Sex with Someone “Out of Your League” … A Boost One’s Confidence? Or A Reality Check?

Every gay man has a story about someone they’ve hooked up with that they deemed better than the rest. Within this is a group of men who claim that the guy in question is one they consider to be “out of their league.” They feel like they just scored a home run when their batting average is .208, won an Oscar when they were shocked to just have been nominated, finished first in a race when they just were hoping to finish at all, or any one of many metaphors.

Does this type of hook up boost one’s confidence in the long run? Or is this type of belief a negative societal issue when we all are really on the same level and shouldn’t view the others as being on some sort of sex pedestal to be worshipped.

From personal experience, it’s a bit of both. Even though I’ve been a huskier dude my entire life, I still had internal confidence where I felt I could approach a guy and see what happened regardless of what they looked like or who they were. I find that a lot of men in our community are afraid to approach others due to fear of the unknown, rejection, and being embarrassed.  But what many need to realize is that most of us are all the same and would react the same, greeting the other person with open arms if they tried.

Something inherently changed in my confidence five years ago that still resonates with me to this day. During my first trip to San Francisco, I did my best to navigate my way through the city to the best of my abilities (with several high school friends who moved there from New York, other gay friends I knew, and also other gay men that I simply met while there).  I had some down time and wound up going on a lunch date with a guy I met off Growlr. I wasn’t that particularly interested in him, but we had a nice conversation and the lunch was superb.

While out with my friends, I’m someone who enjoys being in the moment, so my phone is generally in my pocket or shut off during an outing with them. The lunch date was going well and then he went to the bathroom for a couple of minutes, so I took that moment to whip my phone out to check my messages. I got one on Scruff from an extraordinarily attractive man who happened to be 200 feet away from my current location at that point. Here’s how the conversation went:

Him: Hey cutie, how’s your visit to San Francisco?

Me: It’s been great, how are you?

Him: Pretty horny now to be honest.

He then sent me a professionally done naked photo of him sitting in the corner of a boxing ring with some fake blood on his face while pleasuring himself in a very naughty way. After viewing said pic, I responded with “Can I come over?”

He wasted no time getting back to me and gave me his address. Then the lunch date came out and we said our goodbyes.

I then ran like Usain Bolt in the Olympics to his place, which I still give no f***s about to this day, because it felt like some weird fantasy come to life and I couldn’t wait to see what was next. He opened the door shortly after I knocked on it, where the stud in question sported nothing but a white tank top and grey sweats where the print could’ve been spotted by a blind person.

He then pulled me inside and started to make out with me. I closed my eyes but opened them to get a view as to what I was really looking at. This dude was incredibly hot, insatiable, but at that point I thought he was out of my league. My paranoia also ran rapid to where I even thought he could’ve been an escort and wanted money after we were done.

We went upstairs, continued to make out and I pushed him off of me for a couple of seconds amid my ridiculous mindset.

Him: What’s wrong?

Me: I’m kind of confused here. You look like you, and I look like me.

He then grabbed my shoulders and said, “So what’s the problem? You’re f***ing hot. Let’s get it on.”

As odd as it sounds, my mind did a complete 180 after he said that, and some confidence shot right up inside of me that I’ve never had before. Any sort of insecurity that I had when it came to hooking up with a guy like this went right away and we resumed our very fun sexual activities. He’s fully aware of the fact that this was easily one of the best sexual experiences I’ve had to this day, as I’ve reminded him of it pretty much every year since.

So, can hooking up with someone who society might deem as “out of your league” improve your confidence? Yes, but at the same time, you should already have it in your system that you are enough. Hooking up with a guy who you could view as some elevated trophy of sorts is great to think about, but this community must understand that we are all on the same playing field. You aren’t better than me, and I’m not better than you.

So pat yourself on the back the next time you hook up with someone that you deem as attractive. Because chances are… they are thinking the same about you.


This post was created by one of our Contributing Writers and does not reflect the opinion of Instinct Magazine or the other Contributing Writers when it comes to this subject.

Leave a Comment