along came poly

Here’s something I published recently based on my research into fan fiction and sexual subjectivity! 

Obligatory link to the music video

Asking your partner to get an STD is extremely sex positive, in my opinion, and good on you for making it a routine part of your health care! I want to make it very clear that just because some people have been scared away by you taking the initiative over your own sexual health doesn’t mean that you’ve done anything wrong by taking that initiative. It is important, it is challenging, and you should commend yourself for getting to the point where you can unabashedly ask partners about when they’ve last been tested. That was a really, really hard thing for me to learn to do, and I know from my work with adolescents in a sexual health clinic that it’s hard for a lot of people – especially young people – to do. Keep asking. And don’t be afraid to cut loose people who are made uncomfortable by your asking. I won’t say that their discomfort makes them bad people by any stretch of the imagination – we’re all hurt by the dismal state of sex education (in the U.S. at least) – but you also deserve to be with people who are on your level, in this realm. Finally, generally I find that people who are better at talking about sex are generally also better at having it.

Your last two questions are more complicated. To be clear – you don’t have to be “intimate” with someone in order to ask them when they were last tested, or what their status is. Usually (but not always) I have asked that before dropping trou even with a one night stand – and if I didn’t ask before (because I forgot, or got caught up in the moment – hey, it happens!), I make sure to ask after.

But when you ask about the difference between the vulnerability involved in having sex vs. the vulnerability involved in talking about sex, brings to mind that old, slightly condescending high school health class/concerned parents saying, “If you’re not ready to talk about having sex, then you’re definitely not ready to have it.” 

The problem is, I think it’s pretty rare for people to become comfortable talking about having sex before they start having it. It’s just not something we’re taught to do. 

We’re bombarded by ideas about sex and sexiness (in movies and music and on social media), but we’re rarely given the tools to understand our own authentic desires and interests. Instead, we internalize the stories we’re given (usually told by people who want to sell us something, by the way) rather than being allowed the space and comfort to formulate our own understanding of sex and pleasure for ourselves among a supportive and affirming community. An example: When I was in college, I felt like literally all my friends were having the Best! Sex! Ever! and I was the only virgin left in the world. Turns out, most of my friends definitely were having sex – but even the way we were talking to each other about it was shaped more by our ideas of the types of sex we thought we were supposed to be having, rather than the our actual experiences and desires. 

That is bananas.

It doesn’t leave much room for intimacy to grow, but it’s not uncommon, I think, for a lot of people to choose to fake it til they make it (where “it” could be: having an orgasm; directing a partner via explicit instructions in how to give you an orgasm; having the specific kind of sex that you really enjoy; or, yes, talking about STIs and getting tested) until sex itself is a little less intimidating, rather than have a conversation that will likely be uncomfortable because we’re never given a blueprint for how conversations about sex should go in the first place.

Whew.

The way that sexually transmitted infections are treated by our culture is also probably what makes some of your partners a little skittish. There is still such a huge stigma around genital herpes, for example, even though herpes itself is incredibly common, and Teen Vogue (heyyyy) will tell you that fear of herpes was created by a drug company, and Everyday Feminism wants to dispel the stereotypes about herpes that many people still believe. 

The other complicating factor is that many, many people don’t have as comfortable a relationship with their doctors as you do when it comes to talking about their sex lives. Some of this is because many (but not all!) doctors are just straight up terrible at talking to people about sex in a non-judgmental way, especially if you’re in any type of relationship that mainstream society sees as ~alternative~ (I hate that word). But it’s also because, once again, no one (including doctors!) is taught how to talk about sex. With ANYONE. 

Factor in that when it comes to cis men, some of the messages they get about sex is that they’re just supposed to magically be good at it, and if they’re not good at it, it’s a serious threat to their masculinity, which is often a threat to their entire conception of themselves, and well…you’ve got a really complex situation on your hands.

This is all just to provide some context to why people may be reacting the way they’re reacting to your responsible and forthright questions. It doesn’t excuse it, and you shouldn’t stop asking by any means – and if a partner is saying to you that it is “sex negative” to ask about STIs and the last time they were tested, that would be a bit of a red flag to me, because it certainly is not. The choices you make with your body are your choices, and any partner who is worth getting naked with will give you the information you require in order to consent fully to having sex with them and sometimes a little discomfort around those conversations is understandable. 

First of all, congratulations on this realization. Seriously! Coming out is hard, even if you live in a city with a large LGBTQI community. And coming out as bisexual can sometimes be particularly hard, given how bisexuality is still (STILL!!) treated as a pit stop on the way to gay land, a frivolous vacation spot that straight girls go to for attention (especially if you’re femme presenting!), or just plain Not A Real thing. We get this from the media. We get this from the people we date.We get this from our family. We get this, perhaps most egregiously, from our doctors, who out of everyone in the world we interact with, should be held to the highest standards of objectivity and non-judgement. 

So, welcome to the (occasionally quite frustrating) club!

The picture above is from the episode “The Body” of Buffy the Vampire Slayer. It’s just a tiny portion of a very upsetting episode (though I shan’t spoil you if you haven’t seen the show), but it’s the first thing that popped into my head when I read your ask. Now, don’t get me started on the Why Can’t Willow Be Bi-ness of Willow Rosenberg (every “Hello? Gay now?” she utters gets a liiiiittle under my skin, I’ll admit it) but I post it here to show you that you are not alone in your fretful feelings re: establishing your street cred in terms of the sexuality that you’ve so recently come out to yourself about. I think it’s something that many queer girls reckon with at some time or another.

Why is this? Well, for bi girls, and especially femme bi girls, we’re raised in an exceedingly heteronormative culture. I mean, everyone is raised in this heteronormative culture, but bi girls tend to get it from every angle – friends who are nonplussed, because you’ve had boyfriends you’re whole life; lesbians who perhaps are suspicious (for whatever reason) of a girl who is newly out and trying to date. 

I understand your worry about feeling like other women will have to teach you, and that’s valid. But your sexuality is your sexuality no matter what, and you never ever ever have to prove it. Anyone who makes you feel like you do have to prove it is, quite frankly, an asshole. Avoid assholes of any and every gender; they’re not worth dating, and they’re certainly not worth your beautiful exciting baby queer time. 

If what you’re worried about is S - E - X, and specifically sex with vulva-havers (though here’s where I say, not every woman you might date will have a vulva) – that’s understandable, too. But it’s not like every woman-identifying person with a vulva you encounter is going to like the same exact thing that someone else likes when it comes to what gets her off. And this goes for people with all different types of genitals, in general! We all like to be touched, kissed, and fucked in different ways. So while there is certainly going to be a lot of newness to your experiences now that you’re out and widening your dating pool, you are going to be dating individuals with individual preferences, and approaching each person as a blank slate – both in terms of sexytimes, and dating and relationships more generally – can only help you. Also, asking specific questions, or asking them to show you how they touch themselves? Both really helpful tactics, if you’d like some practical advice. 

If instead what you’re worried about is that you don’t know whether or not to be open about your relative newness to dating women, well, that’s a decision only you can make. I tend to think of the things that I’m nervous about sharing with a prospective partner as opportunities; litmus tests, if you will. If I share something I’m nervous about, and that person makes me feel like crap about it? Well, get behind me Satan. That’s not someone I’m going to feel like trusting much with my vulnerability, so they can hit the road, and I’ll find someone better. 

Here’s my first sex & relationships column at Autostraddle! In it, I advise the LW to fuck in defiance of capitalism and get intentional about prioritizing pleasure.

Our cultural tendency to devalue pleasure is an added impediment, and is one that is so pervasive it often feels unconscious. Capitalist society dominates everything we learn about sex, sexuality, romance and relationships, from before we even consciously engage with them. You and your girlfriend are both working hard in demanding programs. Of course you want to devote yourself to your goals, and everything in society tells you that you have to work work work (work work) to be productive, worthwhile members of society. Under capitalism, pleasure, if it is thought of at all, is like dessert after dinner. But pleasure of all types is part of dinner itself — central to our existence as human beings, and as social creatures that frequently get into all sorts of messy, squishy, wonderful relationships with each other.

Oh, honey. The very short and very firm answers I have for you, for both of your questions, are no, and no, not at all. 

It’s Pride month, and there are lots of things floating about about queerness. Equinox has a horrible joke of an ad campaign about the ABCs of LGBTQ+, and they kick off the video with “ally” (gag me) – erasing asexuals from the queer community completely – and then lumping in kink and S&M as if those things are inherently queer, or all queers are kinky. This is the entirety of my reaction to that:

NYC Pride is supposedly going to be televised this year, because everyone wants to get in on queerness as spectacle. But the problem with marginalized identities being perceived through the lens of a dominant [read: white supremacist, cissexist, heteronormative, patriarchal] narrative (i.e., white cishets with money who like glitter and dislike the history that is the Stonewall Riots being led by Black and Latina trans women) is that the dominant narrative fucks us up. From adolescence (or even earlier if you’re Black or POC), and continuously. 

What I’m getting from you letter is mostly that you don’t feel queer enough. “Not queer enough” is just another version of “not enough” and, in my experience, at the root of every “not enough” – especially for someone who lives within one or more marginalized identities – is how we’re not shaping up to some distant, inauthentic ideal (which is *always* seen through the lens of whiteness).

What does “queer enough” look like, to you? Take a moment and really think about it. What are the narratives that you’re bringing to “queer enough” that have you stuck in the position of feeling like you’re falling short?

I’m also a queer woman who for a long time dated mostly cishet dudes all my life, and when I was stewing in my ‘not enough’ feelings, they usually had to do with my femmeness, and how I was worried about being read. (This is called internalized femmephobia.) My response was to cut off all my hair (and then, ridiculously, have a lot of feelings about being read as too butch/“too gay”; read: “too much.” We truly cannot win.) I got a tattoo of a Sailor Jerry mermaid rocking a pixie cut and reading a book with her boobs out to telegraph to the world that I LIKE GIRLS. I later got an undercut, a septum piercing; all markings of things that I thought would make me more “visibly queer.” (And maybe it did, but now I’m also Brooklyn-adjacent, so I look pretty much like everyone else. Oh well.) 

But here’s the thing with visibility that I think is important to note: My bbqueer striving to be “visibly queer” was a privilege, even as it was causing me anxiety and feelings of not enough-ness; trans folks, and BIPOC folks, queer and straight, struggle with hypervisibility in ways that my light skinned, cisgender ass generally does not, and it is important to me to state that plainly.

Did any of the things I did to establish my queer chick street cred actually make me any queerer? No. You know what does make me queer? 

The fact that I’ve always felt a little odd my whole life, and it wasn’t until I found my queerness that some part of that began to ease. My intense relationships with female friends that crashed and burned in startling ways, which I now realized were warped and stuck in a pressure-cooker by the queerness that I didn’t have words for, since I was raised so steeped in Catholicism and heteronormativity. The fact that I’ve had to fight to recognize my queerness; the fact that my parents made me stop watching Xena for “the violence” when I have a sneaking suspicion I probably was made to stop watching it for the gayness (and I don’t say that to criticize my parents at all – I don’t even think that was something that consciously registered for them; that is part of my queerness too). The fact that my dad tried to make me stop watching Buffy when Willow came out as gay – he TRIED lol – and I literally told him over my dead body. The fact that Willow came out as gay and it still took me an additional ten years to realize that I’m bisexual, bc lol, where are all the bi girls on TV??? Where are the bi girls who look like me? (Here’s one.)

I understand your angst, though. As queer women, we’re so often told that our sexuality is contingent on who we’re with. My doctors have treated me that way – when I have male partners, I’m straight, and when I have female partners, I’m gay. When I come out about being non-monogamous, I’m pretty sure all they see is a neon-sign over my head that, depending on the doctor, reads “HIGH RISK” at best, and “SLUT” at worst. These are messages that we have to deal with every day. It is so, so rare to find a place and a community that validates who you are, exactly as you are.

And the queer community isn’t exempt from that, either! I had a girlfriend who identified as a lesbian who had a problem with me having sex with dudes. I had a girlfriend who identified as poly who hated the idea of me having other partners, so she asked me to be in a closed triad with her and her husband – and then the two of them, jointly, decided to dump me, in part because seeing him with me scared the crap out of her. 

Our world is imperfect, and our communities reflect that. It takes strength and resilience and the deepest, fiercest love for who you know yourself to be to fight that. It can be exhausting, and sometimes we don’t always win these battles with “not enough,” because our society is not structured to encourage or even allow us to love ourselves. And I’m sorry for that, and I am sending you all of my love, not just because it’s June and it’s Pride month, but always, because you deserve so much better than this.

With regard to where you stand on the spectrum of monogamy and non-monogamy – fuck that scale. You are where you are, and how you do relationships is your business, and your partner(s)’ business, and anyone on the outside looking in can go fuck themselves. Maybe you’re feeling more monogamous right now – cool. Maybe you’re just super deep in New Relationship Energy with this exciting new person – that’s also fine! Either of these things or neither of them can be true, or one of them can be true sometimes, or they can both be true at least half the time, and the only thing that means is that’s where you are at right now, and where you are right now in your dating life is not a comment on how ‘good’ of a queer you are. You don’t have to be good. You just have to be yourself.The most important thing I ever learned about queerness was last summer at the LAMBDA Writers Workshop. My teacher was Benjamin Alire Saenz, and the first thing he asked us to do was to write about what scared us most in the world. I wrote about not being enough – not queer enough, not Latina enough, not good enough at non-monogamy, not enough of a writer. Not enough, not enough, not enough. He said to us, “Queer is an identity that is entirely self-defined” – and your ability to do that, to be who you are, all of who you are, and say fuck you to the cishets who want queerness to look the way they want to consume it, and a similar buzz off to the queers who would suggest your queerness is not queer enough because of who you’re with – is not only an act of resistance, but also the best gift you could give yourself, and a gift you have always deserved.

Damnit, Jim, I’m a sex educator, not an aromatherapist!

Sorry, couldn’t help it.

Hi, anon! I’m not sure what you’re looking for in terms of genital health – if you’re dealing with anything like pain, itching, discharge, or just general something-doesn’t-feel-quite-right-ness, I definitely suggestion going to see a doctor and getting professionally checked out. 

And while I’ve definitely been one to dabble with essential oils in the past (I like clary sage for my hair, and lavender for my neck and shoulders if I’m feeling tense), I’m definitely pretty willy-nilly when it comes to how I use them, so I’m far from a professional resource.

I put a call out on my Facebook for reliable essential oil information when I read your ask, though, because I wanted to gather some sources. 

Unfortunately, all’s not well on the essential oil front, and some of the sources I got included this one, which is by Kayla Fioravant, the author of The Art, Science, and Business of Aromatherapy. In it she’s pretty critical of the essential oil industry, and stresses the danger of using essential oils all willy-nilly – especially if you ingest them (don’t do that), but also if you apply them directly to the skin without diluting them in a carrier oil. Is my face red, or what.

If you’re a person with a vagina, or you’re frequently up in some vaginas, I will say that vaginas definitely don’t need essential oils to stay healthy! Vaginas don’t need much of anything to stay relatively healthy, barring STIs or other health concerns, because typically the vagina is self-cleaning and really good at what it does, and in fact, introducing strange substances into it can upset the delicate balance of flora that keeps it chuggin’ along doing its vagina thing. So to keep a vagina healthy, all you really need is a very gentle soap (for the vulva, not inside the vagina!) and water – be careful to avoid things like wash clothes or loofas or anything like that, because they can trap bacteria which’ll end up irritating the sensitive vagina.

For external use, tea tree oil is good for ingrown hairs (and strippers will swear by it), and so is witch hazel (which is not an essential oil but is what I use when I have to dance around in a thong in public). Tea tree oil suppositories also exist for yeast infections, but this is a thing that I would check with a medical professional first before you use it (full disclosure: I have not used tea tree oil suppositories for yeast infections; and I prefer the Monistate 3-day little egg shaped suppositories rather than the cream bc the cream BURNS LIKE A MOTHERFUCKER. YMMV, however, and also, consult your doctor.)

The short answer is: yes, I have felt secondary in poly relationships, and it sucked. I dated a married couple and there were times in that relationship where I was put in a position where I didn’t get to fully consent to the ways in which I was treated, or where the nature of the different relationships in play were not being fully communicated to me. I also dated someone who had another serious partner who was essentially a primary partner, though neither of them used that terminology; their relationship was rocky, and the two separate relationships (mine with my boyfriend; his with his primary partner) couldn’t sustainably continue at the same time. Both times, it felt a lot like having the rug pulled out from under me, where I thought I was agreeing to and engaging in relationships with one set of dynamics, only to discover further down the line that the dynamics of the relationship were something else completely. 

The way I dealt with it, in both cases, was for those relationships to end.

That said, that isn’t necessarily what I would encourage for you! It sounds like this relationship does make you happy, and, from the short bit you’ve described here, things seem relatively peaceful with your metamour (the fancy poly term for your partner’s wife). That’s awesome, and just because that hasn’t been my poly experience so far, I don’t want to make it seem like I think relationships like that aren’t possible. They totally are, and I know plenty of people who make poly work when two of the people involved are married and the other is single.

Because of my experience, though, I’m very wary of dating couples/partnered people. I, personally, don’t do it anymore. If I were to do it, I would want to make sure BOTH people involved, if they haven’t practiced much polyamory before, were both not only inclined to read up about ethical non-monogamy (More Than Two is still my favorite book on this topic; I would thrown in The Game Changer to get a bit more of a perspective on how the power dynamics of a couple can effect the single lady portion of the V) but then actually sat down and read those books.

Since you’ve said your new to poly, I think it would be a really good idea for you to take a look at some of those books, too. Non-monogamy is hard, because relationships can be hard and vulnerable, and no one really teaches us how to be vulnerable. The more you know about relationships – most importantly, the more you know about your relationship with yourself, what makes you tick, what your needs are, what your boundaries are, etc. – the better off you’ll be. I would also suggest Emily Nagoski’s The Scientific Guide to Successful Relationships, which is only three bucks on Amazon, because she goes into the concept of “staying over your own emotional center of gravity,” which was very helpful to me not only in the romantic relationships I’ve found myself in, but also in my relationships with friends and family. Knowing how to take care of yourself first, as your own primary partner, is probably one of the most valuable life skills a person can develop, and has certainly been the one I’ve been working on most diligently for the past couple of years.

Still, though, couple privilege is real, and even people with the best of intentions can fall into the traps of femme competition (the idea that women need to be pitted against each other for the affections of some dude) and scarcity (the idea that there is not enough love to go around; there’s plenty of love, there just isn’t an infinite amount of time). It takes a long, long time to unlearn these, because they’re part of the sludge that makes up capitalism and patriarchy. We’re steeped in it. So for me, when I get involved with people now, I want to know I’m involved with people who are also committed to unlearning and resisting the oppressive systems we all struggle within, to being conscious and intentional, and interrogating what drives their actions within relationships, and who will hold themselves accountable in a meaningful way if they do something hurtful. 

I want to push back a little bit on how you’ve framed the second part of your question. You state that you don’t have a primary partner of “your own” yet, and that set off warning bells in my head. It sounds, to me, like perhaps you’re experiencing some jealousy/insecurity (completely natural and normal in poly relationships, btw, so I hope you won’t judge yourself for it) and that you think having your own primary partner would help alleviate that. And it might, maybe. But I think that puts an unfair amount of stress on whoever this hypothetical primary partner of your own might be – would you be engaging in a relationship with them because you genuinely wanted to be in relationship with them, or because you just needed a primary in your life to not feel so secondary? 

If you want a primary relationship because you want someone to build a life with, to share things that maybe you don’t get from this relationship you’re in right now, for logistical reasons – more time together, the intimacy of living together, if that’s your style and a goal of yours – that’s totally okay! And you deserve to have those things in your life. But if there’s stuff that’s missing from this relationship, or if there is something that’s making you uneasy or insecure or just plain making you feel bad, then I’d suggest sharing those feels with your partner, too. Because even if you are a “secondary” partner (in that you’re not his wife and perhaps not likely to be), you’re still a partner in relationship with him, and you deserve for him to show up for you as a partner who loves you, especially when you’re struggling. 

Hey, anon! Unfortunately, I don’t think this is something that would work at a nude beach, because even though people are consenting to be naked around each other in public, they’re not consenting to be engaged in any sexual activities with each other. And it sounds like being objectified does have an element of sexual gratification to it for you. Even if you were to get a group of friends who know that this is what you want and that it’s okay for them to objectify you, the other people around you in that public space aren’t consenting to be a part of that scene, and their ability to consent absolutely matters. I guess you could get your friends to call you whatever names you’d like to be called within your own group, but if this is a follow up to the previous question about nude beaches where some dude hollered at me about my nipples, then yeah, that was a really public thing that involved not only me and him, but the people around us as well. That kind of objectification ropes in strangers who you won’t be giving a chance to give meaningful consent to observing you being objectified.

An important thing to keep in mind: A lot of different types of people frequent nude beaches. When I went to Riis last year, there were tons of queers, many of whom I know in passing but enough to know they’re pretty kinky. Some people, though, were also there with families that included little kids, or people there with their friends just lookin to hang out and enjoy the day, and probably most of them didn’t have in mind watching an objectification scene in the middle of their beach getaway. I think it’s also important to remember that just because people are naked in a space together, it doesn’t mean sexytimes are afoot – and I think there’s a lot to be said for the value of desexualizing nudity. Finally, objectification is a tricky kink that can be triggering for a lot of folx for a lot of different reasons, so you definitely want to make sure people are consenting to be a part of this, even if just as a witness.Still, that’s not to say that this fantasy isn’t something you can’t make happen! If you have any kink-inclined friends, why not try hosting a sex party of sorts, where attendees know the deal beforehand and can agree to exactly what you have in mind. The beforehand element is important, because it’ll give you the time needed to create the agreements for that space and make the distinction that yes, it’s okay to objectify you personally, but not people generally. 

If it is important to you to still have a public element to this fantasy, you could look into going to a sex party. There’s one in NYC that I’ve been to where part of it is set up like a labyrinth of different areas where people are having sex in separate little spaces and there are peepholes cut out if you feel like gettin your voyeur on, as well as larger spaces that have fewer people engaged in a scene and larger groups of people watching. In that space, at least, it’s clear that the reason people are there is to engage in sexual behavior in some way, shape, or form, so an environment like that might be better for what you wanna do – although, OF COURSE, it’s still hella important to have ongoing conversations about boundaries and consent at a sex party, too. 

Love ‘em! Although, I guess I love topless beaches over nude beaches, not so much bc I’m shy about having my bits out on the beach, but more ‘cause there are just some places I don’t wanna experience sand/sunburn, yanno? And I know that I personally would have a what-to-do-with-my-body-hair existential crisis at a fully nude beach (which is purely a me-thing. I think in general people should do whatever they like with their body hair, I just have very mixed feelings about my own.)

THAT SAID. here is one thing I don’t like about nude beaches: This past summer instead of going to the Pride parade I went to Riis beach in NY, and a middle aged gay dude shouted a very weird compliment about my areolas at me from a couple of blankets away. That made me uncomfortable, and I wish cis gay dudes would realize that they can, in fact, objectify femme folks just as much as cis straight dudes can, and it doesn’t reeeeally make it any less annoying or uncomfortable just ‘cause they’re gay. Get your shit together, cis gay dudes.

I definitely don’t think it’s bad for you to buy a vibrator or other toys if you haven’t been able to get yourself off! In fact, I recommend it! You know how when you ride a bike, sometimes the only way to learn how to ride a bike is to accidentally just *get it*? Or – and this is a pretty me-specific analogy here – but I recently started pole dancing, and even the simplest tricks seem impossible, until I accidentally just *do them*. And lest you think I’m impressive or something, I mean, just climbing took me forever to learn, but once I did it right the first time, my body immediately knew it. 

Orgasms and masturbation are sometimes a bit like that, for some people.

Let me tell you a story.

First of all, anon, I wanna say that I’m sorry you’re going through this! It sounds like it really sucks! I put together some information for you from various sources, but I do wanna stress that – if you haven’t done so already – you should go see a doctor about this. Since I’m not a doctor, I can only tell you some of the causes behind painful sex and masturbation, but some of the causes are actually pretty serious health issues, so definitely get checked out.

The somewhat dubiously named Bad Girl’s Bible has a fairly comprehensive article on painful sex here, which goes into how your period, possible bacterial infections, and how stuff-knocking-into-your-cervix can cause pain, as well, but it’s a little too interspersed with “learn how to make your man’s toes curl” information for me to wholeheartedly recommend that website. Girl, if I’m in pain, IDGAF about making my partner feel good bc I WANNA NOT BE IN PAIN.

But I digress.

Since this has been something that’s been going on for you for a while now, the more immediate causes listed in the BGB probably aren’t the culprit. (Cramping and pain during or after sex can also be a sign of early pregnancy, but since this has been going on for 2 years now with, I assume, nary a baby in sight, you can disregard that as well. Here is an incredibly thorough website about that, though, just in case.) 

The Mayo Clinic has a really in-depth page on painful sex, also known as dyspareunia. There are lots of different ways sex can be painful, such as what they list here:

Pain only at sexual penetration (entry)

Pain with every penetration, even while putting in a tampon

New pain after previously pain-free intercourse

Deep pain during thrusting

Burning pain or aching pain

Throbbing pain, lasting hours after intercourse

Each different type of pain can be caused by something different. For example, pain at penetration can be caused by lack of lubrication (in which case, get thee to a lube bar! Or at the very least don’t be afraid to try out a lube or two to see how you like it), infection, or vaginismus. A friend of mine received treatment for vaginismus (related to vulvodynia, vaginismus is chronic pain in the area around the opening of your vagina, caused by spasming of the walls of the vagina) and it was a long treatment process that involved both talk therapy and physical therapy, which is why it’s so important that you reach out to a professional in person.

Deeper pain can be caused by other serious illnesses, such as pelvic inflammatory disease (inflammation of the uterus, ovaries, and fallopian tubes which can lead to scarring and infertility if left untreated), endometriosis (the symptoms of which can include rectal pain and pain with bowel movements), uterine fibroids, cysts and cystitis, and even things like IBS and hemorrhoids. Here's a forum from 2011 in which a 23 year old writes in with a similar problem, and is answered by an AASECT Certified MD.

The Mayo Clinic also lists the various ways in which our emotions factor into how we experience sex and pleasure – emotional trauma could manifest physical, particularly if it is due to sexual trauma, but even regular ol’ stress plays a factor in sexual response and desire (something that Emily Nagoski writes a lot about in Come As You Are).