Dear Freak of the Week,
This guy I’ve been hooking up with asked to try anal, which I’ve never done before. I laughed it off last time but now I’m kind of curious. How do I bring up that I’m interested but also have never done it before and am a little nervous?
Sincerely,
“At your back door yelling ’cause I want to come in”
Dear “At your back door yelling ’cause I want to come in,”
It might interest readers to know that “Freak of the Week” was originally conceived of as a sex advice column, so your question is a welcome return to our roots!
While this might sound strange, I think it might be helpful to approach this question by thinking of your first time doing any new sex act with a person as essentially a more advanced version of regular sex. Regular sex requires consent, awareness of your partner’s needs and communication throughout. Once you’ve had sex with someone multiple times, these things may start to come more naturally. However, if you’re engaging with someone new or trying something new with even a consistent partner, these situations require extra and intentional awareness of the aforementioned factors.
The reason I start with this explanation is because the fact you two are only hooking up gives me just a little bit of pause. I feel obligated to ask: How consistent is this, and are you using the best sex practices when you see this guy? “Hookups” at Dartmouth can often mean you only see this person after going out, perhaps when you’re drunk, and you don’t have a very deep emotional connection with them. There are situations where healthy sex can come from these types of arrangements, but they can often cause slightly riskier situations, especially when trying new things like anal. This is why I would advise you to ensure that you are definitely using “best practices” when you see this guy before you immediately jump into something new.
Now, if you are comfortable with that qualifier, this situation should be relatively straightforward. One important prep tip: If you don’t usually use lube, you should definitely get some. You can wait until he brings it up, or bring it up yourself. Be clear and unashamed about never having tried anal, but say that you are curious and open to it. Make sure to do plenty of foreplay, and begin slowly with ample communication, even if it feels like too much or unnecessary.
Make sure to be very clear if you feel at all uncomfortable or want to stop. Oh, and this might also be a little bit gross, but don’t be surprised if it gets a little bit messy.
I hope you and your partner are able to safely explore this new experience with each other!
- Eli
Eli Moyse ’27 is an opinion editor and columnist for The Dartmouth. He studies government and creative writing. He publishes various personal work under a pen name on Substack (https://substack.com/@wesmercer), and you can find his other work in various publications.
