How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!
Dear How to Do It,
I’ve been with my guy for two years. While we have fantastic sex, one thing I love is missing: anal. I’ve enjoyed anal sex in the past and want it with him, but he has an extraordinarily long, fat penis. It’s something to behold. And Tab A just won’t fit into Slot B. To get used to his size, I’ve tried graduated training plugs but the largest is still smaller than his “plug.” It’s worth noting that his length is not preventing penetration—his girth is.
So, I’m literally asking “how to do it,” anally. Thanks for your, um, input.
—Not Just the Tip
Dear Not Just the Tip,
Inflatable butt plugs. I’ve seen them starting