How to have sex for the first time (ever, or with a new partner) – by Katie Reeves

I think as a teenager basically you fall into one of those two categories: even if you never have sex, you don’t have a partner, you’re not really interested in sex, a lot of people around you are talking about it, talking about it, asking you why or why not. I think a lot of these underground teenage conversations revolve around sex in some way. When kids come and talk to me, one of the most common questions is- I don’t know when I should lose my virginity… how do I know when I should lose my virginity? 

And usually it’s not asked like that, they come in, they’re having interactions with a partner and they get really close, and it’s scary. Because in the moment your body is telling you to do something that you haven’t really thought through and that society has made a huge deal. So a lot of the conversations I have with kids is about how to not necessarily make sex a big deal. 

And one of the ways to do that is to prepare. 

There are a couple ways to prepare. 

There are a couple ways to answer the question “when.” 

We prepare in a physical way–we identify the partner they want to lose their virginity to, and then we think of all the ways to decrease the probability of there being a negative outcome. Things like making sure that pregnancy is not an issue; using condoms, using birth control; identifying if oral contraceptives are something they want to use. Having two different forms of contraception is always the best option–ideally a non-physical barrier such as the shot or an IUD or an oral contraceptive, plus a physical barrier such as condoms. Having two types is the best. Having one type is necessary. One of the things I tell girls is that of course there might be a conversation where boys are like “ugh I don’t want to wear a condom, it doesn’t feel as good…” and I just nip that right in the bud. Basically if a guy is telling you that he doesn’t want to have sex with you with a condom because it doesn’t feel good, he has no idea what he’s talking about. 

There might be some differences, but when you’re a teenage boy and you’re getting the opportunity to have sex, you are super super stoked about it, you could literally wrap that thing with a baseball mitt and it would still be the best day of his life. There’s absolutely no reason why that 15-17 year old boy should not be the luckiest person alive to wrap his dick with a condom and be able to have sex. 

So, we try and prep for that moment when the person you’re having sex with asks if they can do it without a condom. And being confident in your decision- you know, your vagina is a temple and it has a dress code, is basically how you need to approach it. And making sure that you feel confident and no part of you wavers when you’re not in a sexual encounter. When you’re not in a sexual encounter, when you’re sitting at a table talking to me or talking to a friend or when you’re thinking about it ahead of time, no part of you wavers on that decision to make sure that you are having safe sex the entire time. So, condoms is one, and identifying the fact that a really good guy might still try and have sex with you without a condom. And that sometimes feels icky because we want to think really highly of the person we’re dating, but sometimes there are misconceptions on the guy’s part, too. Sometimes they can think, well I’ve been told this is ok, or that pregnancy isn’t an issue until I ejaculate. Making sure that there’s a lot of information around why having a condom on the entire time while having intercourse is super duper important. So, condoms, birth control, and contraceptives are one way to decrease the likelihood of making the first time you have sex a big deal. 

Another is to reduce the risk of STDs. So making sure kids know the difference between a physical barrier protecting against STDs and for instance an oral contraceptive which does not prevent against STDs, and having that difference be super clear is also extremely important, and that’s why having two forms of birth control is even more beneficial. So we’re trying to prevent STDs: the best way to prevent them is to have both you and your partner get tested before engaging in intercourse. It’s really hard because it’s an awkward conversation and it’s a trip to the clinic. I’m not sure about Chile, but in the US there are plenty of places you can go to get contraceptives, to get STD tests, and to get sexual health resources in general. So if there are options like that, that’s definitely something to consider before engaging in sexual intercourse with your partner. 

Taking about that conversation- do we want to have that conversation with our partner, do we not want to have that conversation with our partner, why don’t we want to have that conversation with our partner. That conversation with my teens usually renders a lot of interesting responses. For example we get people who say, “Well, I just don’t feel that comfortable with him.” And everytime it leads to the point that if you don’t feel comfortable talking to your partner about the potential outcomes, and the potential negative outcomes of sex, then it’s going to be really hard to convince yourself that having sex with that person is a good idea. So, making sure that you’re comfortable to a point that you’re willing and able to talk about that with your partner, and it doesn’t mean you need to be married or dating or exclusive with that person, it just means that you need to be able to engage in a way that is health, so that if you were in that sexual encounter, you also feel comfortable saying “stop,” or “I don’t like that,” or “I do really like that,” so that the sexual encounter is actually worth your time. 

Ok, so we talked about reducing likelihood of pregnancy, reducing likelihood of STDs, and the third way of knowing when you’re ready is not necessarily how long you’ve known someone or how good of a relationship you have with them, it’s not who that person is, how old you are, how long you’ve been dating, whether or not they’ve said they love you, or what kind of commitment you have, but rather are you able to make this decision ahead of time. So I tell these girls in particular- decide whether or not you’re going to have sex with someone the day before, at least, preferably weeks before. And then sit with that decision, and do not make that decision in the moment. In the moment decisions are always going to be questioned after the moment, no matter what, even if they’re fine and there’s no negative outcome, or even if they’re right. But if you have negative outcomes to a sexual encounter and you decided in the moment then you are always going to question that decision afterwards. So, making sure that you’re making the decision for whether or not you want to lose your virginity, whether or not you want to have sex with someone, not in the moment. And this is followed up with a conversation around how different it is when you’re in the moment, when you’re intimate with someone; it’s real. Sometimes it’s hard to put your sexual desires on the backburner; sometimes it’s really easy to put your sexual desires on the backburner but it’s really hard to tell someone, that you want validation from, “No.” It can be really hard to stop something that your partner is enjoying, even when you’re not enjoying it. And so making sure that we can review those scenarios ahead of time and say, there might be a scenario in which this guy is beginning to have sex with you and he is absolutely loving it, and he’s telling you how sexy you are, and that this is the best day ever, and how much he loves you, and all this amazing stuff… but it hurts for you. And if that’s the case, you need to stop. Sex should never hurt. This is also a common misconception, that the first time will hurt. But I’m a huge proponent of your body will prepare you for the things that it wants, and if you’re too in your head or you’re too anxious, then it might hurt, and if that’s the case then you need to stop. Sexual encounters don’t need to be negative. And so if we’re not able to be comfortable enough with our partner to say, I know you’re into this, and that makes me happy, but we still need to stop because I am not into this right now, then it’s going to be a potentially big deal, when sex doesn’t need to be a big deal. 

So we’ve identified the ways in which we are making sex, for the first time especially, not a big deal. We’re decreasing the risk of pregnancy, decreasing the risk of STD’s, and we’re making our decisions about whether or not we’re going to have sex or lose our virginity way ahead of time. And I think that the best thing we can do as adults, or the best thing we can do as people who are not in the situation, the best thing we can do to help the people who are is to really get real about what the situations are like. And to get real about how a lot of our sexual pleasure comes out of pleasing another person. Or somehow we find ourselves in sexual encounters that aren’t really about our sexual pleasure at all; sometimes they’re about getting validation from the cute guy at school, or about feeling wanted or feeling needed. And when we can get real about that type of conversation, then we can be realistic about what to anticipate in sexual encounter with those specific people.  

We talk about consent a lot. So if somebody has consented to sex and they say yup, I’m all about it, they flirt with their partner all day long, all night long, they’re finally in bed and they’re in the middle of sex and then all of a sudden that person decides, “nope, i’m done,” then it’s absolutely appropriate. When I have these conversations I start with the most unrealistic, unlikely scenario that makes it super clear that in any situation, it does not matter what happened beforehand, if somebody says to stop, you have to stop. And having that conversation also with your partner ahead of time, too, can decrease the likelihood of making sex a big deal. If you feel safe and if you feel heard then you will have less issues and get more pleasure out of the encounter. 

We also talk about, for females in particular, that even when you’re not sexually active, it’s still ok to masturbate. And a lot of the time when teenagers masturbate before losing their virginity then they might have more pleasurable experiences in their first, second, or third time, and then might even have a reduced risk for negative experiences not just because of a lack of pleasure, but negative experiences of sexual assault, or increase their likelihood to respond if something feels bad. If you know what feels good, because you’ve done it to yourself, then you can better identify what feels bad. 

And I think I’ve mentioned that quite a few times so it’s worth noting that there are a lot of encounters with teenage boys where they are getting their sexual information from porn, or from these outside information sources that tell them that women want something specific that may actually be very painful or very negative. I’ve also had lots of teenagers talk about how boys having manual (hand) sex with girls can be very painful, so like fingering girls can scratch girls internally or hurt them. But if a girl has done that to herself then she’s going to be able to know and feel confident in her decision to tell that guy, “hey that doesn’t feel good. Look, you need to stop.” When I have a lot of girls who don’t feel confident in their perception of the situation, so they’ll say, i don’t like that that feels bad, but maybe this is what it feels like and maybe i’m just different and i don’t like it. I’ve heard that sex hurts so maybe that’s what it’s supposed to feel like. So again talking about all of that stuff ahead of time can really reduce the likelihood of it happening and can make sex just not that big of a deal. It can actually make it something kind of fun. 

I love to be a proponent of confidence in teenage girls. I think there are so many things we don’t talk about that make us question ourselves as females. And if we can be super confident in what the encounter is going to look like before we have it, not only are we going to enjoy ourselves more but our partners are also going to enjoy it more. I’m a firm believer that teenage boys would love nothing more than to engage with a very confident teenage girl, because boys don’t know what the hell they’re doing either. So that being said, all of this information can be flipped on its head and told to boys from that perspective so that you can say, yes fingering feels good but sometimes you can scratch and so asking the girl how it feels, all that kind of stuff is really important. And making sure that yes, you can get pregnant from pre-cum, let’s talk about it, the pull-out method doesn’t work, and sex still feels good with a condom on- congratulations you’ve finally found the holy grail, you can still do what’s best for you and have sex. 

And if you ever are wondering what you should do, if you should speak up and say something or not, just think, “what would Cardy B do.”  


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