Return of the Dreaded Ex

Posted on July 27, 2012



This story is from Rebecca, a 25-year-old journalist in NYC, as told to Raz:

I met Ashton through my friend Sarah, who said he was a great guy who recently got out of a serious relationship. I was skeptical at first, but then she showed me a picture, and he was so pretty! Plus, Sarah swore that it wasn’t a bad breakup—that they had just grown apart. She said Ashton and his ex, Leslie, were still friendly and even hung out in the same social circle. What a mature end to a relationship, I thought.

Ashton was even better looking in person and had a sexy Australian accent to boot, so after our first date I was sold. He seemed pretty into me, too. On our fourth date, he admitted to me that the split with Leslie hadn’t been as awesome as I’d heard. He wanted a clean break, and was upset that she kept calling his close friends to hang out. “Sometimes,” he said,  “She’ll just show up to my apartment to watch TV with my two roommates. It’s weird.” OK, so not as mature as I thought, but I did agree with him: People need space after a breakup.

Later that night we headed back to his apartment, and I met his roommates. Then, he offered to give me the tour. We ended up in his bedroom. Let the most awkward hookup ever commence:

So we’re kissing on the couch, and, slowly but surely, clothes start coming off. Ashton’s pants were around his ankles when, in a romantic/dramatic move he decided to lift me up and carry me to the bed, which was behind the couch. We didn’t quite make it. Instead, he tripped over the couch and sent me sprawling to the floor.

He stared down at me, stunned. With no injuries to speak of, I laughed it off and led him to the bed where we picked up where we’d left off. Things were going well, and Ashton reached for a condom. But as soon as he slipped it on, his penis lost its excitement. “Sorry,” he said, clearly embarrassed. “It’s been a while since I’ve had to use a condom.”

The last thing I wanted was for him to wish he was back with Leslie so he could go condom-free, so I decided to help him out with a little oral stimulation. I went down there and started doing my thing, and it was working beautifully. But suddenly, there was a commotion in the other room.

One of his roommate’s was shouting: “Leslie! What are you doing here?”

Other roommate: “Wow, it’s Leslie!”

Damnit Leslie!

I don’t know whether they were screaming her name intentionally to prepare Ashton in case she tried to find him, or whether they were just loud talkers. Either way, Ashton’s penis lost its excitement again. Now we could hear them all talking, including what must have been Leslie’s squeaky voice. Ashton had that stunned look on his face.

I didn’t know what to do, so I asked, “Do you want me to keep going?”

“Yes,” he said, almost too quickly.

So I did, as we listened to the boys and Leslie yammer on a couple rooms over.

Finally, it was clear that his penis was literally going nowhere.

“I’m gonna go,” I said.

“I’ll walk you home,” he said.

His apartment had a back exit, thank God, so I never had to actually meet Leslie. We put on our clothes in silence. We snuck down the stairs in silence. Then, we walked the twenty minutes home—in silence.

There wasn’t a fifth date.

Posted in: Your Stories