I think we've had similar discussions here. Charles still wins this one with his masturbation story which maybe we can get him to recap again.
Worst in what way, Pwn? I mean, I've had really boring lovers and sometimes anal just doesn't work out due to tightness(but I'm a giver not a taker and rather talented if I do say so myself)... before but nothing so... dynamic. That I can think of right now. Sure, sometimes there are position issues....accidental penis tweaks... heads hitting walls while goin at it. Not enough lubrication. Eh... I almost have to think my sex life is boring with how little goes terribly wrong, but that's the opposite of true. ^^;
I've dealt with broken condoms before. Just not the type to freak out. (I think I suffer from ataraxia like slevin in lucky number slevin, if anyone gets that reference)
40$ and the morning after pill and it's not so bad.
On a similar note... Heterosexual sex without a condom is amazing, and if you're in a monogamous relationship, you're both clean and your girl can go on birthcontrol... it can be quite worth it. ;P