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The oil-based ones are also pretty annoying to get off afterwards.

We used Vaseline, but my boyfriend later realized that it deadens sensation on the skin, which was obviously helpful for my asshole but bad for his orgasm.

You might have heard that too much lube takes away the friction that makes it feel good for the dude. There is no such thing as too much lube, because it makes it feel slightly less like you are using your butthole as a handbag for a flashlight. Between thin water-based lubes (like Astroglide) and thicker ones (KY), go with the thicker ones, because they don't dry out as quickly.

In sex educator Tristan Taormino's crazy-helpful , she mentions that Crisco has been a favorite of the LGBT community for a long time, but it's bad to use with condoms because it can eventually poke tiny holes in the latex.

I can totally relate to this now, because before I used to say I'd never have butt sex and then this weekend I had it.

Like watching Jason Statham movies and camping and losing the final and only virginity that you've retained since After-Prom. Either way is 100 percent fine, and if he keeps pressuring you when you have made it clear that it is not on the table, tell him to suck it. Even if you're monogamous, a condom is probably a good idea.