Since my advice is intended to help you get more dates, and dating leads to sex, I feel a moral imperative to mention something.

Specifically, that you should accept Jesus Christ into your life and start practicing celibacy.

Just kidding.

That would be quite the twist.

But seriously, before we get into things, I have to tell you to be cautious when having sex.

Go ahead…roll your eyes at me like you do when your parents say “be careful.”

But then listen up, because sex is an adult activity, with legitimate consequences, and I don’t want you to make the same mistakes I did the first time I had sex. Here’s what happened:

I met a girl on OkCupid, picked her up for a “date”, and we agreed to go straight back to my place. I barely knew anything about her, and our conversation on the drive was incredibly boring (she seemed a little out there). But it didn’t matter, because all I was thinking was I’m finally going to get laid!

I tried being on top of her (because I believed that was the only way to do “it”) and she kept getting frustrated, because I couldn’t support my own weight for very long, and I would end up kind of falling on top of her.

We switched positions, but then I was having trouble staying inside of her, BECAUSE MY DICK IS SO HUGE.

Nah, I was having trouble staying hard. Because I was really not having a good time.

As a last resort, I asked her to give me a blowjob. And she said she would, for 75 dollars.

To be honest, I seriously considered it, because at that point, I hadn’t even been on a real date. And I thought I might never be intimate with a woman again.

But I said no, because it didn’t feel right. I dropped her home, and I cried myself to sleep that night.

So yeah, I lost my virginity, but at what cost?

Looking back, this was a very risky situation. This able-bodied woman, who I barely knew, was in my home, with nobody else there. Any number of harmful things could have happened. Plus, I knew nothing of her sexual history. I used a condom, and my STI test results came back clean, but I remember being deathly afraid, because on the drive back, she told me she lived in a transitional homeless facility.

When you don’t have a lot of dating experience, it’s easy to throw safety concerns out the window. But as they say, you will always remember your first.

Here’s how to make it a better memory than mine, broken down into 3 steps.

1. Sexual Consent

What is sexual consent?

Sexual consent is actively agreeing to sexual activity. There are multiple aspects to this (check out this excellent Planned Parenthood article/video) and I believe the two most important are:

The person is capable of consent – someone who is intoxicated or underage is not legally capable of consent, no matter what they say. It is YOUR responsibility to be aware of the laws in your area and abide by them. When in doubt, don’t do it – it’s just not worth the risk of being accused of rape/sexual assault. The person is enthusiastic about consent – meaning they are doing it because they want to, not because they feel pressured to or afraid of what might happen if they don’t.

I’ve always been a proponent of consent, because, yes, I don’t have the physical ability to force someone into sexual activity, and also because sex is just not fun without it.

I once asked an ex-girlfriend to go down on me when we were in the shower together, and she asked, “do I have to?” which made me feel so icky. I said no, because what makes sex enjoyable is knowing that your partner enjoys receiving and giving pleasure. If they are not excited about getting you off, the sex is honestly just not that good.

Side note: not all requests for blowjobs end terribly, despite the evidence I have presented thus far – stay tuned for the better stories :)

2. Sexual Health

One of the very real consequences of having sex is STIs, or sexually transmitted infections. If you were fortunate to grow up in a place where they taught you about sexual health, you probably learned the basic premise that you should use condoms & get tested, but that was kind of…it.

Nobody really talks about how to practice safe sex.

The best people to consult about practicing safe sex are polyamorous people, because they have a LOT of it. Safe sex, I mean…

Fortunately, I dated a polyamorous girl who sparked the desire within me to become a more conscious sexually active person. Note: I am by no means an expert, and I’m constantly learning from others, like this courageous woman who is decreasing the stigma around herpes.

Here are some common sense things you should do to reduce your risk of contracting STI’s:

Always use a barrier to prevent genital fluid exchange – the most obvious case is vaginal (penis to vagina) sex, but it also applies to oral and anal sex, which people often forget/neglect. Always use a condom or dental dam. If you haven’t had sex, buy condoms and practice using them – the first time should not be when you are having sex. It’s also helpful to practice using lube. Get tested for STIs before and after each partner, and then just regularly (as part of your annual checkup). Keep a copy of your STI test results handy, share them with her, and ask to see hers. Yes, this means you should get tested even if you are a virgin, so you’re not asking her to do anything that you are not ready to do. Most importantly, talk to your partner about sexual health, before you have sex. Ask her if she’s been tested, when she last had sex (it can take up to 3 months after exposure for STIs to show up), whether it was protected or unprotected, etc.

You’re usually going to have to have this conversation when it’s obvious that you both want to have sex with each other – and that’s pretty difficult, because things are going to be hot and heavy. And you might think that this will kill the vibe, but trust me, it won’t.

Not only is having this conversation part of practicing good sexual health, it’s also going to make her SO HOT for you. Because most guys can’t WAIT to jump into bed with her, and here you are, taking your time, and making sure both of you are being safe & responsible. Women LOVE this, like you won’t believe.

The real challenge is going to be waiting, if she hasn’t been tested or doesn’t have her STI results on her. For example, last weekend I was with a girl who was kissing my neck as she whispered I can’t wait to get those test results so I can have you inside me.

Holy fuck dude – I definitely considered throwing all these concerns out the window…

Fortunately, there are lots of other less risky ways to get sexual pleasure, like stimulating your partner’s genitals with your hands, using sex toys, and dry humping (a.k.a. grinding) with clothes on, so we still had a great time.

3. Birth Control

Sex is how babies are made, FYI.

Here are some more dramatic oversimplifications:

Every month, a woman goes through a process called the menstrual cycle, where one of the eggs in her ovaries is ready to become a baby – all it needs is sperm (usually from a man’s ejaculate/jizz/sticky white stuff).

The most well-known part of this process is menstruation, a.k.a. “getting her period,” where she bleeds out of her vagina.

Shut up, dude. I’m just making sure we are all on the same page.

Also, NEVER make a woman feel that in her period is gross. It’s a beautiful part of being a woman, and you should love her for it. More on this later…

Less well-known parts of this process are:

It’s a process, meaning it’s not just a one-day affair that happens once a month (my sister promptly told me I’m an idiot for thinking that). Women experience bleeding, and the associated pain/cramps, for 3-8 days of their cycle (which is often shorter than a month). As a result, they are in a state of intense physical discomfort for about 25% of their lives. Yeah dude, they are fucking strong human beings, because we would be whining about that shit ALL DAY. Women are typically most fertile (a.k.a. capable of pregnancy) around the middle of their cycle. So if her periods are 4 weeks apart, she is most fertile during week 2 & 3 of her cycle (roughly). If her period is “late,” she might have gotten pregnant, because women do not have periods when they are pregnant.

All this is to say – if you have sex without protection, there’s a decent chance you’ll get a girl pregnant.

Which means…you could unexpectedly become a father, and you wouldn’t have much say about it. Once a girl is pregnant, the choice of whether or not to keep the child is ENTIRELY hers.

I’ve had friends who have had pregnancy scares – meaning that the girl they were casually having sex with told them she was “late.” It’s really not a fun time, especially if you are not prepared to be a father, or if you don’t want to be a father with the girl you had sex with.

So here are some common sense things you can do to prevent this:

Ask her what she would do in the case of an accidental pregnancy, but do not rely on her answer – remember that you have ZERO control of her decision in that situation. Plus, her body will be releasing hormones designed to protect the child growing inside of her, and she may change her answer. Familiarize yourself with the various types of birth control, and ask her which one she is on. Use multiple forms of birth control – using condoms correctly is really the bare minimum here, because they are not 100% effective. Make sure she is on some form of birth control as well.

Okay, you can relax now…the intense warnings are out of the way.

Look, I’m not trying to dissuade you from having sex – I’m just trying to convey to you that sex is an adult activity, with adult consequences. Everyone is all anxious about getting some (especially getting their first) and they just don’t think this shit through.

If you have sex, you can get arrested for violating consent (and be a registered sex offender for the rest of your life), you can contract an STI, and you can end up with an unwanted child.

It’s intense!

But once you handle all this shit, and you are both ready to go, you can experience IN SANE amounts of pleasure, without having to worry about what happens after.

Don’t you want that?

I certainly do, and it’s how I’ve explored some AMAZING fantasies, like having a girl greet me at my door in nothing but her panties, or giving/receiving extreme amounts of pain during sex, or even role-playing as if I am “raping” my partner.

Crazy, right?

To do all this, I constantly observe the girl I’m having sex with – does she seem comfortable, happy, excited about continuing? If I’m unsure, I ask.

I also ask her to show me her STI papers before having sex. I get into the gritty details of her sex life, because my consent matters, too. And I prefer to be informed.

To prevent pregnancies, I got a vasectomy (a.k.a. I got “snipped”) because I don’t plan to ever have children, and even if I did, I wouldn’t do it naturally, as the odds of my child having muscular dystrophy is 75%. I froze my sperm in case I change my mind in the future, so I can pursue artificial insemination methods (which would not pass on my condition).

And I STILL talk to my partners about what they would do if they got pregnant – I don’t really have to worry about pregnancies now, but I still like the question, because it gives me a sense of her life philosophy, and whether or not it aligns with mine.

You certainly don’t have to go as far as I did in this area (and snip your balls…ouch, that shit HURTS) but you do need to be aware, my dude.

I wish someone would have talked to me about these things, instead of rushing me towards just “getting it over with”. I was fortunate to be raised near Chicago, in a fairly liberal town, where sex education was taught in school, but that was…it.

My parents didn’t talk to me about this, my friends didn’t talk to me about this, and not even my dating coach talked to me about this! And that’s just irresponsible…

So here’s to reversing that trend. Let’s all talk about this more.

And that’s the ultimate lesson here – be sure to talk to your partner about these things; your little D will thank you for it ;)