First-Time Sex: Making It Pain-Free & Enjoyable

Hi Aunt Vadge,

I’m ready to have sex with my girlfriend. We are both 14, and I don’t want to hurt her that bad. Will she be in intense pain after I insert my penis? I need some advice.

Sincerely,
Curious
_____

Dear Curious,

You could benefit from looking at this a different way. Instead of trying to minimise the pain your girlfriend feels when you put your penis into her vagina, think about it more along the lines of is my girlfriend ready for sex too? (just because you’re ready, doesn’t mean she is), and how do I make this really great for my girlfriend (and not hurt her at all)?

Girls are led to believe that first sex is meant to hurt, but with a bit of preparation and understanding about what it is you are trying to achieve, first sex can be fun, awkward, and maybe a bit uncomfortable as you both adjust to the sensations of one person being physically inside the other person, but not painful.

Sex should always feel good, and if it doesn’t feel good, you’re doing something wrong and you need to stop and rethink it. First sex is a bumbly affair at the best of times, so preparing yourself as much as you both can means better sex sooner. This is your fast track (while taking it slow) to being a great lover.

As well as this article, read Sex 101, Fingering Basics for Men, and How to Perform Cunnilingus. You will need all these skills.

So let’s talk about the first thing: is my girlfriend ready for sex too?

This is really important, and will make the difference between you hurting your girlfriend and her having a good, awkward, fun, maybe-a-bit-uncomfortable-and-weird time. First sex is not going to blow anyone’s mind, but it should also not be something that guys get to look forward to and girls think of with horror.

(Which is how it works – guys are generally not afraid of intense pain upon sex, but think of it with a sense of excitement and nervousness).

Looking at this from her perspective will give you insights into how to deal with your first – and all – sex, now and for the rest of your life. Sex with a new person – your girlfriend and all your other girlfriends – is not really just about putting your penis in her vagina and pumping away until you come.

That’s what it looks like to girls, and many girls are kinda scared about sex, because it never looks that much fun for us, especially at first. You need to convince your girlfriend that you know better, and offer her a reason to believe that you are not going to hurt her vagina with your big stiff stabby penis. The following information is how you will learn how to do that.

Sex is meant to be fun for everyone, so your job is to make sure your girlfriend is always having a good time and vice versa. It works both ways, but it’s true that you are going to have to work much harder for her to have a good time at first. This is because the basics of the woman and the vagina are less obvious, and easy to screw up if you don’t know what you’re doing. That is, you are very well versed in the behaviour of your penis, but she is more likely to be less comfortable with how to get herself off and navigate her own vagina.

You have a bit of reading to do before you have any sex, or put anything inside your girlfriend’s vagina, so put sex off the table for the time being while you learn – I promise, it will be way better than if you dive in unprepared.

If you want to be remembered for all of time as a fantastic lover, take some time to carefully read through the articles I’m going to recommend to you. Don’t skim read. Take your time. Take notes. You have asked a huge question that doesn’t have a simple answer, but it does have an answer.

I recommend that your girlfriend also reads all of this stuff too, because having sex well is not a one-way street – it is about learning about each other and figuring out how your bodies work. You will both learn how to offer each other useful feedback, so you can get to the good stuff faster (which is what we all want).

Here are your tasks:

She needs to figure out her hymen (this is not your job)

You both possibly have the hymen to deal with, which is the first problem you may encounter. Read this article about the humble hymen, and if it does exist, how your girlfriend can gently stretch it out with her fingers – not brutally pop it with your erect penis – over the course of a few weeks. This gently opens up the vaginal entrance so that you don’t have to push through the hymenal membrane, which can be very painful (the hymen has a blood and nerve supply) and cause bleeding, anxiety, and fear.

The fear of this hymen pain can be intense, and cause your girlfriend to clam up in advance. Unless you do these exercises, she will feel that fear. Her feeling more secure because she has done something proactive to avoid that particular pain will be reassuring to her.

Turn her on: start touching and oral sex and whispering sweet nothings

Before you get into actual sex, you need to learn how to pleasurably finger and go down on your girlfriend – you need to learn how to turn her on. If you imagine that the female sexual system is just like yours, except the tissue that gets a boner is inside of her body. This is true, which you will see with the diagrams of the clitoris in the articles I’ve recommended, which is actually enormous.

When she gets turned on, she gets an internal boner that is really just like yours, but you only have clues to whether she’s turned on (including her telling you). If she does not have an internal boner when you put anything inside her vagina, it will feel soooo boring and be a waste of time.

A vagina must have its internal boner, just like you need a boner, to have any sex at all that feels good. Don’t forget this. It’s the most important thing you will learn about good sex. (Never, ever just put your penis into a vagina because it’s there. Her vagina must have a boner or it’s like shoving your fingers into someone’s mouth and expecting them to like it.)

Investigating her body this way is far less scary and far more educational than getting straight into the p-in-v sex, especially for her – you are increasing pleasure and trust, thus reducing anxiety, therefore reducing tension, thus reducing risk of pain – got it?

Read Fingering Basics for Men and How to go down on a woman. You need to know this if you want to be the lover that your girlfriends remember with lust. Making a girl come using your mouth and/or fingers is a skill worth having in this life, where it doesn’t matter how good looking you are, what car you drive, how big your dick is, or how much money you make: women love this. This girlfriend you have right now is where you get your lusty learner licence – make every moment count.

Learn how to have sex well by understanding what it is your are trying to achieve (besides your own ejaculation)

You both need to read Sex 101. This goes through diagrams, vaginal anatomy, internal boners, how to talk about what you’re both feeling during sex so you’re not doing weird stuff and not knowing about it, and how to make sex better.

The only way you and your girlfriend can have good sex is by going slow and making sure all the boxes are ticked, so to speak. Sex should never hurt, ever ever ever, and if it does, you’re doing it wrong. Yes, it is sometimes uncomfortable, but that should always be remedied immediately by changing what you’re doing.

The first time you guys have sex, your girlfriend is probably going to be worried about pain, but if you have done your preparations and trust-and-lust-building exercises, she will feel way more relaxed about it. Her being relaxed is important for her vaginal muscles to not be clenched tightly shut, and cause her intense pain. She wants to be reassured that you are not going to hurt her, ever, at all, in the vagina.

Go slow, be absolutely gentle, and earn her body’s trust by being attentive, kind, and patient. (And of course sensuous and lusty.)

You need to talk about contraception NOW

You need to have this conversation before you have any sex at all, and you need to understand how you get a woman pregnant and what you need to do to stop it (without making sex bad). You should be learning how to use condoms with your girlfriend, so make sure you have plenty of good-quality thin condoms (yes, you will need to buy good, thinner ones for better sensation and they are annoyingly expensive!) but make sure you also get a good water-based lubricant like KY Jelly.

Read about condoms here and practice putting them on when you are not in the middle of having sex. Get good at it. Women respect men who respect their bodies by not being loosey goosey with germs. STDs are gross.

Condoms dry the vagina out, and can rip or really cause horrible pains to the vagina if you don’t have lube. Buy lube and learn how to use it wisely. It’s great stuff and it’s not a sign that things aren’t good – it’s the sign of a person who knows how to use condoms properly.

A dry condom is your greatest enemy and saliva only goes so far. Don’t use Vaseline or oil – oil degrades condoms – and avoid moisturiser, as it isn’t vagina-friendly. Never have dry sex with a condom on – it’s really quite painful afterwards when the vaginal burning and stinging starts.

Your girlfriend needs to make sure she has a period tracker so she knows when she is ovulating (and her fertile days, so any accidents can be remedied with the morning after pill/emergency contraception).

You should also plan your sex play when she is more likely to be in between periods, since around her period, especially towards the end and immediately afterwards, she is more likely to be disinterested in sex, and trying to get her turned on will likely be kind of a waste of time.

It doesn’t mean it can’t be fun, but her body just isn’t geared up for sex during some parts of the month. Everyone’s a bit different here, so you guys will need to learn this together. Just remember this though, when she isn’t responding the same to you. It’s not necessarily you; it could be her natural cycle. I suggest you learn it and work with it.

Your girlfriend should investigate different kinds of birth control, and find the one that’s right for her. The ‘main’ ones are not necessarily the best, for example hormonal birth control like the pill can have the unintended consequence of causing women to lose their sex drive, while others like the injection have terrible reputations for making women fat and crazy. Not ideal!

It may work for her, but condoms are a safe bet while you are learning how to have sex. Learn about how semen and precum work here, and you should both put some effort into learning about her cycle and how to avoid getting pregnant. If you are both free of STIs, there is no reason why you can’t learn about her fertility cycles over time to the point where you don’t always have to use condoms. This is advanced sex, so don’t try this yet!

Learning about sex is a lifetime activity, and getting the p-in-v action is really the least of it. Making sex awesome, at least most of the time, is what you’re aiming for, then learning from the not-so-awesome times how to do better next time.

Good luck and write anytime!

Warmest regards,
Aunt Vadge