Dear Miss Cassandra, my boyfriend is in London for the semester and I want to try Skype sex. But it just feels really awkward. Any tips for the digital set? 

Well honey, on the Internet you can always get as freaky as you want. I think Abraham Lincoln once said that­—it’s pretty much law. But if you are feeling awkward, start slow. Maybe start with a flirty strip tease and have him do the same. Or try simple dirty talk like, “If you were here, this is what I’d do to you right now…” These are fairly tame and can be made even tamer if you acknowledge the inherent comedy of the situation. Skype sex is awkward because it cuts out the best part of sex: touching. If you get a little silly, it’ll be a lot less awkward. Try doing a silly dance that turns sexy or being ridiculous in your dirty talk before you graduate to the serious stuff.

Another pro–tip is underwear. You know all the super hot underwear that you never actually wear before having sex? During real life sex, they will almost always go fully ignored (trust me, he’s usually trying to get them off fast). When he’s on another continent, he’ll have to notice your underwear. Use it well.

Just remember there is no reason to feel awkward. This is someone you care about and who cares about you—sex in any form shouldn’t be awkward. If it is, you either have to communicate with him about it or find a way to fix it. I believe in you. Now get your gigabytes in his ram drive.


I’m just entering the gay community at Penn. Are you supposed to ask a guy if he’s clean before you have sex? Or do you say that you’re clean? 

No matter what community you’re in or coming into (read “cumming into”) you should be having safe sex. I cannot stress this one enough. And a big part of safe sex is communication (well that and several other steps). Talking is not enough—you really should use protection.

As to whom is thinking what, I understand where you are coming from. Will he think of you as a person who is too safe because you take steps to prevent STIs or will he think you probably have an STI because you think about being clean in the first place? I have one answer for you: who cares what he thinks? If he wants to have sex with you, he should understand the risk and appreciate that he’s with someone who takes sex seriously.

People can lie or be unaware if they are STI–free, so encourage those that you get funky with to get tested. But that really should be a no brainer, and as I always say: you shouldn’t be giving brainers to guys who don’t do it safely, anyway.


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