Scarleteen

I have two questions, and they're both pretty different.

1. I'm really self-conscious about myself, and my boyfriend hasn't seen me completely naked before. I always keep a tank top on when we have sex. I'm a b cup and I sometimes stuff my bras, to look bigger. I'm really comfortable with him now, and want to show him everything, but don't know what to do. Should I talk to him about it first, or should I just take everything off next time?

2. Not too long ago, I posted about thinking about having unprotected sex with my boyfriend. I've decided we won't do that. But, lately, I've been wanting to try something new. Anal sounds kind of interesting, but I don't really know how to ask my boyfriend about it. I feel like he might think I'm weird or something. It doesn't necessarily have to be anal sex, (I'd be okay with it if he just fingers), but how could I ask him?

I think with the first, that's totally up to you. You might want to figure, though, this probably won't be done big reveal to him. It's you who probably feels your breasts look very different with stuffing. Might help take some of the pressure off to bear that in mind.

With the latter, you just say something like, "I have been feeling curious about maybe exploring some kind of anal sex: is that anything you might be interested in?"

Maybe he'll think that's weird, but maybe not, and even if he did, it's not like there's a problem with someone thinking something we suggest is weird. It's okay to be weird (this message brought to you by a lifelong weirdo in so many ways), and it's okay to have sexual interests partners don't share.

Hey Nervousone,

Even though your questions are different, I see a common theme of trying to figure out how to communicate about sex. Last time Sam gave you a really great article on how to talk about sex (here it is again: Be a Blabbermouth

There isn't much more I can add, but I do think it can be helpful to consider what is the worst (or best) thing that can happen when you talk openly/honestly about sex in a healthy relationship. This can get rid of some of the pressure. A lot of times that "worst" is the fear of rejection or there being some awkwardness. But even if your boyfriend decides he doesn't want to try anal sex that doesn't mean he is rejecting you! And awkwardness might feel uncomfortable in the moment but it is a feeling that will likely go away (pretty quickly too). It can also make it easier to communicate in the future, in a way, lowering the "awkwardness threshold" for future conversations or situations.

I asked him about trying anal, and he said yes. We're going to try tomorrow. He said he'll start off with fingering, and maybe oral to help me relax to get ready for actual sex. For fingering and oral, (aside from showering before), is there anything else I should do to be ready? And when it comes time for sex, I have condoms and lube. But I've heard anal kinda hurts. Is there anything else we can do to make it easier, if possible?

Hi nervousone,

I'm glad the talk went! It sounds like you're already planning to go slow, so the other big thing that can make anal comfortable is lube. Lots and lots of lube. And communication is also really important. If you start to feel pain or discomfort, let him know it's time to stop and take a break. Anal sex is not supposed to be painful or uncomfortable, it's meant to feel pleasurable. So if you're feeling pain, it's time to stop.

Is there anyone who could give me a general idea on what it feels like? Is it a lot like regular sex, or is it more like he'd put it in and I'd be like "ooooookay that's weird"? That's probably more of an opinion question, but I'm just curious. Also, is anal something we could do in addition to vaginal sex, or is it something better left to be on it's own?

Really, that'd be like me describing to you how it feels to have someone hold my hand. Not only is my hand, and how it feels to have my hand held, potentially going to feel different for me than it might for you, how it even feels just for me is going to depend on who's holding it, how I feel about that, how they're holding it and a huge host of other factors. There's just no way to tell a person how having a body part touched feels to everyone, because there isn't a way that feels for everyone or even to one person.

But you know, you have a finger, so you can certainly touch yourself and see how it feels. And really, when we can first try something by ourselves when it comes to sex, it's usually good that we do before we bring it on the road with anyone else. So, since you're curious about this, and you actually CAN give yourself this answer very generally in a way we or anyone else can't, why not go ahead and find out at least for and by yourself to even get the most general sense of if you like this and if you even like that enough to want to do it with a partner?

(I don't know what you mean, by the way, by if it can be done in addition to any kind of sex with your vagina. Do you mean at the same time? If so, then the answer is that it depends on if something is possible, and then, if it is, if you like it or not.)