Ask JT! The Gay Youth Edition! (Turns Out It’s Not Wasted On The Young.)

As always, your friendly neighborhood bartender is taking a break from his wild dating life to tackle your questions with his patented blend of advice and adult beverages. So slide on up to the bar my friends. Now, what can I get you?


Hello JT! Before I get down to the meat of this question, please allow me to faun over your dating chronicles. There are few things I look forward to more (Friday and the latest issue of LFG) on a thursday night than your SGM Seeks LTR in NYC column, and reading it always lightens my mood, regardless of how I felt beforehand. Now onto the task at hand:

I met my bf a little more than a month ago, and I really like him. We get along well, we have similar tastes, and we can relax in each other’s company. For an 18 year old who’s fresh to the dating scene, I would call that a rare catch that I should meet a guy like that this early on. The problem emerged in the bedroom. Before meeting him, I had recently turned 18, and was having an awesome time getting acquainted with all the fine men of my home city. With my bf, the problem has been the specific act of intercourse.

I’m still not terribly used to bottoming (I’m a top who wants to enjoy bottoming, but so far it’s not working) and I don’t enjoy topping him. This has led to a slow haul of the two of us spending time together and not really having full on sex. He and I are both busy with our respective lives (He works a lot, lives in the city; I go to school and work plus live at home in the suburbs) which makes it hard to see each other but once a week.

My eyes are starting to wander, and while I’ve suggested some things to him, he met the idea of threesomes with ambivalence and an open relationship with hostility. I really like him, but I also feel like I’m restraining myself by being in this relationship.

What do you advise Mister Riley? Stay with him even if it takes months upon months before we can consummate sex? Or sever things and move back to the tricks and turns of today’s gay landscape?

Hey, thanks for plugging my column, dude! Always appreciate when my readers enjoy my writing. You know, you really mean a lot to me.

And since I love you so much, let me give you my first bit of advice right now: stop being such a little tool.

I’ve found that there are two types of people who write into my column. People who are looking to be advised, and people who need to get adviced. And you, sir, need to get adviced. HARD.

Let’s break it down. You met a great guy. Great guys who you can relax around are rare and precious gems, and should be treated as such. Now, you’re fresh on the dating scene, and after an initial bout of passing yourself around like the cookie tray at an office party, you’re with one dude.

But you can’t seem to accomplish a particular sexual act that takes a lot of practice, time, and patience to achieve, so your eyes are already wandering. Strangely, this guy who you get along with so well got pissy when you talked about bringing other people into the equation, and now you think by staying with him you’re ‘restraining’ yourself.

Let’s do the math. You’ve been together a little over a month – which is no time at all for an adult relationship, bee tee dubbs – but you can only see each other once a week. So, you’ve gotten together, what, five times?

You don’t see the root of the problem here? Seriously? God dammit, what the hell is wrong with you kids these days?!

All right, now that that’s out of my system, I’d like to briefly talk to this reader in private, so Internet, do me a favor and step out of the room for a minute.

Are they gone?

Okay, kid, here’s the deal. Don’t feel bad about being a slut. A lot of gay guys, yours truly included, go through a slutty period when they first come out. Sorry if I sounded a little harsh back there. This is foremost an entertainment column and you gotta give the people what they want, which is the occasional light verbal dickslap every now and then.

You came across as a little selfish in your letter, but that’s because you’re still finding yourself and, more specifically, finding out who you are in the dating world.

Let’s talk about your boy for a sec. It’s great that you guys get along, but it also doesn’t really sound like you’re on the same page in terms of the things you want. You’re okay with not being monogamous, and he isn’t. I know you probably don’t want to hear this, but that’s what we call a very likely deal-breaker. What might be best is for you guys to sit down and have a serious talk about what you expect out of a relationship.

When you do, make sure to be respectful of his feelings, because this can be highly emotional territory, especially for younger dudes who haven’t been in that many relationships. For monogamy-oriented individuals, hearing that their boyfriends wouldn’t mind getting plowed by a dick other than their own is perceived as a huge rejection, so tread lightly.

Okay, now for anal sex. Anal sex is great, it’s intimate, it feels amazing for both parties if done right, but here’s the thing: it takes time to master. Let’s put it this way: say you want to take up a new sport, like basketball. (God help me, I’m about to make a sports analogy.) Are you going to know all the rules instinctively? Are you going to be able to make a basket every time? Are you going to … um … do layups – okay, I don’t know what the f*ck I’m talking about.

“It’s sort of like … nope. Nope. Sorry.”

But here’s the point: as with learning anything, you need to go slowly and carefully and allow for some (or a lot of) mistakes. And the best way to do that is with someone you really, really trust and aren’t easily embarrassed around. It’s up to you to decide if the guy you’re with now makes the grade.

And it’s also not the be-all-end-all of gay sex. You say you haven’t “consummated” your sex life yet. But if you’ve jerked each other off, blown each other, rubbed your c*cks together, or in short had any contact with each other to provide pleasurable sexual feeling, you’ve already been having sex, buddy.

Anal sex is but one option on the menu. Or one butt option on the menu. However you want to say it.

Finally, if you do decide to end it with this guy, I’m not going to tell you to not be a little ho bag, because you’re old enough to make your own decisions. But if you do go that route, please please please use protection. No exceptions. No matter what. Deal?

And I will defer my final bit of advice to a much wiser man than I who goes by the name of Burt Hummell. “Don’t throw yourself around like you don’t matter. ‘Cause you matter.”

Best dad ever, am I right, folks?


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