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.

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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 #23 – Chubby, bearded and oh so sweet…

 

 


 

 

Your sex life is a bit like a box of chocolates. You never know which one you’re gonna get. But you do know you want more, because chocolate just so happens to be addictive like nicotine.

Or maybe that’s just me.

Personally, I like experience in the broadest sense of the word. So whenever I have one piece of chocolate, I crave for more.

I spent the summer of 2009 in Toronto, Canada, the biggest box of chocolates I had ever seen. I wanted to use my time there to explore as much of my sexuality as humanly possible. Maybe it was greed, maybe it was lust, desire, curiosity, unresolved mother issues or all of the above, but for me the time had come to cross another boundary.

At 27 years of age I was still young. I feel prettier now than I did back then, but my reasoning at the time was that my beauty had already peaked. If I wanted to explore my own sexuality, the time was now, or so I figured.

So I auditioned for gay porn.

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Like many gay guys, I enjoy watching gay porn from time to time. As such, I’ve come to appreciate the efforts of gay porn stars, exposing their own sexuality for the world to see and admire. I reasoned that doing gay porn would be a nice way to ‘give’ something to the gay community, while at the same time using my own sexuality as an instrument of sorts. I enjoyed the thought of being in control of my sexuality.

For years at an end, my sexuality had been tied down, suppressed by a heterosexual dream I had chased for way too long. Now that I had finally and definitively shed myself of all the restraints I came to know and hate over the years I was ready to live.

To live.

So I auditioned for gay porn.

How does one audition for gay porn?

Well, one goes on Craigslist.

The rest pretty much came naturally. I responded to an ad asking for gay porn models by emailing a few selfies. I then received a phone call from someone asking me if I was absolutely sure I wanted my naked self on the internet for the entire duration of human civilization. After agreeing to that term I was invited to audition.

Technically speaking, Guy #23 and I never had sex. He never even touched me, not in a sexual way at least. Guy #23 was a producer and director of gay porn videos. I first met him in his apartment, where I had come to audition.

So how does one actually audition for gay porn?

Well, one unzips his pants and shows a porn producer one can obtain and maintain an erection in the absence of any sexual arousal.

I passed the test.

In fact, I passed all three tests. Guy #23 explained to me porn is about three things: Personality, looks and dick size. He mentioned them in that order, and rightfully so I might add.

During my audition, a friend and colleague of Guy #23 dropped by for a visit. I believe I wasn’t wearing everything when he came in. He modestly complimented what he was seeing and introduced himself as casually as if we had met on a company picnic. He would later tell me he spent his free time counseling people with HIV. It made me feel good I was going to do porn with people that were anything but heartless.

Guy #23 and I would become friends. He introduced me to stuff gays can do in big cities. I had never heard of the concept of a gay sauna until Guy #23 took me there one evening. And while Guy #23 and I never did anything sexual together, he was there during some of my most intimate moments. I had definitely crossed a boundary with him, but mostly it was nice having a chubby bearded French Canadian as a friend.

I once asked him if he liked his job. He had made hundreds of videos before me. I wondered how something like that would affect my own sex life. I always intended for porn to be a part of my sex life, not a part of my resume.
“I get jaded sometimes,” Guy #23 said.

I’d like to think he wasn’t jaded when he was working with me.

 


 

Relationship summary:

LENGTH: 3 months
FORMAT: Professional friendship
SEX SCORE: N/A

Guy #22 – My looks matter too…

 

 


 

 

It can’t be denied some of the guys you find on Craigslist are hot.

Guy #22 was one of those guys.

In fact, he was the hottest guy I had ever been with up till then. And I was already at a point where that meant something.

At first I considered myself lucky. What could possibly go wrong in the presence of sheer beauty?

Well, for starters it didn’t take me long to realize Guy #22 was hotter than I was. I couldn’t help but feel sorry he had to settle for me. I felt unworthy of the sex he agreed upon.

The sex was actually modestly spectacular, for me at least. I’m not sure if Guy #22 was having any fun. I don’t think he enjoyed me as much as I him.

As we were busy performing numerous pleasures on each other’s bodies I found myself constantly in awe of the body I was performing them on. I felt sorry for my own body in return. Guy #22 must have felt my inferiority. Even if he did find me attractive, my own shame must have masked most of what I had to offer.

We followed up the sex with a shower. Again, I was uncomfortable rubbing soap on something I considered too good to be mine. I literally didn’t know how to rub things the right way.

A few days after our 45 minute encounter I talked to Guy #22 on MSN, which people still used back then. I asked if he wanted us to meet up a second time.
‘Not really,’ he said. I was flattered by his honesty, but disappointed at the same time. I wondered if I would ever get another chance to be wanted by so much beauty again. Then again, I was never that wanted. I was granted, at best.

People with good therapists tend to believe looks don’t matter. I have a MSc. in Psychology and I think looks do matter. So either I’m a lousy therapist or looks are an important part of who we become in life. That’s not an ideology. It’s an observation.

Yet I also observed how looks are fluid, how they are mostly an extension of how you feel about yourself. I believe everybody looks as attractive as they feel.

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Had I felt more attractive in the presence of Guy #22, he might have wanted me a second time. Still, him granting me access to his beauty made me feel more beautiful. I know, our personalities hardly played a role. At the time I was still caught up in discovering my own personality and lacked the mental capacity to really dive into the minds of people I met through Craigslist.

Had I met Guy #22 today I probably would have tried to get to know him. I would have allowed him to know me. And then the sex might have been really spectacular, and plentiful.
We could have granted each other much more than we did.

I wasted Guy #22 and quite a few hotties after him, simply by referring to them as hotties. Whenever I consider a guy a hottie it’s an expression of insecurities about my own looks. Those insecurities prevented a lot of pleasant sex from becoming phenomenal sex.

Whenever I think back about guys like Guy #22, I often wish I could see them again. I would love to have a conversation with Guy #22, find out what makes him tick.

Then again, his Craigslist ad at the time specifically stated he was an ‘athletic top in search of NSA fun’. He never wanted our relationship to last more than an hour.

Guys often make it difficult to find love in each other.
We’re like people that way.

 


 

 

Relationship summary:

LENGTH: 45 minutes
FORMAT: Sex date
SEX SCORE: (0 = Having ‘the Talk’ with your parents <–> 10 = The best sex ever): 8.2

Guy #21 – Looks matter…

 

 


 

 

There’s a big difference between a body and a face.

A body can be shaped. A human being can survive on blueberries, bananas, rice and oatmeal. Really, if you don’t mind bidding farewell to pasta and cramming out a hundred sit-ups every day, getting a nice body isn’t that big of an achievement.

A face however is pretty static. No amount of gym hours can change the way you look with your clothes on.

Of course, impulsive little me found that out the hard way.

You can guess where this is going.

Guy #21 had a gorgeous body. By the looks of his abs pasta was poison to him. I would have been attracted to him, were it not for the fact that his face appeared to have been drawn by Picasso.

Our paths had crossed on Craigslist, where his faceless body pic was somehow hot enough to make me want to see him. Heaven knows what the hell I was thinking.

I felt sorry for Guy #21. I’d like to believe we live in a world where everybody is equally beautiful on the outside, but the sad reality is that some people are objectively unattractive. Guy #21 probably read the disappointment in my eyes when we first met. I’m sure it was a look he had seen on other faces, perhaps even his own every time he passed a mirror.

Having been a virgin for the first 24 years of my life, I know what it’s like to go through life feeling ugly. For a long time I probably was unattractive. That’s the kind of energy I radiated. It’s the kind of energy Guy #21 radiated.

I had sex with him out of empathy.
It wasn’t great.

Yet it wasn’t awful either. And not just because of his abs. Guy #21 had a warm and loving personality, especially by Craigslist standards. And even though Craigslist was swarming with guys looking for quick fixes, it was obvious Guy #21 was looking for a connection, a bond with someone, something meaningful, however superficial.

Actually, over the years I’ve come to experience there’s no such thing as superficial sex. I just wasn’t aware of that during my date with Guy #21. Had I known Craigslist cashes in on our desire to be loved, I might have summoned up the honesty to tell him he wasn’t my type. I might have told him he should work on believing in his beauty instead of doing sit-ups to increase his sense of self worth.

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A face may be static, but a brain isn’t. It took me 168 guys to appreciate how much my brain determines the way I look, 168 and counting.

I hope Guy #21 grew up to be as attractive as I am now.

 

 


 

 

Relationship summary:

LENGTH: Two hours
FORMAT: Sex date
SEX SCORE: (0 = “I did not hit her. It’s not true. It’s bullshit. I did not hit her. I did not. Oh, hi Mark.” <–> 10 = The best sex ever): 6

Guy #20 – Going supernova…

 

 


 

 

Guy #20 marked the first time I ever had sex in Canada. Toronto, to be precise.

All of my previous sexual experiences had taken place either in the closet or in a small country with only one gay club. Now I had arrived in a city big enough to have its very own gay village.

I spent the summer of 2009 in and around Downtown T.O., enjoying the thought of constantly being surrounded by millions, many of whom were gay guys.

It was a time of many firsts. Sexually speaking, I went supernova that summer.

For starters, the summer of 2009 introduced me to the world of Craigslist, where gay men gathered before the rise of Grindr:

“NSA blow”
“Looking for chubby bottoms”
“Reward for your dirt”
“Fun in your hotel room”
“Dad, I need a punishment”
Those were the kind of advertisements I shifted through in search of my Guy #20, who I first came to know as “Athletic Hot Bi Guy”.

Athletic Hot Bi Guy and I got in touch through Craigslist. We exchanged a few pictures, decided we were both doable and then set up a date at his place, a beautiful penthouse in Downtown Toronto overlooking the city skyline. The scenery might actually have been prettier than Guy #20 himself.

My first ever Craigslist date went like clockwork up until the moment I suddenly had to puke. And again. And again. And then once more. And a few more times after that. I lost count eventually.

I had never heard of roofies, or that people sometimes put roofies in other people’s drinks. I do remember thinking my wine had tasted funny that night.

It wasn’t until years after my date with Guy #20 that I finally realized he had pimped up my drink. At the time I figured I had drunk too much, even though one glass of alcohol had never made me sick before.

Apart from feeling unbelievably dizzy, weak and sick, I was very much ashamed of myself. No one likes to puke on a sex date. I was so busy being ashamed of constantly hovering my head above a toilet, I neglected to fully realize how calmly Guy #20 was taking all of it. He didn’t comfort me, nor did he get in any way upset or worried. He just kept sitting on his bed, athletic and hot, waiting for me to feel better.

Of course Guy #20 knew exactly what was going on. He was probably counting himself lucky I didn’t realize I had been such a good bottom because of a roofie.

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Naturally, I wish it upon Guy #20 to end up in the Emergency Room with a vacuum cleaner stuck to his parts. The sad thing is he never even needed drugs to get me. Athletic Hot Bi Guy summed him up nicely. He was athletic and hot. That’s usually enough to get me high.

To my surprise, Guy #20 later contacted me to invite me a second time. At the time it highly surprised me all my puking hadn’t been a turn-off, but I guess in his mind it was a fair price for such a good bottom.
I however didn’t feel like being reminded of my shame, so I kindly ignored Guy #20’s invitation.

So, my first sexual experience in a big city ended in a modest drug overdose. Yet at the time I wasn’t aware of that. What impressed me most was how unworldly easy it was to obtain sex in a populated area. To me, Guy #20 marked the beginning of a new era: I had definitively left behind this shy, insecure and dorky figure who couldn’t get a girlfriend. That had been me, barely two years before.

After spending the night at Guy #20’s house, recuperating from what I still thought was bad alcohol, I walked down the streets of Toronto, feeling content and satisfied.

I knew I had a busy summer ahead of me.

 


 

Relationship summary:

LENGTH: One night
FORMAT: Sex date
SEX SCORE (0 = Windows Vista <–> 10 = The best sex ever): 6.5