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Promiscuous Gay Nerd: What Makes Sex Good?

, by Jake Sobo

PGNerd2Last year during a visit to San Francisco over New Year’s, I witnessed something truly remarkable. My friend gathered a handful of gays together, poured some freshly brewed tea, and gave an hour-long PowerPoint presentation about the sex he had during the previous 12 months. I’ve seen a lot when it comes to sex. But I’d never before witnessed such a public display of sexual reflexivity. We went through the highlights. We ruminated about what made for a good sexual encounter, and why some were lackluster. It was an educational exercise in perversion that was, truly, exhilarating.

I left his apartment, came back to my friend’s apartment where I was staying, and opened Microsoft Excel. I saved a blank workbook titled “Tricks.xls.” (Nerd alert!) This column is the product of tracking the sex that I’ve been having for the past ten months. People have for years asked me questions about my sex life—How much? How often? How good?—and I really had no way to answer most of them with any precision. I estimate that, in my lifetime, I’ve had sex of some kind with somewhere between 500 and 2,000 guys. That’s a pretty huge range. I wouldn’t be surprised if it were at the high or low end of it because I simply don’t keep track.

It turns out there are benefits to keeping track. When I began this experiment, it was largely out of a desire to know more. I was curious. What makes me tick? I knew the basics, obviously: I generally prefer to get fucked. I like guys with big dicks. And because I live in a college town, I tend to wind up fucking guys a few years younger than me. But what exactly made for good sex? Are there qualities associated with good encounters that I could home in on and better seek out in future partners? And conversely, are there qualities I should steer clear of?

The answer is a resounding yes, and quite frankly, analyzing the data stunned me. But before I get into the analysis, I need to make one thing clear: This is a project about my sex life. What turns me on. What gets me off. It isn’t about your sex life—though I’d love for you to write a comparative analysis. If you created a sex diary, you’d value different things. On a spreadsheet, you’d create different columns. You’d even be likely to have had very different encounters with the exact same guys I reference. This exercise isn’t about creating a universal theory of good sex, or suggesting that everyone follow my lead. It’s about trying to start a dialogue on what makes sex great.

Because let’s face it, for a lot of gay men and plenty of others, sex is a core part of our lives. Shouldn’t we be having the best sex possible? And given the 21st-century tools at our disposal—PrEP, treatment as prevention, seroadaptation, and condoms—there are now more ways than ever to keep ourselves and our partners healthy while we’re at it.

Without further ado, I present to you my spreadsheet. It’s a Google doc. Go on, click on it. Take a look. Absorb all the work I’ve put into it the past ten months.

Let me go over a few basic things. First, I’ve changed all the names. Matthew isn’t really named Matthew, but he is 34 years old according to his profile. I’ve also anonymized the city names. Entries are ordered by date, but each partner is assigned a unique number. Repeats are numbered as 14.1, 14.2, etc., and colored green. Guys with ratings of 9 or higher are colored red. Overnights are colored purple. And that one orange bar represents an “STI event”—the time I got syphilis in March. Boo.

For each encounter, I record the venue through which I met the guy and the city in which I met him; his age, dick size, race, and HIV-status; whether we had oral or anal sex, or, because I’m a fan, whether there was rimming involved; whether we used condoms and whether that was pre-arranged or not; whether we used any drugs or intoxicating substances, including alcohol; and the number of orgasms we each had. Then I assign each encounter a subjective score from 1 to 10 (1 being the worst sex ever; 10 being the best sex ever). I also add a series of comments that have proven the most interesting for me to look back on in this analysis.

Sex by the Numbers

Let’s start with the easy stuff: the numbers. Are certain factors associated with higher overall scores? This isn’t a statistical analysis, by any means. But with 50 encounters with 43 unique partners, I figure there is some kernel of truth in the numbers. At the bottom of the spreadsheet, you’ll see I’ve divvied up the average quality scores by a variety of factors. Of course, some have too few people in them to be meaningful (e.g., the city comparison and some of the race categories). Other categories line up exactly where I expect them to be (e.g., dick size).

But let’s check out condoms. I expected higher scores to be associated with sex without condoms. I just intuitively figured that this would be the case. I don’t like condoms; they can lead to chafing and painful sex. And god knows how many guys lose their erections repeatedly with them, which is an unending frustration for a bottom in need. All these reasons informed my choice to start using PrEP almost exactly a year ago. While I only used condoms four times over the past nine months, at the very least this didn’t necessitate having a horrible time. In fact, the average score for sex with condoms was a bit higher than the average for sex without them. Indeed, I gave a score of 9 or higher to two of the four encounters that involved condoms. While I recognize that this subjective scoring is confounded by god knows how many unnamed factors, this still surprised me.

That said, what does seem to make a difference (albeit a slight one) is whether or not that condom use was planned. I quickly got the sense this year that planning sex without condoms requires breaking a code of silence that makes many gay men uncomfortable. I think part of what makes condomless sex hot is its reputation as a passionate, “in the moment” practice that people associate with less personal responsibility. In many guys’ minds, fucking without condoms with a hot guy in the heat of the moment is sexy, whereas planning ahead of time to fuck without condoms is gross and reckless. I think this is reflected in the data: I rated the sex I had without planning ahead to use or not use condoms higher than when we agreed to use or not use condoms ahead of time. Of course, this pattern is largely made possible by PrEP. With PrEP at my side, I feel comfortable leaving the decision to use condoms in my partner’s hands.

Let’s also take a look at drugs and substance use. As you’ll see from the spreadsheet, I’m a fan of poppers. I understand they’re not for everyone, and there are important things health-wise that you’ll want to pay attention to if you use them (e.g., dangerous interactions with erectile dysfunction meds). That disclaimer aside, although they appear fairly frequently in the “Drugs/Etc.” column as you can clearly see, popper use is not necessarily associated with better sex for me. In fact, I suspect that poppers get a bum rap here because I sometimes use them as a crutch for bad sex. Lesson learned: For me, poppers can make great sex even more amazing, but they can’t make bad sex better.

The figures for alcohol were even more surprising for me. I don’t tend to think of myself as a fan of drunk sex. In fact, I regularly disparage the idea. But the numbers seem to tell a different story. What’s going on here? Well, I’ll get to this more in the next section, but many of these encounters involved guys I met up with for a drink before we had sex. In many cases, this time together socializing helped develop a chemistry that translated into better sex. Alcohol plays a role here in helping us cozy up to each other, but it’s also just a product of spending time together socializing before fucking.

The More Complicated Stuff: Sex and Intimacy

All this talk about socializing leads me to the more complicated stuff—the comments section! Beyond just sheer numbers, how is good sex described? Experienced? What do I complain about after bad sex? The consistency truly shocked me. I describe bad sex as “mechanical” and “disconnected.” My brief synopsis of my encounter with Matthew (#1), is a perfect example. “Very hot guy—but not into kissing. Disconnected sex. Disappointing.” Matthew was fucking gorgeous. I mean, this man could have been a model. Sculpted body. Cheekbones for days. But damned if he wasn’t about as interesting as a chemistry lecture in bed.

Bad kissing is definitely a theme in the bad encounters. Take a look at Nolberto (#5): “Bad kisser.…Nice guy, but terrible in bed. I couldn’t even get hard. He tried to fuck me, failed. He jerked off and came. I didn’t cum.” I’ve always known kissing is important to me for sex. I just about can’t get off without making out. But that becomes beautifully (and amusingly) crystalized in these reviews.

But what does this tell me? Well, there’s a big fat theme here for me. A lesson I wasn’t prepared to learn. While bad sex for me is “disconnected,” good sex is “intimate,” “passionate,” and oftentimes involves sleepovers and morning sex. Let’s take a look at Jacob (#16), which was probably one of the most powerful sexual experiences I’ve ever had:

Jacob, oh Jacob. Hallowed be thy name. The best sex I’ve had in years—and certainly the first sleepover in years. Probably since my ex. He is so cute, sexy, smart, and an AMAZING lover. Charming. Has a partner. Called an Uber car to take me to his place around 1:30 AM. We fucked for hours. Woke up, fucked again. He came twice inside me at night, then again the next morning. He had a pet tarantula lol. First poz guy to ever cum inside me. I knew immediately he was the one to break that threshold.

There is a lot going on here. Jacob was the first guy I knew was HIV positive to cum inside me. This gave the experience a particular meaning to me. I wrote about struggling with this decision last year, before this experience, when I was still asking undetectable poz guys to pull out. (I won’t rehash the science here: The risk of transmission from an undetectable poz top and a neg bottom on PrEP is exceedingly low). As I was getting out of the shower before I left to meet Jacob, my heart was racing. I was nervous in part because Jacob was blazing hot, but also because in my gut I knew I wasn’t going to ask him to pull out. In the moment, I felt somehow that I was more connected to him. That I was giving him my trust. I know that I do this any time I have sex, but the emotional experience was acutely heightened with Jacob. Beyond HIV, you can see me describing Jacob as a person here. He owns a tarantula. He’s charming. I compare him to my ex-boyfriend.

When I read these and other notes from my best sex this year, the truth just punched me in the gut like a bag of oranges in a mob movie. I’m looking for intimacy. Connection. Guys I can trust and have a conversation with. I’m sure many readers are beyond unimpressed at this realization, but these are the kinds of things you’re not allowed to say you’re looking for when you’re looking for sex on gay hookup websites. You’re supposed to be looking for big dicks. To get your ass pounded. To get fucked in half, goddammit!

Masculinity is written all over these discourses of gay sex, and yet they completely fail to account for what makes sex great in my life. I imagine this might not be true for other guys, but for me, what I’m looking for is painfully clear. While a big dick is a treasure—don’t get me wrong—it’s that intimate connection that truly takes sex from sport to religious experience. It’s almost impossible to describe when it happens, and when it does it can knock you completely off-kilter. I remember one of the first times it ever really happened for me, with a one-night fling a few years back. We had this crazy, intense, and immediate attraction and connection. Somewhere in the fury of the night, he stopped and slowly worked his way down my body, kissing every inch of skin he found. Seemingly out of nowhere, I started crying. It’s not just the action, but the careful, attentive, and caring way he did it. While perhaps not in the sense that most people use the word, it was an act of love. In that moment, I felt loved.

If I’ve learned anything in this ongoing experiment, it’s that I need to pay better attention to myself. To what I need and want. Because I thought I knew why I loved sex so much. It turns out that I was hiding something from myself—keeping myself from acknowledging an uncomfortable truth. Sex can be instrumental, yes, and instrumental sex can be fulfilling in certain ways. But for me, great sex is more than just instrumental. It is a connection between two people that is emotionally charged, vulnerable, and potentially transformative.

What about you? What makes for great sex in your life? As always, leave a comment or send me an email at mylifeonprep@gmail.com.

Jake Sobo is a pen name used for anonymity. Jake has worked in the world of HIV prevention for nearly a decade. He previously published a 19-part series documenting his experiences on pre-exposure prophylaxis (PrEP), “My Life on PrEP,” for Positive Frontiers magazine, which was picked up by Manhunt, translated into French, and widely read in the HIV prevention world. He has spent the better part of his adult life having as much sex as possible while trying to avoid contracting HIV.


8 Responses to Promiscuous Gay Nerd: What Makes Sex Good?

  1. JB says:

    When I started noticing that more and more of my hook-ups were bareback, I did some thinking about that. I came to the conclusion that what I was looking for was intimacy, and bareback sex felt more intimate; something that you do with someone you love and/or trust. Thanks for sharing your experiences Jake, I think there is a lot to be said about gay men and intimacy, and I salute you for adding to that conversation!

  2. Mark S. King says:

    I love that you did this and shared it. This is completely fascinating and shows a lot — maybe even a scary amount — of self awareness. LOL

    Self-actualizing, on the other hand… I would be interested to know how your conclusion about intimacy might shape your future encounters. Does your self-titled promiscuity serve as a barrier to the intimacy you now realize makes good sex?

    43 partners out of 50 might suggest someone avoiding the kind of intimacy your good sex includes. Or you could be a young gay man sowing oats and having fun. Except you’rte not all that young, relatively. Just sayin’.

    We’re all skewed based on our experience. As a “reformed” slut (no judgments there), I’ve found sex with my monogamous partner gets better (who knew?) and I’m actually finding something — gasp! — sexy about only giving it to him.

    So much to digest and consider here. Thanks for your thought provoking shamelessness — in the best sense of the word.


    • Jake Sobo says:

      Hi Mark! Thanks for your feedback.

      I think it’s a question that I’ve been thinking about, and I’m not sure. Clearly, I love having sex with lots of people – that’s not going to change anytime soon. And as you can see, I find great sex with strangers. I’ve had long-term relationships, and the sex I had with my partners was not really necessarily better. Perhaps it was consistently “great” in ways that sex with strangers is not. But I don’t even know if that was true. I had boring sex with boyfriends sometimes, just as I have boring sex with strangers sometimes. Perhaps that’s why all my exes are exes! I look forward to finding a man who can change that.

      In any case, I plan to be a bit more careful about trusting my gut and avoiding guys who clearly aren’t interested in having a conversation or connecting on any level beyond the physical. But let’s face it: when face to face with a 10 inch dick, I’m always going to have trouble sticking to my guns 🙂



  3. Richard says:

    Great blog entry. I have found that some of the most dullest experiences have been with extremely attractive guys. I don’t know what it is about a really hot guy that many times they just suck or are so-so. Maybe they think because they’re hot they don’t have to try? I do agree that an intimate connection can make it all the better. Looking back on some of the most memorable experiences, there was a lot of kissing, talking, and truly enjoying each other in those experiences.

  4. Vic says:

    This just made my weekend, but more realistically my month. I love that you took the time to methodically analyze your sex life. A skill you should probably start peddling to liberal arts colleges as an elective, you being the prof obvs. Intimacy is the key puzzle piece for me as well, a hot quick fuck can be hot and serve its purpose, but if I want to repeat with any guy he must be an intimate lover.

    Good luck sticking to ur guns ;), I also sometimes waver, but only a fool would pass on free water while in the desert.

  5. Brian says:

    Thanks for this, Jake. I’ve loved your writing for a long time, but I found this the most interesting post of all. I’ve been keeping a spreadsheet on my sex life since the very first time I had sex at age 18 (now 33). Over 500 partners later, the data collection has evolved a great deal and I now record information on over 50 variables! You’ve inspired me: I think it’s high time to really look carefully at all the information I’ve collected, and also, I think it’s time to add a comments field like you do. I agree with you — your comments on each encounter were really, really interesting. Thanks.

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