Should I Sleep With My Straight College Roommate?

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The Problem

Hi, Jack,

I have a weird problem that I’m sure you will think is just is just ridiculous. To cut to the chase, I’m in my second year of college and living in the dorms. I also happen to be gay.

This year, the powers that be decided to pair me up with a ridiculously hot jock who I’m 99% sure is straight. I mean, he hasn’t come out and said it but that’s just the vibe I get off him.

All he ever talks about are the girls he’s banged. Well, that and sports. What else am I supposed to think?

But here is the weird thing. On three separate occasions, we’ve gotten into wrestling matches. Each time, he’s popped wood. The last time it happened, I could feel his stiffy through his sweats.

When I pointed this out to him, he looked at me and said, “You know you want to suck it.” When I joked back and told him I would, he replied, “Go for it!”

Well, I obviously haven’t done it (yet). It’s not like I don’t want to because I totally do. But I’m afraid it could get weird afterward. Any thoughts?

Jimmy in Chicago

The Solution

Hi, Jimmy,

It sounds like you are in a situation that a lot of guys who visit this blog can relate to. Well, either relate to or fantasize about.

I can imagine this whole thing has been difficult for you. From the sound of it, your roommate is the stuff of “lick and yum” as some folks like to say around here.

So, in reading your post, my sense is you are really attracted to him. Moreover, your roomie also appears to be attracted to you.

We know this because he’s getting an erection while wrestling with you. Well, that and because the guy all but told you to service him.

It doesn’t get any more direct than “go for it”, does it?

I couldn’t tell you if your roomie is [closeted] gay, bi or simply curious. At the end of the day, it’s kind of a moot point because he’s obviously interested.

The essential question for you is, should I sleep with him?

Here’s the thing Jimmy, there’s no right or wrong answer. Much depends on this guy’s emotional makeup and mental maturity. The truth is things could go either way, meaning bad or good.

If you look around this website, you’ll find all sorts of stories about things going splendidly with curious men. But you’ll also read about guys who would never “feed of the seed” of a “straight” roommate.

What may be helpful is to fast-forward your mental tape and play things out. In other words, based on your own experiences of your roomie thus far, how do you think he’ll act afterward?

If you aren’t sure, that could be an indication that maybe, hooking up with him isn’t a smart move. On the other hand, if you feel he’ll be cool with it, then why not enjoy?

Here are a few other things to consider as part of the dynamic. One, if you do go down on him, will he take this as a green light for more activities in the future? Will things escalate?

Additionally, what are your expectations here? In other words, do you want him to reciprocate? If yes, what if that’s not something he’s willing to do? Are you OK with merely giving him bro-jobs at his beckon call?

Finally, is there a part of you who has feelings for him? I’m not saying you do. Instead, I’m merely asking. The reason is that sometimes, gay men end up falling for guys who are emotionally unavailable.

This happens when we start crushing on men who can’t provide us with what we need (if that makes sense).

For what it is worth, I had something similar happen to me when I was in college. The guy who lived down the hall from me started showing interest.

Like your roommate, I figured him as straight. Later, I would find out that he was closeted and that all of his trash talking about the women he had f—– was a bunch of BS.

In my case, I did end up messing around with him. But it only happened once. The reason?

He didn’t want to reflect back what I was doing to him (AKA oral). And to me, that was just a deal breaker. Call me old school but I just think it’s only fair to want that. Maybe I’m wrong – who knows?

Anyway, Jimmy, I encourage you to carefully consider hooking up with your jock bunkmate. Make sure you’ve thought it all out and play that mental tape I mentioned earlier.

If you do end up draining his main and things are cool in the days that follow, that’s totally awesome. Now you’ll have a built-in f-buddy for the school year.

That’s kind of nice on cold winter nights, right?

On the flip side, should you decide against getting with him, don’t question your convictions. Most of the time, your inner voice is going to be right.

Need some dating help? Email Jack, the Gay Dating Coach at: [email protected]

About Jack Eagle 21 Articles
Jack is a wise but mysterious figure whose exact whereabouts and identifying details remain unknown. What we do know is that he's really, really good at relationship challenges. He’s been on more dates than you can shake a stick at, and he’s here to help men from all walks of life step up their game.