Squirt.org Readers Ask: How Should I Have My First Bi Male Experience?


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If you’re a guy who usually has sex with women, but you’re a bit bi-curious – at some stage, you’re probably going to want to explore that side of your sexuality and get a taste of a bit of man-on-man action.

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A while back, we covered how to prepare for male sex for the first time – that’s a good grounding for everyone. This time around, we’re going to focus on bi-curious guys who want to get into the guy-on-guy game.

For lots of reasons, crossing that line can be a pretty big deal for a lot of guys. Turning those fantasies into reality may seem like a great idea when you’re horned-up, but how do you know that it’s something that you really want to follow through on? How do you even go about getting your hands on some dick?

How do I know if I should have a Bi experience with another male?

If this is a question that you’re pondering, it’s fairly likely that your dick is telling you what you want and your brain is in catch-up mode.

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Human sexuality is fairly complex. What’s increasingly clear is that trying to label everything into neat little boxes isn’t particularly helpful for anyone.

If you find yourself watching porn and looking at what the bisexual male porn stars are doing, if you’re checking out other guys in the locker-room, if you’ve created a profile on gay dating websites just to see what they’re all about, or if you’re exploring some ass-play and wondering how to take it a bit further, you’re probably going to be wondering what would happen if you got naked with another dude.

That doesn’t automatically make you gay, or bisexual, or anything else – it just means that you’re a guy who has sexual needs and that you’re open to exploring your options.

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That’s cool. Just because you’re thinking about it doesn’t mean that it has to happen, but if you’re consciously open to the prospect of a bit of guy-fun then there’s plenty of ways in which you can scratch that itch.

Can I keep my bisexual experiences with other guys on the down-low?

Exploring your sexual fantasies is a lot of fun, and sometimes it can enhance the excitement to know that you’ve got some sexy secrets – that no one knows what you’re getting up to on the side.

That may be a bit complicated if you’re in a relationship of some kind. When there’s other people involved – such as a wife or a girlfriend – then it’s healthy to take their emotional needs into consideration as you embark on your sexual explorations.

You may be in the kind of relationship where your partner will be totally up for exploring some bisexual encounters with you. Or it may be a bit of a deal-breaker. That’s something that you’re going to need to figure out and navigate – if you can do that upfront then that’s a lot more straightforward than having to explain after the fact why you’ve been dicking down dudes on the down-low.

How can I meet guys for some man-on-man bisexual experiences?

While the golden age of cruising may be in the past, there’s still plenty of adult bookstores and truck-stops where it’s easy enough to find other guys who are up for mutual jerking off or a bit of fun through the glory holes.

Cruising options are popular with guys who are looking for sex with other men but wanting to keep it all fairly anonymous and transactional. Log onto Squirt.org and browse our Cruise Now feature to find a local gay park cruising spot.

With GPS technology, you can find the hottest spots men are looking to hookup at right now; or, if you plan on travelling, you can use the filter search to pick specific countries, cities and neighbourhoods where you can find well-known hookup spots to have your first male encounter without anyone knowing.

Bathhouses, gay saunas, and sex-on-premises venues are also a good starting point. Everyone is here to get off, and you can get the job done without a lot of conversation.

Get on Squirt.org for Ass Play or Ass Fucking

Hook-up apps such as Squirt.org are not only a great way to pinpoint cruising opportunities, you can also connect with other guys who want to explore their bisexual side, or gay guys who will be more than happy to give you a taste of some man-on-man action.

Online dating platforms include features such as IM chat, video chat rooms and plenty of other ways to engage with other guys. You can sign-up to Squirt.org for free so you can start exploring all of the sexual options available to you.

What if I’m nervous about having sex with another guy?

We’re at our most vulnerable when we’re putting ourselves into sexual situations – especially if it’s your first time or if you’re exploring something that you’re still a bit uncertain about.

How you handle that depends a bit on the context. If you’re one-on-one with another guy, it’s better to be honest about your lack of experience. No one is going to think less of you, asking for a bit of patience and understanding will ensure that you’re on the same page and moving at the same pace.

If you’re at a cruising spot or somewhere like a bathhouse, you might want to just sit back a bit and get a feel for how things work. No one is going to pressure you into doing something that you’re not ready to do – you might just observe for the first couple of times. Take your time, there’s no rush.

Generally, your body will know what to do. If you’re turned on, your cock will be hard and your instincts will kick in. However, if you’re still mentally processing whether exploring bisexual encounters with guys is something you should be doing, you may not get hard and you may not come. That happens a lot – it doesn’t mean anything, just that maybe you need a bit more time to figure yourself out.

What if I’m not sure whether I’m gay or bisexual?

It’s best not to overthink this kind of stuff. Do a bit of reading and you’ll quickly see that human sexuality is complex and there’s still lots that we don’t know about what shapes our desires.

Don’t start with a label and try to fit yourself into that box. Start with what makes you feel good. Give yourself permission to grow and evolve – don’t be constrained by other people’s perception of you.

If you’re fantasising about a bit of guy-on-guy action, what’s stopping you from making those fantasies a reality?

Written by Gareth Johnson

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  1. Great article, summed up a lot for me. For years I struggled with being attracted to women and men, adamant I had to be one or the other, finally I realised the sexuality spectrum is huge and that I’m pretty much 50/50 bi. Some days it’s more men others more women, can last weeks in either direction. I love it, feels like I have the best of everything. Sexual freedom.

  2. You’ve really got to stop telling guys who are actively seeking sex with other men that it doesn’t mean they’re gay or bi. The innate homophobia of letting those guys tell themselves – or worse, those of us they hook up with – that they aren’t gay or bi – which really only leaves them pretending to heterosexuality – has to be challenged. It feeds the notion that gayness or male bisexuality are ‘less than’, or inferior, and that the ‘experimenter’ has some kind of superiority, and is remaining outside the group he’s actually having sex with. The idea that ‘straight’ men are in any way superior, or that gay sex is something to keep quiet or feel shame about, just belongs to a time that should be over. Stop keeping it alive. Tell guys that yes, it means you’re bi or even possibly gay, but that’s not something to be ashamed of, or to deny.

  3. I consider myself bi, even though i have no experience in anal and limited experience in oral, because if I’m getting turned on thinking about sexual things with other guys and have joined gay sites looking for hookups, i don’t think im 100% straight anymore. If i find i don’t like receiving anal when that happens, i will always want to give and recieve oral. And will still want sex with women. But I’m currently in a relationship, so meets are limited and coming out as bi is not an option yet. But hopefully one day i will say that I’m bi sexual openly.

  4. I had my first affair with a younger gay man back in 2019, having met him on Squirt. He was kind and patient and allowed me to explore oral for the first time, a longtime fantasy that was very pleasurable for us both. I had multiple meets with him, and thoroughly enjoyed our time together. I have been with one man since and don’t think I’ll ever be able to or want to ignore the erotic nature of myself with another man again. Still attracted to women and married, but would like to get honest with my wife soon out of respect for her feelings. We haven’t had sex in over five years so I’m hoping she will understand.

  5. I’m fully Bi.
    I think the article was brief but touched on lots for further thought.
    I would not take a chance on tipping the apple cart but telling your partner no matter how much you love them.
    The cheating… It just happened. The desires undermines the love they thought they had from you.
    Your relationship dynamics will change, you could even be the victim of spite and forced out among your closet friends. No matter what they say, you’ll be looking for new friends and probably a new partner as one of your ‘friends’ will see their chance.
    Trust me, loose lips really do sink ships. 😭

  6. I disagree with Activsw17.
    It has nothing to do with homophobia, inferiority or superiority.
    The simple fact is that a person doesn’t have to be Gay or Bisexual to enjoy sexual interaction with someone of the same sex.
    Take glory holes as an example. It doesn’t make any difference who’s on the other side of the wall sucking cock. You may never know if it’s a male or female.
    Sexuality is way more than what goes into what hole.
    Lots of Gay guys have sex with females as well but when it comes to relationships, they are only attracted to guys.
    Lots of Straight guys have sex with guys but it’s purely on a physical level and when it comes to relationships, they are only attracted to females.
    Bisexual guys are attracted to both guys and girls when it comes to relationships.
    Another misconception usually promoted by Gay identifying guys is that if a guy claims to be bisexual and has only had relationships with guys for the last decade, he must be in denial, unable to come to terms with his sexuality or for some reason, in the closet. He might be Bisexual and just comfortable with the relationships he’s having or not met a compatible female.
    How we choose to identify at any stage of our lives and why is a very personal decision and we shouldn’t allow others to dictate that.

  7. One of the “safer” ways to explore is through a massage/bodywork. It’s not difficult to find a massage therapist or provider who offers a more sensual experience. Clearly curious men should avoid a male massage therapist to whom they haven’t been referred or found on an appropriate site. I’m a massage therapist and have worked with married/bi/curious men who sought a more erotic or sensual experience. Be sure your therapist understands discretion and safety. Hope this helps…

  8. Tony9154;

    Very well said.

    Yes I agree with you when you say that lots of straight guys have sex with guys but only on a physical level. Then, in regards to relationships, only attracted to females.

    That’s sort of explains my Outlook.

    However, I will say this, when I’m looking at photos or videos, my cock basically leads the way.

    Even though I enjoy straight sex, I’m really turned on when watching gay porn, or viewing photos of naked men, engaging in sexual activities.

    On my profile on this site, I state that I’m bisexual. I guess that’s as close as it’s going to be to what I really am at this point.

    But I am not that focused on labels or whether I’m bisexual or not.
    I just know that I really enjoy watching men having sex with other men.

    But due to a medical condition, I am unable not able to prescribe to Prep. Thus I have no interest and engaging in anal sex. However, I certainly enjoy sucking cock, that much I do know.

    When it comes relationship though, I only have interest in women. Therefore, I have no romantic interest in men. Purely sexual, or physically attractive, with men, that’s all.

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