No, not my first time but I had reason to think about guys looking to have their first sex with a man – or first real sex if they somehow don’t count anything they did before they were an adult (some guys do make this distinction). The thing that I’d very strongly suggest is that before they act, they give googobs of thought about what they want to experience and, just as important, whether or not they believe that they can do whatever they’re thinking about.
Over the years, I’ve run across many guys who really didn’t give this a lot of thought before the fact and impulsively went for the gusto with the first guy who agreed to do them… and they’ve regretted it and all because they didn’t think about what they wanted to do, whether or not they could actually do it, and the kind of guy they wanted to have their first time with which is, preferably, someone who will help you through this before, during, and after the fact. I don’t know how many times I’ve been on the verge of giving a guy his first time and he’s told me he really wants to suck cock – only to have him vapor lock or otherwise seize up because it’s one thing to think that sucking a guy’s dick will be nice… when it’s not all nice and hard and literally in your face. They’ve said things like, “I really thought it was gonna be easy to do!” or give voice to some other thought along the lines of the reality being so very different. Then again, I’ve had guys just go down on me and deal with it – then tell me later that it was easier for them to not think about it and just do it.
Sometimes, that first time just happens at the spur of the moment and seriously unplanned – which is why it’s best to think things out to the best of your ability and have a clear idea in your mind – and also with the thought that no plan survives first contact – things can change for any reason and at any time. I think it’s best to not have any expectations; that can be a quick path to great disappointment and I’ve also seen a lot of guys become totally disillusioned with this part of their sexuality because what they thought was going to happen and what actually did happen weren’t even close to being the same thing and, in some cases, their first time will be their last time. One should try to adopt this kind of thinking: Just because it didn’t work with that particular guy doesn’t mean it won’t work with a different guy!
Then there’s the all-important question: Who gets to take your cherry in this? I’ve read that a lot of guys make the “mistake” of going for their first time with a friend or someone they’ve known for a while (like maybe a co-worker) – it’s a mistake in the “you never shit where you eat” category. Still, it makes sense because it’s better the devil you know than the one you don’t; some guys are just way too leery about having their first time with a total stranger unless, of course, they’ve had sufficient time communicating with the guy so that they’re no longer that much of a stranger… but that doesn’t always happen and especially if the potential first-timer has taken to websites to find someone to have sex with. In my experiences with this, eh, there aren’t that many men who are willing to take the time to communicated beyond, “More fucking, less talking!” They can be crude and impersonal and, well, who wants to deal with a guy like that for their first time?
I know I wouldn’t…
The selection of a guy very much depends on what kind of bisexual you are. Are you the romantic kind of guy or are you just the sexual kind of guy? If you don’t know this about yourself, yeah, maybe you need to do some more thinking. Are you the kind of guy who’d be happier letting the other guy be in charge and dictate what’s gonna happen… or are you the one who wants to do the dictating or the kind of guy to whom such things don’t really matter? If you haven’t figured this out – and it’s possible not to know this before the fact – you might want to give a little thought to this because the kind of bisexual you are is going to weigh heavily on the guy you want to give it up to for the first time.
While you have the “who can I do it with?” question on your mind, give some thought about how you want to proceed in this. Do you just wanna dive in and whatever happens is okay… or do you want to start slowly and deal with one thing at a time? Some guys just throw caution to the wind and go for it… with varying results and, sadly, not always good ones. Some guys take it slow by starting out with just being naked with another guy, then progressing to masturbation – mutual or just doing a solo act in front of the other guy; then they go the next step – some cock sucking – maybe they opt to be sucked first to see if it’s really any different from having a woman do it or, of course, want to be the one doing the sucking. Some guys stop at this point because the next “logical” step is anal sex and, yes, at first, it is as scary as you think it is to be on the receiving end; it can also be a bit of a letdown or just plain embarrassing when you want to do the fucking… and your erection goes on vacation as you’re trying to get it in the other guy.
And, no, I really don’t know why this happens! Yeah, I’ve seen guys be so deliciously hard, put a condom on and… bye-bye erection. Going in bare, well, these days, that might not be a safe or smart thing to do if you don’t really know the guy and/or the proper preparations have not been made. Yeah, there’s that whole heat of the moment thing – and do not kid yourself into thinking that this can’t or shouldn’t happen because it can; you might go into your first time thinking that you’re not gonna do the butt thing… and find yourself all up in it one way or the other.
This situation can frustrate the shit out of a lot of guys looking for their first time because (a) it’s a lot of shit to think about and (b) they really don’t have any idea of what they should be thinking about before the fact… which is why I’m writing this. Is it easy to have that first time? No… but it could be – it depends on a lot of things that, at the very least, a guy looking to have his first time should, in my opinion, think about well before they actually do it. Have a “plan” in place but be very much aware that it could change; I don’t know how many times I’ve not been looking for some man-sex and it’s found me so, yeah, it’s good to not find yourself saying, “Oh, shit – what do I do now?” You can have a general idea of the kind of guy you want to be with for your first time and you’re even looking for him – and out of the blue, a ready and willing guy just “finds” you and tosses your search right out the window – you just never know who you may run into that’ll turn out to be the guy you’ll wind up having your first experience with.
One’s first time is so damned important because it’ll be what determines how he’s going to handle his bisexuality going forward and, as a “side effect” he’s going to learn a lot of shit that women already know. No, this doesn’t imply any “gayness” but I can pretty much guarantee you that you will be able to see sex from a woman’s point of view and how men are about having sex, like how giving a blowjob can wind up being low on your list of things to do or finding out that having some guy pounding his dick into you as hard and as fast as he can ain’t always a fun thing to experience and, oh, yeah, bigger dicks don’t always mean better sex. If you’ve ever held a woman’s head down on your dick while she’s sucking you or otherwise try to ram your cock down her throat, I can guarantee you that you will find out why women pitch a royal bitch about this.
Right now, I don’t know what else I can say about this; there just isn’t a tried and true method for going about having your first time. You gotta rely on your ability to communicate, to be able to read body language and, really, sometimes just trust your gut feelings; the risk isn’t what might happen – the greater risk is being wrong in your assumption about other men – some guys don’t have a sense of humor about being hit on by another guy – or, even worse, letting your fears dictate things. It’s important in any of this to be as safe as possible and I’m not just talking about having safe sex. Think first, then act if you must should be, in my opinion, the one thing that will always stick in your mind and, yeah, in those spur of the moment things, you’ll learn how to think very quickly if you don’t know how to do that already. Your first experience should be a damned good one… but you should also be ready (and have a “plan”) just in case it doesn’t go as well as you hoped.
I know that when I’ve given a guy his first time, I want him to have the best experience possible but I also want to be sure that giving him that first experience is going to be the best thing for him to do so, yeah, I have not given them that first time because they’ve showed me that they’re not quite ready for it despite what they may have said. I’ve told them, “You have to be sure you really want to do this…” because, of course, I’ve seen what can happen when a guy isn’t sure; ah, man, there’s nothing worst than being with a guy who learned, at the moment of truth, that he wasn’t ready and just totally freak the fuck out.
So if you don’t want to be that guy, please do some due diligence and think first… then act if you must.