21 Things To Know Before Losing Your Gay Virginity

Considering popping the cherry? Read this first.

When it comes to sex, don’t worry about words like “gay,” “queer,” and “bisexual.” You’ll find the word that fits — and it might be none of these. You don’t have to define yourself to the world in order to experience sex between men. If you’re curious, questioning, or interested in sleeping with another man, this is for you.

Sex between men is a beautiful, passionate, awesome thing. It’s also a difficult thing to do when you’re starting off. Do you want to try anal sex? Do you want to kiss, suck, rub, or touch? What do you try first? Where do you begin? How do you keep yourself safe from sexually transmitted infections? These questions and more are covered here.

It’s OK to be scared or nervous. Everyone is. Keep reading for 21 things to know before losing your gay virginity.

1. First things first: Make sure you can easily and safely access medical treatment. That may mean waiting until you’re 18.

This is a fact queer youth have to face: teenagers under the age of 18 do not have any legal ability to hide their medical history from their parents. In the United States, patient privacy laws like HIPPA only apply at legal age. So if you’re in the closet and don’t feel safe coming out to your parents and talking to them about your sex life, wait. Men who have sex with men and transgender women are most at risk for HIV, and have high rates for other sexually transmitted infections too. That fact doesn’t mean you shouldn’t have sex (more on that later). It just means you need to be in a place in life where you can get routine STI testing — men who have sex with men should be tested for HIV and other STIs every 3-6 months, minimum.

It can be very difficult for teenagers to gain access to STI testing and treatment. You may even need your parents to drive you to the doctor. This can create some tough scenarios for young queer people who may not feel safe coming out to their parents.

2. Men who have sex with men are not automatically gay.

If “gay” doesn’t sound right for you, don’t worry — not every man who has sex with men is gay. Some MSM (men who have sex with men) are bisexual. Some are questioning and unsure of what to call themselves. Don’t worry about the words and labels — you’ll find a word that fits you in time when you’re ready. Until then, you’re allowed to experiment and experience sex. You always will be.

3. Being emotionally ready for sex is important too.

You’ve probably learned the ins and outs of being physically ready for sex. But how do you feel about sex? Do you feel ready?

Sex is emotional. Although I was physically ready to start having sex when I did, I wasn’t emotionally ready. I used sex as an outlet to vent my fears and frustrations with my parents, with no thought of what might happen if I caught an STI. The real possibility of having to explain to my religious family what I had been doing never crossed my mind. I was lucky that I never had to face that scenario. Make sure you’re in a good emotional place. This doesn’t mean that you “have everything figured out” and have a clear identity to present to the world. That just means you’re ready to experiment, to start an adventurous journey and see where it goes, and you’re ready to tackle the challenges as they come.

4. Sex between men is not like porn.

I’ve worked in porn, and I believe porn is important. But porn doesn’t teach you how to have sex.  Porn is a cleaned-up, edited, unrealistic fantasy — and that’s what it is supposed to be. Guys with years of experience don’t have sex like that. Even porn stars don’t have sex like that — not in real life.

5. There’s no “right time” to start.

As queer people, we find there’s a lot of stuff we have to work through before we start having sex — stuff that your straight peers don’t face. We don’t develop a sexual language or sexual identity along the same timeline as them. Thanks to a culture that is and always will be hetero-oriented, queer people are often delayed. Many of us wait until we have safe space and medical resources to start having sex. Many of us wait until we leave our parents and have our own places to live — which affords us the privacy and freedom to start experimenting. Many of us wait until we find a community of others like us — potential sex partners included.

6. The first time might not be perfect.

Sex is awkward, especially when you’re new. That’s because you don’t know what you’re doing. The mechanics of sex may feel uncomfortable and painful. Don’t worry, you just need practice. Don’t decide after one bad experience that sex “isn’t for you.” Don’t give up. Just know that you’re a beginner just starting your lessons.

7. You might not be able to start having anal sex immediately.

It might not happen the first time. Anal sex requires a lot of trust and patience when you’re starting off — and a lot of lube. Don’t set the expectation that you’re going to do it successfully on the first attempt. If you don’t, no worries! Foreplay is awesome. Making out, handjobs, sucking, and even gentle kissing and massaging are a great way to start.

8. You do not have to know what you want.

You probably won’t, at least for a little while. Some people come out of the gate thinking they know exactly what they want sexually, but most of us are unsure. You may have watched some porn, you may have seen some hot images, but you don’t know how it translates to your life, or to the people you’re attracted to.

Don’t worry. No one knows what they want in the beginning. You’ll base your desires off what you experience.

9. Heads up: There’s a lot of terminology coming your way. Ask what words mean.

You will be thrown a lot of terminologies, especially if you look for sex with men on hookup apps like Grindr. Words like a top, bottom, versatile, bare, raw, party, safe, poz, neg, cum, daddy, dom, sub, boy, otter, bear, pig. The list goes on and on. If you don’t know what something means, ask. Don’t pretend that you know. If the person you’re talking to refuses to explain or teases you for not knowing, they’re not someone you want to experiment with.

10. Just to get you started, here are a few definitions.

A “top” is the active partner in anal sex. A “bottom” is the receptive partner. These roles define what you’re physically doing in sex — nothing more. A bottom isn’t “the girl.” Bottoms don’t have to be smaller, submissive, or feminine. A top isn’t “the man,” and doesn't have to masculine or dominant. These sex roles don’t define how you behave, how you dress, or how you date, and they have no bearing whatsoever on your worth or your attractiveness. They just define what you’re doing in sex. That’s it.

You don’t have to exclusively enjoy one or the other. In fact, many people are “versatile,” meaning they enjoy both topping and bottoming in the right scenario or with the right partner. You don’t have to know which one you want to try when you’re a beginner. You can (and should) experience both!

11. You’re going to make mistakes.

You’ll trust the wrong people and have less-than-awesome encounters. You’ll probably develop unreciprocated feelings for someone and get your heartbroken. You’ll meet people you thought were great, who turns out not to be great. This is what you’re supposed to be doing right now. You make these mistakes now, learn from them, and are better prepared going forward. Some of them won’t be easy, but they’re the most important lessons on your journey.

12. Don’t make decisions about sex from one or two bad experiences.

Many guys decide bottoming just “isn’t for them” after a couple failed attempts. And many people have messy first-time attempts and decide sex “just isn’t for them.” Don’t jump to conclusions about yourself or about sex from one or two experiences. Your first attempts will not be perfect, and they’re not meant to be. Keep trying.

13. There isn’t a “correct” amount of sex you should have.

Let’s stop slut-shaming before it starts. There’s no “correct” or “healthy” amount of sex one should have. Some people will have a lot of sex — more than you want to have — and that’s totally OK. Some people will have less sex — but that doesn’t make them more “pure” or less “slutty.” That doesn't make them any less “safe” as a sex partner — anyone can have a sexually transmitted infection, even if they’ve only ever had sex once.

The safest sex partners aren’t the ones who’ve had less sex. The safest sex partners are the ones getting regular testing for HIV and other STIs — a minimum of every three to six months — and who are protecting themselves with condoms and PrEP (more on those later).

14. No one needs to know your “number.”

It’s no one’s business how many sex partners you’ve had, or how many sexual experiences you’ve had. When someone asks, you can tell them: “It’s none of your business.” That question is designed to shame and manipulate you. Whatever answer you give will get judged as being too much or too little — so don’t give it. The only person who needs some idea of how much sex you’re having is your doctor — a medical professional you trust.

15. Yes, bottoming might hurt.

Anal penetration might hurt the first time you try it. Your ass has to expand to accommodate a penis, and this stretching can hurt. If you go too fast or don’t use enough lube, you can injure yourself. Going slow and gentle, using plenty of lube, communicating, and taking frequent breaks is how you get better at it.

16. Yes, sex might be messy.

If you’re having anal sex, you might get messy. Don’t freak out or call yourself a “failure.” You’re not a failure. That’s just what the body does. If you want to research different methods of cleaning men who have sex with men do, go for it. Many guys douche before sex, but douching is not a requirement to have a good experience.

You can use water to clean your butt (specifically, the lower part of your rectum, the space just inside your hole) with a drugstore enema or handheld bulb. Remember: If you buy a drugstore enema, many of them are filled with laxatives, which you should empty out and replace with water before you use them. You don’t have to use all the water, and you need to go slow. Going too fast or too rough can be painful (I recommend a thick, silicone-based lube for the insertion tip). Also, make sure you try to release all the water into the toilet — leftover water stuck in your butt can cause discomfort later on. When your butt is filled with water, wait a few seconds, then release it into the toilet. Repeat as necessary until the water is clear. And I can’t stress this enough: Be gentle, and go slow!

Again, not every guy douches before sex. A healthy, fibre-rich diet (lots of veggies, less meat) eliminates the need to douche for some. Others just don’t worry about it — they have fun and clean up after.

17. If you choose to douche, don’t douche too much.

Different medical experts agree that you shouldn’t over-douche. This means you shouldn’t douche every day, or for very long. Don’t douche for hours. If it’s not working and you don’t want to have sex unless the water runs clear, skip the anal sex and stick to foreplay (massage, kissing, sucking, and so on). Douching should be minimal. Seriously: A fibre-rich diet, or a daily fibre supplement like Metamucil, will minimize how much time you spend in the shower or on a toilet.

18. Yes, you do need to take sexually transmitted infections seriously.

All sexually active people do. Having any sex puts you at risk for HIV, syphilis, gonorrhoea, chlamydia, and other sexually transmitted infections, or STIs. Thankfully there are many ways you can protect yourself.

PrEP is the once-a-day dosage of a pill you can take to prevent HIV infection. The only drug approved for PrEP is Truvada, but more are on the way. PrEP requires good health insurance and an understanding doctor who is aware of your health needs. For various reasons, PrEP is difficult for many to get access to, but if you have a doctor you trust and reliable insurance, it’s a good idea to ask them about it. PrEP can keep you HIV-negative.

Even after you go to college or move away from your parents, you may still be on their insurance, which means that they still see bills from the insurance company. If you’re seeking treatment but don’t know what options are available to you, many clinics — especially clinics accustomed to treating and working with men who have sex with men — have social workers who can help you navigate your options and decide what course of action is best. Before seeing a doctor, always check and sign your patient confidentiality form.

Whatever you do, it’s worth the extra work to locate a doctor or a clinic that specializes in working with men who have sex with men, HIV testing and treatment, and LGBT health. You don’t have to identify as “gay,” “bi,” or anything to receive treatment.

Along with PrEP, condoms are also incredibly effective at preventing STIs like chlamydia, syphilis, and gonorrhoea. Put these two together — PrEP and condoms — and you’re as safe as you can be from the most troublesome STIs.

Other, less severe STIs, like oral and genital herpes and HPV, are so common that most sexually active people are at high risk of catching them. In most cases, their symptoms are mild or nonexistent. The best thing you can do to protect yourself has a doctor who you trust, who performs regular checkups. If you have any symptoms, or experience anything on your body that may or may not be related to an STI, always tell your doctor about them.

19. Get the three-part Gardasil vaccine. It’s important.

Regardless of how much sex you’ve had — and especially if you’ve had none — it’s a wise idea to get the three-part Gardasil vaccine for HPV. For people with no sexual history, Gardasil vaccinates you against strains of HPV most commonly associated with certain types of cancer. For those with a sexual history, the Gardasil vaccine is still recommended, since it may still be able to fight future strains of cancer-related HPV.

20. Sexually transmitted infections may be scary, but they’re not worth abstaining from sex.

Most sexually active adults get an STI at some point. You probably will. I’ve had several. This isn’t a sign of being irresponsible or reckless or disgusting. It’s just part of being an adult in the real world.

The wonderful benefits of sex far outweigh the risk of STIs. A common STI like chlamydia might require you to stop having sex for a week or two while the medicine clears it up. But a lifetime without sex means a lifetime without the awesome, beautiful, wonderful, sexy people you get to share your world and your bed with — people who will make you feel strong and beautiful and powerful. They’re worth it.

21. Sex gets better.

I promise. I didn’t advance to the point of really loving sex until I was in my mid-20s. In most of my early years, I felt frustrated, inhibited and unsure of what I was doing. Sometimes I still do. When the day comes that you feel confident in your skills, you’ll be grateful for all the messy early attempts. They taught you how to get better.

@advocate.com