Dear Ibby, A guy I’m seeing recently hinted that I’d be “unable to walk” after sleeping with him, as in he has a huge dick and he wants anal. What should I do?

Dear Ibby, A guy I’m seeing recently hinted that I’d be “unable to walk” after sleeping with him, as in he has a huge dick and he wants anal. What should I do?

SexMay 12, 2015

Wow; according to his indication that you'll be disabled, it sounds like you’re in for quite a time. He unabashedly makes it seem like never before, and never again, will the constitution of your anal sphincter be tested with such impressive mechanical stretch. And depending on who you are, this could either be a really good or really bad thing.

My first question to you: Have you had anal before? Fuck, you can’t respond, you’re made of paper or internet … If you’ve tried anal and had good experiences with it, then go for it. I mean it’s really remarkable the things humans can fit in their rectums.

But if you do decide to go through with it, make sure you really trust him. Make sure he’s willing to take it slowly and keep you comfortable. Talk about this with him beforehand. He’s got the big, crippling dick; I'm sure he already knows it can be painful for some chicks to take, so don’t feel weird about asking him to take it easy. Use rivers and estuaries of lube and don't eat any beefy, cheesy chalupas prior to the event. Personally, I think his vaguely ominous threat of disabling your ambulatory capacity is more of a male posturing technique than a legitimate concern, but then again, you know him better than me.

On the other hand, if you’re inexperienced with anal or you think the act might confine you to crutches, that’s a little, tiny bit fucked up (unless you're into that?). Sex shouldn't mangle you and resign you to a wheelchair, and if that's what he's planning on doing, don't try your inaugural anal with this dude of all dudes. I don’t care how much of anal fetish you have: Inserting a bowling-pin-like cock halfway to your thoracic floor without knowing what to expect is going to suck. Plus, losing your anal virginity to someone of that magnitude might ruin your opinion of anal and future desire to experiment with it, and that would also suck because when it's done right, a lot of women find it just dandy.

If you’ve got anal aspirations, you can train yourself to take that kind of cock with progressively larger butt plugs until you can comfortably insert something that massive into your body and still walk away from it — but what’s even more important than the increasing flexibility of your anus is whether or not you actually want this. I’m not doubting that you do; I know tons of chicks and dudes who would love nothing more than to be anally impaled. If you’re inexperienced or unsure, either hold off or work your way up to such an impressive physical feat. Trust me, the decades of shits you’ll take in your life will thank you, and we all know how important it is to keep those guys pleased.