Let's be honest, the road to a perfect lay isn't easy, failure to get it up or to achieve an orgasm is always a very real and annoying possibility.
So there's plenty of artists who wrote songs about that. Let's showcase them.
First up here's Genesis, who in "Counting out time"
describe the enthusiastic and very horny teenager who got it all down to numbers but when the actual moment has arrived cannot make it work out in his favor.
"Jackass" star Steve-O once released a Hip Hop Album which completely bombed thanks to the fact that Steve-O has no sense of flow or Rhythm. He now says that making that album was the biggest mistake he ever made. But it DOES have several tracks about sex gone wrong, so I had plenty of choice. I went for "Poppin' off"
which is about premature ejaculation.
Here's the Lonely Island rapping about the same subject Steve-O had been talking about, the title says enough "Jizz in my pants"
Here's REM taking the female point of view in "Tongue". The subject is a woman who receives oral sex but the one giving it to her can't make her cum.
Staying in that vein, here's the Yeasty Girlz about their guy not willing to performing oral sex on them in "You suck"
But by far the darkest thing about sex gone wrong is when a song is about an STD. as Frank Zappa sings about in "Why does it hurt when I pee?"
Feel free to add more.