Ask GayDemon: Under a Straight Guy's Spell

I've been crushing on this straight guy at work. He has a girlfriend, but we've had several late nights working on a project and he's flirted with me quite heavily. We've "bumped" knees under the desk and he even rubbed my shoulders when I complained of a tense neck. Should I go for it?

-Flirted and Flummoxed

He sounds like he's straight but not narrow. And maybe also his cock is straight but not narrow. That's just one of many factors to consider, though if he's over 6.25 inches around, just have sex with him regardless. I think that's a gay law or something.

If you're his supervisor (or he's yours), then sure as hell don't do anything with him. Unless you don't care about lawsuits. If you're his colleague with no work power dynamic happening, then still read your employee handbook to see what it says.

Sometimes romantic relationships are allowed as long as don't happen while at work and nobody is someone's supervisor. Don't assume that because he has a girlfriend that makes him totally locked down secretive about everything with you. In fact, she may even know about his interest already and want to jill off to his stories about what happens with you.

He also may not have a girlfriend at all. Unless you've seen her in person, you can't be sure. This guy may be going off the semi-reputable idea that some gay guys dig on straight guys. That may have been more true in the past. It's complicated.

Certainly he can self-identify as he chooses, perhaps compartmentalizing sex with a guy away from his sexual identity. Which is totally fair as sexual behavior and sexual identity (especially public sexual identity) are not fully bound to each other. He can think of himself and describe himself however he wants.

My biggest concern here is how you may feel coming in to work the next day if you do have sex with him. Will it distract you from your job, and your career as a whole? What if the sex isn't fun for one or both of you? Or what if it is and you want more but he still looked at it as a one time thing?

Flirting is just that. Not a guarantee of anything except that flirting has occurred in that moment. The neck rub is a very strong sign though. But there are still even more opportunities to flirt, including outside of work.

And considering you have no idea what the actual sex would be like, you may want to consider just continuing as you are now, but seeing if he wants to hang out with you outside of work. Like ask him if he wants to go work out together or play racquetball or something like that. Not where you'd end up naked and alone with him, but just where you can spend more casual time with him.

You may find he gets very shy very quickly as things start to feel more possible. He may have just been sick of work and trying to keep things interesting. So this method would be to see if that energy is maintained, which may mean the risk of actually connecting with him sexually is more worth it, because it just feels like he's more invested in general. Except of course, that it would make him a cheating pig and you complicit in that (if he's monogamous).

But if your goal is to full on have sex with him if at all possible, then just respond to his flirting very positively and give him more opportunities to flirt with you, but still in the context of work. You could even invent an excuse that brings him to your place. Like "I know we need to work late again tonight, but I have some things I have to take care of at home too. Can we bring the work back to my place tonight?"

Or just tell him "I really appreciated when you rubbed my shoulders. I was really tense and it felt really good. Now my ass, penis, pecs and inner thighs are tense. Can you help with that?"

Saying that may seem like a crazy stretch, but you did tap his knee right back. So you're feeling something. Now balance it out with reality and come up with a plan. That may include saying no.

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