Heather Corinna replies:
I am 22 years old and my BF is 23 years old. We are both virgins and we both want to stay virgins until marriage. We have been together for 3 years now and lately he mentioned to me that he wants to have anal sex. I want to do it but I want to ask if he should wear a condom. Also, will it hurt?
Please understand that anal sex is sex.
So, if you do not want to have sex until marriage, then don't have sex until marriage.
Anal sex poses the same -- and sometimes higher -- risks of infection that vaginal sex presents, can pose pregnancy risks like vaginal sex can, and presents all the same kinds of emotional or relationship risks or challenges any other kind of sex can.
We have a lot of pieces on anal sex here at the site already, so let me connect you with those, and some others pertinent to where you're at right now:
As far as if anal sex will hurt or not, what you'll find in most of those pieces is that it may or may not, but the way to find out if that's something that feels good to you isn't to start with anal intercourse, but with more gradual activity like massage around that area, or a lubricated (and preferably gloved) finger around or inside your anus.
You speak to what your boyfriend says he wants, while telling me that something you want is in conflict with that: you don't want to have sex until marriage. Not only do we know that people tend to be happiest with their sex lives when the choices they make are those they really want to make, but sex with a partner is about the wants and needs of two people, not just one. Do YOU want to have anal sex, for yourself? Have YOU found that other kinds of anal sexual stimulation -- like with fingers or toys already feels good to you? Understand that just due to your anatomy, while a male partner will be likely to reach orgasm through anal sex alone, you're not, and may not even have all that much pleasure just from anal sex. So if you are going to do this, and will want this to also be about your pleasure, you're likely to want other sexual activities to be going on -- that means you'll need to think about those things too, and that whatever those things are, they'll have to be okay with your partner.
(And I have to tell you that if your boyfriend says he is ONLY comfortable, value-wise, with doing sexual activities that please him but not you, that this probably has zippo do to with values and more to do with him finding ways to just please himself. In or out of marriage, that's not a good recipe for a healthy sexual partnership that is about both people involved. If your boyfriend just wants to please himself, he has his own two hands for that: sex with a partner is supposed to be about him AND his partner.)
Since you state you want to save sex for marriage, the best way for you to find out if you like this might be with your own finger, through masturbation, not someone else's. If something like anal massage or insertion with fingers doesn't feel nice, it's very unlikely than anal intercourse with a penis will feel nice. As well, if you feel conflicted about having sex at all, or anal sex particularly, it's going to be tough to relax for anything to feel nice.
If you do decide to have anal sex, be that now or later, it is advised to use condoms from a health standpoint. Anal sex presents risks of sexually transmitted infections, and even when a partner is clear of them, it still presents risks of bacterial infections simply because the rectum often carries traces of fecal matter.
Understand that I'm making no judgment about your values: people's values and ideals about sex, and what situations or scenarios they need to have sex be wanted and right for them, all vary a lot. For some people, marriage has nothing to do with when sex is or isn't right for them. For others, it does. For those wanting to save sex for marriage, some mean all sex, and some only mean certain kinds of sex.
But I'm always very concerned when I hear someone say that saving sex for marriage is very important to them, and yet they are considering having sex anyway, more often than not because it's something a partner is pushing for or wants for themselves. Sex outside of your own value system certainly isn't guaranteed to be awful or traumatic, but we can safely say it's much less likely to feel good for you -- physically and emotionally -- before, during and afterwards if you do something you just don't feel right about.
So, instead of jumping into anal sex, what I'd suggest you do first is spend some time thinking about your own values, what you want and need, and what's important to you in terms of what you think will make sex feel most right for you. Be sure that you have a pretty solid idea of where you stand with all of this right now: that's important for you, but it's also important to help you best communicate it clearly to a partner.
If you do feel like your mind is changing -- your mind, not just your boyfriend's -- about saving sex for marriage, then it'd be a good idea for you two to talk about that. If you've been doing "everything but," or just figuring sex isn't something you have to prepare for, you'll not only want to both revisit the topic in terms of your values and relationship, but it's also going to be time to talk about safer sex, birth control, and limits and boundaries. Be honest and realistic about sexual activity: don't try and pretend something isn't sex that is. That's just a likely recipe for doing things you'll regret and feel lousy about, and if any two people can't look at and talk about sex honestly, it's a good signal one or both aren't ready. If you're taking about having a kind of sex -- and that is okay with you -- then it's got to be okay enough to recognize it as the sex that it is.
I'd also suggest some talks together about how you can both make sexual decisions together that are about both of your wants, not just his. Are you feeling pressured? If so, chatting together about ways you can each voice desires or things you are curious about without making the other feel they have to do those things if you don't want to is important.
If you don't feel like your values have changed, and that holding off on sex until marriage is still a big deal for you, it seems like you need to restate that to your boyfriend clearly, and make clear that he can want what he wants, but you're just not going to go there. I'd also ask him that he really hear you on this, and be sure he can respect that: if he can't, what he needs to do is reevaluate if he can stay in this relationship with you within these bounds, not push for what he wants and you don't, or try and find loopholes so he can get around your limits and boundaries. Not everyone wants to wait until marriage, but enough people do that if that's what's best for you, but not for him, you're both likely to be able to find someone else whose values and needs are in step with your own. And if you two are both looking for a longtime partner, you're going to want someone as compatible with you as possible no matter what.
Lastly, if you need some extra counsel with this and your want to save sex until marriage is faith-based, I'd suggest a talk with your religious leader or someone else who shares your faith who you trust, can be candid with, and who you know will give you good counsel.