Str8Curious: How to Lose Your Gay Sex Virginity

Str8Curious: Here’s What You Should Know Before You Have Gay Sex for the First Time

Str8Curious is a monthly AskMen column where out and proud lifestyle expert Joey Skladany answers burning questions from heterosexual men about sex, dating, and the LGBTQ+ community. No topic is off limits as he candidly lends advice, debunks stereotypes, and gives it to you straight — err — gay. Should you be interested in submitting a question for editorial consideration (and we will respect anonymity), feel free to ping Joey directly on Instagram or email him at [email protected]).

The Question

I think I’m finally ready to have sex with another man, but I’ll be losing my gay virginity in my 30s and am a bit confused about how to approach this situation. I’m equal parts excited and scared, but is there a right or wrong way to ensure I don’t make this more awkward than it should be? – Jamie, Houston, TX

The Answer

First and foremost, congrats on taking the leap to explore your sexuality. Too many dudes get caught up in society-perpetuated hetero norms and limit the breadth of their bedroom experiences out of shame or fear of labels.

Just because you want to penetrate a bubble booty or have the D up your own B doesn’t make you any less of a man. You’re doing what makes you feel good, like noshing on chicken fingers or binge-watching Little Women: Atlanta (just me?) and that is what makes you — surprise — human.

The single most important component of first-time gay sex is to find a partner who makes you feel comfortable. Don’t partake in anal intercourse after a long night of line dancing, swigging whiskey, smoking Marlboros, or whatever you Texas boys do.

While alcohol can remove inhibitions and loosen you up (both metaphorically and quite literally), you can also put yourself in a more dangerously vulnerable situation. The last thing you want is to wake up with regret and have this ruin your perception of gay sex forever.

A perfect partner will always go at your own pace. Ideally, they’ll either be exploring with you (which can be quite fun and take the edge off!) or have more notches on their belt and not take advantage of your newbie status and situation.

They’ll also encourage you to lay out exactly what you want to do from the get-go, while not limiting exploration once the copulation commences.

Questions to answer before lubing up: Do you want to start with heavy foreplay? Are you more interested in topping, bottoming, or both? Do you want to begin with a blank slate and see how you feel in the moment?

There are no right or wrong answers, but the lucky companion must be respectful to your wants and needs and never pressure you to do anything beyond that. Keep in mind that you must also reciprocate this basic courtesy.

If you’ve got bottoming on the brain, this comes with a bit more preparation. The butthole is an unhygienic place (which is natural!) and you’ll want to take steps like douching or eating a fiber-heavy diet to ensure that the rectum is ready for a clean pounding.

This will have you worry less about shitting on someone’s dick and more on having the most intense orgasm of your life. But if it does happen, don’t beat yourself up. Sure, it’s terrifying and sometimes gag-worthy (and, knock on wood, I have yet to experience this myself), but it all boils down to having a partner you can trust and is free of judgment. Shit happens, literally, and anal sex never comes with a 100% satisfaction guarantee.

If your concern is that you can’t take a dick (which is #valid and the reason why I’m no size queen), invest in toys or butt plugs to see if a) they actually feel good and b) your hole can stretch a bit and be ready for the real thing.

I also recommend toy play as foreplay — use a dildo before the actual sex and it may make the both of you want to get down and dirty even more. And always use a ton of lube so that it doesn’t feel like you’re sticking a hot dog down a machete-lined toilet paper roll.

Also, don’t forget to breathe upon insertion. The tenser the body, the tenser the anus. Try your hardest to relax and think happy thoughts. It’s easier said than done, especially because the feeling will be unfamiliar and maybe a bit painful, but a good exhale will open you up in more ways you thought possible.

Lastly, we just delved into the importance of prioritizing sexual health and frequent testing last month. Be sure to use protection and screen for STIs beforehand. You’ll want the peace of mind that you and your partner can engage in the consensual act without fear of medical consequences.

Engaging in anal sex is, as you mentioned, equal parts exciting and scary. But it’s important to keep a positive mindset and only surround yourself with sexual partners who will support this. Also, don’t beat yourself up for experimenting later in life. Even if it is a 40 Year-Old Virgin situation, you have now proactively taken the steps to satisfy an urge and that’s to be applauded.

If you love it, fantastic! Keep spreading your legs — err — wings and fly in the gay abyss of sexual experiences. And if you don’t, that’s fine, too. You don’t know unless you try, so either stick with ol’ faithful (a.k.a. your hand, a mouth, or a vag) or dust your ass off and try again.

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Source: AskMen