Wilderness Tips: A Survival Guide For Your Sexual Adventures

I’ve always been drawn to the wilds of things: to what’s uncharted, unpredictable, undomesticated, organic, tangly and full of surprise. I love the frequent wilderness experience of an at-least-a-little-bit-overwhelmed immersion in unknown or ever-shifting terrain. I often feel really excited when I feel a little unsure and even a little precarious or unstable. I was never that kid who had to be pushed to go off on their own: I was the kid that always went off on their own even when I wasn’t supposed to, the one some panicked person or another had to find once they realized I was gone. I’ve been an adventurer in a whole lot of ways for as long as I’ve been anything.

I’m in love with actual wilds: forests and swamps and mountains and all kinds of other (often) exquisite natural marriages of order and chaos. I dream of Tasmania and Nepal and parts of Louisiana or Mexico only locals know about. I’m also drawn to the wilds of the creative process, and to new or experimental ways of thinking or doing things. I’ve often been drawn to the wilds of sexuality, sex and sexual relationships, too.

I love it in the wilds of things. LOVE. IT. (Got that?) I feel like I’ve come home every time I find myself facing the opening to the wilderness, no matter what kind. The adventures may vary, but the feelings I have with them are always big and bright and raring to go exploring. Adventuring — even just the prospect of it — is one of the things in life that reminds me most exactly why I choose to stay alive and how I feel when I feel like I’m really living.

The wilds are unscripted. I get to explore and enjoy beginner’s mind in them; the freedom of fewer expectations and not having to be any kind of expert, just another newbie and fellow traveler. I like getting lost sometimes. I like opportunities to learn and experience new things. I like never being 100 percent sure about anything; it keeps me interested and playful. I like the multi-sensory experience of all kinds of wilds. I like the neurochemicals of adventuring: the adrenaline, the endorphins, the dopamine. I also like that I have to be hyper-attentive in a lot of ways when I’m in any particular wild. I’m a highly observant person by nature, and it’s something I like about myself. My senses tend to be amped up in the wild, and so I not only generally have more to observe, my brain is more inclined to joyfully geek out on what I do observe, and has more to geek out on. At the same time, the wilds often can put me in really focused, reflective spaces, too. When I’m adventuring with others, the wilds give me ways to really cooperate and collaborate, to be part of a real and very active team, to create the kind of bonds that I think really only happen when you’re sharing or have shared some kind of adventure together.

I like who I am in the wild. In the deep of things that feel bigger than me, I’m more emotionally open. I’m humbled, alert, attentive, engaged, connected, awake and curious as hell. I’m in love with or fascinated by seemingly everything. I’m at least a little bit sweaty, a little bit scared and full of a little bit of mischief.

Exploring and enjoying the actual wilderness is very widely culturally accepted, if not outright celebrated and applauded. There are a lot of beautiful, widely-revered books and other works of art about exactly this. Exploring and enjoying the sexual wilderness, on the other hand, is generally not met with that kind of lofty appreciation. Even merely suggesting the desire to go adventuring sexually is similar to the desire to other kinds of wilderness exploration can get you some dirty looks sometimes. (RIP my inbox, I know, I know.) But personally, I think the desire for sexual wilderness exploration — and often the most core parts of the experience — comes from a pretty similar place that the want to get in the physical outside and go wild does. I think it feels pretty similar, too, and that going about your sexual adventures with the kinds of smart things you’d do for other kinds of adventuring is a good way to best assure that whatever your sexual adventure, it’s an excellent one.

What is “the wild” when we’re talking about sex? Subjective and totally relative, that’s what. For some people, the wilds are something they have no experience with yet, that’s totally new to them: that could be masturbation; being naked with someone else; oral sex; group sex, kissing. Some people’s wilds are the stuff that commonly gets filed as kinky, other people’s are not. For some people, that might be sex with someone else while fully expressing and affirming their gender; for others, it could be having sex with someone who actually knows you’re a survivor of assault, or something else very vulnerable about you. The sexual wilds can be something like opening up a relationship or being part of someone else’s open relationship or they might be exploring mutual monogamy for the first time. They can be having sex after having a baby. A sexual adventure could be having someone see you naked with the lights on, or maybe even just watching yourself naked with the lights on. You might even find that for you, the literal wild is an integral part of your sexuality in some way (hello, ecosexuals!). Maybe going into the wild for you is even simply (and oh, how not simple it usually is) falling in love and in lust. That alone can be one seriously big wilderness adventure, for sure.

Because we’re always changing, gathering more life experience, finding out new things and — I hope — having at least some kinds of new adventures, what we consider to be adventure, to be “the wilds” for ourselves, will usually change over the course of our lives.

Not every mountain climb ends in tragedy. Most don’t, particularly when people are smart about how they do them. The same is also absolutely true when it comes to sexual adventuring. Let’s see what I can do to help assure that all your trails are happy ones with some of the most basic tips for any kind of great explore.

1) Be prepared (you knew this one was coming).

You sometimes can’t prepare much — and with some adventures, like say, really exploring masturbation, you might not even need to —  but when you can, it’s good to be prepared, just like it’s good to be prepared on a hike or when traveling. Just preparing for something as simple and easy as the chance of rain can be the difference between an awesome experience and one of the most miserable weekends of all time. Research what you want to do. If you’re excited about doing it, that’s usually fun, anyway.  Get the supplies you need, and learn how to use them. If other people are involved, talk and plan together.

Train up, at least a little. Diving right into the Pacific when you have never had any experience at all with waves is only fun for a second, and then it’s just terrifying and awful. For everyone. I know. I was 10, so that’s my excuse. (My Aunt Chanelle's rendering of the experience from my scrapbook is provided for your edification and amusement.)Me, drowning on my own bravado in 1980, by my aunt Chanelle

Whatever your ocean is, try a puddle first. Then a pool. Then a lake. You get the picture. Take a small bite before you eat the whole thing. Give yourself practice using the kinds of skills I’m talking about here — things like quick risk assessment, trusting your instincts and being there for people — in safer situations or places before you take a bigger jump.

Do some intellectual training as well. Just mentally walk yourself through a bunch of possible scenarios with your adventure. When you hit upon likely challenges or potentially negative outcomes, think through some strategies you could use with them if they happen, including exit strategies.

Before you do (or try) anything at all, start by getting yourself some solid risk-assessment skills. We’ve got a guide for that already right here on site. If you’re going to go seeking out and taking part in any kind of adventure, one of the most basic things you need is an ability to figure out what is and isn’t a risk worth taking so you can make any choices that involve risk with the most basic kind of smarts.

It’s vital to be safe with all the things that really matter, and to avoid risks that you really don’t even have to take and probably are more likely to make something a bad experience than a good one. There may even be some whole adventures that you nix because the fact of the matter is that no matter what you do, they just ask for way too much risk from you or someone else or involve risks very unlikely to be worth taking .

2) Make consent and basic ethics impassible boundaries for yourself and others.

The wilds of consent — unless it’s about pushing the boundaries of your own, not someone else’s — are not a safe place to go exploring: if nothing else is absolutely essential, assuring and respecting real consent and just being a decent human has to be.  That’s always vital, but particularly when you’re going places that are unfamiliar with someone else. Now is an excellent time to give yourself a big refresher course on how to do consenting right.

People will sometimes use the idea of adventure as a way to pressure someone else into doing something, like by suggesting someone is cowardly, repressed, and lesser or just not a lot of fun if they don't want to do that thing, too. Some people may even just be so psyched about what they want to do, they don't mean to do that, but their intensity about what they want winds up feeling like pressure to the other person. Remember: real consent can only happen when someone feels as free to say no as yes; as able to set limits or boundaries as to suspend or remove them. Pressuring someone into something sexual isn't an adventure, it's an abuse and a crime.

3) Learn to trust your gut feelings and stay alert.

When we have less information or experience to draw on, or we have to make decisions on the fly, we have to rely on our instincts more.

So many of us have experiences or socialization that's taught us we can’t or shouldn’t trust our instincts. That’s a bunch of baloney, in a whole lot of ways and a whole bunch of places (and so much of it comes from the enabling of abuse in our world, to boot). There’s been a lot of research to show our gut feelings are often some of the most reliable indicators we have to work with, especially when it comes to assessing safety. That little voice, that feeling in your belly, or whatever way you experience the wisest you being like, “Oh hey, wait a second,” or “I know you’re nervous, but go for it,” in a way that feels pretty deep? Let that be what guides you when you lack other guidance or information, and don’t second-guess it, especially when it’s saying, “TURN BACK NOW.” Trust it. You can.

Being in the wild can feel really intoxicating, even when you’re stone-cold sober. It’s easy to feel giddy and dizzy: that’s usually kind of the point. But if you get so caught up in how it all makes you feel and forget to be sure and still keep your bearings intact, it can be something that can turn great adventures into hellscapes and good times into bad ones. Do the best you can to at least check back in with your literal and emotional base camp — alone and, when others are involved, together — rest up for a sec, review, reflect, and check in often. Balance out any floaty feelings with plenty of attention to your surroundings, including other people, and feelings. I personally always think it’s a good idea to just err on the side of caution and step back or out if anything gets your spider senses tingling.

4) Don’t be a jerk.

There’s a pervasive idea that being sexually or interpersonally adventurous means being a shitty human. It doesn’t and it sure shouldn’t. People with bias or ignorance often view the bulk of us on the basis of the few folks who make up the lowest common denominator. Adventurers, sexual and otherwise, can certainly be jerks sometimes, just like everyone else, but no one has to be just because they’re engaging in or like some kind of sexual adventure.

Beyond consent, honesty and care for everyone’s physical and emotional health are some other areas of basic ethics in the decent care and keeping of yourself and your fellow humans. For example, deception in anything — whether that’s dishonesty about relationship status or intentional misrepresentation of one’s own real capabilities  — is not an arena that’s often ethical to dabble in for fun, nor is something like risking potential pregnancy when that’s not what everyone involved wants and are okay with. Actively doing what you can to avoid doing yourself or others harm, and treating yourself and anyone else involved with kindness and respect, are necessary in order to be sexually ethical in the most basic of ways.

5) Be ready for unexpected or challenging social or emotional surprises when fellow explorers have big reactions…and they’re not all good.

Some people will do an experimental thing with you, and even really be into doing it with you, and into you, presumably, when they do, and then freak out and pretend you don’t even exist and like what went on never happened. Sometimes they might do one worse, and use the intimacy they had with you to hurt you. One common place this often happens is when people explore sex with people of the same gender: it’s not uncommon for people’s homophobia to backlash after wanted sexual experiences, and for them to react in an awful way, like by outing someone else without their permission.

Sometimes that person who has the big, unexpected reaction or freakout may be you. (I have myself been this person.) Pro-tip: tell a trusted friend about your plans in advance. If whatever you have going feels like a coming adventure, you probably won’t be able to help yourself, anyway. Ask your friend if they can be there as an ear, support or reality-check for you if you do have a big reaction you’re not expecting, or just if you need some support.

 It can get intense out there. Going into the wilds of things isn’t just risky for, sometimes, our immune or reproductive systems, or our social circles, but for our hearts. Even when the experiences we have out in the wilds are great, it can be emotionally intense. If we have those experiences with others, it can amp the intensity even more, for us as individuals, and for us together. How we or others react to that emotional intensity can be all over the place: it may make us feel very bonded, or make one or more of us want to get and stay the heck away from each other. We might feel at peace or conflicted, more freedom or more shame, more comforted or downright terrified, even just of ourselves. We may find we feel closer to someone else than we (or they) wanted or expected, we may find that we feel further away from them than we (or they) wanted or expected.

This is the kind of risk you’ll often be taking when you go to wild places.  Generally, the more you get to know someone else and the more times you go these kinds of places with them, you’ll have a better sense of your emotional risks. But when someone or something is brand new to you both, it’s much more of a crapshoot. Just be sure to take these kinds of risks into consideration when you’re making your choices and doing what you can — which can certainly include communication! — to prepare for your adventure.

6) You can have adventures without becoming an adventurer full-time.

You don’t have to be “that” kind of person. Choosing to do something sexual or interpersonal outside norms or knowns doesn’t sign you up to be That Kind of Girl/Guy/Octopus evermore. There’s no “kind” of person for just about any one sexual thing in the first place, but doing something also doesn’t automatically enroll you as that thing’s personal representative from then on.

Just because you ate a tomato and liked it didn’t afterwards forever oblige you to be A Serious Tomato Person or to now need to identify yourself as tomato amorous because your like of tomatoes that time was apparently just that important. But of course, if you want to do those things — with tomatoes or something sexual, or hey, both — and surmise you liking a given thing does, in fact, make you a kind of person where that’s a lot to do with you, there’s nothing wrong with that, either. Point is, you get to try things and do things and not have them become some giant part of your life or who you are if they’re not or you don’t want them to be.

That said, know that other people aren’t always so wise about this, and some will decide — sometimes privately, to themselves, sometimes publicly, to other people — that you are “that” kind of person. And when sex and anything that’s considered outside what’s normal or common or current mix, “that kind of person” is usually coming from a place of ignorance and bias, the kind that inclines people to consider or call “that kind of person” things like a slut. (If you’re in need of a little reminding about how slut-shaming is crap, and want a little help undoing any internalizing you’ve done of that, click on over here.) One of the things to think about and plan around with sexual adventuring is who you’re going to include and who you’re going to tell. Even though we can’t always predict in advance or know for sure, I encourage you to try and choose people to have adventures with or tell about them whom you are awfully sure won’t be a terrible jerk about it.

7) Don’t get cocky.

Yeah, you, smartass. Look, you know adventuring in any given way at any given time isn’t right for everybody, probably because there’s wild or riskier stuff that you’re not going for because it’s not for you. It can for sure give you a high to go exploring — see: all mountain climbers ever — and be a thing you want to talk about in your great excitement, but a) don’t forget to consider and honor everyone’s privacy, b) check your privilege when it comes to both the opportunities you were afforded and the risks you can even afford to take that would have others risking way more and c) remember that leaving other people feeling like failures because of your grand conquests usually makes them feel sexually shitty, not good, which is of course the very last thing you, you great sexual adventurer, you, want for people. This portion of advice brought to you by a very repentant adventurer of yore who only made these errors many times way back when, but who also still feels like an ass about it. (Sorry, everyone. Truly.)

The same goes when it comes to your own bravado.  It’s easy to get an inflated sense of what we can handle, and it can also be easy to get so into the feeling of taking risks that we…well, that we get stupid. Getting cocky can make us feel more capable than we actually are and result in foolish choices. Capably exploring can for sure big you up in some ways, and there’s nothing wrong with that, so long as you don’t get too ahead of yourself. Stay humble.

8) Don’t die on the mountain.

That is sometimes literal: some sexual adventures do or could put us in life or death situations. Take care of yourself and be smart. Don’t die.

But most often, your literal life won’t be on the line. However, you will often have the chance to really hurt yourself or someone else in some way or just make an unholy hot mess of things. There can be moments in great chaos where it’s actually super, duper fun to be in the eye of whatever your brand of hurricane. Those moments pass. Fast. And what’s left after is usually not at all fun. So again, employ all the skills we’ve talked about so far -- and here's a little extra about making choices when we have big, heady wants in the mix -- and see what you can’t do to find the place that’s wild fun everyone can live through and with after the fact. And:

9) Pick up your garbage.

We can make a real mess in our adventures sometimes, including emotionally. If and when you do — and if your explorations involve other people, just by virtue of all of us being human and sex and other kinds of intimate socialization being complicated, you will make a mess at some point — make an effort to pick up after yourself. That might mean taking responsibility for something and just apologizing. It might mean making amends. It might mean having to listen to someone tell you things that harsh your buzz in a big way. But whatever it is you need to do to clean up after any messes you make, just do it.

Always just plan to show up for aftercare for any partners (and for yourself!). Sometimes someone won’t want or need it. That’s okay. There's time to grab breakfast, then. But sometimes they — or you — will, and what that aftercare might look like can vary. It can be a big, emotional support because of a big, emotional experience, but it can also just be having a good laugh together afterwards because that’s what’s going to keep whatever you just did together from making things weird. Someone also might ask you for aftercare days, weeks or even years after the fact. If you ask me, figuring that we should make ourselves available even in those circumstances is a caring thing to do, but also can help to make decisions with stuff that might be iffy for us or others. Not wanting to be available for aftercare for someone is often a clue that maybe that someone, or that given thing with that someone, isn’t the way to go for us, or we aren't for them.

10) Have an amazing time.

Enjoy yourself. It is usually exhilarating to go adventuring. Our hearts usually beat a bit faster, we’re maybe that weirdly giddy mix of anxious and excited. Risk-taking, which is usually part of the mix in all this, often delivers one heck of a — totally legal — neurochemical kick, and that can feel really awesome. And that’s besides whatever you’re getting chemically just from feeling or doing anything sexual. Probably you want to do whatever it is you’re thinking about, or already doing, expressly because it makes you feel good; because you want to have fun. So, by all means, give yourself permission. There’s still so much entrenched and active cultural shame when it comes to sex, period, but all the more when it’s anything — or involving anyone — that isn’t considered highly normative. Don’t let that malarkey keep you from enjoying and being enriched by your own experiences; from feeling good before, during or after.

Adventure should primarily be a Choose Your Own Adventure. Adventuring should be about what you want to explore and do, and the experience you’re looking for; it’s about how the person you are uniquely fits (or finds they don’t!) into whatever great, wild expanse you’re exploring. If and when something isn’t what you were actually looking for, or changes somewhere along the way, don’t forget that you don’t have to follow through with your initial plans or pace, and you can always change your mind and just stop, ditching the whole thing if you want.

Be bold. Be brave. Be the good kind of badass. People often elevate those things — boldness, bravery, badassery — when they show up in every other part of life, but then make them something icky or shameful when they’re about sex. That’s bollocks.

It’s brave to go a little outside a comfort zone with the aims of exploring mutual pleasure and experiencing self or shared discovery or growth. It’s brave and bold to take positive risks in your sexual life while also doing all you can to insist that everyone involved, yourself included, is going to do their best to make it a truly positive, beneficial experience. It’s being the good kind of badass to live your life — including your sexual one — as fully as you want to, in the ways that you want to, even if they’re off the grid sometimes (or all the time!). For some, that includes sexual adventuring of some kind where you’re good to yourself and any others, and that probably expands, illuminates and maybe even wildly celebrates your sexualities; this part of who you are and your life. That, all by itself, is often uncharted territory for many. That is one heck of an adventure. Happy travels.

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