Your First Time: A Sexual Guide for Cis Boys

A person with their head on a pillow, gazing thoughtfully into the distance.

A person with their head on a pillow, gazing thoughtfully into the distance. Source: Getty

Editor’s Note:This article was written with the goal of helping young cisgender men work through how patriarchy has affected their understanding of their bodies, their partners, and their sexual experiences. Oftentimes, this piece takes on a heterocentric framework as well. At Everyday Feminism, we are tirelessly dedicated to inclusive, intersectional feminism and in no way mean to imply that only cisgender, heterosexual men struggle with sexuality; rather, this piece serves as a jumping off point, starting with answering the questions that we most often find in our inbox.

Let’s face it: Most sexuality education is terrible.

If you’ve received a formal sex education, it likely went a little like this:

Sex is a special covenant between a man and a woman. Here’s a little information about the biology of sexual intercourse between a man and a woman. And here are a bunch of horrifying pictures of STI’s that will scare you into remaining abstinent until marriage.”

And we think that it’s time we change that.

Sex ed has to change.

Because if we don’t do a better job of teaching healthy sexuality, we leave it up to pornography, television, music, and movies to do our job – and none of those are accurate, comprehensive sources of sexuality education.

It’s time we teach our young people about more than just biology, STI’s, and abstinence.

It’s time we teach about how to have amazing, fulfilling, consensual, and healthy sex.

Cynthia Kane already wrote a fantastic guide for having great sex on the first time, but since some of the most effective sexual education is split up by gender, the brilliant Melissa A. Fabello and I are here with a two-part article to amplify Cynthia’s message.

And since I identify as a man, I will start things off by talking to the boys and men out there.

That said, let me be clear that I am a cisgender man, and as such, many of these lessons come from a cisgender perspective and should be treated as limited in that way.

So what are some steps to take before diving into sex for the first time? What are some important facts to know? And why are they important?

Let’s take a look.

1. Get to Know Your Body

Amazing sex starts with you knowing a bit about your body and what you want and need from your partner. So before you head into the bedroom with another person, you need to spend some time by yourself.

Yup. I’m telling you to masturbate.

But I don’t mean the “jerk off quickly in the bathroom before someone catches me” kind of masturbation.

I mean taking your time, exploring your whole body, figuring out what does (and doesn’t!) feel good.

How do you like to be touched, where do you like to be touched, and in what ways do you like to be touched?

More and more, young women are being told to familiarize themselves with their bodies (which they should!), but young men aren’t being told the same thing.

The idea that a man would take the time to light some candles, draw a bath, and explore his body for maximum masturbatory pleasure is considered laughable. Let’s change that!

Too often, we just treat male pleasure and orgasm as being easy. Having fulfilling sex, though, means having a much more comprehensive knowledge about your own pleasure.

Did you know that one of the most powerful orgasms a man can have has virtually nothing to do with his penis?

It’s called a prostate orgasm, and most men never experience this tremendous joy because of the taboo around anal play being “gay” and thus “terrible and disgusting and eww.”

Whether it’s a prostate orgasm or neck kissing, you won’t know what works best for you, though, if you never take the time to explore.

2. Interrogate Your Media Consumption and Expectations

Long before anyone tried to talk to me about sex, bodies, or relationships, I learned about those things from porn.

I was introduced to pornography at a very young age, and before that, I got plenty of confusing and misleading messages from TV or movies.

Now, both men and women get taught misinformation (which can sometimes be damaging) from media in general and porn specifically, but dudes, it’s time we unpack some of what we’re taught.

First, you don’t have to be in charge.

Rarely in any media do we see women who are taking the lead in sex. Nowhere is this more evident than in porn, where women are almost never seen taking charge – except in fetish porn where women are explicitly dominant.

Instead, sex should be a conversation (more on that later) where both people are communicating and asserting their needs and desires.

Second, your partner may not want your semen all over them.

There are some people who are totally down with facials (or semen anywhere for that matter) and find them hot, but porn makes it seem like every person wants your ejaculate all over them at all times. And it’s not true.

In fact, a lot of people find things like facials to be degrading expressions of dominance and control.

Thus, before you go shooting your spunk, you may want to chat with your partner about things like condom use (see below) and where that sticky stuff is (and isn’t) welcome.

Third, no one is owed anything in sex.

One of the most powerful media messages that men receive is that we are owed pleasure and gratification and access to others’ bodies.

If all we knew of sex came from porn or mainstream media, we’d assume that men must orgasm for sex to be sex and that all bodies exist for the sole purpose of pleasing men.

Not only is that selfish (and boring), but it’s downright misogynistic.

Instead, think of your pleasure as wrapped up in the consent and pleasure of your partner!

Sex will be more fun and fulfilling that way.

Finally, sex is about more than orgasms and penetration.

If there’s any clear message from media, it’s that sex is about the dude putting his penis in any given orifice, and when he reaches orgasm, sex is over.

On the contrary, though, sex is about connecting with another human being on a number of levels, and if you’re only focused on either getting or giving an orgasm, you’re going to miss out on big parts of that connection.

Be present. Realize that sometimes the best pleasure comes before or after orgasm and that there are countless ways to experience sexual pleasure.

Want some more information about pornography and media literacy? Check out these awesome resources:

3. Protection and Prevention of STI’s

Now, I know that I started this piece by criticizing the fear-based education that focuses on STI’s.

But that doesn’t mean that some attention to STI’s isn’t important. They are a reality. At best, they are an uncomfortable inconvenience, and at worst, they are deadly.

As men, something you’re probably used to hearing about are condoms, but they are only a small part of the prevention and protection picture.

Long before ever putting on a condom, prevention begins in talking with your partner about your health status.

One great way to do that is to say, “Hey, I would love to get tested before we are sexually active. Would you like to go get tested together?”

Getting tested does not mean that you’re dirty or that you have reason to believe you have an STI!

Quite the opposite.

It’s preventative medicine.

Just like you get a physical once a year or a dental checkup, getting STI tested is important if you’ve been sexually active.

From there, it’s important to think about protection.

You’ve probably heard, “Use a condom.”

But you’ve probably never heard, “Make sure to measure your penis so you find the best fit!”

Fit is vital to ensure pleasure and safety, so make sure you know which size to buy. Also, remember that there are about a million types of condoms. So experiment a little!

Know, though, that using a condom when having intercourse is not the only type of protection that you should be using.

Very few people use protection during oral sex, but there is a risk of STI contraction from oral. So make sure you pick up some flavored condoms and dental dams (not sure what a dental dam is? Look here!).

Finally, if you’re having straight intercourse, it’s important to talk about pregnancy prevention.

If your partner wants to use birth control, consider splitting the cost (since it’s possible for birth control to get expensive), and make sure that you’re consistent.

4. Sexual Communication Is Key

More than any other factor, good sex comes from one thing: communication.

And that’s a problem for men because we’re socialized to believe that we’re bad at communication and that “talking” through things that are important to us is feminine.

But if you want amazing sex, you need to start talking with your partner. And that conversation likely needs to start before you’ve even touched one another.

Ideally, your first time is happening in the context of a healthy, communicative relationship. So sit down with your partner and talk about what you both want from your sexual relationship.

Are you on the same page with “taking the next step” sexually, whatever that step may be?

Perhaps you should both fill out a “Yes, No, Maybe Chart” and discuss your responses with each other.

I promise it will only be awkward if you decide ahead of time that it’s going to be awkward.

On the contrary, if you take the time to talk through things before taking the next step, your sex will be much more amazing for the both of you.

But don’t think the communication should end there.

5. Expectations for the Big Moment

I don’t know about you, but when I was thinking about my first time having sex, one thing I wasn’t thinking a lot about was how I would communicate with my partner.

But the single most important aspect of sex is also one of the least talked about: consent.

When many of us hear the term, we think of some stiff, cardboard interaction with another person: “May I put my hand on your arm now, please?” “Yes you may!” “Now may I lean closer?” Yes you may!”

But I am here to tell you: active, enthusiastic consent has the power to be the single sexiest part of your sexual experiences if you do it right.

To do that, first you need to get rid of the idea that consent is a one-time, blanket permission or that silence or non-affirmation is consent. Thinking of consent this way is not only a huge turnoff, but it is downright dangerous, and it’s time that we, as dudes, change this perception.

Instead, think of consent as a constant conversation in words, expressions, games, sensuality, looks, bodies. Need some ideas on what that means? Check out “Want the Best Sex of Your Life? Just Ask!

Plain and simple: Sex that is built upon the constant communication of enthusiastic consent is guaranteed to be the most incredible sex that two (or more!) human beings are capable of having.

Aside from a better knowledge of consent, here are a few other things I wish I had been told about the deed before the first time I had sex:

It’s okay to ask for things that you want/need! In fact, unless your partner is a mind reader, if you are going to have amazing sex, you need to! But you also have to be willing to listen when your partner does the same.

If you reach orgasm really quickly, don’t worry! That doesn’t mean that sex has to be over! Explore some other ways to give and receive pleasure. There is no prescribed time in which you’re supposed to ejaculate.

Having a hard time orgasming? That’s also okay! Talk to your partner about what each of you need to feel more pleasure next time, and take some time exploring each other’s bodies! Oh, and “blue balls” is very rare, and it should not be used as an excuse to pressure someone into giving you an orgasm. “I really want to cum” and “I am experiencing a rare medical condition characterized by sharp, acute pain in my testicles” are not the same thing.

Great sex comes from listening. If something feels amazing and they arch toward you, remember that. If something’s not doing it for them, maybe they won’t tell you for fear of embarrassing you or themselves, but their body likely will. Then you can ask! “I noticed you started breathing REALLY heavily when I did such-and-such. Should I do more of that?” or “I noticed you weren’t really into blah-blah-blah. Was I reading you right?”

Men Need to Talk to Men and Boys

It’s time that men start having more accountable conversations with men and boys about healthy, positive sexuality.

It is our responsibility to raise a generation of men who are committed to ending sexual violence, and a great place for us to start is by building the healthiest sexual relationships that we can.

So if you have suggestions about what else men and boys need to hear to have amazing first time sex, share them in the comment.

Are you a dad or a big brother or a mentor? Give this article to the young men in your life and chat with them about it!

Jamie Utt is a Contributing Writer at Everyday Feminism. Jamie is a diversity and inclusion consultant and sexual violence prevention educator based in Minneapolis, MN. He lives with his loving partner and his funtastic dog. He blogs weekly at Change from Within. Learn more about his work at his website here and follow him on Twitter @utt_jamie. Read his articles here and book him for speaking engagements here.