Should I do it?; Wrong hole!

Dan Savage

Dear Dan: I’m a virgin in my late 20s. I’m not waiting until marriage, just for the right person. I’ve dated enough and had enough fun to continue being a happy, normal, socially competent guy, much to the disbelief of my various knuckle-dragging, vagina-blinded pals. I’ve been dating this gal for a few months. She’s special — we have tons of chemistry and she cares about me. We had a brief conversation about my lack of sexperience when we first started dating, and she was very cool about it. I really like this girl, but I’m not sure yet if she’s the future Mrs. I am a worrier (thanks, mom!), and I find myself thinking that if I share this with her and somewhere down the road we end up breaking up, she’s going to be even more devastated because I shared my first time with her. Am I just having silly virgin worries? Not only am I concerned about her feelings if things don’t work out, but I’m also concerned that I might become vagina-blinded — that I might immediately tell this girl I want to spend my life with her just because she’s having sex with me only to find myself a few years down the road feeling trapped. What should I do?

— Very Indecisive, Really Gettin’ Naughty

Dear VIRGN: You should fuck this girl already — provided, of course, that this girl wants to fuck you.

You could wind up saying things you come to regret or have to walk back — her vagina might be that bedazzling — but that’s an unavoidable risk, and not one that’s unique to virgins. The right vagina, ass, face, skill set, or bank balance can blind a fucker with decades of experience. The only way to avoid vagina-blindness — or ass-blindness, etc. — is to never have sex with anyone. And I don’t think you’re interested in celibacy, so stop freaking out about the risk that you’ll imprint, duckling-like, on the first vagina your pee-pee sees the inside of.

You must also eliminate “sexperience” from your vocabulary, VIRGN, as it’s equal parts cloying and annoying.

Dear Dan: I’ve been with my boyfriend for more than a year. He’s the first person I’ve had sex with. Four times now while we were having passionate sex, he has slipped out of my vagina and accidentally penetrated me anally. That shit hurts, and I can’t help but cry. I know he feels super guilty each time. I love sex, but I’m kind of scared every time we have it now. We’ve engaged in a little anal play before, and I wasn’t really a fan. But I’m not adverse to the idea of using a butt plug. Do you think this would work? Surely other people have this problem too, right?

— Wrong Hole, Anal Torment

Dear WHAT: My own personal sexperience with anal led me to doubt claims of accidental anal penetration, WHAT, as anal penetration always required focus, precision, and proper breathing techniques — in my own sexperience. But listeners of the Savage Lovecast schooled me in Episode 340, and I’m now convinced that accidental anal penetration is something too many women have sexperienced. (Do you see how annoying that is, VIRGN?)

A strategically deployed butt plug sounds like a sexcellent solution to the problem, WHAT, but get yourself a plug with a wider-than-usual base to prevent your boyfriend’s misdirected cock from pushing the plug, base and all, all the way in you (ouch) or his misdirected cock from sliding in alongside the plug. (If you hate single penetration, you’ll really hate double penetration.)

If the problem persists even with a plug — if your boyfriend’s cock is constantly slamming into the plug in a way that you find uncomfortable — a thumbtack glued to the base of the plug will inspire your boyfriend to be more focused and precise.

And speaking of the Savage Lovecast, we’re coming up on our 500th episode, which is a significant milestone for this relatively new genre/platform/doohickey. If you’re not already listening, find it here: And a big thanks to Nancy Hartunian, the Lovecast’s producer since Episode 1, and to the tech-savvy, at-risk youth who pushed me to start podcasting before it was cool. 

Send questions to [email protected] and follow @fakedansavage on Twitter.


Please enter your comment!
Please enter your name here