my insecurities.

Rather, I shoved my burden in Fast Food Sushi. It’s what he asked of me when he said Hi.

Relationship summary:

LENGTH: 20 minutes
FORMAT: Hook-up
SEX SCORE (0 = Zombie porn <–> 10 = The best sex ever): 6

Guy #80 – All about the abs…

Guy #80 had killer abs. In fact, his entire body was a cover of Men’s Health.

His penis was as Asian as the rest of him though.

Also, Guy #80 struck me as one of the loneliest individuals I’ve ever come across.

The two of us first met each other at an all male twink orgy one night in Amsterdam. He stood at the bar, quite obviously trying to hide his shyness behind his drink. Being the hunter that I am I temporarily rid him of his insecurity by semi-accidentally touching him. Touch became fun and eventually we exchanged phone numbers. It took me about four texts to get invited to his place.

I kind of enjoyed Guy #80’s loneliness. Or rather I appreciated how his loneliness worked for me.

Usually when Guys are lonely they get clingy, obsessive and mistake sex for the start of a commitment that lasts well into retirement. Guy #80 didn’t do any of that. Instead he made sure he looked good as a means to get people to stay with him.
His house was quite literally covered with magazines about fitness, health and ways to stay in shape after 25. Abs were his obsession. He even did sit-ups in my presence a few times. I think they were part of his obsessive compulsive disorder: I have to do 40 crunches an hour or else the universe will implode.

When I complimented Guy #80 on his body he shrug it off, saying he was fat. I told him I was the fat one. I really was. I recently had a mono infection and had spent four months in bed, eating junk food, watching entire seasons of 24 in a day and eating more chocolate. Still Guy #80 had less qualms with my body than his own.

Which made the sex modestly awesome, save for that Asian penis.

Guy #80 was into me. He made me feel as hot as he was. The difference between the two of us was that when he complimented my penis, I didn’t shrug it off. To Guy #80 the mere fact he was with someone lifted his spirits. His enthusiasm in turn lifted anything I had to offer.

Usually Kleenex signal the end of a sex date, but Guy #80 really wanted me to stay the night. I was happy to oblige him.

Of course I felt sorry for Guy #80 and his low self esteem. Apart from the many, many fitness magazines his house was void of anything personal. It was neat and clean and always prepared for visitors, but I could tell I was one of the few people to have been inside.

In a way Guy #80 reminded me of my former self. I used to be an expert in hiding behind drinks, desperately holding on to your glass even when there’s nothing but ice left. When I first started having sex with Guys I weighed my own imperfections far, far more than I did those of my fellow maters. I often find it’s the most beautiful people who think the least of themselves. It takes time and Guys to embrace your own beauty despite your belief in its absence. It takes time and Guys to let go of doing 40 crunches an hour to prevent the universe from imploding in on you.

Me and Guy #80 spent two nights together, about two years apart. Not long after our last date his Facebook status changed to in a relationship. Not long after that his Facebook wall started showing signs of a social life.

I’m happy Guy #80 outgrew his Asian penis.

Relationship summary:

LENGTH: 1 x 1 hour + 2 x 12 hours
FORMAT: Orgy hook-up followed by loving sex dates
SEX SCORE (0 = Sudoku’s <–> 10 = The best sex ever): 8.5

Guy #57 (Part 2) – Me and my Wikipedia…

Did I mention Guy #57 and I had unprotected sex?

Well, we did. Many times.

It was about a week after our last date when I found out he was dating someone else. I was devastated.
A few days later, I woke up in the middle of the night with the highest fever I ever had. Going delirious on a broken heart is the absolute worst way to lie awake at night.

The next morning I was on Wikipedia matching my symptoms with possible diseases. Of all possible diagnoses, Acute HIV Infection stood out as the most perfect match.

In my heart I knew I was about to become part of a statistic, that small percentage of Gay guys no gay wants to be a part of.

It was impossible to hide my symptoms from my mother. I needed half a day to recuperate from climbing the stairs. Knowing my mother to be the same hypochondriac as I am, I knew she was just as terrified as I was. Not for HIV specifically, but for whatever disease could have possibly struck her son.

I knew being HIV positive would be better than getting leukemia or some other lethal Wikipedia article. At the same time I was most afraid of having to tell my mother that her son had come down with a case of HIV. I didn’t even go there in our conversations. I acted cool and did my best to hide my worries. In response, my mother did the same.

When my symptoms didn’t disappear after two weeks I finally went to see a real Wikipedia, my doctor. I started off my consult by telling my doctor I was HIV positive. When I explained what I had done with Guy #57 my doctor more or less agreed that HIV was indeed probable, given my symptoms.

I emailed Guy #57 to say I was being tested for HIV. It wasn’t the kind of email I enjoyed writing to the first Guy I ever fell in love with. Guy #57 never responded on the issue, which made me worry even more.

All in all I spent three weeks being absolutely sure I somehow had to tell my mother I had done that one thing she had advised me not to do with Guys. I spent a lot of time on Wikipedia those weeks, constantly on the lookout for a diagnosis not as bad as HIV. I already pictured myself being surrounded by people acting politically correct toward my HIV status. In my mind it had already become a part of my identity: Oh, that’s uncle Lennard, he’s the gay uncle who has HIV from sticking it up a Guy he dug for a weekend, but we don’t treat him any differently.

I was quick to loathe my new self.

One of my best phone calls ever came from my doctor, when he called me to say I had a mono infection. I would have jumped in the air, but instead stayed in bed for the next four months.

A mono infection sucks, but those four months were good for me. I watched all eight seasons of 24 in as many days. Things did start to become boring after a week or so. 24 isn’t half as exciting the second time.

A mono infection sucks, but it beat being HIV positive. I could tell my mother was equally relieved. Upon hearing the news my mother and I hugged each other, that’s how glad I was I didn’t have to talk about her son and his bareback escapades.

A mono infection sucks, but some people get other calls from their doctor. I’m not sure what’s worse: Thinking you’re HIV positive or knowing you’re HIV positive.

For those that know, I hope the latter is better.

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 24^th. 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 #55 – Post-orgasmic cam session cool down.

When it comes to technology I always lag behind.
I survived the 1990s without internet. I didn’t get my first cell phone until 2002. I held on to this Nokia heavyweight until 2012, when Guy #115 gave me my first smartphone out of pity.

I was among the last privileged white people to go on Facebook, Twitter and Instagram.

Technology in itself doesn’t repel me. I’ll buy it when I need it, not a moment sooner. If a trend is lasting it will find its way to me eventually.

By the end of 2009 I started exploring the world of MSN. To me it was like talking, only with fingers and usually not with people I knew.

Some conversations I had on MSN were okay, most were boring and pointless.

Until one day Guy #55 told me my laptop had a webcam.

Guy #55 was about 4000 miles away from me. I have no idea how we got to talking with each other, but the short version of the not so long story is that we ended up showing off our masturbatory skills in front of our respective webcams.

Cam sex was interesting.

I knew I would never make the effort to meet let alone do Guy #55 in real life. That made everything I said about how turned on I was a bit of a bright white lie.

A bright white lie in this case is typing something like I want to feel that cock inside of me so bad right now while in reality I was thinking It´s frustrating to type with only one hand. Why aren´t laptops with webcams ergonomically prepared for people engaging in cam sex? Surely the inventors of the web cam knew what it was going to be used for? It’s impossible to masturbate and type at the same time. Both require a completely different posture. So you either have to constantly interrupt what you’re doing or clumsily type with one hand while your eyes are mostly focused on seeing what the other Guy is doing.

Cam sex requires a lot of multitasking for a man.

The reason I engaged in a long distance cam session with Guy #55 was that I had never done it before. Like I said: I never look for technology. It always finds its way to me and when it does I usually end up feeling clumsy and incapable at first.

In fact, few situations are more awkward than a post-orgasmic cam session cool down with a stranger. There’s no cuddling, just plain naked awkwardness and still only one hand to type with. Figure out why.

;)

That’s what I ended up typing after Guy #55 and I had both cammed what we came for.
;) was the best lie I could do on one hand. I wanted to close my laptop and take a shower, but even at 4000 miles I chose to stay polite.

The most exciting part of ‘being’ with Guy #55 was actually the realization we live in an age where we can transmit our naked selves over thousands of miles. For free. As someone with vivid memories of the 1980s the technology was more exciting than Guy #55 itself.

They should design webcams that automatically fade to black five seconds after coming. It would have been the most honest way to progress my relationship with Guy #55: I honestly wanted it to be stopped dead in its tracks and never to be spoken of.

Instead Guy #55 and I ended up chatting for a while. I was despising my own politeness.

Guy #55 started insisting on meeting one day.

After our first and only online encounter he would regularly hit me up on my dating profiles. It’s not that I didn’t like him. He was just immensely focused on meeting up with me. It became a bit of a problem a few weeks later, when I moved back to our common home country, where distance is often measured in feet.

Politeness never ends in a spectacular fashion. I simply kept responding less and less to his messages, until I ignored him completely, regardless of how close we were. It has been well over two years since he tried to hit me up online.

I just realized that means he kept on trying for four years straight. Perhaps that means I wasn’t as clumsy as I felt.

I guess I’m better at technology than I give myself credit for.

Relationship summary:

LENGTH: 4 years
FORMAT: ;)
SEX SCORE (0 = Onion flavored toothpaste <–> 10 = The best sex ever): 2.5

Guy #54 – Saying ‘No’ to Hungry Bottom…

The world of sex dating is weird.

Total strangers can commit the most intimate acts.

Right now I have my phone lying next to me. I just checked Grindr. There’s a 46 year old Guy named Hungry Bottom looking for a fun top just 3000 feet away. He says hi. He doesn’t have a profile picture. Plus he’s 46, which is kind of stretching the age envelope for me. Then again, I can be a fun top if I want to.

I was that one time with Guy #54, back in 2009.

We had met online and later in my car.

If it wasn’t for the world of sex dating we never would have met. He was like Hungry Bottom in search of his fix.

He was around my age and not particularly attractive to me. As he stepped into my car I wondered if I really wanted to have sex with him.

The drive to my hotel room took about 30 minutes. 30 minutes of obligatory chit chat can be an eternity on sex dates, but not with Guy #54.

Sometimes nature has a way of bringing good people together. Guy #54 turned out to be someone who knew where to get weed in Wisconsin. It’s the kind of people I like knowing.

I don’t remember anything else that we talked about, but I do remember it being very pleasant. We laughed a lot, understood each other’s minds. After about 5 minutes of driving I found myself becoming attracted to Guy #54.

While I still had trouble finding Guy #54 physically yum, it did feel good to see how glad he was to be with me. It can actually be kind of a turn on if you have the power of turning someone else on, just by being naked. Plus I felt completely at ease with him, cracking jokes all the way through the sex itself. Sometimes it’s refreshing to talk a lot during sex.

For a good two hours we were like best friends on benefits.

Afterward I drove him back home, where we said goodbye to each other in a warm hug. We both knew we would never see each other again.

As pleasant as our friendship had been, we both knew it had run its course. It’s just inherent to sex dating. Sometimes you meet people you actually become friends with. And other times you meet people that are just there to give your ego a push in the right direction.

That’s what Guy #54 and I did for each other.

Presently, I give 46 year old Hungry Bottom very little chance of finding his one true top in me. My ego has been pushed enough over the years.

Casual hook-ups are something of a psychological experiment, a way to meet someone on account of his hormones, or possibly a lack thereof in the case of Hungry Bottom.
Sex is a great way to get to know someone. It reveals someone’s strengths, insecurities, (mis-)conceptions, even hopes and dreams. Sex lets you figure out what makes a person tick.

Now that I’ve had my share of Guys like Guy #54 I don’t think I have to meet Hungry Bottom to find out what makes him tick. Guys on Grindr are often very much alike these days, especially when they’re called Hungry Bottom.

The world of sex dating is weird. It’s not monogamous, but it’s monotonous.

And that seems to be a choice.

Hungry Bottom would have much better odds if he had made the effort to say more than just hi.

Perhaps I sound old, but these days people don’t seem to be interested in hungry bottoms for the sake of exploration. They’re just in it for the sake of it.

That’s what I gather from Hungry Bottom’s hi. That’s why I won’t be saying hi back.

Thanks to Guys like Guy #54 I can now save myself the trouble of getting to know someone I already know.

Sex dating is weird, because we are all Hungry Bottom.

Relationship summary:

LENGTH: 3 hours
FORMAT: Sex date
SEX SCORE (0 = Minnesota nice <–> 10 = The best sex ever): 8

Guy #53 – Nipples.

Wikipedia says the following about nipples:

Because the “female template” is the default for humans, the question is not why evolution has not selected against male nipples, but why it would be advantageous to select against male nipples to begin with.

Personally I never had a thing for nipples, regardless of what gender they belong to. I never enjoyed a Guy biting mine, no matter how tenderly he tried it.

Except this one time with Guy #53.
Well, two times actually.

Guy #53 was the type that spent a respectable amount of hours in the gym. He took good care of his body. I could tell he was good at taking care of his body, because he took good care of mine too.

What should I make for dinner?
Did Hitler really have only one testicle?
Is it cauli flower or cauliflower?

Those are the kind of thoughts that fill my mind during mediocre sex. The better the sex, the less I think about Hitler’s testicle.

The moment someone starts giving my nipples some teeth action, gravity kicks in and I crash land back on Earth, in the here and now. Nipple action makes me want to abandon sex. No matter how gentle, nipple pain serves no evolutionary purpose. Wikipedia says so.

Yet for some reason Guy #53 knew exactly what made me feel good. We didn’t have a very strong connection, but he was simply incredibly good at lovemaking. His actions were very considerate but equally focused on his target: Me.

So when he started doing his routine on my nipples, gravity did not show up for work.

Guy #53 visited me in my hotel room on two occasions. The second one was the best, because I got to spend a few days looking forward to it.

In terms of sex dates, Guy #53 was probably the best I ever had. The sex defied gravity and there was no emotional bond to worry about.

I hope for his sake he also became skilled in letting gravity do its work. Part of me wanted to get to know Guy #53 better. It just wasn’t on my mind while I was caught up in his teeth action. That’s how good he was. At everything. Twice.

Dates like the ones with Guy #53 make you feel less silly for hooking with random Guys. My sex dates generally featured a lot of social awkwardness. This time the word social was wholly and exclusively expressed in the sex. It was everything a sex date should be and, more importantly, it wasn’t what it shouldn’t be.
I remember nothing of our conversations. The only thing I do remember is how satisfied I felt afterward.

Guy #53 had made me thankful for my nipples.

Relationship summary:

LENGTH: 2 x 2 hours
FORMAT: Sex dates
SEX SCORE (0 = Hitler’s testicle <–> 10 = The best sex ever): 9.8

Guy #52 – LOST…

Wisconsin gets dark at night.

Being the hazel eyed slightly toned latino twink that he was, Guy #52 was my kind of hot in each and every way. I simply had to meet up with him and make my dream of having sex with him come true. He hadn’t shown that much enthusiasm for our date, so when I convinced him to let me come over I did not play hard to get. I persuaded him to give me his address and said I would be there in half an hour. I instinctively felt it would be my only window of opportunity with this Guy.

That was his reply to my See you in 30 minutes!:). He was just barely okay with me showing up at his doorstep. I had to move quickly. I opened up Google maps and discovered that Wisconsin is kind of big.

Big and dark.

Being the expert navigator that I am and lacking a printer, I drew out the roads I was supposed to take on a piece of paper. I figured I was enough of a left-brain thinker to make that work.

It was about 45 minutes later when I first called Guy #52 to tell him I’d be there in five minutes.

Realizing that Guy #52 was barely k with me being there in 30, I started getting desperate around 60.

I really did my best to find his house, but every turn drove me further off the map I had drawn. I ended up on busy highways headed to Chicago and tiny country roads that led to places like ‘Prairie du Suc’ or ‘Sauk city’.

When I called Guy #52 for the third time he tried to guide me in like an airliner being flown by a stewardess. As the conversation continued, so did my anxiety. Guy #52 sounded irritated when he told me he had never heard of the places I was driving through. I said I was sorry. Twice.
I was losing him.

I decided to follow road signs that got me into Downtown Madison and work my way out from there.

I took me another 45 minutes to get back to the point I first got lost. I was running out of fuel and not carrying any money. My phone credit was close to zero. It was now or never.

I called Guy #52.
‘I can see your car,’ was the first thing he said.
I wanted to reply, but my phone ran out of juice that very moment. All I knew was that Guy #52 had seen me. For the first time in a long time I felt hope.

Then I saw someone flickering his lights in an apartment building a block away. My gut told me it had to be him.

To my relief it was.

His place looked familiar. I had already driven by it one and a half hour earlier.

Even though Wisconsin was frozen, I stepped out of my car sweating. I literally had to catch my breath. From driving.

I can’t say Guy #52 and I hit it off well.

He was as gorgeous as his selfies and his k turned out to mean way more than ‘just okay’. But we both had lived through 2 hours of my ineptness as a navigator. Our relationship was based on irritability and ineptitude.

The sex was pretty good, but not what it could have been either. I was mostly relieved I got to have any. I was so busy being thankful for the gift that I almost neglected enjoying the gift itself.
Guy #52 also felt relief. I think the sex made him let go of his irritability.

However, it was already late and both of us had lives the next day. Guy #52 told me he was busy moving to Milwaukee, wanting to try his luck there. I jokingly said I know where Milwaukee is on the map. Guy #52 did not laugh. Maybe it was too soon for jokes about my ineptitude.

Fifteen minutes was a really short time for being with Guy #52. I avidly wished it could have been longer, but I think our key traits, irritability and ineptitude, resurfaced after we both had our relief.

I never saw Guy #52 again.

Relationship summary:

LENGTH: 2 hours and 15 minutes
FORMAT: Searching for each other, followed by 15 minutes of sex
SEX SCORE (0 = The taste of Donald Trump’s hair <–> 10 = The best sex ever): 8

Guy #51 – Once, you go black.

A lot of Guys take offense to people that write about certain preferences on their dating profiles:

Not into Asians
Looking for black cock
Latinos move to the front of the line

I never got why any of this is offensive.

Personally, I don’t have much sexual experience with black Guys. Truth be told I’ve never felt much sexual chemistry between me and ebony. Whether the preference on my end is conditioned or innate I don’t know, although being as white privilege as they come it’s not unlikely my lack of sexual interest in black Guys is at least partly because of my inherent racism.

Which is exactly the reason why I would never share my racial preferences on my dating profile.

I actually had a very nice date with a black Guy once.
Guy #51 was a lawyer. I asked him questions about how to get away with murder. It wasn’t really the kind of law he specialized in, but he went along in pondering various crime scenarios with me.

The reason I ended up at Guy #51’s house was simple. I had set myself on a mission.

It was my mission to have sex with a black Guy at least once, which I suppose is the gay scene equivalent of me bragging about having this one black friend.

It took me all but an hour to hook up with the first cute black Guy I found online.

The sex was interesting.

My personal experiences taught me Asians tend to have smaller genitalia. Guy #51 confirmed another stereotype for me. There’s size and then there’s size. There’s penis and then there’s Cape Canaveral.

Impressed as I was, I didn’t really know how to handle it. Having done so many Asians I felt like a hairdresser whose comb had just been replaced by a brush cutter. I was impressed, but equally inept.

I very much enjoyed being with Guy #51, but mostly because he was the kind of lawyer that would help a stranger get away with murder. Sexually though, he wasn’t really the Guy from his pictures. He was a little fat and a tad too hairy, which I felt bad about, because I really wanted to be attracted to Guy #51. It would be key to proving I wasn’t in any way racist.

Things were very cuddly for a sex date. It’s the best I could do. It was nice being intimate with Guy #51, but it never quite turned me on, I suppose because I was consistently reminding myself I was being intimate with a black Guy, showing the world how much of a racist I wasn’t.

Not the kind of thought process to expedite any arousal.

So many of our preferences are variables we have so little control over: cuteness, eye color, hair color, body type, dick size. I always live under the assumption I know my preferences, yet I often find myself surprised by the people I am attracted to.

After going black with Guy #51, I didn’t have sex with another black Guy until Guy #167 came along. I didn’t consciously avoid having sex with black people. It just never happened again, nor did I pursue it as avidly as that one time with Guy #51.

I don’t understand why it would be racist to have a sexual taste in race, but I also don’t get what exactly turns me on and off, and how much of my inner workings are of a benign origin.

I do understand never to rule anyone out on a dating profile.

Relationship summary:

LENGTH: 3 hours
FORMAT: Sex date
SEX SCORE (0 = The Hindenburg disaster <–> 10 = The best sex ever): 7.5

Guy #50 – Jaws.

When you meet someone online you don’t always get to see their teeth right away.

For instance, braces can be hidden by closing your mouth on all your selfies.

Guy #50 was one of the many Guys I had sex with out of empathy. Once again it was a disaster.

I don’t have anything against people with braces, but Guy #50 reminded me of Jaws from the James Bond movies.

Added to that, he was irritating.

He constantly laughed at his own jokes, which often came out wrong due to his dental deficiency.

He constantly interrupted me, which I thought was unfair. I was way better at talking than he was.

Then there was the fact he talked very loud. Everybody in our vicinity could hear him and his teeth. People looked up and saw Guy #50 laughing as if he was controlled by a ventriloquist. They could also see me, cringing my way through the ordeal. Standing in line with him at Taco Bell was what purgatory must be like.

As a result of the social awkwardness I wanted me and my date to end up somewhere isolated as quickly as possible. I knew people were staring at me over the edge of their tacos.

But Guy #50 insisted on eating our food at Taco Bell. That’s the thing with purgatory. It always lasts longer than you expect.

It was obvious Guy #50 was very lonely, having just moved to the city from Mexico. Maybe he actually felt at home in Taco Bell. It was the most Mexican thing our wintry Wisconsin had to offer.

As the evening progressed I came to realize Guy #50 was a normal person overcompensating for looking like Jaws.

I know a Guy can’t help it if he has to wear braces. It’s just difficult not to hold it against someone when everything about him makes you want to leave Wisconsin.

Despite his obnoxious behavior I felt sorry for him. He smiled a lot. I doubt he went on dates often.

By the time Jaws said he wanted to feel me inside of him, I had already reached that unrecoverable stage of self loathing. Titanic’s bow had already gone under so to speak.

God knows why I take the pity route so often. If you have sex with someone out of pity, you inevitably end up feeling sorry for yourself. Actually, it’s not just sex. The pity had taken control over me the moment I agreed to go to Taco Bell on a first date.

And it never ends up well for the Guys I pity either: Because of the sex Guy #50 was under the impression I liked him. However I always follow up pity sex by turning into a ghost. I stop sending emails, text messages or apps. I make myself an unperson to those I pitysex, while they in turn always think of me as relationship material.

I suck at rejecting people.

So instead of rejecting Guy #50 before the sex, I rejected him after, hurting him more than I would had I simply told him he looked like Jaws before he suggested tacos for dinner.

Guess I’m not as good at talking as I thought I was.

Relationship summary:

LENGTH: 4 hours + plus an eternity at Taco Bell
FORMAT: Dinner at Taco Bell followed by pity sex
SEX SCORE (0 = Jaws and glory holes <–> 10 = The best sex ever): 2.5

Guy #48 – Summertime sadness…

Dear Guy #48,

Are you still alive?

I can’t find you on Facebook, Twitter, Instagram or even Myspace. If you died I would never know.

Our lives only intersected once. It was on September 18^th, 2009, my last night in Toronto.

Our date was heavily anticipated. In the weeks leading up to it we had exchanged messages of ever increasing length and depth. Often Guys on Craigslist speak in abbreviations (e.g. m4m, vers/top, no ff, 33, 6in cut, 6’1’, 160lbs, in2 bdsm, no ws), but the two of us had swapped entire autobiographies. We had even talked over the phone for hours.

Our actual date was one of the best I ever had.

We met up in Downtown Toronto and simply made the city our home for the night. We sat at the harbor front for a long time, staring out over Lake Ontario. We talked. I can’t remember what we talked about exactly. All I do remember is that we talked a lot. It was immensely liberating to have found someone I didn’t have to explain my thoughts to.
At one point we found out we both liked the Pet Shop Boys. It was just one of the many places where we ‘found’ each other.

I knew you were someone I could be with. In fact, I felt very much at home in your presence. It wasn’t the kind of bond I ever expected to find with a Guy.

Two and a half years before our date, I had left my home. Since then I had grown from being a shy bicurious recluse to a sexually confident predator in a city full of prey. Now I had finally found a sense of home the night before I had to fly back to it.

Our date ended on the backseat of a cab. I don’t know about you, but to me it was the best cab ride ever. We kept our clothes on, but apart from that the cab driver had access to free porn whenever he looked in his rearview mirror. We didn’t care.

The plus side of riding a cab at night is that cab drivers are probably used to people making out on their backseats. The downside is that cabs drive fast when there’s no traffic to make the moment linger.

Our ten minute taxi adventure would be the only occasion we ever consumed our feelings for each other. We consumed them like rabbits, but even animals can only go so far inside a taxi cab before they get arrested. In that sense our relationship got stuck in foreplay. Kiss me hard before you go…

Things didn’t end after we said goodbye. The lengthy emails and phone calls continued for a while.

Of course, distance is often a deciding factor in the battle between longing and ease. I would go on to meet other Guys, closer to home.

…whatever home was the first few months after our date. You made me feel at home in the backseat of a taxi.

Had I stayed in Toronto we probably would have gotten to know each other much better and more intimately. Instead our relationship slowly dissolved like smoke after an explosion.

In what would become your last email to me you told me you were suffering from severe depression. It was almost a year after our date. Depression had always been one of your main adversaries.

I realize it sounds weird, but I sincerely hope you didn’t kill yourself. Whenever I think of you, that’s my first thought: Hopefully Guy #48 is still alive.

One of the things I liked about you was that you didn’t let yourself get caught up in social media as we’ve come to know it.

It also means I have no way of knowing how bad your depression really was. We had a very strong human connection, but not a digital one.

I hope you managed to overcome the sadness.

Kiss me hard before you go
Summertime sadness
I just wanted you to know
That baby, you’re the best

Relationship summary:

LENGTH: 6 hours (not counting three weeks of anticipatory emails and phone calls)
FORMAT: Date
SEX SCORE (0 = The obligatory economy class baby that cries throughout long flights <–> 10 = The best sex ever): 9

Connection

Guy #46 – The massage…

A good massage is quite literally like a trip to heaven, a place of infinite bliss and carelessness.
A good massage makes you forget about your worries and your imperfections.
I could probably enjoy a plane crash if someone gave me a good backrub all the way down.

If I ever strike up a serious relationship with a Guy, I would like for him to be good at giving massages. It would make loving him considerably easier.

For a long time I denied myself the pleasure of getting massages. I was too self conscious.

Here’s why:

As you can see I drew a little circle on my back. It marks the spot where my T-shirt bulges slightly.

For the first 27 years of my life I had this strange little growth on my back. It was about the size of a pea. Although small compared to the rest of my body I resented it. It made me feel unattractive whenever a Guy was within visual range of my useless mutation.

Many times I tried cutting it off with a peeler. Operating on my own back in front of a mirror with a kitchen knife is not exactly Nobel Prize material. For starters I never bothered to think of sedation. I got my back to bleed this one time, but my growth remained. It had literally made its home on the one place my arms couldn’t reach.

So massages were never really my thing, knowing it would reveal my pea for the world to see.

Guy #46 insisted however.

Guy #46 understood that sex is infinitely more pleasurable when there’s personality involved. So although the format of our date was well established in advance, we did have a very good time getting to know each other, making ourselves comfortable and learning to embrace each other’s energy.

I was already completely at ease by the time Guy #46 pulled off my shirt and started to massage me. Before I could turn around to hide my cubic centimeter of bodily shame he said: ‘Oh look, you have a little thing there. How cute!’

It took me a few moments to absorb that. In my opinion Guy #46 was saying something like Oh, you listen to ‘N Sync. You have such good taste in music!
I explained how I had come to dislike my little growth, but Guy #46 maintained it didn’t bother him at all.

As luck would have it I was already in a fairly deep stage of relaxation when Guy #46 complimented me on my imperfection. Added to that he was good at giving massages.

For the first time in my life I surrendered my body completely, pea and all.

I’m sure the sex we had afterward was phenomenal. I don’t remember much of it. Me and my consciousness had drifted to another dimension. I don’t even remember what we did exactly. All I do remember is the feeling of letting go.

I think it was the feeling I had been chasing since Guy #1.

Guy #46 and I ended up having two dates. I got rubbed to heaven and back both times. I would have gone back for more, were it not for the fact I was weeks away from moving back to my home country.

As for my inoperable little stump, I had my doctor remove it about half a year later. He laughed when I told him I had tried to operate on myself.

I’m glad the doctor found a cure for my mutation, but strangely enough I never enjoyed a massage as much as I did those nights with Guy #46. Maybe he was that good.

Or maybe I’ve gotten used to letting go since then.

Relationship summary:

LENGTH: 2 x 2 hours
FORMAT: Sex dates
SEX SCORE (0 = Operating on yourself with a peeler <–> 10 = The best sex ever): 9.2

Guy #39 – The lie that was his selfie…

Selfies can be deceptive.

I’ve come across internet profiles from men that go by one and the same picture for years at an end. It’s because they only have that one picture in which they look good. I don’t trust profiles with only one picture.

Guy #39 taught me.

Guy #39 looked good in his selfie. I thought it would be greedy of me to ask for more pictures of him looking horny, but I now know my greed had motivated me to go on this date in the first place. I should have listened to my greed as one does on sex dates.

On the other hand I ended up liking the fact Guy #39 had deceived me into getting to know him.

We clicked. I found myself very comfortable with him. We laughed a lot.

We both knew his selfie was ten years old and heavily photoshopped. But it was okay. Lying is often part of a sex date.
In the end Guy #39 even told me he wished he was hot like he used to be. I guess that was his way of saying sorry for the lie that was his selfie.

Selfies are good for making us feel like we look good. I think I made Guy #39 feel he looked like his selfie again.

I was approaching 30 when I first started photoshopping myself. I was amazed by what the contrast button could do to my abs.

Though I’m hardly ever on dating sites these days I do update them every so often with my latest pictures of me looking bored into a mirror, holding up a phone, wearing a towel. It’s my way of letting people know I’m not a person with only one good picture.

Over the years my selfies have become increasingly beautiful. And increasingly deceptive. And as I grow older, I will stop uploading selfies every so often. If I stay single I might end up being a guy with only one selfie.

I wonder what my life would have been like had I come out sooner. I enjoyed the gay scene very much, but at times I wish hadn’t spent the first 24 years of my life being so afraid of it.

Then I might have met Guy #39 around the time his selfie was taken.

Relationship summary:

LENGTH: 2 hours
FORMAT: Sex date
SEX SCORE (0 = That one mosquito circling around your head when you’re trying to sleep <–> 10 = The best sex ever): 8.3

Guy #36 – Pain relief…

Guys #20 through #48 all guest starred in my life in the summer of 2009, when I spent three months in Toronto. Whatever I had going with Guys #20 to #48, each and every ‘relationship’ had an expiry date.

A very big part of me resented the fact I was to leave the city soon. It’s not so much the abundance of sex I would miss. It’s that I met some people that could have been good friends or maybe even more than that.

Guy #36 felt like a very good friend for one night.

Sex dates are actually a great way to meet people. Sure, sometimes they have the formality of a job interview, but for every person that leaves you feeling empty inside there’s another one that makes you feel alive, valuable and even loved.

Guy #36 came to my place and had sex with me. It was awesome. Our sexualities were a near perfect match.

The sex didn’t last very long. Things went from awesome to modestly spectacular after the sex, when Guy #36 and I started talking.

We ended up really connecting with each other.

Guy #36 told me he had been in a car accident this one time. He said he didn’t know what pain was until that moment. His body was still recovering from it. Pain was a near constant for him.

It’s probably why the sex had been so good. It was his pain relief. I always thought of physiotherapists as masseurs with less sex appeal, but Guy #36 told me physiotherapy can be a living hell. Sex must have been like morphine to him.

When I told Guy #36 I would be flying back to my home country soon he seemed genuinely disappointed, but neither one of us saw any use forcing a clumsy transatlantic friendship just because we digged each other. We were fine with this being a one-time pain relief.

Sometimes it can be strangely wonderful to cuddle up with a complete stranger you met on the internet. Someone who’s been through a lot of pain.

I don’t miss Guy #36. I do miss Toronto because of guys like him.
And I really hope his pain is gone.

Relationship summary:

LENGTH: 3 hours
FORMAT: Intimate sex date with pain relief
SEX SCORE (0 = Lying to your parents <–> 10 = The best sex ever): 9.2

Guy #35 – The virgin…

When I first met Guy #35 I assumed I meant a lot to him.

I was his first time with a guy.

I knew it’s never wise to have sex out of empathy, but I really felt I could give something to another human being. I had grown so comfortable with my own sexuality I considered it a gift to people. Or maybe I just felt sexually at ease in the presence of a virgin taking his first step out of the closet.

Guy #35 and I met in Toronto, but he took me to his home halfway to Niagara Falls. I enjoyed the train ride, also because it allowed me to take a nap. I hardly ever get a chance to do that on a first date.

Toward the end of our journey I woke up and initiated a conversation. Having a background in psychology however makes me inclined to ask intimate questions to total strangers without giving it a second’s thought. Whenever I’m with someone I want to get to know that someone, even on a sex date.

I got the impression Guy #35 liked me better when I was asleep. He clearly didn’t want to answer my questions about how lonely the closet can get when you’re the bearer of so many secrets or if he even enjoyed being gay.

I was going to have sex with Guy #35 out of empathy, so that’s what I gave him. I thought that’s what he needed, considering what my first time with a guy had been like.

The majority of my waking moments I spent comforting Guy #35, telling him he didn’t need to be nervous, that I wouldn’t force him to do anything he didn’t want to or how brave he was for making this step.

When we ended up at his place Guy #35 went straight to business. It’s common courtesy on sex dates to offer your guest a glass of water, but I was guided straight to a bed where we had sex. He was good.

He was good because he knew what he was doing.

The bastard.

I found my first guy through a dating service. It didn’t strike me as odd I could meet someone who was going through the exact same thing I had gone through. It never occurred to me people might advertize themselves as a virgin to up their market value. It had worked for me. Guy #35’s virginity was nothing but a marketing tactic and I had fallen for it.

I believe Guy #35 was more experienced than I was.

Karma did its work though:

My empathy gave me a nice nap and unexpected pleasant sex.
He got to have sex based on a lie, but he paid by having to live it. He must have had many guys before me. I was probably the only one that started acting like his therapist, asking him if he was okay with all the lies.

I was asking the right questions without even knowing it.

Bet that was a first for Guy #35.

Relationship summary:

LENGTH: 2 hours
FORMAT: 1:45 hours of unsollicited therapy, 15 minutes of sex
SEX SCORE (0 = When Dick Cheney shoots you in the face <–> 10 = The best sex ever): 8.2

Guy #28 – Parking lot purgatory…

Nothing is quite as depressing as sex in a car on a parking lot in broad daylight.

First of all, most cars are not designed to have sex in. They’re an ergonomic disaster when it comes to intertwining your body with that of someone else. Second, I was constantly on the lookout for people who might see me, along with Guy #28’s head appearing in and out of view over my dashboard.

My date with Guy #28 was a complete disaster.

They say size doesn’t matter. Well, this guy’s penis was pretty much the complete absence of matter. It was tiny. When he unzipped his pants I was greeted by something best described as a socially phobic shrimp.

I found myself on a date with an Asian stereotype:

Guy #28 was completely submissive. That much became clear the moment I stepped into his car on what would be our first and only encounter.
“Hi, how are you doing? You look super! I’m so glad you could make it,” he said as if I was a long lost friend.
My first thought of him was that he didn’t look at all like the guy from the picture, although from a certain angle I could see how he had gone about Photoshopping himself.
He was good with computers.

When we drove off I assumed we were going to his place. After a while he told me he still lives with his parents. He wasn’t driving to his place. He was just driving. He asked if I knew of a place to go. I didn’t.

Our love nest would become a parking lot. In broad daylight.

I wasn’t proud of myself for having sex on a parking lot in broad daylight. It’s not that we got caught or that I never did it again, but the size of Guy #28’s penis made me realize how my ruthless pursuit of sex had sunk my standards. It was ridiculous of me to agree to sex on a parking lot with someone I wasn’t comfortable sharing a space with.

To make things worse Guy #28 was unbelievably passionate. He acted as if we were lovers, while in reality we were just two guys with nothing in common except their time on Craigslist. I couldn’t stand Guy #28’s drama.

I came quickly. I had trouble thinking happy thoughts when I did, but I figured it would be the quickest way to end this ordeal.

At first I was relieved the sex was over. Then Guy #28 asked if I wanted to go have coffee with him. It should be noted it’s not customary to go for coffee after anonymous hook-ups on a parking lot.
I really wanted my date to drop me off at my subway station, but he was already parking his car in front of Starbucks when he dropped the question.

Being with Guy #28 must be what purgatory is like.

All I wanted was to be released from my date, who kept on saying how super happy he was to have met me and how he really wanted to be my friend.
The parking lot sex had evaporated his initial shyness. Now he was constantly telling me how super I was.

Then came the moment Guy #28 ran into two of his girlfriends. I’m not entirely sure their sudden appearance was a coincidence: Guy #28 stopped sending messages on his phone the moment his hags entered the scene. Guy #28 couldn’t believe his luck he was surrounded by so much people to not feel lonely with.

I was loathing myself however. I had to make small talk with the friends of someone who had just given me a blowjob in his car.

I felt like hitting Guy #28 when he ordered himself a second latte. I wanted to go back home, away from my date’s desperate attempts at having company.

I socially obligated my way through Guy #28’s friends for a good half hour. His clinginess became increasingly annoying. At times I got the impression he was pretending to be my boyfriend.

When we finally ended up back in his car we went to another parking lot, this one belonging to my subway haven. I nodded Guy #28 goodbye the moment we got there. He asked if I was going to call him. I told him I would think about that. He said it was making him so sad I had to go. I told him he would get over it.

As I grabbed the door handle Guy #28 put his arms around me and started to cry.
“Please don’t go. I like you so much,” he cried. I told him he had just given me a blowjob on a parking lot and that it was to be the extent of our relationship.

He cried over my impending absence the way North Koreans cry over the death of a Supreme Leader. It was unbearably awkward. In the end I had to pull myself out of Guy #28’s arms. I left him crying in his car.

I’m not saying sex dates are a bad thing, but I do find it interesting you often encounter a lot of loneliness on a sex date.

For what it’s worth Guy #28 has my sympathy. But when your penis is that small and you are incredibly needy, dependent and insecure, it might not be wise to find love in random strangers on a parking lot. In a way I may have taught him that by slamming the door in his crying face.

For his sake I’d like the world to be a place where penis size is irrelevant, but that’s not the case. Stats are an important part of our culture. As is Photoshop. Or parking lots for that matter.

Or post-orgasmic self loathing.

But maybe that’s just me.

Relationship summary:

LENGTH: 2 hours
FORMAT: 10 minute drive, 5 minute blowjob, 90 minute latte, 15 minute farewell
SEX SCORE (0 = Room 101 <–> 10 = The best sex ever): 0.5

Guy #27 – Recreationship…

Sex is a bit like drugs.

If you know how to use drugs wisely, a lot of them can be fun.

Sex is the one drug we should embrace as a society. It is pretty well established that the more people smoke weed, the less people get upset about it. It’s the same with sex.

So while we shouldn’t get high 24/7, on the special occasion you do the best idea is to simply enjoy it as much as you can.

This was my mindset the night I met Guy #27.

His opening line was Do you know that you are very beautiful? It was in that moment I decided I was going to enjoy him as much as I could.

We talked a little over very loud music. I’m not a fan of extremely loud club music, but I do like how it forces you to be in each other’s space when you’re talking. It makes the whole seduction ritual flow ever so smoothly. The noise causes proximity. The proximity causes touching. The touching causes even more touching. All the touching causes kissing and not long after that Guy #27 and I were gorging on each other like a pair of toothless zombies.

We didn’t just kiss. We ate each other.

I was in a big city in a shady night club celebrating my own sexuality. I was fully aware of the fact there were people mere feet away from us, staring at us in silent disbelief over how Guy #27 and I were going at each other.

When you have sex it’s nice not to care about what the rest of the world thinks of it.

Naturally I ended up at Guy #27’s place, a beautiful Downtown apartment overlooking the city skyline. I was living a dream.

The great thing about careless sex is that it allows you to open up to someone. Guy #27 and I got to know each other quite well over the few months we dated. In some ways we had a little bit of a relationship-thing going on. We went out for dinner together. We ate breakfast together. We would talk together. We would be together.

A big city becomes so much more of an experience when you have someone to share it with.

Sexwise, the gorging stopped after our first date. The sex between us became increasingly satisfying, but neither one of us was being greedy about it anymore.

I guess you could say Guy #27 and I were both very good recreational drug users. You might argue the two of us were having a recreationship. I enjoyed being with Guy #27 the way I enjoyed a good massage or a nice dinner. Or drugs.

Guy #27 had made his home in the city we enjoyed together. To me this city was merely a stopover. Our recreationship was never meant to last.
The two of us recently got back in touch though. It’s a nice feeling when someone welcomes you back into their life after having been absent from it for years.
Guy #27 told me he has fond memories of the time we shared together. He also said he had enjoyed the sex, but that he has since gotten better at it.

I told him the same goes for me.

Relationship summary:

LENGTH: ± 2 months
FORMAT: Recreationship
SEX SCORE (0 = Club music at a funeral <–> 10 = The best sex ever): 8.8