1. Seeing a vagina for the first time. Nothing can prepare you. You can talk a good game. You can look things up online. You can ask your "more experienced" friends who are lying to you about all the sex they have to draw you a map. But the first time you actually see it one in person, all your preparation goes out the window. It's like how people say photos of the Grand Canyon didn't prepare them for just how big it was. I'm not comparing the size of the Grand Canyon to vaginas, obviously, just the majesty and natural beauty.
- Getting drunk, limp dick, even if "this kind of thing **never happens."* It's happened to the best of us, and it really may have only happened once. But that doesn't stop us from getting embarrassed and making a terrible case for ourselves while we alternate between wiping the sweat off our brow and punching ourselves in the dick. "Seriously, this is so weird... I don't know why this is happening. Do you think it could be the 7 shots of whiskey I did earlier?"
3. Trying to act like he knows exactly where the clitoris is. Hopefully, after a few test runs, we've got everything figured out, but when we first get in there, we know that the clitoris is important, but we don't know how to get to it. I think part of us just assumed everything would be right there, in the open. Maybe we hoped your idea of dirty talk would be something along the lines of, "Oh, baby. Please stimulate my clitoris which as I'm sure you know is located right here, at the crest of the labia." But since that didn't happen, we either fumbled around awkwardly until you politely faked an orgasm or we just gave up after you said "ow" too much.
- Knowing a horrifying cramp is coming.** It sneaks up on us but we don't want to look like babies so we push through it, as if having sex is on the same level of athleticism as an Olympic triathlon.
- Getting a finger in the butt**. DON'T DO THIS WITHOUT ASKING.
- Realising too late that his pubes are a mess**. You know, you go through your whole life and you don't pay much mind to your pubic hair, and then one day it's as if you're struck by lighting and you finally see that coiled nest through someone else's eyes. This moment will probably come right in the middle of our first blow job.
- Not knowing how to put a condom on.** Yeah, sure. Prior history of anything you wear on your body suggests a condom is more like a long sleeve we'd just kind of pull our penis through. So if we weren't paying attention in health class the day they taught us about condoms (we were probably daydreaming about having sex, ironically), the tiny foil packaging giving way to a rubber circle is a bit baffling. Hope we brought more than one.
- Having his parents walk in on him. **This is why people become nuns. Also the whole God thing, but I think mostly because sex is now ruined forever.
9. Getting struck in the balls mid-sex. **It's like getting bit by a puppy, or burned by a hot steak. We feel betrayed by something we love.