I'm a 26-year-old woman who has never been able to fully grasp the concept of anal sex. Sure, I've seen it in every porn movie I've ever watched, but how in the world do they do it? I've tried it with my boyfriend and it's probably the most painful thing that has ever happened to me...and (excuse me for being frank) it wasn't even all the way in! Has everyone tried it except me? Is it really the "best orgasm ever"? Is it normal that it hurts me so much?
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Of course you have to WANT to do it to participate but it is stil gonna hurt initially no matter HOW you prepare. I KNOW!
It ALWAYS hurts the FIRST time, because you're not used to it. Trying something new is always weird or painful.
Like some others have said, start out with something small. Your finger, or something. Lube is very important. You'll need lots.
And just so you know, this is coming from a guy. Biggest thing I've used so far is a hairbrush, and you know what? I love it.