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Ask O'Leary: When is it Okay to Stray?

Hi Tim,

I've been with my boyfriend now for almost two years, and I'm absolutely head-over-heels in love with him. He's my first serious boyfriend, and despite how naive I make myself sound, I think he might be the one. Still, traces of regret remain. See, I have a friend who was my roommate in college. We messed around a bit, but nothing happened beyond groping fully clothed. In the past he's expressed interest in messing around again, except for the fact that he had a girlfriend at the time. (He's bi.)

Now we're both graduated college, he's single, and I'm not. Neither of us have romantic feelings for one another, but I still can't get the idea of shagging him out of my head. He's not actively soliciting sex from me, but I find myself keeping my distance from him, because of how tempting I find him. Plus, I haven't had too many sexual experiences before my boyfriend. The notion that I haven't gotten to sow my wild oats really fills me with regret.

So, in short, I feel incredibly guilty. I'm utterly afraid to bring up the idea of having a brief open relationship. What should I do? How do I test the waters? Or, do I try to put this all behind me, and try not to ruin the most beautiful thing to ever happen to me?

Sincerely,

Sexually Nostalgic

Dude, if you were two months into your first real relationship and saying he’s the one, I might worry you’re getting ahead of yourself. But there’s nothing naive about believing you can make it for the long haul when you’ve been together for two years.

Okay, now as for your other issue. You have nothing to feel guilty about right now, because you’ve done nothing wrong. Lust is not something that goes away when you commit to one person. It never goes away. It’s what you do with it that matters.

You have two paths ahead of you. In one, you simply tough it out and do nothing with this friend. Your feelings for him will fade with time, as all lusty feelings do, though it may take years. But just so you know, it’s likely you’ll develop equally boner-promising feelings for someone else. What people in monogamous relationships do in this case is take all that sexual energy and use it when they’re going to town on their partner.

In the other path, you talk to your boyfriend about bending the rules, but know this: I can’t think of a single person who would be okay with opening up their relationship only so their partner can get it on with someone, then immediately snapping it back closed again. That’s just not fair.

If you think your boyfriend might be open to this, you can say that there was always tension with your friend and maybe all three of you can play together. For that to work, though, your guy needs to really, really understand that there are no romantic feelings for the buddy, just dong-related ones.

But you know your boyfriend. I don’t. You have to weigh the risk of possibly wrecking your relationship with the chance of hooking up with your old roommate-- something that might be way hotter in fantasy than it would be in reality.

Hi Tim,

I’m a cis hetero 25-year-old sex-positive female. I’ve been dating an amazing cis bi 28-year-old sex-positive male for seven months. (Does that cover all the bases?) We get along great, enjoy each other’s company immensely, challenge each other intellectually, support each other emotionally, know when to be there for the other and know when to give space. All in all, everything is great, including our sex life.

However, there’s one issue that’s very hard for me to get past, but it’s so minor it’s weird to bring up. He likes when I swallow following oral sex. I usually don’t mind it, but for some reason his...stuff...is incredibly bitter, and it’s really, really unpleasant. Any thoughts on how to sweeten his spunk?

Gagging

I searched long and hard, G, for a definitive, scientific study that dealt with the flavor of semen. I guess science is too busy studying important things like cures to pandemics and why Caitlyn Jenner isn’t spelling her name with a “K,” though, because it doesn’t seem as though there are such studies.

There is, however, a wealth of anecdotal pieces (with zero citations) that discuss certain ways to enhance one’s flavor. According to this piece on Psychology Today , a porn star named Annie Sprinkle, whom the article makes absolutely sure we know tasted “hundreds of men’s semen,” states, “vegetarians taste best, that eating fruit and drinking fruit juices a few hours before sex improves the taste, and that smoking, alcohol, meats, and asparagus make semen less palatable.”

Unfortunately, the article also states urologists generally agree that since the internal makeup of semen is constant, the flavor will be constant as well. But really, when has science or the medical community ever been right about something, you know?

Let your boyfriend know that you’re into swallowing his load, but want to make it a more fun experience for you, and provide him with some apples or other fruits a few hours before getting all nasty up in his biz-ness. Maybe it’ll do the trick. If not, don’t feel bad about making swallowing a “special occasion” event. Many people, men and women both, won’t do it at all, so he should consider himself lucky.

Hey Tim,

I just saw that Jennifer Hudson has a new song out called I Still Love You, and I’m pretty sure it's going to be the gay jam of the summer. Am I right?

Divalicious

Predicting how popular a dance song is going to be is way out of my sphere of expertise, D, but I’d be shocked if this didn’t get some serious airtime for Pride, especially given the video. Jennifer Hudson as a glamorous dance-diva fairy godmother overseeing a straight father reuniting with his gay son on the son’s wedding day? I can see the go go boys twerking to it on the floats already.

Ask Tim O'LearyMore Ask O'Leary! here.

To ask Tim a question, email him at askoleary@gmail.com (and try to keep it to three paragraphs or less). Or you can be super tech-sexy and ask via Twitter.

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