Dear Miss Cassandra,

I love porn. But lately, porn hasn’t been doing much to satisfy me. So recently, I’ve been trying something taboo in our culture, I’ve been going on live chats and seeking other people needing to satisfy themselves though webcam. Now, I don’t engage in emotional relationships, nor do I show them my face, but is this wrong to do? Even though I see it as an upgraded version. P.S. I am in a relationship. They don’t know that I do this.

Wow, okay, long question, a lot to unpack, so let’s get this started. Miss Cassandra is all about breaking sexual taboos. We live in a society that is not only terrified about talking about the nasty, but also just plain hypocritical. Most people have sex, and most people can get a little freaky­—I should know. Normally I would say, if you get pleasure from this and you aren’t hurting anyone, then go for it. If you are finding other people who are doing this, there must be a market for it.

But then we get to your last line, and this is where I am going to stop you. You are cheating. This is where you are going to try to interrupt me, with “but I am not actually sleeping with these people,” or “but it’s not about emotions.” To this I call BS. You are cheating. You are keeping something important from your partner. If you tell her and she’s okay with it, by all means get off how you need to, but I think we both know that she wouldn’t be (that’s why you haven’t told her yet).

Maybe take some time to talk this out with him. If your need for online sex comes from sexual disappointment in your own relationship, maybe you two can work out how to get freakier together. And if this is more of a fetish and is the only thing that will really get you off, then see if you can do it with him or if he’s okay with you continuing to live chat. If he says no, you are going to have to pick which is more important to you. I know it sucks, but thems the breaks.

 

 I hook up with this guy really consistently, and he has been pretty clear about this only being a hook up, and nothing more. But we get along really well and I think I want more than just sex. I am worried though, if I try to make him commit, I might just lose him and I do really like this guy.

I don’t want to go all back in my day, but here it goes: Whatever happened to dating? For all you kids who don’t know what that means, people used to go on these things called dates, usually to dinner or the movies or some other fun activity.  People could be dating multiple people and when people were asked out on dates, it wasn’t shocking and it wasn’t a marriage proposal. What I am trying to say is, it wasn’t serious. It was the opposite of serious. The problem is, the Facebook generation has made dating into cuffing season. But I digress, this is really more of a rant than solid advice, and I am not a rant columnist.

If you want more, you are going to have to tell him. Sorry, but those are the rules. If he likes you, he will step up. It is unfair to you to not get out of this what you want to be getting out of it. If you guys really do get along so well, there is nothing keeping you from being friends. Some boys (note boys and not men) are afraid of everything when it comes to intimacy, relationships, etc. but he shouldn’t be scared of friendship, at least let’s hope he’s not, or else that’s a whole other problem. You deserve to be important to him, no matter what happens, and remember that. Be sensitive, but be direct. And if he doesn’t understand that, there are so many other fish in the sea, just make sure to bring your bait.

 

Have a question for Miss Cassandra? Email it to highbrow@34st.com or submit anonymously using our tumblr, askmisscass.tumblr.com/ask.