Most painful - Comes down to two - Wally, the first laxer I fucked in college, who's penis was the size of my left leg. I tried multiple positions in order to ease the whole "mother of God I'm getting impaled" and "i think I can feel his dick in my throat" feelings. No avail, had to suck that one up and walk like an idiot for a day. The other would be a baseballer who had an um...unusual situation...long story short, the key and the lock just didn't fucking add up correctly and for like two years I was completely not capable of peeing because his dick was hitting all the wrong things when we fucked. It was like having a UTI for 2 straight fucking years, but no medications could make it go away permanently. Doctors had NO idea what was going on, I went to like 27 specialists, my health insurance provider must have gone bankrupt. Then, my last specialist asked me an honest question about um...compatibility and shit and I answered honestly because at this point I had been poked, prodded and examined by more doctors that I didn't have any shame, and when he explained that it could be the cause, I was like ARE YOU FUCKING KIDDING ME. I couldn't have sex with the dude. It hurt too bad, during and after. I remember the first time I had sex after we broke up, I was nervous as fuck, particularly because the other due was larger than normal. But no problems whatsoever. So yeah, those two were the most painful. And no, since then, no problems in that department, thank fucking Jeebus.
Worst in terms of "what the fuck is the point of this?" - A college laxer post grad. I met him at my friends birthday, they went to college together. We got shitfaced, and he was apparently totally fucked up on coke (I don't do drugs so if someone is fucked up on shit I just assume they are shitfaced on booze because I'm totally inexperienced), and basically, so have you ever seen the Collin Farrell sex tape? Where he's all doped up on coke and having a fucking in depth conversation with himself? Yeah, that was this. "...." = thrusts, by the way, just for a reference.
"I....can't...believe....we're....doing...this....I.....thought....about it.....all....night....but....I never.....thought....it....was.....going....to....happen....you.....looked so......good....and.....you.....were.....talking....to....that other.....guy....and I just thought......you....wanted....him.....but.....now....I'm fucking.....you....and....it....feels-"
Dude, I'm here to bang, not to explore our feelings, alright? Jesus fucking Christ, what happened to the day and age where a girl could get fucked without having to talk to to the guy?! My GOD! Anyway, I just stared at him while he was on top of me, trying to figure out if he was going to like, slit my throat after he admitted he loved me or something. He couldn't finish, which was not shocking, but yeah. Terrible, terrible sex.
Worst in terms of "I can think of 30 other things I wish I were doing right now?" - I had sex with a Georgetown football player (does that even count?), and it was like straight outta that scene in Forgetting Sarah Marshall where he fucks that chick he meets in the club then rolls over and starts crying and thinking of his ex-girlfriend. Yeah, had that too. We bang, I'm not super attracted to him but I'm trying to get over my ex-boyfriend, I realize he has freckles and ugly boxer briefs and he's like, on the cusp of being a ginge, and after he goes into the bathroom and I roll over HYSTERICALLY crying (drunk, obviously). He came out and goes "Jesus Christ, are you okay?" and instead of copping to the fact that I was thinking of another dude THE WHOLE FUCKING TIME, I stroked the dudes ginger ego by saying "yeah, you're just so big and I'm not used to it, it hurt a little, but felt good". LIES. LIES. See dudes, the things women fucking do to make sure your egos don't get bruised. Fuck, I'm a good person. ;)