How do I keep him from going in the wrong hole?

I am 23, so this will probably sound silly and foolish but I don't have anyone else to ask these things so here goes: First off, how do you know it's in the right hole? My boyfriend and I were getting involved last night for the first time, and at first it hurt horribly like I was being ripped apart. He re-adjusted and it still hurt a little but nothing like before, it was mostly just a lot of pressure. Was he in the wrong hole before? How do I keep that from happening? Also his penis is BIG and my vagina is not. How far in should he go? Can he cause damage by going too far? Thanks for the advice.
Robin Mandell replies:

I don't think these questions are silly or foolish. Most of us, and I count myself in this group, don't get many opportunities to learn about our bodies, or much about sex, and find ourselves either figuring things out as we go along or searching for information to help us. Sometimes that's even the case for people in their 30s, 40s and beyond. So, there's no judgment from me on these questions, nor would I say there should be from anyone else.

Lots of people don't know what's going on with their genital anatomy, or with other parts of their body, either. So, without further ado:

An Anatomy Lesson

A person with a vulva actually has three "holes" (or what I prefer to call openings) per their genitals: the urethra, the vagina, and the anus. Starting at the front of the body, we first have the urethral opening, where one urinates from. This opening is very, very tiny, so it likely isn't the opening you're talking about.

Next comes the vagina, then, finally, the anus. The vagina and anus are adjacent to one another, separated by a narrow band of tissue and muscle called the perineum. They're quite different in structure. The vaginal opening is surrounded by, and, for some people, hidden by the inner and outer labia, while the anal opening is a sphincter, a ring of muscle, leading into the anus, which in turn leads to the rectum. From your question, it sounds like you want your boyfriend's penis to end up in your vagina, for vaginal intercourse. I wanted to clarify this because some people enjoy anal intercourse, and for those people, the penis ending up in the anus isn't the wrong spot at all.

There are other reasons besides having genitals not fit together in a way that is comfy for your body for intercourse to be uncomfortable, painful, or not pleasurable. At the end of this, I'll give you some reading material that will, I think, give you more to think about and more to try in your quest for satisfying partnered sex.

No matter which opening you wanted your boyfriend's penis to enter, there really is no way for me, or anyone, to tell you whether it ended up in your vagina or your anus unless they were watching you at the time. Given their proximity to each other, either or both are possibilities. If you felt pressure in or around your anus, that doesn't necessarily mean that your boyfriend's penis entered there. The tissue between the vagina and anus -- internally and externally -- isn't very thick at all, and they're almost stacked on top of one another inside your body, so pressure or sensation in one opening can often be felt in the other. Plus, all the muscles of the pelvic area are connected in some way, so any pressure on the vaginal muscles can translate into pressure on the anal and rectal muscles, and vice versa.

I can tell you how you and your boyfriend can make sure, for next time, that his penis ends up in the place you want it.

Either one or both of you can guide his penis with your hands to your vaginal opening and help it enter. Easy as pie!

There's this belief out there, I think, that the penis just automatically knows where to go, like some kind of heat-seeking missile. But contrary to the many jokes out there (jokes I'm not at all fond of) about people with penises having their brains between their legs instead of between their ears, penises don't have brains and don't make decisions. Not only that, but where the people with the actual brains and real decision-making capabilities want the penis to go will be different for everyone -- some people might not want it inserted into their bodies at all and will just want the penis to rub on the outside of the genitals; some will be interested in vaginal intercourse; some will be interested in anal intercourse. Some people will want all or some of these activities based on what they want on a particular day or with a particular partner.

As you can see, that's an awful lot of responsibility for a body part that doesn't have the capacity to think. Better, then, for people to take charge of making sure it gets where they both want it.

There is also, I think, this idea that once intercourse (or any other sexual activity) starts, it's a seamless, almost self-propelling event requiring little input from the participants. What instead tends to happen in reality for most people, most of the time, is that sexual activities involve stops and starts, a need for repositioning genitals and other body parts, and sometimes, for activities involving genitals specifically--a need to put genitals or other body parts back where both partners want them after they've slipped or fallen out of position. Actually, I'd say this sort of figuring things out happens with most sexual activities, and with most partners, regardless of how long they've been together or how much experience they have with a given sexual activity.

As for how deeply your boyfriend's penis can or should be inside your vagina? That's up to you and about what feels comfortable and good for you. Your vagina has an end, so his penis can only go so far. Your body is the best guide for what feels good versus what is too much. If his penis inside your vagina at certain depths or entering in certain ways is uncomfortable for you, that's a clear sign to just do something different so that his penis will not go so deeply or be at those angles. Our bodies are designed to tell us what they need and want by how something feels to us, and what they don't need and want, so you really can trust your gut on this one, and go with what is comfortable, not-painful, pleasurable (or all three) for you.

I know it may seem as if his penis is much bigger than your vagina, but the vagina is really quite elastic. It also expands, in both length and width, with sexual arousal, and, as it turns out, when aroused, the average length of the vaginal canal is almost identical to the average penis length. For the full low-down on vagina size, take a look at this.

While everyone's specific angles and sizes are going to be different, it's pretty uncommon to encounter a couple for whom the penis and vagina just don't fit at all when both people are very turned on, want to be engaging in intercourse, are taking their time, using lubricant, and no one has any vulvovaginal health conditions or issues -- like vulval or vaginal pain conditions.

What More Can You Do to help with this?

It sounds like you might not be very familiar with your own genitals. If that's the case, or even if you do feel like you're familiar, I'd suggest taking some time to get to know them, or know them better. I think this'd help you both in knowing your body better and in positioning your body for sex with your boyfriend.

Here's some material on anatomy, including some diagrams, to get you started with that:

Once you feel familiar with the basic anatomical structures, I'd suggest taking time to get to know your own body -- with your own hands, eyes, or both -- to figure out your own unique configuration of those anatomical structures, and to see how it feels when different parts are touched or stimulated in different ways.

You might choose to do this exploration during masturbation, or you might choose to just explore without erotic or sexual thoughts. Either way is fine; both ways are fine. You might start out just learning about your body parts, and find that doing so is an erotic experience for you. That's okay too. This is about getting to know yourself more, and you're bound to encounter some surprises along the road to doing that.

If you're still feeling confused by your genitals, talking with a gynecologist or general healthcare provider who can guide you -- perhaps with the aid of a mirror -- through identifying your different parts might be helpful. Since you're engaging in partnered sex, it's time for you to start your sexual healthcare anyway.

If you don't have a healthcare provider already, or don't have one with whom you're comfortable discussing sexual healthcare, you'll want to find a new provider or clinic. Here's some information on doing that, and some information on what to expect when going for a gynecological visit.

Talk to your Partner

In your question, you said that your boyfriend readjusted himself after a while. Did you let him know that you were uncomfortable and there was too much pressure or was he just readjusting himself because he decided to?

I ask because far too often I hear about the female partner in a male-female couple deferring to the male partner once intercourse begins, or for sexual activity in general, or becoming passive during sex, rather than being an equally active participant. I'd say this is somewhat about gender, but also about whose body is the receptive one; that is, who's body opening is having someone else's body part inside of it. Intercourse (and any other sexual activity you engage in together) involves both of you, both your bodies and both your minds. Somebody being physically receptive-- like having a vagina that a penis goes into, having a vagina that receives a penis -- doesn't mean that that person can't also be an active participant.

This is where I actually find it a little difficult to use the word hole to describe a body part and instead tend to use the word opening or to use the anatomical term, as it seems, to me, to connote something impersonal and inactive, when, during sex or any other activity in which our bodies are interacting with other people or with the environment around us, our body parts are anything but inactive. That is, even if a body part isn't moving, it's responding to physical stimuli (both touch and pressure) and to the thoughts we're having about whatever activity we're engaged in. If you'd like to read more thoughts around this idea, I find this article to be a really thought-provoking read.

You're just as much a partner in partnered sexual activity as your boyfriend is, and have just as much say in what happens.

Since your question is specifically about intercourse, I don't have a good sense for how physically or emotionally ready you felt for that intercourse at that particular time, or whether you felt like it was something you needed or wanted to do more for your boyfriend then for you.

While it's true that physiologically vaginal intercourse on its own isn't always, for the person who has the vagina, something to write home about, there are plenty of ways to actively make the partnered sexual activity, including slowing things way down satisfying for everyone involved. No partner's pleasure supercedes another's discomfort.

Slowing things down sexually also has the added advantage of helping you keep things safe and comfortable. As I said above, the vagina does have an end to it, so you will not be injured by your boyfriend's penis going too far. Some people do experience soreness or injury with intercourse when entry is too forceful, or when too much friction irritates or abrades delicate vaginal tissues. If indeed your boyfriend did enter your anus, or does ever enter it in future, know that there is a greater risk of injury with anal sex when it is not expected or prepared for. The anal and rectal tissues don't lubricate themselves, as vaginal tissues do, and are even more sensitive to cuts and abrasions, and accompanying infections.

So, doing any sexual activity you choose slowly and with intention can help you avoid injury, as can communicating what you're feeling, needing, and wanting to your partner. Pain or irritation, in any place and at any level, is your body's way of telling you that something is wrong. Often pain comes before injury to tell us that whatever is happening to us needs to stop or change, and if we don't stop or change it, injury does sometimes occur. So, if you do opt to engage in intercourse again, and you're feeling like you're splitting apart, please stop what you're doing, okay? You don't have to put up with that kind of pain, or any pain at all!

You're allowed to ask for things to change. You're allowed to stop things to reposition or try something else if you're uncomfortable. It's your body.

There are so many beliefs out there about how first intercourse is supposed to be painful for the person with the vulva, that I worry that some people experiencing first intercourse don't think they have a right to complain or ask for a change if they're uncomfortable. While there are several reasons why first intercourse (or tenth or one-hundredth intercourse) would be uncomfortable for someone, none of these is a reason to just "grin and bare it" through discomfort or outright pain! Sex is supposed to be fun, and while what that fun means or looks like will depend on the people involved, fun isn't going to include doing anything you don't want to do or wind up finding uncomfortable or even distasteful.

The easiest way for you and your boyfriend to make sure you're both engaging in the sexual activity you want, and that you intended to engage in, and that won't hurt either of you, is to talk about it. you get to say what you like, and he gets to say what he likes, then the two of you get to figure out what you both like together. I hope that sounds like fun, because it really can be.

So, how do you make sure your boyfriend's penis doesn't end up where you don't want it?

  • Get familiar with your genitals.
  • Give his penis a hand.
  • Actively participate in what you want and actively speak up for what you don't want.
  • Talk with your partner.
  • Check in with yourself with a "Am I having fun?" and speak up or change things if the answer is "No."

Here are a few more resources to help you with these things and to help, I hope, you have more satisfying, comfortable partnered sexual experiences.

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