The term “sex ed” or “Sexual Education” probably conjures up high school memories of terrifyingly graphic pictures of STDs, moralistic lectures on abstinence, and a brief overview of what member goes in which orifice (and only in a wedding bed). But sexual education is so much more than that: learning about sexuality is necessary to understanding and appreciating one of the most universal, beautiful, and spiritually fulfilling activities any human can have. Women’s bodies are often regarded as the “fairer sex”, and much-needed effort has recently been made to celebrate and beatify the female form. But men are just as sexually complex, beautiful, and require sexual education in order to fully appreciate sex. If you’re a guy who’s never done the deed, are nervous, or are just optimistic and looking forward to having your first sexual encounter, here are some helpful tips for your first time.
Table of contents
Safety is Sexy
Hopefully you’ve heard this before: safe sex is the best sex. Preventing the spread of STIs and STDs is essential to enjoying your first sexual experience, and it’s important to be prepared.
Ideally, you’ll already know your partner’s sexual background, and your partner has recently been tested for STIs or STDs. But the chances of this are pretty slim. If you’re unsure, ask to go to the testing clinic together—a great way to approach this is as a couple’s activity, saying something along the lines of, “I care about your health, so I’m getting myself checked for any STDs or STIs. Do you want to come with me?”. Never pressure your partner into doing this, but be sure to put the option on the table. Free STD and STI testing is available at many universities, community colleges, and public clinics like Planned Parenthood. The cultural rhetoric around getting tested can discourage people from going, but it’s literally just as essential, easy, and commonplace as a full-body physical or a mental health inspection. There’s nothing to be ashamed of, and you’ll spare yourself from the worry and pain that can come from an STI or STD.
Familiarize yourself with the condom aisle. And this is probably the only time we’ll say this, but measure your penis! Condoms are not one-size-fits-all, and issues with condom fitting can cause uncomfortableness during intercourse or a ripped condom. Sir Richard’s Condoms has a really great, extensive article on how to fit yourself here.
If your partner is capable of getting pregnant, make sure to discuss birth control with them. Let them know you’re interested and supportive in whatever birth control they decide works best for them, whether it’s a pill, an IUD, or some other preventative form. Each type of birth control comes with different sexual needs and nuances, so be open and communicate with your partner about their preferences. Never interrogate or pressure your partner about staying on their birth control, but make yourself an available resource for them to talk about it.
Explore Your Own Body First
Now that the more serious stuff is out of the way, let’s talk about masturbation. Typically, masturbation is a convenient way to relieve sexual pressure: you feel horny, so you want to cum. It’s a fairly straightforward process.
But your body isn’t just a pump-n-go. The next time you feel the urge, experiment with different techniques. Explore how different pressures feel on the head and shaft of your penis. If you’re uncircumcised, note the differences in pleasure from stroking with the foreskin vs. stroking with your foreskin pulled back. Try different amounts of pressure, speed, and timing. Don’t just stroke your penis: your scrotum and perineum, the bundle of nerves between your scrotum and anus, are essential parts of male sexual pleasure as well, and you’ll find that orgasms can come from these areas too, with some massage and touching.
And if you’re a straight guy, don’t fall for the rhetoric of “only gay guys like butt stuff”. Men have a prostate gland that can be stimulated through anal penetration (of anything: fingers, toys, etc), and it’s not like prostate glands only grow in gay guys. Explore this area during masturbation to see if it’s something you enjoy.
Why are we talking so much about masturbation in an article about having sex with another person? Because masturbation is the first step to finding what you like and don’t like sexually. Sex is a give-and-take between two people, and one of the most common issues with first-timers is that they’re too focused on the other person to give themselves any real pleasure. By familiarizing yourself with your own desires, preferences, and dislikes through masturbation, you’ll be able to communicate with your first sexual partner, which leads to less guessing and more awesome sex.
Challenge Your Expectations
Because modern sex ed is so lacking, we usually get our first glimpses of sex from movies, books, and most commonly, porn.
It’s really important to understand that mainstream porn, while a totally fine thing to engage in occasionally, is incredibly unrealistic. With the exception of some amateur, homemade porn, some feminist-focused porn, or other niche genres, mainstream porn generally features a ridiculously hung, tribal-tattooed, coked-out guy jackhammering away at a completely hairless, endlessly flexible tiny girl. There’s no issues with trying to fit the guy’s penis inside of her, you don’t see the awkwardness of changing positions, the guy lasts for like, twenty years, and the girl is super eager to be called derogatory names while getting pounded. And, of course, the girl doesn’t have to pay for her pizza.
You probably know that this is not real life, but it’s important to understand some things going into your first time: as you know, women in porn are usually vastly different from women in real life. Your partner (unless they really are flawless, in which case, nice catch) might have body hair in places you didn’t expect, like around the nipples, down the belly button, or on the tops of their thighs. Your partner will probably not be able to do the pretzel-twisting positions that your favorite porn star is so fond of. Your partner will probably have bumps and scars and other uniquenesses that are airbrushed away in porn stars: all of these fun “flaws” are what makes us beautiful, unique, and human.
There are some crappy expectations that porn places on you, too: don’t feel like a shrimp because you don’t measure up to the uber-muscular porn stars with ten-inch penises. Don’t feel like you have to last for hours or you’ll disappoint your partner. Don’t expect to be able to jackhammer away without needing a break, or some water. Don’t expect to stay rock hard the entire time.
Perhaps the most important difference your sexual experiences will have from porn is the whole intention: typically, mainstream porn is made with the intention of satisfying just the man (or if there’s some kind of female satisfaction, it’s super fast and only happens so that a man can gain pleasure from it). In reality, sex should be a communal experience where both partners gain pleasure. Coming at sex from a mainstream-porn-influenced angle, expecting your partner to cater to only your needs, is not healthy.
There are lots of other things that will probably surprise you during your first time, and I don’t want to ruin all of them, since that’s part of the fun of exploring another person’s body. But just understand that your first time will not be like porn.
Communication is key
Remember how I said real sex won’t be like porn? This is another example of that: the conversations you have with your partner won’t just be you yelling dirty names at them (although that’s perfectly fine in the right context and with consent). The conversation will be much more two-sided, and should involve lots of questions.
Unfortunately, younger women are often told to “grin and bear it” when it comes to sex, and might not speak up if they don’t like something you’re doing, especially if they’re shy and it’s their first time as well. In order to keep that from happening, make sure to ask questions: “does this feel good?”, “do you like how this feels?”, “should I go faster, or slower?” are all great examples of this. Obviously, you don’t need to do this every five seconds, but when you’re switching from, say, fingering to penetration, it’s a good idea to check in verbally to make sure she’s enjoying everything.
This type of communication is important for your own pleasure as well. I’ve heard guy friends complain about a girl using “too much teeth” during a blowjob, and I can’t help but wonder, Why the hell would you let a girl scrape your penis and not say anything? If it’s your partner’s first time, they will probably not just instinctively know the best way to get you off, and this is where the “knowing your body” part we talked about earlier comes in handy. Use your knowledge of your own sexual preferences–what parts like to be touched and don’t like to be touched, where you want teeth and where you definitely do not want teeth–to help guide your partner along. Do not be whiney, critical, or mean, obviously. Use phrases like, “I love when you ___”, or “That doesn’t feel good, let’s try something else”. Understand that neither of you will have absolutely perfect technique, and the only way for that to change is to talk to each other.
Consider trying something like a “Yes, No, and Maybe” chart if you’re both a little nervous and want to know exactly what you’d like during your first experience together.
Learn about consent
Guys, if there is any indication your partner isn’t into it, just don’t do it. It’s really that simple. Save your first time for when you both are sober, both verbally agree to get down to business, and preferably have a relationship already in place.
Having your first time with someone you know isn’t a requirement or a rule, but I think it’s good advice. Sex is a beautiful, spiritual experience that allows you to share bodies with someone. But it also opens the door to a lot of responsibility on our part: there is the possibility of pregnancy, your partner may change their mind in the middle of the act, and lots of other variables. All of these, in my opinion, are most easily navigated when you’re with someone you know and care about. Trying to deal with those issues with a stranger is very difficult.
So, anyway, let’s go over some scenarios you want to avoid if it’s your first time (and probably ever, just to be safe).
- Avoid having sex with a drunk partner who gets all sloppy and can’t remember their own name.
- Avoid having sex with a partner who is silent. If you ask them how they’re feeling, if they’d like to have sex, or anything along those lines, and they respond with silence, that’s a huge red flag to stop what you’re doing and don’t continue.
- Avoid having sex with someone who isn’t 100% sure they want to have sex. If they’re religious, a virgin, or anything else, and have been debating whether to have sex for a while, just leave that alone until they are absolutely sure they’re ready. Not, like, “I guess we can” ready, but literally begging at your feet ready.
- Avoid having sex for the first time if you’re drunk. Not only can you run into problems like not being able to hold an erection, you won’t be able to pick up on verbal or physical cues that your partner isn’t interested in having sex, and you may seriously regret your actions or the actions of your partner in the morning.
None of those scenarios are absolute “never do these”, but they’re definitely scenarios you should try to avoid, especially for your first time. Sexual Violence Prevention Educator Jamie Utt has some great thoughts on consent if you’d like to learn more.
While everyone’s sexual experiences are different, there’s a general “workflow” that’s a good way to start your first time.
Begin with foreplay. What’s foreplay, other than the word you see on the cover of Cosmo once a month? Foreplay is the stuff that leads up to sex: kissing, touching parts of your partner’s body that stimulate and arouse them, and just generally lovin up on each other. If your partner is a woman, begin by kissing, then make your way down to her breasts (remember to communicate as you’re doing this, since not every woman is the same). Feel them, touch them, and play with their nipples (do not, for the love of God, honk them. Or do, if she has a really good sense of humor).
If that went well, and the communication is still going strong and she’s into it, work your way down to her vulva. You were probably expecting me to say vagina, right? No, I mean vulva: the vulva is the outer part of a woman’s genitalia that includes her labia and clitoris. Her vagina is what you’re gonna hopefully put your penis in later on. This is where the communication thing becomes absolutely vital, because what a woman wants during oral sex is wildly different from partner to partner. For some general guidelines, start by kissing the outer edges of her vulva, called her labia, then work your way towards her clitoris (it’s a little knobby protrusion towards the top, and it’ll probably be hiding under a little “hood”, similar to foreskin). Once you’ve got her clitoris, use your tongue to make flicking motions. This kind of repetitive stimulation is what typically gets a woman to orgasm the fastest, but again, communicate with your partner to make sure it’s what she wants.
Once your partner is wet or (best case scenario!) has orgasmed from your oral skills, it’s go time. Be gentle. It’s a myth that vaginas get looser with more sex, so if your partner is more experienced, don’t expect to be able to get it in super quickly. Be delicate, work your way in slowly, and make sure to check in with her verbally to see if everything feels good. If you’re having a hard time inserting yourself, start with fingering: with your palm facing upwards, insert your index finger first, and slowly start making a “come here” motion with it, curling it towards you. You’ll feel a kind of bumpy, rough spot inside her vagina, and that’s what you want to be massaging. Keep doing that, and try inserting your middle finger as well. By then, your partner should be wet and relaxed enough for you to enter her.
And once you’re in…biology is probably going to take over, and your nerves will significantly decrease, because trust me, it’s gonna feel really good. Start out with slow strokes, and just do what feels natural after that.
Make sure to have the logistics of ejaculation all sorted out before you start: having the “where should I cum?” conversation can be kind of awkward. Some women will prefer you finish outside, even if you’re wearing a condom. Make sure you have that knowledge, so if the time comes, you’re prepared and relaxed.
The Big Bang might not be so big
Back to the porn expectations thing: there’s a good possibility you or your partner won’t orgasm the first time you have sex, and that’s completely okay. Knowing your own body gives you a very good chance of being able to cum, but lots of factors can change that: distraction, nerves, or just a random decrease of libido.
Don’t feel pressured to stay hard or ejaculate, and don’t pressure your partner to have an orgasm.
For many women, reaching orgasm can take a pretty long time: for some, more than thirty minutes of clitoral stimulation is necessary. Some women will want you to do that, and some won’t. As we mentioned previously, communication is key: if you feel like you’ve been going on for quite some time with no results, ask her what she’d like you to do. She may just say, “nothing”, and that’ll be a wrap. There’s nothing wrong with that.
Above all, just relax. Humans have been doing this since we first existed. It’s natural, it’s fun, and above all, it should be enjoyable for you and your partner.
It might not work out the first time–in fact, there will probably be some mishaps–so remember to laugh, to shrug things off, and to let your partner know you care about them no matter what weirdness occurs.