Can you recall your worst sexual experience? Why was it so awful? Did you do anything at the time to try to make it better?

Jack’s Answer

This was a very difficult question for me to answer.  Unlike Jill, I’m fortunate to not have a sexual experience that sticks out negatively in my mind.  I don’t have a story about a shotgun-toting overprotective father coming home while I was fucking his daughter doggy-style over the arm of the sofa.  I don’t have a story about a fortysomething divorcee who, once the sex was over, told me that we had sinned and now needed to kneel before Jesus and pray for forgiveness.  I don’t have a story about a Craigslist hookup gone completely wrong.  I don’t have a story about falling asleep in a stranger’s apartment and awakening in a bathtub full of ice with my kidney missing.  I don’t have a story about unexpected or unwanted pegging.  (Actually I do; it was this week’s Flash Fiction Friday.)  I don’t have a story about getting head from a woman who afterwards revealed herself to be physically male.  (Actually, I do; it’s The Crying Game.*)

It’s true that when I was single I didn’t have many bad experiences, but I also usually had a very positive outlook about sex.  To use Academy Award terminology, it was an honor just to be nominated.  I was happy to be getting laid, and never really considered that being on a different sexual wavelength than my partner made the sex bad.  Everyone is different, after all.  There were times when the sex wasn’t particularly spectacular, especially with someone I’d just met.  There were times when I didn’t get off.  There were times when my partner was not especially good at it, or even bad at it.  There were times when my partner was just not into it.  There were times when I was just not into it.  There were times when I was fucking beneath my station, so to speak.  (Don’t look at me like I’m some kind of arrogant asshole – there were far more times when my partner was fucking beneath her station.)  But of all these examples, there is absolutely nothing that I can say was so awful that I would have been better off staying home.

I’ll tell you what makes for a really bad sexual experience.  It’s something that I experienced more than a few times during my twenties.  It involves going to a bar, trying desperately to pick someone up by the time the place closes, failing to do so, returning to my apartment, masturbating, and going to sleep.  And you know what?  Even that wasn’t so bad.

Jill’s Answer

If you’ve been reading our blog for awhile, you probably already know about the incident I consider the worst sex I’ve ever had.  It occurred pretty early on in my sex life, and I’m very proud of the fact that I didn’t let it shape my attitudes about sex, trust, and relationships forever.

I was dating a guy who was pretty hung, and the sex was really good.  He was also preoccupied with anal sex, and even asked for it the first time we had sex.  I’d never had anal sex before and I wasn’t ready to start.  Even if I was, I would have had a lot of apprehension about taking a cock as big as his in my ass.  He and I had been dating for three months, and one Saturday morning we were fooling around in his living room.  I’d just finished giving him oral sex and he bent me over the couch and fucked me doggy style, my favorite position.  Right out of the blue, he pulled out of my pussy and literally slammed it in my ass.  He made it about halfway in.  I screamed, and then I cried.  It hurt worse than I could have imagined, and I went into shock as a means of dealing with the pain.

I didn’t really do anything to make it better while it was happening.  He was only inside me for fifteen seconds, but the pain and the shock took a lot longer to wear off.  He initially claimed that it was an accident, but as he had been asking since almost day one for anal, I didn’t believe him.  Later he confirmed my doubts when he contradicted his earlier claim by saying he thought I would enjoy it.  I couldn’t trust him, and the fact that he was unconcerned with my feelings meant that he and I could go no further.  I broke up with him soon after.  He just wasn’t the person I thought he was.  No, I mean he literally wasn’t the person I thought he was.  The name he had given me was a fake name.

Because of this experience, it took me a very long time to try anal again.  But I’m very glad that I did.  With the right person, someone who cares about me and is considerate of my feelings and of my enjoyment of it, anal is awesome.  I was worried that it would be difficult to trust my next sexual partner.  But I realized that it wasn’t fair to judge the next guy based on the actions of some asshole and his obsession with my asshole.

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*Spoilers my ass.  The movie is twenty years old.