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On having (straight, penetrative) sex for the first time, Part 2

Hello my darlings, and welcome to part two of the cool aunt project’s Guide to Having Sex for the First Time!

Everyone excited?


So, last time we covered the pre-sex stuff; essentially, how to make the decision to have sex. In this post we’ll cover the physical stuff, and the actual dreaded dead. School is in session darlings!

You will need:

  1. A consenting and respectful partner.
  2. A good place to have sex. Beds are good, cars are not. Trust CA on this one; you definitely want your first time to be in a comfortable safe place.
  3. Lube (more on this later).

You will not need:

Candles, silly lingerie, ridiculously intricate sex positions (for the first time, your best bet is either him on top or you on top, but nothing super fancy), anything else you may have seen in pop culture. Keep your first time simple, there’s plenty of time to experiment later.

Now that we have covered that, on to the main event, as it were.

First: before you get to the sex part, it SUPER SUPER IMPORTANT that you discuss what kind of protection you’re going to use. If you are on the pill and both you and your partner are virgins, you can just go for it. However, if this is not the case, you MUST use a condom. No exceptions or negotiations on this one. Go to a drugstore and buy yourself a box of condoms. You don’t need anything super exciting or complicated, just basic condoms. I know they’re embarrassing to buy, but think how much more embarrassing it would be to have to tell your parents that you got pregnant. Have your partner practice putting one on when he masturbates, to make sure that he knows how it works and so he can practice when he’s not in the heat of moment. You can even help him practice putting them on one time BEFORE you have sex, so you know how the process works. (Also, if your partner whines about not wanting to use condoms, you should probably not be having sex with him).

One of the most common questions about having sex for the first time is “Will it hurt?”. This is a good question, to which unfortunately there is not one answer, because everyone’s bodies are different. If you have not previously broken your hymen by putting in a tampon or riding horses or bikes or doing something else, the answer is yes, it will probably hurt at least a little bit. I promise promise promise it’s worth it though, and I’m going to tell you some ways to make it less painful, which unfortunately the world generally doesn’t tell girls, even though they absolutely should.

Ways to make your first time less painful:

  1. Lube. This is possibly the most important thing you can do to make everything more fun the first time you have sex, but almost no one tells teenagers about it because society likes to pretend teenagers NEVER HAVE SEX EVER. Because you are likely to be nervous your first time, you will probably be less lubricated than you would otherwise be having other kinds of sex/fooling around. This means what when he tries to put his penis in, it will rub and even chafe, which makes your muscles tense and makes everything miserable. The solution is lube. It’s sold at pretty much every drug store, there is no age limit on buying it, is not expensive, and it makes a HUGE difference the first time you have sex. I know it can be embarrassing to buy stuff like this (see condoms, above) but it is really really worth it. Also, like talking to your partner about sex before you have it; if you’re not mature enough to do this, you should not be having sex.
  2. Relaxing your pelvic floor. Much of what can make your first time very painful as opposed to just a little uncomfortable is that you are not fully physically relaxed. When you’re worrying about how much breaking your hymen is going to hurt, you unconsciously clench all the muscles in your pelvic floor, which makes your vaginal opening smaller, and makes the whole process hurt way more than it should or has to. Thankfully, you have control over this one. What you need to do is practice doing this when you’re not in a sexual situation. Put your finger right at your vaginal opening or right inside it, and practice the feeling of relaxing all the muscles around it. Picture your pelvic floor (the muscles right underneath your vagina) dropping beneath your finger, and everything down there getting wider and more open. It can be a little tough at first because you’re not used to controlling those muscles consciously, but with a little practice, you’ll be able to make them relax even when you’re anxious and excited about having sex. This will really make all the difference to having sex.
  3. Have an orgasm first. Assuming you are not the kind of person who gets super sleepy after you come once (in which case, just have lots of foreplay), having one orgasm BEFORE sex will make you more relaxed and more comfortable. Also, lots of women don’t come from penetrative sex, especially their first time, so it’s a good way of making sure you have positive associations with the process. If you do get sleepy after you come, make sure you have an orgasm after you have the actual sex, for the same reasons. Plus, orgasms are always good.

These are the key elements to making your first time as fun as possible. Above everything¬† else, do what makes YOU comfortable. Stop, start again, decide to do it later, change positions, do hours of foreplay, whatever. It is totally up to you, because it is your body. Have fun and be safe y’all.

If despite my excellent counsel you still have questions, feel free to leave them in the comments or message me! Have a good first time story or advice I forgot? Put it in the comments!


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On having (straight, penetrative) sex for the first time, Part 1

So, this is my first post and it is going to be a long one, because there are lots of issues to cover. Part I of the official “Cool Aunt Having Sex for the First Time Guide” will deal with whether or not you are ready to have sex. Part II will¬† deal with the actual physicality of having penetrative sex for the first time, including use of contraceptives and how to have to most fun and be the most comfortable! But before we even get to the part of having sex, I want to establish the following principles:

  1. Having sex is not “right” or “wrong”. It is a very individual and personal decision, and whether you decide to wait until you’re married or to become sexually active as a teenager is TOTALLY UP TO YOU. I cannot emphasize this point enough, though the caps lock helps. This means that while you should not feel pressured to have sex ever by anyone, it also means that you shouldn’t feel pressured to abstain either. This brings me to point two…
  2. There is nothing wrong with wanting to have sex, whether you decide to actually engage in sexual activities or not. Women are taught that we are not supposed to want sex, or that it is bad or slutty to be sexually interested/active. That right there is some serious bullshit. Sex can be awesome and fun and super healthy or it can be a bad idea. It’s all about doing right. And there is never, ever, anything wrong with having sexual feelings/urges, however you choose to express them.
  3. Sex is not just penis+vagina. That point of view is pretty much a ridiculous and antiquated concept based on just the guy’s pleasure. Sex encompasses a range of activities from touching to oral sex to penetrative sex. Penetrative sex is an important step, especially physically for a woman for the first time, but everything is not either virginity or sex.
  4. While it is not necessary to have sex with a monogamous long-term partner with whom you intend to marry and have babies, it IS important that you know the person you choose to have sex with well enough to be safe with them. This means you need to feel 100% sure they will wear protection, stop if you stay stop, and respect any and all boundaries you put in place. This means that before you have sex, you will actually have to talk to your potential partner about it. None of this “swept off your feet don’t even know how it happened” shit. Be smart. Be prepared. Be open and honest. Be safe.

Ok, so now that that’s out of the way, moving on. How do you know if you are ready to have sex? Of course I cannot answer this for you, but this should help. If the following apply to you, you may be ready:

  • You want to. This sounds silly, but it’s often ignored. And I don’t mean want to in a “he wants it and I love him” way or a “I want to be like my friends” way. I mean it in a pulse racing, knees trembling, clit throbbing wanting sex sort of way. Physically, you should feel the urge to have sex.
  • You have had an orgasm with this partner before without penetrative sex. This sounds odd, but it means that you a) are with a partner who is attentive to your needs and b) are more likely to understand that penetrative sex is not the only kind of sex. This will make you happier and also means you and your partner are sufficiently mature to be addressing both of your needs BEFORE he puts his dick in.
  • Have talked about it with your partner, and made the decision together. If you are mature enough to have sex, you are mature enough to talk about it with your partner. If you blush and freak out just TALKING about it, you probably shouldn’t be doing it. Decide on what contraceptive method to use in advance, and discuss what this will mean to both of you. Sex does not have to mean “BONDED FOREVER AND EVER TRUE LOVE” but you and your partner need to be on the same page in terms of your relationship with each other. If one of you thinks having sex means you’re in love and one of you thinks it’s a purely physical expression, you are way more likely to end up in miserable emotional situation.

If these criteria apply to you, you MAY be ready to have sex. Please note, I do not say that you necessarily are or should. On a basic level, any decision you make needs to be about how YOU feel. Do not let anyone else (friends, partners, etc) make the decision for you. You should feel comfortable with your decision and with yourself. If you are in any way unsure, there is absolutely no problem with waiting until you are comfortable (IMPORTANT: Even if you have already said you will have sex with someone, you can ALWAYS change your mind. Anyone who tries to get you to have sex with them because you “promised” isn’t worth having sex with anyway). It is your body, and you are the one who controls what you do with it.

Coming soon: Sex! Fun! Relaxing your pelvic floor! Using condoms! More fun!

Love from


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Hello everyone, and welcome to the cool aunt project!

I’m CA, and I shall be your blogger. Nice to meet you all *nods at imaginary crowd*.

We are here because being a teenager… sucks, really. I know, I just was one. And looking back, I realize that most of what we are told about being a teenager is useless at best and total and complete shit at worst. So, I figured that there should be a place where people who recently were teenagers (the cool aunts) could tell you (the fabulous teenagers) about all the things we wish we had known. No judgment, no patronizing, no crap about how these are the “best years of your life”. The best years of your life are ahead of you, but first we’ve got to get you that far without any major breakdowns.

I will be doing much of the posting myself, but I have also enlisted the help of several guest bloggers to aid me in topics I feel less capable of dealing with (for example, issues relating to heterosexual sex will be handled by me, issues of homosexual sex will be passed on to more knowledgeable aunts).

Glad to be here, and welcome!

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